4901. Iloprost

Nomenclature

CAS number: 78919-13-8
5-[(3aS,4R,5R,6aS)-Hexahydro-5-hydroxy-4-[(1E,3S)-3-hydroxy-4-methyl-1-octen-6-ynyl]-2(1H)-pentalenylidene]pentanoic acid; 5-(E)-(1S,5S,6R,7R)-7-hydroxy-6-[(E)-(3S,4RS)-3-hydroxy-4-methyl-1-octenyl]bicyclo[3.3.0]octan-3-ylidenepentanoic acid; (E)-(3aS,4R,5R,6aS)-hexahydro-5-hydroxy-4-[(E)-(3S,4RS)-3-hydroxy-4-methyl-1-octen-6-ynyl]-Δ2(1H),δ-pentalenevaleric acid; ciloprost; ZK-36374.
C22H32O4; mol wt 360.49.
C 73.30%, H 8.95%, O 17.75%.

Description and references

Prostacyclin analog; 1:1 mixture of 16α- and 16β-methyl diastereomers. Prepn: W. Skuballa et al., DE 2845770; eidem, US 4692464 (1980, 1987 both to Schering AG); W. Skuballa, H. Vorbrüggen, Adv. Prostaglandin Thromboxane Leukotriene Res. 11, 299 (1983). Antithrombotic and cardiovascular pharmacology: K. Schrr et al., Arch. Pharmacol. 316, 252 (1981). Review of clinical pharmacology and pharmacokinetics: S. M. Grant, K. L. Goa, Drugs 43, 889-924 (1992). Clinical study in limb ischemia: J. Dormandy, Therapie 46, 319 (1991); in Raynaud phenomenon: F. M. Wigley et al., Ann. Intern. Med. 120, 199 (1994); in pulmonary hypertension: H. Olschewski et al., N. Engl. J. Med. 347, 322 (2002).

Chemical structure

Properties

Colorless oil.

Derivative

Tromethamine.

Nomenclature

CAS number: 697225-02-8
Endoprost (Italfarmaco); Ilomedin (Schering AG); Ventavis (Schering AG).
C22H32O4.C4H11NO3; mol wt 481.62.
C 64.84%, H 9.00%, O 23.25%, N 2.91%.

Therapeutic Category

Vasodilator (peripheral). In treatment of pulmonary hypertension.

Keywords

Vasodilator (Peripheral)