Pravastatin (CED0002183)

Record Information
Version1.0
Creation Date2016-05-25 03:25:14 UTC
Update Date2026-05-14 16:24:28 UTC
Accession NumberCHEM021331
Identification
Common NamePravastatin
ClassSmall Molecule
Description
Pravastatin is an organic compound with the formula C23H36O7 and an average molecular weight of 424.53 g/mol. Pravastatin belongs to the medium-chain hydroxy acids and derivatives, a subclass of hydroxy acids and derivatives within the organic compounds. It is recorded as a biological antioxidant (PMC8252743). The compound is identified as a lipid modifying agent within healthcare, pharmaceuticals, and veterinary products. It has two recorded protein targets, acting as an inhibitor of 3-hydroxy-3-methylglutaryl-coenzyme A reductase (HMGCR) and Histone deacetylase 2 (HDAC2). The oral route is the recorded exposure route for this substance. Pravastatin is found in or released from 13 recorded sources. These include drinking water and water supply (Drinking water), as well as food, food processing and cookware sources such as the preparation of malt, the preparation of wort, the preparation of wine or sparkling wine, and fermentation processes for beer. Within household cleaning and consumer products, it is associated with cigar cigarettes, non electric simulated smoking devices, and other smoking requisites. Additionally, it is found in electrical and electronic equipment, specifically antennas, amplifiers, television systems, and electrically stimulated smoking devices.
Contaminant TypeNot Available
Chemical Structure
Synonyms
ValueSource
(+)-(3R,5R)-3,5-Dihydroxy-7-[(1S,2S,6S,8S,8ar)-6-hydroxy-2-methyl-8-{[(S)-2-methylbutyryl]oxy}-1,2,6,7,8,8a-hexahydro-1-naphthyl]heptanoic acidChEBI
Pravastatin acidChEBI
PravastatinaChEBI
PravastatineChEBI
PravastatinumChEBI
PravatorKegg
(+)-(3R,5R)-3,5-Dihydroxy-7-[(1S,2S,6S,8S,8ar)-6-hydroxy-2-methyl-8-{[(S)-2-methylbutyryl]oxy}-1,2,6,7,8,8a-hexahydro-1-naphthyl]heptanoateGenerator
(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-dihydroxyheptanoic acidHMDB
3beta-HydroxycompactinHMDB
EptastatinHMDB
MevalothinHMDB
PravacholHMDB
Pravastatin sodiumHMDB
SelektineHMDB
ElisorHMDB
Nu-pravastatinHMDB
PravasinHMDB
Apo pravastatinHMDB
Aventis brand OF pravastatin sodiumHMDB
Bristol-myers squibb brand OF pravastatin sodiumHMDB
Juste brand OF pravastatin sodiumHMDB
Lin pravastatinHMDB
MevalotinHMDB
Pravastatin monosodium salt, (6 beta)-isomerHMDB
Pravastatin sodium saltHMDB
Pravastatin, (6 beta)-isomerHMDB
RMS-431HMDB
Squibb brand OF pravastatin sodiumHMDB
VastenHMDB
Apo-pravastatinHMDB
Apotex brand OF pravastatin sodiumHMDB
Linson pharma brand OF pravastatin sodiumHMDB
LiplatHMDB
LipostatHMDB
Nu-pharma brand OF pravastatin sodiumHMDB
PrareductHMDB
Pravastatin tert-octylamine saltHMDB
RMS 431HMDB
Sankyo brand OF pravastatin sodiumHMDB
Sodium salt, pravastatinHMDB
BristacolHMDB
Esteve brand OF pravastatin sodiumHMDB
Lin-pravastatinHMDB
LipemolHMDB
Nu pravastatinHMDB
PravacolHMDB
Pravastatin tert octylamine saltHMDB
Chemical FormulaC23H36O7
Average Molecular Mass424.528 g/mol
Monoisotopic Mass424.246 g/mol
CAS Registry Number81093-37-0
IUPAC Name(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-dihydroxyheptanoic acid
Traditional Namepravastatin
SMILES[H][C@]12[C@H](C[C@H](O)C=C1C=C[C@H](C)[C@@H]2CC[C@@H](O)C[C@@H](O)CC(O)=O)OC(=O)[C@@H](C)CC
InChI IdentifierInChI=1S/C23H36O7/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)/t13-,14-,16+,17+,18+,19-,20-,22-/m0/s1
InChI KeyTUZYXOIXSAXUGO-PZAWKZKUSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as medium-chain hydroxy acids and derivatives. These are hydroxy acids with a 6 to 12 carbon atoms long side chain.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassHydroxy acids and derivatives
Sub ClassMedium-chain hydroxy acids and derivatives
Direct ParentMedium-chain hydroxy acids and derivatives
Alternative Parents
Substituents
  • Medium-chain hydroxy acid
  • Fatty alcohol
  • Medium-chain fatty acid
  • Hydroxy fatty acid
  • Fatty acid ester
  • Branched fatty acid
  • Beta-hydroxy acid
  • Fatty acyl
  • Dicarboxylic acid or derivatives
  • Secondary alcohol
  • Carboxylic acid ester
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.24 g/LALOGPS
logP2.23ALOGPS
logP1.65ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)4.21ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area124.29 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity113.6 m³·mol⁻¹ChemAxon
