Canfosfamide

DRACPC ID  DRACPC0032

Active Ingredients   Canfosfamide

Description  A modified glutathione analogue and nitrogen mustard prodrug, with potential antineoplastic activity. Canfosfamide is selectively activated by glutathione S-transferase P1-1 into an 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. Glutathione S-transferase P1-1 is an enzyme that is overexpressed in many human malignancies.

Synonyms  (2R)-L-gamma-Glutamyl-3-((2-((bis(bis(2-chloroethyl)amino)phosphinyl)oxy)ethyl)sulfonyl)-L-alanyl-2-phenylglycine; Ter 286; Canfosfamide

Type  Small Molecule

Disease  Various forms of cancer

Classification

  

Peptide and derivative

Structure Information


Molecular Formula  C26H40Cl4N5O10PS

Molecular Weight  787.5

Active Sequence  XXx

Sequence Length  3

Modification  X(1)=gGlu, X(2)=Ala(Unk), x=D-Phg

Structure

 

Show IUPAC/InChI/SMILES

IUPAC Name  (2S)-2-amino-5-[[(2R)-3-[2-[bis[bis(2-chloroethyl)amino]phosphoryloxy]ethylsulfonyl]-1-[[(R)-carboxy(phenyl)methyl]amino]-1-oxopropan-2-yl]amino]-5-oxopentanoic acid

InChI  InChI=1S/C26H40Cl4N5O10PS/c27-8-12-34(13-9-28)46(42,35(14-10-29)15-11-30)45-16-17-47(43,44)18-21(32-22(36)7-6-20(31)25(38)39)24(37)33-23(26(40)41)19-4-2-1-3-5-19/h1-5,20-21,23H,6-18,31H2,(H,32,36)(H,33,37)(H,38,39)(H,40,41)/t20-,21-,23+/m0/s1

InChI_Key OJLHWPALWODJPQ-QNWVGRARSA-N

SMILES  O=C(O)[C@@H](N)CCC(N[C@@H](CS(=O)(CCOP(N(CCCl)CCCl)(N(CCCl)CCCl)=O)=O)C(N[C@@H](C(O)=O)C1=CC=CC=C1)=O)=O

External Codes


PubChem CID  5312109

DrugBank Accession Number  DB04972

NCI Thesaurus Code  C83581  

UNII  1RS284BFUI   GSRS

CAS  158382-37-7



Drug approval


Drug indication
    Intended for the treatment of various forms of cancer.

    The drug is not approved.

ClinicalTrials.gov Identifier Title Condition or disease Phase Purpose
NCT01148108 Phase 2 Study of Canfosfamide HCl for Injection (Telcyta®, TLK286)in Refractory or Relapsed Mantle Cell Lymphoma (MCL), Diffuse Large B Cell Lymphoma (DLBCL) and Multiple Myeloma (MM) Mantle Cell Lymphoma; B Cell Lymphoma; Multiple Myeloma Phase 2 Treatment
NCT00022347 A Phase II Study of TLK 286 in Platinum Resistant Advanced Epithelial Ovarian Cancer Fallopian Tube Cancer; Ovarian Cancer; Primary Peritoneal Cavity Cancer Phase 2 Treatment
NCT00036920 Phase II Study Of TLK286 For The Treatment Of Advanced Non-Small Cell Lung Cancer Lung Cancer Phase 2 Treatment
NCT00350948 Phase 3 Randomized Study of TLK286 (Telcyta®) in Combination With Liposomal Doxorubicin (Doxil/Caelyx)Versus Liposomal Doxorubicin (Doxil/Caelyx) as Second-Line Therapy in Platinum Refractory or Resistant Ovarian Cancer (ASSIST-5) Ovarian Neoplasms Phase 3 Treatment

    More clinical information is obtained from ClinicalTrials.gov.





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