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

General Information of Drug (ID: DR1306)
Drug Name
Pitavastatin calcium
Synonyms
Pitavastatin; Pitavastatin [INN]; Zypitamag; ( )-(3R,5S,6E)-7-(2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolyl)-3,5-dihydroxy-6-heptenoic acid; (3R,5S,6E)-7-(2-Cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-3,5-dihydroxyhept-6-enoic acid; (3R,5S,6E)-7-[2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl]-3,5-dihydroxyhept-6-enoic acid; C25H24FNO4; CHEBI:32020; UNII-M5681Q5F9P; Itavastatin; M5681Q5F9P; NK 104; Alipza; IYD54XEG3W; Itavastatin calcium; Livazo; Nisvastatin; Pitavastatin hemicalcium; 147526-32-7; 2C25H23FNO4.Ca; Bis((3R,5S,6E)-7-(2-cyclopropyl-4-(4-fluorophenyl)-3-quinolyl)-3,5-dihydroxy-6-heptenoate), monocalcium salt; CHEBI:71258; Calcium (3R,5S,E)-7-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-3,5-dihydroxyhept-6-enoate; UNII-IYD54XEG3W
Indication Hypertriglyceridaemia [ICD11: 5C80] Approved [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 881 Topological Polar Surface Area 187
Heavy Atom Count 63 Rotatable Bond Count 14
Hydrogen Bond Donor Count 4 Hydrogen Bond Acceptor Count 12
Cross-matching ID
PubChem CID
5282451
ChEBI ID
CHEBI:71258
CAS Number
147526-32-7
TTD Drug ID
D0G1WL
Formula
C50H46CaF2N2O8
Canonical SMILES
C1CC1C2=NC3=CC=CC=C3C(=C2C=CC(CC(CC(=O)[O-])O)O)C4=CC=C(C=C4)F.C1CC1C2=NC3=CC=CC=C3C(=C2C=CC(CC(CC(=O)[O-])O)O)C4=CC=C(C=C4)F.[Ca+2]
InChI
1S/C25H24FNO4.Ca/c26-17-9-7-15(8-10-17)24-20-3-1-2-4-22(20)27-25(16-5-6-16)21(24)12-11-18(28)13-19(29)14-23(30)31;/h1-4,7-12,16,18-19,28-29H,5-6,13-14H2,(H,30,31);/q;+2/b12-11+;/t18-,19-;/m1./s1
InChIKey
RHGYHLPFVJEAOC-FFNUKLMVSA-L
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
Pitavastatin DM002877
5282452
Unclear 1 [5]
M-13 DM002879
51351911
Oxidation - Oxidation 2 [5]
M-3 DM002878
57574064
Oxidation - Hydroxylation 2 [5]
Pitavastatin glucuronide DM002880
131881387
Conjugation - Glucuronidation 2 [5]
Pitavastatin lactone DM002881
9801294
Unclear 3 [5]
Pitavastatin DM002877
5282452
Hydrolysis - Hydrolysis 4 [5]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR002072 Pitavastatin calcium Pitavastatin Unclear Unclear [5]
MR002067 Pitavastatin M-3 Oxidation - Hydroxylation CYP3A4 [5]
MR002068 Pitavastatin M-13 Oxidation - Oxidation CYP2C8 ... [5]
MR002069 Pitavastatin Pitavastatin glucuronide Conjugation - Glucuronidation UGT1A1 ... [5]
MR002070 Pitavastatin glucuronide Pitavastatin lactone Unclear Unclear [5]
MR002071 Pitavastatin lactone Pitavastatin Hydrolysis - Hydrolysis Unclear [5]
⏷ Show the Full List of 6 MR(s)
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
[2]
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[3]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[4]
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME0004 Homo sapiens
UD11_HUMAN
2.4.1.17
[5]
UDP-glucuronosyltransferase 1A3 (UGT1A3) DME0041 Homo sapiens
UD13_HUMAN
2.4.1.17
[3]
UDP-glucuronosyltransferase 2B7 (UGT2B7) DME0040 Homo sapiens
UD2B7_HUMAN
2.4.1.17
[3]
Unclear metabolic mechanism (DME-unclear) DME1406 Collinsella aerofaciens Not Available Not Available [6]
⏷ Show the Full List of 7  DME(s)
References
1 Pitavastatin Calcium was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Comparison of the safety, tolerability, and pharmacokinetic profile of a single oral dose of pitavastatin 4 mg in adult subjects with severe renal impairment not on hemodialysis versus healthy adult subjects. J Cardiovasc Pharmacol. 2012 Jul;60(1):42-8.
3 Pitavastatin: a review in hypercholesterolemia. Am J Cardiovasc Drugs. 2017 Apr;17(2):157-168.
4 Metabolic fate of pitavastatin, a new inhibitor of HMG-CoA reductase: human UDP-glucuronosyltransferase enzymes involved in lactonization Xenobiotica. 2003 Jan;33(1):27-41. doi: 10.1080/0049825021000017957.
5 Metabolic fate of pitavastatin, a new inhibitor of HMG-CoA reductase: human UDP-glucuronosyltransferase enzymes involved in lactonization. Xenobiotica. 2003 Jan;33(1):27-41.
6 Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467.

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