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

General Information of Drug (ID: DR1327)
Drug Name
Pravastatin
Synonyms
Pravachol; Pravastatin [INN:BAN]; Pravastatin acid; Pravastatina; Pravastatina [Spanish]; Pravastatine; Pravastatine [French]; Pravastatinum; Pravastatinum [Latin]; Vasten; Eptastatin; KXO2KT9N0G; PRAVASTATIN SODIUM; pravastatin; (3R,5R)-3,5-dihydroxy-7-[(1S,2S,6S,8S,8aR)-6-hydroxy-2-methyl-8-{[(2S)-2-methylbutanoyl]oxy}-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]heptanoic acid; 81093-37-0; CCRIS 7557; CHEBI:63618; CHEMBL1144; UNII-KXO2KT9N0G
Indication Dyslipidaemia [ICD11: 5C81] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 424.5 Topological Polar Surface Area 124
Heavy Atom Count 30 Rotatable Bond Count 11
Hydrogen Bond Donor Count 4 Hydrogen Bond Acceptor Count 7
Cross-matching ID
PubChem CID
54687
PubChem SID
4962 ; 7980374 ; 8183732 ; 10852022 ; 14758460 ; 14880512 ; 34718661 ; 46504851 ; 48416457 ; 49688762 ; 49995722 ; 50718915 ; 57288813 ; 57313644 ; 85789083 ; 85856288 ; 93166931 ; 96025096 ; 102979949 ; 104234199 ; 104305598 ; 117544687 ; 118048679 ; 124899367 ; 126665388 ; 129317935 ; 134337841 ; 135014686 ; 135610132 ; 135650848 ; 137002685 ; 142742106 ; 152034648 ; 152164597 ; 160963523 ; 164814679 ; 165235255 ; 174007284 ; 175266850 ; 175426985 ; 175612187 ; 179148899 ; 184545482 ; 187072512 ; 210279284 ; 210281607 ; 223554816 ; 223682192 ; 223745588 ; 226393956
ChEBI ID
CHEBI:63618
CAS Number
81093-37-0
TTD Drug ID
D02RQU
Formula
C23H36O7
Canonical SMILES
CCC(C)C(=O)OC1CC(C=C2C1C(C(C=C2)C)CCC(CC(CC(=O)O)O)O)O
InChI
1S/C23H36O7/c1-4-13(2)23(29)30-20-11-17(25)9-15-6-5-14(3)19(22(15)20)8-7-16(24)10-18(26)12-21(27)28/h5-6,9,13-14,16-20,22,24-26H,4,7-8,10-12H2,1-3H3,(H,27,28)/t13-,14-,16+,17+,18+,19-,20-,22-/m0/s1
InChIKey
TUZYXOIXSAXUGO-PZAWKZKUSA-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
3'(S)-hydroxy-pravastatin DM002909
139033201
Oxidation - Oxidation 1 [4]
3'(S)-hydroxy-pravastatin-tetranor DM002907 N. A. Oxidation - Oxidation 1 [4]
3alpha-isopravastatin DM002899
45039495
Other reaction - Isomerization 1 [5] , [6] , [4]
6-epi-pravastatin DM002902
42630641
Other reaction - Isomerization 1 [4]
Desacylpravastatin DM002903
58746970
Oxidation - Oxidation 1 [4]
Pravastatin glucuronide DM002904 N. A. Conjugation - Glucuronidation 1 [4]
Triol pravastatin DM002905
63012
Oxidation - Hydroxylation 1 [4]
3'(S)-hydroxy-pravastatin-tetranor DM002907 N. A. Oxidation - Oxidation 2 [4]
3'(S)-hydroxy-pravastatin-tetranor glucuronide DM002908 N. A. Conjugation - Glucuronidation 2 [4]
3-keto-5,6-diol pravastatin DM002906 N. A. Oxidation - Oxidation 2 [4]
5,6-epoxy-3alpha-isopravastatin DM002900 N. A. Oxidation - Oxidation 2 [5] , [6] , [4]
7-hydroxy-3alpha-isopravastatin DM002901 N. A. Oxidation - Oxidation 2 [5] , [6] , [4]
⏷ Show the Full List of 12  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR002097 Pravastatin 3alpha-isopravastatin Other reaction - Isomerization Unclear [5], [6], [4]
MR002098 Pravastatin 6-epi-pravastatin Other reaction - Isomerization Unclear [4]
MR002099 Pravastatin Desacylpravastatin Oxidation - Oxidation Unclear [4]
MR002100 Pravastatin Pravastatin glucuronide Conjugation - Glucuronidation Unclear [4]
MR002101 Pravastatin Triol pravastatin Oxidation - Hydroxylation Unclear [4]
MR002102 Pravastatin 3'(S)-hydroxy-pravastatin-tetranor Oxidation - Oxidation Unclear [4]
MR002103 Pravastatin 3'(S)-hydroxy-pravastatin Oxidation - Oxidation Unclear [4]
MR002096 3'(S)-hydroxy-pravastatin 3'(S)-hydroxy-pravastatin-tetranor Oxidation - Oxidation Unclear [4]
MR002095 3'(S)-hydroxy-pravastatin-tetranor 3'(S)-hydroxy-pravastatin-tetranor glucuronide Conjugation - Glucuronidation Unclear [4]
MR002092 3alpha-isopravastatin 5,6-epoxy-3alpha-isopravastatin Oxidation - Oxidation Unclear [5], [6], [4]
MR002093 3alpha-isopravastatin 7-hydroxy-3alpha-isopravastatin Oxidation - Oxidation Unclear [5], [6], [4]
MR002094 Triol pravastatin 3-keto-5,6-diol pravastatin Oxidation - Oxidation Unclear [4]
⏷ Show the Full List of 12 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[2]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[3]
References
1 Pravastatin was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 In vitro comparative inhibition profiles of major human drug metabolising cytochrome P450 isozymes (CYP2C9, CYP2D6 and CYP3A4) by HMG-CoA reductase inhibitors. Eur J Clin Pharmacol. 1996;50(3):209-15.
3 Comparison of cytochrome P-450-dependent metabolism and drug interactions of the 3-hydroxy-3-methylglutaryl-CoA reductase inhibitors lovastatin and pravastatin in the liver. Drug Metab Dispos. 1999 Feb;27(2):173-9.
4 Disposition and metabolism of pravastatin sodium in rats, dogs and monkeys Eur J Drug Metab Pharmacokinet. 1992 Apr-Jun;17(2):103-13. doi: 10.1007/BF03188778.
5 Liquid chromatography-tandem mass spectrometric assay for pravastatin and two isomeric metabolites in mouse plasma and tissue homogenates J Chromatogr B Analyt Technol Biomed Life Sci. 2010 Oct 15;878(28):2751-9. doi: 10.1016/j.jchromb.2010.08.015.
6 Effects of mineral oil administration on the pharmacokinetics, metabolism and pharmacodynamics of atorvastatin and pravastatin in mice and dogs Eur J Pharm Sci. 2021 Jun 1;161:105776. doi: 10.1016/j.ejps.2021.105776.

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