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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=CC=CC=C4N=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 No
Defined Stereocenters 2 / 2
E/Z Centers 1
Optical Activity UNSPECIFIED

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.

Originator

Sources: DOI: 10.2133/dmpk.14.415

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
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 Vivo Use Guide
Unknown
Route of Administration: Unknown
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 Thu Jul 06 14:06:16 UTC 2023
Edited
by admin
on Thu Jul 06 14:06:16 UTC 2023
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
FDA UNII
ULK88EV7VQ
Created by admin on Thu Jul 06 14:06:16 UTC 2023 , Edited by admin on Thu Jul 06 14:06:16 UTC 2023
PRIMARY
CAS
141750-63-2
Created by admin on Thu Jul 06 14:06:16 UTC 2023 , Edited by admin on Thu Jul 06 14:06:16 UTC 2023
PRIMARY
MERCK INDEX
M8891
Created by admin on Thu Jul 06 14:06:16 UTC 2023 , Edited by admin on Thu Jul 06 14:06:16 UTC 2023
PRIMARY Merck Index
PUBCHEM
9801294
Created by admin on Thu Jul 06 14:06:16 UTC 2023 , Edited by admin on Thu Jul 06 14:06:16 UTC 2023
PRIMARY
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