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Details

Stereochemistry ACHIRAL
Molecular Formula C8H17Cl2N2O2P
Molecular Weight 275.113
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 2

SHOW SMILES / InChI
Structure of 1,1′-Phosphinicobis[1-(2-chloroethyl)aziridinium]

SMILES

OP(=O)([N+]1(CCCl)CC1)[N+]2(CCCl)CC2

InChI

InChIKey=RLEWPJCSHPMUBB-UHFFFAOYSA-O
InChI=1S/C8H16Cl2N2O2P/c9-1-3-11(5-6-11)15(13,14)12(4-2-10)7-8-12/h1-8H2/q+1/p+1

HIDE SMILES / InChI
Canfosfamide is a modified glutathione analogue and nitrogen mustard prodrug, with potential antineoplastic activity. Canfosfamide is selectively activated by glutathione S-transferase P1-1 an enzyme that is over-expressed in many human cancers including ovarian cancer. GST P1-1-mediated cleavage leads to an active cytotoxic phosphorodiamidate alkylating metabolite that forms covalent linkages with nucleophilic centers in tumor cell DNA, which may induce a cellular stress response and cytotoxicity, and decrease tumor cell proliferation. Preclinical studies showed that canfosfamide inhibited the growth and was cytotoxic to a wide range of established cancer cell lines including those derived from ovarian cancer (OVCAR3, HEY, SK-OV-3). Canfosfamide treatment inhibited cancer cell proliferation and induced apoptosis through the activation of the cellular stress response kinase pathway. The cytotoxic activity of canfosfamide correlated with the expression of GST P1-1. Cancer cells in which GST expression levels were increased by transfection with the GST P1-1 gene, were more sensitive to the cytotoxic effects of canfosfamide than the parental cell lines Canfosfamide in combination with pegylated liposomal doxorubicin is well tolerated and active in platinum and paclitaxel refractory or resistant ovarian cancer.

Approval Year

PubMed

PubMed

TitleDatePubMed
Phase 1-2a multicenter dose-ranging study of canfosfamide in combination with carboplatin and paclitaxel as first-line therapy for patients with advanced non-small cell lung cancer.
2009 Nov
Randomized phase III study of canfosfamide in combination with pegylated liposomal doxorubicin compared with pegylated liposomal doxorubicin alone in platinum-resistant ovarian cancer.
2010 Jul
Phase 2 study of canfosfamide in combination with pegylated liposomal doxorubicin in platinum and paclitaxel refractory or resistant epithelial ovarian cancer.
2010 Mar 11
Patents

Patents

Sample Use Guides

canfosfamide at 1000 mg/m² and pegylated liposomal doxorubicin at 50 mg/m² intravenously
Route of Administration: Intravenous
Name Type Language
1,1′-Phosphinicobis[1-(2-chloroethyl)aziridinium]
Systematic Name English
Aziridinium, 1,1′-phosphinicobis[1-(2-chloroethyl)-
Systematic Name English
Code System Code Type Description
FDA UNII
87MF79KUY8
Created by admin on Fri Jul 07 00:54:28 UTC 2023 , Edited by admin on Fri Jul 07 00:54:28 UTC 2023
PRIMARY
PUBCHEM
162677503
Created by admin on Fri Jul 07 00:54:28 UTC 2023 , Edited by admin on Fri Jul 07 00:54:28 UTC 2023
PRIMARY
CAS
1476773-63-3
Created by admin on Fri Jul 07 00:54:28 UTC 2023 , Edited by admin on Fri Jul 07 00:54:28 UTC 2023
PRIMARY