Page last updated: 2024-12-06

iprindole

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

Iprindole is a tetracyclic antidepressant that was originally developed in the 1960s. It is a non-selective serotonin reuptake inhibitor (SSRI) that also has some anticholinergic activity. Iprindole is thought to exert its antidepressant effects by increasing serotonin levels in the brain. It is not widely used today, but it remains a valuable tool for research into the mechanisms of action of antidepressants. Iprindole has been studied for its effects on a variety of conditions, including depression, anxiety, and obsessive-compulsive disorder. It is also being investigated for its potential use in the treatment of Alzheimer's disease. Iprindole is synthesized in a multi-step process that involves the reaction of various organic compounds. The exact synthesis process is complex and proprietary information.'

Iprindole: A tricyclic antidepressant that has actions and uses similar to those of AMITRIPTYLINE, but has only weak antimuscarinic and sedative effects. (From Martindale, The Extra Pharmacopoeia, 30th ed, p257) [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID21722
CHEMBL ID126224
CHEBI ID135177
SCHEMBL ID49509
MeSH IDM0011703

Synonyms (71)

Synonym
tertran
5h-cyclooct[b]indole,7,8,9,10,11-hexahydro-
prondol
5h-cyclooct[b]indole,7,8,9,10,11-hexahydro-5-(3-dimethylaminopropyl)-
nsc-169449
galatur
wln: t b658 hn&&tj h3n1&1
wln: t c658 bn&&tj b3n1&1
pramindole
nsc169449
5h-cyclooct[b]indole-5-propanamine,7,8,9,10,11,hexahydro-n,n-dimethyl-
5h-cyclooct[b]indole-5-propanamine,7,8,9,10,11-hexahydro-n,n-dimethyl-
iprindole
1-(3-dimethylaminopropyl)-2,3-hexamethyleneindole
5560-72-5
5-[3-(dimethylamino)propyl]-6,8,9,10,11-hexahydro-5h-cyclooct[b]indole
wy-3263
5h-cyclooct[b]indole-5-propanamine, 6,7,8,9,10,11-hexahydro-n,n-dimethyl-
iprindolum [inn-latin]
nsc 169449
einecs 226-933-5
brn 1386299
wy-3263 (van)
5h-cyclooct(b)indole-5-propanamine, 6,7,8,9,10,11-hexahydro-n,n-dimethyl-
5-(3-(dimethylamino)propyl)-6,7,8,9,10,11-hexahydro-5h-cyclooct(b)indole
iprindol [inn-spanish]
5h-cyclooct(b)indole, 5-(3-(dimethylamino)propyl)-6,7,8,9,10,11-hexahydro-
PDSP1_001610
{5h-cyclooct[b]indole,} {5-[3-(dimethylamino)propyl]-6,7,8,9,10,11-hexahydro-}
{5-[3-(dimethylamino)propyl]-6,7,8,9,10,} {11-hexahydro-5h-cyclooct[b]indole}
3-(6,7,8,9,10,11-hexahydrocycloocta[b]indol-5-yl)-n,n-dimethyl-propan-1-amine
3-(6,7,8,9,10,11-hexahydro-5h-cycloocta[b]indol-5-yl)-n,n-dimethyl-1-propanamine
{5h-cyclooct[b]indole-5-propanamine,} 6,7,8,9,10,11-hexahydro-n, n-dimethyl-
n-(3-(6,7,8,9,10,11-hexahydro-5h-cycloocta[b]indol-5-yl)propyl)-n,n-dimethylamine
{5h-cyclooct[b]indole-5-propanamine,} 6,7,8,9,10, 11,hexahydro-n,n-dimethyl-
{5h-cyclooct[b]indole,} 6,7,8,9,10, 11-hexahydro-5-(3-dimethylaminopropyl)-
iprindole (usan/inn)
D04605
PDSP2_001594
OPREA1_812073
CHEBI:135177
L001038
CHEMBL126224
3-(6,7,8,9,10,11-hexahydrocycloocta[b]indol-5-yl)-n,n-dimethylpropan-1-amine
cas_5560-72-5
nsc_21722
bdbm81448
iprindol
69u0ikr8fp ,
iprindole [usan:inn:ban]
iprindolum
unii-69u0ikr8fp
iprindole [inn]
iprindole [usan]
iprindole [who-dd]
5-[3-(dimethylamino)propyl]-6,7,8,9,10,11-hexahydro-5h-cyclooct[b]indole
iprindole [mi]
SCHEMBL49509
5h-cyclooct(b)indole, 6,7,8,9,10,11-hexahydro-5-(3-dimethylaminopropyl)-
PLIGPBGDXASWPX-UHFFFAOYSA-N
n-[3-(6,7,8,9,10,11-hexahydro-5h-cycloocta[b]indol-5-yl)propyl]-n,n-dimethylamine #
DTXSID80204145
CS-0011246
HY-12392
DB13496
Q904673
chloraminettrihydrate
5h-cyclooct[b]indole, 5-[3-(dimethylamino)propyl]-6,7,8,9,10,11-hexahydro- (8ci); 5-[3-(dimethylamino)propyl]-6,7,8,9,10,11-hexahydro-5h-cyclooct[b]indole; nsc 169449; pramindole; tertran
MS-24057
(3-{5h,6h,7h,8h,9h,10h,11h-cycloocta[b]indol-5-yl}propyl)dimethylamine
AKOS040755577

