General Information of Drug (ID: DMPI98T)

Drug Name
Doxepin
Synonyms
Zonalon; doxepin; Doxepine; Doxepinum [INN-Latin]; Doxepina [INN-Spanish]; Doxepin [USAN]; trans-doxepin; (e)-doxepin; 1668-19-5; Quitaxon; MF 10; UNII-851NLB57HQ; Sinequan; CCRIS 9176; HSDB 3069; Sinequan (TN); Cidoxepina; Cidoxepinum; 851NLB57HQ; 11-(3-(Dimethylamino)propylidene)-6H-dibenz(b,e)oxepine; 11-(3-Dimethylaminopropylidene)-6,11-dihydrodibenz(b,e)oxipin; 11-(3-Dimethylamino-propyliden)-6,11-dihydro-dibenz(b,e)oxipin; N,N-Dimethyldibenz(b,e)oxepin-delta(11(6H),gamma)-propylamine; Cidoxepin [INN]; Curatin; Adapin; Cidoxepin; Doxepina; Doxepinum; Triadapin; Doxepin Hydrochloride; MOLI001594; Adapine (TN); Aponal (TN); Cis-doxepin; Deptran (TN); Doxepin (INN); Doxepin, Hydrochloride; Sinquan (TN); Xepin (TN); Zonalon (TN); Doxepin (Z)-isomer; Cis-N-(3-(6H-Dibenz(b,e)oxepin-11-yliden)propyl)-N,N-dimethylamin; (3E)-3-(6H-benzo[c][1]benzoxepin-11-ylidene)-N,N-dimethylpropan-1-amine; (3E)-3-dibenzo[b,e]oxepin-11(6H)-ylidene-N,N-dimethylpropan-1-amine; (3Z)-3-(6H-benzo[c][1]benzoxepin-11-ylidene)-N,N-di(methyl)propan-1-amine; (3Z)-3-(6H-benzo[c][1]benzoxepin-11-ylidene)-N,N-dimethylpropan-1-amine; (3Z)-3-dibenzo[b,e]oxepin-11(6H)-ylidene-N,N-dimethylpropan-1-amine; (Z)-Doxepin; 3-(6H-benzo[c][1]benzoxepin-11-ylidene)-N,N-dimethylpropan-1-amine; 3-Dibenz[b,e]oxepin-11(6H)-ylidene-N,N-dimethyl-1-propanamine; 3-dibenzo[b,e]oxepin-11(6H)-ylidene-N,N-dimethylpropan-1-amine; [11C]doxepin
Indication
Disease Entry ICD 11 Status REF
Anxiety N.A. Approved [1]
Bipolar depression N.A. Approved [1]
Depression 6A70-6A7Z Approved [2]
Insomnia 7A00-7A0Z Approved [1]
Pruritus EC90 Investigative [1]
Therapeutic Class
Antidepressants
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 279.4
Logarithm of the Partition Coefficient (xlogp) 4.3
Rotatable Bond Count (rotbonds) 3
Hydrogen Bond Donor Count (hbonddonor) 0
Hydrogen Bond Acceptor Count (hbondacc) 2
ADMET Property
Absorption AUC
The area under the plot of plasma concentration (AUC) of drug is 25.5 mgh/L [3]
Absorption Cmax
The maximum plasma concentration (Cmax) of drug is 12.72 mg/L [3]
Absorption Tmax
The time to maximum plasma concentration (Tmax) is 0.25 h [3]
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 1: high solubility and high permeability [4]
Clearance
The clearance of drug is 0.93 L/h/kg [5]
Elimination
Less than 3% of a doxepin dose is excreted in the urine as parent compound or nordoxepin [5]
Half-life
The concentration or amount of drug in body reduced by one-half in 15 hours [6]
Metabolism
The drug is metabolized via the transformation of N-desmethyldoxepin to its glucuronide conjugates [7]
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 17.89643 micromolar/kg/day [8]
Unbound Fraction
The unbound fraction of drug in plasma is 0.2% [6]
Vd
The volume of distribution (Vd) of drug is 20 L/kg []
Adverse Drug Reaction (ADR)
ADR Term Variation Related DOT DOT ID REF
Poisoning and toxicity Not Available CYP2D6 OTZJC802 [9]
Chemical Identifiers
Formula
C19H21NO
IUPAC Name
(3E)-3-(6H-benzo[c][1]benzoxepin-11-ylidene)-N,N-dimethylpropan-1-amine
Canonical SMILES
CN(C)CC/C=C/1\\C2=CC=CC=C2COC3=CC=CC=C31
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+
InChIKey
ODQWQRRAPPTVAG-GZTJUZNOSA-N
Cross-matching ID
PubChem CID
667477
CAS Number
1668-19-5
DrugBank ID
DB01142
TTD ID
D06FES
VARIDT ID
DR00542
INTEDE ID
DR0544
ACDINA ID
D00626
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug
Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Histamine H1 receptor (H1R) TTTIBOJ HRH1_HUMAN Inhibitor [10]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4) DE4LYSA CP3A4_HUMAN Substrate [11]
Cytochrome P450 2D6 (CYP2D6)
Main DME
DECB0K3 CP2D6_HUMAN Substrate [12]
Cytochrome P450 2C9 (CYP2C9) DE5IED8 CP2C9_HUMAN Substrate [13]
Mephenytoin 4-hydroxylase (CYP2C19)
Main DME
DEGTFWK CP2CJ_HUMAN Substrate [13]
Cytochrome P450 1A2 (CYP1A2) DEJGDUW CP1A2_HUMAN Substrate [11]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Alpha-1-antichymotrypsin (SERPINA3) OT9BP2S0 AACT_HUMAN Gene/Protein Processing [14]
Angiotensin-converting enzyme 2 (ACE2) OTTRZGU7 ACE2_HUMAN Gene/Protein Processing [15]
Asparagine synthetase (ASNS) OT8R922G ASNS_HUMAN Gene/Protein Processing [14]
Cytochrome P450 2D6 (CYP2D6) OTZJC802 CP2D6_HUMAN Drug Response [9]
Fatty acid-binding protein, liver (FABP1) OTR34ETM FABPL_HUMAN Gene/Protein Processing [14]
Glutathione S-transferase P (GSTP1) OTLP0A0Y GSTP1_HUMAN Gene/Protein Processing [16]
