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Details

Stereochemistry ABSOLUTE
Molecular Formula C25H22FNO3
Molecular Weight 403.4455
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of PITAVASTATIN LACTONE

SMILES

O[C@@H]1C[C@H](OC(=O)C1)\C=C\C2=C(C3=CC=C(F)C=C3)C4=C(C=CC=C4)N=C2C5CC5

InChI

InChIKey=XJVKVAFYQRWVAJ-MCBHFWOFSA-N
InChI=1S/C25H22FNO3/c26-17-9-7-15(8-10-17)24-20-3-1-2-4-22(20)27-25(16-5-6-16)21(24)12-11-19-13-18(28)14-23(29)30-19/h1-4,7-12,16,18-19,28H,5-6,13-14H2/b12-11+/t18-,19-/m1/s1

HIDE SMILES / InChI

Molecular Formula C25H22FNO3
Molecular Weight 403.4455
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry
Defined Stereocenters 2 / 2
E/Z Centers 1
Optical Activity UNSPECIFIED

Description

Pitavastatin lactone is the major metabolite of pitavastatin in humans. Pitavastatin is a potent competitive inhibitor of HMG-CoA reductase, which is indicated for hypercholesterolaemia (elevated cholesterol) and for the prevention of cardiovascular disease. Uridine 5’ -diphosphate (UDP) glucuronosyl transferase (UGT) is critically involved in the lactonization of pitavastatin in man and animals. The metabolic and transporter profiles of pitavastatin in man are complex, involving acid/lactone interconversion. Both forms of pitavastatin are observed in-vivo following oral administration. Lactone form and pitavastatin differ in substrate activity towards uptake and efflux transporters.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
PubMed

PubMed

TitleDatePubMed
Interaction between several medicines and statins.
2003
Metabolic fate of pitavastatin, a new inhibitor of HMG-CoA reductase: similarities and difference in the metabolism of pitavastatin in monkeys and humans.
2003 Jul
Metabolic properties of the acid and lactone forms of HMG-CoA reductase inhibitors.
2004 Nov-Dec
Pharmacokinetics of pitavastatin in subjects with Child-Pugh A and B cirrhosis.
2005 Mar
Effect of OATP1B1 (SLCO1B1) variant alleles on the pharmacokinetics of pitavastatin in healthy volunteers.
2005 Oct
Transporter-mediated influx and efflux mechanisms of pitavastatin, a new inhibitor of HMG-CoA reductase.
2005 Oct
Patents

Patents

Sample Use Guides

In Vitro Use Guide
The apparent Km for pitavastatin lactone in hepatic and renal microsomes were 49.4 and 48.8 mm, respectively, and the Vmax were 124.6 and 115.6 pmol min(-1) mg(-1) protein, respectively. The intrinsic clearances (Vmax/Km) were 2.5 and 2.4 ml min(-1) mg(-1) protein, respectively.
Substance Class Chemical
Created
by admin
on Mon Oct 21 20:01:41 UTC 2019
Edited
by admin
on Mon Oct 21 20:01:41 UTC 2019
Record UNII
ULK88EV7VQ
Record Status Validated (UNII)
Record Version
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Name Type Language
PITAVASTATIN LACTONE
MI  
Common Name English
NISVASTATIN
Common Name English
P-87244
Code English
NK-104 (LACTONE)
Code English
PITAVASTATIN LACTONE [MI]
Common Name English
2H-PYRAN-2-ONE, 6-((1E)-2-(2-CYCLOPROPYL-4-(4-FLUOROPHENYL)-3-QUINOLINYL)ETHENYL)TETRAHYDRO-4-HYDROXY-, (4R,6S)-
Systematic Name English
(4R,6S)-6-((1E)-2-(2-CYCLOPROPYL-4-(4-FLUOROPHENYL)-3-QUINOLINYL)ETHENYL)TETRAHYDRO-4-HYDROXY-2H-PYRAN-2-ONE
Systematic Name English
Code System Code Type Description
CAS
141750-63-2
Created by admin on Mon Oct 21 20:01:41 UTC 2019 , Edited by admin on Mon Oct 21 20:01:41 UTC 2019
PRIMARY
MERCK INDEX
M8891
Created by admin on Mon Oct 21 20:01:41 UTC 2019 , Edited by admin on Mon Oct 21 20:01:41 UTC 2019
PRIMARY Merck Index
PUBCHEM
9801294
Created by admin on Mon Oct 21 20:01:41 UTC 2019 , Edited by admin on Mon Oct 21 20:01:41 UTC 2019
PRIMARY
Related Record Type Details
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