Identification

Name
Doxepin
Accession Number
DB01142  (APRD00398)
Type
Small Molecule
Groups
Approved
Description

Doxepin hydrochloride is a dibenzoxepin-derivative tricyclic antidepressant (TCA). TCAs are structurally similar to phenothiazines. They contain a tricyclic ring system with an alkyl amine substituent on the central ring. In non-depressed individuals, doxepin does not affect mood or arousal, but may cause sedation. In depressed individuals, doxepin exerts a positive effect on mood. TCAs are potent inhibitors of serotonin and norepinephrine reuptake. Tertiary amine TCAs, such as doxepin and amitriptyline, are more potent inhibitors of serotonin reuptake than secondary amine TCAs, such as nortriptyline and desipramine. TCAs also down-regulate cerebral cortical β-adrenergic receptors and sensitize post-synaptic serotonergic receptors with chronic use. The antidepressant effects of TCAs are thought to be due to an overall increase in serotonergic neurotransmission. TCAs also block histamine H1 receptors, α1-adrenergic receptors and muscarinic receptors, which accounts for their sedative, hypotensive and anticholinergic effects (e.g. blurred vision, dry mouth, constipation, urinary retention), respectively. Doxepin has less sedative and anticholinergic effects than amitriptyline. See toxicity section below for a complete listing of side effects. Doxepin may be used to treat depression and insomnia. Unlabeled indications include chronic and neuropathic pain, and anxiety. Doxepin may also be used as a second line agent to treat idiopathic urticaria.

Structure
Thumb
Synonyms
  • Cidoxepin
  • Doxepin
Product Ingredients
IngredientUNIICASInChI Key
Cidoxepin hydrochlorideXI27WMG8QK25127-31-5MHNSPTUQQIYJOT-CULRIWENSA-N
Doxepin Hydrochloride3U9A0FE9N51229-29-4MHNSPTUQQIYJOT-UHFFFAOYSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Doxepin HydrochlorideCream50 mg/gTopicalRenaissance Pharma, Inc.2016-03-07Not applicableUs
Doxepine-10 - CapCapsule10 mgOralPro Doc Limitee1995-12-312010-07-13Canada
Doxepine-100 - CapCapsule100 mgOralPro Doc Limitee1995-12-312010-07-13Canada
Doxepine-150 - CapCapsule150 mgOralPro Doc Limitee1995-12-312009-07-23Canada
Doxepine-25 -capCapsule25 mgOralPro Doc Limitee1995-12-312010-07-13Canada
Doxepine-50 - CapCapsule50 mgOralPro Doc Limitee1995-12-312010-07-13Canada
Doxepine-75 - CapCapsule75 mgOralPro Doc Limitee1995-12-312010-07-13Canada
PrudoxinCream50 mg/gTopicalHealthpoint2001-10-012015-11-30Us
PrudoxinCream50 mg/gTopicalPrestium Pharma, Inc.2015-06-01Not applicableUs
PrudoxinCream50 mg/gTopicalSmith & Nephew, Inc.2012-12-212015-11-30Us
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Alti-doxepin - Cap 10mgCapsule10 mgOralAltimed Pharma Inc.1995-12-312005-05-27Canada
Alti-doxepin-cap 25mgCapsule25 mgOralAltimed Pharma Inc.1995-12-312005-05-27Canada
Alti-doxepin-cap 50mgCapsule50 mgOralAltimed Pharma Inc.1995-12-312005-05-27Canada
Alti-doxepin-cap 75mgCapsule75 mgOralAltimed Pharma Inc.1995-12-312005-05-27Canada
Apo-doxepinCapsule50 mgOralApotex Corporation1993-12-31Not applicableCanada
Apo-doxepinCapsule150 mgOralApotex Corporation1993-12-31Not applicableCanada
Apo-doxepinCapsule10 mgOralApotex Corporation1993-12-31Not applicableCanada
Apo-doxepinCapsule25 mgOralApotex Corporation1993-12-31Not applicableCanada
Apo-doxepinCapsule75 mgOralApotex Corporation1993-12-31Not applicableCanada
Apo-doxepinCapsule100 mgOralApotex Corporation1993-12-31Not applicableCanada
Unapproved/Other Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Doxepin HydrochlorideCream50 mg/gTopicalRemedy Repack2017-11-24Not applicableUs
International/Other Brands
Adapin (PennwaIt) / Aponal (Pfizer) / Curatin / Doxepine (Shou Chan) / Quitaxon (Lexphar) / Sinequan (Pfizer) / Zonalon
Categories
UNII
F96TTB8728
CAS number
1668-19-5
Weight
Average: 279.3761
Monoisotopic: 279.162314299
Chemical Formula
C19H21NO
InChI Key
ODQWQRRAPPTVAG-BOPFTXTBSA-N
InChI
InChI=1S/C19H21NO/c1-20(2)13-7-11-17-16-9-4-3-8-15(16)14-21-19-12-6-5-10-18(17)19/h3-6,8-12H,7,13-14H2,1-2H3/b17-11-
IUPAC Name
dimethyl(3-{9-oxatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,11,13-hexaen-2-ylidene}propyl)amine
SMILES
[H]C(CCN(C)C)=C1C2=CC=CC=C2COC2=CC=CC=C12

Pharmacology

Indication

Doxepin is used for the treatment of depression and/or anxiety. It can also be used for chronic urticaria and in the management of pain.

Structured Indications
Pharmacodynamics

Doxepin, a tricyclic antidepressant of the dibenzoxepin type, is used to treat depression and anxiety and, topically, pruritus associated with eczema. Doxepin has substantial anticholinergic and sedative effects. The E (trans)-isomer is more active as a serotonin reuptake inhibitor while the Z-isomer acts as a sedative.

Mechanism of action

The mechanism of action of doxepin is not completely understood. It is thought that like amitriptyline, doxepin enhances the actions of norepinephrine and serotonin by blocking their reuptake at the neuronal membrane. However, doxepin weakly inhibits the reuptake of dopamine. Doxepin may also act on histamine H1-receptors, resulting in sedative effects, and β-adrenergic receptors. It is also an antagonist of 5-hydroxytryptamine (serotonin) receptors, alpha-1 adrenergic receptor, and muscarinic cholinergic receptors.

TargetActionsOrganism
AHistamine H1 receptor
antagonist
Human
AHistamine H2 receptor
antagonist
Human
ASodium-dependent noradrenaline transporter
inhibitor
Human
ASodium-dependent serotonin transporter
inhibitor
Human
A5-hydroxytryptamine receptor 2A
antagonist
Human
A5-hydroxytryptamine receptor 2B
antagonist
Human
A5-hydroxytryptamine receptor 2C
antagonist
Human
AMuscarinic acetylcholine receptor M1
antagonist
Human
AMuscarinic acetylcholine receptor M2
antagonist
Human
AMuscarinic acetylcholine receptor M3
antagonist
Human
AMuscarinic acetylcholine receptor M4
antagonist
Human
AMuscarinic acetylcholine receptor M5
antagonist
Human
UAlpha-1A adrenergic receptor
antagonist
Human
UAlpha-1B adrenergic receptor
antagonist
Human
UAlpha-1D adrenergic receptor
antagonist
Human
A5-hydroxytryptamine receptor 1A
antagonist
Human
UAlpha-2A adrenergic receptor
antagonist
Human
UAlpha-2B adrenergic receptor
antagonist
Human
UAlpha-2C adrenergic receptor
antagonist
Human
UD(2) dopamine receptor
antagonist
Human
U5-hydroxytryptamine receptor 6
binder
Human
UHistamine H4 receptor
binder
Human
UPotassium voltage-gated channel subfamily H member 2Not AvailableHuman
Absorption

Well-absorbed from the GI tract. Peak plasma concentrations occur within 2 hours of oral administration.

Volume of distribution
Not Available
Protein binding

Doxepin and desmethyldoxepin is 80% protein bound. It is also a lipophillic drug and is capable of crossing the blood-brain-barrier.

Metabolism

Extensively metabolized in the liver via the same pathways as other TCAs. N-demethylation produces an active metabolite, N-desmethyldoxepin. CYP2D6 specifically hydroxylates the E-isomer.

Route of elimination
Not Available
Half life

6 - 24.5 hours

Clearance
Not Available
Toxicity

LD50=26 (mg/kg) (in mice, iv); LD50=16 (mg/kg) (in rats, iv); Cardiac dysrhythmias, severe hypotension, convulsions, and CNS depression, including coma. Changes in the electrocardiogram, particularly in QRS axis or width, are clinically significant indicators of tricyclic antidepressant toxicity. Side effects include: sedation, hypotension, blurred vision, dry mouth, constipation, urinary retention, postural hypotension, tachycardia, hypertension, ECG changes, heart failure, impaired memory and delirium, and precipitation of hypomanic or manic episodes in bipolar depression. Withdrawal symptoms include gastrointestinal disturbances, anxiety, and insomnia.

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Doxepin H1-Antihistamine ActionDrug action
Doxepin Metabolism PathwayDrug metabolism
Pharmacogenomic Effects/ADRs
Interacting Gene/EnzymeAllele nameGenotype(s)Defining Change(s)Type(s)DescriptionDetails
Cytochrome P450 2D6CYP2D6*3Not Available2549delAEffect Directly StudiedThe presence of this polymorphism in CYP2D6 is associated with reduced or poor metabolism of doxepin.Details
Cytochrome P450 2D6CYP2D6*4Not AvailableA alleleEffect Directly StudiedThe presence of this polymorphism in CYP2D6 is associated with reduced or poor metabolism of doxepin.Details
Cytochrome P450 2D6CYP2D6*5Not AvailableWhole-gene deletionEffect Directly StudiedThe presence of this polymorphism in CYP2D6 is associated with reduced or poor metabolism of doxepin.Details
Cytochrome P450 2D6CYP2D6*6Not Available1707delTEffect Directly StudiedThe presence of this polymorphism in CYP2D6 is associated with reduced or poor metabolism of doxepin.Details
Cytochrome P450 2C19CYP2C19*2Not Available681G>AEffect Directly StudiedThe presence of this polymorphism in CYP2C19 is associated with poor metabolism of doxepin.Details
Cytochrome P450 2C19CYP2C19*3Not Available636G>AEffect Directly StudiedThe presence of this polymorphism in CYP2C19 is associated with reduced or poor metabolism of doxepin.Details
Cytochrome P450 2D6CYP2D6*7Not Available2935A>CEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*8Not Available1758G>TEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*11Not Available883G>CEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*12Not Available124G>AEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*13Not AvailableCYP2D7/2D6 hybrid gene structureEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*14ANot Available1758G>AEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*15Not Available137insT, 137_138insTEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*19Not Available2539_2542delAACTEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*20Not Available1973_1974insGEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*21Not Available2573insCEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*31Not Available-1770G>A / -1584C>G  … show all Effect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*36Not Available100C>T / -1426C>T  … show all Effect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*38Not Available2587_2590delGACTEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*40Not Available1863_1864ins(TTT CGC CCC)2Effect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*42Not Available3259_3260insGTEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*44Not Available2950G>CEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*47Not Available100C>T / -1426C>T  … show all Effect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*51Not Available-1584C>G / -1235A>G  … show all Effect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*56Not Available3201C>TEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*57Not Available100C>T / 310G>T  … show all Effect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*62Not Available4044C>TEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*68ANot Available-1426C>T / -1235A>G  … show all Effect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*68BNot AvailableSimilar but not identical switch region compared to CYP2D6*68A. Found in tandem arrangement with CYP2D6*4.Effect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*69Not Available2988G>A / -1426C>T  … show all Effect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*92Not Available1995delCEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*100Not Available-1426C>T / -1235A>G  … show all Effect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*101Not Available-1426C>T / -1235A>G  … show all Effect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.Details
Cytochrome P450 2C19CYP2C19*2ANot Available681G>AEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.Details
Cytochrome P450 2C19CYP2C19*2BNot Available681G>AEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.Details
Cytochrome P450 2C19CYP2C19*4Not Available1A>GEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.Details
Cytochrome P450 2C19CYP2C19*5Not Available1297C>TEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.Details
Cytochrome P450 2C19CYP2C19*6Not Available395G>AEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.Details
Cytochrome P450 2C19CYP2C19*7Not Available19294T>AEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.Details
Cytochrome P450 2C19CYP2C19*22Not Available557G>C / 991A>GEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.Details
Cytochrome P450 2C19CYP2C19*24Not Available99C>T / 991A>G  … show all Effect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.Details
Cytochrome P450 2C19CYP2C19*35Not Available12662A>GEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*3Not AvailableG alleleEffect Directly StudiedThe presence of this polymorphism in CYP2D6 is associated with reduced or poor metabolism of doxepin.Details
Cytochrome P450 2D6CYP2D6*4Not Available3877G>AEffect Directly StudiedThe presence of this polymorphism in CYP2D6 is associated with reduced or poor metabolism of doxepin.Details

