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

Details

Stereochemistry ABSOLUTE
Molecular Formula C26H37N5O2
Molecular Weight 451.6043
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CABERGOLINE

SMILES

[H][C@@]12CC3=CNC4=C3C(=CC=C4)[C@@]1([H])C[C@H](CN2CC=C)C(=O)N(CCCN(C)C)C(=O)NCC

InChI

InChIKey=KORNTPPJEAJQIU-KJXAQDMKSA-N
InChI=1S/C26H37N5O2/c1-5-11-30-17-19(25(32)31(26(33)27-6-2)13-8-12-29(3)4)14-21-20-9-7-10-22-24(20)18(16-28-22)15-23(21)30/h5,7,9-10,16,19,21,23,28H,1,6,8,11-15,17H2,2-4H3,(H,27,33)/t19-,21-,23-/m1/s1

HIDE SMILES / InChI

Molecular Formula C26H37N5O2
Molecular Weight 451.6043
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: description was created based on several sources, including: https://www.drugs.com/dosage/cabergoline.html http://www.wikidoc.org/index.php/Cabergoline http://www.rxlist.com/dostinex-drug.htm

Cabergoline is a long-acting dopamine receptor agonist with a high affinity for D2 receptors. Results of in vitro studies demonstrate that cabergoline exerts a direct inhibitory effect on the secretion of prolactin by rat pituitary lactotrophs. It is FDA approved for the treatment of hyperprolactinemic disorders, either idiopathic or due to pituitary adenomas. Common adverse reactions include constipation, nausea, dizziness, headache and fatigue. Cabergoline should not be administered concurrently with D-antagonists, such as phenothiazines, butyrophenones, thioxanthenes, or metoclopramide.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
CABERGOLINE

Approved Use

Cabergoline tablets are indicated for the treatment of hyperprolactinemic disorders, either idiopathic or due to pituitary adenomas.

Launch Date

2005
Primary
CABERGOLINE

Approved Use

Cabergoline tablets are indicated for the treatment of hyperprolactinemic disorders, either idiopathic or due to pituitary adenomas.

Launch Date

2005
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
33.3 ng/L
0.5 mg single, oral
dose: 0.5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CABERGOLINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
40.3 ng/L
1 mg single, oral
dose: 1 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CABERGOLINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
67 ng/L
1.5 mg single, oral
dose: 1.5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CABERGOLINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
12952 ng × h/L
0.5 mg single, oral
dose: 0.5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CABERGOLINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
1884 ng × h/L
1 mg single, oral
dose: 1 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CABERGOLINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
2546 ng × h/L
1.5 mg single, oral
dose: 1.5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CABERGOLINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
68.54 h
1 mg single, oral
dose: 1 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CABERGOLINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: FASTED
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
60%
unknown, unknown
CABERGOLINE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
20 mg 1 times / day multiple, oral
Highest studied dose
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Co-administed with::
L-dopa, po(370.6 mg)
Sources: Page: p.18, p.19, p.22
unhealthy, 41.0–73.5
n = 34
Health Status: unhealthy
Condition: Parkinson’s disease
Age Group: 41.0–73.5
Sex: M+F
Population Size: 34
Sources: Page: p.18, p.19, p.22
Sources: Page: p.18, p.19, p.22
2 mg 1 times / day multiple, oral (min)
Overdose
Dose: 2 mg, 1 times / day
Route: oral
Route: multiple
Dose: 2 mg, 1 times / day
Sources: Page: p.4
unhealthy
Health Status: unhealthy
Condition: Parkinson’s disease
Sources: Page: p.4
Other AEs: Cardiac valvulopathy...
0.5 mg 2 times / week multiple, oral
Recommended
Dose: 0.5 mg, 2 times / week
Route: oral
Route: multiple
Dose: 0.5 mg, 2 times / week
Sources: Page: p.9
unhealthy
n = 221
Health Status: unhealthy
Condition: Hyperprolactinemic disorders
Population Size: 221
Sources: Page: p.9
Disc. AE: Headache, Nausea...
AEs leading to
discontinuation/dose reduction:
Headache (1.4%)
Nausea (0.9%)
Vomiting (0.9%)
Sources: Page: p.9
1 mg 2 times / week multiple, oral (max)
Recommended
Dose: 1 mg, 2 times / week
Route: oral
Route: multiple
Dose: 1 mg, 2 times / week
Sources: Page: p.4
unhealthy
Health Status: unhealthy
Condition: Hyperprolactinemic disorders
Sources: Page: p.4
Disc. AE: Pleural effusion, Pulmonary fibrosis...
Other AEs: Cardiac valvulopathy, Pericardial fibrosis...
AEs leading to
discontinuation/dose reduction:
Pleural effusion
Pulmonary fibrosis
Other AEs:
Cardiac valvulopathy
Pericardial fibrosis
Retroperitoneal fibrosis
Sources: Page: p.4
AEs

