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'''Mevastatin''' ('''compactin''', '''ML-236B''') is a [[hypolipidemic agent]] that belongs to the [[statin]]s class.
'''Mevastatin''' ('''compactin''', '''ML-236B''') is a [[hypolipidemic agent]] that belongs to the [[statin]]s class.


It was isolated from the mold ''[[Penicillium citrinum]]'' by [[Akira Endo (biochemist)|Akira Endo]] in the 1970s, and he identified it as a [[HMG-CoA reductase inhibitor]],<ref>{{cite journal|first=Akira|last=Endo|author2=Kuroda M. |author3=Tsujita Y. |title=ML-236A, ML-236B, and ML-236C, new inhibitors of cholesterogenesis produced by Penicillium citrinium|journal=Journal of Antibiotics (Tokyo)|date=December 1976|volume=29|issue=12|pages=1346–8|pmid=1010803|doi=10.7164/antibiotics.29.1346}}</ref> i.e., a statin. Mevastatin might be considered the first statin drug;<ref>{{cite web | url = http://www.world-of-fungi.org/Mostly_Medical/Mark_Gilson/Mark_Gilson.htm | title = The story of statins}}{{dead link|date=March 2015}}</ref> clinical trials on mevastatin were performed in the late 1970s in Japan, but it was never marketed.<ref>{{cite journal|first= Akira|last= Endo|title= The origin of the statins |journal= Atheroscler Suppl. |date=Oct 2004|volume= 5|issue= 3|pages= 125–30|pmid= 15531285|doi=10.1016/j.atherosclerosissup.2004.08.033 }}</ref> The first statin drug available to the general public was [[lovastatin]].
It was isolated from the mold ''[[Penicillium citrinum]]'' by [[Akira Endo (biochemist)|Akira Endo]] in the 1970s, and he identified it as a [[HMG-CoA reductase inhibitor]],<ref>{{cite journal|first=Akira|last=Endo|author2=Kuroda M. |author3=Tsujita Y. |title=ML-236A, ML-236B, and ML-236C, new inhibitors of cholesterogenesis produced by Penicillium citrinium|journal=Journal of Antibiotics (Tokyo)|date=December 1976|volume=29|issue=12|pages=1346–8|pmid=1010803|doi=10.7164/antibiotics.29.1346}}</ref> i.e., a statin. Mevastatin might be considered the first statin drug;<ref>{{cite web|url=http://www.world-of-fungi.org/Mostly_Medical/Mark_Gilson/Mark_Gilson.htm |title=The story of statins |deadurl=yes |archiveurl=https://web.archive.org/20081221221223/http://www.world-of-fungi.org:80/Mostly_Medical/Mark_Gilson/Mark_Gilson.htm |archivedate=December 21, 2008 }}</ref> clinical trials on mevastatin were performed in the late 1970s in Japan, but it was never marketed.<ref>{{cite journal|first= Akira|last= Endo|title= The origin of the statins |journal= Atheroscler Suppl. |date=Oct 2004|volume= 5|issue= 3|pages= 125–30|pmid= 15531285|doi=10.1016/j.atherosclerosissup.2004.08.033 }}</ref> The first statin drug available to the general public was [[lovastatin]].


''[[In vitro]]'', it has antiproliferative properties.<ref>{{cite journal | doi = 10.1093/carcin/22.7.1061| pmid = 11408350| title = HMG-CoA reductase inhibitor mevastatin enhances the growth inhibitory effect of butyrate in the colorectal carcinoma cell line Caco-2| journal = Carcinogenesis| volume = 22| issue = 7| pages = 1061–7| year = 2001| last1 = Wachtershauser| first1 = A.| last2 = Akoglu| first2 = B| last3 = Stein| first3 = J}}</ref>
''[[In vitro]]'', it has antiproliferative properties.<ref>{{cite journal | doi = 10.1093/carcin/22.7.1061| pmid = 11408350| title = HMG-CoA reductase inhibitor mevastatin enhances the growth inhibitory effect of butyrate in the colorectal carcinoma cell line Caco-2| journal = Carcinogenesis| volume = 22| issue = 7| pages = 1061–7| year = 2001| last1 = Wachtershauser| first1 = A.| last2 = Akoglu| first2 = B| last3 = Stein| first3 = J}}</ref>

Revision as of 00:23, 14 January 2016

Mevastatin
Clinical data
ATC code
  • none
Identifiers
  • (1S,7R,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
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.131.541 Edit this at Wikidata
Chemical and physical data
FormulaC23H34O5
Molar mass390.513 g/mol g·mol−1
3D model (JSmol)
  • O=C(O[C@@H]1[C@H]3C(=C/CC1)\C=C/[C@@H]([C@@H]3CC[C@H]2OC(=O)C[C@H](O)C2)C)[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 checkY
  • Key:AJLFOPYRIVGYMJ-INTXDZFKSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Mevastatin (compactin, 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,[1] i.e., a statin. Mevastatin might be considered the first statin drug;[2] clinical trials on mevastatin were performed in the late 1970s in Japan, but it was never marketed.[3] The first statin drug available to the general public was lovastatin.

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]

See also

References

  1. ^ Endo, Akira; Kuroda M.; Tsujita Y. (December 1976). "ML-236A, ML-236B, and ML-236C, new inhibitors of cholesterogenesis produced by Penicillium citrinium". Journal of Antibiotics (Tokyo). 29 (12): 1346–8. doi:10.7164/antibiotics.29.1346. PMID 1010803.
  2. ^ "The story of statins". Archived from the original on December 21, 2008. {{cite web}}: Unknown parameter |deadurl= ignored (|url-status= suggested) (help)
  3. ^ Endo, Akira (Oct 2004). "The origin of the statins". Atheroscler Suppl. 5 (3): 125–30. doi:10.1016/j.atherosclerosissup.2004.08.033. PMID 15531285.
  4. ^ Wachtershauser, A.; Akoglu, B; Stein, J (2001). "HMG-CoA reductase inhibitor mevastatin enhances the growth inhibitory effect of butyrate in the colorectal carcinoma cell line Caco-2". Carcinogenesis. 22 (7): 1061–7. doi:10.1093/carcin/22.7.1061. PMID 11408350.
  5. ^ Brown, Allan G.; Smale, Terry C.; King, Trevor J.; Hasenkamp, Rainer; Thompson, Ronald H. (1976). "Crystal and molecular structure of compactin, a new antifungal metabolite from Penicillium brevicompactum". J. Chem. Soc., Perkin Trans. 1 (11): 1165–1170. doi:10.1039/P19760001165. PMID 945291.
  6. ^ Glynn, Sharon A; O'Sullivan, Dermot; Eustace, Alex J; Clynes, Martin; O'Donovan, Norma (2008). "The 3-hydroxy-3-methylglutaryl-coenzyme a reductase inhibitors, simvastatin, lovastatin and mevastatin inhibit proliferation and invasion of melanoma cells". BMC Cancer. 8: 9. doi:10.1186/1471-2407-8-9. PMC 2253545. PMID 18199328.{{cite journal}}: CS1 maint: unflagged free DOI (link)
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