Interactions

Drug Interactions
DrugInteractionDrug group
1,10-PhenanthrolineThe serum concentration of Doxepin can be increased when it is combined with 1,10-Phenanthroline.Experimental
2,5-Dimethoxy-4-ethylamphetamine2,5-Dimethoxy-4-ethylamphetamine may decrease the sedative activities of Doxepin.Experimental, Illicit
2,5-Dimethoxy-4-ethylthioamphetamine2,5-Dimethoxy-4-ethylthioamphetamine may decrease the sedative activities of Doxepin.Experimental
3,4-DichloroisocoumarinThe serum concentration of Doxepin can be increased when it is combined with 3,4-Dichloroisocoumarin.Experimental
3,4-Methylenedioxyamphetamine3,4-Methylenedioxyamphetamine may decrease the sedative activities of Doxepin.Experimental, Illicit
4-(2-Aminoethyl)Benzenesulfonyl FluorideThe serum concentration of Doxepin can be increased when it is combined with 4-(2-Aminoethyl)Benzenesulfonyl Fluoride.Experimental
4-Bromo-2,5-dimethoxyamphetamine4-Bromo-2,5-dimethoxyamphetamine may decrease the sedative activities of Doxepin.Experimental, Illicit
4-MethoxyamphetamineDoxepin may decrease the antihypertensive activities of 4-Methoxyamphetamine.Experimental, Illicit
7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline may increase the serotonergic activities of Doxepin.Experimental
AbirateroneThe serum concentration of Doxepin can be increased when it is combined with Abiraterone.Approved
AcenocoumarolDoxepin may increase the anticoagulant activities of Acenocoumarol.Approved
AfatinibThe serum concentration of Afatinib can be increased when it is combined with Doxepin.Approved
AgmatineDoxepin may decrease the antihypertensive activities of Agmatine.Experimental, Investigational
AlogliptinThe serum concentration of Doxepin can be increased when it is combined with Alogliptin.Approved
Alpha-1-proteinase inhibitorThe serum concentration of Doxepin can be increased when it is combined with Alpha-1-proteinase inhibitor.Approved
AltretamineAltretamine may increase the orthostatic hypotensive activities of Doxepin.Approved
AmiodaroneThe metabolism of Doxepin can be decreased when combined with Amiodarone.Approved, Investigational
AmobarbitalThe metabolism of Doxepin can be increased when combined with Amobarbital.Approved, Illicit
AmphetamineAmphetamine may decrease the sedative activities of Doxepin.Approved, Illicit
AmprenavirThe serum concentration of Doxepin can be increased when it is combined with Amprenavir.Approved
Antithrombin III humanThe serum concentration of Doxepin can be increased when it is combined with Antithrombin III human.Approved
ApixabanThe serum concentration of Doxepin can be increased when it is combined with Apixaban.Approved
ApomorphineDoxepin may decrease the antihypertensive activities of Apomorphine.Approved, Investigational
ApraclonidineDoxepin may decrease the antihypertensive activities of Apraclonidine.Approved
AprepitantThe serum concentration of Doxepin can be increased when it is combined with Aprepitant.Approved, Investigational
AprotininThe serum concentration of Doxepin can be increased when it is combined with Aprotinin.Approved, Withdrawn
ArbutamineThe risk or severity of adverse effects can be increased when Doxepin is combined with Arbutamine.Approved
ArformoterolThe risk or severity of adverse effects can be increased when Doxepin is combined with Arformoterol.Approved, Investigational
ArgatrobanThe serum concentration of Doxepin can be increased when it is combined with Argatroban.Approved, Investigational
ArmodafinilThe metabolism of Doxepin can be decreased when combined with Armodafinil.Approved, Investigational
ArtemetherThe metabolism of Doxepin can be decreased when combined with Artemether.Approved
AsunaprevirThe serum concentration of Doxepin can be increased when it is combined with Asunaprevir.Approved, Investigational
AtazanavirThe serum concentration of Atazanavir can be decreased when it is combined with Doxepin.Approved, Investigational
AtomoxetineThe metabolism of Doxepin can be decreased when combined with Atomoxetine.Approved
AzithromycinThe metabolism of Doxepin can be decreased when combined with Azithromycin.Approved
BambuterolThe risk or severity of adverse effects can be increased when Doxepin is combined with Bambuterol.Approved, Investigational
BarbexacloneThe metabolism of Doxepin can be increased when combined with Barbexaclone.Experimental
BarbitalThe metabolism of Doxepin can be increased when combined with Barbital.Illicit
BatimastatThe serum concentration of Doxepin can be increased when it is combined with Batimastat.Experimental
BenazeprilThe serum concentration of Doxepin can be increased when it is combined with Benazepril.Approved, Investigational
BenzamidineThe serum concentration of Doxepin can be increased when it is combined with Benzamidine.Experimental
BenzphetamineDoxepin may decrease the antihypertensive activities of Benzphetamine.Approved, Illicit
Benzylpenicilloyl PolylysineDoxepin may decrease effectiveness of Benzylpenicilloyl Polylysine as a diagnostic agent.Approved
BetahistineThe therapeutic efficacy of Betahistine can be decreased when used in combination with Doxepin.Approved
BetaxololThe metabolism of Doxepin can be decreased when combined with Betaxolol.Approved
BethanidineDoxepin may decrease the antihypertensive activities of Bethanidine.Approved
BivalirudinThe serum concentration of Doxepin can be increased when it is combined with Bivalirudin.Approved, Investigational
BoceprevirThe metabolism of Doxepin can be decreased when combined with Boceprevir.Approved, Withdrawn
BortezomibThe metabolism of Doxepin can be decreased when combined with Bortezomib.Approved, Investigational
BosentanThe serum concentration of Doxepin can be decreased when it is combined with Bosentan.Approved, Investigational
BosutinibThe serum concentration of Bosutinib can be decreased when it is combined with Doxepin.Approved
Brentuximab vedotinThe serum concentration of Brentuximab vedotin can be increased when it is combined with Doxepin.Approved
BrofaromineBrofaromine may increase the serotonergic activities of Doxepin.Experimental
BromocriptineDoxepin may decrease the antihypertensive activities of Bromocriptine.Approved, Investigational
BupropionThe metabolism of Doxepin can be decreased when combined with Bupropion.Approved
CaffeineThe metabolism of Doxepin can be decreased when combined with Caffeine.Approved
CamostatThe serum concentration of Doxepin can be increased when it is combined with Camostat.Experimental
CandoxatrilThe serum concentration of Doxepin can be increased when it is combined with Candoxatril.Experimental
CandoxatrilatThe serum concentration of Doxepin can be increased when it is combined with Candoxatrilat.Experimental
CapecitabineThe metabolism of Doxepin can be decreased when combined with Capecitabine.Approved, Investigational
CaptoprilThe serum concentration of Doxepin can be increased when it is combined with Captopril.Approved
CarbamazepineThe metabolism of Doxepin can be increased when combined with Carbamazepine.Approved, Investigational
CefditorenThe serum concentration of Cefditoren can be decreased when it is combined with Doxepin.Approved
CefpodoximeDoxepin can cause a decrease in the absorption of Cefpodoxime resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved, Vet Approved
CefuroximeDoxepin can cause a decrease in the absorption of Cefuroxime resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
CelecoxibThe metabolism of Doxepin can be decreased when combined with Celecoxib.Approved, Investigational
CeliprololThe risk or severity of adverse effects can be increased when Doxepin is combined with Celiprolol.Approved, Investigational
CeritinibThe serum concentration of Doxepin can be increased when it is combined with Ceritinib.Approved
ChloramphenicolThe metabolism of Doxepin can be decreased when combined with Chloramphenicol.Approved, Vet Approved
ChloroquineThe metabolism of Doxepin can be decreased when combined with Chloroquine.Approved, Vet Approved
ChlorphentermineChlorphentermine may decrease the sedative activities of Doxepin.Illicit, Withdrawn
ChlorpromazineThe metabolism of Doxepin can be decreased when combined with Chlorpromazine.Approved, Vet Approved
CholecalciferolThe metabolism of Doxepin can be decreased when combined with Cholecalciferol.Approved, Nutraceutical
CholesterolThe serum concentration of Doxepin can be increased when it is combined with Cholesterol.Experimental, Investigational
ChymostatinThe serum concentration of Doxepin can be increased when it is combined with Chymostatin.Experimental
CilastatinThe serum concentration of Doxepin can be increased when it is combined with Cilastatin.Approved
CilazaprilThe serum concentration of Doxepin can be increased when it is combined with Cilazapril.Approved
CimetidineThe metabolism of Doxepin can be decreased when combined with Cimetidine.Approved
CinacalcetThe serum concentration of Doxepin can be increased when it is combined with Cinacalcet.Approved
CirazolineDoxepin may increase the vasopressor activities of Cirazoline.Experimental
CitalopramThe risk or severity of adverse effects can be increased when Doxepin is combined with Citalopram.Approved
ClarithromycinThe metabolism of Doxepin can be decreased when combined with Clarithromycin.Approved
ClemastineThe metabolism of Doxepin can be decreased when combined with Clemastine.Approved
ClenbuterolThe risk or severity of adverse effects can be increased when Doxepin is combined with Clenbuterol.Approved, Investigational, Vet Approved
ClobazamThe metabolism of Doxepin can be decreased when combined with Clobazam.Approved, Illicit
ClomipramineThe metabolism of Doxepin can be decreased when combined with Clomipramine.Approved, Vet Approved
ClonidineDoxepin may decrease the antihypertensive activities of Clonidine.Approved
ClorindioneDoxepin may increase the anticoagulant activities of Clorindione.Experimental
ClotrimazoleThe metabolism of Doxepin can be decreased when combined with Clotrimazole.Approved, Vet Approved
ClozapineThe metabolism of Doxepin can be decreased when combined with Clozapine.Approved
CobicistatThe serum concentration of Doxepin can be increased when it is combined with Cobicistat.Approved
CocaineThe metabolism of Doxepin can be decreased when combined with Cocaine.Approved, Illicit
ColchicineThe serum concentration of Colchicine can be increased when it is combined with Doxepin.Approved
ConivaptanThe serum concentration of Conivaptan can be increased when it is combined with Doxepin.Approved, Investigational
CrisaboroleThe metabolism of Doxepin can be decreased when combined with Crisaborole.Approved, Investigational
CrizotinibThe metabolism of Doxepin can be decreased when combined with Crizotinib.Approved
CyclosporineThe metabolism of Doxepin can be decreased when combined with Cyclosporine.Approved, Investigational, Vet Approved
Cyproterone acetateThe serum concentration of Doxepin can be decreased when it is combined with Cyproterone acetate.Approved, Investigational
