Ubenimex

"Bestatin" redirects here. For other uses, see Bestatin (disambiguation).

Ubenimex (INN), also known more commonly as bestatin, is a competitive, reversible protease inhibitor. It is an inhibitor of arginyl aminopeptidase (aminopeptidase B),^[3] leukotriene A₄ hydrolase (a zinc metalloprotease that displays both epoxide hydrolase and aminopeptidase activities),^[4] alanyl aminopeptidase (aminopeptidase M/N),^[5] leucyl/cystinyl aminopeptidase (oxytocinase/vasopressinase),^[6][7] and membrane dipeptidase (leukotriene D₄ hydrolase). It is being studied for use in the treatment of acute myelocytic leukemia^[8] and lymphedema.^[9] It is derived from Streptomyces olivoreticuli.^[10] Ubenimex has been found to inhibit the enzymatic degradation of oxytocin, vasopressin, enkephalins, and various other peptides and compounds.^{[citation needed]}

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

Ubenimex^[1]

Names
IUPAC name N-[(2S,3R)-3-Amino-2-hydroxy-4-phenylbutanoyl]-L-leucine
Systematic IUPAC name (2S)-2-[(2S,3R)-3-Amino-2-hydroxy-4-phenylbutanamido]-4-methylpentanoic acid
Other names Bestatin; N-[(2S,3R)-3-Amino-2-hydroxy-4-phenylbutyryl]-L-leucine
Identifiers
CAS Number	58970-76-6 Y 65391-42-6 (HCl)
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL29292 Y
ChemSpider	65145
DrugBank	DB03424
ECHA InfoCard	100.055.917
EC Number	261-529-2
KEGG	D00087
PubChem CID	72172
UNII	I0J33N5627 Y
CompTox Dashboard (EPA)	DTXSID4048430
InChI InChI=1S/C16H24N2O4/c1-10(2)8-13(16(21)22)18-15(20)14(19)12(17)9-11-6-4-3-5-7-11/h3-7,10,12-14,19H,8-9,17H2,1-2H3,(H,18,20)(H,21,22)/t12-,13+,14+/m1/s1 Key: VGGGPCQERPFHOB-RDBSUJKOSA-N
SMILES CC(C)C[C@@H](C(=O)O)NC(=O)[C@H]([C@@H](CC1=CC=CC=C1)N)O
Properties
Chemical formula	C16H24N2O4
Molar mass	308.378 g·mol−1
Melting point	245 °C (473 °F; 518 K) (decomposes)
Hazards
GHS labelling:[2]
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is YN ?) Infobox references

See also

• Amastatin
• Pepstatin