Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2020-02-26 21:40:07 UTC
HMDB IDHMDB0014680
Secondary Accession Numbers
  • HMDB14680
Metabolite Identification
Common NameNortriptyline
DescriptionNortriptyline hydrochloride, the N-demethylated active metabolite of amitriptyline, is a dibenzocycloheptene-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, nortriptyline does not affect mood or arousal, but may cause sedation. In depressed individuals, nortriptyline exerts a positive effect on mood. TCAs are potent inhibitors of serotonin and norepinephrine reuptake. Secondary amine TCAs, such as nortriptyline, are more potent inhibitors of norepinephrine reuptake than tertiary amine TCAs, such as amitriptyline. 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. See toxicity section below for a complete listing of side effects. Nortriptyline exerts less anticholinergic and sedative side effects compared to the tertiary amine TCAs, amitriptyline and clomipramine. Nortriptyline may be used to treat depression, chronic pain (unlabeled use), irritable bowel syndrome (unlabeled use), diabetic neuropathy (unlabeled use), post-traumatic stress disorder (unlabeled use), and for migraine prophylaxis (unlabeled use).
Structure
Data?1582753207
Synonyms
ValueSource
10,11-Dihydro-N-methyl-5H-dibenzo[a,D]cycloheptene-Delta(5,gamma)-propylamineChEBI
3-(10,11-Dihydro-5H-dibenzo[a,D]cyclohepten-5-ylidene)-N-methyl-1-propanamineChEBI
AtebenChEBI
AvantylChEBI
AventylChEBI
DemethylamitriptylineChEBI
DesmethylamitriptylineChEBI
NoritrenChEBI
NortriptylinaChEBI
NortriptylinumChEBI
PsychostylChEBI
SensavalChEBI
NortrilenKegg
10,11-Dihydro-N-methyl-5H-dibenzo[a,D]cycloheptene-delta(5,g)-propylamineGenerator
10,11-Dihydro-N-methyl-5H-dibenzo[a,D]cycloheptene-δ(5,γ)-propylamineGenerator
10,11-Dihydro-N-methyl-5H-dibenzo[a,D]cycloheptene-δ(5,g)-propylamineHMDB
Apo nortriptylineHMDB
DesmethylamitriptylinHMDB
Gen nortriptylineHMDB
Lundbeck brand OF nortriptyline hydrochlorideHMDB
Novo nortriptylineHMDB
Novopharm brand OF nortriptyline hydrochlorideHMDB
Reig jofre brand OF nortriptyline hydrochlorideHMDB
Apotex brand OF nortriptyline hydrochlorideHMDB
Genpharm brand OF nortriptyline hydrochlorideHMDB
Hydrochloride, nortriptylineHMDB
Nortriptyline hydrochlorideHMDB
Novo-nortriptylineHMDB
PMS-NortriptylineHMDB
Ratio nortriptylineHMDB
AllegronHMDB
Apo-nortriptylineHMDB
Dista brand OF nortriptyline hydrochlorideHMDB
Gen-nortriptylineHMDB
Lilly brand OF nortriptyline hydrochlorideHMDB
Nu-pharm brand OF nortriptyline hydrochlorideHMDB
PMS NortriptylineHMDB
PamelorHMDB
Pharmascience brand OF nortriptyline hydrochlorideHMDB
DesitriptylineHMDB
Mallinckrodt brand OF nortriptyline hydrochlorideHMDB
NorfenazinHMDB
Nu nortriptylineHMDB
Nu pharm brand OF nortriptyline hydrochlorideHMDB
Nu-nortriptylineHMDB
PaxtibiHMDB
Ratiopharm brand OF nortriptyline hydrochlorideHMDB
Ratio-nortriptylineHMDB
Chemical FormulaC19H21N
Average Molecular Weight263.3767
Monoisotopic Molecular Weight263.167399677
IUPAC Namemethyl(3-{tricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,11,13-hexaen-2-ylidene}propyl)amine
Traditional Namenortriptyline
CAS Registry Number72-69-5
SMILES
CNCCC=C1C2=CC=CC=C2CCC2=CC=CC=C12
InChI Identifier
InChI=1S/C19H21N/c1-20-14-6-11-19-17-9-4-2-7-15(17)12-13-16-8-3-5-10-18(16)19/h2-5,7-11,20H,6,12-14H2,1H3
InChI KeyPHVGLTMQBUFIQQ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dibenzocycloheptenes. Dibenzocycloheptenes are compounds containing a dibenzocycloheptene moiety, which consists of two benzene rings connected by a cycloheptene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassDibenzocycloheptenes
Sub ClassNot Available
Direct ParentDibenzocycloheptenes
Alternative Parents
Substituents
  • Dibenzocycloheptene
  • Secondary amine
  • Secondary aliphatic amine
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Amine
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Ontology
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point213 - 215 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.00087 g/LNot Available
LogP4.7Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available163.081http://allccs.zhulab.cn/database/detail?ID=AllCCS00000745
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.00087 g/LALOGPS
logP4.65ALOGPS
logP4.43ChemAxon
logS-5.5ALOGPS
pKa (Strongest Basic)10.47ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area12.03 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity96.21 m³·mol⁻¹ChemAxon
Polarizability31.87 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+163.26131661259
DarkChem[M-H]-163.85531661259
DeepCCS[M-2H]-191.8830932474
DeepCCS[M+Na]+167.44530932474
AllCCS[M+H]+164.332859911
AllCCS[M+H-H2O]+160.732859911
AllCCS[M+NH4]+167.732859911
AllCCS[M+Na]+168.732859911
AllCCS[M-H]-171.532859911
AllCCS[M+Na-2H]-171.132859911
AllCCS[M+HCOO]-170.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
NortriptylineCNCCC=C1C2=CC=CC=C2CCC2=CC=CC=C123057.3Standard polar33892256
NortriptylineCNCCC=C1C2=CC=CC=C2CCC2=CC=CC=C122241.2Standard non polar33892256
NortriptylineCNCCC=C1C2=CC=CC=C2CCC2=CC=CC=C122219.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Nortriptyline,1TMS,isomer #1CN(CCC=C1C2=CC=CC=C2CCC2=CC=CC=C12)[Si](C)(C)C2529.5Semi standard non polar33892256
Nortriptyline,1TMS,isomer #1CN(CCC=C1C2=CC=CC=C2CCC2=CC=CC=C12)[Si](C)(C)C2579.1Standard non polar33892256
Nortriptyline,1TMS,isomer #1CN(CCC=C1C2=CC=CC=C2CCC2=CC=CC=C12)[Si](C)(C)C2942.5Standard polar33892256
Nortriptyline,1TBDMS,isomer #1CN(CCC=C1C2=CC=CC=C2CCC2=CC=CC=C12)[Si](C)(C)C(C)(C)C2731.5Semi standard non polar33892256
Nortriptyline,1TBDMS,isomer #1CN(CCC=C1C2=CC=CC=C2CCC2=CC=CC=C12)[Si](C)(C)C(C)(C)C2848.1Standard non polar33892256
Nortriptyline,1TBDMS,isomer #1CN(CCC=C1C2=CC=CC=C2CCC2=CC=CC=C12)[Si](C)(C)C(C)(C)C3050.1Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Nortriptyline EI-B (Non-derivatized)splash10-0006-9000000000-bb9eae4818c0402317ee2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Nortriptyline EI-B (Non-derivatized)splash10-0006-9000000000-bb9eae4818c0402317ee2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Nortriptyline GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9040000000-03aa30e0f3d1715d991e2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Nortriptyline GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Nortriptyline GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0006-9230000000-15f73e5232a0e230f41b2014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Nortriptyline LC-ESI-QTOF , positive-QTOFsplash10-05nf-5970000000-f92c7d23474b57a4ba502017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nortriptyline LC-ESI-QFT , positive-QTOFsplash10-03di-0090000000-4c40cb3ec4df8809981e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nortriptyline LC-ESI-QFT , positive-QTOFsplash10-06sl-2590000000-be2abd28b2b0f75dd8bb2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nortriptyline LC-ESI-QFT , positive-QTOFsplash10-05mo-3940000000-6a454924ec75665c61752017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nortriptyline LC-ESI-QFT , positive-QTOFsplash10-05mo-3930000000-eb8141866b19782dd1e52017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nortriptyline LC-ESI-QFT , positive-QTOFsplash10-00kf-4930000000-81614e655fc32d5839ce2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nortriptyline LC-ESI-QFT , positive-QTOFsplash10-00kf-4930000000-f918306a99d07f8875032017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nortriptyline LC-ESI-QFT , positive-QTOFsplash10-0gdl-5930000000-d876ab376d0e9885d06d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nortriptyline LC-ESI-QFT , positive-QTOFsplash10-0gb9-5930000000-e51a246750bf8ce7e4ec2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nortriptyline LC-ESI-QFT , positive-QTOFsplash10-0gbi-5930000000-c2811578219a3a7e1ccf2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nortriptyline , positive-QTOFsplash10-03yi-0490000000-094e7bdb831aed030f5f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nortriptyline 75V, Positive-QTOFsplash10-00kf-4930000000-fb69faeba7a357c5bc5a2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nortriptyline 90V, Positive-QTOFsplash10-00kf-4930000000-76afa553a0a96ca361962021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nortriptyline 30V, Positive-QTOFsplash10-06sl-2590000000-8294a4644460a638747b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nortriptyline 15V, Positive-QTOFsplash10-03di-0090000000-ff969015b0f97e8c78bc2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nortriptyline 45V, Positive-QTOFsplash10-05mo-3940000000-2244b5f59802d5d17a112021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nortriptyline 60V, Positive-QTOFsplash10-05mo-3930000000-ae25ca0dbf191a8decb72021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nortriptyline -1V, Positive-QTOFsplash10-05nf-5970000000-279d8674cee6125e13632021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nortriptyline 10V, Positive-QTOFsplash10-03e9-1090000000-0122fb1ff7e4f061277f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nortriptyline 20V, Positive-QTOFsplash10-01qc-3290000000-820f6bab951ae7e9352d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nortriptyline 40V, Positive-QTOFsplash10-0006-6950000000-d6a7a0dcc07c2ab8c35f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nortriptyline 10V, Negative-QTOFsplash10-03di-0090000000-6586d2d06dd2491b85d02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nortriptyline 20V, Negative-QTOFsplash10-03di-1090000000-3af72990a6e6a4c9e3ab2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nortriptyline 40V, Negative-QTOFsplash10-001l-4290000000-05af30a36ff956182b212016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nortriptyline 10V, Positive-QTOFsplash10-03di-0090000000-0f92e6ab1c1e69d00ae52021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00540 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00540 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00540
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4384
KEGG Compound IDC07274
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNortriptyline
METLIN IDNot Available
PubChem Compound4543
PDB IDNot Available
ChEBI ID7640
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Prochazka AV, Weaver MJ, Keller RT, Fryer GE, Licari PA, Lofaso D: A randomized trial of nortriptyline for smoking cessation. Arch Intern Med. 1998 Oct 12;158(18):2035-9. [PubMed:9778204 ]

Only showing the first 10 proteins. There are 20 proteins in total.

Enzymes

General function:
Involved in peroxidase activity
Specific function:
May play an important role in regulating or promoting cell proliferation in some normal and neoplastically transformed cells.
