Ubenimex
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MedKoo CAT#: 206765

CAS#: 58970-76-6

Description: Ubenimex, also known as NK 421 and Bestatin, is a CD13 inhibitor. Ubenimex attenuates acquired sorafenib resistance in renal cell carcinoma by inhibiting Akt signaling in a lipophagy associated mechanism. Ubenimex synergistically enhances the effects of anticancer drugs in hepatocellular carcinoma. Ubenimex inhibits cell proliferation, migration and invasion by inhibiting the expression of APN and inducing autophagic cell death in prostate cancer cells.


Price and Availability

Size
Price

100mg
USD 150
1g
USD 650
10g
USD 3450
Size
Price

200mg
USD 250
2g
USD 1050
Size
Price

500mg
USD 450
5g
USD 1950

Ubenimex, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received. Delivery time: overnight (USA/Canada); 3-5 days (worldwide).


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 206765
Name: Ubenimex
CAS#: 58970-76-6
Chemical Formula: C16H24N2O4
Exact Mass: 308.1736
Molecular Weight: 308.378
Elemental Analysis: C, 62.32; H, 7.84; N, 9.08; O, 20.75


Synonym: Ubenimex, NK 421, NK-421, NK421, Bestatin, NSC 265489, NSC265489, NSC-265489

IUPAC/Chemical Name: ((2S,3R)-3-amino-2-hydroxy-4-phenylbutanoyl)-L-leucine

InChi Key: VGGGPCQERPFHOB-RDBSUJKOSA-N

InChi Code: 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

SMILES Code: CC(C)C[C@@H](C(O)=O)NC([C@@H](O)[C@H](N)CC1=CC=CC=C1)=O


Technical Data

Appearance:
White solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code:
293490


References

1: Liu S, Gao M, Wang X, Ding S, Lv J, Gao D, Wang Z, Niu Z. Ubenimex attenuates acquired sorafenib resistance in renal cell carcinoma by inhibiting Akt signaling in a lipophagy associated mechanism. Oncotarget. 2016 Nov 1. doi: 10.18632/oncotarget.13003. [Epub ahead of print] PubMed PMID: 27816967.

2: Jiang Y, Hou J, Li X, Huang Y, Wang X, Wu J, Zhang J, Xu W, Zhang Y. Discovery of a novel chimeric ubenimex-gemcitabine with potent oral antitumor activity. Bioorg Med Chem. 2016 Nov 15;24(22):5787-5795. doi: 10.1016/j.bmc.2016.09.033. PubMed PMID: 27670098.

3: Jiang Y, Li X, Hou J, Huang Y, Jia Y, Zou M, Zhang J, Wang X, Xu W, Zhang Y. Discovery of BC-01, a novel mutual prodrug (hybrid drug) of ubenimex and fluorouracil as anticancer agent. Eur J Med Chem. 2016 Oct 4;121:649-57. doi: 10.1016/j.ejmech.2016.05.068. PubMed PMID: 27322756.

4: Yamashita M, Wada H, Eguchi H, Ogawa H, Yamada D, Noda T, Asaoka T, Kawamoto K, Gotoh K, Umeshita K, Doki Y, Mori M. A CD13 inhibitor, ubenimex, synergistically enhances the effects of anticancer drugs in hepatocellular carcinoma. Int J Oncol. 2016 Jul;49(1):89-98. doi: 10.3892/ijo.2016.3496. PubMed PMID: 27121124; PubMed Central PMCID: PMC4902077.

5: Zheng J, Xiang J, Miao J, Yu Q, Hu C, Qin YP, Shu SQ, Nan F, Wang Y, Zhu XH. [Bioequivalence of Ubenimex Capsules in Healthy Volunteers]. Sichuan Da Xue Xue Bao Yi Xue Ban. 2016 Jan;47(1):85-9, 92. Chinese. PubMed PMID: 27062789.

6: Wang X, Niu Z, Jia Y, Cui M, Han L, Zhang Y, Liu Z, Bi D, Liu S. Ubenimex inhibits cell proliferation, migration and invasion by inhibiting the expression of APN and inducing autophagic cell death in prostate cancer cells. Oncol Rep. 2016 Apr;35(4):2121-30. doi: 10.3892/or.2016.4611. PubMed PMID: 26846372.

7: Liu S, Xie F, Wang H, Liu Z, Liu X, Sun L, Niu Z. Ubenimex inhibits cell proliferation, migration and invasion in renal cell carcinoma: the effect is autophagy-associated. Oncol Rep. 2015 Mar;33(3):1372-80. doi: 10.3892/or.2014.3693. PubMed PMID: 25571917.

8: Zheng YB, Gong JH, Li Y, Zhen YS. [Inhibition of tumor cell invasion and induction of apoptosis by ubenimex]. Yao Xue Xue Bao. 2012 Dec;47(12):1593-8. Chinese. PubMed PMID: 23460963.

9: Wang Z, Xiang J, Yu Q, Liang MZ, Nan F, Qin YP. [Determination of ubenimex in human plasma by HPLC-MS/MS]. Sichuan Da Xue Xue Bao Yi Xue Ban. 2012 Jul;43(4):609-11, 630. Chinese. PubMed PMID: 22997907.

10: Wakita A, Ohtake S, Takada S, Yagasaki F, Komatsu H, Miyazaki Y, Kubo K, Kimura Y, Takeshita A, Adachi Y, Kiyoi H, Yamaguchi T, Yoshida M, Ohnishi K, Miyawaki S, Naoe T, Ueda R, Ohno R. Randomized comparison of fixed-schedule versus response-oriented individualized induction therapy and use of ubenimex during and after consolidation therapy for elderly patients with acute myeloid leukemia: the JALSG GML200 Study. Int J Hematol. 2012 Jul;96(1):84-93. doi: 10.1007/s12185-012-1105-y. PubMed PMID: 22639053.

11: Xu JW, Li CG, Huang XE, Li Y, Huo JG. Ubenimex capsule improves general performance and chemotherapy related toxicity in advanced gastric cancer cases. Asian Pac J Cancer Prev. 2011;12(4):985-7. PubMed PMID: 21790238.

12: Tsukamoto H, Shibata K, Kajiyama H, Terauchi M, Nawa A, Kikkawa F. Aminopeptidase N (APN)/CD13 inhibitor, Ubenimex, enhances radiation sensitivity in human cervical cancer. BMC Cancer. 2008 Mar 19;8:74. doi: 10.1186/1471-2407-8-74. PubMed PMID: 18366676; PubMed Central PMCID: PMC2289833.

13: Qian XJ, Lin MF. [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]. Zhonghua Xue Ye Xue Za Zhi. 2006 Jul;27(7):445-8. Chinese. PubMed PMID: 17147245.

14: Kanamori H, Takasaki H, Takabayashi M, Yamaji S, Koharazawa H, Fujimaki K, Taguchi J, Ishigatsubo Y. Long-term cytogenetic remission with ubenimex monotherapy in a case of chronic myeloid leukemia. Anticancer Drugs. 2004 Aug;15(7):729-31. PubMed PMID: 15269606.

15: Sugano O, Muto A, Kato M, Ono K. [A case of renal cell carcinoma with lymph node metastasis keeping remission for five years by adjuvant immunotherapy with ubenimex]. Gan To Kagaku Ryoho. 2003 Oct;30(10):1519-22. Japanese. PubMed PMID: 14584289.

16: Hirayama Y, Sakamaki S, Takayanagi N, Tsuji Y, Sagawa T, Chiba H, Matsunaga T, Niitsu Y. [Chemotherapy with ubenimex corresponding to patient age and organ disorder for 18 cases of acute myelogeneous leukemia in elderly patients--effects, complications and long-term survival]. Gan To Kagaku Ryoho. 2003 Aug;30(8):1113-8. Japanese. PubMed PMID: 12938265.

17: He JS, Lin MF, Mai WY, Qian WB. [Mechanisms of inhibitory effect of Ubenimex on human leukemic cells]. Zhejiang Da Xue Xue Bao Yi Xue Ban. 2002 Aug;31(4):259-264. Chinese. PubMed PMID: 12601905.

18: Okada H, Nomi K, Hamatani S, Kuromi T, Nanba M, Imai T, Isobe K, Itoh S. Induction of graft-versus-host disease and a graft-versus-leukemia effect using ubenimex in a patient with infantile leukemia relapsing after an unrelated cord blood transplant. Bone Marrow Transplant. 2002 Oct;30(7):463-5. PubMed PMID: 12368960.

19: Li P, Xu Y, Ren L, Yang Y, Zhang H, Luo D, Hao D, Hong Y, Chen L, Xie M. [Effects of ubenimex ( bestatin) on the immunity of patients with squamous cell lung carcinoma treated with chemotherapy]. Zhongguo Fei Ai Za Zhi. 2001 Oct 20;4(5):364-6. doi: 10.3779/j.issn.1009-3419.2001.05.14. Chinese. PubMed PMID: 21059319.

20: Horikoshi A, Irie T, Ishizuka H, Ohkubo T, Hosokawa Y, Sawada S. Effect of ubenimex on a CD5-CD13+ CLL patient with an aggressive clinical course. Int J Hematol. 2000 Oct;72(3):384-5. PubMed PMID: 11185999.