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Identification
NameDoxepin
Accession NumberDB01142  (APRD00398)
Typesmall molecule
Groupsapproved
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
SynonymLanguageCode
CidoxepinNot AvailableNot Available
DoxepinNot AvailableNot Available
SinequanNot AvailableNot Available
ZonalonNot AvailableNot Available
Salts
Name/CAS Structure Properties
Doxepin Hydrochloride
Thumb
  • InChI Key: MHNSPTUQQIYJOT-UHFFFAOYSA-N
  • Monoisotopic Mass: 315.138992038
  • Average Mass: 315.837
DBSALT000059
Brand names
NameCompany
AdapinPennwaIt
AponalPfizer
CuratinNot Available
DoxepineShou Chan
PrudoxinNot Available
QuitaxonLexphar
Silenor Somaxon Pharmaceuticals, Inc.
SinequanPfizer
ZonalonFougera
Brand mixturesNot Available
Categories
CAS number1668-19-5
WeightAverage: 279.3761
Monoisotopic: 279.162314299
Chemical FormulaC19H21NO
InChI KeyODQWQRRAPPTVAG-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[9.4.0.0^{3,8}]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-ylidene}propyl)amine
SMILES
[H]C(CCN(C)C)=C1C2=CC=CC=C2COC2=CC=CC=C12
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassHeterocyclic Compounds
ClassBenzoxepines
SubclassDibenzoxepines
Direct parentDibenzoxepines
Alternative parentsAlkyl Aryl Ethers; Benzene and Substituted Derivatives; Tertiary Amines; Polyamines
Substituentsalkyl aryl ether; benzene; tertiary amine; polyamine; ether; amine; organonitrogen compound
Classification descriptionThis compound belongs to the dibenzoxepines. These are compounds containing a dibenzoxepine moiety, which consists of two benzene connected by an oxazepine ring.
Pharmacology
IndicationDoxepin is used for the treatment of depression and/or anxiety. It can also be used for chronic urticaria and in the management of pain.
PharmacodynamicsDoxepin, 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 actionThe 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.
AbsorptionWell-absorbed from the GI tract. Peak plasma concentrations occur within 2 hours of oral administration.
Volume of distributionNot Available
Protein bindingDoxepin 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.

