Ubenimex
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MedKoo CAT#: 206765

CAS#: 58970-76-6 (free base)

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.


Chemical Structure

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Ubenimex
CAS# 58970-76-6 (free base)

Theoretical Analysis

MedKoo Cat#: 206765
Name: Ubenimex
CAS#: 58970-76-6 (free base)
Chemical Formula: C16H24N2O4
Exact Mass: 308.17
Molecular Weight: 308.380
Elemental Analysis: C, 62.32; H, 7.84; N, 9.08; O, 20.75

Price and Availability

Size Price Availability Quantity
50mg USD 150 Ready to ship
100mg USD 225 Ready to ship
250mg USD 450 Ready to ship
500mg USD 750 Ready to ship
1g USD 1250 Ready to ship
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Related CAS #: 58970-76-6 (free base)   65391-42-6 (HCl)    

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

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).

HS Tariff Code: 2934.99.9001

More Info:

Biological target: Ubenimex is an aminopeptidase-B and leukotriene (LT) A4 hydrolase inhibitor.
In vitro activity: The role of ubenimex in inhibiting migration and invasion was investigated by downregulating APN (Aminopeptidase N) expression levels to induce autophagic cell death and apoptosis in bladder cancer cells. Treatment with ubenimex was accompanied by decreased Akt expression, indicating that ubenimex may have similar functions to Akt inhibitors. Results also indicated that ubenimex inhibited cell migration and invasion in bladder cancer cells. Furthermore, ubenimex also induced autophagic cell death and apoptosis, which suggested that mixed programmed cell death occurred in ubenimex‑treated bladder cancer cells. Reference: Mol Med Rep. 2018 Mar;17(3):4531-4539. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5802231/
In vivo activity: The antitumor growth effect of ubenimex was evaluated in vivo. Tumors were induced by the injection of PC-3 cells into nude mice. The body weights of the mice were measured weekly. Fig. 7A shows that none of the treatments produced any loss in body weight, which would constitute a sign of toxicity. The tumor weight in the nude mice was significantly reduced in a dose-dependent manner following ubenimex treatment (Fig. 7B and C). Thus, it can be demonstrated that ubenimex inhibited PC-3 cell proliferation in vivo. Reference: Oncol Rep. 2016 Apr;35(4):2121-30. https://www.spandidos-publications.com/or/35/4/2121

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 6.2 20.01
PBS (Ph 7.2) 0.2 0.52

Preparing Stock Solutions

The following data is based on the product molecular weight 308.38 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Guo Q, Jing FJ, Xu W, Li X, Li X, Sun JL, Xing XM, Zhou CK, Jing FB. Ubenimex induces autophagy inhibition and EMT suppression to overcome cisplatin resistance in GC cells by perturbing the CD13/EMP3/PI3K/AKT/NF-κB axis. Aging (Albany NY). 2019 Dec 31;12(1):80-105. doi: 10.18632/aging.102598. Epub 2019 Dec 31. PMID: 31895687; PMCID: PMC6977684. 2. Wang X, Liu Y, Liu W, Zhang Y, Guo F, Zhang L, Cui M, Liu S, Wu R. Ubenimex, an APN inhibitor, could serve as an anti‑tumor drug in RT112 and 5637 cells by operating in an Akt‑associated manner. Mol Med Rep. 2018 Mar;17(3):4531-4539. doi: 10.3892/mmr.2018.8402. Epub 2018 Jan 9. PMID: 29328441; PMCID: PMC5802231.
In vitro protocol: 1. Guo Q, Jing FJ, Xu W, Li X, Li X, Sun JL, Xing XM, Zhou CK, Jing FB. Ubenimex induces autophagy inhibition and EMT suppression to overcome cisplatin resistance in GC cells by perturbing the CD13/EMP3/PI3K/AKT/NF-κB axis. Aging (Albany NY). 2019 Dec 31;12(1):80-105. doi: 10.18632/aging.102598. Epub 2019 Dec 31. PMID: 31895687; PMCID: PMC6977684. 2. Wang X, Liu Y, Liu W, Zhang Y, Guo F, Zhang L, Cui M, Liu S, Wu R. Ubenimex, an APN inhibitor, could serve as an anti‑tumor drug in RT112 and 5637 cells by operating in an Akt‑associated manner. Mol Med Rep. 2018 Mar;17(3):4531-4539. doi: 10.3892/mmr.2018.8402. Epub 2018 Jan 9. PMID: 29328441; PMCID: PMC5802231.
In vivo protocol: 1. 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. Epub 2016 Feb 3. PMID: 26846372.

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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.