Quinagolide hydrochlorideProduct ingredient for Quinagolide

Name
Quinagolide hydrochloride
Drug Entry
Quinagolide

Quinagolide is a non-ergot-derived selective dopamine D2 receptor agonist used for the treatment of elevated levels of prolactin or hyperprolactinaemia. Hyperprolalctinaemia is associated with gonadal dysfunction, including infertility and reduced libido, as well as long-term complications such as osteoporosis 1. Newer dopamine receptor agonists such as quinagolide and Cabergoline are shown to effectively inhibit prolactin secretion with improved efficacy over Bromocriptine. These drugs are effective in patients who are intolerant or resistant to Bromocriptine. 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.

Accession Number
DBSALT001152
Structure
Synonyms
Quinagolide HCl
External IDs
SDZ 205-502 / SDZ-205-502
UNII
33474X943Y
CAS Number
94424-50-7
Weight
Average: 432.02
Monoisotopic: 431.2009408
Chemical Formula
C20H34ClN3O3S
InChI Key
DVLKVIJLALMCBQ-VENMBWNLSA-N
InChI
InChI=1S/C20H33N3O3S.ClH/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;1H/t16-,17+,19-;/m0./s1
IUPAC Name
(3R,4aR,10aS)-3-[(diethylsulfamoyl)amino]-1-propyl-1H,2H,3H,4H,4aH,5H,10H,10aH-benzo[g]quinolin-6-ol hydrochloride
SMILES
Cl.CCCN1C[C@@H](C[C@H]2CC3=C(O)C=CC=C3C[C@H]12)NS(=O)(=O)N(CC)CC
ChemSpider
32702007
Predicted Properties
PropertyValueSource
Water Solubility0.154 mg/mLALOGPS
logP2.56ALOGPS
logP2.5Chemaxon
logS-3.4ALOGPS
pKa (Strongest Acidic)10.2Chemaxon
pKa (Strongest Basic)8.22Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area72.88 Å2Chemaxon
Rotatable Bond Count5Chemaxon
Refractivity109.66 m3·mol-1Chemaxon
Polarizability44.61 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon