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|Section1={{Chembox Identifiers |Section1={{Chembox Identifiers
| CASNo= 58970-76-6 | CASNo= 58970-76-6
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 29292
| CASOther = <br>65391-42-6 (]) | CASOther = <br>65391-42-6 (])
| PubChem=72172 | PubChem=72172

Revision as of 15:04, 20 December 2010

Ubenimex
Names
IUPAC name (2S)-2-amino]-4-methylpentanoic acid
Other names Bestatin; N--L-leucine
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ECHA InfoCard 100.055.917 Edit this at Wikidata
PubChem CID
CompTox Dashboard (EPA)
SMILES
  • CC(C)C(C(=O)O)NC(=O)((CC1=CC=CC=C1)N)O
Properties
Chemical formula C16H24N2O4
Molar mass 308.378 g·mol
Melting point 245 °C (dec.)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Ubenimex (INN), also known as bestatin, is a competitive protease inhibitor. It is an inhibitor of aminopeptidase B, leukotriene A4 hydrolase , aminopeptidase N. It is being studied for use in the treatment of acute myelocytic leukemia.

Crystal structure of Bestatin.
Crystal structure of bestatin in the binding pocket of leukotriene A4 hydrolase. Rendered from PDB 1HS6.

References

  1. N-((2S,3R)-3-Amino-2-hydroxy-4-phenylbutyryl)-L-leucine at Sigma-Aldrich
  2. Umezawa,H., Aoyagi,T., Suda,H., Hamada,M. & Takeuchi,T. (1976). "Bestatin, an inhibitor of aminopeptidase B, produced by actinomycetes" (29): 97–99. {{cite journal}}: Cite journal requires |journal= (help)CS1 maint: multiple names: authors list (link)
  3. Muskardin,D.T., Voelkel,N.F. & Fitzpatrick,F.A. (1994). "Modulation of pulmonary leukotriene formation and perfusion pressure by bestatin, an inhibitor of leukotriene A4 hydrolase" (48): 131–137. {{cite journal}}: Cite journal requires |journal= (help)CS1 maint: multiple names: authors list (link)
  4. K Sekine, H Fujii and F Abe (1999). "Induction of apoptosis by bestatin (ubenimex) in human leukemic cell lines". 13 (5): 729–734. {{cite journal}}: Cite journal requires |journal= (help)
  5. Hirayama, Y; Sakamaki, S; Takayanagi, N; Tsuji, Y; Sagawa, T; Chiba, H; Matsunaga, T; Niitsu, Y (2003). "Chemotherapy with ubenimex corresponding to patient age and organ disorder for 18 cases of acute myelogeneous leukemia in elderly patients--effects, complications and long-term survival". Gan to kagaku ryoho. Cancer & chemotherapy. 30 (8): 1113–8. PMID 12938265.


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External Links

  • The MEROPS online database for peptidases and their inhibitors: Bestatin
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