Pravastatin sodiumProduct ingredient for Pravastatin

Name
Pravastatin sodium
Drug Entry
Pravastatin

Pravastatin is the 6-alpha-hydroxy acid form of mevastatin.11 Pravastatin was firstly approved in 1991 becoming the second available statin in the United States. It was the first statin administered as the active form and not as a prodrug.10 This drug was developed by Sankyo Co. Ltd.; however, the first approved pravastatin product was developed by Bristol Myers Squibb and FDA approved in 1991.14

Pravastatin is made through a fermentation process in which mevastatin is first obtained. The manufacturing process is followed by the hydrolysis of the lactone group and the biological hydroxylation with Streptomyces carbophilus to introduce the allylic 6-alcohol group.12

Accession Number
DBSALT000146
Structure
Synonyms
Not Available
UNII
3M8608UQ61
CAS Number
81131-70-6
Weight
Average: 446.5096
Monoisotopic: 446.228048149
Chemical Formula
C23H35NaO7
InChI Key
VWBQYTRBTXKKOG-IYNICTALSA-M
InChI
InChI=1S/C23H36O7.Na/c1-4-13(2)23(29)30-20-11-17(25)9-15-6-5-14(3)19(22(15)20)8-7-16(24)10-18(26)12-21(27)28;/h5-6,9,13-14,16-20,22,24-26H,4,7-8,10-12H2,1-3H3,(H,27,28);/q;+1/p-1/t13-,14-,16+,17+,18+,19-,20-,22-;/m0./s1
IUPAC Name
sodium (3R,5R)-7-[(1S,2S,6S,8S,8aR)-6-hydroxy-2-methyl-8-{[(2S)-2-methylbutanoyl]oxy}-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]-3,5-dihydroxyheptanoate
SMILES
[Na+].[H][C@@](O)(CC[C@@]1([H])[C@@]([H])(C)C=CC2=C[C@@]([H])(O)C[C@]([H])(OC(=O)[C@@]([H])(C)CC)[C@]12[H])C[C@@]([H])(O)CC([O-])=O
PubChem Compound
16759173
ChemSpider
49400
ChEBI
8361
ChEMBL
CHEMBL690
Wikipedia
Pravastatin
Predicted Properties
PropertyValueSource
Water Solubility0.188 mg/mLALOGPS
logP1.87ALOGPS
logP1.65Chemaxon
logS-3.4ALOGPS
pKa (Strongest Acidic)4.21Chemaxon
pKa (Strongest Basic)-2.7Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count6Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area127.12 Å2Chemaxon
Rotatable Bond Count11Chemaxon
Refractivity124.44 m3·mol-1Chemaxon
Polarizability45.58 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon