Bestatin | 58970-76-6

Bestatin Properties

Melting point	245 °C (dec.)(lit.)
alpha	D20 -15.5° (c = 1.0 in 1N HCl)
Boiling point	448.76°C (rough estimate)
Density	1.0917 (rough estimate)
refractive index	1.5800 (estimate)
storage temp.	Keep in dark place,Sealed in dry,Room Temperature
solubility	Aqueous Acid (Slightly, Sonicated), DMSO (Slightly, Heated)
form	Powder
pka	8.1, 3.1(at 25℃)
color	White
optical activity	[α]20/D 11°, c = 1 in 1 M NaOH
Water Solubility	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.
Merck	13,9910
Major Application	peptide synthesis
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
InChIKey	VGGGPCQERPFHOB-RDBSUJKOSA-N
SMILES	CC(C)C[C@H](NC(=O)[C@@H](O)[C@H](N)Cc1ccccc1)C(O)=O
CAS DataBase Reference	58970-76-6(CAS DataBase Reference)
FDA UNII	I0J33N5627
UNSPSC Code	12352209
NACRES	NA.77

SAFETY

Risk and Safety Statements

Symbol(GHS)

GHS07

Signal word

Warning

Hazard statements

H315-H319-H335

Precautionary statements

P264b-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P362+P364-P403+P233-P501c

PPE

Eyeshields, Gloves, type N95 (US)

Safety Statements

22-24/25

WGK Germany

3

RTECS

OH2915000

HS Code

29242998

Storage Class

11 - Combustible Solids

Toxicity

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)

NFPA 704

	0
2		0

Bestatin price More Price(98)

Manufacturer	Product number	Product description	CAS number	Packaging	Price	Updated	Buy
Sigma-Aldrich	200484-M	Bestatin Binds to cell surfaces and inhibits surface aminopeptidases, notably aminopeptidase B and leucine aminopeptidase.	58970-76-6	10 mg	$215	2026-04-30	Buy
Sigma-Aldrich	200484-M	Bestatin Binds to cell surfaces and inhibits surface aminopeptidases, notably aminopeptidase B and leucine aminopeptidase.	58970-76-6	500 mg	$11330	2026-04-30	Buy
Sigma-Aldrich	482609	N-[(2S,3R)-3-Amino-2-hydroxy-4-phenylbutyryl]-L-leucine 97%	58970-76-6	500mg	$357	2026-04-30	Buy
Sigma-Aldrich	200484-M	Bestatin Binds to cell surfaces and inhibits surface aminopeptidases, notably aminopeptidase B and leucine aminopeptidase.	58970-76-6	250 mg	$20650	2026-04-30	Buy
Sigma-Aldrich	200484-M	Bestatin Binds to cell surfaces and inhibits surface aminopeptidases, notably aminopeptidase B and leucine aminopeptidase.	58970-76-6	200 mg	$20650	2026-04-30	Buy

Product number	Packaging	Price	Buy
200484-M	10 mg	$215	Buy
200484-M	500 mg	$11330	Buy
482609	500mg	$357	Buy
200484-M	250 mg	$20650	Buy
200484-M	200 mg	$20650	Buy

Bestatin Chemical Properties,Uses,Production

Description

Bestatin is an aminopeptidase inhibitor originally isolated from S. olivoreticuli. It inhibits aminopeptidase B (IC₅₀ = 0.05 μg/ml), aminopeptidase N (IC₅₀ = 16.9 μM), leucine aminopeptidase (IC₅₀ = 0.01 μg/ml), and the aminopeptidase activity of leukotriene A₄ (LTA₄) hydrolase (K_app = 172 nM). It is selective for these aminopeptidases over aminopeptidase A, trypsin, chymotrypsin, elastase, papain, pepsin, and thermolysin. Bestatin inhibits the production of LTB₄ in erythrocytes when used at a concentration of 70 μM. It increases the expression of Akt, inhibits proliferation, migration, and invasion, and induces autophagy and apoptosis in 5637 bladder cancer cells. Bestatin (5 and 15 mg/kg) decreases serum levels of LTB₄ and reduces tumor growth in a patient-derived xenograft (PDX) mouse model of colorectal cancer.

Chemical Properties

white powder, soluble in methanol, ethanol, DMSO and other organic solvents, from Streptomyces olivoreticuli.