Gene Name:
PTGS1
Uniprot ID:
P23219
Molecular weight:
68685.82
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
General function:
Involved in monooxygenase 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 xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
References
  1. Wen B, Ma L, Zhu M: Bioactivation of the tricyclic antidepressant amitriptyline and its metabolite nortriptyline to arene oxide intermediates in human liver microsomes and recombinant P450s. Chem Biol Interact. 2008 May 9;173(1):59-67. doi: 10.1016/j.cbi.2008.02.001. Epub 2008 Feb 14. [PubMed:18359012 ]
  2. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
  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 ]
  4. Venkatakrishnan K, von Moltke LL, Greenblatt DJ: Nortriptyline E-10-hydroxylation in vitro is mediated by human CYP2D6 (high affinity) and CYP3A4 (low affinity): implications for interactions with enzyme-inducing drugs. J Clin Pharmacol. 1999 Jun;39(6):567-77. [PubMed:10354960 ]
General function:
Involved in monooxygenase 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, phenytoin, tolbutamide and losartan.
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular weight:
55627.365
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
General function:
Involved in monooxygenase 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:
55944.565
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
  2. 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 ]
  3. Olesen OV, Linnet K: Hydroxylation and demethylation of the tricyclic antidepressant nortriptyline by cDNA-expressed human cytochrome P-450 isozymes. Drug Metab Dispos. 1997 Jun;25(6):740-4. [PubMed:9193876 ]
General function:
Involved in monooxygenase activity
Specific function:
Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic or carcinogenic forms.
Gene Name:
CYP2E1
Uniprot ID:
P05181
Molecular weight:
56848.42
References
  1. 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 ]
General function:
Involved in monooxygenase 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
References
  1. Wen B, Ma L, Zhu M: Bioactivation of the tricyclic antidepressant amitriptyline and its metabolite nortriptyline to arene oxide intermediates in human liver microsomes and recombinant P450s. Chem Biol Interact. 2008 May 9;173(1):59-67. doi: 10.1016/j.cbi.2008.02.001. Epub 2008 Feb 14. [PubMed:18359012 ]
  2. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
  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 ]
  4. Venkatakrishnan K, von Moltke LL, Greenblatt DJ: Nortriptyline E-10-hydroxylation in vitro is mediated by human CYP2D6 (high affinity) and CYP3A4 (low affinity): implications for interactions with enzyme-inducing drugs. J Clin Pharmacol. 1999 Jun;39(6):567-77. [PubMed:10354960 ]
  5. Olesen OV, Linnet K: Hydroxylation and demethylation of the tricyclic antidepressant nortriptyline by cDNA-expressed human cytochrome P-450 isozymes. Drug Metab Dispos. 1997 Jun;25(6):740-4. [PubMed:9193876 ]
General function:
Involved in monooxygenase 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.
Gene Name:
CYP3A5
Uniprot ID:
P20815
Molecular weight:
57108.065
References
  1. Wen B, Ma L, Zhu M: Bioactivation of the tricyclic antidepressant amitriptyline and its metabolite nortriptyline to arene oxide intermediates in human liver microsomes and recombinant P450s. Chem Biol Interact. 2008 May 9;173(1):59-67. doi: 10.1016/j.cbi.2008.02.001. Epub 2008 Feb 14. [PubMed:18359012 ]
General function:
Involved in monooxygenase 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. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:
CYP1A2
Uniprot ID:
P05177
Molecular weight:
58406.915
References
  1. Wen B, Ma L, Zhu M: Bioactivation of the tricyclic antidepressant amitriptyline and its metabolite nortriptyline to arene oxide intermediates in human liver microsomes and recombinant P450s. Chem Biol Interact. 2008 May 9;173(1):59-67. doi: 10.1016/j.cbi.2008.02.001. Epub 2008 Feb 14. [PubMed:18359012 ]
  2. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
  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 ]
  4. Olesen OV, Linnet K: Hydroxylation and demethylation of the tricyclic antidepressant nortriptyline by cDNA-expressed human cytochrome P-450 isozymes. Drug Metab Dispos. 1997 Jun;25(6):740-4. [PubMed:9193876 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
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 inhibit adenylate cyclase activity
Gene Name:
HTR1A
Uniprot ID:
P08908
Molecular weight:
46106.3
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 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
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. This receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. This receptor is involved in tracheal smooth muscle contraction, bronchoconstriction, and control of aldosterone production
Gene Name:
HTR2A
Uniprot ID:
P28223
Molecular weight:
52602.6
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 ]

Transporters

General function:
Involved in neurotransmitter: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
References
  1. Roubert C, Cox PJ, Bruss M, Hamon M, Bonisch H, Giros B: Determination of residues in the norepinephrine transporter that are critical for tricyclic antidepressant affinity. J Biol Chem. 2001 Mar 16;276(11):8254-60. Epub 2000 Nov 22. [PubMed:11092898 ]
  2. Roubert C, Sagne C, Kapsimali M, Vernier P, Bourrat F, Giros B: A Na(+)/Cl(-)-dependent transporter for catecholamines, identified as a norepinephrine transporter, is expressed in the brain of the teleost fish medaka (Oryzias latipes). Mol Pharmacol. 2001 Sep;60(3):462-73. [PubMed:11502876 ]
  3. Vaishnavi SN, Nemeroff CB, Plott SJ, Rao SG, Kranzler J, Owens MJ: Milnacipran: a comparative analysis of human monoamine uptake and transporter binding affinity. Biol Psychiatry. 2004 Feb 1;55(3):320-2. [PubMed:14744476 ]
  4. Kim H, Lim SW, Kim S, Kim JW, Chang YH, Carroll BJ, Kim DK: Monoamine transporter gene polymorphisms and antidepressant response in koreans with late-life depression. JAMA. 2006 Oct 4;296(13):1609-18. [PubMed:17018806 ]
  5. Barker EL, Blakely RD: Identification of a single amino acid, phenylalanine 586, that is responsible for high affinity interactions of tricyclic antidepressants with the human serotonin transporter. Mol Pharmacol. 1996 Oct;50(4):957-65. [PubMed:8863842 ]
  6. 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 ]
General function:
Involved in neurotransmitter: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 and recycles it in a sodium-dependent manner.
Gene Name:
SLC6A4
Uniprot ID:
P31645
Molecular weight:
70324.165
References
  1. Joyce PR, Mulder RT, Luty SE, McKenzie JM, Miller AL, Rogers GR, Kennedy MA: Age-dependent antidepressant pharmacogenomics: polymorphisms of the serotonin transporter and G protein beta3 subunit as predictors of response to fluoxetine and nortriptyline. Int J Neuropsychopharmacol. 2003 Dec;6(4):339-46. [PubMed:14604448 ]
  2. Wisner KL, Hanusa BH, Perel JM, Peindl KS, Piontek CM, Sit DK, Findling RL, Moses-Kolko EL: Postpartum depression: a randomized trial of sertraline versus nortriptyline. J Clin Psychopharmacol. 2006 Aug;26(4):353-60. [PubMed:16855451 ]
  3. Pollock BG, Ferrell RE, Mulsant BH, Mazumdar S, Miller M, Sweet RA, Davis S, Kirshner MA, Houck PR, Stack JA, Reynolds CF, Kupfer DJ: Allelic variation in the serotonin transporter promoter affects onset of paroxetine treatment response in late-life depression. Neuropsychopharmacology. 2000 Nov;23(5):587-90. [PubMed:11027924 ]
  4. Vaishnavi SN, Nemeroff CB, Plott SJ, Rao SG, Kranzler J, Owens MJ: Milnacipran: a comparative analysis of human monoamine uptake and transporter binding affinity. Biol Psychiatry. 2004 Feb 1;55(3):320-2. [PubMed:14744476 ]
  5. Rausch JL, Moeller FG, Johnson ME: Initial platelet serotonin (5-HT) transport kinetics predict nortriptyline treatment outcome. J Clin Psychopharmacol. 2003 Apr;23(2):138-44. [PubMed:12640215 ]
  6. 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 ]

Only showing the first 10 proteins. There are 20 proteins in total.