Inhibin beta E chain (INHBE) OTOI2NYG INHBE_HUMAN Gene/Protein Processing [14]
Lanosterol synthase (LSS) OT9W2SFH LSS_HUMAN Gene/Protein Processing [14]
Lysophospholipase D GDPD3 (GDPD3) OTOHM9QM GDPD3_HUMAN Gene/Protein Processing [14]
Nuclear protein 1 (NUPR1) OT4FU8C0 NUPR1_HUMAN Gene/Protein Processing [14]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Anxiety
ICD Disease Classification
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Histamine H1 receptor (H1R) DTT HRH1 6.74E-01 0.13 0.43
Cytochrome P450 1A2 (CYP1A2) DME CYP1A2 8.46E-01 -6.63E-03 -4.49E-02
Mephenytoin 4-hydroxylase (CYP2C19) DME CYP2C19 9.62E-01 2.57E-02 1.10E-01
Cytochrome P450 2D6 (CYP2D6) DME CYP2D6 8.70E-01 2.98E-02 1.22E-01
Cytochrome P450 2C9 (CYP2C9) DME CYP2C9 2.35E-01 2.78E-02 2.09E-01
Cytochrome P450 3A4 (CYP3A4) DME CYP3A4 1.76E-01 1.26E-01 8.27E-01
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Same Disease as Doxepin
DDI Drug Name DDI Drug ID Severity Mechanism Disease REF
Vilazodone DM4LECQ Major Additive serotonergic effects by the combination of Doxepin and Vilazodone. Depression [6A70-6A7Z] [17]
Nefazodone DM4ZS8M Major Additive serotonergic effects by the combination of Doxepin and Nefazodone. Depression [6A70-6A7Z] [18]
Vortioxetine DM6F1PU Major Additive serotonergic effects by the combination of Doxepin and Vortioxetine. Depression [6A70-6A7Z] [18]
Isocarboxazid DMAF1NB Major Additive serotonergic effects by the combination of Doxepin and Isocarboxazid. Depression [6A70-6A7Z] [19]
Milnacipran DMBFE74 Major Additive serotonergic effects by the combination of Doxepin and Milnacipran. Depression [6A70-6A7Z] [18]
Escitalopram DMFK9HG Major Additive serotonergic effects by the combination of Doxepin and Escitalopram. Depression [6A70-6A7Z] [20]
Desvenlafaxine DMHD4PE Major Additive serotonergic effects by the combination of Doxepin and Desvenlafaxine. Depression [6A70-6A7Z] [18]
OPC-34712 DMHG57U Moderate Additive anticholinergic effects by the combination of Doxepin and OPC-34712. Depression [6A70-6A7Z] [21]
Clomipramine DMINRKW Moderate Additive anticholinergic effects by the combination of Doxepin and Clomipramine. Depression [6A70-6A7Z] [22]
Esketamine DMVU687 Moderate Additive CNS depression effects by the combination of Doxepin and Esketamine. Depression [6A70-6A7Z] [23]
⏷ Show the Full List of 10 DDI Information of This Drug
Coadministration of a Drug Treating the Disease Different from Doxepin (Comorbidity)
DDI Drug Name DDI Drug ID Severity Mechanism Comorbidity REF
Methylene blue DMJAPE7 Major Additive serotonergic effects by the combination of Doxepin and Methylene blue. Acquired methaemoglobinaemia [3A93] [19]
Ivosidenib DM8S6T7 Major Increased risk of prolong QT interval by the combination of Doxepin and Ivosidenib. Acute myeloid leukaemia [2A60] [24]
Midostaurin DMI6E0R Moderate Increased risk of prolong QT interval by the combination of Doxepin and Midostaurin. Acute myeloid leukaemia [2A60] [25]
Idarubicin DMM0XGL Moderate Increased risk of prolong QT interval by the combination of Doxepin and Idarubicin. Acute myeloid leukaemia [2A60] [25]
Arn-509 DMT81LZ Moderate Increased risk of prolong QT interval by the combination of Doxepin and Arn-509. Acute myeloid leukaemia [2A60] [26]
Gilteritinib DMTI0ZO Moderate Increased risk of prolong QT interval by the combination of Doxepin and Gilteritinib. Acute myeloid leukaemia [2A60] [27]
Oliceridine DM6MDCF Moderate Additive CNS depression effects by the combination of Doxepin and Oliceridine. Acute pain [MG31] [28]
Mepyramine DMB4SFH Moderate Additive anticholinergic effects by the combination of Doxepin and Mepyramine. Allergic/hypersensitivity disorder [4A80-4A8Z] [22]
Phenyltoloxamine DMKAEQW Moderate Additive anticholinergic effects by the combination of Doxepin and Phenyltoloxamine. Allergic/hypersensitivity disorder [4A80-4A8Z] [22]
Ivabradine DM0L594 Major Increased risk of ventricular arrhythmias by the combination of Doxepin and Ivabradine. Angina pectoris [BA40] [26]
Bepridil DM0RKS4 Major Increased risk of prolong QT interval by the combination of Doxepin and Bepridil. Angina pectoris [BA40] [29]
Dronedarone DMA8FS5 Major Increased risk of prolong QT interval by the combination of Doxepin and Dronedarone. Angina pectoris [BA40] [25]
Bedaquiline DM3906J Major Increased risk of prolong QT interval by the combination of Doxepin and Bedaquiline. Antimicrobial drug resistance [MG50-MG52] [30]
