Page last updated: 2024-09-22

iprindole

Description

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

ExcerptReference
"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."( Goodwin, FK; Zis, AP, 1979)

Treatment

ExcerptReference
"Iprindole pretreatment increased drug levels in brain and prolonged the half-lives by two- to threefold."( Baker, JC; Fuller, RW; Molloy, BB, 1977)
"Rats treated with iprindole (IPR) (10 mg/kg, i.p.) were given a single dose (15 mg/kg, i.p.) of amphetamine (AMP). "( Gibb, JW; Peat, MA; Warren, PF, 1984)
"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."( Baker, GB; Coutts, RT; Dewhurst, WG; Hegadoren, KM, 1991)

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]

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]

Research Highlights

Safety/Toxicity (3)

ArticleYear
Effects of 2-deoxy-D-glucose on methamphetamine-induced dopamine and serotonin neurotoxicity.
Journal of neurochemistry, Volume: 70, Issue: 1
1998
Long-lasting dopamine receptor up-regulation in amphetamine-treated rats following amphetamine neurotoxicity.
Pharmacology, biochemistry, and behavior, Volume: 40, Issue: 4
1991
Protection against amphetamine-induced neurotoxicity toward striatal dopamine neurons in rodents by LY274614, an excitatory amino acid antagonist.
Neuropharmacology, Volume: 31, Issue: 10
1992
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Long-term Use (17)

ArticleYear
Experimental lipidosis of the inner ear.
Archives of oto-rhino-laryngology, Volume: 229, Issue: 3-4
1980
Differential actions of mianserin and iprindole on the sensitivity of cortical neurons to noradrenaline: effect of chronic treatment.
European journal of pharmacology, Jul-10, Volume: 72, Issue: 4
1981
Atypical antidepressant drugs - psychopharmacological profile and mechanism of action.
Pharmacopsychiatria, Volume: 15, Issue: 1
1982
Changes in amphetamine-induced anorexia and stereotypy during chronic treatment with antidepressant drugs.
European journal of pharmacology, Mar-02, Volume: 98, Issue: 3-4
1984
Antidepressant drugs with varying pharmacological profiles alter rat pineal beta adrenergic-mediated function.
The Journal of pharmacology and experimental therapeutics, Volume: 228, Issue: 3
1984
Sensitivity in vivo of central alpha 2- and opiate receptors after chronic treatment with various antidepressants.
Journal of neural transmission, Volume: 54, Issue: 1-2
1982
Role of neuronal signal input in the down-regulation of central noradrenergic receptor function by antidepressant drugs.
Journal of neurochemistry, Volume: 39, Issue: 1
1982
Alpha 2-adrenoreceptors on human platelets: selective labelling by [3H]clonidine and [3H]yohimbine and competitive inhibition by antidepressant drugs.
European journal of pharmacology, Sep-24, Volume: 74, Issue: 4
1981
Brain monoamine oxidase activity after in vivo-chronic iprindole treatment.
Pharmacology, biochemistry, and behavior, Volume: 15, Issue: 6
1981
Effects of antidepressant drugs on the behavior of olfactory bulbectomized and sham-operated rats.
Behavioral neuroscience, Volume: 100, Issue: 2
1986
The effects of imipramine and iprindole on the metabolism of octopamine in the rat.
Neuropharmacology, Volume: 24, Issue: 8
1985
Regulation of high- and low-affinity [3H]imipramine recognition sites in rat brain by chronic treatment with antidepressants.
European journal of pharmacology, Jun-19, Volume: 138, Issue: 2
1987
Chronic antidepressant treatment reduces central beta-adrenoceptor sensitivity in a behavioural test.
European journal of pharmacology, Aug-07, Volume: 127, Issue: 1-2
1986
Agonist interactions with beta-adrenergic receptors following chronic administration of desipramine or the atypical antidepressants, iprindole and mianserin.
Journal of receptor research, Volume: 5, Issue: 5-6
1985
Chronic electroconvulsive treatment augments coupling of the GTP-binding protein Gs to the catalytic moiety of adenylyl cyclase in a manner similar to that seen with chronic antidepressant drugs.
Journal of neurochemistry, Volume: 56, Issue: 1
1991
A possible common mechanism of action of antidepressant treatments: reduction in the sensitivity of the noradrenergic cyclic AMP gererating system in the rat limbic forebrain.
Naunyn-Schmiedeberg's archives of pharmacology, Volume: 293, Issue: 2
1976
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Dosage (4)

ArticleYear
3H-mepyramine binding in various regions of rat brain following chronic treatment with different classes of antidepressant drugs.
Progress in neuro-psychopharmacology & biological psychiatry, Volume: 6, Issue: 4-6
1982
Brain monoamine oxidase activity after in vivo-chronic iprindole treatment.
Pharmacology, biochemistry, and behavior, Volume: 15, Issue: 6
1981
5-Hydroxytryptamine-stimulated inositol phospholipid hydrolysis in rat cerebral cortex slices: pharmacological characterization and effects of antidepressants.
The Journal of pharmacology and experimental therapeutics, Volume: 233, Issue: 2
1985
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]