iprindole iprindole iprindole, sold under the brand names prondol, galatur, and tertran, is an atypical tricyclic antidepressant (tca) that has been used in the united kingdom and ireland for the treatment of depression but appears to no longer be marketed. it was developed by wyeth and was marketed in 1967. the drug has been described by some as the first "second-generation" antidepressant to be introduced. however, it was very little-used compared to other tcas, with the number of prescriptions dispensed only in the thousands. iprindoleclinical datatrade namesprondol, galatur, tertranother namespramindole; wy-3263routes ofadministrationoralatc coden06aa13 (who) legal statuslegal status in general: ℞ (prescription only) pharmacokinetic datametabolismhepaticelimination half-life52.5 hoursexcretionurine, fecesidentifiers iupac name 3-(6,7,8,9,10,11-hexahydro-5h-cyclooctaindol-5-yl)-n,n-dimethylpropan-1-amine cas number5560-72-5 y 20432-64-8 (hydrochloride)pubchem cid21722drugbankdb13496chemspider20417 yunii69u0ikr8fpkeggd04605 ychebichebi:135177chemblchembl126224 ycomptox dashboard (epa)dtxsid80204145 echa infocard100.024.485 chemical and physical dataformulac19h28n2molar mass284.447 g·mol−13d model (jsmol)interactive image smiles c13c(n(c2ccccc12)cccn(c)c)cccccc3 inchi inchi=1s/c19h28n2/c1-20(2)14-9-15-21-18-12-6-4-3-5-10-16(18)17-11-7-8-13-19(17)21/h7-8,11,13h,3-6,9-10,12,14-15h2,1-2h3 ykey:pligpbgdxaswpx-uhfffaoysa-n y (verify) medical uses iprindole was used in the treatment of major depressive disorder in dosages similar to those of other tcas. contraindications iprindole has been associated with jaundice and hepatotoxicity and should not be taken by alcoholics or people with pre-existing liver disease. if such symptoms are encountered iprindole should be discontinued immediately. side effects anticholinergic side effects such as dry mouth and constipation are either greatly reduced in comparison to imipramine and most other tcas or fully lacking with iprindole. however, it still has significant antihistamine effects and therefore can produce sedation, though this is diminished relative to other tcas similarly. iprindole also lacks significant alpha-blocking properties, and hence does not pose a risk of orthostatic hypotension. overdose main article: tricyclic antidepressant overdose in overdose, iprindole is much less toxic than most other tcas and is considered relatively benign. for instance, between 1974 and 1985, only two deaths associated with iprindole were recorded in the united kingdom, whereas 278 were reported for imipramine, although imipramine is used far more often than iprindole. interactions iprindole has been shown to be a potent inhibitor of the aromatic hydroxylation and/or n-dealkylation-mediated metabolism of many substances including, but not limited to octopamine, amphetamine, methamphetamine, fenfluramine, phenelzine, tranylcypromine, trimipramine, and fluoxetine, likely via inactivating cytochrome p450 enzymes. it also inhibits its own metabolism. on account of these interactions, caution should be used when combining iprindole with other drugs. as an example, when administered with amphetamine or methamphetamine, iprindole increases their brain concentrations and prolongs their terminal half-lives by 2- to 3-fold, strongly augmenting both their physiological effects and neurotoxicity in the process. pharmacology pharmacodynamics