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MedKoo Cat#: 326777 | Name: Mevastatin
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

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. 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]

Chemical Structure

Mevastatin
Mevastatin
CAS#73573-88-3

Theoretical Analysis

MedKoo Cat#: 326777

Name: Mevastatin

CAS#: 73573-88-3

Chemical Formula: C23H34O5

Exact Mass: 390.2406

Molecular Weight: 390.52

Elemental Analysis: C, 70.74; H, 8.78; O, 20.48

Price and Availability

Size Price Availability Quantity
5g USD 250.00 Ready to ship
10g USD 450.00 Ready to ship
20g USD 750.00 Ready to ship
100g USD 1,650.00 Ready to ship
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Related CAS #
No Data
Synonym
CS-500; CS 500; CS500; CS-500; ML-236B; ML 236B; ML236B; Mevastatin, Compactin.
IUPAC/Chemical Name
(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 (S)-2-methylbutanoate
InChi Key
AJLFOPYRIVGYMJ-INTXDZFKSA-N
InChi Code
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
SMILES Code
CC[C@H](C)C(O[C@H]1CCC=C2C=C[C@H](C)[C@H](CC[C@@H]3C[C@@H](O)CC(O3)=O)[C@@]12[H])=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Biological target:
Mevastatin (ML-236B) is a competitive inhibitor of HMG-Coenzyme A (HMG-CoA) reductase with a binding affinity 10,000 times greater than the HMG-CoA substrate itself.
In vitro activity:
It was found that mevastatin triggered neurite outgrowth of neuroblastoma cells and examined the responsible signaling pathways. Treatment of Neuro2a cells with mevastatin for 24 hr induced neurite outgrowth associated with up-regulation of the neuronal marker protein NeuN. It was also found that mevastatin triggered phosphorylation of the key kinases epidermal growth factor receptor (EGFR), ERK1/2, and Akt/protein kinase B. Inhibition of EGFR, PI3K, and the mitogen-activated protein kinase cascade blocked mevastatin-induced neurite outgrowth. Moreover, add-back experiments of cell-permeable cholesterol precursors indicated that farnesylated and geranylgeranylated proteins play a major role in statin-induced neurite outgrowth. Reference: J Neurosci Res. 2009 Jul;87(9):2138-44. https://doi.org/10.1002/jnr.22025
In vivo activity:
The present study was undertaken to determine whether the topical administration of mevastatin could increase the bone mass of isografted bone. The tibiae were bilaterally dissected from a donor MRL/MpJ mouse and transplanted subcutaneously in the dorsal region of a recipient mouse. One grafted tibia was topically infused for either 1, 2, 3, or 4 weeks with mevastatin, using an osmotic minipump at a dose of 2.5 pmol/hr. The other tibia was infused with 0.9% NaCl (control). The three results were: (1) Topical mevastatin stimulated bone formation and numerous cuboidal osteoblasts appeared on the surface of newly formed bone. Bone mineral density and bone area in mevastatin-treated bone were significantly increased. (2) Topical mevastatin increased the number of osteoclasts. (3) The expression of bone morphogenetic protein-2 (BMP-2) mRNA and receptor activator of NF-kB ligand (RANKL) mRNA were upregulated in mevastatin-treated bone. These results suggest that the topical infusion of mevastatin increases bone mass of isografted bone by increasing bone turnover and, at least in part, by promoting the expression of BMP-2 and RANKL mRNA. Reference: Connect Tissue Res. 2010 Apr;51(2):105-12. https://www.tandfonline.com/doi/full/10.3109/03008200903105098
Solvent mg/mL mM
Solubility
DMSO 78.0 199.74
Ethanol 7.0 17.93
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 390.52 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
1. 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. PMID: 19224573. 2. Sawaya AP, Jozic I, Stone RC, Pastar I, Egger AN, Stojadinovic O, Glinos GD, Kirsner RS, Tomic-Canic M. Mevastatin promotes healing by targeting caveolin-1 to restore EGFR signaling. JCI Insight. 2019 Dec 5;4(23):e129320. doi: 10.1172/jci.insight.129320. PMID: 31661463; PMCID: PMC6962014.
In vivo protocol:
1. Sugazaki M, Hirotani H, Echigo S, Takeyama S, Shinoda H. Effects of mevastatin on grafted bone in MRL/MpJ mice. Connect Tissue Res. 2010 Apr;51(2):105-12. doi: 10.3109/03008200903105098. PMID: 20109072.