SubstrateEnzymesProduct
Doxepin
N-desmethyldoxepinDetails
Doxepin
Not Available
Doxepin N-oxideDetails
Doxepin
Not Available
(E)-2-hydroxydoxepinDetails
Doxepin
(Z)-N-desmethyldoxepinDetails
Doxepin
(E)-N-desmethyldoxepinDetails
Doxepin
Not Available
Doxepin-N-oxideDetails
Doxepin
Not Available
(E)-2-O-glucuronyldoxepinDetails
N-desmethyldoxepin
Not Available
Didesmethyl doxepinDetails
Doxepin N-oxide
Not Available
Doxepin N-oxide glucuronideDetails
(E)-2-hydroxydoxepin
Not Available
Hydroxydoxepin glucuronideDetails
N-desmethyldoxepin
Hydroxydesmethyl doxepinDetails
(E)-2-hydroxydoxepin
Not Available
Hydroxydesmethyl doxepinDetails
Hydroxydesmethyl doxepin
Not Available
Hydroxydesmethyl doxepin glucuronideDetails
Route of eliminationNot Available
Half life6 - 24.5 hours
ClearanceNot Available
ToxicityLD50=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
PathwayCategorySMPDB ID
Doxepin Metabolism PathwayDrug metabolismSMP00641
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.9931
Blood Brain Barrier + 0.9381
Caco-2 permeable + 0.8108
P-glycoprotein substrate Substrate 0.8147
P-glycoprotein inhibitor I Inhibitor 0.8147
P-glycoprotein inhibitor II Inhibitor 0.8214
Renal organic cation transporter Inhibitor 0.7883
CYP450 2C9 substrate Non-substrate 0.7846
CYP450 2D6 substrate Substrate 0.8919
CYP450 3A4 substrate Substrate 0.7475
CYP450 1A2 substrate Inhibitor 0.9107
CYP450 2C9 substrate Non-inhibitor 0.9071
CYP450 2D6 substrate Inhibitor 0.8932
CYP450 2C19 substrate Non-inhibitor 0.9026
CYP450 3A4 substrate Non-inhibitor 0.917
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.6362
Ames test Non AMES toxic 0.9133
Carcinogenicity Non-carcinogens 0.8322
Biodegradation Not ready biodegradable 0.8461
Rat acute toxicity 3.2478 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Strong inhibitor 0.5346
hERG inhibition (predictor II) Inhibitor 0.6959
Pharmacoeconomics
Manufacturers
  • Clonmel healthcare ltd
  • Mutual pharmaceutical co inc
  • Mylan pharmaceuticals inc
  • New river pharmaceuticals inc
  • Par pharmaceutical inc
  • Purepac pharmaceutical co
  • Quantum pharmics ltd
  • Sandoz inc
  • Watson laboratories inc
  • Pharmaceutical assoc inc
  • Silarx pharmaceuticals inc
  • Teva pharmaceuticals usa
  • Wockhardt eu operations (swiss) ag
  • Nycomed us inc
  • Pfizer Inc
Packagers
Dosage forms
FormRouteStrength
CapsuleOral10 mg, 25 mg, 50 mg, 75 mg, 100 mg, 150 mg
ConcentrateOral10 mg/mL
CreamTopical5%
TabletOral3 mg, 6 mg
Prices
Unit descriptionCostUnit
Zonalon 5% Cream 45 gm Tube190.13USDtube
Zonalon 5% Cream 30 gm Tube144.29USDtube
Doxepin hcl powder8.88USDg
Doxepin 150 mg capsule3.33USDcapsule
Prudoxin 5% cream3.05USDg
Sinequan 100 mg Capsule1.22USDcapsule
Novo-Doxepin 150 mg Capsule1.18USDcapsule
Sinequan 75 mg Capsule0.93USDcapsule
Zonalon 5% cream0.89USDg
Doxepin HCl 150 mg capsule0.87USDcapsule
Apo-Doxepin 100 mg Capsule0.68USDcapsule
Novo-Doxepin 100 mg Capsule0.68USDcapsule
Sinequan 50 mg Capsule0.64USDcapsule
Doxepin 50 mg capsule0.57USDcapsule
Doxepin HCl 100 mg capsule0.56USDcapsule
Novo-Doxepin 75 mg Capsule0.52USDcapsule
Apo-Doxepin 75 mg Capsule0.52USDcapsule
Doxepin HCl 75 mg capsule0.43USDcapsule
Apo-Doxepin 50 mg Capsule0.36USDcapsule
Novo-Doxepin 50 mg Capsule0.36USDcapsule
Sinequan 25 mg Capsule0.35USDcapsule
Doxepin 10 mg capsule0.32USDcapsule
Sinequan 10 mg Capsule0.28USDcapsule
Doxepin HCl 50 mg capsule0.25USDcapsule
Doxepin HCl 25 mg capsule0.23USDcapsule
Doxepin 75 mg capsule0.21USDcapsule
Doxepin HCl 10 mg capsule0.21USDcapsule
Apo-Doxepin 10 mg Capsule0.2USDcapsule
Apo-Doxepin 25 mg Capsule0.19USDcapsule
Novo-Doxepin 25 mg Capsule0.19USDcapsule
Doxepin 25 mg capsule0.18USDcapsule
Doxepin 100 mg capsule0.14USDcapsule
Doxepin HCl 10 mg/ml Concentrate0.13USDml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point< 25 °CPhysProp
boiling point265 °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 solubility3.19e-02 g/lALOGPS
logP4.08ALOGPS
logP3.84ChemAxon
logS-3.9ALOGPS
pKa (strongest basic)9.76ChemAxon
physiological charge1ChemAxon
hydrogen acceptor count2ChemAxon
hydrogen donor count0ChemAxon
polar surface area12.47ChemAxon
rotatable bond count3ChemAxon
refractivity98.24ChemAxon
polarizability32.47ChemAxon
number of rings3ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterYesChemAxon
Veber's ruleYesChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
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 Reference
  1. Virtanen R, Iisalo E, Irjala K: Protein binding of doxepin and desmethyldoxepin. Acta Pharmacol Toxicol (Copenh). 1982 Aug;51(2):159-64. Pubmed
  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
  3. 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
  4. 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
  5. Sansone RA, Sansone LA: Pain, pain, go away: antidepressants and pain management. Psychiatry (Edgmont). 2008 Dec;5(12):16-9. Pubmed
  6. 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
External Links
ResourceLink
KEGG DrugD07875
KEGG CompoundC06971
ChEBI4710
ChEMBLCHEMBL1628227
Therapeutic Targets DatabaseDAP000177
PharmGKBPA449409
IUPHAR1225
Guide to Pharmacology1225
Drug Product Database1913425
RxListhttp://www.rxlist.com/cgi/generic/doxepin.htm
Drugs.comhttp://www.drugs.com/cdi/doxepin-capsules.html
WikipediaDoxepin
ATC CodesN06AA12
AHFS Codes
  • 84:08.00
  • 28:16.04.28
PDB EntriesNot Available
FDA labelshow(588 KB)
MSDSshow(73.4 KB)
Interactions
Drug Interactions
Drug
AltretamineRisk of severe hypotension
ArtemetherAdditive QTc-prolongation may occur. Concomitant therapy should be avoided.
AtazanavirAtazanavir may increase the effect and toxicity of the tricyclic antidepressant, doxepin, by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of doxepin if atazanavir if initiated, discontinued or dose changed.
ButabarbitalBarbiturates like butabarbital may increase the metabolism of tricyclic antidepressants like doxepin. Monitor for decreased therapeutic effects of tricyclic antidepressants if a barbiturate is initiated/dose increased, or increased effects if a barbiturate is discontinued/dose decreased. The tricyclic antidepressant dosage will likely need to be increased during concomitant barbiturate therapy, and reduced upon barbiturate discontinuation.
ButalbitalBarbiturates such as butalbital may increase the metabolism of tricyclic antidepressants such as doxepin. Monitor for decreased therapeutic effects of tricyclic antidepressants if a barbiturate is initiated/dose increased, or increased effects if a barbiturate is discontinued/dose decreased. The tricyclic antidepressant dosage will likely need to be increased during concomitant barbiturate therapy, and reduced upon barbiturate discontinuation.
CarbamazepineCarbamazepine may decrease the serum concentration of the tricyclic antidepressant, doxepin, by increasing its metabolism. Monitor for changes in the therapeutic and adverse effects of doxepin if carbamazepine is initiated, discontinued or dose changed.
CimetidineCimetidine may increase the effect of the tricyclic antidepressant, doxepin, by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of doxepin if cimetidine is initiated, discontinued or dose changed.
CisaprideIncreased risk of cardiotoxicity and arrhythmias
ClonidineThe tricyclic antidepressant, doxepin, decreases the effect of clonidine.
DesvenlafaxineIncreased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Dihydroquinidine barbiturateDihydroquinidine barbiturate increases the effect of the tricyclic antidepressant, doxepin.
DobutamineThe tricyclic antidepressant, doxepin, increases the sympathomimetic effect of dobutamine.
DonepezilPossible antagonism of action
DopamineThe tricyclic antidepressant, doxepin, increases the sympathomimetic effect of dopamine.
EphedraThe tricyclic antidepressant, doxepin, increases the sympathomimetic effect of ephedra.
EphedrineThe tricyclic antidepressant, doxepin, increases the sympathomimetic effect of ephedrine.
EpinephrineThe tricyclic antidepressant, doxepin, increases the sympathomimetic effect of epinephrine.
FenoterolThe tricyclic antidepressant, doxepin, increases the sympathomimetic effect of fenoterol.
FluoxetineThe SSRI, fluoxetine, may increase the serum concentration of the tricyclic antidepressant, doxepin, by decreasing its metabolism. Additive modulation of serotonin activity also increases the risk of serotonin syndrome. Monitor for development of serotonin syndrome during concomitant therapy. Monitor for changes in the therapeutic and adverse effects of doxepin if fluoxetine is initiated, discontinued or dose changed.
