CHEBI:32020 - pitavastatin

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ChEBI Name pitavastatin
ChEBI ID CHEBI:32020
Definition A dihydroxy monocarboxylic acid that is (6E)-7-[2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl]hept-6-enoic acid in which the two hydroxy groups are located at positions 3 and 5 (the 3R,5S-stereoisomer). Used as its calcium salt for treatment of hypercholesterolemia (elevated levels of cholesterol in the blood) on patients unable to sufficiently lower their cholesterol levels by diet and exercise.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information ChemicalBook:CB6206668, eMolecules:32452448, ZINC000001534965
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Pitavastatin (usually as a calcium salt) is a member of the blood cholesterol lowering medication class of statins. Pitavastatin is an inhibitor of HMG-CoA reductase, the enzyme that catalyses the first step of cholesterol synthesis. It was patented in 1987 and approved for medical use in 2003. It is available in Japan, South Korea and in India. In the US, it received FDA approval in 2009. Kowa Pharmaceuticals, a subsidiary of Kowa Company, is the owner of the American patent to pitavastatin.
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Formula C25H24FNO4
Net Charge 0
Average Mass 421.46080
Monoisotopic Mass 421.16894
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
SMILES O[C@H](C[C@H](O)\C=C\c1c(nc2ccccc2c1-c1ccc(F)cc1)C1CC1)CC(O)=O
Roles Classification
Chemical Role(s): antioxidant
A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): EC 1.1.1.34/EC 1.1.1.88 (hydroxymethylglutaryl-CoA reductase) inhibitor
Any EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD+ or NADP+ acceptor) inhibitor that inhibits HMG-CoA reductases. Hydroxymethylglutaryl-CoA reductase inhibitors have been shown to lower directly cholesterol synthesis. The Enzyme Commission designation is EC 1.1.1.34 for the NADPH-dependent enzyme and EC 1.1.1.88 for an NADH-dependent enzyme.
(via statin )
Application(s): anticholesteremic drug
A substance used to lower plasma cholesterol levels.
(via statin )
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ChEBI Ontology
Outgoing pitavastatin (CHEBI:32020) has role antioxidant (CHEBI:22586)
pitavastatin (CHEBI:32020) is a cyclopropanes (CHEBI:51454)
pitavastatin (CHEBI:32020) is a dihydroxy monocarboxylic acid (CHEBI:35972)
pitavastatin (CHEBI:32020) is a monofluorobenzenes (CHEBI:83575)
pitavastatin (CHEBI:32020) is a quinolines (CHEBI:26513)
pitavastatin (CHEBI:32020) is a statin (synthetic) (CHEBI:87635)
pitavastatin (CHEBI:32020) is conjugate acid of pitavastatin(1−) (CHEBI:71260)
Incoming pitavastatin(1−) (CHEBI:71260) is conjugate base of pitavastatin (CHEBI:32020)
IUPAC Name
(3R,5S,6E)-7-[2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl]-3,5-dihydroxyhept-6-enoic acid
INNs Sources
pitavastatia WHO MedNet
pitavastatin WHO MedNet
pitavastatine WHO MedNet
pitavastatinum WHO MedNet
Synonyms Sources
NK 104 ChemIDplus
NK-104 ChemIDplus
Manual Xrefs Databases
2214 DrugCentral
C13334 KEGG COMPOUND
EP2141155 Patent
HMDB0041991 HMDB
Pitavastatin Wikipedia
US2011269962 Patent
US2012016129 Patent
View more database links
Registry Numbers Types Sources
147511-69-1 CAS Registry Number ChemIDplus
7257773 Reaxys Registry Number Reaxys
Citations Waiting for Citations
Last Modified
22 February 2017