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
Molecular Formula | C16H24N2O4 |
Molecular Weight | 308.3728 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
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) 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 |
|||
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 |
---|---|---|---|---|
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 |
|||
Primary | Unknown Approved UseUnknown |
|||
Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
---|---|---|
Cryptosporidium parvum metalloaminopeptidase inhibitors prevent in vitro excystation. | 1996 Dec |
|
Bestatin-mediated inhibition of leucine aminopeptidase may hinder HIV infection. | 1997 Dec |
|
Adult T-cell leukemia associated with gastric carcinoma: report of a case. | 2001 |
|
[Effects of ubenimex ( bestatin) on the immunity of patients with squamous cell lung carcinoma treated with chemotherapy]. | 2001 Oct 20 |
|
Possible involvement of placental peptidases that degrade gonadotropin-releasing hormone (GnRH) in the dynamic pattern of placental hCG secretion via GnRH degradation. | 2002 Jul |
|
[Experimental study of the enhancement effect of aminopeptidase N inhibitor ubenimex on the differentiation induction activity of all-trans-retinoic acid in acute promyelocytic leukemia cells and its mechanism]. | 2006 Jul |
|
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 |
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.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 18:38:42 UTC 2023
by
admin
on
Fri Dec 15 18:38:42 UTC 2023
|
Record UNII |
I0J33N5627
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Code | English | ||
|
Systematic Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English |
Classification Tree | Code System | Code | ||
---|---|---|---|---|
|
EU-Orphan Drug |
EU/3/16/1638
Created by
admin on Fri Dec 15 18:38:42 UTC 2023 , Edited by admin on Fri Dec 15 18:38:42 UTC 2023
|
||
|
FDA ORPHAN DRUG |
749020
Created by
admin on Fri Dec 15 18:38:42 UTC 2023 , Edited by admin on Fri Dec 15 18:38:42 UTC 2023
|
||
|
FDA ORPHAN DRUG |
806720
Created by
admin on Fri Dec 15 18:38:42 UTC 2023 , Edited by admin on Fri Dec 15 18:38:42 UTC 2023
|
||
|
FDA ORPHAN DRUG |
755720
Created by
admin on Fri Dec 15 18:38:42 UTC 2023 , Edited by admin on Fri Dec 15 18:38:42 UTC 2023
|
||
|
FDA ORPHAN DRUG |
498115
Created by
admin on Fri Dec 15 18:38:42 UTC 2023 , Edited by admin on Fri Dec 15 18:38:42 UTC 2023
|
||
|
NCI_THESAURUS |
C2139
Created by
admin on Fri Dec 15 18:38:42 UTC 2023 , Edited by admin on Fri Dec 15 18:38:42 UTC 2023
|
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
I0J33N5627
Created by
admin on Fri Dec 15 18:38:42 UTC 2023 , Edited by admin on Fri Dec 15 18:38:42 UTC 2023
|
PRIMARY | |||
|
100000076638
Created by
admin on Fri Dec 15 18:38:42 UTC 2023 , Edited by admin on Fri Dec 15 18:38:42 UTC 2023
|
PRIMARY | |||
|
2787
Created by
admin on Fri Dec 15 18:38:42 UTC 2023 , Edited by admin on Fri Dec 15 18:38:42 UTC 2023
|
PRIMARY | |||
|
265489
Created by
admin on Fri Dec 15 18:38:42 UTC 2023 , Edited by admin on Fri Dec 15 18:38:42 UTC 2023
|
PRIMARY | |||
|
C1015
Created by
admin on Fri Dec 15 18:38:42 UTC 2023 , Edited by admin on Fri Dec 15 18:38:42 UTC 2023
|
PRIMARY | |||
|
C012211
Created by
admin on Fri Dec 15 18:38:42 UTC 2023 , Edited by admin on Fri Dec 15 18:38:42 UTC 2023
|
PRIMARY | |||
|
5940
Created by
admin on Fri Dec 15 18:38:42 UTC 2023 , Edited by admin on Fri Dec 15 18:38:42 UTC 2023
|
PRIMARY | |||
|
261-529-2
Created by
admin on Fri Dec 15 18:38:42 UTC 2023 , Edited by admin on Fri Dec 15 18:38:42 UTC 2023
|
PRIMARY | |||
|
Ubenimex
Created by
admin on Fri Dec 15 18:38:42 UTC 2023 , Edited by admin on Fri Dec 15 18:38:42 UTC 2023
|
PRIMARY | |||
|
58970-76-6
Created by
admin on Fri Dec 15 18:38:42 UTC 2023 , Edited by admin on Fri Dec 15 18:38:42 UTC 2023
|
PRIMARY | |||
|
SUB11372MIG
Created by
admin on Fri Dec 15 18:38:42 UTC 2023 , Edited by admin on Fri Dec 15 18:38:42 UTC 2023
|
PRIMARY | |||
|
DB03424
Created by
admin on Fri Dec 15 18:38:42 UTC 2023 , Edited by admin on Fri Dec 15 18:38:42 UTC 2023
|
PRIMARY | |||
|
CHEMBL29292
Created by
admin on Fri Dec 15 18:38:42 UTC 2023 , Edited by admin on Fri Dec 15 18:38:42 UTC 2023
|
PRIMARY | |||
|
m11294
Created by
admin on Fri Dec 15 18:38:42 UTC 2023 , Edited by admin on Fri Dec 15 18:38:42 UTC 2023
|
PRIMARY | Merck Index | ||
|
72172
Created by
admin on Fri Dec 15 18:38:42 UTC 2023 , Edited by admin on Fri Dec 15 18:38:42 UTC 2023
|
PRIMARY | |||
|
DTXSID4048430
Created by
admin on Fri Dec 15 18:38:42 UTC 2023 , Edited by admin on Fri Dec 15 18:38:42 UTC 2023
|
PRIMARY |
Related Record | Type | Details | ||
---|---|---|---|---|
|
SALT/SOLVATE -> PARENT |
|
Related Record | Type | Details | ||
---|---|---|---|---|
|
ACTIVE MOIETY |