AEs

AESignificanceDosePopulation
Cardiac valvulopathy
2 mg 1 times / day multiple, oral (min)
Overdose
Dose: 2 mg, 1 times / day
Route: oral
Route: multiple
Dose: 2 mg, 1 times / day
Sources: Page: p.4
unhealthy
Health Status: unhealthy
Condition: Parkinson’s disease
Sources: Page: p.4
Nausea 0.9%
Disc. AE
0.5 mg 2 times / week multiple, oral
Recommended
Dose: 0.5 mg, 2 times / week
Route: oral
Route: multiple
Dose: 0.5 mg, 2 times / week
Sources: Page: p.9
unhealthy
n = 221
Health Status: unhealthy
Condition: Hyperprolactinemic disorders
Population Size: 221
Sources: Page: p.9
Vomiting 0.9%
Disc. AE
0.5 mg 2 times / week multiple, oral
Recommended
Dose: 0.5 mg, 2 times / week
Route: oral
Route: multiple
Dose: 0.5 mg, 2 times / week
Sources: Page: p.9
unhealthy
n = 221
Health Status: unhealthy
Condition: Hyperprolactinemic disorders
Population Size: 221
Sources: Page: p.9
Headache 1.4%
Disc. AE
0.5 mg 2 times / week multiple, oral
Recommended
Dose: 0.5 mg, 2 times / week
Route: oral
Route: multiple
Dose: 0.5 mg, 2 times / week
Sources: Page: p.9
unhealthy
n = 221
Health Status: unhealthy
Condition: Hyperprolactinemic disorders
Population Size: 221
Sources: Page: p.9
Cardiac valvulopathy
1 mg 2 times / week multiple, oral (max)
Recommended
Dose: 1 mg, 2 times / week
Route: oral
Route: multiple
Dose: 1 mg, 2 times / week
Sources: Page: p.4
unhealthy
Health Status: unhealthy
Condition: Hyperprolactinemic disorders
Sources: Page: p.4
Pericardial fibrosis
1 mg 2 times / week multiple, oral (max)
Recommended
Dose: 1 mg, 2 times / week
Route: oral
Route: multiple
Dose: 1 mg, 2 times / week
Sources: Page: p.4
unhealthy
Health Status: unhealthy
Condition: Hyperprolactinemic disorders
Sources: Page: p.4
Retroperitoneal fibrosis
1 mg 2 times / week multiple, oral (max)
Recommended
Dose: 1 mg, 2 times / week
Route: oral
Route: multiple
Dose: 1 mg, 2 times / week
Sources: Page: p.4
unhealthy
Health Status: unhealthy
Condition: Hyperprolactinemic disorders
Sources: Page: p.4
Pleural effusion Disc. AE
1 mg 2 times / week multiple, oral (max)
Recommended
Dose: 1 mg, 2 times / week
Route: oral
Route: multiple
Dose: 1 mg, 2 times / week
Sources: Page: p.4
unhealthy
Health Status: unhealthy
Condition: Hyperprolactinemic disorders
Sources: Page: p.4
Pulmonary fibrosis Disc. AE
1 mg 2 times / week multiple, oral (max)
Recommended
Dose: 1 mg, 2 times / week
Route: oral
Route: multiple
Dose: 1 mg, 2 times / week
Sources: Page: p.4
unhealthy
Health Status: unhealthy
Condition: Hyperprolactinemic disorders
Sources: Page: p.4
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
likely
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
yes
yes (co-administration study)
Comment: n healthy male volunteers, the mean of Cmax and AUC of cabergoline increased around 2.7 times by coadministration of clarithromycin.
Page: -
PubMed

