1745. Canfosfamide

Nomenclature

CAS number: 158382-37-7
(2R)-l-γ-Glutamyl-3-[[2-[[bis[bis(2-chloroethyl)amino]phosphinyl]oxy]ethyl]sulfonyl]-l-alanyl-2-phenylglycine; γ-glutamyl-α-amino-β-((2-ethyl-N,N,N′,N′-tetrakis(2-chloro)ethylphosphoramidate)sulfonyl)propionyl-(R)-(-)phenylglycine; TER-286.
C26H40Cl4N5O10PS; mol wt 787.47.
C 39.66%, H 5.12%, Cl 18.01%, N 8.89%, O 20.32%, P 3.93%, S 4.07%.

Description and references

Nitrogen mustard prodrug preferentially activated by glutathione S-transferase P1-1. Prepn: M. H. Lyttle et al., J. Med. Chem. 37, 1501 (1994); L. M. Kauvar et al., WO 9509866; eidem, US 5556942 (1995, 1996 both to Terrapin). Mechanism of activation: A. Satyam et al., J. Med. Chem. 39, 1736 (1996). In vitro and in vivo antitumor and myelosuppressive effects: A. S. Morgan et al., Cancer Res. 58, 2568 (1998). Clinical pharmacokinetics and toxicology in advanced solid malignancies: L. S. Rosen et al., Clin. Cancer Res. 9, 1628 (2003); idem et al., ibid. 10, 3689 (2004).

Chemical structure

Properties

White solid, mp 82-90°.

Derivative

Hydrochloride.

Nomenclature

CAS number: 439943-59-6
TLK-286; Telcyta (Telik).
C26H40Cl4N5O10PS.HCl; mol wt 823.94.
C 37.90%, H 5.02%, Cl 21.51%, N 8.50%, O 19.42%, P 3.76%, S 3.89%.

Therapeutic Category

Antineoplastic.

Keywords

Antineoplastic; Alkylating Agents; Nitrogen Mustards