Originator

Inst. of Microbial Chem (Japan)

Uses

Ubenimex (also known as bestatin) is a competitive aminopeptidase B inhibitor with an IC50 of 100 mg/ml for K562 cells. Proliferation of all the cell lines except KG1 was inhibited by bestatin. P39/TSU, HL60 and U937 were highly sensitive, with 50% growth inhibitory concentration. It is useful in the treatment of non-lymphocytic leukemia. In other types of cancers ubenimex added to radiotherapy or chemotherapy following surgery significantly inmases survival time through immunopotentiation. It is being studied for use in the treatment of acute myelocytic leukemia.

Uses

Bestatin is "pseudo"-dipeptide isolated from Strepotmyces olivreticuli in 1976. Bestatin is a potent aminopeptidase B inhibitor with no carboxypeptidase activity. Bestatin acts as an immunomodulator by activating macrophages and T lymphocytes. Bestatin also exhibits good antitumour activity and is has been investigated in clinical trials.

Application

Bestatin can indirectly act on monocytes by inhibiting Aminopeptidase B, which in turn inhibits the catabolism of tuftsin. Bestatin has also been shown to inhibit Leukotriene A4 hydrolase. It can directly stimulate lymphocytes through its fixation on the cell surface. The agent has been used in multiple leukemia studies. Bestatin is an aminopeptidase inhibitor, inhibits enkephalin metabolism and leukotriene A4 hydrolase. Inhibits tumor cell proliferation.

brand name

Bestatin

General Description

Bestatin was found in the culture broth of Streptomyces olivoreticuli in 1976by Umezawa et al. in the course of screening specific enzyme inhibitors of microbial origin. It shows inhibitory activity against specific exopeptidases, e.g., aminopeptidase B and leucine aminopeptidase. However, it does not act against aminopeptidase A, carboxypeptidases A and B, or endopeptidases. Bestatin acts as a bioresponse modifier and shows antitumor activity via stimulation of immuno response in the host. In combination with cytotoxic anticancer drugs, it is now under clinical evaluation for use in cancer therapy.

reaction suitability

reaction type: solution phase peptide synthesis

Biological Activity

Aminopeptidase inhibitor (K i = 0.001-90 mM); inhibits enkephalin metabolism and leukotriene A 4 hydrolase. Inhibits tumor cell proliferation.

Safety Profile

Poison by intraperitoneal route.Moderately toxic by subcutaneous route. Experimentalreproductive effects. When heated to decomposition itemits toxic fumes of NOx.

storage

Store at +4°C

Clinical claims and research

Bestatin (ubenimex) is a potent inhibitor of aminopeptidase N and aminopeptidase B, which was isolated from a culture filtrate of Streptomyces olivoreticuli during the search for specific inhibitors of enzymes present on the membrane of eukaryotic cells. Inhibitors of aminopeptidase activity are associated with macrophage activation and differentiation, and Bestatin has shown significant therapeutic effects in several clinical trials. In one multi-institutional study, patients with acute non-lymphocytic leukemia (ANLL) were randomized to receive either Bestatin or control orally after completion of induction and consolidation therapy, and concomitant with maintenance chemotherapy. Remission duration was prolonged in the Bestatin group, although this difference did not reach statistical significance. However, OS was prolonged in the Bestatin group. Recently, a confirmatory phase III trial in ANLL was reported that extended the observation to a significant prolongation of remission. Bestatin has also shown adjuvant activity when administered to acute leukemia and CML patients who did not develop graft-versus-host disease (GVHD) within 30 days following BMT. Bestatin-treated acute leukemia patients had an increased incidence of chronic low-grade GVHD compared with the control arm and a lower relapse rate. Recently, a phase III study of resected stage 1 squamous cell lung cancer patients treated orally with either Bestatin or placebo daily for 2 years revealed that 5-year cancer-free survival was significantly greater in the Bestatin group (71%) as compared to the placebo group (62%). OS was also significantly improved, as was cancer-free survival. Recent studies in patients with nonsmall cell lung cancer (NSCLCs) suggest that it also has anti-angiogenic activity.

Mode of action

Bestatin acts as an immunomodulator by activating macrophages and T lymphocytes.

