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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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
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.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
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
Record UNII
ULK88EV7VQ
Record Status Validated (UNII)
Record Version