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Details

Stereochemistry ABSOLUTE
Molecular Formula C29H41NO6
Molecular Weight 499.6389
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of BELORANIB

SMILES

[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

InChI

InChIKey=ZEZFKUBILQRZCK-MJSCXXSSSA-N
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

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

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 17:06:15 GMT 2023
Edited
by admin
on Sat Dec 16 17:06:15 GMT 2023
Record UNII
FI471K8BU6
Record Status Validated (UNII)
Record Version
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Name Type Language
BELORANIB
INN   WHO-DD  
INN  
Official Name English
beloranib [INN]
Common Name English
ZGN-433
Code English
(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
Systematic Name English
ZGN-440
Code English
Beloranib [WHO-DD]
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 385012
Created by admin on Sat Dec 16 17:06:15 GMT 2023 , Edited by admin on Sat Dec 16 17:06:15 GMT 2023
NCI_THESAURUS C1742
Created by admin on Sat Dec 16 17:06:15 GMT 2023 , Edited by admin on Sat Dec 16 17:06:15 GMT 2023
EU-Orphan Drug EU/3/14/1287
Created by admin on Sat Dec 16 17:06:15 GMT 2023 , Edited by admin on Sat Dec 16 17:06:15 GMT 2023
Code System Code Type Description
DRUG BANK
DB12671
Created by admin on Sat Dec 16 17:06:15 GMT 2023 , Edited by admin on Sat Dec 16 17:06:15 GMT 2023
PRIMARY
INN
9056
Created by admin on Sat Dec 16 17:06:15 GMT 2023 , Edited by admin on Sat Dec 16 17:06:15 GMT 2023
PRIMARY
EVMPD
SUB179793
Created by admin on Sat Dec 16 17:06:15 GMT 2023 , Edited by admin on Sat Dec 16 17:06:15 GMT 2023
PRIMARY
FDA UNII
FI471K8BU6
Created by admin on Sat Dec 16 17:06:15 GMT 2023 , Edited by admin on Sat Dec 16 17:06:15 GMT 2023
PRIMARY
CAS
609845-93-4
Created by admin on Sat Dec 16 17:06:15 GMT 2023 , Edited by admin on Sat Dec 16 17:06:15 GMT 2023
NON-SPECIFIC STEREOCHEMISTRY
PUBCHEM
6918502
Created by admin on Sat Dec 16 17:06:15 GMT 2023 , Edited by admin on Sat Dec 16 17:06:15 GMT 2023
PRIMARY
NCI_THESAURUS
C90656
Created by admin on Sat Dec 16 17:06:15 GMT 2023 , Edited by admin on Sat Dec 16 17:06:15 GMT 2023
PRIMARY
EPA CompTox
DTXSID40179800
Created by admin on Sat Dec 16 17:06:15 GMT 2023 , Edited by admin on Sat Dec 16 17:06:15 GMT 2023
PRIMARY
WIKIPEDIA
BELORANIB
Created by admin on Sat Dec 16 17:06:15 GMT 2023 , Edited by admin on Sat Dec 16 17:06:15 GMT 2023
PRIMARY
CAS
251111-30-5
Created by admin on Sat Dec 16 17:06:15 GMT 2023 , Edited by admin on Sat Dec 16 17:06:15 GMT 2023
PRIMARY
SMS_ID
100000165899
Created by admin on Sat Dec 16 17:06:15 GMT 2023 , Edited by admin on Sat Dec 16 17:06:15 GMT 2023
PRIMARY
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