73573-88-3

73573-88-3 structure

Name: Mevastatin
Chemical Name: mevastatin
CAS Number: 73573-88-3
Molecular Formula: C₂₃H₃₄O₅
Molecular Weight: 390.513
Catalog: API Circulatory system medication Regulating blood lipids
Create Date: 2018-06-20 19:10:30
Modify Date: 2024-01-02 20:42:07
Mevastatin (Compactin; ML236B) inhibits HMGCR (HMG-CoA reductase) (Ki for acid form is 1 nM) which in turn inhibits isoprenoid biosynthesis and therefore blocks protein isoprenylation and reduces plasma cholesterol levels in humans. IC50 value: 1 nM (Ki)Target: HMGCRMevastatin induces apoptosis, arrests cancer cells in G1 phase and downregulates cdk 2, 4, and 6, cyclin D1 and E1, p21 and p27. Mevastatin suppresses TNF-induced NF-κB activation (IC50 = ~17 uM), which potentiates apoptosis in human myeloid leukemia cells and thus, may be useful in treating cancer.

Name	mevastatin
Synonyms	ML 236B Mevastatinum [INN-Latin] mevastatin Compactin (penicillium) Antibiotic ML 236B L66 AU IUTJ EOVY2&1 H1 G2- FT6OVTJ DQ &&stereoisomer Mevastatin (Compactin) MFCD05662341 Statin I [(1S,7S,8S,8aR)-8-[2-[(2R,4R)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] (2S)-2-methylbutanoate (+)-Compactin ML 236 B (1S,7S,8S,8aR)-8-{2-[(2R,4R)-4-Hydroxy-6-oxotetrahydro-2H-pyran-2-yl]ethyl}-7-methyl-1,2,3,7,8,8a-hexahydro-1-naphthalenyl (2S)-2-methylbutanoate Butanoic acid, 2-methyl-, (1S,7S,8S,8aR)-1,2,3,7,8,8a-hexahydro-7-methyl-8-[2-[(2R,4R)-tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl]ethyl]-1-naphthalenyl ester, (2S)- 2b-Methyl-8a-(2-methyl-1-oxobutoxy)mevinic acid lactone ML-236B (1S,7S,8S,8aR)-8-{2-[(2R,4R)-4-Hydroxy-6-oxotetrahydro-2H-pyran-2-yl]ethyl}-7-methyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl (2S)-2-methylbutanoate 7-[1,2,6,7,8,8a-Hexahydro-2-methyl-8-(methylbutyryloxy)naphthyl]-3-hydroxyheptan-5-olide [1S-[1a(R),7b,8b(2S,4S*),8ab]]-2-Methylbutanoic acid 1,2,3,7,8,8a-hexahydro-7-methyl-8-[2-(tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl]-1-naphthalenyl ester Compactin Lovastatin Impurity 1

Description	Mevastatin (Compactin; ML236B) inhibits HMGCR (HMG-CoA reductase) (Ki for acid form is 1 nM) which in turn inhibits isoprenoid biosynthesis and therefore blocks protein isoprenylation and reduces plasma cholesterol levels in humans. IC50 value: 1 nM (Ki)Target: HMGCRMevastatin induces apoptosis, arrests cancer cells in G1 phase and downregulates cdk 2, 4, and 6, cyclin D1 and E1, p21 and p27. Mevastatin suppresses TNF-induced NF-κB activation (IC50 = ~17 uM), which potentiates apoptosis in human myeloid leukemia cells and thus, may be useful in treating cancer.
Related Catalog	Signaling Pathways >> Autophagy >> Autophagy Signaling Pathways >> Metabolic Enzyme/Protease >> HMG-CoA Reductase (HMGCR) Research Areas >> Cancer
References	[1]. Sugazaki M, Hirotani H, Echigo S, et al. Effects of mevastatin on grafted bone in MRL/MpJ mice. Connect Tissue Res. 2010 Apr;51(2):105-12. doi: 10.3109/03008200903105098. [2]. Evangelopoulos ME, Weis J, Krüttgen A. Mevastatin-induced neurite outgrowth of neuroblastoma cells via activation of EGFR. J Neurosci Res. 2009 Jul;87(9):2138-44. doi: 10.1002/jnr.22025. [3]. W?chtersh?user A, Akoglu B, Stein J. HMG-CoA reductase inhibitor mevastatin enhances the growth inhibitory effect of butyrate in the colorectal carcinoma cell line Caco-2. Carcinogenesis. 2001 Jul;22(7):1061-7. [4]. Amin-Hanjani S, Stagliano NE, Yamada M, et al. Mevastatin, an HMG-CoA reductase inhibitor, reduces stroke damage and upregulates endothelial nitric oxide synthase in mice. Stroke. 2001 Apr;32(4):980-6.

Density	1.1±0.1 g/cm3
Boiling Point	555.0±50.0 °C at 760 mmHg
Melting Point	151-153 °C
Molecular Formula	C₂₃H₃₄O₅
Molecular Weight	390.513
Flash Point	186.5±23.6 °C
Exact Mass	390.240631
PSA	72.83000
LogP	3.57
Vapour Pressure	0.0±3.4 mmHg at 25°C
Index of Refraction	1.535
Storage condition	2-8°C
Water Solubility	DMSO: 20 mg/mL

CHEMICAL IDENTIFICATION

RTECS NUMBER :: EK7907100

CHEMICAL NAME :: Butanoic acid, 2-methyl-, 1,2,3,7,8,8a-hexahydro-7-methyl-8-(2-(tetrahydro-4-hy droxy-6-oxo-2H-pyran- 2-yl)ethyl)-1-naphthalenyl ester, (1S-(1-alpha(R*),7-beta,8-beta(2S*,4S*),8a-beta))-

CAS REGISTRY NUMBER :: 73573-88-3

LAST UPDATED :: 199212

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C23-H34-O5

MOLECULAR WEIGHT :: 390.57

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD - Lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >2 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JANTAJ Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo, 141, Japan) V.2-5, 1948-52; V.21- 1968- Volume(issue)/page/year: 29,1346,1976

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 500 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JANTAJ Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo, 141, Japan) V.2-5, 1948-52; V.21- 1968- Volume(issue)/page/year: 29,1346,1976

Personal Protective Equipment	Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter
Hazard Codes	T+
Risk Phrases	R26/27/28
Safety Phrases	S22-S24/25
RIDADR	NONH for all modes of transport
WGK Germany	3
RTECS	EK7907100

Precursor 5
84751-53-1 79814-60-1 84131-75-9 84173-21-7
2906-93-6
DownStream 4
81093-37-0 81131-70-6 67-64-1 75-65-0