8467. Sertraline

Nomenclature

CAS number: 79617-96-2
(1S,4S)-4-(3,4-Dichlorophenyl)-1,2,3,4-tetrahydro-N-methyl-1-naphthalenamine.
C17H17Cl2N; mol wt 306.23.
C 66.68%, H 5.60%, Cl 23.15%, N 4.57%.

Description and references

Selective serotonin reuptake inhibitor (SSRI). Prepn: W. M. Welch et al., EP 30081; eidem, US 4536518 (1981, 1985 both to Pfizer); and stereospecific activity: W. M. Welch et al., J. Med. Chem. 27, 1508 (1984). GC determn in plasma: H. G. Fouda et al., J. Chromatogr. 417, 197 (1987). CE determn of stereoisomers: M. X. Zhou, J. P. Foley, J. Chromatogr. A 1052, 13 (2004). Comprehensive description: B. M. Johnson, P.-T. L. Chang, Anal. Profiles Drug Subs. Excip. 24, 443-486 (1996). Review of pharmacology and clinical efficacy in depression and obsessive-compulsive disorder: D. Murdoch, D. McTavish, Drugs 44, 604-624 (1992); of clinical efficacy in post-traumatic stress disorder: A. C. Schwartz, B. O. Rothbaum, Expert Opin. Pharmacother. 3, 1489-1499 (2002); of clinical pharmacokinetics: C. L. DeVane et al., Clin. Pharmacokinet. 41, 1247-1266 (2002).

Chemical structure

Derivative

Hydrochloride.

Nomenclature

CAS number: 79559-97-0
CP-51974-1; Lustral (Pfizer); Zoloft (Pfizer).
C17H17Cl2N.HCl; mol wt 342.69.
C 59.58%, H 5.29%, Cl 31.04%, N 4.09%.

Properties

Crystals, mp 243-245°. [α]D23 +37.9° (c = 2 in methanol). Soly room temp. (mg/ml): water 3.8; 0.1N HCl 0.51; 0.1N NaOH 0.002; ethanol 15.7; isopropyl alcohol 4.3; chloroform 110; acetone 1.1; N,N-dimethylformamide 88; dimethylsulfoxide 147; ethyl acetate 0.20; acetonitrile 0.85; methanolic 0.1N HCl 47; chloroform/methanol (1:1) 134. pKa (water): 9.48 ± 0.04. pKa (methanol:water, 40:60 v/v): 8.6. pKa (ethanol:water, 1:1 v/v): 8.5. d 1.37.

Therapeutic Category

Antidepressant; antiobsessional.

Therapeutic Category (Veterinary)

In treatment of canine and feline behavioral disorders.

Keywords

Antidepressant; Bicyclics; Antiobsessional; Serotonin Uptake Inhibitor