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Details

Stereochemistry RACEMIC
Molecular Formula C20H33N3O3S
Molecular Weight 395.559
Optical Activity ( + / - )
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of QUINAGOLIDE

SMILES

[H][C@@]12C[C@H](CN(CCC)[C@@]1([H])CC3=C(C2)C(O)=CC=C3)NS(=O)(=O)N(CC)CC

InChI

InChIKey=GDFGTRDCCWFXTG-SCTDSRPQSA-N
InChI=1S/C20H33N3O3S/c1-4-10-22-14-17(21-27(25,26)23(5-2)6-3)11-16-12-18-15(13-19(16)22)8-7-9-20(18)24/h7-9,16-17,19,21,24H,4-6,10-14H2,1-3H3/t16-,17+,19-/m0/s1

HIDE SMILES / InChI

Molecular Formula C20H33N3O3S
Molecular Weight 395.559
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

CV-205502 (Quinagolide, Norprolac), a small molecule, dopamine 2-receptor agonist was developed by Novartis for the treatment of prolactinoma and hyperprolactinaemia. It is is a long-acting dopamine agonist with potent D2 and weak D1 activity. Quinagolide exists as a racemate and its relevant clinical activity is mediated predominantly by the (-) enantiomer. It is typically present in the hydrochloride salt form and is marketed as oral tablets under the brand name Norprolac contained as a racemate. Quinagolide is currently available in several countries including Canada, but not approved for treatment in the United States. Owing to its dopaminergic action, the drug exerts a strong inhibitory effect on the secretion of the anterior pituitary hormone prolactin, but does not reduce normal levels of other pituitary hormones. Long-term treatment with Norprolac was found to reduce the size or limit the growth of prolactin-secreting pituitary macroadenomas. In some patients the reduction of prolactin secretion may be accompanied by short- lasting, small increases in plasma growth hormone levels, the clinical significance of which is unknown. As a specific inhibitor of prolactin secretion with a prolonged duration of action, Norprolac has been shown to be effective and suitable for once-a- day oral treatment of patients presenting with hyperprolactinaemia and its clinical manifestations such as galactorrhoea, oligomenorrhoea, amenorrhoea, infertility and reduced libido.

Approval Year

PubMed

PubMed

TitleDatePubMed
CV 205-502: safety, tolerance to, and efficacy of increasing doses in patients with Parkinson's disease in a double-blind, placebo crossover study.
1989 Dec
CV 205-502, a new dopamine agonist, versus bromocriptine in the treatment of hyperprolactinaemia.
1991 Jul 1
Patents

Sample Use Guides

Adults The optimal dose must be titrated individually on the basis of the prolactin- lowering effect and tolerability. With the 'starter pack' treatment begins with 25 micrograms/day for the first 3 days, followed by 50 micrograms/day for a further 3 days. From day 7 onwards, the recommended dose is 75 micrograms/day. If necessary, the daily dose may then be increased stepwise until the optimal individual response is attained. The usual maintenance dosage is 75 to 150 micrograms/day. Daily doses of 300 micrograms or higher doses are required in less than one- third of the patients. In such cases, the daily dosage may be increased in steps of 75 to 150 micrograms at intervals not shorter than 4 weeks until satisfactory therapeutic effectiveness is achieved or reduced tolerability, requiring the discontinuation of treatment, occurs.
Route of Administration: Oral
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:15:49 GMT 2023
Edited
by admin
on Fri Dec 15 16:15:49 GMT 2023
Record UNII
80Q9QWN15M
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
QUINAGOLIDE
INN   MI   WHO-DD  
INN  
Official Name English
QUINAGOLIDE [MI]
Common Name English
quinagolide [INN]
Common Name English
Quinagolide [WHO-DD]
Common Name English
(±)-N,N-DIETHYL-N'-((3R*,4AR*,10AS*)-1,2,3,4,4A,5,10,10A-OCTAHYDRO-6-HYDROXY-1-PROPYLBENZO(G)QUINOLIN-3-YL)SULFAMIDE
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29710
Created by admin on Fri Dec 15 16:15:49 GMT 2023 , Edited by admin on Fri Dec 15 16:15:49 GMT 2023
WHO-VATC QG02CB04
Created by admin on Fri Dec 15 16:15:49 GMT 2023 , Edited by admin on Fri Dec 15 16:15:49 GMT 2023
WHO-ATC G02CB04
Created by admin on Fri Dec 15 16:15:49 GMT 2023 , Edited by admin on Fri Dec 15 16:15:49 GMT 2023
Code System Code Type Description
ChEMBL
CHEMBL2218861
Created by admin on Fri Dec 15 16:15:49 GMT 2023 , Edited by admin on Fri Dec 15 16:15:49 GMT 2023
PRIMARY
RXCUI
76887
Created by admin on Fri Dec 15 16:15:49 GMT 2023 , Edited by admin on Fri Dec 15 16:15:49 GMT 2023
PRIMARY RxNorm
DRUG CENTRAL
2339
Created by admin on Fri Dec 15 16:15:49 GMT 2023 , Edited by admin on Fri Dec 15 16:15:49 GMT 2023
PRIMARY
EVMPD
SUB10199MIG
Created by admin on Fri Dec 15 16:15:49 GMT 2023 , Edited by admin on Fri Dec 15 16:15:49 GMT 2023
PRIMARY
DRUG BANK
DB09097
Created by admin on Fri Dec 15 16:15:49 GMT 2023 , Edited by admin on Fri Dec 15 16:15:49 GMT 2023
PRIMARY
MESH
C046650
Created by admin on Fri Dec 15 16:15:49 GMT 2023 , Edited by admin on Fri Dec 15 16:15:49 GMT 2023
PRIMARY
PUBCHEM
22942549
Created by admin on Fri Dec 15 16:15:49 GMT 2023 , Edited by admin on Fri Dec 15 16:15:49 GMT 2023
PRIMARY
FDA UNII
80Q9QWN15M
Created by admin on Fri Dec 15 16:15:49 GMT 2023 , Edited by admin on Fri Dec 15 16:15:49 GMT 2023
PRIMARY
INN
6545
Created by admin on Fri Dec 15 16:15:49 GMT 2023 , Edited by admin on Fri Dec 15 16:15:49 GMT 2023
PRIMARY
WIKIPEDIA
Quinagolide
Created by admin on Fri Dec 15 16:15:49 GMT 2023 , Edited by admin on Fri Dec 15 16:15:49 GMT 2023
PRIMARY
CAS
87056-78-8
Created by admin on Fri Dec 15 16:15:49 GMT 2023 , Edited by admin on Fri Dec 15 16:15:49 GMT 2023
PRIMARY
SMS_ID
100000081086
Created by admin on Fri Dec 15 16:15:49 GMT 2023 , Edited by admin on Fri Dec 15 16:15:49 GMT 2023
PRIMARY
NCI_THESAURUS
C73310
Created by admin on Fri Dec 15 16:15:49 GMT 2023 , Edited by admin on Fri Dec 15 16:15:49 GMT 2023
PRIMARY
MERCK INDEX
m9431
Created by admin on Fri Dec 15 16:15:49 GMT 2023 , Edited by admin on Fri Dec 15 16:15:49 GMT 2023
PRIMARY Merck Index
Related Record Type Details
ACTIVE MOIETY