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Details

Stereochemistry ACHIRAL
Molecular Formula C18H18O12P2.4Na
Molecular Weight 580.2349
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of Combretastatin A-1 phosphate tetrasodium salt

SMILES

[Na+].[Na+].[Na+].[Na+].COC1=CC=C(\C=C/C2=CC(OC)=C(OC)C(OC)=C2)C(OP([O-])([O-])=O)=C1OP([O-])([O-])=O

InChI

InChIKey=NRKFVEPAQNCYNJ-YGGCHVFLSA-J
InChI=1S/C18H22O12P2.4Na/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);;;;/q;4*+1/p-4/b6-5-;;;;

HIDE SMILES / InChI

Molecular Formula Na
Molecular Weight 22.9898
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C18H18O12P2
Molecular Weight 488.2758
Charge -4
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

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
Substance Class Chemical
Created
by admin
on Sat Dec 16 10:40:49 GMT 2023
Edited
by admin
on Sat Dec 16 10:40:49 GMT 2023
Record UNII
3D67LX3H83
Record Status Validated (UNII)
Record Version
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Name Type Language
Combretastatin A-1 phosphate tetrasodium salt
Common Name English
Tetrasodium combretastatin A1 diphosphate
Common Name English
Combretastatin A1 diphosphate tetrasodium salt
Common Name English
1,2-Benzenediol, 3-methoxy-6-[(1Z)-2-(3,4,5-trimethoxyphenyl)ethenyl]-, 1,2-bis(dihydrogen phosphate), sodium salt (1:4)
Systematic Name English
Code System Code Type Description
CAS
288847-34-7
Created by admin on Sat Dec 16 10:40:49 GMT 2023 , Edited by admin on Sat Dec 16 10:40:49 GMT 2023
PRIMARY
FDA UNII
3D67LX3H83
Created by admin on Sat Dec 16 10:40:49 GMT 2023 , Edited by admin on Sat Dec 16 10:40:49 GMT 2023
PRIMARY
PUBCHEM
6918545
Created by admin on Sat Dec 16 10:40:49 GMT 2023 , Edited by admin on Sat Dec 16 10:40:49 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
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ACTIVE MOIETY