1: Lee HJ, Jo SY, Hwang JS, Chang SE. Mevastatin suppresses melanogenesis by lowering the levels of cyclic adenosine monophosphate and cholesterol. Exp Dermatol. 2016 Apr 27. doi: 10.1111/exd.13056. [Epub ahead of print] PubMed PMID: 27119271. 2: 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. 3: 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. 4: 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. 5: 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. 6: Yilmaz A, Menevse S, Konac E, Alp E. The DNA methyl transferase inhibitor, 5'-aza-2-deoxycitidine, enhances the apoptotic effect of Mevastatin in human leukemia HL-60 cells. Hum Exp Toxicol. 2014 Apr;33(4):414-23. doi: 10.1177/0960327113499050. Epub 2013 Aug 5. PubMed PMID: 23918904. 7: Zhang S, Wang XL, Gan YH, Li SL. Activation of c-Jun N-terminal kinase is required for mevastatin-induced apoptosis of salivary adenoid cystic carcinoma cells. Anticancer Drugs. 2010 Aug;21(7):678-86. PubMed PMID: 20629200. 8: Yi W, Xu X. [Mevastatin inhibits the differentiation of thyroid-associated ophthalmopathy derived orbital preadipocytes]. Zhong Nan Da Xue Xue Bao Yi Xue Ban. 2010 May;35(5):511-7. doi: 10.3969/j.issn.1672-7347.2010.05.017. Chinese. PubMed PMID: 20543477. 9: Bashmakov YK, Zigangirova NA, Pashko YP, Kapotina LN, Petyaev IM. Chlamydia trachomatis growth inhibition and restoration of LDL-receptor level in HepG2 cells treated with mevastatin. Comp Hepatol. 2010 Jan 28;9:3. doi: 10.1186/1476-5926-9-3. PubMed PMID: 20181044; PubMed Central PMCID: PMC2835644. 10: Sugazaki M, Hirotani H, Echigo S, Takeyama S, Shinoda H. Effects of mevastatin on grafted bone in MRL/MpJ mice. Connect Tissue Res. 2010 Apr;51(2):105-12. doi: 10.3109/03008200903105098. PubMed PMID: 20109072. 11: Ahmad A, Panda BP, Mujeeb M. Screening of nutrient parameters for mevastatin production by Penicillium citrinum MTCC 1256 under submerged fermentation using the Plackett-Burman design. J Pharm Bioallied Sci. 2010 Jan;2(1):44-6. doi: 10.4103/0975-7406.62709. PubMed PMID: 21814430; PubMed Central PMCID: PMC3146091. 12: Campia I, Lussiana C, Pescarmona G, Ghigo D, Bosia A, Riganti C. Geranylgeraniol prevents the cytotoxic effects of mevastatin in THP-1 cells, without decreasing the beneficial effects on cholesterol synthesis. Br J Pharmacol. 2009 Dec;158(7):1777-86. doi: 10.1111/j.1476-5381.2009.00465.x. Epub . PubMed PMID: 19888963; PubMed Central PMCID: PMC2801219. 13: Evangelopoulos ME, Wüller S, Weis J, Krüttgen A. A role of nitric oxide in neurite outgrowth of neuroblastoma cells triggered by mevastatin or serum reduction. Neurosci Lett. 2010 Jan 1;468(1):28-33. doi: 10.1016/j.neulet.2009.10.054. Epub 2009 Oct 22. PubMed PMID: 19853642. 14: 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. PubMed PMID: 19224573. 15: Kannan M, Steinert JR, Forsythe ID, Smith AG, Chernova T. Mevastatin accelerates loss of synaptic proteins and neurite degeneration in aging cortical neurons in a heme-independent manner. Neurobiol Aging. 2010 Sep;31(9):1543-53. doi: 10.1016/j.neurobiolaging.2008.09.004. Epub 2008 Oct 31. PubMed PMID: 18951667. 16: Akasaki Y, Matsuda S, Nakayama K, Fukagawa S, Miura H, Iwamoto Y. Mevastatin reduces cartilage degradation in rabbit experimental osteoarthritis through inhibition of synovial inflammation. Osteoarthritis Cartilage. 2009 Feb;17(2):235-43. doi: 10.1016/j.joca.2008.06.012. Epub 2008 Jul 30. PubMed PMID: 18672387. 17: Glynn SA, O'Sullivan D, Eustace AJ, Clynes M, O'Donovan N. The 3-hydroxy-3-methylglutaryl-coenzyme A reductase inhibitors, simvastatin, lovastatin and mevastatin inhibit proliferation and invasion of melanoma cells. BMC Cancer. 2008 Jan 16;8:9. doi: 10.1186/1471-2407-8-9. PubMed PMID: 18199328; PubMed Central PMCID: PMC2253545. 18: Schalkwijk CG, van Dam B, Stehouwer CD, van Hinsbergh VW. Mevastatin increases eNO synthase expression and inhibits lipid peroxidation in human endothelial cells. Clin Hemorheol Microcirc. 2007;37(1-2):179-84. PubMed PMID: 17641407. 19: Kwintkiewicz J, Foyouzi N, Piotrowski P, Rzepczynska I, Duleba AJ. Mevastatin inhibits proliferation of rat ovarian theca-interstitial cells by blocking the mitogen-activated protein kinase pathway. Fertil Steril. 2006 Oct;86(4 Suppl):1053-8. Epub 2006 Sep 11. PubMed PMID: 16963032. 20: Fleming CD, Bencharit S, Edwards CC, Hyatt JL, Tsurkan L, Bai F, Fraga C, Morton CL, Howard-Williams EL, Potter PM, Redinbo MR. Structural insights into drug processing by human carboxylesterase 1: tamoxifen, mevastatin, and inhibition by benzil. J Mol Biol. 2005 Sep 9;352(1):165-77. PubMed PMID: 16081098.

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