Bestatin
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Bestatin
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CAS No:
58970-76-6
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Formula:
C16H24N2O4
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Chemical Name:
Bestatin
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Synonyms:
L-Leucine,N-[(2S,3R)-3-amino-2-hydroxy-1-oxo-4-phenylbutyl]-;L-Leucine,N-(3-amino-2-hydroxy-1-oxo-4-phenylbutyl)-,[S-(R*,S*)]-;N-[(2S,3R)-3-Amino-2-hydroxy-1-oxo-4-phenylbutyl]-L-leucine;Bestatin;NK 421;Ubenimex;(-)-Bestatin;NSC 265489;339186-55-9
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CAS No:
Description
Bestatin is a natural, broad-spectrum, and competitive aminopeptidase inhibitor.
Ubenimex (also known as bestatin) is a competitive protease inhibitor. It is an inhibitor of aminopeptidase B, leukotriene A4 hydrolase, aminopeptidase N. It is being studied for use in the treatment of acute myelocytic leukemia.|Ubenimex is a microbial metabolite and dipeptide with potential immunomodulatory and antitumor activities. Ubenimex competitively inhibits many aminopeptidases, including B, N and leucine aminopeptidases. Aminopeptidases has been implicated in the process of cell adhesion and invasion of tumor cells. Therefore, inhibiting aminopeptidases may partially attribute to the antitumor effect of ubenimex. This agent also activates T lymphocyte, macrophage and bone marrow stem cell as well as stimulates release of interleukin-1 and -2, thus further enhances its antitumor activity.
Characteristics
112.65000
1.62400
White crystalline powder
1.197 g/cm3
234.5 °C
604.7ºC at 760 mmHg
319.5ºC
1.557
Soluble in water (<1 25), DMSO (2 mg/ml), methanol (5 mg/ml), 1eq. NaOH (50 mM), ethanol (<1 mg/ml at 25°C), acetic acid, aq. HCl, and alkaline solution. Insoluble in ethyl acetate, benzene, hexane, and chloroform.
2-8ºC
LD50 in male, female mice, male, female rats (g/kg): 1.3, 1.9, 1.9, 2.1 s.c.; 0.19, 0.19, 0.90, 0.78 i.p.; >4.0, >4.0, >2.0, >2.0 orally (Sakakibara)
Safety Information
NONH for all modes of transport
3
S24/25
OH2915000
Stable at normal temperatures and pressures.
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
H315
|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 2 companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Drug Information
An adjuvant therapy used for acute and chronic myelonous leukemia, lung cancer and nasopharyngeal cancer. It is also used to treat hypercholesterolaemia.
Compounds which inhibit or antagonize biosynthesis or actions of proteases (ENDOPEPTIDASES). (See all compounds classified as Protease Inhibitors.)|Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)|Substances that augment, stimulate, activate, potentiate, or modulate the immune response at either the cellular or humoral level. The classical agents (Freund's adjuvant, BCG, Corynebacterium parvum, et al.) contain bacterial antigens. Some are endogenous (e.g., histamine, interferon, transfer factor, tuftsin, interleukin-1). Their mode of action is either non-specific, resulting in increased immune responsiveness to a wide variety of antigens, or antigen-specific, i.e., affecting a restricted type of immune response to a narrow group of antigens. The therapeutic efficacy of many biological response modifiers is related to their antigen-specific immunoadjuvanticity. (See all compounds classified as Adjuvants, Immunologic.)|Agents used to treat AIDS and/or stop the spread of the HIV infection. These do not include drugs used to treat symptoms or opportunistic infections associated with AIDS. (See all compounds classified as Anti-HIV Agents.)|Chemical substances, produced by microorganisms, inhibiting or preventing the proliferation of neoplasms. (See all compounds classified as Antibiotics, Antineoplastic.)|Biologically active substances whose activities affect or play a role in the functioning of the immune system. (See all compounds classified as Immunologic Factors.)
(3-amino-2-hydroxy-4-phenylbutanoyl)-L-leucine
Bestatin Use and Manufacturing
An aminopeptidase inhibitor used in combination with chemotherapeutics for the maintenance and enhancement of complete remission of acute non-lymphocytic leukemia in adults.
Human drugs -> Rare disease (orphan)
Computed Properties
Molecular Weight:308.37
XLogP3:-1
Hydrogen Bond Donor Count:4
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:8
Exact Mass:308.17360725
Monoisotopic Mass:308.17360725
Topological Polar Surface Area:113
Heavy Atom Count:22
Complexity:367
Defined Atom Stereocenter Count:3
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
Drug Function and Efficacy
Extract from the above information
Registered Holders
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NIPPON KAYAKU CO.LTD.
Active
Brazil
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Zhejiang Apeloa Kangyu Pharmaceutical Co., Ltd.
Active
China
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Xi'an Wan Long Pharmaceutical Co., Ltd.
Active
China
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