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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 treatment of hyperprolactinemia.
1989 Feb
CV 205-502, a new dopamine agonist, versus bromocriptine in the treatment of hyperprolactinaemia.
1991 Jul 1
Effects of tamoxifen and CV 205502 on the morphology and the evolution of the noncancerous mouse mammary gland.
1993 Oct
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 UTC 2023
Edited
by admin
on Fri Dec 15 16:15:49 UTC 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 UTC 2023 , Edited by admin on Fri Dec 15 16:15:49 UTC 2023
WHO-VATC QG02CB04
Created by admin on Fri Dec 15 16:15:49 UTC 2023 , Edited by admin on Fri Dec 15 16:15:49 UTC 2023
WHO-ATC G02CB04
Created by admin on Fri Dec 15 16:15:49 UTC 2023 , Edited by admin on Fri Dec 15 16:15:49 UTC 2023
Code System Code Type Description
ChEMBL
CHEMBL2218861
Created by admin on Fri Dec 15 16:15:49 UTC 2023 , Edited by admin on Fri Dec 15 16:15:49 UTC 2023
PRIMARY
RXCUI
76887
Created by admin on Fri Dec 15 16:15:49 UTC 2023 , Edited by admin on Fri Dec 15 16:15:49 UTC 2023
PRIMARY RxNorm
DRUG CENTRAL
2339
Created by admin on Fri Dec 15 16:15:49 UTC 2023 , Edited by admin on Fri Dec 15 16:15:49 UTC 2023
PRIMARY
EVMPD
SUB10199MIG
Created by admin on Fri Dec 15 16:15:49 UTC 2023 , Edited by admin on Fri Dec 15 16:15:49 UTC 2023
PRIMARY
DRUG BANK
DB09097
Created by admin on Fri Dec 15 16:15:49 UTC 2023 , Edited by admin on Fri Dec 15 16:15:49 UTC 2023
PRIMARY
MESH
C046650
Created by admin on Fri Dec 15 16:15:49 UTC 2023 , Edited by admin on Fri Dec 15 16:15:49 UTC 2023
PRIMARY
PUBCHEM
22942549
Created by admin on Fri Dec 15 16:15:49 UTC 2023 , Edited by admin on Fri Dec 15 16:15:49 UTC 2023
PRIMARY
FDA UNII
80Q9QWN15M
Created by admin on Fri Dec 15 16:15:49 UTC 2023 , Edited by admin on Fri Dec 15 16:15:49 UTC 2023
PRIMARY
INN
6545
Created by admin on Fri Dec 15 16:15:49 UTC 2023 , Edited by admin on Fri Dec 15 16:15:49 UTC 2023
PRIMARY
WIKIPEDIA
Quinagolide
Created by admin on Fri Dec 15 16:15:49 UTC 2023 , Edited by admin on Fri Dec 15 16:15:49 UTC 2023
PRIMARY
CAS
87056-78-8
Created by admin on Fri Dec 15 16:15:49 UTC 2023 , Edited by admin on Fri Dec 15 16:15:49 UTC 2023
PRIMARY
SMS_ID
100000081086
Created by admin on Fri Dec 15 16:15:49 UTC 2023 , Edited by admin on Fri Dec 15 16:15:49 UTC 2023
PRIMARY
NCI_THESAURUS
C73310
Created by admin on Fri Dec 15 16:15:49 UTC 2023 , Edited by admin on Fri Dec 15 16:15:49 UTC 2023
PRIMARY
MERCK INDEX
m9431
Created by admin on Fri Dec 15 16:15:49 UTC 2023 , Edited by admin on Fri Dec 15 16:15:49 UTC 2023
PRIMARY Merck Index
Related Record Type Details
ACTIVE MOIETY