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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
Cidoxepin
Doxepin
Sinequan
Zonalon
External Identifiers Not Available
Approved 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
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
Novo-doxepincapsule150 mgoralTeva Canada Limited1992-12-31Not applicableCanada
Novo-doxepincapsule100 mgoralTeva Canada Limited1992-12-31Not applicableCanada
Novo-doxepincapsule75 mgoralTeva Canada Limited1992-12-31Not applicableCanada
Novo-doxepincapsule50 mgoralTeva Canada Limited1992-12-31Not applicableCanada
Novo-doxepincapsule25 mgoralTeva Canada Limited1992-12-31Not applicableCanada
Ntp-doxepincapsule100 mgoralTeva Canada LimitedNot applicableNot applicableCanada
Ntp-doxepincapsule75 mgoralTeva Canada LimitedNot applicableNot applicableCanada
Ntp-doxepincapsule50 mgoralTeva Canada LimitedNot applicableNot applicableCanada
Ntp-doxepincapsule25 mgoralTeva Canada LimitedNot applicableNot applicableCanada
Prudoxincream50 mg/gtopicalHEALTHPOINT, LTD2001-10-012015-11-30Us
Prudoxincream50 mg/gtopicalPrestium Pharma, Inc.2015-06-01Not applicableUs
Prudoxincream50 mg/gtopicalSmith & Nephew, Inc.2012-12-212015-11-30Us
Rho-doxepin - Cap 25mgcapsule25 mgoralRhodiapharm Inc1995-12-311998-08-05Canada
Rho-doxepin - Cap 50mgcapsule50 mgoralRhodiapharm Inc1995-12-311998-08-05Canada
Rho-doxepin-10 Mg Capcapsule10 mgoralRhodiapharm Inc1995-12-311998-08-05Canada
Silenortablet3.00 mgoralPaladin Labs Inc2013-01-08Not applicableCanada
Silenortablet6 mg/1oralPernix Therapeutics, LLC2010-08-01Not applicableUs
Silenortablet3 mg/1oralPernix Therapeutics, LLC2010-08-01Not applicableUs
Silenortablet6.00 mgoralPaladin Labs Inc2013-01-08Not applicableCanada
Sinequan Cap 100mgcapsule100 mgoralErfa Canada 2012 Inc1975-12-312015-06-05Canada
Sinequan Cap 10mgcapsule10 mgoralErfa Canada 2012 Inc1970-12-31Not applicableCanada
Sinequan Cap 150mgcapsule150 mgoralPfizer Canada Inc1983-12-312000-07-26Canada
Sinequan Cap 25mgcapsule25 mgoralErfa Canada 2012 Inc1970-12-31Not applicableCanada
Sinequan Cap 50mgcapsule50 mgoralErfa Canada 2012 Inc1970-12-31Not applicableCanada
Sinequan Cap 75mgcapsule75 mgoralErfa Canada 2012 Inc1977-12-312015-06-05Canada
Triadapin Cap 100mgcapsule100 mgoralAventis Pharma Inc1985-12-312002-07-29Canada
Triadapin Cap 10mgcapsule10 mgoralAventis Pharma Inc1985-12-312001-07-20Canada
Triadapin Cap 25mgcapsule25 mgoralAventis Pharma Inc1985-12-312001-07-20Canada
Triadapin Cap 50mgcapsule50 mgoralAventis Pharma Inc1985-12-312002-07-29Canada
Triadapin Cap 75mgcapsule75 mgoralAventis Pharma Inc1985-12-312002-07-29Canada
Zonaloncream50 mg/gtopicalPharma Derm A Division Of Fougera Pharmaceuticals Inc.1994-04-01Not applicableUs
Zonaloncream50 mg/gtopicalPrestium Pharma, Inc.2015-03-12Not applicableUs
Zonaloncream50 mg/gtopicalLake Erie Medical & Surgical Supply DBA Quality Care Products LLC2012-03-30Not applicableUs
Zonalon Cream 5%cream5 %topicalValeant Canada Lp/valeant Canada s.e.c.1995-12-312016-07-08Canada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-doxepincapsule50 mgoralApotex Inc1993-12-31Not applicableCanada