Polarizability46.56 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0a4i-6194400000-5f7280491acf9312a516Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-004i-8202269000-c5995d4b5b537e3a6f6eNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0uk9-0009000000-967b377abafe64b73071Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0002900000-bd7fd66d793ae64426ffNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-4809000000-0ed5a8797dfc49ecf5afNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-2900000000-91b125182ce5d90f16abNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-1900000000-e8fc6384260de93c5aa8Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-1900000000-11e99968bc0ba393b6f9Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-4900000000-0e4265e6dc1468c1471dNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0002900000-8795ee00dded0ef8be48Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-3709000000-aa45be15af0471c0a46eNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-2900000000-5617409991f5c58e5130Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-2900000000-2bf5c13979a639625d1cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-2900000000-9a233e521607e82ab7a0Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0900000000-2083dfbb67bf2b03ccf9Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0uk9-0009000000-4b2c09a295ba7f3ce41bNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0607900000-e57e263ad3f74bfda195Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0uk9-0209000000-e1f3357e6db2a045c733Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-053r-0890100000-343e9a2af9d9e56f3078Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0fk9-3209000000-4e7af37985a2d2fdf90cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0pb9-9600000000-1e8b86b20daa312fd4c0Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-9300000000-9b9ada2f0c8f95041540Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0pb9-9500000000-cd813fd7988b2d9e71c7Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0zfr-9800000000-b7d7b3bf79adbd5de030Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0zfr-9800000000-c49a5e173a1c011d96a1Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-052r-1009600000-9928021021dc6868847dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-052r-4019100000-bea6aa9fed446c2cdd3cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-052r-9023000000-7b0213c49b76e864814eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-05fr-1007900000-cb1ad55355bd717f1c23Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-5209300000-f017d063b98b59e6d5f1Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-9244000000-d95d5ae750ad620ba728Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-05g1-9207200000-7f00874a63e9a5aa5a9cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0zmi-9464000000-25cb35a7f3918d54820fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-9114000000-4418bf363d98cc7b7a30Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00fu-1229200000-25e1c010e84505db1b76Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-05tr-9486100000-a10c8b187cf745260692Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-006y-6923000000-c2601e19e82e4c99e636Not AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
3829.0Log mg/kg[2200:6800]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
115Drinking waterDrinking water & water supplyNot Available
233BrushesPersonal care & cosmeticsNot Available
298Lipid modifying agentsHealthcare, pharmaceuticals & veterinary productsNot Available
505AmplifiersElectrical & Electronic EquipmentNot Available
506AntennasElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
537Television SystemsElectrical & Electronic EquipmentNot Available
544Fermentation Processes For BeerFood, food processing & cookwareNot Available
547Preparation Of MaltFood, food processing & cookwareNot Available
549Preparation Of Wine Or Sparkling WineFood, food processing & cookwareNot Available
550Preparation Of WortFood, food processing & cookwareNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
581Paper Making MachinesIndustrial manufacturing & chemical processingNot Available
602MolluscicidesAgriculture & land managementNot Available
Pathways
3 pathways
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
3-hydroxy-3-methylglutaryl-coenzyme A reductase structureClick to view 3D structure3-hydroxy-3-methylglutaryl-coenzyme A reductaseP04035HumansPredicted (SEA)0.467095
Solute carrier organic anion transporter family member 1B1 structureClick to view 3D structureSolute carrier organic anion transporter family member 1B1Q9Y6L6HumansPredicted (SEA)2.72472
Click to view 3D structure3-hydroxy-3-methylglutaryl-coenzyme A reductaseP51639Rattus norvegicusPredicted (SEA)0.311397
Click to view 3D structureVoltage-dependent L-type calcium channel subunit alpha-1CQ01815Mus musculusPredicted (SEA)0.0778492
Click to view 3D structure3-hydroxy-3-methylglutaryl-coenzyme A reductaseQ01237Mus musculusPredicted (SEA)0.700643
ATP-dependent translocase ABCB1 structureClick to view 3D structureATP-dependent translocase ABCB1P08183HumansPredicted (SEA)243.435
Click to view 3D structureCholinesteraseP81908Equus caballusPredicted (SEA)315.367