Research Excerpts

Overview

Iprindole is a relatively weak inhibitor of both norepinephrine (NE) and serotonin, whereas mianserin possesses at least modest potency as an inhibitor of NE uptake.

ExcerptReferenceRelevance
"Iprindole is an active antidepressant in clinical practice but its mechanism of action has never been clearly defined. "( [Iprindole: a functional link between serotonin and noradrenaline systems?].
Bourin, M; Ganry, H,
)
2.48
"Iprindole is a relatively weak inhibitor of both norepinephrine (NE) and serotonin, whereas mianserin possesses at least modest potency as an inhibitor of NE uptake."( Novel antidepressants and the biogenic amine hypothesis of depression. The case for iprindole and mianserin.
Goodwin, FK; Zis, AP, 1979
)
1.21

Treatment

Iprindole pretreatment increased drug levels in brain and prolonged the half-lives by two- to threefold. Pretreatment with iprindole led to an increase inbrain and liver levels of fenfluramine.

ExcerptReferenceRelevance
"Iprindole pretreatment increased drug levels in brain and prolonged the half-lives by two- to threefold."( Biological disposition of rigid analogs of amphetamine.
Baker, JC; Fuller, RW; Molloy, BB, 1977
)
0.98
"Rats treated with iprindole (IPR) (10 mg/kg, i.p.) were given a single dose (15 mg/kg, i.p.) of amphetamine (AMP). "( The effects of a single dose of amphetamine and iprindole on the serotonergic system of the rat brain.
Gibb, JW; Peat, MA; Warren, PF, 1984
)
0.86
"Pretreatment with iprindole led to an increase in brain and liver levels of fenfluramine, and, unexpectedly, to a marked decrease in levels of norfenfluramine in these tissues."( Interactions of iprindole with fenfluramine metabolism in rat brain and liver.
Baker, GB; Coutts, RT; Dewhurst, WG; Hegadoren, KM, 1991
)
0.95

Toxicity

ExcerptReferenceRelevance
" METH's toxic effects on brain 5-HT neurons were either unaffected or exacerbated by 2-DG, depending on species, brain region, and dose of METH tested."( Effects of 2-deoxy-D-glucose on methamphetamine-induced dopamine and serotonin neurotoxicity.
Callahan, B; Hatzidimitriou, G; Ricaurte, G; Stover, G; Yuan, J, 1998
)
0.3

Dosage Studied

ExcerptRelevanceReference
" 5-HT agonists stimulated [3H]inositol phosphate accumulation in a dose-related but biphasic manner and only the high-affinity component of the dose-response curve was sensitive to antagonists."( 5-Hydroxytryptamine-stimulated inositol phospholipid hydrolysis in rat cerebral cortex slices: pharmacological characterization and effects of antidepressants.
Kendall, DA; Nahorski, SR, 1985
)
0.27
" The treatment inhibited mitochondrial monoamine oxidase activity of all three brain regions studied, although a dose-response inhibitory effect was found only in the mesencephalon."( Brain monoamine oxidase activity after in vivo-chronic iprindole treatment.
Carranza, J; Castro-Osuna, G; Esparza-Avalos, NS; Guzmán-Amaya, P; Ortega-Corona, BG; Sosa, A, 1981
)
0.51
" Administration of chlorimipramine in clinical dosage caused a complete disappearance of the 3H-mepyramine affinity for its receptor in the occipital cortex."( 3H-mepyramine binding in various regions of rat brain following chronic treatment with different classes of antidepressant drugs.
Dupont, A; Merand, Y; Savard, P, 1982
)
0.26
" Depending on the intended indication and dosing regimen, PPL can delay or stop development of a compound in the drug discovery process."( Evaluation of a published in silico model and construction of a novel Bayesian model for predicting phospholipidosis inducing potential.
Gehlhaar, D; Greene, N; Johnson, TO; Pelletier, DJ; Tilloy-Ellul, A,
)
0.13
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
indolesAny compound containing an indole skeleton.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Bioassays (24)