CysteamineThe therapeutic efficacy of Cysteamine can be decreased when used in combination with Doxepin.Approved, Investigational
Dabigatran etexilateThe serum concentration of the active metabolites of Dabigatran etexilate can be increased when Dabigatran etexilate is used in combination with Doxepin.Approved
DabrafenibThe serum concentration of Doxepin can be decreased when it is combined with Dabrafenib.Approved
DapoxetineThe risk or severity of adverse effects can be increased when Dapoxetine is combined with Doxepin.Investigational
DarexabanThe serum concentration of Doxepin can be increased when it is combined with Darexaban.Investigational
DarifenacinThe metabolism of Doxepin can be decreased when combined with Darifenacin.Approved, Investigational
DarunavirThe serum concentration of Doxepin can be increased when it is combined with Darunavir.Approved
DasatinibThe serum concentration of Doxepin can be increased when it is combined with Dasatinib.Approved, Investigational
DeferasiroxThe serum concentration of Doxepin can be decreased when it is combined with Deferasirox.Approved, Investigational
DelanzomibThe serum concentration of Doxepin can be increased when it is combined with Delanzomib.Investigational
DelaprilThe serum concentration of Doxepin can be increased when it is combined with Delapril.Experimental
DelavirdineDoxepin can cause a decrease in the absorption of Delavirdine resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
DesipramineThe metabolism of Doxepin can be decreased when combined with Desipramine.Approved
DesmopressinThe risk or severity of adverse effects can be increased when Doxepin is combined with Desmopressin.Approved
DexmedetomidineDoxepin may decrease the antihypertensive activities of Dexmedetomidine.Approved, Vet Approved
DexmethylphenidateThe risk or severity of adverse effects can be increased when Dexmethylphenidate is combined with Doxepin.Approved
DextroamphetamineDextroamphetamine may decrease the sedative activities of Doxepin.Approved, Illicit
DicoumarolDoxepin may increase the anticoagulant activities of Dicoumarol.Approved
DiethylpropionDiethylpropion may decrease the sedative activities of Doxepin.Approved, Illicit
DihydroergotamineDoxepin may decrease the antihypertensive activities of Dihydroergotamine.Approved
DiltiazemThe metabolism of Doxepin can be decreased when combined with Diltiazem.Approved
DiphenadioneDoxepin may increase the anticoagulant activities of Diphenadione.Experimental
DiphenhydramineThe metabolism of Doxepin can be decreased when combined with Diphenhydramine.Approved
DipivefrinDoxepin may decrease the antihypertensive activities of Dipivefrin.Approved
DobutamineThe risk or severity of adverse effects can be increased when Doxepin is combined with Dobutamine.Approved
DosulepinThe metabolism of Doxepin can be decreased when combined with Dosulepin.Approved
DoxorubicinThe serum concentration of Doxorubicin can be increased when it is combined with Doxepin.Approved, Investigational
DoxycyclineThe metabolism of Doxepin can be decreased when combined with Doxycycline.Approved, Investigational, Vet Approved
DronedaroneThe metabolism of Doxepin can be decreased when combined with Dronedarone.Approved
DroxidopaDoxepin may decrease the antihypertensive activities of Droxidopa.Approved, Investigational
DuloxetineDuloxetine may increase the serotonergic activities of Doxepin.Approved
EcabetThe serum concentration of Doxepin can be increased when it is combined with Ecabet.Approved, Investigational
EdoxabanThe serum concentration of Edoxaban can be increased when it is combined with Doxepin.Approved
EfavirenzThe metabolism of Doxepin can be decreased when combined with Efavirenz.Approved, Investigational
ElafinThe serum concentration of Doxepin can be increased when it is combined with Elafin.Investigational
EliglustatThe metabolism of Doxepin can be decreased when combined with Eliglustat.Approved
EnalaprilThe serum concentration of Doxepin can be increased when it is combined with Enalapril.Approved, Vet Approved
EnalaprilatThe serum concentration of Doxepin can be increased when it is combined with Enalaprilat.Approved
EnalkirenThe serum concentration of Doxepin can be increased when it is combined with Enalkiren.Experimental
EnzalutamideThe serum concentration of Doxepin can be decreased when it is combined with Enzalutamide.Approved
EphedraDoxepin may decrease the antihypertensive activities of Ephedra.Approved, Nutraceutical, Withdrawn
Epigallocatechin GallateThe serum concentration of Doxepin can be increased when it is combined with Epigallocatechin Gallate.Investigational
EpinephrineDoxepin may decrease the antihypertensive activities of Epinephrine.Approved, Vet Approved
ErgotamineDoxepin may decrease the antihypertensive activities of Ergotamine.Approved
ErlotinibThe serum concentration of Erlotinib can be decreased when it is combined with Doxepin.Approved, Investigational
ErythromycinThe metabolism of Doxepin can be decreased when combined with Erythromycin.Approved, Vet Approved
EscitalopramThe risk or severity of adverse effects can be increased when Doxepin is combined with Escitalopram.Approved, Investigational
Eslicarbazepine acetateThe metabolism of Doxepin can be decreased when combined with Eslicarbazepine acetate.Approved
EsomeprazoleThe metabolism of Doxepin can be decreased when combined with Esomeprazole.Approved, Investigational
Ethyl biscoumacetateDoxepin may increase the anticoagulant activities of Ethyl biscoumacetate.Withdrawn
EtomidateDoxepin may decrease the antihypertensive activities of Etomidate.Approved
EtravirineThe metabolism of Doxepin can be decreased when combined with Etravirine.Approved
EverolimusThe serum concentration of Everolimus can be increased when it is combined with Doxepin.Approved
FaldaprevirThe serum concentration of Doxepin can be increased when it is combined with Faldaprevir.Investigational
FenoterolThe risk or severity of adverse effects can be increased when Doxepin is combined with Fenoterol.Approved, Investigational
FesoterodineThe serum concentration of the active metabolites of Fesoterodine can be increased when Fesoterodine is used in combination with Doxepin.Approved
FloxuridineThe metabolism of Doxepin can be decreased when combined with Floxuridine.Approved
FluconazoleThe metabolism of Doxepin can be decreased when combined with Fluconazole.Approved
FluindioneDoxepin may increase the anticoagulant activities of Fluindione.Investigational
FluorouracilThe metabolism of Doxepin can be decreased when combined with Fluorouracil.Approved
FluoxetineThe risk or severity of adverse effects can be increased when Fluoxetine is combined with Doxepin.Approved, Vet Approved
FluvastatinThe metabolism of Doxepin can be decreased when combined with Fluvastatin.Approved
FluvoxamineThe risk or severity of adverse effects can be increased when Fluvoxamine is combined with Doxepin.Approved, Investigational
FormoterolThe risk or severity of adverse effects can be increased when Doxepin is combined with Formoterol.Approved, Investigational
FosamprenavirThe serum concentration of Fosamprenavir can be decreased when it is combined with Doxepin.Approved
FosaprepitantThe serum concentration of Doxepin can be increased when it is combined with Fosaprepitant.Approved
FosinoprilThe serum concentration of Doxepin can be increased when it is combined with Fosinopril.Approved
FosphenytoinThe metabolism of Doxepin can be increased when combined with Fosphenytoin.Approved
FurazolidoneFurazolidone may increase the serotonergic activities of Doxepin.Approved, Investigational, Vet Approved
Fusidic AcidThe serum concentration of Doxepin can be increased when it is combined with Fusidic Acid.Approved
GabexateThe serum concentration of Doxepin can be increased when it is combined with Gabexate.Investigational
GefitinibThe serum concentration of Gefitinib can be decreased when it is combined with Doxepin.Approved, Investigational
GeldanamycinThe serum concentration of Doxepin can be increased when it is combined with Geldanamycin.Experimental, Investigational
GemfibrozilThe metabolism of Doxepin can be decreased when combined with Gemfibrozil.Approved
GepefrineGepefrine may decrease the sedative activities of Doxepin.Experimental
GM6001The serum concentration of Doxepin can be increased when it is combined with GM6001.Experimental
GuanabenzDoxepin may decrease the antihypertensive activities of Guanabenz.Approved, Investigational
GuanfacineDoxepin may decrease the antihypertensive activities of Guanfacine.Approved, Investigational
HaloperidolThe metabolism of Doxepin can be decreased when combined with Haloperidol.Approved
HarmalineHarmaline may increase the serotonergic activities of Doxepin.Experimental
HexobarbitalThe metabolism of Doxepin can be increased when combined with Hexobarbital.Approved
HyaluronidaseThe therapeutic efficacy of Hyaluronidase can be decreased when used in combination with Doxepin.Approved, Investigational
HydroxyamphetamineHydroxyamphetamine may decrease the sedative activities of Doxepin.Approved
IdelalisibThe metabolism of Doxepin can be decreased when combined with Idelalisib.Approved
IdraparinuxThe serum concentration of Doxepin can be increased when it is combined with Idraparinux.Investigational
ImatinibThe metabolism of Doxepin can be decreased when combined with Imatinib.Approved
ImidaprilThe serum concentration of Doxepin can be increased when it is combined with Imidapril.Investigational
ImipramineThe metabolism of Doxepin can be decreased when combined with Imipramine.Approved
IndacaterolThe risk or severity of adverse effects can be increased when Doxepin is combined with Indacaterol.Approved
IndinavirThe serum concentration of Indinavir can be decreased when it is combined with Doxepin.Approved
IobenguaneThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Doxepin.Approved, Investigational
Iofetamine I-123Iofetamine I-123 may decrease the sedative activities of Doxepin.Approved
IproniazidIproniazid may increase the serotonergic activities of Doxepin.Withdrawn
IrbesartanThe metabolism of Doxepin can be decreased when combined with Irbesartan.Approved, Investigational
IsavuconazoniumThe metabolism of Doxepin can be decreased when combined with Isavuconazonium.Approved, Investigational
IsoetarineThe risk or severity of adverse effects can be increased when Doxepin is combined with Isoetarine.Approved
IsoflurophateThe serum concentration of Doxepin can be increased when it is combined with Isoflurophate.Approved, Investigational, Withdrawn
IsoniazidThe metabolism of Doxepin can be decreased when combined with Isoniazid.Approved
IsoprenalineThe risk or severity of adverse effects can be increased when Doxepin is combined with Isoprenaline.Approved
IsradipineThe metabolism of Doxepin can be decreased when combined with Isradipine.Approved
