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Lovastatin

Lovastatin structure

CAS No:
75330-75-5
Formula:
C24H36O5
Chemical Name:
Lovastatin
Synonyms:
SiMvastatin EP IMpurity E;Lovastatin,Monacolin K;8-[2-(4-Hydroxy-6-oxotetrahydro-2H-pyran-2-yl)ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydro-1-nap;6alpha-Methylcompactin Mevinolin Monacolin K;)ethyl]-1-naphthalenylester;[1s-[1alpha(r*),3alpha,7beta,8beta(2s*,4s*),8abeta]]-2-methylbutanoicacid1,2,;1,2,6,7,8,8a-hexahydro-beta,delta-dihydroxy-2,6-dimethyl-8-(2-methyl-1-oxobuty;2-methyl-,1,2,3,7,8,8a-hexahydro-3,7-dimethyl-8-(2-(tetrahydro-butanoicaci
Categories:
Active Pharmaceutical Ingredients > Circulatory System Drugs

Description

Lovastatin is a cell-permeable HMG-CoA reductase inhibitor used to lower cholesterol.

Lovastatin is an orally-active hypocholesterolemic useful in the treatment of familial hypercholesterolemia. The drug acts by inhibiting the HMG-CoA reductase-catalyzed rate limiting step of cholesterol biosynthesis. While treatment with lovastatin leads to significant reductions in total and LDL cholesterol, its effect on atherosclerosis or coronary heart disease has not been established.

White Solid

Statins are the most extensively used class of lipid-lowering medication. Lovastatin is the second statin discovered by scientists.Later, the official name lovastatin was established. The activity of lovastatin is much better than compactin.In July 1982, lovastatin showed dramatic effects on lowering LDL cholesterol in patients with severe hypercholesterolemia who were unresponsive to the existedmedicines, with very few adverse reactions .

ChEBI: Lovastatin is a fatty acid ester that is mevastatin carrying an additional methyl group on the carbobicyclic skeleton. It is used in as an anticholesteremic drug and has been found in fungal species such as Aspergillus terreus and Pleurotus ostreatus (oyster mushroom). It has a role as an Aspergillus metabolite, a prodrug, an anticholesteremic drug and an antineoplastic agent. It is a polyketide, a statin (naturally occurring), a member of hexahydronaphthalenes, a delta-lactone and a fatty acid ester. It is functionally related to a (S)-2-methylbutyric acid and a mevastatin.

Lovastatin Basic Attributes

Molecular Weight：

404.54

Exact Mass：

404.54

EC Number：

616-212-7

Color/Form：

White

HScode：

29322090

Characteristics

PSA：

72.8

Physical Properties：

Appearance: White, nonhygroscopic crystalline powder. Solubility: Insoluble in water (0.0004mg/mL); sparingly soluble in ethanol, methanol, isobutanol, isopropanol, acetonitrile, n-propanol; soluble in acetone, N-dimethylformamide; freely soluble in chloroform. Melting point: 174.5°C. Specific optical rotation: 25°C for D (sodium) line, +323° (concentration 0.5 g in 100 ml acetonitrile). Stability: Lovastatin is sensitive to light. Following exposure to extreme light conditions, the drug is stable for 24h or 1month when exposed to UV (approximately 3230 lux) or fluorescent (approximately 10,764 lux) light, respectively, at 28°C in air.

XLogP3：

4.08

Appearance：

Solid

Density：

1.12±0.1 g/cm3(Predicted)

Melting Point：

175°C

Boiling Point：

559.2±50.0 °C(Predicted)

Flash Point：

185.3±23.6 °C

Refractive Index：

320 ° (C=0.5, CH3CN)

Water Solubility：

0.0004 mg/mL at 25 ºC

Storage Conditions：

2-8°C

Vapor Pressure：

0Pa at 25℃

Toxicity：

LD50 orally in mice: >1000 mg/kg (Endo)

Specific rotation：

D25 +323° (c = 0.5 g in 100 ml acetonitrile)

PKA：

13.49±0.40(Predicted)

Critical Temperature & Pressure：

-20°C

Safety Information

Packing level：

III

Hazard category：

Transport codes：

3077

wgk germany：

hazard class code：

safety instructions：

22-24/25-36/37/39-26

RTECS Number：

EK7907000

Marks：

Storage features：

Store at RT

Stability/Shelf Life：

Stable under recommended storage conditions.

