U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C17H18ClN3.CH4O3S
Molecular Weight 395.904
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LERGOTRILE MESYLATE

SMILES

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

InChI

InChIKey=WXHDJVDIJQDJMK-AYJWUPBJSA-N
InChI=1S/C17H18ClN3.CH4O3S/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;1-5(2,3)4/h2-4,10,12,15,20H,5,7-9H2,1H3;1H3,(H,2,3,4)/t10-,12-,15-;/m1./s1

HIDE SMILES / InChI

Molecular Formula CH4O3S
Molecular Weight 96.106
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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 15:14:29 UTC 2023
Edited
by admin
on Fri Dec 15 15:14:29 UTC 2023
Record UNII
1945N48N9E
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LERGOTRILE MESYLATE
USAN  
USAN  
Official Name English
LERGOTRILE MESYLATE [USAN]
Common Name English
LERGOTRILE MESILATE [MART.]
Common Name English
LERGOTRILE MESILATE
MART.  
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C66884
Created by admin on Fri Dec 15 15:14:29 UTC 2023 , Edited by admin on Fri Dec 15 15:14:29 UTC 2023
Code System Code Type Description
ECHA (EC/EINECS)
257-225-4
Created by admin on Fri Dec 15 15:14:29 UTC 2023 , Edited by admin on Fri Dec 15 15:14:29 UTC 2023
PRIMARY
ChEMBL
CHEMBL80937
Created by admin on Fri Dec 15 15:14:29 UTC 2023 , Edited by admin on Fri Dec 15 15:14:29 UTC 2023
PRIMARY
CAS
51473-23-5
Created by admin on Fri Dec 15 15:14:29 UTC 2023 , Edited by admin on Fri Dec 15 15:14:29 UTC 2023
PRIMARY
NCI_THESAURUS
C81080
Created by admin on Fri Dec 15 15:14:29 UTC 2023 , Edited by admin on Fri Dec 15 15:14:29 UTC 2023
PRIMARY
PUBCHEM
20055399
Created by admin on Fri Dec 15 15:14:29 UTC 2023 , Edited by admin on Fri Dec 15 15:14:29 UTC 2023
PRIMARY
MESH
C084809
Created by admin on Fri Dec 15 15:14:29 UTC 2023 , Edited by admin on Fri Dec 15 15:14:29 UTC 2023
PRIMARY
FDA UNII
1945N48N9E
Created by admin on Fri Dec 15 15:14:29 UTC 2023 , Edited by admin on Fri Dec 15 15:14:29 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY