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Merck
CN

27696

Mevastatin

≥96% (HPLC)

Synonym(s):

Compactin, ML-236B

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About This Item

Empirical Formula (Hill Notation):
C23H34O5
CAS Number:
73573-88-3
Molecular Weight:
390.51
PubChem Substance ID:
329753015
UNSPSC Code:
12352200
Beilstein/REAXYS Number:
1269441
MDL number:
MFCD05662341

Key Documents

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assay

≥96% (HPLC)

mp

151-153 °C

antibiotic activity spectrum

fungi

mode of action

enzyme | inhibits

storage temp.

2-8°C

SMILES string

[H][C@]12[C@H](CCC=C1C=C[C@H](C)[C@@H]2CC[C@@H]3C[C@@H](O)CC(=O)O3)OC(=O)[C@@H](C)CC

InChI

1S/C23H34O5/c1-4-14(2)23(26)28-20-7-5-6-16-9-8-15(3)19(22(16)20)11-10-18-12-17(24)13-21(25)27-18/h6,8-9,14-15,17-20,22,24H,4-5,7,10-13H2,1-3H3/t14-,15-,17+,18+,19-,20-,22-/m0/s1

InChI key

AJLFOPYRIVGYMJ-INTXDZFKSA-N

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General description

Chemical structure: statin

Other Notes

Potent inhibitor of 3-hydroxy-3-methylglutaryl-CoA reductase, HMG-CoA reductase; Used e.g. in culturing compactin-resistant cell lines overaccumulating HMG-CoA reductase

Storage Class

13 - Non Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

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Competitive inhibition of 3-hydroxy-3-methylglutaryl coenzyme A reductase by ML-236A and ML-236B fungal metabolites, having hypocholesterolemic activity.
A Endo et al.
FEBS letters, 72(2), 323-326 (1976-12-31)
Ml Pinzón-Daza et al.
British journal of pharmacology, 167(7), 1431-1447 (2012-07-14)
The passage of drugs across the blood-brain barrier (BBB) limits the efficacy of chemotherapy in brain tumours. For instance, the anticancer drug doxorubicin, which is effective against glioblastoma in vitro, has poor efficacy in vivo, because it is extruded by
Induction of 3-hydroxy-3-methylglutaryl coenzyme A reductase activity in human fibroblasts incubated with compactin (ML-236B), a competitive inhibitor of the reductase.
M S Brown et al.
The Journal of biological chemistry, 253(4), 1121-1128 (1978-02-25)
C E Nakamura et al.
Biochemistry, 24(6), 1364-1376 (1985-03-12)
The sodium salts of compactin (1) and trans-6-[2-(2,4- dichloro-6-hydroxyphenyl)ethyl]-3,4,5,6-tetrahydro-4-hydroxy-2H-pyran- 2-one (3) are inhibitors of yeast beta-hydroxy-beta-methylglutaryl coenzyme A (HMG-CoA) reductase. The dissociation constants are 0.24 X 10(-9) and 0.28 X 10(-9) M, respectively. Similar values have been reported for HMG-CoA
Yiwei Zhao et al.
The Journal of investigative dermatology, 131(5), 1045-1052 (2011-03-11)
Pachyonychia congenita (PC) is a keratinizing disorder predominantly caused by mutations in keratin 6a (K6a) (∼50% of cases) or K6b, K16, or K17. One means of treating PC is identification of small-molecule inhibitors of PC-related keratins. Here, we cloned the
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