Iprindole

Iprindole

Clinical data
Routes of administration	By mouth
ATC code	N06AA13 (WHO)
Legal status
Legal status	In general: ℞ (Prescription only)
Pharmacokinetic data
Metabolism	Hepatic
Biological half-life	52.5 hours
Excretion	Urine, Feces
Identifiers
IUPAC name 3-(6,7,8,9,10,11-Hexahydro- 5H-cycloocta[b]indol-5-yl)-N,N-dimethylpropan-1-amine
CAS Number	5560-72-5 Y
PubChem CID	21722
ChemSpider	20417 Y
UNII	69U0IKR8FP
KEGG	D04605 Y
ChEMBL	CHEMBL126224 Y
ECHA InfoCard	100.024.485
Chemical and physical data
Formula	C19H28N2
Molar mass	284.439 g/mol
3D model (Jmol)	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 Y Key:PLIGPBGDXASWPX-UHFFFAOYSA-N Y

Iprindole (Prondol, Galatur, Tertran), formerly known as pramindole, is a tricyclic antidepressant (TCA) used in Europe for the treatment of depression. It was introduced by Wyeth and has been used clinically since 1967. Notably, iprindole was the first second-generation antidepressant to be launched.

Iprindole is unique compared to most other TCAs in that it is a relatively weak inhibitor of the reuptake of serotonin and norepinephrine and instead acts predominantly as an antagonist of 5-HT₂ receptors, hence its classification as 'second-generation'. Additionally, side effects of iprindole are much less prominent relative to other TCAs and it is well tolerated. However, iprindole's efficacy may not be as great as other TCAs, especially in regards to anxiety relief.

Iprindole has been sold under the trade name Prondol by Wyeth in the United Kingdom and Ireland for the indication of major depressive disorder, and has also been sold as Galatur and Tertran by Wyeth as well.

On a structural level, iprindole differs from other TCAs in that it contains an indole nucleus, similarly to the heterocyclic antipsychotic oxypertine, and has an eight-membered and saturated third ring.