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Fumarranol

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Chemical compound Pharmaceutical compound
Fumarranol
Identifiers
IUPAC name
  • (1S,5S)-5-(hydroxymethyl)-1-methoxy-6-bicyclohexan-2-one
CAS Number
PubChem CID
Chemical and physical data
FormulaC16H24O4
Molar mass280.364 g·mol
3D model (JSmol)
SMILES
  • CC(=CC1(O1)(C)C23(2(C(=O)CC3)OC)CO)C
InChI
  • InChI=1S/C16H24O4/c1-10(2)5-6-12-14(3,20-12)13-15(9-17)8-7-11(18)16(13,15)19-4/h5,12-13,17H,6-9H2,1-4H3/t12-,13?,14+,15-,16+/m1/s1
  • Key:CANZHCRPLGNWCR-LMINUHAASA-N

Fumarranol is a drug which acts as an inhibitor of the type 2 methionine aminopeptidase enzyme METAP2. It was derived by structural modification of the natural product fumagillin. It was originally developed as an anti-angiogenesis drug for the treatment of cancer, but it was subsequently found to bind with high affinity to the METAP2 enzyme in malaria parasites and has been investigated as a potential treatment for malaria.

See also

References

  1. Lu J, Chong CR, Hu X, Liu JO (September 2006). "Fumarranol, a rearranged fumagillin analogue that inhibits angiogenesis in vivo". Journal of Medicinal Chemistry. 49 (19): 5645–8. doi:10.1021/jm060559v. PMID 16970390.
  2. Chen X, Xie S, Bhat S, Kumar N, Shapiro TA, Liu JO (February 2009). "Fumagillin and fumarranol interact with P. falciparum methionine aminopeptidase 2 and inhibit malaria parasite growth in vitro and in vivo". Chemistry & Biology. 16 (2): 193–202. doi:10.1016/j.chembiol.2009.01.006. PMID 19246010.
  3. Deu E (August 2017). "Proteases as antimalarial targets: strategies for genetic, chemical, and therapeutic validation". The FEBS Journal. 284 (16): 2604–2628. doi:10.1111/febs.14130. PMC 5575534. PMID 28599096.
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