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

General Information of Drug (ID: DR3394)
Drug Name
Atorvastatin
Synonyms
atorvastatin; 134523-00-5; Cardyl; Xavator; Tozalip; Lipitor; Torvast; Sotis; ATORVASTATIN CALCIUM; Atorvastatin [INN:BAN]; 110862-48-1; UNII-A0JWA85V8F; CCRIS 7159; C33H35FN2O5; HSDB 7039; CI 981; Lipitor (TN); CHEMBL1487; A0JWA85V8F; CHEBI:39548; (betaR,deltaR)-2-(p-Fluorophenyl)-b; Atorvastatin
Indication Hypertriglyceridaemia [ICD11: 5C80] Approved [1]
Coronavirus Disease 2019 (COVID-19) [ICD11: ICD11: 1D6Y] Phase 2 [2]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 558.6 Topological Polar Surface Area 112
Heavy Atom Count 41 Rotatable Bond Count 12
Hydrogen Bond Donor Count 4 Hydrogen Bond Acceptor Count 6
Cross-matching ID
PubChem CID
60823
ChEBI ID
CHEBI:39548
CAS Number
134523-00-5
TTD Drug ID
D07TSV
Formula
C33H35FN2O5
Canonical SMILES
CC(C)C1=C(C(=C(N1CC[C@H](C[C@H](CC(=O)O)O)O)C2=CC=C(C=C2)F)C3=CC=CC=C3)C(=O)NC4=CC=CC=C4
InChI
InChI=1S/C33H35FN2O5/c1-21(2)31-30(33(41)35-25-11-7-4-8-12-25)29(22-9-5-3-6-10-22)32(23-13-15-24(34)16-14-23)36(31)18-17-26(37)19-27(38)20-28(39)40/h3-16,21,26-27,37-38H,17-20H2,1-2H3,(H,35,41)(H,39,40)/t26-,27-/m1/s1
InChIKey
XUKUURHRXDUEBC-KAYWLYCHSA-N
The Predicted Metabolic Roadmap of This Drug
The Full List of Predicted Drug Metabolites (PDM) of This Drug
PDM Name PDM ID PubChem ID Reaction PDM Level Biosystem
Atorvastatin M1 PDM014642 N. A. Conjugation - Glycine conjugation 1 Human
Atorvastatin M2 PDM014643 N. A. Conjugation - Alkyl-OH-glucuronidation 1 Human
Atorvastatin M3 PDM014644 N. A. Conjugation - Alkyl-OH-glucuronidation 1 Human
Atorvastatin M4 PDM014645 N. A. Conjugation - O-Glucuronidation of aliphatic acid 1 Human
Atorvastatin M5 PDM014646 N. A. Conjugation - Sulfation of secondary alcohol 1 Human
Atorvastatin M6 PDM014647 N. A. Conjugation - Sulfation of secondary alcohol 1 Human
Atorvastatin M7 PDM014648 N. A. Conjugation - Carnitine conjugation 1 Human
Atorvastatin M8 PDM014649 N. A. Oxidation - alpha-Oxidation of carboxylic acid 1 Gut microbial environment
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2C8 (CYP2C8) DME0018 Homo sapiens
CP2C8_HUMAN
1.14.14.1
[3]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[4]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[5]
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME0004 Homo sapiens
UD11_HUMAN
2.4.1.17
[6]
UDP-glucuronosyltransferase 1A3 (UGT1A3) DME0041 Homo sapiens
UD13_HUMAN
2.4.1.17
[6]
References
1 FDA Approved Drug Products from FDA Official Website. 2019. Application Number: (ANDA) 205945.
2 ClinicalTrials.gov (NCT04380402) Atorvastatin in COVID-19. U.S. National Institutes of Health.
3 Comparison of 3-hydroxy-3-methylglutaryl coenzyme A (HMG-CoA) reductase inhibitors (statins) as inhibitors of cytochrome P450 2C8. Basic Clin Pharmacol Toxicol. 2005 Aug;97(2):104-8.
4 Drug interactions with lipid-lowering drugs: mechanisms and clinical relevance. Clin Pharmacol Ther. 2006 Dec;80(6):565-81.
5 Lactonization is the critical first step in the disposition of the 3-hydroxy-3-methylglutaryl-CoA reductase inhibitor atorvastatin. Drug Metab Dispos. 2000 Nov;28(11):1369-78.
6 UGT1A1*28 is associated with decreased systemic exposure of atorvastatin lactone. Mol Diagn Ther. 2013 Aug;17(4):233-7.

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