ItraconazoleThe serum concentration of Itraconazole can be decreased when it is combined with Doxepin.Approved, Investigational
IvacaftorThe serum concentration of Doxepin can be increased when it is combined with Ivacaftor.Approved
IxazomibThe serum concentration of Doxepin can be increased when it is combined with Ixazomib.Approved
KetoconazoleThe serum concentration of Ketoconazole can be decreased when it is combined with Doxepin.Approved, Investigational
L-TryptophanL-Tryptophan may increase the serotonergic activities of Doxepin.Approved, Nutraceutical, Withdrawn
LedipasvirThe serum concentration of Ledipasvir can be decreased when it is combined with Doxepin.Approved
LeflunomideThe metabolism of Doxepin can be decreased when combined with Leflunomide.Approved, Investigational
LepirudinThe serum concentration of Doxepin can be increased when it is combined with Lepirudin.Approved
LetaxabanThe serum concentration of Doxepin can be increased when it is combined with Letaxaban.Investigational
LevonordefrinDoxepin may decrease the antihypertensive activities of Levonordefrin.Approved
LevosalbutamolThe risk or severity of adverse effects can be increased when Doxepin is combined with Levosalbutamol.Approved
LidocaineThe metabolism of Doxepin can be decreased when combined with Lidocaine.Approved, Vet Approved
LinagliptinThe serum concentration of Doxepin can be increased when it is combined with Linagliptin.Approved
LinezolidLinezolid may increase the serotonergic activities of Doxepin.Approved, Investigational
LisdexamfetamineLisdexamfetamine may decrease the sedative activities of Doxepin.Approved, Investigational
LisinoprilThe serum concentration of Doxepin can be increased when it is combined with Lisinopril.Approved, Investigational
LithiumLithium may increase the neurotoxic activities of Doxepin.Approved
LobeglitazoneThe metabolism of Doxepin can be decreased when combined with Lobeglitazone.Approved, Investigational
LofexidineDoxepin may decrease the antihypertensive activities of Lofexidine.Approved, Investigational
LopinavirThe metabolism of Doxepin can be decreased when combined with Lopinavir.Approved
LorcaserinThe metabolism of Doxepin can be decreased when combined with Lorcaserin.Approved
LorpiprazoleThe serum concentration of Doxepin can be increased when it is combined with Lorpiprazole.Approved
LosartanThe metabolism of Doxepin can be decreased when combined with Losartan.Approved
LovastatinThe metabolism of Doxepin can be decreased when combined with Lovastatin.Approved, Investigational
LuliconazoleThe serum concentration of Doxepin can be increased when it is combined with Luliconazole.Approved
LumacaftorThe serum concentration of Doxepin can be decreased when it is combined with Lumacaftor.Approved
LumefantrineThe metabolism of Doxepin can be decreased when combined with Lumefantrine.Approved
ManidipineThe metabolism of Doxepin can be decreased when combined with Manidipine.Approved, Investigational
MelagatranThe serum concentration of Doxepin can be increased when it is combined with Melagatran.Experimental
MephedroneMephedrone may decrease the sedative activities of Doxepin.Investigational
MephentermineDoxepin may increase the vasopressor activities of Mephentermine.Approved
MesalazineThe therapeutic efficacy of Mesalazine can be decreased when used in combination with Doxepin.Approved
MetaraminolDoxepin may increase the vasopressor activities of Metaraminol.Approved, Investigational
MethadoneThe metabolism of Doxepin can be decreased when combined with Methadone.Approved
MethamphetamineDoxepin may decrease the antihypertensive activities of Methamphetamine.Approved, Illicit
MethohexitalThe metabolism of Doxepin can be increased when combined with Methohexital.Approved
MethotrimeprazineThe metabolism of Doxepin can be decreased when combined with Methotrimeprazine.Approved
MethoxamineDoxepin may increase the vasopressor activities of Methoxamine.Approved, Investigational
MethoxyphenamineMethoxyphenamine may decrease the sedative activities of Doxepin.Experimental
Methylene blueDoxepin may increase the serotonergic activities of Methylene blue.Approved, Investigational
MethylphenidateThe risk or severity of adverse effects can be increased when Methylphenidate is combined with Doxepin.Approved, Investigational
MethylphenobarbitalThe metabolism of Doxepin can be increased when combined with Methylphenobarbital.Approved
MetoclopramideThe risk or severity of adverse effects can be increased when Metoclopramide is combined with Doxepin.Approved, Investigational
MetoprololThe serum concentration of Metoprolol can be increased when it is combined with Doxepin.Approved, Investigational
MetyrosineThe risk or severity of adverse effects can be increased when Metyrosine is combined with Doxepin.Approved
MexiletineThe metabolism of Doxepin can be decreased when combined with Mexiletine.Approved
MidodrineDoxepin may increase the vasopressor activities of Midodrine.Approved
MidomafetamineMidomafetamine may decrease the sedative activities of Doxepin.Experimental, Illicit, Investigational
MidostaurinThe metabolism of Doxepin can be decreased when combined with Midostaurin.Approved
MifepristoneThe serum concentration of Doxepin can be increased when it is combined with Mifepristone.Approved, Investigational
MinaprineMinaprine may increase the serotonergic activities of Doxepin.Approved
MirabegronThe metabolism of Doxepin can be decreased when combined with Mirabegron.Approved
MitotaneThe serum concentration of Doxepin can be decreased when it is combined with Mitotane.Approved
MMDAMMDA may decrease the sedative activities of Doxepin.Experimental, Illicit
MoclobemideThe metabolism of Doxepin can be decreased when combined with Moclobemide.Approved
ModafinilThe metabolism of Doxepin can be decreased when combined with Modafinil.Approved, Investigational
MoexiprilThe serum concentration of Doxepin can be increased when it is combined with Moexipril.Approved
MoxonidineThe therapeutic efficacy of Moxonidine can be decreased when used in combination with Doxepin.Approved, Investigational
N-(3-Propylcarbamoyloxirane-2-Carbonyl)-Isoleucyl-ProlineThe serum concentration of Doxepin can be increased when it is combined with N-(3-Propylcarbamoyloxirane-2-Carbonyl)-Isoleucyl-Proline.Experimental
NafamostatThe serum concentration of Doxepin can be increased when it is combined with Nafamostat.Approved, Investigational
NaloxegolThe serum concentration of Naloxegol can be increased when it is combined with Doxepin.Approved
NaphazolineDoxepin may decrease the antihypertensive activities of Naphazoline.Approved
NefazodoneThe metabolism of Doxepin can be decreased when combined with Nefazodone.Approved, Withdrawn
NelfinavirThe serum concentration of Nelfinavir can be decreased when it is combined with Doxepin.Approved
NetupitantThe serum concentration of Doxepin can be increased when it is combined with Netupitant.Approved
NevirapineThe metabolism of Doxepin can be increased when combined with Nevirapine.Approved
NialamideNialamide may increase the serotonergic activities of Doxepin.Withdrawn
NicardipineThe metabolism of Doxepin can be decreased when combined with Nicardipine.Approved
NicorandilDoxepin may increase the hypotensive activities of Nicorandil.Approved, Investigational
NilotinibThe serum concentration of Nilotinib can be decreased when it is combined with Doxepin.Approved, Investigational
NitroaspirinThe serum concentration of Doxepin can be increased when it is combined with Nitroaspirin.Investigational
NorepinephrineDoxepin may decrease the antihypertensive activities of Norepinephrine.Approved
OlaparibThe metabolism of Doxepin can be decreased when combined with Olaparib.Approved
OlodaterolThe risk or severity of adverse effects can be increased when Doxepin is combined with Olodaterol.Approved
OmapatrilatThe serum concentration of Doxepin can be increased when it is combined with Omapatrilat.Investigational
OmeprazoleThe metabolism of Doxepin can be decreased when combined with Omeprazole.Approved, Investigational, Vet Approved
OrciprenalineThe risk or severity of adverse effects can be increased when Doxepin is combined with Orciprenaline.Approved
OsimertinibThe serum concentration of Doxepin can be increased when it is combined with Osimertinib.Approved
OtamixabanThe serum concentration of Doxepin can be increased when it is combined with Otamixaban.Investigational
OxymetazolineDoxepin may decrease the antihypertensive activities of Oxymetazoline.Approved
PalbociclibThe serum concentration of Doxepin can be increased when it is combined with Palbociclib.Approved
PaliperidoneDoxepin may decrease the antihypertensive activities of Paliperidone.Approved
PanobinostatThe serum concentration of Doxepin can be increased when it is combined with Panobinostat.Approved, Investigational
PantoprazoleThe metabolism of Doxepin can be decreased when combined with Pantoprazole.Approved
PargylinePargyline may increase the serotonergic activities of Doxepin.Approved
ParoxetineThe risk or severity of adverse effects can be increased when Paroxetine is combined with Doxepin.Approved, Investigational
PazopanibThe serum concentration of Pazopanib can be increased when it is combined with Doxepin.Approved
Peginterferon alfa-2bThe serum concentration of Doxepin can be decreased when it is combined with Peginterferon alfa-2b.Approved
PentobarbitalThe metabolism of Doxepin can be increased when combined with Pentobarbital.Approved, Vet Approved
PergolideDoxepin may decrease the antihypertensive activities of Pergolide.Approved, Investigational, Vet Approved, Withdrawn
PerindoprilThe serum concentration of Doxepin can be increased when it is combined with Perindopril.Approved
PhenindioneDoxepin may increase the anticoagulant activities of Phenindione.Approved, Investigational
PhenobarbitalThe metabolism of Doxepin can be increased when combined with Phenobarbital.Approved
PhenprocoumonDoxepin may increase the anticoagulant activities of Phenprocoumon.Approved, Investigational
PhenterminePhentermine may decrease the sedative activities of Doxepin.Approved, Illicit
PhenylephrineDoxepin may increase the vasopressor activities of Phenylephrine.Approved
PhenylpropanolamineThe risk or severity of adverse effects can be increased when Doxepin is combined with Phenylpropanolamine.Approved, Vet Approved, Withdrawn
PhenytoinThe metabolism of Doxepin can be increased when combined with Phenytoin.Approved, Vet Approved
PhosphoramidonThe serum concentration of Doxepin can be increased when it is combined with Phosphoramidon.Experimental
PirbuterolThe risk or severity of adverse effects can be increased when Doxepin is combined with Pirbuterol.Approved
PirlindolePirlindole may increase the serotonergic activities of Doxepin.Approved
PosaconazoleThe serum concentration of Posaconazole can be decreased when it is combined with Doxepin.Approved, Investigational, Vet Approved