Precautionary statement(s)：

P301 + P312 + P330

Hazard Statements：

36/37/38

RIDADR：

3077

Lovastatin Use and Manufacturing

Methods of Manufacturing

Lovastatin is obtained by fermentation. Available strains are: ①Monescus ruber; ②Monescus purpureus; ③Monescus pilosus; ④Aspergillus terreus; ⑤Penicillium Citrunum. When Monescus ruber is used as the strain, the culture medium is: 6% glucose, 2.5% peptone, 0.5% corn steep liquor, 0.5% ammonium chloride. The strains and the culture solution were cultured together under aerobic conditions at 28℃ for 10 days. 5 L of the filtrate was filtered and extracted with 5 L of ethyl acetate with a Ph value of 3. The extract was concentrated to dryness in vacuo, and the residue was dissolved in 100 ml of benzene. The insoluble material was removed by filtration, and the filtrate was washed twice with 100 ml of 5% sodium carbonate aqueous solution, and then stirred with 100 ml of 0.2 mol/L sodium hydroxide solution at room temperature for 2 h. The aqueous layer was collected, adjusted to Ph=3 with 6 mol/L hydrochloric acid, and extracted twice with 100 ml of ethyl acetate. The extracts were combined and evaporated to dryness to obtain 260 mg of oil. Dissolve the oil in a small amount of benzene, and recrystallize the obtained crystals with a mixture of acetone and water to obtain 87 mg of colorless lovastatin crystals, melting point 157～159°C (decomposition), [α]D23+307.6° (C=1, methanol).

Uses

Cardiovascular

It is used for treating heterozygous familial and non familial, secondary hyperlipidemia, namely diabetes and nephrotic syndrome secondary hypercholesterolemia. It can reduce the level of TC, LF, LDL-C, and increase the level of HDL-C, reduce the risk of myocardial infarction, unstable angina and the necessity for percutaneous transluminal coronary angioplasty (PTCA).

1. It is as a novel lipid regulating drugs-The inhibitor of HMG-CoA (β-hydroxy, β-methyl-glutaryl coenzyme A) reductase. It can significantly reduced serum total cholesterol level. After oral administration, it is hydrolyzed into corresponding β-hydroxy acid by 3-hydroxy-3-methylglutaryl coenzyme A reductase, and thus inhibiting the cholesterol biosynthesis. It is clinically used for treating heterozygous familial hypercholesterolemia, severe or mild hypercholesterolemia and light. It can also as an ancillary drug of dietary treatment for reducing the levels of excessively cholesterol and low-density protein cholesterol.2. It is a cardiovascular systematic drug which can prevent the development of atherosclerosis and reduce the risk of myocardial infarction.

An antihypercholesterolemic agent. A fungal metabolite, which is a potent inhibitor of HMG-CoA reductase

antiarrhythmic

Downstream Products

Acetone

tert-Butanol

Drug Function and Efficacy

Extract from the above information

This ingredient has been used in drugs with the following functions (note: it does not mean that the ingredient itself has the following health functions)

Related Drugs

Lovastatin

Lovastatin
Manufacturer	Wichita, Its Group of Pharmaceutical Co., Ltd.

Lovastatin Capsules
Ingredients	Main ingredients: The main ingredient of this product is lovastatin. Its chemical name is (S)-2-methylbutyric acid-(1S,3S,7S,8S,8aR)1,2,3,7,8,8a-hexahydro-3,7-dimethyl-8-{2-[(2R,4R)-4-hydroxy-6-oxo-2-tetrahydropyranyl]-ethyl}-1-naphthyl ester. Molecular formula: C24H36O5, molecular weight: 404.55.
Indication	1. The combination of this product with oral anticoagulants can prolong the prothrombin time and increase the risk of bleeding. 2. The combination of this product with immunosuppressants such as cyclosporine, azithromycin, clarithromycin, erythromycin, danazol, itraconazole, gemfibrozil, niacin, etc. can increase the risk of myolysis and acute renal failure. 3. Colestipol and cholestyramine can reduce the bioavailability of this product, so this product should be taken 4 hours after taking the former.
Specifications	20 mg
Manufacturer	Bikang Pharmaceutical Xinyi Group Holdings Co., Ltd.

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Registered Holders

Chongqing Xinda New Pharmaceutical Co., Ltd.

China
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LIVZON GROUP (NINGXIA) PHARMACEUTICAL CO LTD

United States
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