Simvastatin
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| Category | Enzyme inhibitors |
| Catalog number | BBF-04045 |
| CAS | 79902-63-9 |
| Molecular Weight | 418.57 |
| Molecular Formula | C25H38O5 |
| Purity | >98% |
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Description
Simvastatin is a competitive inhibitor of HMG-CoA reductase with Ki of 0.1-0.2 nM .
Specification
| Synonyms | Nodinitib-1; Zocor; Synvinolin; MK-733; Sinvacor; MK 733; MK733 |
| Storage | Store at -20°C |
| 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 |
| 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 |
| InChI Key | RYMZZMVNJRMUDD-HGQWONQESA-N |
| Source | Semi-synthetic |
Properties
| Appearance | White Crystalline Powder |
| Boiling Point | 564.9°C at 760 mmHg |
| Melting Point | 112-125°C |
| Density | 1.16 g/cm3 |
| Solubility | Soluble in ethanol, methanol, DMF, DMSO |
| LogP | 4.68 |
Toxicity
| Carcinogenicity | No indication of carcinogenicity to humans (not listed by IARC). |
| Mechanism Of Toxicity | Simvastatin is a prodrug in which the 6-membered lactone ring of simvastatin is hydrolyzed in vivo to generate the beta,delta-dihydroxy acid, an active metabolite structurally similar to HMG-CoA (hydroxymethylglutaryl CoA). Once hydrolyzed, simvastatin competes with HMG-CoA for HMG-CoA reductase, a hepatic microsomal enzyme. Interference with the activity of this enzyme reduces the quantity of mevalonic acid, a precursor of cholesterol. |
Reference Reading
1. Input of selected human pharmaceutical metabolites into the Norwegian aquatic environment
Katherine Langford and Kevin V. Thomas*. J. Environ. Monit., 2011, 13, 416–421
Although we did not detect any ATV metabolites in surface water, interestingly we did detect the presence of the main and active metabolite of the statin prodrug simvastatin (SV); simvastatin hydroxy carboxylic acid (SVA) in four of the surface water and sediments collected from Oslofjord.The surface water samples collected contained SVA at concentrations > LODand up to 66 ng L-1, whilst two sediment samples contained low ng g-1 (dw) concentrations of SVA also. No effluent concentrations of SVA were determined; however, we have previously reported the occurrence of SV at low ng L-1 in VEAS WwTW effluent suggesting from these preliminary data that effluent concentrations of SVA would indeed be higher. This hypothesis is supported by the published occurrence of SVA in US WwTW effluents at low ng L-1 concentrations and surface water concentrations of <0.25 ng L-5. Pharmacokinetic studies have shown that around 15%is excreted in urine as SVA and 85% in faeces as SVA; an excretion ratio of 6 : 1 of SVA : SA. This may explain why SV has not been detected in previous screening surveys of surface water samples collected from Oslofjord, whilst SVA was detected. One other metabolite that was detected in the surface water and sediment samples collected from Oslofjord was OHMET, which was present in the surface water samples collected at concentrations of between 25 and 108 ng L-1 and in the sediments collected at very low ng g-1 concentrations.
Spectrum
Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive
Experimental Conditions
Ionization Mode: Positive
Ionization Energy: 70 eV
Chromatography Type: Gas Chromatography Column (GC)
Instrument Type: Single quadrupole, spectrum predicted by CFM-ID(EI)
Mass Resolution: 0.0001 Da
Molecular Formula: C25H38O5
Molecular Weight (Monoisotopic Mass): 418.2719 Da
Molecular Weight (Avergae Mass): 418.5662 Da
Ionization Energy: 70 eV
Chromatography Type: Gas Chromatography Column (GC)
Instrument Type: Single quadrupole, spectrum predicted by CFM-ID(EI)
Mass Resolution: 0.0001 Da
Molecular Formula: C25H38O5
Molecular Weight (Monoisotopic Mass): 418.2719 Da
Molecular Weight (Avergae Mass): 418.5662 Da
LC-MS/MS Spectrum - LC-ESI-qTof , Positive
Experimental Conditions
Instrument Type: LC-ESI-qTof
Ionization Mode: Positive
Ionization Mode: Positive
Predicted LC-MS/MS Spectrum - 10V, Positive
Experimental Conditions
Ionization Mode: Positive
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C25H38O5
Molecular Weight (Monoisotopic Mass): 418.2719 Da
Molecular Weight (Avergae Mass): 418.5662 Da
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C25H38O5
Molecular Weight (Monoisotopic Mass): 418.2719 Da
Molecular Weight (Avergae Mass): 418.5662 Da
Mass Spectrum (Electron Ionization)
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