PrimidoneThe metabolism of Doxepin can be increased when combined with Primidone.Approved, Vet Approved
PrinomastatThe serum concentration of Doxepin can be increased when it is combined with Prinomastat.Investigational
ProcaterolThe risk or severity of adverse effects can be increased when Doxepin is combined with Procaterol.Approved, Investigational
PromazineThe metabolism of Doxepin can be decreased when combined with Promazine.Approved, Vet Approved
PrucaloprideThe serum concentration of Prucalopride can be increased when it is combined with Doxepin.Approved
PseudoephedrineDoxepin may decrease the antihypertensive activities of Pseudoephedrine.Approved
PyrimethamineThe metabolism of Doxepin can be decreased when combined with Pyrimethamine.Approved, Vet Approved
QuinaprilThe serum concentration of Doxepin can be increased when it is combined with Quinapril.Approved, Investigational
QuinidineDoxepin may increase the QTc-prolonging activities of Quinidine.Approved
QuinineThe metabolism of Doxepin can be decreased when combined with Quinine.Approved
RacecadotrilThe serum concentration of Doxepin can be increased when it is combined with Racecadotril.Investigational
RamiprilThe serum concentration of Doxepin can be increased when it is combined with Ramipril.Approved
RanolazineThe serum concentration of Ranolazine can be increased when it is combined with Doxepin.Approved, Investigational
RemikirenThe serum concentration of Doxepin can be increased when it is combined with Remikiren.Approved
RifabutinThe metabolism of Doxepin can be increased when combined with Rifabutin.Approved
RifampicinThe metabolism of Doxepin can be increased when combined with Rifampicin.Approved
RifapentineThe metabolism of Doxepin can be increased when combined with Rifapentine.Approved
RifaximinThe serum concentration of Rifaximin can be increased when it is combined with Doxepin.Approved, Investigational
RisedronateDoxepin can cause an increase in the absorption of Risedronate resulting in an increased serum concentration and potentially a worsening of adverse effects.Approved, Investigational
RisperidoneDoxepin may decrease the antihypertensive activities of Risperidone.Approved, Investigational
RitobegronRitobegron may decrease the sedative activities of Doxepin.Investigational
RitodrineThe risk or severity of adverse effects can be increased when Doxepin is combined with Ritodrine.Approved, Investigational
RitonavirThe metabolism of Doxepin can be decreased when combined with Ritonavir.Approved, Investigational
RivaroxabanThe serum concentration of Doxepin can be increased when it is combined with Rivaroxaban.Approved
RolapitantThe metabolism of Doxepin can be decreased when combined with Rolapitant.Approved
RopiniroleThe therapeutic efficacy of Ropinirole can be decreased when used in combination with Doxepin.Approved, Investigational
RucaparibThe metabolism of Doxepin can be decreased when combined with Rucaparib.Approved, Investigational
S-3304The serum concentration of Doxepin can be increased when it is combined with S-3304.Investigational
SalbutamolThe risk or severity of adverse effects can be increased when Doxepin is combined with Salbutamol.Approved, Vet Approved
SalmeterolThe risk or severity of adverse effects can be increased when Doxepin is combined with Salmeterol.Approved
SaquinavirThe serum concentration of Saquinavir can be increased when it is combined with Doxepin.Approved, Investigational
SarilumabThe therapeutic efficacy of Doxepin can be decreased when used in combination with Sarilumab.Approved
SaxagliptinThe serum concentration of Doxepin can be increased when it is combined with Saxagliptin.Approved
SecobarbitalThe metabolism of Doxepin can be increased when combined with Secobarbital.Approved, Vet Approved
SertralineThe risk or severity of adverse effects can be increased when Sertraline is combined with Doxepin.Approved
SildenafilThe metabolism of Doxepin can be decreased when combined with Sildenafil.Approved, Investigational
SilodosinThe serum concentration of Silodosin can be increased when it is combined with Doxepin.Approved
SiltuximabThe serum concentration of Doxepin can be decreased when it is combined with Siltuximab.Approved
SimeprevirThe serum concentration of Doxepin can be increased when it is combined with Simeprevir.Approved
SitagliptinThe serum concentration of Doxepin can be increased when it is combined with Sitagliptin.Approved, Investigational
SivelestatThe serum concentration of Doxepin can be increased when it is combined with Sivelestat.Investigational
Sodium phosphateThe risk or severity of adverse effects can be increased when Doxepin is combined with Sodium phosphate.Approved
SorafenibThe metabolism of Doxepin can be decreased when combined with Sorafenib.Approved, Investigational
SpiraprilThe serum concentration of Doxepin can be increased when it is combined with Spirapril.Approved
St. John's WortThe metabolism of Doxepin can be increased when combined with St. John's Wort.Approved, Investigational, Nutraceutical
StiripentolThe serum concentration of Doxepin can be increased when it is combined with Stiripentol.Approved
SulfadiazineThe metabolism of Doxepin can be decreased when combined with Sulfadiazine.Approved, Vet Approved
SulfamethoxazoleThe metabolism of Doxepin can be decreased when combined with Sulfamethoxazole.Approved
SulfisoxazoleThe metabolism of Doxepin can be decreased when combined with Sulfisoxazole.Approved, Vet Approved
TelaprevirThe metabolism of Doxepin can be decreased when combined with Telaprevir.Approved, Withdrawn
TelithromycinThe metabolism of Doxepin can be decreased when combined with Telithromycin.Approved
TemocaprilThe serum concentration of Doxepin can be increased when it is combined with Temocapril.Experimental, Investigational
Tenofovir disoproxilThe metabolism of Doxepin can be decreased when combined with Tenofovir disoproxil.Approved, Investigational
TerbinafineThe metabolism of Doxepin can be decreased when combined with Terbinafine.Approved, Investigational, Vet Approved
TerbutalineThe risk or severity of adverse effects can be increased when Doxepin is combined with Terbutaline.Approved
TeriflunomideThe serum concentration of Doxepin can be decreased when it is combined with Teriflunomide.Approved
ThalidomideDoxepin may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.Approved, Investigational, Withdrawn
TheophyllineThe metabolism of Doxepin can be decreased when combined with Theophylline.Approved
ThiamylalThe metabolism of Doxepin can be increased when combined with Thiamylal.Approved, Vet Approved
ThiopentalThe metabolism of Doxepin can be increased when combined with Thiopental.Approved, Vet Approved
ThioridazineThe serum concentration of Thioridazine can be increased when it is combined with Doxepin.Approved, Withdrawn
ThiorphanThe serum concentration of Doxepin can be increased when it is combined with Thiorphan.Experimental
TicagrelorThe metabolism of Doxepin can be decreased when combined with Ticagrelor.Approved
TiclopidineThe metabolism of Doxepin can be decreased when combined with Ticlopidine.Approved
TioclomarolDoxepin may increase the anticoagulant activities of Tioclomarol.Experimental
TipranavirThe metabolism of Doxepin can be decreased when combined with Tipranavir.Approved, Investigational
TizanidineDoxepin may decrease the antihypertensive activities of Tizanidine.Approved
TocilizumabThe serum concentration of Doxepin can be decreased when it is combined with Tocilizumab.Approved
TolbutamideThe metabolism of Doxepin can be decreased when combined with Tolbutamide.Approved
ToloxatoneToloxatone may increase the serotonergic activities of Doxepin.Approved
TopiramateThe metabolism of Doxepin can be decreased when combined with Topiramate.Approved
TopiroxostatThe metabolism of Doxepin can be decreased when combined with Topiroxostat.Approved, Investigational
TopotecanThe serum concentration of Topotecan can be increased when it is combined with Doxepin.Approved, Investigational
TramadolDoxepin may increase the neuroexcitatory activities of Tramadol.Approved, Investigational
TrandolaprilThe serum concentration of Doxepin can be increased when it is combined with Trandolapril.Approved
TranylcypromineThe metabolism of Doxepin can be decreased when combined with Tranylcypromine.Approved
TrimethoprimThe metabolism of Doxepin can be decreased when combined with Trimethoprim.Approved, Vet Approved
UbenimexThe serum concentration of Doxepin can be increased when it is combined with Ubenimex.Experimental, Investigational
UlinastatinThe serum concentration of Doxepin can be increased when it is combined with Ulinastatin.Investigational
Valproic AcidThe serum concentration of Doxepin can be increased when it is combined with Valproic Acid.Approved, Investigational
ValsartanThe metabolism of Doxepin can be decreased when combined with Valsartan.Approved, Investigational
VareniclineThe serum concentration of Varenicline can be increased when it is combined with Doxepin.Approved, Investigational
VemurafenibThe serum concentration of Doxepin can be increased when it is combined with Vemurafenib.Approved
VenlafaxineThe metabolism of Doxepin can be decreased when combined with Venlafaxine.Approved
VerapamilThe metabolism of Doxepin can be decreased when combined with Verapamil.Approved
VilanterolThe risk or severity of adverse effects can be increased when Doxepin is combined with Vilanterol.Approved
VildagliptinThe serum concentration of Doxepin can be increased when it is combined with Vildagliptin.Approved, Investigational
VincristineThe excretion of Vincristine can be decreased when combined with Doxepin.Approved, Investigational
VoriconazoleThe metabolism of Doxepin can be decreased when combined with Voriconazole.Approved, Investigational
WarfarinDoxepin may increase the anticoagulant activities of Warfarin.Approved
XimelagatranThe serum concentration of Doxepin can be increased when it is combined with Ximelagatran.Approved, Investigational, Withdrawn
XylometazolineDoxepin may decrease the antihypertensive activities of Xylometazoline.Approved
YohimbineThe serum concentration of Yohimbine can be increased when it is combined with Doxepin.Approved, Vet Approved
Z-Val-Ala-Asp fluoromethyl ketoneThe serum concentration of Doxepin can be increased when it is combined with Z-Val-Ala-Asp fluoromethyl ketone.Experimental
ZafirlukastThe metabolism of Doxepin can be decreased when combined with Zafirlukast.Approved, Investigational
ZiprasidoneThe metabolism of Doxepin can be decreased when combined with Ziprasidone.Approved
ZofenoprilThe serum concentration of Doxepin can be increased when it is combined with Zofenopril.Experimental
ZucapsaicinThe metabolism of Doxepin can be decreased when combined with Zucapsaicin.Approved
Food Interactions
  • Avoid alcohol.
  • Avoid excessive quantities of coffee or tea (caffeine).
  • Avoid St.John's Wort.
  • Take with food to reduce irritation.

