Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C16H24N2O4 |
Molecular Weight | 308.3728 |
Optical Activity | ( - ) |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(C)C[C@H](NC(=O)[C@@H](O)[C@H](N)CC1=CC=CC=C1)C(O)=O
InChI
InChIKey=VGGGPCQERPFHOB-RDBSUJKOSA-N
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
Ubenimex is a dipeptide, which specifically
inhibits the activity of leukotriene A4 hydrolase, aminopeptidase B and leucine aminopeptidase of the cell membrane. The drug was isolated from Streptomyces oliooreticuli in 1976 in Nippon Kayaku, Japan and approved for the treatment of acute non-lymphocytic leukemia under the name Bestatin. In the USA the drug is currentlu in Phase II for the treatment of pulmonary arterial hypertension and lymphedema.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: P09960 Gene ID: 4048.0 Gene Symbol: LTA4H Target Organism: Homo sapiens (Human) Sources: http://www.eigerbio.com/resources/PR-15Dec2015.pdf |
10.4 µM [IC50] | ||
Target ID: P28838 Gene ID: 51056.0 Gene Symbol: LAP3 Target Organism: Homo sapiens (Human) Sources: http://www.eigerbio.com/resources/PR-15Dec2015.pdf |
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Target ID: Q9H4A4 Gene ID: 6051.0 Gene Symbol: RNPEP Target Organism: Homo sapiens (Human) Sources: http://www.eigerbio.com/resources/PR-15Dec2015.pdf |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | BESTATIN Approved UseAdjunct to chemotherapy agent to extend survival and to maintain remission after treatment for acute non-lymphocytic leukemia in adults. Launch Date5.36457609E11 |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Cryptosporidium parvum metalloaminopeptidase inhibitors prevent in vitro excystation. | 1996 Dec |
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Bestatin-mediated inhibition of leucine aminopeptidase may hinder HIV infection. | 1997 Dec |
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In vitro and in vivo evaluation of aminopeptidase inhibitors as antimicrosporidial therapies. | 2001 |
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Adult T-cell leukemia associated with gastric carcinoma: report of a case. | 2001 |
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Possible involvement of placental peptidases that degrade gonadotropin-releasing hormone (GnRH) in the dynamic pattern of placental hCG secretion via GnRH degradation. | 2002 Jul |
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Induction of graft-versus-host disease and a graft-versus-leukemia effect using ubenimex in a patient with infantile leukemia relapsing after an unrelated cord blood transplant. | 2002 Oct |
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Aminopeptidase inhibitors inhibit proliferation and induce apoptosis of K562 and STI571-resistant K562 cell lines through the MAPK and GSK-3beta pathways. | 2003 Nov |
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[A case of renal cell carcinoma with lymph node metastasis keeping remission for five years by adjuvant immunotherapy with ubenimex]. | 2003 Oct |
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CD13/Aminopeptidase N overexpression by basic fibroblast growth factor mediates enhanced invasiveness of 1F6 human melanoma cells. | 2006 Jun 5 |
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Complete remission induced by gemtuzumab ozogamicin in a Jehovah's Witness patient with acute myelogenous leukemia. | 2007 Jun |
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The aminopeptidase inhibitor CHR-2863 is an orally bioavailable inhibitor of murine malaria. | 2012 Jun |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8347731
Administer 30 mg ubenimex orally once a day.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2223152
MT-1, MOLT-4, HL-60, K562 and Raji cells were cultured in the presence of ubenimex (4.5, 45, 450 ug/ml and 4.5 mg/ml) at 37C. The number of viable HL-60 cells decreased with time at a high concentration of the drug (4.5 mg/ml) with time. The number of viable MT-1 cells was also decreased at the concentrations 4.5 mg/ml and 450 ug/ml. The number of viable MOLT-4 cells did not decrease even at high concentrations. The number of viable Raji cells also decreased at 4.5 mg/ml, but was not affected at 450 ug/ml.
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Classification Tree | Code System | Code | ||
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EU-Orphan Drug |
EU/3/16/1638
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FDA ORPHAN DRUG |
749020
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FDA ORPHAN DRUG |
806720
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FDA ORPHAN DRUG |
755720
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FDA ORPHAN DRUG |
498115
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NCI_THESAURUS |
C2139
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100000076638
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Ubenimex
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m11294
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DTXSID4048430
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)