9006. Suramin Sodium

Nomenclature

CAS number: 129-46-4
8,8′-[Carbonylbis[imino-3,1-phenylenecarbonylimino(4-methyl-3,1-phenylene)carbonylimino]]bis-1,3,5-naphthalenetrisulfonic acid sodium salt (1:6); hexasodium sym-bis(m-aminobenzoyl-m-amino-p-methylbenzoyl-1-naphthylamino-4,6,8-trisulfonate) carbamide; Bayer 205; Fourneau 309; Antrypol (AstraZeneca); Germanin (Bayer); Naganol.
C51H34N6Na6O23S6; mol wt 1429.17.
C 42.86%, H 2.40%, N 5.88%, Na 9.65%, O 25.75%, S 13.46%.

Description and references

Trypanocide discovered in 1917 by O. Dressel and R. Kothe: J. Dressel, J. Chem. Educ. 38, 620 (1961). Prepn: E. Fourneau et al., Compt. Rend. 178, 675 (1924); J. Trefouel, E. Fourneau, GB 224849 (1923); B. Heymann, Angew. Chem. 37, 585 (1924). Pharmacology, toxicology, and efficacy in onchocerciasis and trypanosomiasis: F. Hawking, Adv. Pharmacol. Chemother. 15, 289-322 (1978). Inhibition of reverse transcriptase: E. De Clercq, Cancer Lett. 8, 9 (1979); of infectivity of HIV: H. Mitsuya et al., Science 226, 172 (1984). HPLC determn in plasma: R. W. Klecker, J. M. Collins, J. Liq. Chromatogr. 8, 1685 (1985). Review of biological activities and clinical experience in infection and carcinoma: T. E. Voogd et al., Pharmacol. Rev. 45, 177-203 (1993); C. A. Stein, Cancer Res. 53, 2239-2248 (1993).

Chemical structure

Properties

White or slightly pink or cream-colored powder. Slightly bitter taste. Hygroscopic. Freely sol in water, in physiological saline; sparingly sol in 95% alcohol. Insol in benzene, ether, petr ether, chloroform. Aq solns are neutral to litmus. LD50 in mice (mg/kg): ≈620 i.v. (Hawking).

Therapeutic Category

Anthelmintic (Nematodes); antiprotozoal (Trypanosoma).

Therapeutic Category (Veterinary)

Antiprotozoal (Trypanosoma).

Keywords

Anthelmintic (Nematodes); Antiprotozoal (Trypanosoma)