Beloranib

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 584334

CAS#: 251111-30-5

Description: Beloranib is a fumagillin anticancer drug that belongs to an angiogenesis inhibitor.


Price and Availability

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Beloranib is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 584334
Name: Beloranib
CAS#: 251111-30-5
Chemical Formula: C29H41NO6
Exact Mass: 499.2934
Molecular Weight: 499.648
Elemental Analysis: C, 69.71; H, 8.27; N, 2.80; O, 19.21


Synonym: Beloranib; CKD-732; ZGN 440

IUPAC/Chemical Name: (3R,4S,5S,6R)-5-Methoxy-4-((2R,3R)-2-methyl-3-(3-methylbut-2-en-1-yl)oxiran-2-yl)-1-oxaspiro(2.5)octan-6-yl (2E)-3-(4-(2-(dimethylamino)ethoxy)phenyl)prop-2-enoate

InChi Key: ZEZFKUBILQRZCK-MJSCXXSSSA-N

InChi Code: InChI=1S/C29H41NO6/c1-20(2)7-13-24-28(3,36-24)27-26(32-6)23(15-16-29(27)19-34-29)35-25(31)14-10-21-8-11-22(12-9-21)33-18-17-30(4)5/h7-12,14,23-24,26-27H,13,15-19H2,1-6H3/b14-10+/t23-,24-,26-,27-,28+,29+/m1/s1

SMILES Code: O=C(O[C@H](CC1)[C@@H](OC)[C@H]([C@@]2(C)O[C@@H]2C/C=C(C)\C)[C@]31CO3)/C=C/C4=CC=C(OCCN(C)C)C=C4


Technical Data

Appearance:
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

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2: Arch JR. Horizons in the Pharmacotherapy of Obesity. Curr Obes Rep. 2015 Dec;4(4):451-9. doi: 10.1007/s13679-015-0177-4. Review. PubMed PMID: 26346394.

3: George M, Rajaram M, Shanmugam E. New and emerging drug molecules against obesity. J Cardiovasc Pharmacol Ther. 2014 Jan;19(1):65-76. doi: 10.1177/1074248413501017. Epub 2013 Sep 24. Review. PubMed PMID: 24064009.

4: Joharapurkar AA, Dhanesha NA, Jain MR. Inhibition of the methionine aminopeptidase 2 enzyme for the treatment of obesity. Diabetes Metab Syndr Obes. 2014 Feb 28;7:73-84. doi: 10.2147/DMSO.S56924. eCollection 2014. Review. PubMed PMID: 24611021; PubMed Central PMCID: PMC3944999.

5: Shin SJ, Ahn JB, Park KS, Lee YJ, Hong YS, Kim TW, Kim HR, Rha SY, Roh JK, Kim DH, Kim C, Chung HC. A Phase Ib pharmacokinetic study of the anti-angiogenic agent CKD-732 used in combination with capecitabine and oxaliplatin (XELOX) in metastatic colorectal cancer patients who progressed on irinotecan-based chemotherapy. Invest New Drugs. 2012 Apr;30(2):672-80. doi: 10.1007/s10637-010-9625-x. Epub 2010 Dec 29. PubMed PMID: 21188464.

6: Hughes TE, Kim DD, Marjason J, Proietto J, Whitehead JP, Vath JE. Ascending dose-controlled trial of beloranib, a novel obesity treatment for safety, tolerability, and weight loss in obese women. Obesity (Silver Spring). 2013 Sep;21(9):1782-8. doi: 10.1002/oby.20356. Epub 2013 May 25. PubMed PMID: 23512440.

7: Shin SJ, Jeung HC, Ahn JB, Rha SY, Roh JK, Park KS, Kim DH, Kim C, Chung HC. A phase I pharmacokinetic and pharmacodynamic study of CKD-732, an antiangiogenic agent, in patients with refractory solid cancer. Invest New Drugs. 2010 Oct;28(5):650-8. doi: 10.1007/s10637-009-9287-8. Epub 2009 Jul 8. PubMed PMID: 19585083.

8: Yin SQ, Wang JJ, Zhang CM, Liu ZP. The development of MetAP-2 inhibitors in cancer treatment. Curr Med Chem. 2012;19(7):1021-35. Review. PubMed PMID: 22229417.

