Available from stock

Lovastatin

SKU: L0281

Categories:

Synonyms: Mevilonin , MK-803 , 6-α-Methylcompactin , BRN 3631989; 75330-75-5
CAS-Number: C₂₄H₃₆O₅
Molecular Formula: 404.54
Molecular Weight

For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.

Product Data
Handling
Safety Information
Details

Specifications

Purity: ≥98% (HPLC)
Appearance: White to off-white crystalline powder
Identity: 1H-NMR

Properties

Solvents: DMSO (20 mg/ml), DMF (15 mg/ml), ethanol (20 mg/ml), water (insoluble)
Melting Point: 175.4° C
Optical Activity: 320°±10°, c = 0.5 in CH3CN
Refractive Index: 1.53

Shipping: AMBIENT
Short Term Storage: RT
Long Term Storage: +4°C
Handling Advice: Protect from light and moisture.
Use / Stability: Stable for at least 2 years after receipt when stored at +4°C.

Hazard statements: H302
GHS Symbol: GHS07
Signal word: Warning
Transportation: Not dangerous goods

Description: Lovastatin is an inhibitor of 3-hydroxy-3-methylglutaryl-coenzyme A reductase (HMG-CoA reductase), an enzyme that catalyzes the conversion of HMG-CoA to mevalonate. Lovastatin is a prodrug, which is hydrolyzed in vivo to the active β-hydroxy acid open ring form. Mevalonate is a required building block for cholesterol biosynthesis and lovastatin interferes with its production by acting as a reversible competitive inhibitor for HMG-CoA. Lovastatin is an effective anti-hypercholesterolemic agent widely used as a lipid-lowering drug. In addition to lowering blood lipid levels, Lovastatin also has been shown to have anticancer, neuroprotective, anti-inflammatory, antiviral and antibacterial properties.
Smiles: C[C@H]1C=CC2=C[C@H](C)C[C@H](OC([C@@H](C)CC)=O)[C@]2([H])[C@H]1CC[C@H]3OC(C[C@H](O)C3)=O
InChi Key: PCZOHLXUXFIOCF-BXMDZJJMSA-N
References: (1) A.W. Alberts, et al., PNAS 77, 3957 (1980) , (2) M. Jakobisiak, et al., PNAS 88, 3628 (1991) , (3) P. Negre-Aminou, et al., Biochim. Biophys. Acta 1345, 259 (1997) , (4) B. Kwak, et al., Nat. Med. 6, 1399 (2000) , (5) C. Wojcik, et al., Int. J. Biochem. Cell Biol. 32, 957 (2000) , (6) L.J. Raggatt & N.C. Partridge, Drugs 62, 2185 (2002) (Review) , (7) W.W. Wong, et al., Leukemia 16, 508 (2002) , (8) K.K. Chan, et al., Clin. Cancer Res. 9,10 (2003) , (9) L.M. Blanco-Colio, et al., Kidney Int. 63, 12 (2003) , (10) J.A. Tobert, Nat. Rev. Drug Discov. 2, 517 (2003) (Review) , (11) V. Chopra, et al., Cardiovasc. Drugs Ther. 21, 161 (2007) , (12) Z. Xiong, et al., Food Chem. Toxicol. 131, 110585 (2019) (Review)
InChi: InChI=1S/C24H36O5/c1-5-15(3)24(27)29-21-11-14(2)10-17-7-6-16(4)20(23(17)21)9-8-19-12-18(25)13-22(26)28-19/h6-7,10,14-16,18-21,23,25H,5,8-9,11-13H2,1-4H3/t14-,15-,16-,18+,19+,20-,21-,23-/m0/s1

Lovastatin is an inhibitor of 3-hydroxy-3-methylglutaryl-coenzyme A reductase (HMG-CoA reductase), an enzyme that catalyzes the conversion of HMG-CoA to mevalonate. Lovastatin is a prodrug, which is hydrolyzed in vivo to the active β-hydroxy acid open ring form. Mevalonate is a required building block for cholesterol biosynthesis and lovastatin interferes with its production by acting as a reversible competitive inhibitor for HMG-CoA. Lovastatin is an effective anti-hypercholesterolemic agent widely used as a lipid-lowering drug. In addition to lowering blood lipid levels, Lovastatin also has been shown to have anticancer, neuroprotective, anti-inflammatory, antiviral and antibacterial properties.

SKU: L0281

Additional information

Additional information

Synonyms	Mevilonin, MK-803, 6-α-Methylcompactin, BRN 3631989
Purity	≥98% (HPLC)
Appearance	White to off-white crystalline powder
CAS-Number	75330-75-5
Molecular Formula	C24H36O5
Molecular Weight	404.54
Identity	1H-NMR
Solvents	DMSO (20 mg/ml), DMF (15 mg/ml), ethanol (20 mg/ml), water (insoluble)
Melting Point	175.4° C
Optical Activity	320°±10°, c = 0.5 in CH3CN
Refractive Index	1.53
Smiles	C[C@H]1C=CC2=C[C@H](C)C[C@H](OC([C@@H](C)CC)=O)[C@]2([H])[C@H]1CC[C@H]3OC(C[C@H](O)C3)=O
InChi Key	PCZOHLXUXFIOCF-BXMDZJJMSA-N
Shipping	AMBIENT
Short Term Storage	RT
Long Term Storage	+4°C
Handling Advice	Protect from light and moisture.
Use / Stability	Stable for at least 2 years after receipt when stored at +4°C.
Hazard statements	H302
GHS Symbol	GHS07
Signal word	Warning
Transportation	Not dangerous goods
References	(1) A.W. Alberts, et al., PNAS 77, 3957 (1980), (2) M. Jakobisiak, et al., PNAS 88, 3628 (1991), (3) P. Negre-Aminou, et al., Biochim. Biophys. Acta 1345, 259 (1997), (4) B. Kwak, et al., Nat. Med. 6, 1399 (2000), (5) C. Wojcik, et al., Int. J. Biochem. Cell Biol. 32, 957 (2000), (6) L.J. Raggatt & N.C. Partridge, Drugs 62, 2185 (2002) (Review), (7) W.W. Wong, et al., Leukemia 16, 508 (2002), (8) K.K. Chan, et al., Clin. Cancer Res. 9,10 (2003), (9) L.M. Blanco-Colio, et al., Kidney Int. 63, 12 (2003), (10) J.A. Tobert, Nat. Rev. Drug Discov. 2, 517 (2003) (Review), (11) V. Chopra, et al., Cardiovasc. Drugs Ther. 21, 161 (2007), (12) Z. Xiong, et al., Food Chem. Toxicol. 131, 110585 (2019) (Review)
InChi	InChI=1S/C24H36O5/c1-5-15(3)24(27)29-21-11-14(2)10-17-7-6-16(4)20(23(17)21)9-8-19-12-18(25)13-22(26)28-19/h6-7,10,14-16,18-21,23,25H,5,8-9,11-13H2,1-4H3/t14-,15-,16-,18+,19+,20-,21-,23-/m0/s1
Quantity	25 mg, 100 mg, Bulk