U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C18H22O12P2
Molecular Weight 492.3076
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of Combretastatin A-1 phosphate

SMILES

COC1=CC=C(\C=C/C2=CC(OC)=C(OC)C(OC)=C2)C(OP(O)(O)=O)=C1OP(O)(O)=O

InChI

InChIKey=GSOXMQLWUDQTNT-WAYWQWQTSA-N
InChI=1S/C18H22O12P2/c1-25-13-8-7-12(16(29-31(19,20)21)18(13)30-32(22,23)24)6-5-11-9-14(26-2)17(28-4)15(10-11)27-3/h5-10H,1-4H3,(H2,19,20,21)(H2,22,23,24)/b6-5-

HIDE SMILES / InChI
Oxi0-4503 (now known as combretastatin A1 phosphate), a diphosphate prodrug of combretastatin A1, was developed by Mateon therapeutics as a second-generation, dual-mechanism vascular disrupting agent from the combretastatin family. On November 21, 2012, Oxi-4503 has been granted orphan designation by the US Food and Drug Administration for the treatment of acute myelogenous leukemia. It is known that the orphan drug designation qualifies a company for several benefits, including the potential for market exclusivity, development grants, and tax credits. Oxi0-4503 is currently participating in phase I/II clinical trial the treatment of patients with acute myelogenous leukemia or myelodysplastic syndrome. In addition, phase I clinical trial was successfully completed where was studied the safety of Oxi0-4503 in patients with advanced solid tumors.

Approval Year

PubMed

PubMed

TitleDatePubMed
Effect of the second-generation vascular disrupting agent OXi4503 on tumor vascularity.
2006 Jul 1
Effect of vascular targeting agent Oxi4503 on tumor cell kinetics in a mouse model of colorectal liver metastasis.
2007 Jul-Aug
The new vascular disrupting agent combretastatin-A1-disodium-phosphate (OXi4503) enhances tumour response to mild hyperthermia and thermoradiosensitization.
2007 Nov
Alterations in vascular architecture and permeability following OXi4503 treatment.
2008 Jan

Sample Use Guides

Solid Tumors: OXi4503 will be administered weekly for 3 weeks followed by a week with no treatment. The starting dose will be 0.06 mg/m2 given as an intravenous infusion over 10 minutes
Route of Administration: Intravenous
Name Type Language
Combretastatin A-1 phosphate
Common Name English
COMBRETASTATIN A-1 BIS(PHOSPHATE)
Common Name English
COMBRETASTATIN A1 DIPHOSPHATE
Common Name English
Combretastatin A1 diphosphate [WHO-DD]
Common Name English
CA1P
Common Name English
1,2-BENZENEDIOL, 3-METHOXY-6-((1Z)-2-(3,4,5-TRIMETHOXYPHENYL)ETHENYL)-, 1,2-BIS(DIHYDROGEN PHOSPHATE)
Common Name English
OXI-4503
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C67421
Created by admin on Fri Dec 15 19:41:10 GMT 2023 , Edited by admin on Fri Dec 15 19:41:10 GMT 2023
EU-Orphan Drug EU/3/15/1587
Created by admin on Fri Dec 15 19:41:10 GMT 2023 , Edited by admin on Fri Dec 15 19:41:10 GMT 2023
FDA ORPHAN DRUG 382412
Created by admin on Fri Dec 15 19:41:10 GMT 2023 , Edited by admin on Fri Dec 15 19:41:10 GMT 2023
Code System Code Type Description
DRUG BANK
DB05143
Created by admin on Fri Dec 15 19:41:10 GMT 2023 , Edited by admin on Fri Dec 15 19:41:10 GMT 2023
PRIMARY
SMS_ID
100000175788
Created by admin on Fri Dec 15 19:41:10 GMT 2023 , Edited by admin on Fri Dec 15 19:41:10 GMT 2023
PRIMARY
FDA UNII
JH6Z94GLUD
Created by admin on Fri Dec 15 19:41:10 GMT 2023 , Edited by admin on Fri Dec 15 19:41:10 GMT 2023
PRIMARY
CAS
288847-35-8
Created by admin on Fri Dec 15 19:41:10 GMT 2023 , Edited by admin on Fri Dec 15 19:41:10 GMT 2023
PRIMARY
NCI_THESAURUS
C84867
Created by admin on Fri Dec 15 19:41:10 GMT 2023 , Edited by admin on Fri Dec 15 19:41:10 GMT 2023
PRIMARY
PUBCHEM
6918546
Created by admin on Fri Dec 15 19:41:10 GMT 2023 , Edited by admin on Fri Dec 15 19:41:10 GMT 2023
PRIMARY