References

1. umezawa h, aoyagi t, suda h, hamada m, takeuchi t, bestatin, an inhibitor of aminopeptidase b, produced by actinomycetes, j antibiot (tokyo). 1976 jan; 29(1):97-9.2. umezawa, h., aoyagi, t., suda, h., hamada, m., and takeuchi, t. 197615. antibiotics 29, 97.3. suda, h., takita, t., aoyagi, t., and umezawa, h. (1976) j. antibiotics 29, 100.4. nakamura, h., suda, h., takita, t., aoyagi, t., umezawa, h., and iitaka, y. (1976) j. antibiotics 29, 102.5. umezawa, s., tsuchiya, t., and tatsuta, k. (1966) bull. chem. sot. japan 39, 1235. 6. barlow, c. b., and gijthrie, r. d. (1967) j. chem. sot. (c) 1194. 7. bukhari, s. t. k., guthrie, r. d., scott, a. i., and wrixon, a. d. (1970) tetrahedron 26, 3653.8. suda et al. inhibition of aminopeptidase b and leucine aminopeptidase by bestatin and its stereoisomer, archives of biochemistry and biophysics, 77, 196-200 (1976)

Bestatin synthesis

Synthesis of Bestatin from (2S,3R)-3-(((Benzyloxy)carbonyl)aMino)-2-hydroxy-4-phenylbutanoic acid

Bestatin Preparation Products And Raw materials

Raw materials

(2S,3R)-3-(((Benzyloxy)carbonyl)aMino)-2-hydroxy-4-phenylbutanoic acid

Preparation Products

Bestatin Suppliers

Global( 477)Suppliers

Supplier	Tel	Email	Country	ProdList	Advantage
Chengdu Hepu Pharmaceutical Technology Co. , Ltd	028-68075191 13981809616	2041948498@qq.com	China	9	58
AF Biochem Co., Ltd.	+86-028-60911900 13540204019	sales@afbiochem.com	China	479	57
Zhangshu Hongyuan Biomedical Technology Co., Ltd.	19195036662	335864138@qq.com	China	159	58
J & K SCIENTIFIC LTD.	18210857532 18210857532	jkinfo@jkchemical.com	China	96815	76
Meryer (Shanghai) Chemical Technology Co., Ltd.	4006356688 18621169109	market03@meryer.com	China	40202	62
3B Pharmachem (Wuhan) International Co.,Ltd.	18930552037	3bsc@sina.com	China	15813	69
Chembest Research Laboratories Limited	021-20908456	sales@BioChemBest.com	China	5996	61
Beijing HwrkChemical Technology Co., Ltd	89508211 18501085097	sales.bj@hwrkchemical.com	China	9407	55
Energy Chemical	400-0056266	sales8178@energy-chemical.com	China	44850	61
Adamas Reagent, Ltd.	400-6009262 15618770481	yhx@titansci.com	China	14098	59

Supplier	Advantage
Chengdu Hepu Pharmaceutical Technology Co. , Ltd	58
AF Biochem Co., Ltd.	57
Zhangshu Hongyuan Biomedical Technology Co., Ltd.	58
J & K SCIENTIFIC LTD.	76
Meryer (Shanghai) Chemical Technology Co., Ltd.	62
3B Pharmachem (Wuhan) International Co.,Ltd.	69
Chembest Research Laboratories Limited	61
Beijing HwrkChemical Technology Co., Ltd	55
Energy Chemical	61
Adamas Reagent, Ltd.	59

View Lastest Price from Bestatin manufacturers

Update time	Product	Price	Min. Order	Purity	Supply Ability	Manufacturer
2026-07-15	Bestatin 58970-76-6	$46.00-79.00		99.54%	10g	TargetMol Chemicals Inc.
2026-07-15	Bestatin 58970-76-6	$46.00-79.00		99.54%	10g	TargetMol Chemicals Inc.
2025-06-20	Ubenimex 58970-76-6		1kg	0.99	500kg	Hebei Yanxi Chemical Co., Ltd.

Bestatin
58970-76-6
$46.00-79.00
99.54%
TargetMol Chemicals Inc.

Bestatin
58970-76-6
$46.00-79.00
99.54%
TargetMol Chemicals Inc.

Ubenimex
58970-76-6
$0.00
0.99
Hebei Yanxi Chemical Co., Ltd.