Assay IDTitleYearJournalArticle
AID1079939Cirrhosis, proven histopathologically. Value is number of references indexed. [column 'CIRRH' in source]
AID588220Literature-mined public compounds from Kruhlak et al phospholipidosis modelling dataset2008Toxicology mechanisms and methods, , Volume: 18, Issue:2-3
Development of a phospholipidosis database and predictive quantitative structure-activity relationship (QSAR) models.
AID1079946Presence of at least one case with successful reintroduction. [column 'REINT' in source]
AID1079936Choleostatic liver toxicity, either proven histopathologically or where the ratio of maximal ALT or AST activity above normal to that of Alkaline Phosphatase is < 2 (see ACUTE). Value is number of references indexed. [column 'CHOLE' in source]
AID1079948Times to onset, minimal and maximal, observed in the indexed observations. [column 'DELAI' in source]
AID1079949Proposed mechanism(s) of liver damage. [column 'MEC' in source]
AID1079938Chronic liver disease either proven histopathologically, or through a chonic elevation of serum amino-transferase activity after 6 months. Value is number of references indexed. [column 'CHRON' in source]
AID1079947Comments (NB not yet translated). [column 'COMMENTAIRES' in source]
AID1079941Liver damage due to vascular disease: peliosis hepatitis, hepatic veno-occlusive disease, Budd-Chiari syndrome. Value is number of references indexed. [column 'VASC' in source]
AID1079937Severe hepatitis, defined as possibly life-threatening liver failure or through clinical observations. Value is number of references indexed. [column 'MASS' in source]
AID588208Literature-mined public compounds from Lowe et al phospholipidosis modelling dataset2010Molecular pharmaceutics, Oct-04, Volume: 7, Issue:5
Predicting phospholipidosis using machine learning.
AID1079943Malignant tumor, proven histopathologically. Value is number of references indexed. [column 'T.MAL' in source]
AID1079934Highest frequency of acute liver toxicity observed during clinical trials, expressed as a percentage. [column '% AIGUE' in source]
AID540237Phospholipidosis-positive literature compound observed in rat
AID1079931Moderate liver toxicity, defined via clinical-chemistry results: ALT or AST serum activity 6 times the normal upper limit (N) or alkaline phosphatase serum activity of 1.7 N. Value is number of references indexed. [column 'BIOL' in source]
AID1079935Cytolytic liver toxicity, either proven histopathologically or where the ratio of maximal ALT or AST activity above normal to that of Alkaline Phosphatase is > 5 (see ACUTE). Value is number of references indexed. [column 'CYTOL' in source]
AID1079940Granulomatous liver disease, proven histopathologically. Value is number of references indexed. [column 'GRAN' in source]
AID1079932Highest frequency of moderate liver toxicity observed during clinical trials, expressed as a percentage. [column '% BIOL' in source]
AID1079933Acute liver toxicity defined via clinical observations and clear clinical-chemistry results: serum ALT or AST activity > 6 N or serum alkaline phosphatases activity > 1.7 N. This category includes cytolytic, choleostatic and mixed liver toxicity. Value is
AID205268Inhibition of binding of Batrachotoxinin [3H]BTX-B to high affinity sites on voltage dependent sodium channels in a vesicular preparation from guinea pig cerebral cortex at 10 uM1985Journal of medicinal chemistry, Mar, Volume: 28, Issue:3
[3H]Batrachotoxinin A 20 alpha-benzoate binding to voltage-sensitive sodium channels: a rapid and quantitative assay for local anesthetic activity in a variety of drugs.
AID1079942Steatosis, proven histopathologically. Value is number of references indexed. [column 'STEAT' in source]
AID643383Induction of phospholipidosis in bovine corneal fibroblasts assessed as lamellar inclusion bodies after 72 hrs by light microscopy2012Journal of medicinal chemistry, Jan-12, Volume: 55, Issue:1
In silico assay for assessing phospholipidosis potential of small druglike molecules: training, validation, and refinement using several data sets.
AID1079944Benign tumor, proven histopathologically. Value is number of references indexed. [column 'T.BEN' in source]
AID1079945Animal toxicity known. [column 'TOXIC' in source]
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (176)

TimeframeStudies, This Drug (%)All Drugs %
pre-1990150 (85.23)18.7374
1990's22 (12.50)18.2507
2000's2 (1.14)29.6817
2010's2 (1.14)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 21.96

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index21.96 (24.57)
Research Supply Index5.26 (2.92)
Research Growth Index3.89 (4.65)
Search Engine Demand Index26.67 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (21.96)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials6 (3.23%)5.53%
Reviews5 (2.69%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other175 (94.09%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]