Cilostazol DMZMSCT Moderate Increased risk of prolong QT interval by the combination of Doxepin and Cilostazol. Arterial occlusive disease [BD40] [25]
Posaconazole DMUL5EW Moderate Increased risk of prolong QT interval by the combination of Doxepin and Posaconazole. Aspergillosis [1F20] [25]
Desipramine DMT2FDC Moderate Additive anticholinergic effects by the combination of Doxepin and Desipramine. Attention deficit hyperactivity disorder [6A05] [21]
Ofloxacin DM0VQN3 Moderate Increased risk of prolong QT interval by the combination of Doxepin and Ofloxacin. Bacterial infection [1A00-1C4Z] [31]
Sparfloxacin DMB4HCT Major Increased risk of prolong QT interval by the combination of Doxepin and Sparfloxacin. Bacterial infection [1A00-1C4Z] [32]
Gemifloxacin DMHT34O Moderate Increased risk of prolong QT interval by the combination of Doxepin and Gemifloxacin. Bacterial infection [1A00-1C4Z] [31]
Retigabine DMGNYIH Moderate Increased risk of prolong QT interval by the combination of Doxepin and Retigabine. Behcet disease [4A62] [25]
Cariprazine DMJYDVK Moderate Additive anticholinergic effects by the combination of Doxepin and Cariprazine. Bipolar disorder [6A60] [22]
Eribulin DM1DX4Q Moderate Increased risk of prolong QT interval by the combination of Doxepin and Eribulin. Breast cancer [2C60-2C6Y] [25]
Lapatinib DM3BH1Y Moderate Increased risk of prolong QT interval by the combination of Doxepin and Lapatinib. Breast cancer [2C60-2C6Y] [25]
Alpelisib DMEXMYK Moderate Increased metabolism of Doxepin caused by Alpelisib mediated induction of CYP450 enzyme. Breast cancer [2C60-2C6Y] [33]
Bosutinib DMTI8YE Moderate Increased risk of prolong QT interval by the combination of Doxepin and Bosutinib. Breast cancer [2C60-2C6Y] [26]
Acetylcholine DMDF79Z Moderate Antagonize the effect of Doxepin when combined with Acetylcholine. Cataract [9B10] [34]
PF-04449913 DMSB068 Moderate Increased risk of prolong QT interval by the combination of Doxepin and PF-04449913. Chronic myelomonocytic leukaemia [2A40] [35]
Umeclidinium DM4E8O9 Moderate Additive anticholinergic effects by the combination of Doxepin and Umeclidinium. Chronic obstructive pulmonary disease [CA22] [36]
Tiotropium DMFDC0Q Moderate Additive anticholinergic effects by the combination of Doxepin and Tiotropium. Chronic obstructive pulmonary disease [CA22] [36]
Revefenacin DMMP5SI Moderate Additive anticholinergic effects by the combination of Doxepin and Revefenacin. Chronic obstructive pulmonary disease [CA22] [36]
Dihydrocodeine DMB0FWL Moderate Additive serotonergic effects by the combination of Doxepin and Dihydrocodeine. Chronic pain [MG30] [28]
Levomilnacipran DMV26S8 Major Additive serotonergic effects by the combination of Doxepin and Levomilnacipran. Chronic pain [MG30] [18]
Mestranol DMG3F94 Minor Decreased metabolism of Doxepin caused by Mestranol. Contraceptive management [QA21] [37]
Halothane DM80OZ5 Moderate Increased risk of prolong QT interval by the combination of Doxepin and Halothane. Corneal disease [9A76-9A78] [25]
Sevoflurane DMC9O43 Moderate Increased risk of prolong QT interval by the combination of Doxepin and Sevoflurane. Corneal disease [9A76-9A78] [23]
Probucol DMVZQ2M Moderate Increased risk of prolong QT interval by the combination of Doxepin and Probucol. Coronary atherosclerosis [BA80] [25]
Pasireotide DMHM7JS Major Increased risk of prolong QT interval by the combination of Doxepin and Pasireotide. Cushing syndrome [5A70] [25]
Osilodrostat DMIJC9X Moderate Increased risk of prolong QT interval by the combination of Doxepin and Osilodrostat. Cushing syndrome [5A70] [26]
Mepenzolate DM8YU2F Moderate Additive anticholinergic effects by the combination of Doxepin and Mepenzolate. Digestive system disease [DE2Z] [22]
5-hydroxy-L-tryptophan DMDWZGJ Major Additive serotonergic effects by the combination of Doxepin and 5-hydroxy-L-tryptophan. Discovery agent [N.A.] [17]
Tetrabenazine DMYWQ0O Moderate Increased risk of prolong QT interval by the combination of Doxepin and Tetrabenazine. Dissociative neurological symptom disorder [6B60] [25]
Deutetrabenazine DMUPFLI Moderate Increased risk of prolong QT interval by the combination of Doxepin and Deutetrabenazine. Dystonic disorder [8A02] [38]
Fosphenytoin DMOX3LB Moderate Decreased metabolism of Doxepin caused by Fosphenytoin mediated inhibition of CYP450 enzyme. Epilepsy/seizure [8A61-8A6Z] [39]
Solifenacin DMG592Q Moderate Additive anticholinergic effects by the combination of Doxepin and Solifenacin. Functional bladder disorder [GC50] [21]