Bestatin Spectrum

Bestatin(58970-76-6)¹HNMR Bestatin(58970-76-6)IR

58970-76-6(Bestatin)Related Search:

Aminoethoxyvinyl glycine hydrochloride Glycine L-tert-Leucine Tris(hydroxymethyl)aminomethane 6-Aminocaproic acid

mecysteine Chlorophosphonazo III N-Carbobenzoxy-DL-leucine Bestatin hydrochloride N-(2-Hydroxyethyl)lactamide

H-beta-Ala-Leu-OH H-beta-Ala-Ala-OH threo-(2RS)-3-Acetylamino-2-hydroxy-4-oxo-4-phenylbutyric acid (-)-N-[(2S, 3R)-3-Amino-2-hydroxy-4-phenylbutyryl]-L-leucine methyl ester Amino acids

Bestatin H-beta-Ala-DL-Leu-OH Ubenimex,AntitumorDrug

1of4

UbenaMix, Inobestin, NK 421 L-Leucine,N-[(2S,3R)-3-aMino-2-hydroxy-1-oxo-4-phenylbutyl]- N-[(2S,3R)-3-AMino-2-hydroxy-4-phenylbutyryl]-L-leucine 97% 3-(r)-amino-2-(s)-hydroxy-4-phenylbutanoyl-(s)-leucine n-(3-amino-2-hydroxy-1-oxo-4-phenylbutyl)-,(s-(r*,s*))-l-leucin nk421 Bestatin - CAS 58970-76-6 - Calbiochem Bestatin free base Bestatin-d5 (Ubenimex-d5) N-[(2S,3R)-3-AMINO-2-HYDROXY-1-OXO-4-PHENYLBUTYL]-L-LEUCINE N-((2S,3R)-3-AMINO-2-HYDROXY-4-PHENYLBUTYRYL)-L-LEUCINE [(2S,3R)-3-AMINO-2-HYDROXY-4-PHENYLBUTYRYL]-L-LEUCINE [(2S,3R)-3-AMINO-2-HYDROXY-4-PHENYLBUTANOYL]-LEU [(2S,3R)-3-AMINO-2-HYDROXY-4-PHENYLBUTANOYL]-LEU-OH [(2S, 3R)-3-AMINO-2-HYDROXY-4-PHENYLBUTANOYL]-L-LEUCINE BESTATIN BENIMEX L-Leucine, N-(3-amino-2-hydroxy-1-oxo-4-phenylbutyl)-, [S-(R*,S*)]- L-Leucine, N-[(2S,3R)-3-amino-2-hydroxy-1-oxo-4-phenylbutyl]- (9CI) NSC 265489 [S-(R*,S*)]-N-(3-Amino-2-hydroxy-1-oxo-4-phenylbuty1)-L-leucine [S-(R*,S*)]-N-(3-amino-2-hydroxy-4-phenylbutyroyl)-L-leucine N-[(2S,3R)-3-Amino-2-hydroxy-4-phenylbutanoyl]-L-leucine N-[(2S,3R)-3-Amino-2-hydroxy-4-phenylbutyryl]-L-leucine,97% UbeniMex(Bestatin) N-[(2S,3R)-3-AMino-2-hydroxy-4-phenylbutyryl]-L-leucine, 97% 500MG Bestatin, UbeniMex (2R)-2-[(2S,3R)-3-aMino-2-hydroxy-4-phenylbutanaMido]-4-Methylpentanoic acid (S)-2-((2S,3R)-3-aMino-2-hydroxy-4-phenylbutanaMido)-4-Methylpentanoic acid N-[(2S,3R)-3-AMino-2-hydroxy-4-phenylbutyryl]-L-leucine|(-)-N-[3(R)-AMino-2(S)-hydroxy-4-phenylbutyryl]-L-leucine [S-(R*,S*)]-N-(3-Amino-2-hydroxy-1-oxo-4-phenylbutyl)-L-leucine Bestatin, >=99% N-[(2S,3R)-3-Amino-2-hydroxy-4-phenylbutyryl]-L-leucine≥ 98% (HPLC) Ubenimex Ubenimex Bestatin USP/EP/BP Bestatin D10 Bestatin Impurity Bestatin, aminopeptidase inhibitor N-[(2S,3R)-3-Amino-2-hydroxy-4-phenylbutyryl]-L-leucine Ubenimex - Bio-X ? N-((2S,3R)-3-AMINO-2-HYDROXY-4-PHENYLBUTYRYL)-L-LEUCIN 99% (S)-2-((2S,3R)-3-Amino-2-hydroxy-4-phenylbutancarboxcarboxcarboxamido)-4-methylpentanoic acid UBENIMEX 58970-76-6 C16H24N2O4 CH32CHCH2CHNHCOCHOHCHNH2CH2C6H5CO2H Leucine Derivatives Peptide Synthesis Specialty Synthesis Unnatural Amino Acid Derivatives ProteaseInhibitors Pepetides Active Pharmaceutical Ingredients peptides Bestatin API Ubenimex