Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR1376)
Drug Name
Quetiapine fumarate
Synonyms
Quetiapine fumarate [USAN]; Quetiapine hemifumarate; Quetiapine [INN:BAN]; UNII-BGL0JSY5SI; URKOMYMAXPYINW-UHFFFAOYSA-N; quetiapine; 111974-69-7; 2-(2-(4-Dibenzo(b,f)(1,4)thiazepin-11-yl-1-piperazinyl)ethoxy)ethanol; 2-[2-(4-Dibenzo[b,f][1,4]thiazepin-11-yl-1-piperazinyl)ethoxy]ethanol; 2-[2-(4-benzo[b][1,4]benzothiazepin-6-ylpiperazin-1-yl)ethoxy]ethanol; BGL0JSY5SI; C21H25N3O2S; CHEBI:8707; CHEMBL716; Co-Quetiapine; Ethanol, 2-[2-(4-dibenzo[b,f][1,4]thiazepin-11-yl-1-piperazinyl)ethoxy]-; NCGC00095911-03; Seroquel XR; UNII-2S3PL1B6UJ; ZD 5077; ZD5077; ZM 204,636; ZM 204636; 111974-72-2; 2-(2-(4-Dibenzo(b,f)(1,4)thiazepine-11-yl-1-piperazinyl)ethoxy)ethanol; 2-[2-(4-dibenzo[b,f][1,4]thiazepin-11-yl-1-piperazinyl)ethoxy]ethanol hemifumarate; 2S3PL1B6UJ; CHEBI:8708; Ethanol, 2-(2-(4-dibenzo(b,f)(1,4)thiazepin-11-yl-1-piperazinyl)ethoxy)-, (E)-2-butenedioate (2:1) (salt); ICI 204,636; ICI 204636; ICI-204636; MFCD03423782
Indication Schizophrenia [ICD11: 6A20] Approved [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 883.1 Topological Polar Surface Area 222
Heavy Atom Count 62 Rotatable Bond Count 14
Hydrogen Bond Donor Count 4 Hydrogen Bond Acceptor Count 14
Cross-matching ID
PubChem CID
5281025
ChEBI ID
CHEBI:8708
CAS Number
111974-72-2
TTD Drug ID
D0H7KF
Formula
C46H54N6O8S2
Canonical SMILES
C1CN(CCN1CCOCCO)C2=NC3=CC=CC=C3SC4=CC=CC=C42.C1CN(CCN1CCOCCO)C2=NC3=CC=CC=C3SC4=CC=CC=C42.C(=CC(=O)O)C(=O)O
InChI
1S/2C21H25N3O2S.C4H4O4/c2*25-14-16-26-15-13-23-9-11-24(12-10-23)21-17-5-1-3-7-19(17)27-20-8-4-2-6-18(20)22-21;5-3(6)1-2-4(7)8/h2*1-8,25H,9-16H2;1-2H,(H,5,6)(H,7,8)/b;;2-1+
InChIKey
ZTHJULTYCAQOIJ-WXXKFALUSA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
7-hydroxyquetiapine DM003031
132203
Oxidation - Hydroxylation 1 [5] , [3]
N-desalkylquetiapine DM003030
11369918
Unclear 1 [5] , [3]
O-desalkylquetiapine DM003033 N. A. Oxidation - N-Dealkylation 1 [5]
Quetiapine sulfoxide DM003032
10431050
Oxidation - Sulfoxidation 1 [5]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR002203 Quetiapine fumarate N-desalkylquetiapine Unclear CYP3A4 ... [5], [3]
MR002204 Quetiapine fumarate 7-hydroxyquetiapine Oxidation - Hydroxylation CYP3A4 ... [5], [3]
MR002205 Quetiapine fumarate Quetiapine sulfoxide Oxidation - Sulfoxidation CYP3A4 ... [5]
MR002206 Quetiapine fumarate O-desalkylquetiapine Oxidation - N-Dealkylation CYP3A4 ... [5]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[2]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[3]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[4]
Cytochrome P450 3A7 (CYP3A7) DME0015 Homo sapiens
CP3A7_HUMAN
1.14.14.1
[2]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[2]
References
1 Quetiapine Fumarate was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 A liquid chromatographic-electrospray-tandem mass spectrometric method for quantitation of quetiapine in human plasma and liver microsomes: application to study in vitro metabolism. J Anal Toxicol. 2004 Sep;28(6):443-8.
3 Metabolism of the active metabolite of quetiapine, N-desalkylquetiapine in vitro. Drug Metab Dispos. 2012 Sep;40(9):1778-84.
4 Influence of ABCB1 and CYP3A5 genetic polymorphisms on the pharmacokinetics of quetiapine in healthy volunteers. Pharmacogenet Genomics. 2014 Jan;24(1):35-42.
5 Metabolism of quetiapine by CYP3A4 and CYP3A5 in presence or absence of cytochrome B5. Drug Metab Dispos. 2009 Feb;37(2):254-8.

If you find any error in data or bug in web service, please kindly report it to Dr. Yin and Dr. Li.