Apo-doxepincapsule10 mgoralApotex Inc1993-12-31Not applicableCanada
Apo-doxepincapsule25 mgoralApotex Inc1993-12-31Not applicableCanada
Apo-doxepincapsule150 mgoralApotex Inc1993-12-31Not applicableCanada
Apo-doxepincapsule100 mgoralApotex Inc1993-12-31Not applicableCanada
Apo-doxepincapsule75 mgoralApotex Inc1993-12-31Not applicableCanada
Doxepin Hydrochloridecapsule25 mg/1oralPd Rx Pharmaceuticals, Inc.2011-05-04Not applicableUs
Doxepin Hydrochloridecapsule150 mg/1oralAv Kare, Inc.2012-08-31Not applicableUs
Doxepin Hydrochloridecapsule50 mg/1oralMylan Institutional Inc.1998-10-01Not applicableUs
Doxepin Hydrochloridecapsule50 mg/1oralH.J. Harkins Company, Inc.2011-05-04Not applicableUs
Doxepin Hydrochloridecapsule150 mg/1oralREMEDYREPACK INC.2015-08-03Not applicableUs
Doxepin Hydrochloridesolution, concentrate10 mg/mLoralTeva Pharmaceuticals USA Inc1987-11-06Not applicableUs
Doxepin Hydrochloridecapsule25 mg/1oralPd Rx Pharmaceuticals, Inc.2010-01-01Not applicableUs
Doxepin Hydrochloridecapsule100 mg/1oralPhysicians Total Care, Inc.1996-10-03Not applicableUs
Doxepin Hydrochloridecapsule75 mg/1oralTYA Pharmaceuticals1986-05-13Not applicableUs
Doxepin Hydrochloridecapsule50 mg/1oralSTAT Rx USA LLC2011-05-04Not applicableUs
Doxepin Hydrochloridecapsule25 mg/1oralREMEDYREPACK INC.2010-12-23Not applicableUs
Doxepin Hydrochloridecapsule75 mg/1oralPd Rx Pharmaceuticals, Inc.2011-05-04Not applicableUs
Doxepin Hydrochloridecapsule10 mg/1oralLake Erie Medical & Surgical Supply DBA Quality Care Products LLC2012-04-03Not applicableUs
Doxepin Hydrochloridecapsule25 mg/1oralMylan Institutional Inc.1998-10-01Not applicableUs
Doxepin Hydrochloridecapsule50 mg/1oralPhysicians Total Care, Inc.1999-09-28Not applicableUs
Doxepin Hydrochloridecapsule25 mg/1oralbryant ranch prepack2012-10-18Not applicableUs
Doxepin Hydrochloridecapsule100 mg/1oralMylan Pharmaceuticals Inc.1986-05-13Not applicableUs
Doxepin Hydrochloridecapsule100 mg/1oralREMEDYREPACK INC.2010-12-23Not applicableUs
Doxepin Hydrochloridecapsule50 mg/1oralPd Rx Pharmaceuticals, Inc.2011-05-04Not applicableUs
Doxepin Hydrochloridecapsule50 mg/1oralREMEDYREPACK INC.2010-12-17Not applicableUs
Doxepin Hydrochloridecapsule10 mg/1oralMylan Institutional Inc.1998-10-01Not applicableUs
Doxepin Hydrochloridecapsule25 mg/1oralPhysicians Total Care, Inc.1996-04-24Not applicableUs
Doxepin Hydrochloridecapsule10 mg/1oralbryant ranch prepack2012-10-18Not applicableUs
Doxepin Hydrochloridecapsule75 mg/1oralMylan Pharmaceuticals Inc.1986-05-13Not applicableUs
Doxepin Hydrochloridecapsule25 mg/1oralREMEDYREPACK INC.2010-12-07Not applicableUs
Doxepin Hydrochloridecapsule50 mg/1oralRebel Distributors Corp1986-05-13Not applicableUs
Doxepin Hydrochloridecapsule50 mg/1oralUnit Dose Services2011-05-04Not applicableUs
Doxepin Hydrochloridecapsule25 mg/1oralCardinal Health2011-08-18Not applicableUs
Doxepin Hydrochloridecapsule50 mg/1oralMylan Pharmaceuticals Inc.1986-05-13Not applicableUs
Doxepin Hydrochloridecapsule75 mg/1oralREMEDYREPACK INC.2010-12-02Not applicableUs
Doxepin Hydrochloridesolution10 mg/mLoralSilarx Pharmaceuticals, Inc1998-12-29Not applicableUs