Mirabegron DMS1GYT Moderate Decreased metabolism of Doxepin caused by Mirabegron mediated inhibition of CYP450 enzyme. Functional bladder disorder [GC50] [40]
Sunitinib DMCBJSR Moderate Increased risk of prolong QT interval by the combination of Doxepin and Sunitinib. Gastrointestinal stromal tumour [2B5B] [25]
Procarbazine DMIK367 Major Additive serotonergic effects by the combination of Doxepin and Procarbazine. Hodgkin lymphoma [2B30] [41]
Fostemsavir DM50ILT Moderate Increased risk of prolong QT interval by the combination of Doxepin and Fostemsavir. Human immunodeficiency virus disease [1C60-1C62] [42]
Cobicistat DM6L4H2 Moderate Decreased metabolism of Doxepin caused by Cobicistat mediated inhibition of CYP450 enzyme. Human immunodeficiency virus disease [1C60-1C62] [43]
Saquinavir DMG814N Major Increased risk of prolong QT interval by the combination of Doxepin and Saquinavir. Human immunodeficiency virus disease [1C60-1C62] [44]
Rilpivirine DMJ0QOW Moderate Increased risk of prolong QT interval by the combination of Doxepin and Rilpivirine. Human immunodeficiency virus disease [1C60-1C62] [25]
Givosiran DM5PFIJ Moderate Decreased metabolism of Doxepin caused by Givosiran mediated inhibition of CYP450 enzyme. Inborn porphyrin/heme metabolism error [5C58] [45]
Belladonna DM2RBWK Moderate Additive anticholinergic effects by the combination of Doxepin and Belladonna. Infectious gastroenteritis/colitis [1A40] [21]
Berotralstat DMWA2DZ Moderate Decreased metabolism of Doxepin caused by Berotralstat mediated inhibition of CYP450 enzyme. Innate/adaptive immunodeficiency [4A00] [46]
ITI-007 DMUQ1DO Moderate Additive anticholinergic effects by the combination of Doxepin and ITI-007. Insomnia [7A00-7A0Z] [21]
Polyethylene glycol DM4I1JP Moderate Increased risk of lowers seizure threshold by the combination of Doxepin and Polyethylene glycol. Irritable bowel syndrome [DD91] [25]
Glycerol phenylbutyrate DMDGRQO Moderate Decreased metabolism of Doxepin caused by Glycerol phenylbutyrate mediated inhibition of CYP450 enzyme. Liver disease [DB90-DB9Z] [26]
Crizotinib DM4F29C Major Increased risk of prolong QT interval by the combination of Doxepin and Crizotinib. Lung cancer [2C25] [47]
Ceritinib DMB920Z Major Increased risk of prolong QT interval by the combination of Doxepin and Ceritinib. Lung cancer [2C25] [25]
PF-06463922 DMKM7EW Moderate Increased metabolism of Doxepin caused by PF-06463922 mediated induction of CYP450 enzyme. Lung cancer [2C25] [23]
Dacomitinib DMOH8VY Moderate Decreased metabolism of Doxepin caused by Dacomitinib mediated inhibition of CYP450 enzyme. Lung cancer [2C25] [48]
Osimertinib DMRJLAT Major Increased risk of prolong QT interval by the combination of Doxepin and Osimertinib. Lung cancer [2C25] [49]
Selpercatinib DMZR15V Major Increased risk of prolong QT interval by the combination of Doxepin and Selpercatinib. Lung cancer [2C25] [50]
Lumefantrine DM29GAD Major Increased risk of prolong QT interval by the combination of Doxepin and Lumefantrine. Malaria [1F40-1F45] [23]
Halofantrine DMOMK1V Major Increased risk of prolong QT interval by the combination of Doxepin and Halofantrine. Malaria [1F40-1F45] [51]
Hydroxychloroquine DMSIVND Major Increased risk of prolong QT interval by the combination of Doxepin and Hydroxychloroquine. Malaria [1F40-1F45] [52]
Inotuzumab ozogamicin DMAC130 Moderate Increased risk of prolong QT interval by the combination of Doxepin and Inotuzumab ozogamicin. Malignant haematopoietic neoplasm [2B33] [26]
Arsenic trioxide DM61TA4 Major Increased risk of ventricular arrhythmias by the combination of Doxepin and Arsenic trioxide. Mature B-cell lymphoma [2A85] [53]
Vemurafenib DM62UG5 Major Increased risk of prolong QT interval by the combination of Doxepin and Vemurafenib. Melanoma [2C30] [25]
LGX818 DMNQXV8 Moderate Increased risk of prolong QT interval by the combination of Doxepin and LGX818. Melanoma [2C30] [54]
Allopregnanolone DMNLHAC Moderate Additive CNS depression effects by the combination of Doxepin and Allopregnanolone. Mental/behavioural/neurodevelopmental disorder [6E20-6E8Z] [55]
Flibanserin DM70DTN Moderate Additive CNS depression effects by the combination of Doxepin and Flibanserin. Mood disorder [6A60-6E23] [56]
Panobinostat DM58WKG Major Increased risk of prolong QT interval by the combination of Doxepin and Panobinostat. Multiple myeloma [2A83] [57]
Siponimod DM2R86O Major Increased risk of ventricular arrhythmias by the combination of Doxepin and Siponimod. Multiple sclerosis [8A40] [23]