9: Howland RH. Aspergillus, angiogenesis, and obesity: the story behind beloranib. J Psychosoc Nurs Ment Health Serv. 2015 Mar;53(3):13-6. doi: 10.3928/02793695-20150219-01. Review. PubMed PMID: 25751824.

10: Jackson VM, Price DA, Carpino PA. Investigational drugs in Phase II clinical trials for the treatment of obesity: implications for future development of novel therapies. Expert Opin Investig Drugs. 2014 Aug;23(8):1055-66. doi: 10.1517/13543784.2014.918952. Epub 2014 Jul 7. Review. PubMed PMID: 25000213.

11: Lee HS, Choi WK, Son HJ, Lee SS, Kim JK, Ahn SK, Hong CI, Min HK, Kim M, Myung SW. Absorption, distribution, metabolism, and excretion of CKD-732, a novel antiangiogenic fumagillin derivative, in rats, mice, and dogs. Arch Pharm Res. 2004 Feb;27(2):265-72. PubMed PMID: 15029870.

12: Maksimov ML, Svistunov AA, Tarasov VV, Chubarev VN, Ávila-Rodriguez M, Barreto GE, Dralova OV, Aliev G. Approaches for the Development of Drugs for Treatment of Obesity and Metabolic Syndrome. Curr Pharm Des. 2016;22(7):895-903. Review. PubMed PMID: 26648466.

13: Kim YM, An JJ, Jin YJ, Rhee Y, Cha BS, Lee HC, Lim SK. Assessment of the anti-obesity effects of the TNP-470 analog, CKD-732. J Mol Endocrinol. 2007 Apr;38(4):455-65. PubMed PMID: 17446235.

14: Kim EJ, Shin WH. General pharmacology of CKD-732, a new anticancer agent: effects on central nervous, cardiovascular, and respiratory system. Biol Pharm Bull. 2005 Feb;28(2):217-23. PubMed PMID: 15684472.

15: Kim JH, Lee SK, Ki MH, Choi WK, Ahn SK, Shin HJ, Hong CI. Development of parenteral formulation for a novel angiogenesis inhibitor, CKD-732 through complexation with hydroxypropyl-beta-cyclodextrin. Int J Pharm. 2004 Mar 19;272(1-2):79-89. PubMed PMID: 15019071.

16: Rhee Y, Park SY, Kim YM, Lee S, Lim SK. Angiogenesis inhibitor attenuates parathyroid hormone-induced anabolic effect. Biomed Pharmacother. 2009 Jan;63(1):63-8. doi: 10.1016/j.biopha.2007.10.013. Epub 2007 Nov 20. PubMed PMID: 18457934.

17: Chun E, Han CK, Yoon JH, Sim TB, Kim YK, Lee KY. Novel inhibitors targeted to methionine aminopeptidase 2 (MetAP2) strongly inhibit the growth of cancers in xenografted nude model. Int J Cancer. 2005 Mar 10;114(1):124-30. PubMed PMID: 15523682.

18: Myung SW, Kim HY, Min HK, Kim DH, Kim M, Cho HW, Lee HS, Kim JK, Hong CI. The identification of in vitro metabolites of CKD-732 by liquid chromatography/tandem mass spectrometry. Rapid Commun Mass Spectrom. 2002;16(21):2048-53. PubMed PMID: 12391579.

19: Kim DD, Krishnarajah J, Lillioja S, de Looze F, Marjason J, Proietto J, Shakib S, Stuckey BG, Vath JE, Hughes TE. Efficacy and safety of beloranib for weight loss in obese adults: a randomized controlled trial. Diabetes Obes Metab. 2015 Jun;17(6):566-72. doi: 10.1111/dom.12457. Epub 2015 Mar 31. PubMed PMID: 25732625.

20: Morgen M, Jöst C, Malz M, Janowski R, Niessing D, Klein CD, Gunkel N, Miller AK. Spiroepoxytriazoles Are Fumagillin-like Irreversible Inhibitors of MetAP2 with Potent Cellular Activity. ACS Chem Biol. 2016 Apr 15;11(4):1001-11. doi: 10.1021/acschembio.5b00755. Epub 2016 Jan 19. PubMed PMID: 26686773.