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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
Structure of UBENIMEX

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

HIDE SMILES / InChI

Description

Ubenimex is a dipeptide, which specificallyinhibits 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 TargetPharmacologyConditionPotency
10.4 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
BESTATIN
Primary
Unknown
Primary
Unknown

Cmax

ValueDoseCo-administeredAnalytePopulation
7.1 μg/mL
150 mg 2 times / day multiple, oral
UBENIMEX plasma
Homo sapiens
2416.83 μg/L
30 mg single, oral
UBENIMEX plasma
Homo sapiens
2.213 μg/mL
30 mg single, oral
UBENIMEX serum
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
3957.04 μg × h/L
30 mg single, oral
UBENIMEX plasma
Homo sapiens
5.211 μg × h/mL
30 mg single, oral
UBENIMEX serum
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
2.1 h
150 mg 2 times / day multiple, oral
UBENIMEX plasma
Homo sapiens
3.49 h
30 mg single, oral
UBENIMEX plasma
Homo sapiens
5.74 h
30 mg single, oral
UBENIMEX serum
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
88.35%
UBENIMEX serum
Homo sapiens

Doses

PubMed

Sample Use Guides

In Vivo Use Guide
Administer 30 mg ubenimex orally once a day.
Route of Administration: Oral
In Vitro Use Guide
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.