Carbodithioic acid esters of fluoxetine, a novel class of dual-function spermicides.
Carbodithioic acid esters of fluoxetine have been prepared by replacing the methylamino function in aminopropane chain with carbodithioic acid ester group and by adding various S-2-hydroxypropyl ester of dialkyl carbodithioic acid at 3-methylamino group. Some of these compounds showed spermicidal, antifungal and anti-Trichomonas activities. The study revealed that incorporation of carbodithioic acid residue directly into fluoxetine structure leads to compounds with better antifungal and anti-Trichomonas activities, and N-methyl-[3-phenyl-3-(4-trifluoromethyl-phenoxy)-propyl]carbodithioic acid S-(2-pyrrolidino-ethyl) ester (14) has shown better profile than both fluoxetine and nonoxynol-9. Further lead optimization may yield a potent dual-function spermicide.
Division of Medicinal and Process Chemistry, Central Drug Research Institute, Lucknow-226001, Uttar Pradesh, India.
S T V S
ST
Kiran Kumar
Lalit
L
Kumar
Vishnu L
VL
Sharma
Ashish
A
Jain
Rajeev K
RK
Jain
Jagdamba P
JP
Maikhuri
Manish
M
Kumar
Praveen K
PK
Shukla
Gopal
G
Gupta
D000818:Animals; D004952:Esters / Q000737:chemistry* / Q000494:pharmacology*; D005473:Fluoxetine / Q000737:chemistry*; D005658:Fungi / Q000187:drug effects; D013089:Spermatocidal Agents / Q000737:chemistry* / Q000494:pharmacology*; D014246:Trichomonas vaginalis / Q000187:drug effects
D004952:Esters; D013089:Spermatocidal Agents; D005473:Fluoxetine