Combretastatin A-1 phosphate

Investigational

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

Structure Search

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

Molecular Formula	C18H22O12P2
Molecular Weight	492.3076
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	1
Optical Activity	NONE

Description
Sources: http://investor.mateon.com/news-releases/news-release-details/oxigene-announces-oxi4503-granted-orphan-designation-treatment | https://clinicaltrials.gov/ct2/show/NCT02576301 | https://clinicaltrials.gov/ct2/show/NCT00977210 | https://adisinsight.springer.com/drugs/800016894 | https://www.ncbi.nlm.nih.gov/pubmed/21276042

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

Title	Date	PubMed
Effect of the second-generation vascular disrupting agent OXi4503 on tumor vascularity.	2006 Jul 1	16818709
Effect of vascular targeting agent Oxi4503 on tumor cell kinetics in a mouse model of colorectal liver metastasis.	2007 Jul-Aug	17695520
The new vascular disrupting agent combretastatin-A1-disodium-phosphate (OXi4503) enhances tumour response to mild hyperthermia and thermoradiosensitization.	2007 Nov	18038290
Alterations in vascular architecture and permeability following OXi4503 treatment.	2008 Jan	18043126

Sample Use Guides

In Vivo Use Guide

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

Substance Class	Chemical Created by `admin` on `Fri Dec 15 19:41:10 GMT 2023` Edited by `admin` on `Fri Dec 15 19:41:10 GMT 2023`
Record UNII	JH6Z94GLUD
Record Status	`Validated (UNII)`
Record Version

Download

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