Stibophen

Stibophen
Clinical data

ATC code	P02BX03 (WHO)
Identifiers
IUPAC name Pentasodium 2-(2-oxido-3,5-disulfonatophenoxy)-1,3,2-benzodioxastibole-5,7-disulfonate
CAS Number	23940-36-5
PubChem (CID)	16683091
ECHA InfoCard	100.041.752
Chemical and physical data
Formula	C₁₂H₄Na₅O₁₆S₄Sb
Molar mass	769.12 g/mol
3D model (Jmol)	Interactive image
SMILES C1=C(C=C2C(=C1S(=O)(=O)[O-])O[Sb](O2)OC3=CC(=CC(=C3[O-])S(=O)(=O)[O-])S(=O)(=O)[O-])S(=O)(=O)[O-].[Na+].[Na+].[Na+].[Na+].[Na+]
(verify)

Stibophen is an anthelmintic classified as antimony compound and used as treatment of schistosomiasis^[1] by intramuscular injection.

Mechanism of action

Stibophen inhibits the enzyme phosphofructokinase, which the worms need for glycolysis,^[2] at least partly by binding to the sulfhydryl (–SH) group of the enzyme.^[3] Inhibiting glycolysis paralyzes the worms, which lose their hold on the wall of mesenteric veins and undergo hepatic shift, die, and are phagocytosed by liver cells.

References

↑ Miller, M. J.; Lyon, H. P. (1955). "Treatment of vesical schistosomiasis with stibophen". The American journal of tropical medicine and hygiene. 4 (6): 1049–1056. PMID 13268811.
↑ Bueding, E.; Mansour, J. M. (1957). "The relationship between inhibition of phosphofructokinase activity and the mode of action of trivalent organic antimonials on Schistosoma mansoni". British journal of pharmacology and chemotherapy. 12 (2): 159–165. PMC 1509678. PMID 13446367.
↑ Su, J. G.; Mansour, J. M.; Mansour, T. E. (1996). "Purification, kinetics and inhibition by antimonials of recombinant phosphofructokinase from Schistosoma mansoni". Molecular and biochemical parasitology. 81 (2): 171–178. doi:10.1016/0166-6851(96)02702-8. PMID 8898332.

Antiparasitics – Anthelmintics (P02) and Endectocides (QP54)

Antiplatyhelmintic agents

Antitrematodals
(schistosomicides)

Binds tubulin	benzimidazole Triclabendazole^#

AI	phosphonic acid Metrifonate^‡

Other/unknown	quinoline Praziquantel^# Oxamniquine^# phenol Bithionol thiazole Niridazole arylsulfonate Stibophen

Anticestodals
(taeniacides)

Binds tubulin	benzimidazole Albendazole^#

Other/unknown	quinoline Praziquantel^# salicylanilide Niclosamide^# aminoacridine Quinacrine butyrophenone Desaspidin chlorophenol Dichlorophen

Antinematodal agents
(including
macrofilaricides)

Binds tubulin	benzimidazole Mebendazole^# Albendazole^# Tiabendazole Fenbendazole Ciclobendazole Flubendazole

Glutamate-gated chloride channel, GABA receptor	avermectins Abamectin Doramectin Emamectin Ivermectin^# Selamectin milbemycins Moxidectin Milbemycin oxime

NMDA	tetrahydropyrimidine Pyrantel^# pyrantel pamoate Oxantel Morantel Carbantel Febantel (aka felsantel)

Other/unknown	piperazine Piperazine Diethylcarbamazine^# thiazole Levamisole^# quinolinium Pyrvinium benzylammonium Bephenium naphthalenesulfonate Suramin^# Tribendimidine

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

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