Doxepin Hydrochloridecapsule50 mg/1oralbryant ranch prepack2011-05-04Not applicableUs
Doxepin Hydrochloridecapsule10 mg/1oralRebel Distributors Corp1986-05-13Not applicableUs
Doxepin Hydrochloridecapsule50 mg/1oralLake Erie Medical & Surgical Supply DBA Quality Care Products LLC2012-03-05Not applicableUs
Doxepin Hydrochloridecapsule150 mg/1oralPhysicians Total Care, Inc.2007-08-01Not applicableUs
Doxepin Hydrochloridecapsule100 mg/1oralContract Pharmacy Services Pa2010-04-06Not applicableUs
Doxepin Hydrochloridecapsule25 mg/1oralMylan Pharmaceuticals Inc.1986-05-13Not applicableUs
Doxepin Hydrochloridecapsule100 mg/1oralMedsource Pharmaceuticals1986-05-13Not applicableUs
Doxepin Hydrochloridecapsule50 mg/1oralA S Medication Solutions Llc2012-10-18Not applicableUs
Doxepin Hydrochloridecapsule25 mg/1oralDIRECT RX2014-01-01Not applicableUs
Doxepin Hydrochloridecapsule75 mg/1oralPhysicians Total Care, Inc.2003-06-10Not applicableUs
Doxepin Hydrochloridecapsule75 mg/1oralContract Pharmacy Services Pa2010-04-06Not applicableUs
Doxepin Hydrochloridecapsule100 mg/1oralSTAT Rx USA LLC2011-05-04Not applicableUs
Doxepin Hydrochloridecapsule150 mg/1oralPar Pharmaceutical Inc1987-11-09Not applicableUs
Doxepin Hydrochloridesolution10 mg/mLoralMorton Grove Pharmaceuticals, Inc.1995-02-09Not applicableUs
Doxepin Hydrochloridecapsule150 mg/1oralSTAT Rx USA LLC1987-11-09Not applicableUs
Doxepin Hydrochloridecapsule100 mg/1oralMylan Institutional Inc.1998-10-01Not applicableUs
Doxepin Hydrochloridecapsule10 mg/1oralAidarex Pharmaceuticals LLC2012-10-18Not applicableUs
Doxepin Hydrochloridecapsule50 mg/1oralDIRECT RX2014-01-01Not applicableUs
Doxepin Hydrochloridesolution10 mg/mLoralCarilion Materials Management1998-12-29Not applicableUs
Doxepin Hydrochloridecapsule10 mg/1oralMylan Pharmaceuticals Inc.1986-05-13Not applicableUs
Doxepin Hydrochloridecapsule10 mg/1oralMedsource Pharmaceuticals1986-05-13Not applicableUs
Doxepin Hydrochloridecapsule10 mg/1oralPhysicians Total Care, Inc.1995-01-03Not applicableUs
Doxepin Hydrochloridecapsule50 mg/1oralContract Pharmacy Services Pa2010-04-06Not applicableUs
Doxepin Hydrochloridecapsule10 mg/1oralSTAT Rx USA LLC2011-05-04Not applicableUs
Doxepin Hydrochloridecapsule10 mg/1oralREMEDYREPACK INC.2012-01-17Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
AdapinPennwaIt
AponalPfizer
CuratinNot Available
DoxepineShou Chan
QuitaxonLexphar
SinequanPfizer
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Doxepin Hydrochloride
Thumb
  • InChI Key: MHNSPTUQQIYJOT-UHFFFAOYSA-N
  • Monoisotopic Mass: 315.138992038
  • Average Mass: 315.837
DBSALT000059
Categories
UNII5ASJ6HUZ7D
CAS number1668-19-5
WeightAverage: 279.3761
Monoisotopic: 279.162314299
Chemical FormulaC19H21NO
InChI KeyInChIKey=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
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzoxepines
Sub ClassDibenzoxepines
Direct ParentDibenzoxepines
Alternative Parents
Substituents
  • Dibenzoxepine
  • Alkyl aryl ether
  • Benzenoid
  • Tertiary aliphatic amine
  • Tertiary amine
  • Oxacycle
  • Ether
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
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.
