Drug Information

General Information
Drug ID
DR00435
Drug Name
Simvastatin
Synonyms
(1S,3R,7S,8S,8aR)-8-{2-[(2R,4R)-4-hydroxy-6-oxotetrahydro-2H-pyran-2-yl]ethyl}-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl 2,2-dimethylbutanoate; 2,2-Dimethylbutanoic acid (1S,3R,7S,8S,8aR)-1,2,3,7,8,8a-hexahydro-3,7-dimethyl-8-[2-[(2R,4R)-tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl]ethyl]-1-naphthalenyl ester; 2,2-Dimethylbutyric acid, 8-ester with (4R,6R)-6-(2-((1S,2S,6R,8S,8aR)-1,2,6,7,8,8a-hexahydro-8-hydroxy-2,6-dimethyl-1-naphthyl)ethyl)tetrahydro-4-hydroxy-2H-pyran-2-one; Butanoic acid, 2,2-dimethyl-, (1S,3R,7S,8S,*aR)-1,2,3,7,8,8a-hexahydro-3,7-dimethyl-8-(2-((2R,4R)-tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl)-1-naphthalenyl ester; Butanoic acid, 2,2-dimethyl-, (1S,3R,7S,8S,8aR)-1,2,3,7,8,8a-hexahydro-3,7-dimethyl-8-(2-((2R,4R)-tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl)-1-naphthalenyl ester; Butanoic acid, 2,2-dimethyl-, (1S,3R,7S,8S,8aR)-1,2,3,7,8,8a-hexahydro-3,7-dimethyl-8-[2-[(2R,4R)-tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl]ethyl]-1-naphthalenyl ester; Butanoic acid, 2,2-dimethyl-,1,2,3,7,8,8a-hexahydro-3,7-dimethyl-8-[2-(tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl)-ethyl]-1-naphthalenyl ester, [1S-[1 alpha,3 alpha,7 beta,8 beta(2S*,4S*),-8a beta; Cholestat; Coledis; Colemin; Corolin; DRG-0320; Denan; KS-1113; L 644128-000U; Labistatin; Lipex; Lipovas; Lodales; MK 0733; MK 733; MK-0733; MK-733; MK733; Medipo; Nivelipol; Pantok; Rendapid; Simcard (TN); Simlup (TN); Simovil; Simvacor (TN); Simvast CR; Simvastatin & Primycin; Simvastatin (JAN/USP/INN); Simvastatin [USAN:INN:BAN]; Simvastatin, Compactin; Simvastatina; Simvastatina [Spanish]; Simvastatine; Simvastatine [French]; Simvastatinum; Simvastatinum [Latin]; Sinvacor; Sivastin; Synvinolin; TNP00259; Vasotenal; Zocor; Zocor (TN); Zocor, Simlup, Simcard, Simvacor, Simvoget, Zorced, Simvastatin; Zocord; [(1S,3R,7S,8S,8aR)-8-[2-[(2R,4R)-4-hydroxy-6-oxooxan-2-yl]ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] 2,2-dimethylbutanoate
Drug Type
Small molecular drug
Indication Hypercholesterolemia [ICD11:5C80.0] Approved [1]
Therapeutic Class
Anticholesteremic Agents
Structure
3D MOL 2D MOL
Formula
C25H38O5
Canonical SMILES
CCC(C)(C)C(=O)OC1CC(C=C2C1C(C(C=C2)C)CCC3CC(CC(=O)O3)O)C
InChI
InChI=1S/C25H38O5/c1-6-25(4,5)24(28)30-21-12-15(2)11-17-8-7-16(3)20(23(17)21)10-9-19-13-18(26)14-22(27)29-19/h7-8,11,15-16,18-21,23,26H,6,9-10,12-14H2,1-5H3/t15-,16-,18+,19+,20-,21-,23-/m0/s1
InChIKey
RYMZZMVNJRMUDD-HGQWONQESA-N
CAS Number
CAS 79902-63-9
Pharmaceutical Properties Molecular Weight 418.6 Topological Polar Surface Area 72.8
Heavy Atom Count 30 Rotatable Bond Count 7
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 5
XLogP
4.7
PubChem CID
54454
PubChem SID
10321271 ,10852028 ,11113242 ,11342166 ,11362349 ,11364611 ,11367173 ,11369735 ,11371657 ,11374383 ,11377897 ,11466893 ,11468013 ,11485617 ,11486566 ,11487751 ,11489487 ,11490485 ,11492447 ,11495531 ,11528633 ,11533326 ,12013879 ,12146013 ,14831549 ,14929313 ,24724617 ,25819951 ,26612685 ,26680673 ,26759532 ,34718442 ,46508654 ,47365442 ,47440515 ,47736737 ,47885633 ,47885634 ,48110715 ,48334759 ,48416540 ,496592 ,49698671 ,50086525 ,50100555 ,50100556 ,648581 ,7847500 ,7980599 ,8183649
ChEBI ID
ChEBI:9150
TTD Drug ID
D0H0ND
DT(s) Transporting This Drug ABCG1 Transporter Info ATP-binding cassette sub-family G member 1 Substrate [2]
BCRP Transporter Info Breast cancer resistance protein Substrate [3]
OATP1B1 Transporter Info Organic anion transporting polypeptide 1B1 Substrate [4]
P-GP Transporter Info P-glycoprotein 1 Substrate [5]
References
1 Simvastatin was approved by FDA. The official website of the U.S. Food and Drug Administration. (2019)
2 HMG-CoA reductase inhibitors, simvastatin and atorvastatin, downregulate ABCG1-mediated cholesterol efflux in human macrophages. J Cardiovasc Pharmacol. 2013 Jul;62(1):90-8.
3 Human intestinal transporter database: QSAR modeling and virtual profiling of drug uptake, efflux and interactions. Pharm Res. 2013 Apr;30(4):996-1007.
4 Impact of OATP transporters on pharmacokinetics. Br J Pharmacol. 2009 Oct;158(3):693-705.
5 Mammalian drug efflux transporters of the ATP binding cassette (ABC) family in multidrug resistance: A review of the past decade. Cancer Lett. 2016 Jan 1;370(1):153-64.

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