References

Synthesis Reference

Luigi Schioppi, Brian Talmadge Dorsey, Michael Skinner, John Carter, Robert Mansbach, Philip Jochelson, Roberta L. Rogowski, Cara Casseday, Meredith Perry, Bryan Knox, "LOW-DOSE DOXEPIN FORMULATIONS AND METHODS OF MAKING AND USING THE SAME." U.S. Patent US20090074862, issued March 19, 2009.

US20090074862
General References
  1. Virtanen R, Iisalo E, Irjala K: Protein binding of doxepin and desmethyldoxepin. Acta Pharmacol Toxicol (Copenh). 1982 Aug;51(2):159-64. [PubMed:7113722]
  2. Virtanen R, Scheinin M, Iisalo E: Single dose pharmacokinetics of doxepin in healthy volunteers. Acta Pharmacol Toxicol (Copenh). 1980 Nov;47(5):371-6. [PubMed:7293791]
  3. Negro-Alvarez JM, Carreno-Rojo A, Funes-Vera E, Garcia-Canovas A, Abellan-Aleman AF, Rubio del Barrio R: Pharmacologic therapy for urticaria. Allergol Immunopathol (Madr). 1997 Jan-Feb;25(1):36-51. [PubMed:9111875]
  4. Sansone RA, Sansone LA: Pain, pain, go away: antidepressants and pain management. Psychiatry (Edgmont). 2008 Dec;5(12):16-9. [PubMed:19724772]
  5. Kirchheiner J, Meineke I, Muller G, Roots I, Brockmoller J: Contributions of CYP2D6, CYP2C9 and CYP2C19 to the biotransformation of E- and Z-doxepin in healthy volunteers. Pharmacogenetics. 2002 Oct;12(7):571-80. [PubMed:12360109]
External Links
KEGG Drug
D07875
KEGG Compound
C06971
PubChem Compound
667468
PubChem Substance
46505232
ChemSpider
580850
BindingDB
50079527
ChEBI
36691
ChEMBL
CHEMBL101740
Therapeutic Targets Database
DAP000177
PharmGKB
PA449409
IUPHAR
1225
Guide to Pharmacology
GtP Drug Page
HET
D7V
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Doxepin
ATC Codes
N06AA12 — Doxepin
AHFS Codes
  • 84:08.00 — Antipruritics and Local Anesthetics
  • 28:16.04.28 — Tricyclics and Other Norepinephrine-reuptake Inhibitors
PDB Entries
3rze
FDA label
Download (588 KB)
MSDS
Download (73.4 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0CompletedTreatmentParkinson's Disease (PD) / Sleeplessness1
2CompletedTreatmentIrritable Bowel Syndrome (IBS)1
2CompletedTreatmentSleep Initiation and Maintenance Disorders1
2RecruitingPreventionCancer, Breast1
3Active Not RecruitingSupportive CareHead and Neck Carcinoma / Mucositis / Oral Complications of Radiation Therapy / Pain1
3CompletedTreatmentAcute Oral Mucositis Pain1
3TerminatedTreatmentAnxiety Disorders / Dementias / Depression / Psychosomatic Disorders / Schizophrenic Disorders1
4CompletedDiagnosticHealthy Volunteers1
4CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Sleeplessness1
Not AvailableActive Not RecruitingSupportive CareAdvanced thymic carcinoma / Hypopharyngeal Carcinoma / Laryngeal Carcinoma / Lung Cancer Non-Small Cell Cancer (NSCLC) / Lung Cancer Small Cell Lung Cancer (SCLC) / Malignant Lymphomas / Malignant Pericardial Effusion / Malignant Pleural Effusions / Mesothelioma / Mesothelioma, Malignant / Metastatic Malignant Neoplasm in the Lung / Metastatic Malignant Neoplasm in the Pleura / Metastatic Malignant Neoplasm in the Spinal Cord / Non-Small Cell Lung Carcinoma (NSCLC) / Oesophageal Carcinoma / Sarcomas / Small Cell Lung Carcinoma / Soft Tissue Sarcoma (STS) / Thymic Carcinoma / Thymoma and Thymic Carcinoma / Thyroid Gland Carcinoma1
Not AvailableEnrolling by InvitationNot AvailableBipolar Disorder (BD)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Dosage forms
FormRouteStrength
CapsuleOral10 mg
CapsuleOral100 mg
CapsuleOral25 mg
CapsuleOral50 mg
CapsuleOral75 mg
CapsuleOral10 mg/1
CapsuleOral100 mg/1
CapsuleOral150 mg/1
CapsuleOral25 mg/1
CapsuleOral50 mg/1
CapsuleOral75 mg/1
SolutionOral10 mg/mL
Solution, concentrateOral10 mg/mL
CapsuleOral150 mg
TabletOral3 mg/1
TabletOral3.00 mg
TabletOral6 mg/1
TabletOral6.00 mg
CreamTopical50 mg/g
CreamTopical5 %
Prices
Unit descriptionCostUnit
Zonalon 5% Cream 45 gm Tube190.13USD tube
Zonalon 5% Cream 30 gm Tube144.29USD tube
Doxepin hcl powder8.88USD g
Doxepin 150 mg capsule3.33USD capsule
Prudoxin 5% cream3.05USD g
Sinequan 100 mg Capsule1.22USD capsule
Novo-Doxepin 150 mg Capsule1.18USD capsule
Sinequan 75 mg Capsule0.93USD capsule
Zonalon 5% cream0.89USD g
Doxepin HCl 150 mg capsule0.87USD capsule
Apo-Doxepin 100 mg Capsule0.68USD capsule
Novo-Doxepin 100 mg Capsule0.68USD capsule
Sinequan 50 mg Capsule0.64USD capsule
Doxepin 50 mg capsule0.57USD capsule
Doxepin HCl 100 mg capsule0.56USD capsule
Novo-Doxepin 75 mg Capsule0.52USD capsule
Apo-Doxepin 75 mg Capsule0.52USD capsule
Doxepin HCl 75 mg capsule0.43USD capsule
Apo-Doxepin 50 mg Capsule0.36USD capsule
Novo-Doxepin 50 mg Capsule0.36USD capsule
Sinequan 25 mg Capsule0.35USD capsule
Doxepin 10 mg capsule0.32USD capsule
Sinequan 10 mg Capsule0.28USD capsule
Doxepin HCl 50 mg capsule0.25USD capsule
Doxepin HCl 25 mg capsule0.23USD capsule
Doxepin 75 mg capsule0.21USD capsule
Doxepin HCl 10 mg capsule0.21USD capsule
Apo-Doxepin 10 mg Capsule0.2USD capsule
Apo-Doxepin 25 mg Capsule0.19USD capsule
Novo-Doxepin 25 mg Capsule0.19USD capsule
Doxepin 25 mg capsule0.18USD capsule
Doxepin 100 mg capsule0.14USD capsule
Doxepin HCl 10 mg/ml Concentrate0.13USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US6211229No2000-02-172020-02-17Us
US9107898No2008-05-012028-05-01Us
US8513299No2010-04-142030-04-14Us
US7915307No2007-08-242027-08-24Us
US9532971No2009-06-012029-06-01Us
US9486437No2007-05-182027-05-18Us
US9572814No2007-07-202027-07-20Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)< 25 °CPhysProp
boiling point (°C)265 °C at 2.00E-01 mm HgPhysProp
water solubility31.6 mg/L (at 25 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP4.29SANGSTER (1994)
logS-3.4ADME Research, USCD
Predicted Properties
PropertyValueSource
Water Solubility0.0319 mg/mLALOGPS
logP4.08ALOGPS
logP3.84ChemAxon
logS-3.9ALOGPS
pKa (Strongest Basic)9.76ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area12.47 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity98.24 m3·mol-1ChemAxon
Polarizability32.47 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9931
Blood Brain Barrier+0.9381
Caco-2 permeable+0.8108
P-glycoprotein substrateSubstrate0.8147
P-glycoprotein inhibitor IInhibitor0.8147
P-glycoprotein inhibitor IIInhibitor0.8214
Renal organic cation transporterInhibitor0.7883
CYP450 2C9 substrateNon-substrate0.7846
CYP450 2D6 substrateSubstrate0.8919
CYP450 3A4 substrateSubstrate0.7475
CYP450 1A2 substrateInhibitor0.9107
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorInhibitor0.8932
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorNon-inhibitor0.917
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6362
Ames testNon AMES toxic0.9133
CarcinogenicityNon-carcinogens0.8322
BiodegradationNot ready biodegradable0.8461
Rat acute toxicity3.2478 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Strong inhibitor0.5346
hERG inhibition (predictor II)Inhibitor0.6959
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-001i-0090000000-c6d70f4744a166243d9c
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-001i-1290000000-843ca75cae9c06d5a947
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0a4i-3940000000-053eb0b8a655ffc47644
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0a4i-3920000000-1decbf30162661f4429b
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0a4i-4920000000-7a9368d04bc38800e87e
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-05ox-4920000000-e6f843926675f1d98789
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-016r-4910000000-1ea8272c7a2859f70a82
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-014i-4910000000-567d6be4466beea7456e
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-014r-4900000000-ce29d6e3479d635e3995

Taxonomy

Description
This compound belongs to the class of organic compounds known as dibenzoxepines. These are compounds containing a dibenzoxepine moiety, which consists of two benzene connected by an oxazepine ring.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Benzoxepines
Sub Class
Dibenzoxepines
Direct Parent
Dibenzoxepines
Alternative Parents
Alkyl aryl ethers / Benzenoids / Trialkylamines / Oxacyclic compounds / Organopnictogen compounds / Hydrocarbon derivatives
Substituents
Dibenzoxepine / Alkyl aryl ether / Benzenoid / Tertiary aliphatic amine / Tertiary amine / Oxacycle / Ether / Organic nitrogen compound / Organic oxygen compound / Organopnictogen compound
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
tertiary amino compound, dibenzooxepine (CHEBI:4710)

