Chemical Properties of Simvastatin

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

InChI Key

RYMZZMVNJRMUDD-UHFFFAOYSA-N

Formula

C25H38O5

SMILES

CCC(C)(C)C(=O)OC1CC(C)C=C2C=CC(C)C(CCC3CC(O)CC(=O)O3)C21

Molecular Weight¹

418.57

Other Names

• (+)-Simvastatin
• 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 (simvastatin)
• 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, 1,2,3,7,8,8a-hexahydro-3,7-dimethyl-8-[2-(tetrahydro-4-hydroxy-6-oxo-2H-pyran-2yl)-ethyl)]-1-naphtalenyl 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-, 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»]]-
• Synvinolin
• Zocor

• C_p,gas : Ideal gas heat capacity (J/mol×K).
• η : Dynamic viscosity (Pa×s).
• Δ_fusH° : Enthalpy of fusion at standard conditions (kJ/mol).
• Δ_fusH : Enthalpy of fusion at a given temperature (kJ/mol).
• log₁₀WS : Log10 of Water solubility in mol/l.
• logP_oct/wat : Octanol/Water partition coefficient.
• McVol : McGowan's characteristic volume (ml/mol).
• I_np : Non-polar retention indices.
• T_fus : Normal melting (fusion) point (K).
• ¹: Molecular weight from the IUPAC atomic weights tables.

Physical Properties

Property	Value	Unit	Source
ΔfusH°	[30.13; 32.17]	kJ/mol
ΔfusH°	32.17	kJ/mol	Solubility and limiting activity coefficient of simvastatin in different organic solvents
ΔfusH°	30.13	kJ/mol	Solution thermodynamics of simvastatin in pure solvents and binary solvent mixtures
log10WS	-5.00		Relay (1.0) Calculated Property
logPoct/wat	4.586		Crippen Calculated Property
McVol	342.680	ml/mol	McGowan Calculated Property
Inp	[3221.90; 3221.90]
Inp	3221.90		NIST
Inp	3221.90		NIST
Tfus	423.81	K	Relay (1.0) Calculated Property

Cheméo can also estimate Normal Boiling Point Temperature, Critical Temperature, Critical Pressure, Critical Volume, Enthalpy of formation at standard conditions, Enthalpy of vaporization at standard conditions, Standard Gibbs free energy of formation, Acentric Factor, Ionization energy for this compound, but they fall outside the models' validated range, so they are not shown here. Open the prediction tool to compute them on demand.

Temperature Dependent Properties

Property	Value	Unit	Temperature (K)	Source
ΔfusH	[29.59; 32.17]	kJ/mol	[412.60; 413.80]
ΔfusH	32.17	kJ/mol	412.60	NIST
ΔfusH	29.59	kJ/mol	413.80	NIST

Correlations

Property	Value	Unit	Temperature (K)	Source
Cp,gas	[483.42; 1254.56]	J/mol×K	[273.00; 1000.00]	Joback Predicted correlation
Equation			Y = A + B·T + C·T² + D·T³ + E·T⁴ Y is Cp,gas in J/mol×K, T in K
Coefficient A			-1.10917e+02
Coefficient B			2.55630e+00
Coefficient C			-1.46372e-03
Coefficient D			2.72900e-07
Coefficient E			0.00000e+00
Temperature range, min.			273.00
Temperature range, max.			1000.00
Cp,gas	483.42	J/mol×K	273.00	Calculated Property
Cp,gas	622.33	J/mol×K	353.78	Calculated Property
Cp,gas	745.93	J/mol×K	434.56	Calculated Property
Cp,gas	855.06	J/mol×K	515.33	Calculated Property
Cp,gas	950.60	J/mol×K	596.11	Calculated Property
Cp,gas	1033.41	J/mol×K	676.89	Calculated Property
Cp,gas	1104.34	J/mol×K	757.67	Calculated Property
Cp,gas	1164.27	J/mol×K	838.44	Calculated Property
Cp,gas	1214.06	J/mol×K	919.22	Calculated Property
Cp,gas	1254.56	J/mol×K	1000.00	Calculated Property

Property	Value	Unit	Temperature (K)	Source
η	[0.0007508; 0.0000690]	Pa×s	[552.71; 860.33]	Joback Predicted correlation
Equation			Y = exp(A + B/T + C·ln(T) + D·T^E) Y is η in Pa×s, T in K
Coefficient A			-1.38701e+01
Coefficient B			3.68980e+03
Coefficient C			0.00000e+00
Coefficient D			0.00000e+00
Coefficient E			0.00000e+00
Temperature range, min.			552.71
Temperature range, max.			860.33
η	0.0007508	Pa×s	552.71	Calculated Property
η	0.0005090	Pa×s	586.89	Calculated Property
η	0.0003601	Pa×s	621.07	Calculated Property
η	0.0002641	Pa×s	655.25	Calculated Property
η	0.0001998	Pa×s	689.43	Calculated Property
η	0.0001552	Pa×s	723.61	Calculated Property
η	0.0001233	Pa×s	757.79	Calculated Property
η	0.0000999	Pa×s	791.97	Calculated Property
η	0.0000824	Pa×s	826.15	Calculated Property
η	0.0000690	Pa×s	860.33	Calculated Property

Similar Compounds

Find more compounds similar to Simvastatin.

Mixtures

• Acetic acid, methyl ester + Simvastatin
• Ethyl Acetate + Simvastatin
• Acetic acid, propyl ester + Simvastatin
• Acetic acid, butyl ester + Simvastatin
• Acetic acid, 2-methylpropyl ester + Simvastatin
• Acetic acid, 2-methylpropyl ester + Heptane + Simvastatin
• Isopropyl acetate + Simvastatin
• sec-Butyl acetate + Simvastatin
• Acetic acid, 1,1-dimethylethyl ester + Simvastatin
• Ethanol + Simvastatin
• 1-Propanol + Simvastatin
• 1-Butanol + Simvastatin
• 1-Pentanol + Simvastatin
• 1-Hexanol + Simvastatin
• 1-Octanol + Simvastatin
• Carbon dioxide + Methylene chloride + Simvastatin

Sources

• Cheméo Relay (1.0)
• Cheméo Relay (1.0, beta) Beta: served but experimental, data-limited and below our cross-validation release bar; the Joback value is recommended where available.
• Crippen Method
• Crippen Method
• Solubility and limiting activity coefficient of simvastatin in different organic solvents
• Solution thermodynamics of simvastatin in pure solvents and binary solvent mixtures
• Solubility of Simvastatin and Lovastatin in Mixtures of Dichloromethane and Supercritical Carbon Dioxide
• Joback Method
• McGowan Method
• NIST Webbook

Note: Cheméo is only indexing the data, follow the source links to retrieve the latest data. The source is also providing more information like the publication year, authors and more. Take the time to validate and double check the source of the data.
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