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Details

Stereochemistry ABSOLUTE
Molecular Formula 2C29H41NO6.C2H2O4
Molecular Weight 1089.3128
Optical Activity UNSPECIFIED
Defined Stereocenters 12 / 12
E/Z Centers 2
Charge 0

SHOW SMILES / InChI
Structure of BELORANIB HEMIOXALATE

SMILES

OC(=O)C(O)=O.[H][C@@]1([C@H](OC)[C@@H](CC[C@]12CO2)OC(=O)\C=C\C3=CC=C(OCCN(C)C)C=C3)[C@@]4(C)O[C@@H]4CC=C(C)C.[H][C@@]5([C@H](OC)[C@@H](CC[C@]56CO6)OC(=O)\C=C\C7=CC=C(OCCN(C)C)C=C7)[C@@]8(C)O[C@@H]8CC=C(C)C

InChI

InChIKey=ZKEMUPZLDSXZCX-CEVDDVLHSA-N
InChI=1S/2C29H41NO6.C2H2O4/c2*1-20(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;3-1(4)2(5)6/h2*7-12,14,23-24,26-27H,13,15-19H2,1-6H3;(H,3,4)(H,5,6)/b2*14-10+;/t2*23-,24-,26-,27-,28+,29+;/m11./s1

HIDE SMILES / InChI

Molecular Formula C29H41NO6
Molecular Weight 499.6389
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 6
E/Z Centers 1
Optical Activity UNSPECIFIED

Molecular Formula C2H2O4
Molecular Weight 90.0349
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Beloranib (also known as ZGN-433 or CKD-732), a fumagillin anticancer drug that initially was developed by CKD Pharmaceuticals for the treatment of solid tumors. Beloranib is a potent inhibitor of methionine aminopeptidase 2 (MetAP2), an enzyme that modulates the activity of key cellular processes that control metabolism. This drug was studied for the treatment of Prader-Willi syndrome and obesity caused by hypothalamic injury, including craniopharyngioma-associated obesity and severe obesity in the general population. European Commission has granted orphan drug designation for beloranib for the treatment of craniopharyngioma, a rare form of benign brain tumor and for the treatment of Prader-Willi syndrome. Beloran participated in phase III clinical trials to evaluate efficacy and safety in obese adolescent and adult subjects with Prader-Willi Syndrome, but these studies were terminated. In 2016, Zafgen, the company developed the drug, based on discussions with the regulatory authority and review of obstacles, costs and development timelines to gain marketing approval for beloranib, has decided to discontinue further development of the drug.

Approval Year

PubMed

PubMed

TitleDatePubMed
Absorption, distribution, metabolism, and excretion of CKD-732, a novel antiangiogenic fumagillin derivative, in rats, mice, and dogs.
2004 Feb
Novel inhibitors targeted to methionine aminopeptidase 2 (MetAP2) strongly inhibit the growth of cancers in xenografted nude model.
2005 Mar 10
Assessment of the anti-obesity effects of the TNP-470 analog, CKD-732.
2007 Apr
The development of MetAP-2 inhibitors in cancer treatment.
2012
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.
2012 Apr
Inhibition of the methionine aminopeptidase 2 enzyme for the treatment of obesity.
2014
Patents

Patents

Sample Use Guides

Subjects will receive ZGN-440 twice weekly subcutaneous injections for up to 28 weeks.
Route of Administration: Other
Substance Class Chemical
Created
by admin
on Sat Dec 16 11:07:18 GMT 2023
Edited
by admin
on Sat Dec 16 11:07:18 GMT 2023
Record UNII
4T7B8LC5I7
Record Status Validated (UNII)
Record Version
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Name Type Language
BELORANIB HEMIOXALATE
Common Name English
CKD 732
Code English
CKD-732
Code English
2-PROPENOIC ACID, 3-(4-(2-(DIMETHYLAMINO)ETHOXY)PHENYL)-, (3R,4S,5S,6R)-5-METHOXY-4-((2R,3R)-2-METHYL-3-(3-METHYL-2-BUTENYL)OXIRANYL)-1-OXASPIRO(2.5)OCT-6-YL ESTER, (2E)-, ETHANEDIOATE (2:1)
Systematic Name English
Code System Code Type Description
EPA CompTox
DTXSID90200996
Created by admin on Sat Dec 16 11:07:18 GMT 2023 , Edited by admin on Sat Dec 16 11:07:18 GMT 2023
PRIMARY
CAS
529511-79-3
Created by admin on Sat Dec 16 11:07:18 GMT 2023 , Edited by admin on Sat Dec 16 11:07:18 GMT 2023
PRIMARY
PUBCHEM
25144864
Created by admin on Sat Dec 16 11:07:18 GMT 2023 , Edited by admin on Sat Dec 16 11:07:18 GMT 2023
PRIMARY
FDA UNII
4T7B8LC5I7
Created by admin on Sat Dec 16 11:07:18 GMT 2023 , Edited by admin on Sat Dec 16 11:07:18 GMT 2023
PRIMARY
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