Targets

Details
1. Histamine H1 receptor
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Antagonist
General Function
Histamine receptor activity
Specific Function
In peripheral tissues, the H1 subclass of histamine receptors mediates the contraction of smooth muscles, increase in capillary permeability due to contraction of terminal venules, and catecholamin...
Gene Name
HRH1
Uniprot ID
P35367
Uniprot Name
Histamine H1 receptor
Molecular Weight
55783.61 Da
References
  1. Tashiro M, Sakurada Y, Iwabuchi K, Mochizuki H, Kato M, Aoki M, Funaki Y, Itoh M, Iwata R, Wong DF, Yanai K: Central effects of fexofenadine and cetirizine: measurement of psychomotor performance, subjective sleepiness, and brain histamine H1-receptor occupancy using 11C-doxepin positron emission tomography. J Clin Pharmacol. 2004 Aug;44(8):890-900. [PubMed:15286093]
  2. Tran VT, Lebovitz R, Toll L, Snyder SH: [3H]doxepin interactions with histamine H1-receptors and other sites in guinea pig and rat brain homogenates. Eur J Pharmacol. 1981 Apr 9;70(4):501-9. [PubMed:7238574]
  3. Kano M, Fukudo S, Tashiro A, Utsumi A, Tamura D, Itoh M, Iwata R, Tashiro M, Mochizuki H, Funaki Y, Kato M, Hongo M, Yanai K: Decreased histamine H1 receptor binding in the brain of depressed patients. Eur J Neurosci. 2004 Aug;20(3):803-10. [PubMed:15255990]
  4. Claro E, Arbones L, Garcia A, Picatoste F: Phosphoinositide hydrolysis mediated by histamine H1-receptors in rat brain cortex. Eur J Pharmacol. 1986 Apr 16;123(2):187-96. [PubMed:3011460]
  5. Richelson E, Nelson A: Antagonism by antidepressants of neurotransmitter receptors of normal human brain in vitro. J Pharmacol Exp Ther. 1984 Jul;230(1):94-102. [PubMed:6086881]
  6. Cusack B, Nelson A, Richelson E: Binding of antidepressants to human brain receptors: focus on newer generation compounds. Psychopharmacology (Berl). 1994 May;114(4):559-65. [PubMed:7855217]
  7. Stahl SM: Selective histamine H1 antagonism: novel hypnotic and pharmacologic actions challenge classical notions of antihistamines. CNS Spectr. 2008 Dec;13(12):1027-38. [PubMed:19179941]
  8. Singh H, Becker PM: Novel therapeutic usage of low-dose doxepin hydrochloride. Expert Opin Investig Drugs. 2007 Aug;16(8):1295-305. [PubMed:17685877]
  9. Figueiredo A, Ribeiro CA, Goncalo M, Almeida L, Poiares-Baptista A, Teixeira F: Mechanism of action of doxepin in the treatment of chronic urticaria. Fundam Clin Pharmacol. 1990;4(2):147-58. [PubMed:2141000]
  10. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
Details
2. Histamine H2 receptor
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Antagonist
General Function
Histamine receptor activity
Specific Function
The H2 subclass of histamine receptors mediates gastric acid secretion. Also appears to regulate gastrointestinal motility and intestinal secretion. Possible role in regulating cell growth and diff...
Gene Name
HRH2
Uniprot ID
P25021
Uniprot Name
Histamine H2 receptor
Molecular Weight
40097.65 Da
References
  1. Beil W, Hannemann H, Sewing KF: Interaction of antidepressants and neuroleptics with histamine stimulated parietal cell adenylate cyclase and H+ secretion. Pharmacology. 1988;36(3):198-203. [PubMed:2897127]
  2. Figueiredo A, Ribeiro CA, Goncalo M, Almeida L, Poiares-Baptista A, Teixeira F: Mechanism of action of doxepin in the treatment of chronic urticaria. Fundam Clin Pharmacol. 1990;4(2):147-58. [PubMed:2141000]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inhibitor
General Function
Norepinephrine:sodium symporter activity
Specific Function
Amine transporter. Terminates the action of noradrenaline by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name
SLC6A2
Uniprot ID
P23975
Uniprot Name
Sodium-dependent noradrenaline transporter
Molecular Weight
69331.42 Da
References
  1. Tatsumi M, Groshan K, Blakely RD, Richelson E: Pharmacological profile of antidepressants and related compounds at human monoamine transporters. Eur J Pharmacol. 1997 Dec 11;340(2-3):249-58. [PubMed:9537821]
  2. Stahl SM: Selective histamine H1 antagonism: novel hypnotic and pharmacologic actions challenge classical notions of antihistamines. CNS Spectr. 2008 Dec;13(12):1027-38. [PubMed:19179941]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inhibitor
General Function
Serotonin:sodium symporter activity
Specific Function
Serotonin transporter whose primary function in the central nervous system involves the regulation of serotonergic signaling via transport of serotonin molecules from the synaptic cleft back into t...
Gene Name
SLC6A4
Uniprot ID
P31645
Uniprot Name
Sodium-dependent serotonin transporter
Molecular Weight
70324.165 Da
References
  1. Tatsumi M, Groshan K, Blakely RD, Richelson E: Pharmacological profile of antidepressants and related compounds at human monoamine transporters. Eur J Pharmacol. 1997 Dec 11;340(2-3):249-58. [PubMed:9537821]
  2. Stahl SM: Selective histamine H1 antagonism: novel hypnotic and pharmacologic actions challenge classical notions of antihistamines. CNS Spectr. 2008 Dec;13(12):1027-38. [PubMed:19179941]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Antagonist
General Function
Virus receptor activity
Specific Function
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances, including mescaline, psilocybin, 1-(2,5-dimethoxy-4-iodop...
Gene Name
HTR2A
Uniprot ID
P28223
Uniprot Name
5-hydroxytryptamine receptor 2A
Molecular Weight
52602.58 Da
References
  1. Cusack B, Nelson A, Richelson E: Binding of antidepressants to human brain receptors: focus on newer generation compounds. Psychopharmacology (Berl). 1994 May;114(4):559-65. [PubMed:7855217]
  2. Maj J, Gancarczyk L, Gorszczyk L, Rawlow A: Doxepin as a blocker of central serotonin receptors. Pharmakopsychiatr Neuropsychopharmakol. 1977 Dec;10(6):318-24. [PubMed:309138]
  3. Stahl SM: Selective histamine H1 antagonism: novel hypnotic and pharmacologic actions challenge classical notions of antihistamines. CNS Spectr. 2008 Dec;13(12):1027-38. [PubMed:19179941]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Antagonist
General Function
Serotonin receptor activity
Specific Function
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various ergot alkaloid derivatives and psychoactive substances. Ligand binding causes a conformation...
Gene Name
HTR2B
Uniprot ID
P41595
Uniprot Name
5-hydroxytryptamine receptor 2B
Molecular Weight
54297.41 Da
References
  1. Cusack B, Nelson A, Richelson E: Binding of antidepressants to human brain receptors: focus on newer generation compounds. Psychopharmacology (Berl). 1994 May;114(4):559-65. [PubMed:7855217]
  2. Maj J, Gancarczyk L, Gorszczyk L, Rawlow A: Doxepin as a blocker of central serotonin receptors. Pharmakopsychiatr Neuropsychopharmakol. 1977 Dec;10(6):318-24. [PubMed:309138]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Antagonist
General Function
Serotonin receptor activity
Specific Function
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances, including ergot alkaloid derivatives, 1-2,5,-dimethoxy-4-...
Gene Name
HTR2C
Uniprot ID
P28335
Uniprot Name
5-hydroxytryptamine receptor 2C
Molecular Weight
51820.705 Da
References
  1. Cusack B, Nelson A, Richelson E: Binding of antidepressants to human brain receptors: focus on newer generation compounds. Psychopharmacology (Berl). 1994 May;114(4):559-65. [PubMed:7855217]
  2. Maj J, Gancarczyk L, Gorszczyk L, Rawlow A: Doxepin as a blocker of central serotonin receptors. Pharmakopsychiatr Neuropsychopharmakol. 1977 Dec;10(6):318-24. [PubMed:309138]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Antagonist
General Function
Phosphatidylinositol phospholipase c activity
Specific Function
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the...
Gene Name
CHRM1
Uniprot ID
P11229
Uniprot Name
Muscarinic acetylcholine receptor M1
Molecular Weight
51420.375 Da
References
  1. Cusack B, Nelson A, Richelson E: Binding of antidepressants to human brain receptors: focus on newer generation compounds. Psychopharmacology (Berl). 1994 May;114(4):559-65. [PubMed:7855217]
  2. Stahl SM: Selective histamine H1 antagonism: novel hypnotic and pharmacologic actions challenge classical notions of antihistamines. CNS Spectr. 2008 Dec;13(12):1027-38. [PubMed:19179941]
  3. Ehlert FJ, Delen FM, Yun SH, Liem HA: The interaction of amitriptyline, doxepin, imipramine and their N-methyl quaternary ammonium derivatives with subtypes of muscarinic receptors in brain and heart. J Pharmacol Exp Ther. 1990 Apr;253(1):13-9. [PubMed:2329499]
  4. Figueiredo A, Ribeiro CA, Goncalo M, Almeida L, Poiares-Baptista A, Teixeira F: Mechanism of action of doxepin in the treatment of chronic urticaria. Fundam Clin Pharmacol. 1990;4(2):147-58. [PubMed:2141000]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Antagonist
General Function
G-protein coupled acetylcholine receptor activity
Specific Function
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the...
Gene Name
CHRM2
Uniprot ID
P08172
Uniprot Name
Muscarinic acetylcholine receptor M2
Molecular Weight
51714.605 Da
References
  1. Cusack B, Nelson A, Richelson E: Binding of antidepressants to human brain receptors: focus on newer generation compounds. Psychopharmacology (Berl). 1994 May;114(4):559-65. [PubMed:7855217]
  2. Ehlert FJ, Delen FM, Yun SH, Liem HA: The interaction of amitriptyline, doxepin, imipramine and their N-methyl quaternary ammonium derivatives with subtypes of muscarinic receptors in brain and heart. J Pharmacol Exp Ther. 1990 Apr;253(1):13-9. [PubMed:2329499]
  3. Figueiredo A, Ribeiro CA, Goncalo M, Almeida L, Poiares-Baptista A, Teixeira F: Mechanism of action of doxepin in the treatment of chronic urticaria. Fundam Clin Pharmacol. 1990;4(2):147-58. [PubMed:2141000]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Antagonist
General Function
Receptor activity
Specific Function
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the...
Gene Name
CHRM3
Uniprot ID
P20309
Uniprot Name
Muscarinic acetylcholine receptor M3
Molecular Weight
66127.445 Da
References
  1. Cusack B, Nelson A, Richelson E: Binding of antidepressants to human brain receptors: focus on newer generation compounds. Psychopharmacology (Berl). 1994 May;114(4):559-65. [PubMed:7855217]
  2. Ehlert FJ, Delen FM, Yun SH, Liem HA: The interaction of amitriptyline, doxepin, imipramine and their N-methyl quaternary ammonium derivatives with subtypes of muscarinic receptors in brain and heart. J Pharmacol Exp Ther. 1990 Apr;253(1):13-9. [PubMed:2329499]
  3. Figueiredo A, Ribeiro CA, Goncalo M, Almeida L, Poiares-Baptista A, Teixeira F: Mechanism of action of doxepin in the treatment of chronic urticaria. Fundam Clin Pharmacol. 1990;4(2):147-58. [PubMed:2141000]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Antagonist
General Function
Guanyl-nucleotide exchange factor activity
Specific Function
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the...
Gene Name
CHRM4
Uniprot ID
P08173
Uniprot Name
Muscarinic acetylcholine receptor M4
Molecular Weight
53048.65 Da
References
  1. Cusack B, Nelson A, Richelson E: Binding of antidepressants to human brain receptors: focus on newer generation compounds. Psychopharmacology (Berl). 1994 May;114(4):559-65. [PubMed:7855217]
  2. Ehlert FJ, Delen FM, Yun SH, Liem HA: The interaction of amitriptyline, doxepin, imipramine and their N-methyl quaternary ammonium derivatives with subtypes of muscarinic receptors in brain and heart. J Pharmacol Exp Ther. 1990 Apr;253(1):13-9. [PubMed:2329499]
  3. Figueiredo A, Ribeiro CA, Goncalo M, Almeida L, Poiares-Baptista A, Teixeira F: Mechanism of action of doxepin in the treatment of chronic urticaria. Fundam Clin Pharmacol. 1990;4(2):147-58. [PubMed:2141000]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Antagonist
General Function
Phosphatidylinositol phospholipase c activity
Specific Function
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the...
Gene Name
CHRM5
Uniprot ID
P08912
Uniprot Name
Muscarinic acetylcholine receptor M5
Molecular Weight
60073.205 Da
References