Click to view 3D structureAcetylcholinesteraseO42275Electrophorus electricusPredicted (SEA)315.056
Sodium-dependent noradrenaline transporter structureClick to view 3D structureSodium-dependent noradrenaline transporterP23975HumansPredicted (SEA)1344.92
Squalene monooxygenase structureClick to view 3D structureSqualene monooxygenaseQ14534HumansPredicted (SEA)0.467095
Sodium-dependent dopamine transporter structureClick to view 3D structureSodium-dependent dopamine transporterQ01959HumansPredicted (SEA)1931.83
Rho-related GTP-binding protein RhoC structureClick to view 3D structureRho-related GTP-binding protein RhoCP08134HumansPredicted (SEA)27.0137
Substance-K receptor structureClick to view 3D structureSubstance-K receptorP21452HumansPredicted (SEA)987.05
Nuclear receptor subfamily 4 group A member 2 structureClick to view 3D structureNuclear receptor subfamily 4 group A member 2P43354HumansPredicted (SEA)93.0298
Click to view 3D structureProstaglandin E2 receptor EP1 subtypeP34995HumansPredicted (SEA)689.199
Solute carrier organic anion transporter family member 2A1 structureClick to view 3D structureSolute carrier organic anion transporter family member 2A1Q92959HumansPredicted (SEA)7.55137
Prostacyclin receptor structureClick to view 3D structureProstacyclin receptorP43119HumansPredicted (SEA)1107.95
Prostaglandin E2 receptor EP3 subtype structureClick to view 3D structureProstaglandin E2 receptor EP3 subtypeP43115HumansPredicted (SEA)1740.63
Prostaglandin E2 receptor EP2 subtype structureClick to view 3D structureProstaglandin E2 receptor EP2 subtypeP43116HumansPredicted (SEA)1642.39
Cytochrome P450 2C8 structureClick to view 3D structureCytochrome P450 2C8P10632HumansPredicted (SEA)4513.08
Click to view 3D structureProstaglandin D2 receptorQ13258HumansPredicted (SEA)1780.49
Prostaglandin F2-alpha receptor structureClick to view 3D structureProstaglandin F2-alpha receptorP43088HumansPredicted (SEA)1131.62
Thromboxane A2 receptor structureClick to view 3D structureThromboxane A2 receptorP21731HumansPredicted (SEA)2051.95
Bile salt export pump structureClick to view 3D structureBile salt export pumpO95342HumansPredicted (SEA)2206.32
Photoreceptor-specific nuclear receptor structureClick to view 3D structurePhotoreceptor-specific nuclear receptorQ9Y5X4HumansPredicted (SEA)2664.7
Concentrations
StatusValueUnitSample LocationReference
Detected and Semi Quantified20ng/LBioggio,Lugano
Detected and Semi Quantified35ng/LHallau,Klettgau
Detected and Semi Quantified30ng/LUetendorf,Thun
Detected and Semi Quantified34ng/LVernier,Aïre
Detected and Semi Quantified100ng/LWerdhölzli,Zürich
External Links
DrugBank IDDB00175
HMDB IDHMDB0005022
FooDB IDFDB023593
Phenol Explorer IDNot Available
KNApSAcK IDC00000565
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID2053
PDB IDNot Available
Wikipedia LinkPravastatin
Chemspider ID49398
ChEBI ID63618
PubChem Compound ID54687
Kegg Compound IDC01844
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Peng, Yulin; Yashphe, Jacob; Demain, Arnold L. Biotransformation of compactin to pravastatin by Actinomadura sp. 2966. Journal of Antibiotics (1997), 50(12), 1032-1035.
2. Tonelli M, Sacks F, Pfeffer M, Jhangri GS, Curhan G: Biomarkers of inflammation and progression of chronic kidney disease. Kidney Int. 2005 Jul;68(1):237-45.
3. Peverill RE, Smolich JJ, Malan E, Goldstat R, Davis SR: Comparison of effects of pravastatin and hormone therapy on soluble P-selectin and platelet P-selectin expression in postmenopausal hypercholesterolemic women. Maturitas. 2006 Jan 20;53(2):158-65.
4. Gaugler MH, Vereycken-Holler V, Squiban C, Vandamme M, Vozenin-Brotons MC, Benderitter M: Pravastatin limits endothelial activation after irradiation and decreases the resulting inflammatory and thrombotic responses. Radiat Res. 2005 May;163(5):479-87.
5. Bruni F, Puccetti L, Pasqui AL, Pastorelli M, Bova G, Cercignani M, Palazzuoli A, Leo A, Auteri A: Different effect induced by treatment with several statins on monocyte tissue factor expression in hypercholesterolemic subjects. Clin Exp Med. 2003 May;3(1):45-53.
6. Pokrovskaia EV, Vaulin NA, Gratsianskii NA, Averkov OV, Deev AD: [Markers of inflammation and platelet aggregation in patients with non ST elevation acute coronary syndrome treated with atorvastatin or pravastatin]. Kardiologiia. 2003;43(1):7-18.
7. Tonelli M, Isles C, Craven T, Tonkin A, Pfeffer MA, Shepherd J, Sacks FM, Furberg C, Cobbe SM, Simes J, West M, Packard C, Curhan GC: Effect of pravastatin on rate of kidney function loss in people with or at risk for coronary disease. Circulation. 2005 Jul 12;112(2):171-8. Epub 2005 Jul 5.
8. FDA label
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=21749370
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=21851379
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=25264019