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Details

Stereochemistry ABSOLUTE
Molecular Formula C17H18ClN3
Molecular Weight 299.798
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LERGOTRILE

SMILES

[H][C@@]12CC3=C(Cl)NC4=CC=CC(=C34)[C@@]1([H])C[C@@H](CC#N)CN2C

InChI

InChIKey=JKAHWGPTNVUTNB-IXPVHAAZSA-N
InChI=1S/C17H18ClN3/c1-21-9-10(5-6-19)7-12-11-3-2-4-14-16(11)13(8-15(12)21)17(18)20-14/h2-4,10,12,15,20H,5,7-9H2,1H3/t10-,12-,15-/m1/s1

HIDE SMILES / InChI

Molecular Formula C17H18ClN3
Molecular Weight 299.798
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Lergotrile is an ergot alkaloid clinically effective in the treatment of Parkinson’s disease. The in vivo dopaminergic effects of lergotrile are similar to those produced by the direct acting dopaminergic agonists apomorphine or L-DOPA. Like apomorphine or L-DOPA, lergotrile decreases prolactin secretion, produces stereotyped behavior in intact rats, and causes contralateral rotation in rats with uniIateral 6-hydroxydopamine lesions of substantia nigra. However, unlike apomorphine or L-DOPA, lergotrile does not activate dopamine sensitive adenylate cyclase in vitro. Side effects of lergotrile included exacerbation of hallucinations, dyskinesias, hypotension, and alterations in liver function tests. Although lergotrile, when added to levodopa, has a definite antiparkinsonian effect, the incidence of adverse effects, particularly hepatotoxicity, makes it unlikely that this ergot alkaloid will become widely available for the treatment of Parkinson’s disease.

Approval Year

PubMed

PubMed

TitleDatePubMed
Lergotrile in the treatment of parkinsonism.
1978 Jul
Dopaminergic effects of lergotrile: possible involvement of a metabolite.
1980 Jun
Clinical pharmacokinetics of ergotamine, dihydroergotamine, ergotoxine, bromocriptine, methysergide, and lergotrile.
1983 Mar
Interactions of neurotensin with brain dopamine systems: biochemical and behavioral studies.
1983 May
Psychiatric disorders in parkinsonism: 2. Organic cerebral states and drug reactions.
1986 Mar
Aminergic regulation of neuroendocrinological functions: theoretical background and some clinical examples.
1987
D-1 and D-2 agonists in Parkinson's disease.
1987 Aug
Stimulus properties of dopaminergic drugs: comparisons involving selective agonists and antagonists.
1988
Cloning and expression of a novel serotonin receptor with high affinity for tricyclic psychotropic drugs.
1993 Mar

Sample Use Guides

Single dose - 0.05 - 1.5 mg/kg
Route of Administration: Intraperitoneal
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:39:22 UTC 2023
Edited
by admin
on Fri Dec 15 16:39:22 UTC 2023
Record UNII
O68JXU1W09
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LERGOTRILE
INN   USAN  
INN   USAN  
Official Name English
LERGOTRILE [USAN]
Common Name English
lergotrile [INN]
Common Name English
2-Chloro-6-methylergoline-8β-acetonitrile
Systematic Name English
ERGOLINE-8-ACETONITRILE, 2-CHLORO-6-METHYL-, (8.BETA.)-
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C66884
Created by admin on Fri Dec 15 16:39:22 UTC 2023 , Edited by admin on Fri Dec 15 16:39:22 UTC 2023
Code System Code Type Description
INN
3594
Created by admin on Fri Dec 15 16:39:22 UTC 2023 , Edited by admin on Fri Dec 15 16:39:22 UTC 2023
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FDA UNII
O68JXU1W09
Created by admin on Fri Dec 15 16:39:22 UTC 2023 , Edited by admin on Fri Dec 15 16:39:22 UTC 2023
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MESH
C031875
Created by admin on Fri Dec 15 16:39:22 UTC 2023 , Edited by admin on Fri Dec 15 16:39:22 UTC 2023
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WIKIPEDIA
Lergotrile
Created by admin on Fri Dec 15 16:39:22 UTC 2023 , Edited by admin on Fri Dec 15 16:39:22 UTC 2023
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EPA CompTox
DTXSID701043282
Created by admin on Fri Dec 15 16:39:22 UTC 2023 , Edited by admin on Fri Dec 15 16:39:22 UTC 2023
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SMS_ID
100000082591
Created by admin on Fri Dec 15 16:39:22 UTC 2023 , Edited by admin on Fri Dec 15 16:39:22 UTC 2023
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ChEMBL
CHEMBL80937
Created by admin on Fri Dec 15 16:39:22 UTC 2023 , Edited by admin on Fri Dec 15 16:39:22 UTC 2023
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EVMPD
SUB08438MIG
Created by admin on Fri Dec 15 16:39:22 UTC 2023 , Edited by admin on Fri Dec 15 16:39:22 UTC 2023
PRIMARY
PUBCHEM
6918447
Created by admin on Fri Dec 15 16:39:22 UTC 2023 , Edited by admin on Fri Dec 15 16:39:22 UTC 2023
PRIMARY
CAS
36945-03-6
Created by admin on Fri Dec 15 16:39:22 UTC 2023 , Edited by admin on Fri Dec 15 16:39:22 UTC 2023
PRIMARY
NCI_THESAURUS
C81079
Created by admin on Fri Dec 15 16:39:22 UTC 2023 , Edited by admin on Fri Dec 15 16:39:22 UTC 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY