Structure via PubChem · Public domain (PubChem)
ubenimex
Sign in to saveAlso known as (2S)-Bestatin, bestatin
Ubenimex (INN), also known more commonly as bestatin, is a competitive, reversible protease inhibitor. It is an inhibitor of arginyl aminopeptidase (aminopeptidase B), leukotriene A4 hydrolase (a zinc metalloprotease that displays both epoxide hydrolase and aminopeptidase activities), alanyl aminopeptidase (aminopeptidase M/N), leucyl/cystinyl aminopeptidase (oxytocinase/vasopressinase), and membrane dipeptidase (leukotriene D4 hydrolase). It is being studied for use in the treatment of acute myelocytic leukemia and lymphedema. It is derived from Streptomyces olivoreticuli. Ubenimex has been f
Chemical data
- Formula
- C16H24N2O4
- Molecular weight
- 308.37 g/mol
- IUPAC name
- (2S)-2-[[(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoyl]amino]-4-methylpentanoic acid
- SMILES
- CC(C)C[C@@H](C(=O)O)NC(=O)[C@H]([C@@H](CC1=CC=CC=C1)N)O
- InChIKey
- VGGGPCQERPFHOB-RDBSUJKOSA-N
- XLogP
- -1
- Polar surface area
- 113 Ų
- H-bond donors
- 4
- H-bond acceptors
- 5
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 2
- Molecule type
- Small molecule
- Indications
- pulmonary arterial hypertension, lymphedema
via ChEMBL · EBI
Research
885 papers- Efficacy of Standardised Treatments Combined with Ubenimex in Patients with Malignant Tumors.Journal of the College of Physicians and Surgeons--Pakistan : JCPSP · 2021
- Review of ubenimex (Bestatin): clinical research.Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie · 1991
- Ubenimex inhibits cell proliferation, migration and invasion in renal cell carcinoma: the effect is autophagy-associated.Oncology reports · 2015
- Ubenimex induces apoptotic and autophagic cell death in rat GH3 and MMQ cells through the ROS/ERK pathway.Drug design, development and therapy · 2019
- Ubenimex induces autophagy inhibition and EMT suppression to overcome cisplatin resistance in GC cells by perturbing the CD13/EMP3/PI3K/AKT/NF-κB axis.Aging · 2019
via PubMed
Wikidata facts
- Mass
- 308.174
Show 5 more facts
- chemical formula
- C₁₆H₂₄N₂O₄
- canonical SMILES
- CC(C)CC(C(=O)O)NC(=O)C(C(CC1=CC=CC=C1)N)O
- subject has role
- immunologic adjuvant
- isomeric SMILES
- CC(C)C[C@@H](C(=O)O)NC(=O)[C@H]([C@@H](CC1=CC=CC=C1)N)O
- Commons category
- Ubenimex
via Wikidata · CC0
~1 min read
Encyclopedic overview
3 sectionsContents
- See also
- References
- External links
Ubenimex (INN), also known more commonly as bestatin, is a competitive, reversible protease inhibitor. It is an inhibitor of arginyl aminopeptidase (aminopeptidase B), leukotriene A4 hydrolase (a zinc metalloprotease that displays both epoxide hydrolase and aminopeptidase activities), alanyl aminopeptidase (aminopeptidase M/N), leucyl/cystinyl aminopeptidase (oxytocinase/vasopressinase), and membrane dipeptidase (leukotriene D4 hydrolase). It is being studied for use in the treatment of acute myelocytic leukemia and lymphedema. It is derived from Streptomyces olivoreticuli. Ubenimex has been found to inhibit the enzymatic degradation of oxytocin, vasopressin, enkephalins, and various other peptides and compounds.
[[Image:Bestatin.jpg|thumb|350px|left|upright=2.0|class=skin-invert-image|alt=Crystal structure of ubenimex|Crystal structure of ubenimex in the binding pocket of leukotriene A4 hydrolase. Rendered from PDB 1HS6.]]
Excerpted from Wikipedia’s “ubenimex” article, available under the CC BY-SA 4.0 licence.