9463. Tirilazad

Nomenclature

CAS number: 110101-66-1
(16α)-21-[4-(2,6-Di-1-pyrrolidinyl-4-pyrimidinyl)-1-piperazinyl]-16-methylpregna-1,4,-9(11)-triene-3,20-dione.
C38H52N6O2; mol wt 624.86.
C 73.04%, H 8.39%, N 13.45%, O 5.12%.

Description and references

Member of a novel class of nonglucocorticoid, 21-aminosteroid antioxidants known as lazaroids which inhibit lipid peroxidation and have cytoprotectant activity. Prepn: J. M. McCall et al., WO 8701706; eidem, US 5175281 (1987, 1992 both to Upjohn). Inhibition of iron-dependent lipid peroxidation in vitro: J. M. Braughler et al., J. Biol. Chem. 262, 10438 (1987). HPLC determn in plasma: J. W. Cox, R. H. Pullen, J. Chromatogr. 424, 293 (1988). Clinical pharmacokinetics: J. C. Fleishaker et al., J. Clin. Pharmacol. 33, 175, 182 (1993). Veterinary evaluation in endotoxemia of neonatal calves: M. L. Rose, S. D. Semrad, Am. J. Vet. Res. 53, 2305 (1992). Review: E. D. Hall, Ann. Neurol. 32, S137-S142 (1992). Review of efficacy and mechanism of action in experimental models of subarachnoid hemorrhage: idem, Eur. J. Anaesthesiol. 13, 279-289 (1996); of clinical trials in acute ischemic stroke: Tirilazad International Steering Committee, Stroke 32, 2257-2265 (2000).

Chemical structure

Derivative

Methanesulfonate monohydrate.

Nomenclature

CAS number: 111793-42-1
Tirilazad mesylate; U-74006F; Freedox (Pharmacia & Upjohn).
C38H52N6O2.CH3SO3H.H2O; mol wt 738.98.
C 63.39%, H 7.91%, N 11.37%, O 12.99%, S 4.34%.

Properties

mp 181-185° (dec). uv max: 234, 285 nm (ε 52000, 17000). Log P (octanol/water): 8.