Iprindole

Iprindole
Clinical data
Trade names	Prondol, Galatur, Tertran
Other names	Pramindole; WY-3263
Routes of; administration	Oral
ATC code	N06AA13 (WHO) ;
Legal status
Legal status	In general: ℞ (Prescription only);
Pharmacokinetic data
Metabolism	Hepatic
Elimination 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 ; 20432-64-8 (hydrochloride);
PubChem CID	21722;
DrugBank	DB13496;
ChemSpider	20417 ;
UNII	69U0IKR8FP;
KEGG	D04605 ;
ChEBI	CHEBI:135177;
ChEMBL	ChEMBL126224 ;
CompTox Dashboard (EPA)	DTXSID80204145 ;
ECHA InfoCard	100.024.485
Chemical and physical data
Formula	C19H28N2
Molar mass	284.447 g·mol−1
3D 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 ; Key:PLIGPBGDXASWPX-UHFFFAOYSA-N ;
	(verify)

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.^[4]^[5]^[6]^[7] It was developed by Wyeth and was marketed in 1967.^[8] The drug has been described by some as the first "second-generation" antidepressant to be introduced.^[9] However, it was very little-used compared to other TCAs, with the number of prescriptions dispensed only in the thousands.^[10]

^ Caillé G, de Montigny C, Besner JG (1982). "Quantitation of iprindole in plasma by GLC". Biopharmaceutics & Drug Disposition. 3 (1): 11–17. doi:10.1002/bdd.2510030103. PMID 7082775.
^ Sisenwine SF, Tio CO, Ruelius HW (April 1979). "The disposition of [14C]iprindole in man, dog, miniature swine, rhesus monkey and rat". Xenobiotica; the Fate of Foreign Compounds in Biological Systems. 9 (4): 237–246. doi:10.3109/00498257909038726. PMID 113942.
^ Rotzinger S, Bourin M, Akimoto Y, Coutts RT, Baker GB (August 1999). "Metabolism of some "second"- and "fourth"-generation antidepressants: iprindole, viloxazine, bupropion, mianserin, maprotiline, trazodone, nefazodone, and venlafaxine". Cellular and Molecular Neurobiology. 19 (4): 427–442. doi:10.1023/A:1006953923305. PMID 10379419. S2CID 19585113.
^ Cite error: The named reference IndexNominum2000 was invoked but never defined (see the help page).
^ Ayd FJ (2000). "Iprindole". Lexicon of psychiatry, neurology, and the neurosciences. Philadelphia, Pa: Lippincott-Williams & Wilkins. ISBN 0-7817-2468-6.
^ Dictionary of organic compounds. London: Chapman & Hall. 1996. ISBN 0-412-54090-8.
^ McNeal E, Cimbolic P (1989). "Antidepressant and Biochemical Theories of Depression". In Davison GC, Hooley JM, Neale JM (eds.). Readings in Abnormal Psychology. New York: Wiley. p. 186. ISBN 0-471-63107-8. iprindole.
^ "Jaundice from iprindole (Prondol)". Drug and Therapeutics Bulletin. 9 (3): 10–11. January 1971. doi:10.1136/dtb.9.3.10. PMID 5548547. S2CID 31232918.
^ Horn AS, Trace RC (January 1983). "Second generation antidepressants: The pharmacological and clinical significance of selected examples". Drug Development Research. 3 (3): 203–211. doi:10.1002/ddr.430030302. S2CID 84018071.
^ Aronson JK (2009). "Tricyclic Antidepressants". Meyler's Side Effects of Psychiatric Drugs. Elsevier. pp. 18–. ISBN 978-0-444-53266-4.

[pmid7082775-1] Caillé G, de Montigny C, Besner JG (1982). "Quantitation of iprindole in plasma by GLC". Biopharmaceutics & Drug Disposition. 3 (1): 11–17. doi:10.1002/bdd.2510030103. PMID 7082775.

[pmid113942-2] Sisenwine SF, Tio CO, Ruelius HW (April 1979). "The disposition of [14C]iprindole in man, dog, miniature swine, rhesus monkey and rat". Xenobiotica; the Fate of Foreign Compounds in Biological Systems. 9 (4): 237–246. doi:10.3109/00498257909038726. PMID 113942.

[pmid10379419-3] Rotzinger S, Bourin M, Akimoto Y, Coutts RT, Baker GB (August 1999). "Metabolism of some "second"- and "fourth"-generation antidepressants: iprindole, viloxazine, bupropion, mianserin, maprotiline, trazodone, nefazodone, and venlafaxine". Cellular and Molecular Neurobiology. 19 (4): 427–442. doi:10.1023/A:1006953923305. PMID 10379419. S2CID 19585113.

[IndexNominum2000-4] Cite error: The named reference IndexNominum2000 was invoked but never defined (see the help page).

[isbn0-7817-2468-6-5] Ayd FJ (2000). "Iprindole". Lexicon of psychiatry, neurology, and the neurosciences. Philadelphia, Pa: Lippincott-Williams & Wilkins. ISBN 0-7817-2468-6.

[isbn0-412-54090-8-6] Dictionary of organic compounds. London: Chapman & Hall. 1996. ISBN 0-412-54090-8.

[isbn0-471-63107-8-7] McNeal E, Cimbolic P (1989). "Antidepressant and Biochemical Theories of Depression". In Davison GC, Hooley JM, Neale JM (eds.). Readings in Abnormal Psychology. New York: Wiley. p. 186. ISBN 0-471-63107-8. iprindole.

[pmid5548547-8] "Jaundice from iprindole (Prondol)". Drug and Therapeutics Bulletin. 9 (3): 10–11. January 1971. doi:10.1136/dtb.9.3.10. PMID 5548547. S2CID 31232918.

[doi:10.1002/ddr.430030302-9] Horn AS, Trace RC (January 1983). "Second generation antidepressants: The pharmacological and clinical significance of selected examples". Drug Development Research. 3 (3): 203–211. doi:10.1002/ddr.430030302. S2CID 84018071.

[Aronson2009-10] Aronson JK (2009). "Tricyclic Antidepressants". Meyler's Side Effects of Psychiatric Drugs. Elsevier. pp. 18–. ISBN 978-0-444-53266-4.

[3]

[1]

[2]

[4]

[5]

[6]

[7]

[8]

[9]

[10]