FluvoxamineThe SSRI, fluvoxamine, may increase the serum concentration of the tricyclic antidepressant, doxepin, by decreasing its metabolism. Additive modulation of serotonin activity also increases the risk of serotonin syndrome. Monitor for development of serotonin syndrome during concomitant therapy. Monitor for changes in the therapeutic and adverse effects of doxepin if fluvoxamine is initiated, discontinued or dose changed.
GalantaminePossible antagonism of action
GrepafloxacinIncreased risk of cardiotoxicity and arrhythmias
GuanethidineThe tricyclic antidepressant, doxepin, decreases the effect of guanethidine.
IsocarboxazidPossibility of severe adverse effects
IsoprenalineThe tricyclic antidepressant, doxepin, increases the sympathomimetic effect of isoproterenol.
LumefantrineAdditive QTc-prolongation may occur. Concomitant therapy should be avoided.
MephentermineThe tricyclic antidepressant, doxepin, increases the sympathomimetic effect of mephentermine.
MesoridazineIncreased risk of cardiotoxicity and arrhythmias
MetaraminolThe tricyclic antidepressant, doxepin, increases the sympathomimetic effect of metaraminol.
MethoxamineThe tricyclic antidepressant, doxepin, increases the sympathomimetic effect of methoxamine.
MoclobemidePossible severe adverse reaction with this combination
NorepinephrineThe tricyclic antidepressant, doxepin, increases the sympathomimetic effect of norepinephrine.
OrciprenalineThe tricyclic antidepressant, doxepin, increases the sympathomimetic effect of orciprenaline.
PhenelzinePossibility of severe adverse effects
PhenylephrineThe tricyclic antidepressant, doxepin, increases the sympathomimetic effect of phenylephrine.
PhenylpropanolamineThe tricyclic antidepressant, doxepin, increases the sympathomimetic effect of phenylpropanolamine.
PirbuterolThe tricyclic antidepressant, doxepin, increases the sympathomimetic effect of pirbuterol.
ProcaterolThe tricyclic antidepressant, doxepin, increases the sympathomimetic effect of procaterol.
PseudoephedrineThe tricyclic antidepressant, doxepin, increases the sympathomimetic effect of pseudoephedrine.
QuinidineAdditive QTc-prolonging effects may occur. Quinidine may also increase the serum concentration of the tricyclic antidepressant, doxepin, by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of doxepin if quinidine is initiated, discontinued or dose changed. Monitor for the development of torsades de pointes during concomitant therapy.
Quinidine barbiturateQuinidine barbiturate increases the effect of tricyclic antidepressant, doxepin.
RasagilinePossibility of severe adverse effects
RifabutinThe rifamycin, rifabutin, may decrease the effect of the tricyclic antidepressant, doxepin, by increasing its metabolism. Monitor for changes in the therapeutic and adverse effects of doxepin if rifabutin is initiated, discontinued or dose changed.
RifampicinThe rifamycin, rifampin, may decrease the effect of the tricyclic antidepressant, doxepin, by increasing its metabolism. Monitor for changes in the therapeutic and adverse effects of doxepin if rifampin is initiated, discontinued or dose changed.
RitonavirRitonavir may increase the effect and toxicity of the tricyclic antidepressant, doxepin, by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of doxepin if ritonavir if initiated, discontinued or dose changed.
RivastigminePossible antagonism of action
SalbutamolThe tricyclic antidepressant, doxepin, increases the sympathomimetic effect of salbutamol.
SibutramineIncreased risk of CNS adverse effects
SparfloxacinIncreased risk of cardiotoxicity and arrhythmias
TacrineThe therapeutic effects of the central acetylcholinesterase inhibitor, Tacrine, and/or the anticholinergic, Doxepin, may be reduced due to antagonism. The interaction may be beneficial when the anticholinergic action is a side effect. Monitor for decreased efficacy of both agents.
TacrolimusAdditive QTc-prolongation may occur increasing the risk of serious ventricular arrhythmias. Concomitant therapy should be used with caution.
TelithromycinTelithromycin may reduce clearance of Doxepin. Consider alternate therapy or monitor for changes in the therapeutic/adverse effects of Doxepin if Telithromycin is initiated, discontinued or dose changed.
TerbinafineTerbinafine may reduce the metabolism and clearance of Doxepin. Consider alternate therapy or monitor for therapeutic/adverse effects of Amytriptyline if Doxepin is initiated, discontinued or dose changed.
TerbutalineThe tricyclic antidepressant, doxepin, increases the sympathomimetic effect of terbutaline.
TerfenadineIncreased risk of cardiotoxicity and arrhythmias
ThiabendazoleThe strong CYP1A2 inhibitor, Thiabendazole, may increase the effects and toxicity of Doxepin by decreasing Doxepin metabolism and clearance. Monitor for changes in the therapeutic and adverse effects of Doxepin if Thiabendazole is initiated, discontinued or dose changed.
ThioridazineIncreased risk of cardiotoxicity and arrhythmias
ThiothixeneMay cause additive QTc-prolonging effects. Increased risk of ventricular arrhythmias. Consider alternate therapy. Thorough risk:benefit assessment is required prior to co-administration.
ToremifeneAdditive QTc-prolongation may occur, increasing the risk of serious ventricular arrhythmias. Consider alternate therapy. A thorough risk:benefit assessment is required prior to co-administration.
TramadolTramadol increases the risk of serotonin syndrome and seizures.
TranylcypromineIncreased risk of serotonin syndrome. Concomitant therapy should be avoided. A significant washout period, dependent on the half-lives of the agents, should be employed between therapies.
TrazodoneIncreased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
TrimethobenzamideTrimethobenzamide and Doxepin, two anticholinergics, may cause additive anticholinergic effects and enhance their adverse/toxic effects. Monitor for enhanced anticholinergic effects.
TrimipramineIncreased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome. Additive QTc-prolongation may also occur, increasing the risk of serious ventricular arrhythmias. Concomitant therapy should be used with caution.
TriprolidineTriprolidine and Doxepin, two anticholinergics, may cause additive anticholinergic effects and enhance their adverse/toxic effects. Additive CNS depressant effects may also occur. Monitor for enhanced anticholinergic and CNS depressant effects.
TrospiumTrospium and Doxepin, two anticholinergics, may cause additive anticholinergic effects and enhanced adverse/toxic effects. Monitor for enhanced anticholinergic effects.
VenlafaxineIncreased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
VoriconazoleAdditive QTc prolongation may occur. Voriconazole, a strong CYP3A4 inhibitor, may also increase the serum concentration of doxepin by decreasing its metabolism. Consider alternate therapy or monitor for QTc prolongation and changes in the therapeutic and adverse effects of doxepin if voriconazole is initiated, discontinued or dose changed.
VorinostatAdditive QTc prolongation may occur. Consider alternate therapy or monitor for QTc prolongation as this can lead to Torsade de Pointes (TdP).
ZiprasidoneAdditive QTc-prolonging effects may increase the risk of severe arrhythmias. Concomitant therapy is contraindicated.
ZolmitriptanUse of two serotonin modulators, such as zolmitriptan and doxepin, increases the risk of serotonin syndrome. Consider alternate therapy or monitor for serotonin syndrome during concomitant therapy.
ZuclopenthixolAdditive QTc prolongation may occur. Consider alternate therapy or use caution and monitor for QTc prolongation as this can lead to Torsade de Pointes (TdP).
Zuclopenthixol acetateAdditive QTc prolongation may occur. Consider alternate therapy or use caution and monitor for QTc prolongation as this can lead to Torsade de Pointes (TdP).
Zuclopenthixol decanoateAdditive QTc prolongation may occur. Consider alternate therapy or use caution and monitor for QTc prolongation as this can lead to Torsade de Pointes (TdP).
Food Interactions
  • Avoid alcohol.
  • Avoid excessive quantities of coffee or tea (caffeine).
  • Avoid St.John's Wort.
  • Take with food to reduce irritation.