Fingolimod DM5JVAN Major Increased risk of ventricular arrhythmias by the combination of Doxepin and Fingolimod. Multiple sclerosis [8A40] [25]
Ozanimod DMT6AM2 Major Additive serotonergic effects by the combination of Doxepin and Ozanimod. Multiple sclerosis [8A40] [58]
Romidepsin DMT5GNL Moderate Increased risk of prolong QT interval by the combination of Doxepin and Romidepsin. Mycosis fungoides [2B01] [25]
Fedratinib DM4ZBK6 Moderate Decreased metabolism of Doxepin caused by Fedratinib mediated inhibition of CYP450 enzyme. Myeloproliferative neoplasm [2A20] [26]
Nilotinib DM7HXWT Major Increased risk of prolong QT interval by the combination of Doxepin and Nilotinib. Myeloproliferative neoplasm [2A20] [25]
Dasatinib DMJV2EK Moderate Increased risk of prolong QT interval by the combination of Doxepin and Dasatinib. Myeloproliferative neoplasm [2A20] [23]
Phenindamine DMDTC7R Moderate Additive anticholinergic effects by the combination of Doxepin and Phenindamine. Nasopharyngitis [CA00] [21]
Rolapitant DM8XP26 Moderate Decreased metabolism of Doxepin caused by Rolapitant mediated inhibition of CYP450 enzyme. Nausea/vomiting [MD90] [59]
Cyclizine DM9G7BS Moderate Additive anticholinergic effects by the combination of Doxepin and Cyclizine. Nausea/vomiting [MD90] [21]
Bupropion DM5PCS7 Major Decreased metabolism of Doxepin caused by Bupropion mediated inhibition of CYP450 enzyme. Nicotine use disorder [6C4A] [60]
Entrectinib DMMPTLH Moderate Increased risk of prolong QT interval by the combination of Doxepin and Entrectinib. Non-small cell lung cancer [2C25] [26]
Lorcaserin DMG6OYJ Major Additive serotonergic effects by the combination of Doxepin and Lorcaserin. Obesity [5B80-5B81] [61]
Dexfenfluramine DMJ7YDS Major Additive serotonergic effects by the combination of Doxepin and Dexfenfluramine. Obesity [5B80-5B81] [18]
Levomethadyl Acetate DM06HG5 Major Increased risk of prolong QT interval by the combination of Doxepin and Levomethadyl Acetate. Opioid use disorder [6C43] [26]
Lofexidine DM1WXA6 Moderate Increased risk of prolong QT interval by the combination of Doxepin and Lofexidine. Opioid use disorder [6C43] [26]
Rucaparib DM9PVX8 Moderate Increased risk of prolong QT interval by the combination of Doxepin and Rucaparib. Ovarian cancer [2C73] [25]
Oxymorphone DM65AGJ Moderate Additive CNS depression effects by the combination of Doxepin and Oxymorphone. Pain [MG30-MG3Z] [28]
Dezocine DMJDB0Y Moderate Additive CNS depression effects by the combination of Doxepin and Dezocine. Pain [MG30-MG3Z] [28]
Flavoxate DMKV4NL Moderate Additive anticholinergic effects by the combination of Doxepin and Flavoxate. Pain [MG30-MG3Z] [21]
Triclabendazole DMPWGBR Moderate Increased risk of prolong QT interval by the combination of Doxepin and Triclabendazole. Parasitic worm infestation [1F90] [25]
Safinamide DM0YWJC Major Additive serotonergic effects by the combination of Doxepin and Safinamide. Parkinsonism [8A00] [58]
Rasagiline DM3WKQ4 Major Additive serotonergic effects by the combination of Doxepin and Rasagiline. Parkinsonism [8A00] [41]
Levodopa DMN3E57 Minor Altered absorption of Doxepin due to GI dynamics variation caused by Levodopa. Parkinsonism [8A00] [62]
Pimavanserin DMR7IVC Moderate Increased risk of prolong QT interval by the combination of Doxepin and Pimavanserin. Parkinsonism [8A00] [63]
Orphenadrine DMW542E Moderate Additive anticholinergic effects by the combination of Doxepin and Orphenadrine. Parkinsonism [8A00] [22]
Methylscopolamine DM5VWOB Moderate Additive anticholinergic effects by the combination of Doxepin and Methylscopolamine. Peptic ulcer [DA61] [21]
Macimorelin DMQYJIR Major Increased risk of prolong QT interval by the combination of Doxepin and Macimorelin. Pituitary gland disorder [5A60-5A61] [24]
Lefamulin DME6G97 Major Increased risk of prolong QT interval by the combination of Doxepin and Lefamulin. Pneumonia [CA40] [64]
Degarelix DM3O8QY Moderate Increased risk of prolong QT interval by the combination of Doxepin and Degarelix. Prostate cancer [2C82] [26]
ABIRATERONE DM8V75C Moderate Decreased metabolism of Doxepin caused by ABIRATERONE mediated inhibition of CYP450 enzyme. Prostate cancer [2C82] [65]
Enzalutamide DMGL19D Moderate Increased risk of prolong QT interval by the combination of Doxepin and Enzalutamide. Prostate cancer [2C82] [26]
Relugolix DMK7IWL Moderate Increased risk of prolong QT interval by the combination of Doxepin and Relugolix. Prostate cancer [2C82] [26]