  1. Cusack B, Nelson A, Richelson E: Binding of antidepressants to human brain receptors: focus on newer generation compounds. Psychopharmacology (Berl). 1994 May;114(4):559-65. [PubMed:7855217]
  2. Ehlert FJ, Delen FM, Yun SH, Liem HA: The interaction of amitriptyline, doxepin, imipramine and their N-methyl quaternary ammonium derivatives with subtypes of muscarinic receptors in brain and heart. J Pharmacol Exp Ther. 1990 Apr;253(1):13-9. [PubMed:2329499]
  3. Figueiredo A, Ribeiro CA, Goncalo M, Almeida L, Poiares-Baptista A, Teixeira F: Mechanism of action of doxepin in the treatment of chronic urticaria. Fundam Clin Pharmacol. 1990;4(2):147-58. [PubMed:2141000]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Antagonist
General Function
Protein heterodimerization activity
Specific Function
This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. Its effect is mediated by G(q) and G(11) prot...
Gene Name
ADRA1A
Uniprot ID
P35348
Uniprot Name
Alpha-1A adrenergic receptor
Molecular Weight
51486.005 Da
References
  1. Cusack B, Nelson A, Richelson E: Binding of antidepressants to human brain receptors: focus on newer generation compounds. Psychopharmacology (Berl). 1994 May;114(4):559-65. [PubMed:7855217]
  2. Stahl SM: Selective histamine H1 antagonism: novel hypnotic and pharmacologic actions challenge classical notions of antihistamines. CNS Spectr. 2008 Dec;13(12):1027-38. [PubMed:19179941]
  3. Richelson E, Nelson A: Antagonism by antidepressants of neurotransmitter receptors of normal human brain in vitro. J Pharmacol Exp Ther. 1984 Jul;230(1):94-102. [PubMed:6086881]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Antagonist
General Function
Protein heterodimerization activity
Specific Function
This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. Its effect is mediated by G(q) and G(11) prot...
Gene Name
ADRA1B
Uniprot ID
P35368
Uniprot Name
Alpha-1B adrenergic receptor
Molecular Weight
56835.375 Da
References
  1. Cusack B, Nelson A, Richelson E: Binding of antidepressants to human brain receptors: focus on newer generation compounds. Psychopharmacology (Berl). 1994 May;114(4):559-65. [PubMed:7855217]
  2. Stahl SM: Selective histamine H1 antagonism: novel hypnotic and pharmacologic actions challenge classical notions of antihistamines. CNS Spectr. 2008 Dec;13(12):1027-38. [PubMed:19179941]
  3. Richelson E, Nelson A: Antagonism by antidepressants of neurotransmitter receptors of normal human brain in vitro. J Pharmacol Exp Ther. 1984 Jul;230(1):94-102. [PubMed:6086881]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Antagonist
General Function
Alpha1-adrenergic receptor activity
Specific Function
This alpha-adrenergic receptor mediates its effect through the influx of extracellular calcium.
Gene Name
ADRA1D
Uniprot ID
P25100
Uniprot Name
Alpha-1D adrenergic receptor
Molecular Weight
60462.205 Da
References
  1. Cusack B, Nelson A, Richelson E: Binding of antidepressants to human brain receptors: focus on newer generation compounds. Psychopharmacology (Berl). 1994 May;114(4):559-65. [PubMed:7855217]
  2. Stahl SM: Selective histamine H1 antagonism: novel hypnotic and pharmacologic actions challenge classical notions of antihistamines. CNS Spectr. 2008 Dec;13(12):1027-38. [PubMed:19179941]
  3. Richelson E, Nelson A: Antagonism by antidepressants of neurotransmitter receptors of normal human brain in vitro. J Pharmacol Exp Ther. 1984 Jul;230(1):94-102. [PubMed:6086881]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Antagonist
General Function
Serotonin receptor activity
Specific Function
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances. Ligand binding causes a conformation change that triggers...
Gene Name
HTR1A
Uniprot ID
P08908
Uniprot Name
5-hydroxytryptamine receptor 1A
Molecular Weight
46106.335 Da
References
  1. Cusack B, Nelson A, Richelson E: Binding of antidepressants to human brain receptors: focus on newer generation compounds. Psychopharmacology (Berl). 1994 May;114(4):559-65. [PubMed:7855217]
  2. Maj J, Gancarczyk L, Gorszczyk L, Rawlow A: Doxepin as a blocker of central serotonin receptors. Pharmakopsychiatr Neuropsychopharmakol. 1977 Dec;10(6):318-24. [PubMed:309138]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Antagonist
General Function
Thioesterase binding
Specific Function
Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazo...
Gene Name
ADRA2A
Uniprot ID
P08913
Uniprot Name
Alpha-2A adrenergic receptor
Molecular Weight
48956.275 Da
References
  1. Cusack B, Nelson A, Richelson E: Binding of antidepressants to human brain receptors: focus on newer generation compounds. Psychopharmacology (Berl). 1994 May;114(4):559-65. [PubMed:7855217]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Antagonist
General Function
Epinephrine binding
Specific Function
Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is clonidine...
Gene Name
ADRA2B
Uniprot ID
P18089
Uniprot Name
Alpha-2B adrenergic receptor
Molecular Weight
49565.8 Da
References
  1. Cusack B, Nelson A, Richelson E: Binding of antidepressants to human brain receptors: focus on newer generation compounds. Psychopharmacology (Berl). 1994 May;114(4):559-65. [PubMed:7855217]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Antagonist
General Function
Protein homodimerization activity
Specific Function
Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins.
Gene Name
ADRA2C
Uniprot ID
P18825
Uniprot Name
Alpha-2C adrenergic receptor
Molecular Weight
49521.585 Da
References
  1. Cusack B, Nelson A, Richelson E: Binding of antidepressants to human brain receptors: focus on newer generation compounds. Psychopharmacology (Berl). 1994 May;114(4):559-65. [PubMed:7855217]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Antagonist
General Function
Potassium channel regulator activity
Specific Function
Dopamine receptor whose activity is mediated by G proteins which inhibit adenylyl cyclase.
Gene Name
DRD2
Uniprot ID
P14416
Uniprot Name
D(2) dopamine receptor
Molecular Weight
50618.91 Da
References
  1. Cusack B, Nelson A, Richelson E: Binding of antidepressants to human brain receptors: focus on newer generation compounds. Psychopharmacology (Berl). 1994 May;114(4):559-65. [PubMed:7855217]
  2. Richelson E, Nelson A: Antagonism by antidepressants of neurotransmitter receptors of normal human brain in vitro. J Pharmacol Exp Ther. 1984 Jul;230(1):94-102. [PubMed:6086881]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Binder
General Function
Serotonin receptor activity
Specific Function
This is one of the several different receptors for 5-hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor ...
Gene Name
HTR6
Uniprot ID
P50406
Uniprot Name
5-hydroxytryptamine receptor 6
Molecular Weight
46953.625 Da
References
  1. PDSP Ki Database [Link]
Details
22. Histamine H4 receptor
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Binder
General Function
Histamine receptor activity
Specific Function
The H4 subclass of histamine receptors could mediate the histamine signals in peripheral tissues. Displays a significant level of constitutive activity (spontaneous activity in the absence of agoni...
Gene Name
HRH4
Uniprot ID
Q9H3N8
Uniprot Name
Histamine H4 receptor
Molecular Weight
44495.375 Da
References
  1. PDSP Ki Database [Link]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Voltage-gated potassium channel activity involved in ventricular cardiac muscle cell action potential repolarization
Specific Function
Pore-forming (alpha) subunit of voltage-gated inwardly rectifying potassium channel. Channel properties are modulated by cAMP and subunit assembly. Mediates the rapidly activating component of the ...
Gene Name
KCNH2
Uniprot ID
Q12809
Uniprot Name
Potassium voltage-gated channel subfamily H member 2
Molecular Weight
126653.52 Da
References
  1. Duncan RS, McPate MJ, Ridley JM, Gao Z, James AF, Leishman DJ, Leaney JL, Witchel HJ, Hancox JC: Inhibition of the HERG potassium channel by the tricyclic antidepressant doxepin. Biochem Pharmacol. 2007 Aug 1;74(3):425-37. Epub 2007 May 3. [PubMed:17560554]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. Szewczuk-Boguslawska M, Kiejna A, Beszlej JA, Orzechowska-Juzwenko K, Milejski P: Doxepin inhibits CYP2D6 activity in vivo. Pol J Pharmacol. 2004 Jul-Aug;56(4):491-4. [PubMed:15520506]
  2. Grasmader K, Verwohlt PL, Rietschel M, Dragicevic A, Muller M, Hiemke C, Freymann N, Zobel A, Maier W, Rao ML: Impact of polymorphisms of cytochrome-P450 isoenzymes 2C9, 2C19 and 2D6 on plasma concentrations and clinical effects of antidepressants in a naturalistic clinical setting. Eur J Clin Pharmacol. 2004 Jul;60(5):329-36. Epub 2004 May 28. [PubMed:15168101]
  3. Kirchheiner J, Meineke I, Muller G, Roots I, Brockmoller J: Contributions of CYP2D6, CYP2C9 and CYP2C19 to the biotransformation of E- and Z-doxepin in healthy volunteers. Pharmacogenetics. 2002 Oct;12(7):571-80. [PubMed:12360109]
  4. Haritos VS, Ghabrial H, Ahokas JT, Ching MS: Role of cytochrome P450 2D6 (CYP2D6) in the stereospecific metabolism of E- and Z-doxepin. Pharmacogenetics. 2000 Oct;10(7):591-603. [PubMed:11037801]
  5. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  6. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55930.545 Da
References
  1. Kirchheiner J, Meineke I, Muller G, Roots I, Brockmoller J: Contributions of CYP2D6, CYP2C9 and CYP2C19 to the biotransformation of E- and Z-doxepin in healthy volunteers. Pharmacogenetics. 2002 Oct;12(7):571-80. [PubMed:12360109]
  2. Hartter S, Tybring G, Friedberg T, Weigmann H, Hiemke C: The N-demethylation of the doxepin isomers is mainly catalyzed by the polymorphic CYP2C19. Pharm Res. 2002 Jul;19(7):1034-7. [PubMed:12180536]
  3. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. Kirchheiner J, Meineke I, Muller G, Roots I, Brockmoller J: Contributions of CYP2D6, CYP2C9 and CYP2C19 to the biotransformation of E- and Z-doxepin in healthy volunteers. Pharmacogenetics. 2002 Oct;12(7):571-80. [PubMed:12360109]
  2. Hartter S, Tybring G, Friedberg T, Weigmann H, Hiemke C: The N-demethylation of the doxepin isomers is mainly catalyzed by the polymorphic CYP2C19. Pharm Res. 2002 Jul;19(7):1034-7. [PubMed:12180536]
  3. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
Molecular Weight
58293.76 Da
References
  1. Hartter S, Tybring G, Friedberg T, Weigmann H, Hiemke C: The N-demethylation of the doxepin isomers is mainly catalyzed by the polymorphic CYP2C19. Pharm Res. 2002 Jul;19(7):1034-7. [PubMed:12180536]
  2. Haritos VS, Ghabrial H, Ahokas JT, Ching MS: Role of cytochrome P450 2D6 (CYP2D6) in the stereospecific metabolism of E- and Z-doxepin. Pharmacogenetics. 2000 Oct;10(7):591-603. [PubMed:11037801]
  3. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Hartter S, Tybring G, Friedberg T, Weigmann H, Hiemke C: The N-demethylation of the doxepin isomers is mainly catalyzed by the polymorphic CYP2C19. Pharm Res. 2002 Jul;19(7):1034-7. [PubMed:12180536]

Carriers

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Other/unknown
General Function
Not Available
Specific Function
Functions as transport protein in the blood stream. Binds various ligands in the interior of its beta-barrel domain. Also binds synthetic drugs and influences their distribution and availability in...
Gene Name
ORM1
Uniprot ID
P02763
Uniprot Name
Alpha-1-acid glycoprotein 1
Molecular Weight
23511.38 Da
References
  1. Ferry DG, Caplan NB, Cubeddu LX: Interaction between antidepressants and alpha 1-adrenergic receptor antagonists on the binding to alpha 1-acid glycoprotein. J Pharm Sci. 1986 Feb;75(2):146-9. [PubMed:2870173]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Mahar Doan KM, Humphreys JE, Webster LO, Wring SA, Shampine LJ, Serabjit-Singh CJ, Adkison KK, Polli JW: Passive permeability and P-glycoprotein-mediated efflux differentiate central nervous system (CNS) and non-CNS marketed drugs. J Pharmacol Exp Ther. 2002 Dec;303(3):1029-37. [PubMed:12438524]

Drug created on June 13, 2005 07:24 / Updated on January 23, 2018 12:16