Related Articles
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
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 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Capsuleoral10 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
Capsuleoral100 mg
Capsuleoral150 mg
Capsuleoral25 mg
Capsuleoral50 mg
Capsuleoral75 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)
US6211229 No2000-02-172020-02-17Us
US7915307 No2007-08-242027-08-24Us
US8513299 No2010-04-142030-04-14Us
US9107898 No2008-05-012028-05-01Us
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 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 RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
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 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
ATC CodesN06AA12
AHFS Codes
  • 28:16.04.28
  • 84:08.00
PDB EntriesNot Available
FDA labelDownload (588 KB)
MSDSDownload (73.4 KB)
Interactions
Drug Interactions
Drug
AbirateroneThe serum concentration of Doxepin can be increased when it is combined with Abiraterone.
AcepromazineThe risk or severity of adverse effects can be increased when Doxepin is combined with Acepromazine.
AcetophenazineThe risk or severity of adverse effects can be increased when Doxepin is combined with Acetophenazine.
Acetylsalicylic acidDoxepin may increase the antiplatelet activities of Acetylsalicylic acid.
AclidiniumAclidinium may increase the anticholinergic activities of Doxepin.
AltretamineAltretamine may increase the orthostatic hypotensive activities of Doxepin.
AmisulprideThe risk or severity of adverse effects can be increased when Doxepin is combined with Amisulpride.
AmphetamineDoxepin may increase the stimulatory activities of Amphetamine.
AripiprazoleThe risk or severity of adverse effects can be increased when Doxepin is combined with Aripiprazole.
AzelastineDoxepin may increase the central nervous system depressant (CNS depressant) activities of Azelastine.
BaclofenThe risk or severity of adverse effects can be increased when Baclofen is combined with Doxepin.
BatimastatThe serum concentration of Doxepin can be increased when it is combined with Batimastat.
BenzquinamideThe risk or severity of adverse effects can be increased when Doxepin is combined with Benzquinamide.
Botulinum Toxin Type ADoxepin may increase the anticholinergic activities of Botulinum Toxin Type A.
Botulinum Toxin Type BDoxepin may increase the anticholinergic activities of Botulinum Toxin Type B.
BrimonidineBrimonidine may increase the central nervous system depressant (CNS depressant) activities of Doxepin.
BuprenorphineDoxepin may increase the central nervous system depressant (CNS depressant) activities of Buprenorphine.
BupropionThe metabolism of Doxepin can be decreased when combined with Bupropion.
ButabarbitalThe metabolism of Doxepin can be increased when combined with Butabarbital.
ButethalThe metabolism of Doxepin can be increased when combined with Butethal.
CarbamazepineThe metabolism of Doxepin can be increased when combined with Carbamazepine.
CarphenazineThe risk or severity of adverse effects can be increased when Doxepin is combined with Carphenazine.
CathinoneDoxepin may increase the stimulatory activities of Cathinone.
ChlormezanoneThe risk or severity of adverse effects can be increased when Doxepin is combined with Chlormezanone.
ChlorpromazineThe risk or severity of adverse effects can be increased when Doxepin is combined with Chlorpromazine.
ChlorpropamideDoxepin may increase the hypoglycemic activities of Chlorpropamide.
ChlorprothixeneThe risk or severity of adverse effects can be increased when Doxepin is combined with Chlorprothixene.
CimetidineThe metabolism of Doxepin can be decreased when combined with Cimetidine.
CimetropiumDoxepin may increase the anticholinergic activities of Cimetropium Bromide.
CinacalcetThe serum concentration of Doxepin can be increased when it is combined with Cinacalcet.
CitalopramThe risk or severity of adverse effects can be increased when Doxepin is combined with Citalopram.
ClozapineThe risk or severity of adverse effects can be increased when Doxepin is combined with Clozapine.
CobicistatThe serum concentration of Doxepin can be increased when it is combined with Cobicistat.
DapoxetineThe risk or severity of adverse effects can be increased when Dapoxetine is combined with Doxepin.
DarunavirThe serum concentration of Doxepin can be increased when it is combined with Darunavir.
DesmopressinThe risk or severity of adverse effects can be increased when Doxepin is combined with Desmopressin.
DexmethylphenidateThe risk or severity of adverse effects can be increased when Dexmethylphenidate is combined with Doxepin.
DicoumarolDoxepin may increase the anticoagulant activities of Dicoumarol.
DipivefrinThe therapeutic efficacy of Dipivefrin can be decreased when used in combination with Doxepin.
DofetilideDoxepin may increase the QTc-prolonging activities of Dofetilide.
DoxylamineDoxylamine may increase the central nervous system depressant (CNS depressant) activities of Doxepin.
DronabinolDronabinol may increase the central nervous system depressant (CNS depressant) activities of Doxepin.
DroperidolDroperidol may increase the central nervous system depressant (CNS depressant) activities of Doxepin.
DuloxetineDuloxetine may increase the serotonergic activities of Doxepin.
EluxadolineDoxepin may increase the activities of Eluxadoline.
EscitalopramThe risk or severity of adverse effects can be increased when Doxepin is combined with Escitalopram.
EthanolDoxepin may increase the central nervous system depressant (CNS depressant) activities of Ethanol.
FencamfamineThe risk or severity of adverse effects can be increased when Doxepin is combined with Fencamfamine.
FluoxetineThe risk or severity of adverse effects can be increased when Fluoxetine is combined with Doxepin.
FlupentixolThe risk or severity of adverse effects can be increased when Doxepin is combined with Flupentixol.
FluphenazineThe risk or severity of adverse effects can be increased when Doxepin is combined with Fluphenazine.
FluspirileneThe risk or severity of adverse effects can be increased when Doxepin is combined with Fluspirilene.
FluvoxamineThe risk or severity of adverse effects can be increased when Fluvoxamine is combined with Doxepin.
Glucagon recombinantThe risk or severity of adverse effects can be increased when Doxepin is combined with Glucagon recombinant.
GoserelinDoxepin may increase the QTc-prolonging activities of Goserelin.
GranisetronGranisetron may increase the serotonergic activities of Doxepin.
HaloperidolThe risk or severity of adverse effects can be increased when Doxepin is combined with Haloperidol.
HeptabarbitalThe metabolism of Doxepin can be increased when combined with Heptabarbital.
HexobarbitalThe metabolism of Doxepin can be increased when combined with Hexobarbital.
HydrocodoneDoxepin may increase the central nervous system depressant (CNS depressant) activities of Hydrocodone.
HydroxyzineHydroxyzine may increase the central nervous system depressant (CNS depressant) activities of Doxepin.
IcosapentDoxepin may increase the antiplatelet activities of Icosapent.
IobenguaneThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Doxepin.
Ipratropium bromideIpratropium bromide may increase the anticholinergic activities of Doxepin.
IsoflurophateThe serum concentration of Doxepin can be increased when it is combined with Isoflurophate.
ItoprideThe therapeutic efficacy of Itopride can be decreased when used in combination with Doxepin.
LeuprolideDoxepin may increase the QTc-prolonging activities of Leuprolide.
LinezolidLinezolid may increase the serotonergic activities of Doxepin.
LiothyronineLiothyronine may increase the arrhythmogenic activities of Doxepin.
LithiumLithium may increase the neurotoxic activities of Doxepin.
LorazepamThe risk or severity of adverse effects can be increased when Lorazepam is combined with Doxepin.
LoxapineThe risk or severity of adverse effects can be increased when Doxepin is combined with Loxapine.
Magnesium SulfateMagnesium Sulfate may increase the central nervous system depressant (CNS depressant) activities of Doxepin.
MesoridazineThe risk or severity of adverse effects can be increased when Doxepin is combined with Mesoridazine.
MethohexitalThe metabolism of Doxepin can be increased when combined with Methohexital.
MethotrimeprazineThe risk or severity of adverse effects can be increased when Doxepin is combined with Methotrimeprazine.
Methylene blueDoxepin may increase the serotonergic activities of Methylene blue.
MethylphenidateThe risk or severity of adverse effects can be increased when Methylphenidate is combined with Doxepin.
MetoclopramideThe risk or severity of adverse effects can be increased when Metoclopramide is combined with Doxepin.
MetyrosineDoxepin may increase the sedative activities of Metyrosine.
MianserinMianserin may increase the anticholinergic activities of Doxepin.
MidodrineDoxepin may increase the activities of Midodrine.
MifepristoneMifepristone may increase the QTc-prolonging activities of Doxepin.
MinocyclineMinocycline may increase the central nervous system depressant (CNS depressant) activities of Doxepin.
MirabegronThe risk or severity of adverse effects can be increased when Doxepin is combined with Mirabegron.
MolindoneThe risk or severity of adverse effects can be increased when Doxepin is combined with Molindone.
MorphineThe risk or severity of adverse effects can be increased when Doxepin is combined with Morphine.
MoxonidineThe therapeutic efficacy of Moxonidine can be decreased when used in combination with Doxepin.
NabiloneNabilone may increase the central nervous system depressant (CNS depressant) activities of Doxepin.
NicorandilDoxepin may increase the hypotensive activities of Nicorandil.
OlanzapineThe risk or severity of adverse effects can be increased when Doxepin is combined with Olanzapine.
OndansetronThe risk or severity of adverse effects can be increased when Doxepin is combined with Ondansetron.
OrciprenalineThe risk or severity of adverse effects can be increased when Doxepin is combined with Orciprenaline.
OrphenadrineDoxepin may increase the central nervous system depressant (CNS depressant) activities of Orphenadrine.
PaliperidoneThe risk or severity of adverse effects can be increased when Doxepin is combined with Paliperidone.
PanobinostatThe serum concentration of Doxepin can be increased when it is combined with Panobinostat.
ParaldehydeDoxepin may increase the central nervous system depressant (CNS depressant) activities of Paraldehyde.
ParoxetineThe risk or severity of adverse effects can be increased when Paroxetine is combined with Doxepin.
Peginterferon alfa-2bThe serum concentration of Doxepin can be decreased when it is combined with Peginterferon alfa-2b.
PentobarbitalThe metabolism of Doxepin can be increased when combined with Pentobarbital.
PerampanelPerampanel may increase the central nervous system depressant (CNS depressant) activities of Doxepin.
PerphenazineThe risk or severity of adverse effects can be increased when Doxepin is combined with Perphenazine.
PhenelzinePhenelzine may increase the serotonergic activities of Doxepin.
PimozideThe risk or severity of adverse effects can be increased when Doxepin is combined with Pimozide.
PiperacetazineThe risk or severity of adverse effects can be increased when Doxepin is combined with Piperacetazine.
Potassium ChlorideDoxepin may increase the ulcerogenic activities of Potassium Chloride.
PramipexoleDoxepin may increase the sedative activities of Pramipexole.
PramlintidePramlintide may increase the anticholinergic activities of Doxepin.
PrimidoneThe metabolism of Doxepin can be increased when combined with Primidone.
ProchlorperazineThe risk or severity of adverse effects can be increased when Doxepin is combined with Prochlorperazine.
ProcyclidineThe risk or severity of adverse effects can be increased when Procyclidine is combined with Doxepin.
PromazineThe risk or severity of adverse effects can be increased when Doxepin is combined with Promazine.
QuetiapineThe risk or severity of adverse effects can be increased when Doxepin is combined with Quetiapine.
QuinidineDoxepin may increase the QTc-prolonging activities of Quinidine.
RamosetronDoxepin may increase the activities of Ramosetron.
RemoxiprideThe risk or severity of adverse effects can be increased when Doxepin is combined with Remoxipride.
ReserpineThe risk or severity of adverse effects can be increased when Doxepin is combined with Reserpine.
RisperidoneThe risk or severity of adverse effects can be increased when Doxepin is combined with Risperidone.
RitonavirThe metabolism of Doxepin can be decreased when combined with Ritonavir.
RopiniroleDoxepin may increase the sedative activities of Ropinirole.
RotigotineDoxepin may increase the sedative activities of Rotigotine.
RufinamideThe risk or severity of adverse effects can be increased when Rufinamide is combined with Doxepin.
SecobarbitalThe metabolism of Doxepin can be increased when combined with Secobarbital.
SecretinThe therapeutic efficacy of Secretin can be decreased when used in combination with Doxepin.
SertindoleThe risk or severity of adverse effects can be increased when Doxepin is combined with Sertindole.
SertralineThe risk or severity of adverse effects can be increased when Sertraline is combined with Doxepin.
SimeprevirThe serum concentration of Doxepin can be increased when it is combined with Simeprevir.
Sodium oxybateSodium oxybate may increase the central nervous system depressant (CNS depressant) activities of Doxepin.
St. John's WortThe metabolism of Doxepin can be increased when combined with St. John&#39;s Wort.
SulpirideThe therapeutic efficacy of Sulpiride can be decreased when used in combination with Doxepin.
SuvorexantDoxepin may increase the central nervous system depressant (CNS depressant) activities of Suvorexant.
TacrineThe therapeutic efficacy of Doxepin can be decreased when used in combination with Tacrine.
TapentadolTapentadol may increase the central nervous system depressant (CNS depressant) activities of Doxepin.
Tedizolid PhosphateTedizolid Phosphate may increase the serotonergic activities of Doxepin.
TerbinafineThe metabolism of Doxepin can be decreased when combined with Terbinafine.
ThalidomideDoxepin may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
ThioridazineThe risk or severity of adverse effects can be increased when Doxepin is combined with Thioridazine.
ThiothixeneThe risk or severity of adverse effects can be increased when Doxepin is combined with Thiothixene.
TiclopidineThe metabolism of Doxepin can be decreased when combined with Ticlopidine.
TiotropiumDoxepin may increase the anticholinergic activities of Tiotropium.
TopiramateThe risk or severity of adverse effects can be increased when Doxepin is combined with Topiramate.
TramadolDoxepin may increase the neuroexcitatory activities of Tramadol.
TranylcypromineTranylcypromine may increase the serotonergic activities of Doxepin.
TrichlormethiazideThe serum concentration of Trichlormethiazide can be increased when it is combined with Doxepin.
TrifluoperazineThe risk or severity of adverse effects can be increased when Doxepin is combined with Trifluoperazine.
TriflupromazineThe risk or severity of adverse effects can be increased when Doxepin is combined with Triflupromazine.
UmeclidiniumUmeclidinium may increase the anticholinergic activities of Doxepin.
Valproic AcidThe serum concentration of Doxepin can be increased when it is combined with Valproic Acid.
YohimbineThe serum concentration of Yohimbine can be increased when it is combined with Doxepin.
ZiprasidoneThe risk or severity of adverse effects can be increased when Doxepin is combined with Ziprasidone.
ZolpidemDoxepin may increase the central nervous system depressant (CNS depressant) activities of Zolpidem.
ZuclopenthixolThe risk or severity of adverse effects can be increased when Doxepin is combined with Zuclopenthixol.
Food Interactions
  • Avoid alcohol.
  • Avoid excessive quantities of coffee or tea (caffeine).
  • Avoid St.John's Wort.
  • Take with food to reduce irritation.

Targets

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 catecholamine release from adrenal medulla, as well as mediating neurotransmission in the central nervous system.
Gene Name:
HRH1
Uniprot ID:
P35367
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 ]
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 differentiation. The activity of this receptor is mediated by G proteins which activate adenylyl cyclase and, through a separate G protein-dependent mechanism, the phosphoinositide/protein kinase (PKC) si...
