9586. Treprostinil

Nomenclature

CAS number: 81846-19-7
[[(1R,2R,3aS,9aS)-2,3,3a,4,9,9a-Hexahydro-2-hydroxy-1-[(3S)-3-hydroxyoctyl]-1H-benz[f]inden-5-yl]oxy]acetic acid; 9-deoxy-2′,9α-methano-3-oxa-4,5,6-trinor-3,7-(1′,3′-interphenylene)-13,14-dihydroprostaglandin F1.
C23H34O5; mol wt 390.51.
C 70.74%, H 8.78%, O 20.49%.

Description and references

Synthetic analog of prostacyclin, q.v. Prepn: P. A. Aristoff et al., GB 2070596; idem, US 4306075 (both 1981 to Upjohn). Pharmacology: R. P. Steffen, M. de la Mata, Prostaglandins Leukotrienes Essent. Fatty Acids 43, 277 (1991). Pharmacokinetics: M. J. McNulty et al., ibid. 159; of intravenous and subcutaneous administration: K. Laliberte et al., J. Cardiovasc. Pharmacol. 44, 209 (2004). RIA determn in plasma: J. W. A. Findlay et al., ibid. 167. Clinical study in pulmonary arterial hypertension: G. Simonneau et al., Am. J. Respir. Crit. Care Med. 165, 800 (2002); by s. c. infusion: R. J. Oudiz et al., Chest 126, 420 (2004); by continuous i.v.: V. F. Tapson et al., ibid. 129, 683 (2006).

Chemical structure

Properties

Crystals from ethyl acetate in hexane, mp 121-123°.

Derivative

Sodium salt.

Nomenclature

CAS number: 289480-64-4
15AU81; BW15AU; U-62840; UT-15; Remodulin (United Ther.).
C23H33NaO5; mol wt 412.49.
C 66.97%, H 8.06%, Na 5.57%, O 19.39%.

Therapeutic Category

Antihypertensive.

Keywords

Antihypertensive