Levomepromazine DMIKFEL Moderate Increased plasma concentrations of Doxepin and Levomepromazine due to competitive inhibition of the same metabolic pathway. Psychotic disorder [6A20-6A25] [66]
Quetiapine DM1N62C Moderate Increased risk of prolong QT interval by the combination of Doxepin and Quetiapine. Schizophrenia [6A20] [25]
Aripiprazole DM3NUMH Moderate Additive anticholinergic effects by the combination of Doxepin and Aripiprazole. Schizophrenia [6A20] [21]
Iloperidone DM6AUFY Major Increased risk of prolong QT interval by the combination of Doxepin and Iloperidone. Schizophrenia [6A20] [25]
Paliperidone DM7NPJS Moderate Increased risk of prolong QT interval by the combination of Doxepin and Paliperidone. Schizophrenia [6A20] [25]
Molindone DMAH70G Moderate Additive anticholinergic effects by the combination of Doxepin and Molindone. Schizophrenia [6A20] [21]
Thiothixene DMDINC4 Moderate Additive anticholinergic effects by the combination of Doxepin and Thiothixene. Schizophrenia [6A20] [21]
Amisulpride DMSJVAM Major Increased risk of prolong QT interval by the combination of Doxepin and Amisulpride. Schizophrenia [6A20] [67]
Asenapine DMSQZE2 Moderate Increased risk of prolong QT interval by the combination of Doxepin and Asenapine. Schizophrenia [6A20] [25]
Armodafinil DMGB035 Moderate Decreased metabolism of Doxepin caused by Armodafinil mediated inhibition of CYP450 enzyme. Solid tumour/cancer [2A00-2F9Z] [23]
LEE011 DMMX75K Major Increased risk of prolong QT interval by the combination of Doxepin and LEE011. Solid tumour/cancer [2A00-2F9Z] [25]
Vandetanib DMRICNP Major Increased risk of prolong QT interval by the combination of Doxepin and Vandetanib. Solid tumour/cancer [2A00-2F9Z] [23]
Telavancin DM58VQX Moderate Increased risk of prolong QT interval by the combination of Doxepin and Telavancin. Staphylococcal/streptococcal disease [1B5Y] [25]
Lenvatinib DMB1IU4 Moderate Increased risk of prolong QT interval by the combination of Doxepin and Lenvatinib. Thyroid cancer [2D10] [25]
Cabozantinib DMIYDT4 Major Increased risk of prolong QT interval by the combination of Doxepin and Cabozantinib. Thyroid cancer [2D10] [26]
Trimeprazine DMEMV9D Moderate Increased plasma concentrations of Doxepin and Trimeprazine due to competitive inhibition of the same metabolic pathway. Vasomotor/allergic rhinitis [CA08] [68]
Acrivastine DMTIGA0 Moderate Additive anticholinergic effects by the combination of Doxepin and Acrivastine. Vasomotor/allergic rhinitis [CA08] [21]
Propafenone DMPIBJK Moderate Decreased metabolism of Doxepin caused by Propafenone mediated inhibition of CYP450 enzyme. Ventricular tachyarrhythmia [BC71] [69]
Flecainide DMSQDLE Moderate Increased risk of prolong QT interval by the combination of Doxepin and Flecainide. Ventricular tachyarrhythmia [BC71] [69]
⏷ Show the Full List of 125 DDI Information of This Drug

Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG
DIG Name DIG ID PubChem CID Functional Classification
Allura red AC dye E00338 33258 Colorant
Diiodofluorescein E00385 92311 Colorant
FD&C blue no. 1 E00263 19700 Colorant
FD&C blue no. 2 E00446 2723854 Colorant
Quinoline yellow WS E00309 24671 Colorant
Sodium lauryl sulfate E00464 3423265 Emulsifying agent; Modified-release agent; Penetration agent; Solubilizing agent; Surfactant; lubricant
Sunset yellow FCF E00255 17730 Colorant
Ammonia E00007 222 Alkalizing agent
Butyl alcohol E00011 263 Flavoring agent; Solvent
Ferrosoferric oxide E00231 14789 Colorant
Magnesium stearate E00208 11177 lubricant
Potassium hydroxide E00233 14797 Alkalizing agent
Propylene glycol E00040 1030 Antimicrobial preservative; Humectant; Plasticizing agent; Solvent
Silicon dioxide E00670 Not Available Anticaking agent; Opacifying agent; Viscosity-controlling agent
Titanium dioxide E00322 26042 Coating agent; Colorant; Opacifying agent
⏷ Show the Full List of 15 Pharmaceutical Excipients of This Drug
Pharmaceutical Formulation
Formulation Name Drug Dosage Dosage Form Route
Sinequan 150 mg capsule 150 mg Oral Capsule Oral
Sinequan 10 mg capsule 10 mg Oral Capsule Oral
Sinequan 100 mg capsule 100 mg Oral Capsule Oral
Sinequan 25 mg capsule 25 mg Oral Capsule Oral
Sinequan 50 mg capsule 50 mg Oral Capsule Oral
Sinequan 75 mg capsule 75 mg Oral Capsule Oral
Sinequan 6 mg tablet 6 mg Oral Tablet Oral
Sinequan 3 mg tablet 3 mg Oral Tablet Oral
Jump to Detail Pharmaceutical Formulation Page of This Drug

References

1 Doxepin FDA Label
2 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 1225).