PubMed

TitleDatePubMed
Clinical data on restless legs syndrome: a dose-finding study with cabergoline.
2001
Actigraph analysis of diurnal motor fluctuations during dopamine agonist therapy.
2001
Cabergoline for levodopa-induced complications in Parkinson's disease.
2001
Successful treatment of a large macroprolactinoma with cabergoline during pregnancy.
2001 Aug
Upregulation of lymphocyte apoptosis as a strategy for preventing and treating autoimmune disorders: a role for whole-food vegan diets, fish oil and dopamine agonists.
2001 Aug
Control of unremitting rheumatoid arthritis by the prolactin antagonist cabergoline.
2001 Feb
ACTH silent adenoma shrinking under cabergoline.
2001 Jan
Tumour shrinkage and chiasmal herniation after successful cabergoline treatment for a macroprolactinoma.
2001 Jan
Control of red fox (Vulpes vulpes) fertility with cabergoline: dose response and timing of intervention.
2001 Jul
Clusterlike headache as first manifestation of a prolactinoma.
2001 Jul-Aug
[Pharmacological effects of cabergoline against parkinsonism].
2001 Jun
Study of the change of prolactin and progesterone during dopaminergic agonist treatments in pseudopregnant bitches.
2001 May 31
Resistance to cabergoline as compared with bromocriptine in hyperprolactinemia: prevalence, clinical definition, and therapeutic strategy.
2001 Nov
Cabergoline influences ovarian stimulation in hyperprolactinaemic patients with polycystic ovary syndrome.
2001 Nov
Effectiveness of cabergoline for termination of pregnancy in silver fox (Vulpes vulpes fulva).
2001 Oct
Determination of cabergoline by electrospray ionization tandem mass spectrometry: picogram detection via column focusing sample introduction.
2001 Oct 15
[A case of elderly onset Parkinson's disease complicated by dropped head syndrome].
2001 Sep
Comparison of the effects of cabergoline and bromocriptine on prolactin levels in hyperprolactinemic patients.
2001 Sep
Cabergoline, a hopeful medicine for prolactinomas and non-tumoral hyperprolactinemia.
2001 Sep
Disorders of prolactin secretion.
2001 Sep
Treatment of risperidone-induced hyperprolactinemia with a dopamine agonist in children.
2001 Winter
DA agonists -- ergot derivatives: bromocriptine: management of Parkinson's disease.
2002
Macroprolactinoma associated with Cushing's disease, successfully treated with cabergoline.
2002 Feb
Giant prolactinomas presenting as skull base tumors.
2002 Feb
Restless legs syndrome: treatment with dopaminergic agents.
2002 Feb 26
Long-term studies of dopamine agonists.
2002 Feb 26
Effects of short- and long-acting dopamine agonists on sensitized dopaminergic neurotransmission in rats with unilateral 6-OHDA lesions.
2002 Jan 18
The dopamine agonist cabergoline provides neuroprotection by activation of the glutathione system and scavenging free radicals.
2002 Jul
Gateways to clinical trials.
2002 Jul-Aug
Dopamine receptor agonists for treating prolactinomas.
2002 Jun
Cabergoline can increase penile erections and libido.
2002 Mar 12
Differential actions of antiparkinson agents at multiple classes of monoaminergic receptor. II. Agonist and antagonist properties at subtypes of dopamine D(2)-like receptor and alpha(1)/alpha(2)-adrenoceptor.
2002 Nov
Circulating nitric oxide changes throughout the menstrual cycle in healthy women and women affected by pathological hyperprolactinemia on dopamine agonist therapy.
2002 Oct
An evidence-based review of dopamine receptor agonists in the treatment of Parkinson's disease.
2002 Oct
A practical synthesis of cabergoline.
2002 Oct 4
Gateways to Clinical Trials.
2002 Sep
Microstructure of the non-rapid eye movement sleep electroencephalogram in patients with newly diagnosed Parkinson's disease: effects of dopaminergic treatment.
2002 Sep
Gender differences in the prevalence, clinical features and response to cabergoline in hyperprolactinemia.
2003 Mar
Patents

Sample Use Guides

The recommended dosage for initiation of therapy is 0.25 mg twice a week. Dosage may be increased by 0.25 mg twice weekly up to a dosage of 1 mg twice a week according to the patient’s serum prolactin level. Dosage increases should not occur more rapidly than every 4 weeks.
Route of Administration: Oral
Tert-butylhydroperoxide caused a 42+/-4% neuronal death, which was prevented by cabergoline (2 h before) in a concentration-dependent manner (EC(50): 1.24 microM).
Substance Class Chemical
Created
by admin
on Sat Dec 16 16:22:08 GMT 2023
Edited
by admin
on Sat Dec 16 16:22:08 GMT 2023
Record UNII
LL60K9J05T
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CABERGOLINE
EP   INN   JAN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
USAN   INN  
Official Name English
FCE-21336
Code English
DOSTINEX
Brand Name English
CABERGOLINE [JAN]
Common Name English
CABERGOLINE [VANDF]
Common Name English
VELACTIS
Brand Name English
CABASER
Brand Name English
Cabergoline [WHO-DD]
Common Name English
CABERGOLINE [USP-RS]
Common Name English
ERGOLINE-8.BETA.-CARBOXAMIDE, N-(3-(DIMETHYLAMINO)PROPYL)-N-((ETHYLAMINO)CARBONYL)-6-(2-PROPENYL)-
Systematic Name English
CABERGOLINE [ORANGE BOOK]
Common Name English
FCE 21336
Code English
CABERGOLINE [USAN]
Common Name English
1-[(6-Allylergolin-8β-yl)carbonyl]-1-[3-(dimethylamino)propyl]-3-ethylurea
Systematic Name English
CABERGOLINE [EP MONOGRAPH]
Common Name English
cabergoline [INN]
Common Name English
CABERGOLINE [MI]
Common Name English
CABERGOLINE [MART.]
Common Name English
CABERGOLINE [USP MONOGRAPH]
Common Name English
CABERGOLINE [EMA EPAR VETERINARY]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C66884
Created by admin on Sat Dec 16 16:22:10 GMT 2023 , Edited by admin on Sat Dec 16 16:22:10 GMT 2023
NCI_THESAURUS C38149
Created by admin on Sat Dec 16 16:22:10 GMT 2023 , Edited by admin on Sat Dec 16 16:22:10 GMT 2023
WHO-VATC QG02CB03
Created by admin on Sat Dec 16 16:22:10 GMT 2023 , Edited by admin on Sat Dec 16 16:22:10 GMT 2023
WHO-ATC N04BC06
Created by admin on Sat Dec 16 16:22:10 GMT 2023 , Edited by admin on Sat Dec 16 16:22:10 GMT 2023
NDF-RT N0000007618
Created by admin on Sat Dec 16 16:22:10 GMT 2023 , Edited by admin on Sat Dec 16 16:22:10 GMT 2023
LIVERTOX 135
Created by admin on Sat Dec 16 16:22:10 GMT 2023 , Edited by admin on Sat Dec 16 16:22:10 GMT 2023
WHO-VATC QN04BC06
Created by admin on Sat Dec 16 16:22:10 GMT 2023 , Edited by admin on Sat Dec 16 16:22:10 GMT 2023
NDF-RT N0000175827
Created by admin on Sat Dec 16 16:22:10 GMT 2023 , Edited by admin on Sat Dec 16 16:22:10 GMT 2023
WHO-ATC G02CB03
Created by admin on Sat Dec 16 16:22:10 GMT 2023 , Edited by admin on Sat Dec 16 16:22:10 GMT 2023
NDF-RT N0000007618
Created by admin on Sat Dec 16 16:22:10 GMT 2023 , Edited by admin on Sat Dec 16 16:22:10 GMT 2023
EMA VETERINARY ASSESSMENT REPORTS VELACTIS [SUSPENDED]
Created by admin on Sat Dec 16 16:22:10 GMT 2023 , Edited by admin on Sat Dec 16 16:22:10 GMT 2023
Code System Code Type Description
ChEMBL
CHEMBL1201087
Created by admin on Sat Dec 16 16:22:10 GMT 2023 , Edited by admin on Sat Dec 16 16:22:10 GMT 2023
PRIMARY
DRUG CENTRAL
460
Created by admin on Sat Dec 16 16:22:10 GMT 2023 , Edited by admin on Sat Dec 16 16:22:10 GMT 2023
PRIMARY
MESH
C047047
Created by admin on Sat Dec 16 16:22:10 GMT 2023 , Edited by admin on Sat Dec 16 16:22:10 GMT 2023
PRIMARY
WIKIPEDIA
CABERGOLINE
Created by admin on Sat Dec 16 16:22:10 GMT 2023 , Edited by admin on Sat Dec 16 16:22:10 GMT 2023
PRIMARY
CAS
81409-90-7
Created by admin on Sat Dec 16 16:22:10 GMT 2023 , Edited by admin on Sat Dec 16 16:22:10 GMT 2023
PRIMARY
IUPHAR
37
Created by admin on Sat Dec 16 16:22:10 GMT 2023 , Edited by admin on Sat Dec 16 16:22:10 GMT 2023
PRIMARY
NCI_THESAURUS
C47428
Created by admin on Sat Dec 16 16:22:10 GMT 2023 , Edited by admin on Sat Dec 16 16:22:10 GMT 2023
PRIMARY
INN
5860
Created by admin on Sat Dec 16 16:22:10 GMT 2023 , Edited by admin on Sat Dec 16 16:22:10 GMT 2023
PRIMARY
SMS_ID
100000092143
Created by admin on Sat Dec 16 16:22:10 GMT 2023 , Edited by admin on Sat Dec 16 16:22:10 GMT 2023
PRIMARY
USAN
II-10
Created by admin on Sat Dec 16 16:22:10 GMT 2023 , Edited by admin on Sat Dec 16 16:22:10 GMT 2023
PRIMARY
EPA CompTox
DTXSID6022719
Created by admin on Sat Dec 16 16:22:10 GMT 2023 , Edited by admin on Sat Dec 16 16:22:10 GMT 2023
PRIMARY
RXCUI
47579
Created by admin on Sat Dec 16 16:22:10 GMT 2023 , Edited by admin on Sat Dec 16 16:22:10 GMT 2023
PRIMARY RxNorm
CHEBI
3286
Created by admin on Sat Dec 16 16:22:10 GMT 2023 , Edited by admin on Sat Dec 16 16:22:10 GMT 2023
PRIMARY
RS_ITEM_NUM
1084306
Created by admin on Sat Dec 16 16:22:10 GMT 2023 , Edited by admin on Sat Dec 16 16:22:10 GMT 2023
PRIMARY
PUBCHEM
54746
Created by admin on Sat Dec 16 16:22:10 GMT 2023 , Edited by admin on Sat Dec 16 16:22:10 GMT 2023
PRIMARY
LACTMED
Cabergoline
Created by admin on Sat Dec 16 16:22:10 GMT 2023 , Edited by admin on Sat Dec 16 16:22:10 GMT 2023
PRIMARY
EVMPD
SUB06041MIG
Created by admin on Sat Dec 16 16:22:10 GMT 2023 , Edited by admin on Sat Dec 16 16:22:10 GMT 2023
PRIMARY
DRUG BANK
DB00248
Created by admin on Sat Dec 16 16:22:10 GMT 2023 , Edited by admin on Sat Dec 16 16:22:10 GMT 2023
PRIMARY
DAILYMED
LL60K9J05T
Created by admin on Sat Dec 16 16:22:10 GMT 2023 , Edited by admin on Sat Dec 16 16:22:10 GMT 2023
PRIMARY
FDA UNII
LL60K9J05T
Created by admin on Sat Dec 16 16:22:10 GMT 2023 , Edited by admin on Sat Dec 16 16:22:10 GMT 2023
PRIMARY
MERCK INDEX
m2876
Created by admin on Sat Dec 16 16:22:10 GMT 2023 , Edited by admin on Sat Dec 16 16:22:10 GMT 2023
PRIMARY Merck Index
Related Record Type Details
SALT/SOLVATE -> PARENT
BINDER->LIGAND
BINDING
TARGET -> AGONIST
BASIS OF STRENGTH->SUBSTANCE
ASSAY (HPLC)
EP
BASIS OF STRENGTH->SUBSTANCE
ASSAY (HPLC)
USP
Related Record Type Details
METABOLITE -> PARENT
7% in urine
MINOR
URINE
METABOLITE -> PARENT
41% in urine
MAJOR
URINE
Related Record Type Details
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
IMPURITY -> PARENT
IMPURITY -> PARENT
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC