Simvastatin

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for Simvastatin are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the Simvastatin?

The molecule Simvastatin presents a molecular formula of C8H10N4O2 and its IUPAC name is [(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.

Simvastatin is a molecule used in the treatment of cholesterol. It is a member of the statin class of drugs, which are used to lower cholesterol by inhibiting the HMG-CoA reductase enzyme. Simvastatin is used to treat primary hypercholesterolemia and mixed dyslipidemia. It is also used to prevent cardiovascular disease in people with multiple risk factors. The most common side effects of simvastatin are gastrointestinal..

3D structure

Cartesian coordinates

Geometry of Simvastatin in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

Simvastatin RYYVLZVUVIJVGH-UHFFFAOYSA-N chemical compound 2D structure molecule svg
Simvastatin

 

Molecule descriptors

 
IUPAC name[(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
InChI codeInChI=1S/C8H10N4O2/c1-10-4-9-6-5(10)7(13)12(3)8(14)11(6)2/h4H,1-3H3
InChI KeyRYYVLZVUVIJVGH-UHFFFAOYSA-N
SMILESCn1c(=O)c2c(ncn2C)n(C)c1=O

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

  • (+)-Simvastatin
  • (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-naphthalenyly-2,2-dimethyl butanoate
  • (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-dimethylbu
  • (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
  • (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
  • (1S,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
  • 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
  • 79902-63-9
  • 902S639
  • A839783
  • AB00053395-07
  • AB00053395-08
  • AB00053395-10
  • AB00053395_11
  • AB00053395_13
  • AC-1530
  • AGG2FN16EV
  • BBL024390
  • BCBcMAP01_000007
  • BDBM50139181
  • BIDD:GT0769
  • BPBio1_001001
  • BRN 4768037
  • BS164407
  • BSPBio_000909
  • BSPBio_002337
  • 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.))-
  • 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-(1alpha,3alpha,7beta,8beta(2S*,4S*),8abeta))-
  • C10AA01
  • CCG-39069
  • CCRIS 7558
  • Coledis
  • Colemin
  • Corolin
  • Cholestat
  • D00434
  • DB00641
  • DRG-0320
  • DSSTox_CID_3581
  • DSSTox_GSID_23581
  • DSSTox_RID_77090
  • Denan
  • DivK1c_006991
  • Eucor
  • GTPL2955
  • HMS1570N11
  • HMS1922H13
  • HMS2089D12
  • HMS2093E06
  • HMS2097N11
  • HMS2231N22
  • HMS3259B12
  • HMS3412P08
  • HMS3676P08
  • HMS3714N11
  • HMS3884G10
  • HSDB 7208
  • HY-17502
  • KBio1_001935
  • KBio2_002197
  • KBio2_004765
  • KBio2_007333
  • KBio3_001557
  • KBioGR_001244
  • KBioSS_002197
  • KS-1113
  • Kolestevan
  • L 644128-000U
  • Labistatin
  • Lipex
  • Lipinorm
  • Lipovas
  • Lodales
  • MK 0733
  • MK 733
  • MK-0733
  • MK-733
  • MK733
  • MLS001304029
  • MLS001333077
  • MLS001333078
  • MLS002154038
  • MLS006011866
  • MRF-0000729
  • Medipo
  • Modutrol
  • NC00719
  • NCGC00016940-01
  • NCGC00017324-01
  • NCGC00017324-02
  • NCGC00017324-03
  • NCGC00017324-04
  • NCGC00017324-05
  • NCGC00017324-07
  • NCGC00017324-08
  • NCGC00017324-09
  • NCGC00254418-01
  • NSC 758706
  • NSC-633782
  • NSC-758706
  • NSC633782
  • NSC758706
  • Nivelipol
  • Nor-Vastina
  • POLYCAP COMPONENT SIMVASTATIN
  • Pantok
  • Pharmakon1600-01504236
  • Prestwick0_000865
  • Prestwick1_000865
  • Prestwick2_000865
  • Prestwick3_000865
  • Prestwick_171
  • Q670131
  • RYMZZMVNJRMUDD-HGQWONQESA-
  • Rechol
  • Rendapid
  • S0509
  • SBI-0206773.P001
  • SIMCOR COMPONENT SIMVASTATIN
  • SIMVASTATIN COMPONENT OF SIMCOR
  • SIMVASTATIN COMPONENT OF VYTORIN
  • SMR000718785
  • SPECTRUM1504236
  • SR-05000001894
  • SR-05000001894-1
  • SR-05000001894-2
  • STK801938
  • Simcard
  • Simlup
  • Simovil
  • Simvacor
  • Simvast CR
  • Simvastatin
  • Simvastatin & Primycin
  • Simvastatin (JP17/USP/INN)
  • Simvastatin (Zocor)
  • Simvastatin lactone
  • Simvastatin,(S)
  • Simvastatin- Bio-X
  • Simvastatina
  • Simvastatine
  • Simvastatinum
  • Simvoget
  • Simvotin
  • Sinvacor
  • Sinvascor
  • Sivastin
  • SpecPlus_000895
  • Synvinolin
  • TNP00259
  • VYTORIN COMPONENT SIMVASTATIN
  • Valemia
  • Vasotenal
  • Velostatin
  • Z1741982918
  • Zocor
  • Zocord
  • Zorced
  • Zosta
  • [(1S,3R,7S,8S,8aR)-8-[2-[(2R,4R)-4-hydroxy-6-oxo-tetrahydropyran-2-yl]ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] 2,2-dimethylbutanoate
  • [(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
  • inactive simvastatin
  • s1792
  • simvastatin
  • simvastatin predrug

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC3780893
  • CAS-79902-63-9
  • UNII-AGG2FN16EV
  • AKOS005111006
  • AKOS015842733
  • BRD-K22134346-001-05-8
  • BRD-K22134346-001-11-6
  • BRD-K22134346-001-15-7
  • DTXSID0023581
  • CHEMBL1064
  • CHEBI:9150
  • Tox21_110696
  • Tox21_300400
  • Tox21_110696_1
  • SPBio_001881
  • SPBio_002830
  • SCHEMBL2471
  • Spectrum_001717
  • Spectrum2_001671
  • Spectrum3_000669
  • Spectrum4_000632
  • Spectrum5_001428

Physico-Chemical properties

IUPAC name[(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
Molecular formulaC8H10N4O2
Molecular weight194.191
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity52.04
LogP-1.0
Topological polar surface area61.8

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.