Mevastatin

  • CAT Number: A000954
  • CAS Number: 73573-88-3
  • Molecular Formula: C₂₃H₃₄O₅
  • Molecular Weight: 390.51
  • Purity: ≥95%
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Mevastatin, CS-500 and ML-236B, is a hypolipidemic agent that belongs to the statins class. It was isolated from the mold Penicillium citrinum by Akira Endo in the 1970s, and he identified it as a HMG-CoA reductase inhibitor, i.e., a statin. Mevastatin might be considered the first statin drug; clinical trials on mevastatin were performed in the late 1970s in Japan, but it was never marketed. The first statin drug available to the general public was lovastatin. Mevastatin has since been derivatized to the compound pravastatin, which is a pharmaceutical used the in lowering cholesterol and preventing cardiovascular disease. (last updated: 7/20/2016). In vitro, it has antiproliferative properties.[4] A British group isolated the same compound from Penicillium brevicompactum, named it compactin, and published their results in 1976.[5] The British group mentions antifungal properties with no mention of HMG-CoA reductase inhibition. High doses inhibit growth and proliferation of melanoma cells.[6]

Catalog Number A000954
CAS Number 73573-88-3
Molecular Formula

C₂₃H₃₄O₅

Purity 95%
Target HMG-CoA Reductase
Solubility >16mg/mL in DMSO
Storage Store at -20°C
InChI 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
InChIKey AJLFOPYRIVGYMJ-INTXDZFKSA-N
SMILES CCC(C)C(=O)OC1CCC=C2C1C(C(C=C2)C)CCC3CC(CC(=O)O3)O
Reference

1: Sawaya AP, Pastar I, Stojadinovic O, Lazovic S, Davis SC, Gil J, Kirsner RS,
Tomic-Canic M. Topical mevastatin promotes wound healing by inhibiting the
transcription factor c-Myc via the glucocorticoid receptor and the long noncoding
RNA Gas5. J Biol Chem. 2017 Nov 20. pii: jbc.M117.811240. doi:
10.1074/jbc.M117.811240. [Epub ahead of print] PubMed PMID: 29158265.
<br>

2: Kornelius E, Li HH, Peng CH, Hsiao HW, Yang YS, Huang CN, Lin CL. Mevastatin
promotes neuronal survival against Aβ-induced neurotoxicity through AMPK
activation. Metab Brain Dis. 2017 Dec;32(6):1999-2007. doi:
10.1007/s11011-017-0091-4. Epub 2017 Aug 24. PubMed PMID: 28840430.
<br>

3: Lin Z, Zhang Z, Jiang X, Kou X, Bao Y, Liu H, Sun F, Ling S, Qin N, Jiang L,
Yang Y. Mevastatin blockade of autolysosome maturation stimulates LBH589-induced
cell death in triple-negative breast cancer cells. Oncotarget. 2017 Mar
14;8(11):17833-17848. doi: 10.18632/oncotarget.14868. PubMed PMID: 28147319;
PubMed Central PMCID: PMC5392290.
<br>

4: Milhim M, Putkaradze N, Abdulmughni A, Kern F, Hartz P, Bernhardt R.
Identification of a new plasmid-encoded cytochrome P450 CYP107DY1 from Bacillus
megaterium with a catalytic activity towards mevastatin. J Biotechnol. 2016 Dec
20;240:68-75. doi: 10.1016/j.jbiotec.2016.11.002. Epub 2016 Nov 2. PubMed PMID:
27816653.

<br>
5: Lee HJ, Jo SY, Hwang JS, Chang SE. Mevastatin suppresses melanogenesis by
lowering the levels of cyclic adenosine monophosphate and cholesterol. Exp
Dermatol. 2016 Oct;25(10):820-2. doi: 10.1111/exd.13056. Epub 2016 Jul 13. PubMed
PMID: 27119271.
<br>

6: Javed S, Bukhari SA, Ali M, Sajjad-ur-Rehman. Estimation of Antifungal
Activity of Mevastatin Produced by Aspergillus terreus GCBL-03 on pretreated
substrate in solid state fermentation. Curr Pharm Biotechnol. 2016;17(3):291-8.
PubMed PMID: 26873078.
<br>

7: Hsu CK, Lin CC, Hsiao LD, Yang CM. Mevastatin ameliorates sphingosine
1-phosphate-induced COX-2/PGE2-dependent cell migration via FoxO1 and CREB
phosphorylation and translocation. Br J Pharmacol. 2015 Nov;172(22):5360-76. doi:
10.1111/bph.13326. Epub 2015 Oct 23. PubMed PMID: 26359950; PubMed Central PMCID:
PMC5341221.
<br>

8: Dinesh N, Soumya N, Singh S. Antileishmanial effect of mevastatin is due to
interference with sterol metabolism. Parasitol Res. 2015 Oct;114(10):3873-83.
doi: 10.1007/s00436-015-4618-5. Epub 2015 Jul 18. PubMed PMID: 26183607.
<br>

9: Zheng Y, Cao S, Huang Y, Liao G, Hu C. [Overexpression of LaeA enhances
mevastatin production and reduces sporulation of Penicillium citrinum]. Wei Sheng
Wu Xue Bao. 2014 Dec 4;54(12):1438-45. Chinese. PubMed PMID: 25876329.
<br>

10: Syed MB, Rajasimman M. Fermentative production and optimization of mevastatin
in submerged fermentation using Aspergillus terreus. Biotechnol Rep (Amst). 2015
Apr 9;6:124-128. doi: 10.1016/j.btre.2015.04.002. eCollection 2015 Jun. PubMed
PMID: 28435810; PubMed Central PMCID: PMC5374293.

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