quinagolide (CED0012878)

Record Information

Version

1.0

Creation Date

2016-06-03 10:20:51 UTC

Update Date

2026-05-14 19:02:31 UTC

SynCED ID

CED0012878

Secondary Accession Numbers

CHEM042863

Identification

Common Name

quinagolide

Class

Small Molecule

Description

Quinagolide is an organic compound with the formula C20H33N3O3S and an average molecular weight of 395.56 g/mol. It is recorded as being found in or released from healthcare, pharmaceuticals, and veterinary products, specifically gynecologicals, with oral exposure. Quinagolide belongs to the benzoquinolines, a subclass of quinolines and derivatives within the organic compounds. In terms of its biological activity, the compound acts as an agonist for three protein targets: the D(2) dopamine receptor (DRD2), the D(1A) dopamine receptor (DRD1), and the D(1B) dopamine receptor (DRD5).

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3-[(Diethylsulphamoyl)amino]-1-propyl-1H,2H,3H,4H,4ah,5H,10H,10ah-benzo[g]quinolin-6-ol	Generator
N,N-Diethyl-n'-(1,2,3,4,4a,5,10,10a-octahydro-6-hydroxy-1-propyl-3-benzo(g)quinolinyl)sulfamide hydrochloride, (3alpha,4aalpha,10abeta)-(+)-isomer	MeSH
Quinagolide hydrochloride	MeSH
N,N-Diethyl-n'-(1,2,3,4,4a,5,10,10a-octahydro-6-hydroxy-1-propyl-3-benzo(g)quinolinyl)sulfamide, (3alpha,4aalpha,10abeta)-(+-)-isomer	MeSH
Quinagolide hydrochloride, 3alpha,4aalpha,10abeta-(-)-isomer	MeSH
Quinagolide, (3alpha,4aalpha,10abeta)-(+-)-isomer	MeSH
Norprolac	MeSH
Quinagolide hydrochloride, (3alpha,4aalpha,10abeta)-(+)-isomer	MeSH

Chemical Formula

C₂₀H₃₃N₃O₃S

Average Molecular Mass

395.560 g/mol

Monoisotopic Mass

395.224 g/mol

CAS Registry Number

87056-78-8

IUPAC Name

3-[(diethylsulfamoyl)amino]-1-propyl-1H,2H,3H,4H,4aH,5H,10H,10aH-benzo[g]quinolin-6-ol

Traditional Name

quinagolide

SMILES

CCCN1CC(CC2CC3=C(CC12)C=CC=C3O)NS(=O)(=O)N(CC)CC

InChI Identifier

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

InChI Key

GDFGTRDCCWFXTG-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzoquinolines. These are organic compounds containing a benzene fused to a quinoline ring system.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Benzoquinolines

Direct Parent

Benzoquinolines

Alternative Parents

Substituents

Benzoquinoline
Tetralin
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Sulfuric acid diamide
Piperidine
Benzenoid
Organic sulfuric acid or derivatives
Tertiary amine
Tertiary aliphatic amine
Azacycle
Amine
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.15 g/L	ALOGPS
logP	2.56	ALOGPS
logP	2.5	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	10.2	ChemAxon
pKa (Strongest Basic)	8.22	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	72.88 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	109.66 m³·mol⁻¹	ChemAxon
Polarizability	44.98 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-05gr-7978000000-d63282e32cc0e5810c8a	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0005-2079000000-7fd94416ed44125b4ded	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-1190000000-60673d58d3436a38bea4	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-9620000000-c9dadf1aa5a87b63c6b7	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-0309000000-50f872a216f22905106f	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-2795000000-4bdfa79eb0b0faf12648	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03di-9220000000-38d2234d2f2e2a5d9f49	Not Available	View Spectrum

Toxicity Profile

Toxicity Values

Toxicity Value	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Toxicity Rating	Reference
1030.0 Log mg/kg [580:1800]	Rat	LD50	oral	predicted	Not Available	Not Available

Toxicity / Toxin Class

Not Available

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Health Effects

Health Effect	Relationship	Direction	Description	Reference

Exposure Sources

Source ID	Source	Sector	Reference
CEDs000316	Gynecologicals?Gynecologicals encompass a range of synthetic chemicals used in the treatment of various women's health issues, including hormonal therapies, contraceptives, and antifungal agents.	Healthcare, pharmaceuticals & veterinary products	Not Available

Pathways

2 pathwaysPathway Source: PathBank

Quinagolide Mechanism of Action Action Pathway

Quinagolide Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	D(2) dopamine receptor	P61169	Rat	Predicted (SEA)	Prediction Confidence Score 0.365 Applicability Domain 0.4 Statistical Significance 0.0207 Supporting Reference Compounds 528 E-value 161.304
Click to view 3D structure	5-hydroxytryptamine receptor 1A	P08908	Humans	Predicted (SEA)	Prediction Confidence Score 0.359 Applicability Domain 0.4 Statistical Significance 0.0275 Supporting Reference Compounds 953 E-value 214.085
Click to view 3D structure	D(3) dopamine receptor	P35462	Humans	Predicted (SEA)	Prediction Confidence Score 0.35 Applicability Domain 0.364 Statistical Significance 0.0297 Supporting Reference Compounds 861 E-value 231.134
Click to view 3D structure	D(2) dopamine receptor	P14416	Humans	Predicted (SEA)	Prediction Confidence Score 0.35 Applicability Domain 0.364 Statistical Significance 0.0393 Supporting Reference Compounds 1103 E-value 306.103
Click to view 3D structure	5-hydroxytryptamine receptor 1A	P19327	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.342 Applicability Domain 0.348 Statistical Significance 0.0255 Supporting Reference Compounds 541 E-value 198.282
Click to view 3D structure	D(3) dopamine receptor	P19020	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.34 Applicability Domain 0.359 Statistical Significance 0.0115 Supporting Reference Compounds 145 E-value 89.838
Click to view 3D structure	5-hydroxytryptamine receptor 7	P34969	Humans	Predicted (SEA)	Prediction Confidence Score 0.34 Applicability Domain 0.347 Statistical Significance 0.0244 Supporting Reference Compounds 565 E-value 189.952
Click to view 3D structure	D(1A) dopamine receptor	P18901	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.335 Applicability Domain 0.348 Statistical Significance 0.0127 Supporting Reference Compounds 206 E-value 99.2578
Click to view 3D structure	D(1A) dopamine receptor	P21728	Humans	Predicted (SEA)	Prediction Confidence Score 0.327 Applicability Domain 0.348 Statistical Significance 0.0211 Supporting Reference Compounds 425 E-value 164.028
Click to view 3D structure	D(4) dopamine receptor	P21917	Humans	Predicted (SEA)	Prediction Confidence Score 0.313 Applicability Domain 0.364 Statistical Significance 0.043 Supporting Reference Compounds 524 E-value 334.829
Click to view 3D structure	D(2) dopamine receptor	P20288	Bos taurus	Predicted (SEA)	Prediction Confidence Score 0.311 Applicability Domain 0.359 Statistical Significance 0.007 Supporting Reference Compounds 72 E-value 54.2609
Click to view 3D structure	5-hydroxytryptamine receptor 2A	P28223	Humans	Predicted (SEA)	Prediction Confidence Score 0.31 Applicability Domain 0.348 Statistical Significance 0.0661 Supporting Reference Compounds 955 E-value 514.583
Click to view 3D structure	5-hydroxytryptamine receptor 7	P32305	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.302 Applicability Domain 0.347 Statistical Significance 0.0158 Supporting Reference Compounds 115 E-value 122.924
Click to view 3D structure	5-hydroxytryptamine receptor 1D	P28221	Humans	Predicted (SEA)	Prediction Confidence Score 0.301 Applicability Domain 0.338 Statistical Significance 0.0285 Supporting Reference Compounds 365 E-value 222.026
Click to view 3D structure	5-hydroxytryptamine receptor 2C	P28335	Humans	Predicted (SEA)	Prediction Confidence Score 0.294 Applicability Domain 0.347 Statistical Significance 0.0789 Supporting Reference Compounds 823 E-value 614.23
Click to view 3D structure	Sigma non-opioid intracellular receptor 1	Q9R0C9	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.293 Applicability Domain 0.353 Statistical Significance 0.0267 Supporting Reference Compounds 207 E-value 207.624
Click to view 3D structure	5-hydroxytryptamine receptor 6	P50406	Humans	Predicted (SEA)	Prediction Confidence Score 0.292 Applicability Domain 0.347 Statistical Significance 0.0541 Supporting Reference Compounds 536 E-value 421.398
Click to view 3D structure	5-hydroxytryptamine receptor 2A	P35363	Mus musculus	Predicted (SEA)	Prediction Confidence Score 0.275 Applicability Domain 0.333 Statistical Significance 0.0073 Supporting Reference Compounds 47 E-value 56.9078
Click to view 3D structure	5-hydroxytryptamine receptor 2B	P41595	Humans	Predicted (SEA)	Prediction Confidence Score 0.273 Applicability Domain 0.347 Statistical Significance 0.1109 Supporting Reference Compounds 686 E-value 863.426
Click to view 3D structure	Sigma non-opioid intracellular receptor 1	Q99720	Humans	Predicted (SEA)	Prediction Confidence Score 0.273 Applicability Domain 0.338 Statistical Significance 0.1158 Supporting Reference Compounds 562 E-value 901.494
Click to view 3D structure	Alpha-1D adrenergic receptor	P25100	Humans	Predicted (SEA)	Prediction Confidence Score 0.269 Applicability Domain 0.338 Statistical Significance 0.0534 Supporting Reference Compounds 258 E-value 415.871
Click to view 3D structure	Alpha-1A adrenergic receptor	P43140	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.268 Applicability Domain 0.338 Statistical Significance 0.049 Supporting Reference Compounds 208 E-value 381.305
Click to view 3D structure	Alpha-2A adrenergic receptor	Q28838	Bos taurus	Predicted (SEA)	Prediction Confidence Score 0.267 Applicability Domain 0.338 Statistical Significance 0.0042 Supporting Reference Compounds 32 E-value 32.7745
Click to view 3D structure	Alpha-1A adrenergic receptor	P35348	Humans	Predicted (SEA)	Prediction Confidence Score 0.265 Applicability Domain 0.338 Statistical Significance 0.09 Supporting Reference Compounds 376 E-value 701.032
Click to view 3D structure	5-hydroxytryptamine receptor 1B	P28564	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.264 Applicability Domain 0.338 Statistical Significance 0.0428 Supporting Reference Compounds 154 E-value 333.117