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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
SynonymsNot 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
AdapinNot Available
AponalNot Available
CuratinNot Available
Doxepine Not Available
Prudoxin Not Available
QuitaxonNot Available
Silenor Somaxon Pharmaceuticals, Inc.
SinequanPfizer
TriadapinNot Available
ZonalonNot Available
Brand mixturesNot Available
CategoriesNot Available
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[9.4.0.0^{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. <i>N</i>-demethylation produces an active metabolite, <i>N</i>-desmethyldoxepin. CYP2D6 specifically hydroxylates the E-isomer.

SubstrateEnzymesProduct
Doxepin
N-desmethyldoxepinDetails
Doxepin
    Doxepin N-oxideDetails
    Doxepin
      (E)-2-hydroxydoxepinDetails
      Doxepin
      (Z)-N-desmethyldoxepinDetails
      Doxepin
      (E)-N-desmethyldoxepinDetails
      Doxepin
        Doxepin-N-oxideDetails
        Doxepin
          (E)-2-O-glucuronyldoxepinDetails
          N-desmethyldoxepin
            Didesmethyl doxepinDetails
            Doxepin N-oxide
              Doxepin N-oxide glucuronideDetails
              (E)-2-hydroxydoxepin
                Hydroxydoxepin glucuronideDetails
                N-desmethyldoxepin
                Hydroxydesmethyl doxepinDetails
                (E)-2-hydroxydoxepin
                  Hydroxydesmethyl doxepinDetails
                  Hydroxydesmethyl doxepin
                    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.

                    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

                    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

                    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

                    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

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