3 New zealand perfalgan report
4 BDDCS applied to over 900 drugs
5 Virtanen R, Scheinin M, Iisalo E: Single dose pharmacokinetics of doxepin in healthy volunteers. Acta Pharmacol Toxicol (Copenh). 1980 Nov;47(5):371-6.
6 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
7 Nelis HJ, De Leenheer AP: Metabolism of minocycline in humans. Drug Metab Dispos. 1982 Mar-Apr;10(2):142-6.
8 Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
9 ADReCS-Target: target profiles for aiding drug safety research and application. Nucleic Acids Res. 2018 Jan 4;46(D1):D911-D917. doi: 10.1093/nar/gkx899.
10 Novel therapeutic usage of low-dose doxepin hydrochloride. Expert Opin Investig Drugs. 2007 Aug;16(8):1295-305.
11 The N-demethylation of the doxepin isomers is mainly catalyzed by the polymorphic CYP2C19. Pharm Res. 2002 Jul;19(7):1034-7.
12 Doxepin inhibits CYP2D6 activity in vivo. Pol J Pharmacol. 2004 Jul-Aug;56(4):491-4.
13 Contributions of CYP2D6, CYP2C9 and CYP2C19 to the biotransformation of E- and Z-doxepin in healthy volunteers. Pharmacogenetics. 2002 Oct;12(7):571-80.
14 In vitro detection of drug-induced phospholipidosis using gene expression and fluorescent phospholipid based methodologies. Toxicol Sci. 2007 Sep;99(1):162-73.
15 Effect of common medications on the expression of SARS-CoV-2 entry receptors in liver tissue. Arch Toxicol. 2020 Dec;94(12):4037-4041. doi: 10.1007/s00204-020-02869-1. Epub 2020 Aug 17.
16 Glutathione S-transferase pi as a target for tricyclic antidepressants in human brain. Acta Biochim Pol. 2004;51(1):207-12.
17 Ciraulo DA, Shader RI "Fluoxetine drug-drug interactions: I. Antidepressants and antipsychotics." J Clin Psychopharmacol 10 (1990): 48-50. [PMID: 1968472]
18 Achamallah NS "Visual hallucinations after combining fluoxetine and dextromethorphan ." Am J Psychiatry 149 (1992): 1406. [PMID: 1530079]
19 Spiker DG, Pugh DD "Combining tricyclic and monoamine oxidase inhibitor antidepressants." Arch Gen Psychiatry 33 (1976): 828-30. [PMID: 942286]
20 Bhatara VS, Magnus RD, Paul KL, Preskorn SH "Serotonin syndrome induced by venlafaxine and fluoxetine: a case study in polypharmacy and potential pharmacodynamic and pharmacokinetic mechanisms." Ann Pharmacother 32 (1998): 432-6. [PMID: 9562139]
21 Cohen MA, Alfonso CA, Mosquera M. Development of urinary retention during treatment with clozapine and meclizine [published correction appears in Am J Psychiatry 1994 Jun;151(6):952]. Am J Psychiatry. 1994;151(4):619-620. [PMID: 8147469]
22 Kulik AV, Wilbur R "Delirium and stereotypy from anticholinergic antiparkinson drugs." Prog Neuropsychopharmacol Biol Psychiatry 6 (1982): 75-82. [PMID: 7202232]
23 Cerner Multum, Inc. "Australian Product Information.".
24 Product Information. Fycompa (perampanel). Eisai Inc, Teaneck, NJ.
25 Canadian Pharmacists Association.
26 Cerner Multum, Inc. "UK Summary of Product Characteristics.".
27 Product Information. Xospata (gilteritinib). Astellas Pharma US, Inc, Deerfield, IL.
28 Vizcaychipi MP, Walker S, Palazzo M "Serotonin syndrome triggered by tramadol." Br J Anaesth 99 (2007): 919. [PMID: 18006535]
29 Gunston GD, Mehta U "Potentially serious drug interactions with grapefruit juice." S Afr Med J 90 (2000): 41. [PMID: 10721388]
30 Product Information. Sirturo (bedaquiline). Janssen Pharmaceuticals, Titusville, NJ.
31 Ball P "Quinolone-induced QT interval prolongation: a not-so-unexpected class effect." J Antimicrob Chemother 45 (2000): 557-9. [PMID: 10797074]
32 Dupont H, Timsit JF, Souweine B, Gachot B, Wolff M, Regnier B "Torsades de pointe probably related to sparfloxacin." Eur J Clin Microbiol Infect Dis 15 (1996): 350-1. [PMID: 8781892]
