Ubenimex

Ubenimex^[1]

IUPAC name (2S)-2-[[(2S,3R)-3-Amino-2-hydroxy-4-phenylbutanoyl]amino]-4-methylpentanoic acid
Other names Bestatin; N-[(2S,3R)-3-Amino-2-hydroxy-4-phenylbutyryl]-L-leucine
Identifiers
CAS number	58970-76-6, 65391-42-6 (HCl)
PubChem	72172
ChEMBL	CHEMBL29292^Y
Jmol-3D images	Image 1
SMILES CC(C)C[C@@H](C(=O)O)NC(=O)[C@H]([C@@H](CC1=CC=CC=C1)N)O
Properties
Molecular formula	C₁₆H₂₄N₂O₄
Molar mass	308.37 g mol⁻¹
Melting point	245 °C (dec.)
Hazards
S-phrases	S22 S24/25
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Ubenimex (INN), also known as bestatin, is a competitive protease inhibitor. It is an inhibitor of aminopeptidase B,^[2] leukotriene A4 hydrolase,^[3] aminopeptidase N.^[4] It is being studied for use in the treatment of acute myelocytic leukemia.^[5]

References

^ N-((2S,3R)-3-Amino-2-hydroxy-4-phenylbutyryl)-L-leucine at Sigma-Aldrich
^ Umezawa,H., Aoyagi,T., Suda,H., Hamada,M. & Takeuchi,T. (1976). Bestatin, an inhibitor of aminopeptidase B, produced by actinomycetes.. pp. 97–99.
^ 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.. pp. 131–137.
^ K Sekine, H Fujii and F Abe (1999). Induction of apoptosis by bestatin (ubenimex) in human leukemic cell lines. 13. pp. 729–734.
^ 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.