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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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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

Sample Use Guides

In Vivo Use Guide
Single dose - 0.05 - 1.5 mg/kg
Route of Administration: Intraperitoneal
Substance Class Chemical
Record UNII
O68JXU1W09
Record Status Validated (UNII)
Record Version