Details of the Drug

General Information of Drug (ID: DMJH792)

Drug Name

Pitavastatin

Synonyms

Pitavastatin; Itavastatin; Livalo; NK 104; Pitavastatin [INN]; Pitavastatin calcium; UNII-M5681Q5F9P; NK-104; C25H24FNO4; M5681Q5F9P; Zypitamag; Flovas; (3R,5S,6E)-7-(2-Cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-3,5-dihydroxyhept-6-enoic acid; P 872441; P-872441; (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)-3-quinolyl)-3,5-dihydroxy-6-heptenoic acid; NK 104 (acid); Pitavastatin calcium (JAN)

Indication

Disease Entry	ICD 11	Status	REF
Hypercholesterolaemia	5C80.0	Approved	[1]
Hyperlipidemia, familial combined, LPL related	N.A.	Approved	[1]

Affected Organisms

Humans and other mammals

ATC Code

C10AA08: Pitavastatin

C10AA: HMG CoA reductase inhibitors

C10A: LIPID MODIFYING AGENTS, PLAIN

C10: LIPID MODIFYING AGENTS

C: CARDIOVASCULAR SYSTEM

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski):
0

Molecular Weight

421.5

Logarithm of the Partition Coefficient

Not Available

Rotatable Bond Count

Hydrogen Bond Donor Count

Hydrogen Bond Acceptor Count

ADMET Property

Absorption Tmax: The time to maximum plasma concentration (Tmax) is 1 h []
BDDCS Class: Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 4: low solubility and low permeability [2]
Clearance: The apparent oral clearance of drug is 43.4 L/h [3]
Elimination: A mean of 15% of radioactivity of orally administered, single 32 mg 14C-labeled pitavastatin dose was excreted in urine, whereas a mean of 79% of the dose was excreted in feces within 7 days []
Half-life: The concentration or amount of drug in body reduced by one-half in 12 hours []
Metabolism: The drug is metabolized via the liver uridine 5'-diphosphate glucuronosyltransferase (UGT) with subsequent formation of pitavastatin lactone []
Unbound Fraction: The unbound fraction of drug in plasma is 0.005% [4]
Vd: The volume of distribution (Vd) of drug is 148 L []

Chemical Identifiers

Formula: C25H24FNO4
IUPAC Name: (E,3R,5S)-7-[2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl]-3,5-dihydroxyhept-6-enoic acid
Canonical SMILES: C1CC1C2=NC3=CC=CC=C3C(=C2C=CC(CC(CC(=O)O)O)O)C4=CC=C(C=C4)F
InChI: InChI=1S/C25H24FNO4/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)/b12-11+/t18-,19-/m1/s1
InChIKey: VGYFMXBACGZSIL-MCBHFWOFSA-N

Cross-matching ID

PubChem CID: 5282452
ChEBI ID: CHEMBL1201753
CAS Number: 147511-69-1
UNII: M5681Q5F9P
DrugBank ID: DB08860
VARIDT ID: DR01545

Drug-Molecule Activity Atlas (DMA)^NEW

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Drug ADMET Endpoint Profile (DAE)^NEW

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Combinatorial Drugs (CBD)

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Repurposed Drugs (RPD)

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Molecular Interaction Atlas of This Drug

Drug Transporter (DTP)

DTP Name	DTP ID	UniProt ID	MOA	REF
Multidrug resistance-associated protein 2 (ABCC2)	DTFI42L	MRP2_HUMAN	Substrate	[5]
Organic anion transporting polypeptide 2B1 (SLCO2B1)	DTPFTEQ	SO2B1_HUMAN	Substrate	[6]
Organic anion transporting polypeptide 1A2 (SLCO1A2)	DTE2B1D	SO1A2_HUMAN	Substrate	[7]
Breast cancer resistance protein (ABCG2)	DTI7UX6	ABCG2_HUMAN	Substrate	[8]
Organic anion transporting polypeptide 1B1 (SLCO1B1)	DT3D8F0	SO1B1_HUMAN	Substrate	[9]
Organic anion transporting polypeptide 1B3 (SLCO1B3)	DT9C1TS	SO1B3_HUMAN	Substrate	[10]

Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
ATP-dependent translocase ABCB1 (ABCB1)	OTEJROBO	MDR1_HUMAN	Regulation of Drug Effects	[5]
Bcl-2-binding component 3, isoforms 3/4 (BBC3)	OTUAXDAY	BBC3B_HUMAN	Gene/Protein Processing	[11]
Bile salt export pump (ABCB11)	OTRU7THO	ABCBB_HUMAN	Gene/Protein Processing	[12]
Broad substrate specificity ATP-binding cassette transporter ABCG2 (ABCG2)	OTW8V2V1	ABCG2_HUMAN	Regulation of Drug Effects	[5]
Cyclic AMP-dependent transcription factor ATF-4 (ATF4)	OTRFV19J	ATF4_HUMAN	Gene/Protein Processing	[11]
Phorbol-12-myristate-13-acetate-induced protein 1 (PMAIP1)	OTXEE550	APR_HUMAN	Gene/Protein Processing	[11]
Phospholipid-transporting ATPase ABCA1 (ABCA1)	OT94G6BQ	ABCA1_HUMAN	Gene/Protein Processing	[13]
Poly polymerase 1 (PARP1)	OT310QSG	PARP1_HUMAN	Protein Interaction/Cellular Processes	[11]
Ras-related protein Rap-1A (RAP1A)	OT5RH6TI	RAP1A_HUMAN	Gene/Protein Processing	[11]

Molecular Interaction Atlas (MIA)

MIA Detail

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References

1	Pitavastatin FDA Label
2	BDDCS predictions, self-correcting aspects of BDDCS assignments, BDDCS assignment corrections, and classification for more than 175 additional drugs
3	Hoy SM: Pitavastatin: A Review in Hypercholesterolemia. Am J Cardiovasc Drugs. 2017 Apr;17(2):157-168. doi: 10.1007/s40256-017-0213-8.
4	Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
5	Involvement of BCRP (ABCG2) in the biliary excretion of pitavastatin. Mol Pharmacol. 2005 Sep;68(3):800-7.
6	Intestinal absorption of HMG-CoA reductase inhibitor pitavastatin mediated by organic anion transporting polypeptide and P-glycoprotein/multidrug resistance 1. Drug Metab Pharmacokinet. 2011;26(2):171-9.
7	Transporter-mediated influx and efflux mechanisms of pitavastatin, a new inhibitor of HMG-CoA reductase. J Pharm Pharmacol. 2005 Oct;57(10):1305-11.
8	ABCG2: a perspective. Adv Drug Deliv Rev. 2009 Jan 31;61(1):3-13.
9	Prediction of the in vivo OATP1B1-mediated drug-drug interaction potential of an investigational drug against a range of statins. Eur J Pharm Sci. 2012 Aug 30;47(1):244-55.
10	Impact of OATP transporters on pharmacokinetics. Br J Pharmacol. 2009 Oct;158(3):693-705.
11	Statin-induced Mitochondrial Priming Sensitizes Multiple Myeloma Cells to BCL2 and MCL-1 Inhibitors. Cancer Res Commun. 2023 Dec 8;3(12):2497-2509. doi: 10.1158/2767-9764.CRC-23-0350.
12	Early identification of clinically relevant drug interactions with the human bile salt export pump (BSEP/ABCB11). Toxicol Sci. 2013 Dec;136(2):328-43.
13	Regulation mechanism of ABCA1 expression by statins in hepatocytes. Eur J Pharmacol. 2011 Jul 15;662(1-3):9-14. doi: 10.1016/j.ejphar.2011.04.043. Epub 2011 May 1.