Details of the Drug

General Information of Drug (ID: DM1UJO0)

Drug Name
PITAVASTATIN CALCIUM
Synonyms
Livalo; Pitavastatin calcium; 147526-32-7; Pitavastatin hemicalcium; NK-104; Nisvastatin; UNII-IYD54XEG3W; Flovas; IYD54XEG3W; 2C25H23FNO4Ca; CHEBI:71258; NK 104 (acid); Calcium (3R,5S,E)-7-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-3,5-dihydroxyhept-6-enoate; AK-50694; Itavastatin calcium; Bis((3R,5S,6E)-7-(2-cyclopropyl-4-(4-fluorophenyl)-3-quinolyl)-3,5-dihydroxy-6-heptenoate), monocalcium salt; Pitavastatin calcium (JAN); Alipza; Livazo; P-872441; P 872441; 6-Heptenoic acid,
Indication
Disease Entry ICD 11 Status REF
Dyslipidemia 5C80-5C81 Approved [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski):
3		 Molecular Weight 881
Logarithm of the Partition Coefficient Not Available
Rotatable Bond Count 14
Hydrogen Bond Donor Count 4
Hydrogen Bond Acceptor Count 12
Chemical Identifiers
Formula
C50H46CaF2N2O8
IUPAC Name
calcium;(E,3R,5S)-7-[2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl]-3,5-dihydroxyhept-6-enoate
Canonical SMILES
C1C(C1)C2=NC3=CC=CC=C3C(=C2/C=C/[C@@H](O)C[C@@H](O)CC(=O)[O-])C4=CC=C(C=C4)F.C1C(C1)C2=NC3=CC=CC=C3C(=C2/C=C/[C@@H](O)C[C@@H](O)CC(=O)[O-])C4=CC=C(C=C4)F.[Ca+2]
InChI
InChI=1S/2C25H24FNO4.Ca/c2*26-17-9-7-15(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;/h2*1-4,7-12,16,18-19,28-29H,5-6,13-14H2,(H,30,31);/q;;+2/p-2/b2*12-11+;/t2*18-,19-;/m11./s1
InChIKey
RHGYHLPFVJEAOC-FFNUKLMVSA-L
Cross-matching ID
PubChem CID
5282451
ChEBI ID
CHEBI:71258
CAS Number
147526-32-7
TTD ID
D0G1WL
VARIDT ID
DR00206
INTEDE ID
DR1306
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
HMG-CoA reductase (HMGCR) TTPADOQ HMDH_HUMAN Inhibitor [2]

Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
Sodium/taurocholate cotransporting polypeptide (SLC10A1) DT56EKP NTCP_HUMAN Substrate [3]
Multidrug resistance-associated protein 2 (ABCC2) DTFI42L MRP2_HUMAN Substrate [4]
Organic anion transporting polypeptide 2B1 (SLCO2B1) DTPFTEQ SO2B1_HUMAN Substrate [5]
Organic anion transporting polypeptide 1A2 (SLCO1A2) DTE2B1D SO1A2_HUMAN Substrate [3]
Breast cancer resistance protein (ABCG2) DTI7UX6 ABCG2_HUMAN Substrate [6]
Organic anion transporting polypeptide 1B1 (SLCO1B1) DT3D8F0 SO1B1_HUMAN Substrate [7]
Organic anion transporting polypeptide 1B3 (SLCO1B3) DT9C1TS SO1B3_HUMAN Substrate [8]
Organic anion transporter 3 (SLC22A8) DTVP67E S22A8_HUMAN Substrate [3]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 2C9 (CYP2C9) DE5IED8 CP2C9_HUMAN Substrate [9]
UDP-glucuronosyltransferase 1A1 (UGT1A1) DEYGVN4 UD11_HUMAN Substrate [10]
Cytochrome P450 2C8 (CYP2C8) DES5XRU CP2C8_HUMAN Substrate [11]
UDP-glucuronosyltransferase 2B7 (UGT2B7) DEB3CV1 UD2B7_HUMAN Substrate [9]
UDP-glucuronosyltransferase 1A3 (UGT1A3) DEF2WXN UD13_HUMAN Substrate [9]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Dyslipidemia
ICD Disease Classification 5C80-5C81
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
HMG-CoA reductase (HMGCR) DTT HMGCR 1.01E-05 0.65 1.53
Organic anion transporter 3 (SLC22A8) DTP OAT3 1.54E-03 -5.09E-01 -1.49E+00
Organic anion transporting polypeptide 2B1 (SLCO2B1) DTP OATP2B1 3.80E-01 -1.23E-02 -5.33E-02
Breast cancer resistance protein (ABCG2) DTP BCRP 2.28E-08 -3.66E-01 -8.07E-01
Multidrug resistance-associated protein 2 (ABCC2) DTP MRP2 4.30E-02 -2.29E-01 -9.10E-01
Organic anion transporting polypeptide 1A2 (SLCO1A2) DTP OATP1A2 7.28E-02 -7.13E-02 -4.55E-01
Organic anion transporting polypeptide 1B3 (SLCO1B3) DTP OATP1B3 1.65E-01 -6.07E-02 -3.77E-01
Sodium/taurocholate cotransporting polypeptide (SLC10A1) DTP NTCP 7.48E-02 -5.70E-02 -2.14E-01
Organic anion transporting polypeptide 1B1 (SLCO1B1) DTP OATP1B1 3.27E-01 -5.78E-02 -3.84E-01
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME UGT1A1 2.00E-01 5.79E-02 3.00E-01
Cytochrome P450 2C8 (CYP2C8) DME CYP2C8 1.47E-02 -1.13E-01 -1.13E+00
Cytochrome P450 2C9 (CYP2C9) DME CYP2C9 2.63E-03 -1.18E-01 -3.80E-01
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
2 Cholesterol-lowering effect of NK-104, a 3-hydroxy-3-methylglutaryl-coenzyme A reductase inhibitor, in guinea pig model of hyperlipidemia. Arzneimittelforschung. 2001;51(3):197-203.
3 Transporter-mediated influx and efflux mechanisms of pitavastatin, a new inhibitor of HMG-CoA reductase. J Pharm Pharmacol. 2005 Oct;57(10):1305-11.
4 Mammalian drug efflux transporters of the ATP binding cassette (ABC) family in multidrug resistance: A review of the past decade. Cancer Lett. 2016 Jan 1;370(1):153-64.
5 Drug-drug interaction between pitavastatin and various drugs via OATP1B1. Drug Metab Dispos. 2006 Jul;34(7):1229-36.
6 Involvement of BCRP (ABCG2) in the biliary excretion of pitavastatin. Mol Pharmacol. 2005 Sep;68(3):800-7.
7 The effect of SLCO1B1*15 on the disposition of pravastatin and pitavastatin is substrate dependent: the contribution of transporting activity changes by SLCO1B1*15. Pharmacogenet Genomics. 2008 May;18(5):424-33.
8 Contribution of OATP2 (OATP1B1) and OATP8 (OATP1B3) to the hepatic uptake of pitavastatin in humans. J Pharmacol Exp Ther. 2004 Oct;311(1):139-46.
9 Pitavastatin: a review in hypercholesterolemia. Am J Cardiovasc Drugs. 2017 Apr;17(2):157-168.
10 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.
11 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.