33 Product Information. Piqray (alpelisib). Novartis Pharmaceuticals, East Hanover, NJ.
34 Multum Information Services, Inc. Expert Review Panel.
35 Product Information. Daurismo (glasdegib). Pfizer U.S. Pharmaceuticals Group, New York, NY.
36 Cole JM, Sheehan AH, Jordan JK "Concomitant use of ipratropium and tiotropium in chronic obstructive plmonary disease." Ann Pharmacother 46 (2012): 1717-21. [PMID: 23170031]
37 Edelbroek PM, Zitman FG, Knoppert-van der Klein EA, van Putten PM, de Wolff FA "Therapeutic drug monitoring of amitriptyline: impact of age, smoking and contraceptives on drug and metabolite levels in bulimic women." Clin Chim Acta 165 (1987): 177-87. [PMID: 3652444]
38 Product Information. Austedo (deutetrabenazine). Teva Pharmaceuticals USA, North Wales, PA.
39 Agencia Espaola de Medicamentos y Productos Sanitarios Healthcare "Centro de informacion online de medicamentos de la AEMPS - CIMA.".
40 Product Information. Myrbetriq (mirabegron). Astellas Pharma US, Inc, Deerfield, IL.
41 Boyer EW, Shannon M "The serotonin syndrome." N Engl J Med 352 (2005): 1112-20. [PMID: 15784664]
42 Product Information. Rukobia (fostemsavir). ViiV Healthcare, Research Triangle Park, NC.
43 Product Information. Stribild (cobicistat/elvitegravir/emtricitabine/tenofov). Gilead Sciences, Foster City, CA.
44 Anson BD, Weaver JG, Ackerman MJ, et al. "Blockade of HERG channels by HIV protease inhibitors." Lancet 365 (2005): 682-686. [PMID: 15721475]
45 Product Information. Givlaari (givosiran). Alnylam Pharmaceuticals, Cambridge, MA.
46 Product Information. Orladeyo (berotralstat). BioCryst Pharmaceuticals Inc, Durham, NC.
47 Product Information. Xalkori (crizotinib). Pfizer U.S. Pharmaceuticals Group, New York, NY.
48 Product Information. Vizimpro (dacomitinib). Pfizer U.S. Pharmaceuticals Group, New York, NY.
49 Product Information. Tagrisso (osimertinib). Astra-Zeneca Pharmaceuticals, Wilmington, DE.
50 Product Information. Retevmo (selpercatinib). Lilly, Eli and Company, Indianapolis, IN.
51 Abernethy DR, Wesche DL, Barbey JT, et al. "Stereoselective halofantrine disposition and effect: concentration-related QTc prolongation." Br J Clin Pharmacol 51 (2001): 231-7. [PMID: 11298069]
52 Product Information. Hydroxychloroquine Sulfate (hydroxychloroquine). Prasco Laboratories, Cincinnati, OH.
53 Ohnishi K, Yoshida H, Shigeno K, et al. "Prolongation of the QT interval and ventricular tachycardia in patients treated with arsenic trioxide for acute promyelocytic leukemia." Ann Intern Med 133 (2000): 881-5. [PMID: 11103058]
54 Product Information. Braftovi (encorafenib). Array BioPharma Inc., Boulder, CO.
55 Product Information. Zulresso (brexanolone). Sage Therapeutics, Inc., Cambridge, MA.
56 Product Information. Addyi (flibanserin). Sprout Pharmaceuticals, Raleigh, NC.
57 Product Information. Farydak (panobinostat). Novartis Pharmaceuticals, East Hanover, NJ.
58 Alvine G, Black DW, Tsuang D "Case of delirium secondary to phenelzine/L-tryptophan combination." J Clin Psychiatry 51 (1990): 311. [PMID: 2365671]
59 Product Information. Varubi (rolapitant). Tesaro Inc., Waltham, MA.
60 James WA, Lippmann S "Bupropion: overview and prescribing guidelines in depression." South Med J 84 (1991): 222-4. [PMID: 1899294]
61 Product Information. Belviq (lorcaserin). Eisai Inc, Teaneck, NJ.
62 Morgan JP, Rivera-Calimlim L, Messiha F, Sundaresan PR, Trabert N "Imipramine-mediated interference with levodopa absorption from the gastrointestinal tract in man." Neurology 25 (1975): 1029-34. [PMID: 1237820]
63 Product Information. Nuplazid (pimavanserin). Accelis Pharma, East Windsor, NJ.
64 Product Information. Xenleta (lefamulin). Nabriva Therapeutics US, Inc., King of Prussia, PA.
65 Product Information. Zytiga (abiraterone). Centocor Inc, Malvern, PA.
66 Bock JL, Nelson JC, Gray S, Jatlow PI "Desipramine hydroxylation: variability and effect of antipsychotic drugs." Clin Pharmacol Ther 33 (1983): 322-8. [PMID: 6130865]
67 Product Information. Barhemsys (amisulpride). Acacia Pharma, Inc, Indianapolis, IN.
68 Lee BS "Possibility of hyperpyrexia with antipsychotic and anticholinergic drugs." J Clin Psychiatry 47 (1986): 571. [PMID: 3771507]
69 Katz MR "Raised serum levels of desipramine with the antiarrhythmic propafenone ." J Clin Psychiatry 52 (1991): 432-3. [PMID: 1938981]