Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C16H24N2O4.ClH |
| Molecular Weight | 344.834 |
| Optical Activity | ( - ) |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.CC(C)C[C@H](NC(=O)[C@@H](O)[C@H](N)CC1=CC=CC=C1)C(O)=O
InChI
InChIKey=XGDFITZJGKUSDK-UDYGKFQRSA-N
InChI=1S/C16H24N2O4.ClH/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);1H/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 |
|---|---|---|---|
Target ID: P09960 Gene ID: 4048.0 Gene Symbol: LTA4H Target Organism: Homo sapiens (Human) |
10.4 µM [IC50] | ||
Target ID: P28838 Gene ID: 51056.0 Gene Symbol: LAP3 Target Organism: Homo sapiens (Human) |
|||
Target ID: Q9H4A4 Gene ID: 6051.0 Gene Symbol: RNPEP Target Organism: Homo sapiens (Human) |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | BESTATIN Approved UseAdjunct to chemotherapy agent to extend survival and to maintain remission after treatment for acute non-lymphocytic leukemia in adults. Launch Date1987 |
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| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| [Effects of ubenimex ( bestatin) on the immunity of patients with squamous cell lung carcinoma treated with chemotherapy]. | 2001 Oct 20 |
|
| [A case of renal cell carcinoma with lymph node metastasis keeping remission for five years by adjuvant immunotherapy with ubenimex]. | 2003 Oct |
|
| Aminopeptidase N (APN)/CD13 inhibitor, Ubenimex, enhances radiation sensitivity in human cervical cancer. | 2008 Mar 19 |
|
| Idarubicin plus behenoyl cytarabine and 6-thioguanine compares favorably with idarubicin plus cytarabine-based regimen for children with previously untreated acute myeloid leukemia: 10-year retrospective, multicenter study in Korea. | 2010 Jan |
|
| The aminopeptidase inhibitor CHR-2863 is an orally bioavailable inhibitor of murine malaria. | 2012 Jun |
Patents
Sample Use Guides
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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DTXSID0045759
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11957481
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BY7Y2JX7NQ
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PARENT (SALT/SOLVATE)
SUBSTANCE RECORD