Targets

1. Histamine H1 receptor

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
Histamine H1 receptor P35367 Details

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
  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
  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
  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
  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
  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
  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
  8. Singh H, Becker PM: Novel therapeutic usage of low-dose doxepin hydrochloride. Expert Opin Investig Drugs. 2007 Aug;16(8):1295-305. Pubmed
  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
  10. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

2. Histamine H2 receptor

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
Histamine H2 receptor P25021 Details

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
  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

3. Sodium-dependent noradrenaline transporter

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Sodium-dependent noradrenaline transporter P23975 Details

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
  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

4. Sodium-dependent serotonin transporter

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Sodium-dependent serotonin transporter P31645 Details

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
  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

5. 5-hydroxytryptamine receptor 2A

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
5-hydroxytryptamine receptor 2A P28223 Details

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
  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
  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

6. 5-hydroxytryptamine receptor 2B

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
5-hydroxytryptamine receptor 2B P41595 Details

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
  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

7. 5-hydroxytryptamine receptor 2C

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
5-hydroxytryptamine receptor 2C P28335 Details

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
  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

8. Muscarinic acetylcholine receptor M1

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
Muscarinic acetylcholine receptor M1 P11229 Details

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
  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
  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
  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

9. Muscarinic acetylcholine receptor M2

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
Muscarinic acetylcholine receptor M2 P08172 Details

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
  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
  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

10. Muscarinic acetylcholine receptor M3

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
Muscarinic acetylcholine receptor M3 P20309 Details

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
  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
  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

11. Muscarinic acetylcholine receptor M4

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
Muscarinic acetylcholine receptor M4 P08173 Details

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
  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
  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

12. Muscarinic acetylcholine receptor M5

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
Muscarinic acetylcholine receptor M5 P08912 Details

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
  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
  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

13. Alpha-1A adrenergic receptor

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: antagonist

Components

Name UniProt ID Details
Alpha-1A adrenergic receptor P35348 Details

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
  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
  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

14. Alpha-1B adrenergic receptor

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: antagonist

Components

Name UniProt ID Details
Alpha-1B adrenergic receptor P35368 Details

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
  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
  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

15. Alpha-1D adrenergic receptor

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: antagonist

Components

Name UniProt ID Details
Alpha-1D adrenergic receptor P25100 Details

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
  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
  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

16. 5-hydroxytryptamine receptor 1A

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
5-hydroxytryptamine receptor 1A P08908 Details

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
  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

17. Alpha-2A adrenergic receptor

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: antagonist

Components

Name UniProt ID Details
Alpha-2A adrenergic receptor P08913 Details

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

18. Alpha-2B adrenergic receptor

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: antagonist

Components

Name UniProt ID Details
Alpha-2B adrenergic receptor P18089 Details

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

19. Alpha-2C adrenergic receptor

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: antagonist

Components

Name UniProt ID Details
Alpha-2C adrenergic receptor P18825 Details

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

20. D(2) dopamine receptor

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: antagonist

Components

Name UniProt ID Details
D(2) dopamine receptor P14416 Details

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
  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

21. 5-hydroxytryptamine receptor 6

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: binder

Components

Name UniProt ID Details
5-hydroxytryptamine receptor 6 P50406 Details

References:

  1. Roth, BL; Driscol, J (12 January 2011). PDSP Ki Database. Psychoactive Drug Screening Program (PDSP). University of North Carolina at Chapel Hill and the United States National Institute of Mental Health. Retrieved 20 October 2013.

22. Histamine H4 receptor

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: binder

Components

Name UniProt ID Details
Histamine H4 receptor Q9H3N8 Details

References:

  1. Roth, BL; Driscol, J (12 January 2011). PDSP Ki Database. Psychoactive Drug Screening Program (PDSP). University of North Carolina at Chapel Hill and the United States National Institute of Mental Health. Retrieved 20 October 2013.

23. Potassium voltage-gated channel subfamily H member 2

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Potassium voltage-gated channel subfamily H member 2 Q12809 Details

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

Enzymes

1. Cytochrome P450 2D6

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor

Components

Name UniProt ID Details
Cytochrome P450 2D6 P10635 Details

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
  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
  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
  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
  5. Flockhart DA. Drug Interactions: Cytochrome P450 Drug Interaction Table. Indiana University School of Medicine (2007). Accessed May 28, 2010.
  6. 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. Epub 2009 Nov 24. Pubmed

2. Cytochrome P450 2C19

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 2C19 P33261 Details

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
  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
  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. Epub 2009 Nov 24. Pubmed

3. Cytochrome P450 2C9

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 2C9 P11712 Details

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
  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
  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. Epub 2009 Nov 24. Pubmed

4. Cytochrome P450 1A2

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 1A2 P05177 Details

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
  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
  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. Epub 2009 Nov 24. Pubmed

5. Cytochrome P450 3A4

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 3A4 P08684 Details

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

Carriers

1. Alpha-1-acid glycoprotein 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: other/unknown

Components

Name UniProt ID Details
Alpha-1-acid glycoprotein 1 P02763 Details

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

Transporters

1. Multidrug resistance protein 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Multidrug resistance protein 1 P08183 Details

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

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:13