Gene Name:
HRH2
Uniprot ID:
P25021
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
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 the pre-synaptic terminal for re-utilization. Plays a key role in mediating regulation of the availability of serotonin to other receptors of serotonergic systems. Terminates the action of serotonin an...
Gene Name:
SLC6A4
Uniprot ID:
P31645
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-iodophenyl)-2-aminopropane (DOI) and lysergic acid diethylamide (LSD). Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates...
Gene Name:
HTR2A
Uniprot ID:
P28223
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 change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors. Beta-arrestin family members inhibit signaling via G proteins ...
Gene Name:
HTR2B
Uniprot ID:
P41595
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-iodophenyl-2-aminopropane (DOI) and lysergic acid diethylamide (LSD). Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modul...
Gene Name:
HTR2C
Uniprot ID:
P28335
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 action of G proteins. Primary transducing effect is Pi turnover.
Gene Name:
CHRM1
Uniprot ID:
P11229
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 action of G proteins. Primary transducing effect is adenylate cyclase inhibition. Signaling promotes phospholipase C activity, leading to the release of inositol trisphosphate (IP3); this then trigge...
Gene Name:
CHRM2
Uniprot ID:
P08172
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 action of G proteins. Primary transducing effect is Pi turnover.
Gene Name:
CHRM3
Uniprot ID:
P20309
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 action of G proteins. Primary transducing effect is inhibition of adenylate cyclase.
Gene Name:
CHRM4
Uniprot ID:
P08173
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 action of G proteins. Primary transducing effect is Pi turnover.
Gene Name:
CHRM5
Uniprot ID:
P08912
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) proteins. Nuclear ADRA1A-ADRA1B heterooligomers regulate phenylephrine(PE)-stimulated ERK signaling in cardiac myocytes.
Gene Name:
ADRA1A
Uniprot ID:
P35348
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) proteins. Nuclear ADRA1A-ADRA1B heterooligomers regulate phenylephrine (PE)-stimulated ERK signaling in cardiac myocytes.
Gene Name:
ADRA1B
Uniprot ID:
P35368
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
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 signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors, such as adenylate cyclase. Beta-arrestin family members inhibit signaling via G pro...
Gene Name:
HTR1A
Uniprot ID:
P08908
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 oxymetazoline > clonidine > epinephrine > norepinephrine > phenylephrine > dopamine > p-synephrine > p-tyramine > serotonin = p-octopamine. For antagonists, the rank order is yohimbine > phentolamine = mianser...
Gene Name:
ADRA2A
Uniprot ID:
P08913
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 > norepinephrine > epinephrine = oxymetazoline > dopamine > p-tyramine = phenylephrine > serotonin > p-synephrine / p-octopamine. For antagonists, the rank order is yohimbine > chlorpromazine > phent...
Gene Name:
ADRA2B
Uniprot ID:
P18089
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
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
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 is mediated by G proteins that stimulate adenylate cyclase. It has a high affinity for tricyclic psychotropic drugs (By similarity). Controls pyramidal neurons migration during corticogenesis, through...
Gene Name:
HTR6
Uniprot ID:
P50406
Molecular Weight:
46953.625 Da
References
  1. PDSP Ki Database [Link]
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 agonist).
Gene Name:
HRH4
Uniprot ID:
Q9H3N8
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 delayed rectifying potassium current in heart (IKr). Isoforms USO have no channel activity by themself, but modulates channel characteristics by forming heterotetramers with other isoforms which are r...
Gene Name:
KCNH2
Uniprot ID:
Q12809
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
substrateinhibitor
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 antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
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 imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261
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 unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenyto...
Gene Name:
CYP2C9
Uniprot ID:
P11712
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 unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N...
Gene Name:
CYP1A2
Uniprot ID:
P05177
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 reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
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 the body. Appears to function in modulating the activity of the immune system during the acute-phase reaction.
Gene Name:
ORM1
Uniprot ID:
P02763
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
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 ]
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Drug created on June 13, 2005 07:24 / Updated on August 24, 2016 01:51