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
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
DescriptionCurator'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
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.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL234 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18691132 |
1.5 nM [Ki] | ||
Target ID: CHEMBL2095169 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18691132 |
0.5 nM [Ki] | ||
Target ID: CHEMBL1833 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18691132 |
1.2 nM [Ki] | ||
Target ID: CHEMBL217 |
0.69 nM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | CABERGOLINE Approved UseCabergoline tablets are indicated for the treatment of hyperprolactinemic disorders, either idiopathic or due to pituitary adenomas. Launch Date1.13581438E12 |
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Primary | CABERGOLINE Approved UseCabergoline tablets are indicated for the treatment of hyperprolactinemic disorders, either idiopathic or due to pituitary adenomas. Launch Date1.13581438E12 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
33.3 ng/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7883840 |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7883840 |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7883840 |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
12952 ng × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7883840 |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7883840 |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7883840 |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
68.54 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7884663 |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
60% |
unknown, unknown |
CABERGOLINE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse 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 |
|
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... Other AEs: Cardiac valvulopathy Sources: Page: p.4 |
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%) Sources: Page: p.9Nausea (0.9%) Vomiting (0.9%) |
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 Other AEs:Pulmonary fibrosis Cardiac valvulopathy Sources: Page: p.4Pericardial fibrosis Retroperitoneal fibrosis |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
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
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/31183987/ Page: - |
likely |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: - |
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
Title | Date | PubMed |
---|---|---|
Use of the dopamine agonists bromocriptine and cabergoline in the management of risperidone-induced hyperprolactinemia in patients with psychotic disorders. | 2000 Dec |
|
Bait-delivered cabergoline for the reproductive control of the red fox (Vulpes vulpes): estimating mammalian non-target risk in south-eastern Australia. | 2001 |
|
Actigraph analysis of diurnal motor fluctuations during dopamine agonist therapy. | 2001 |
|
Regulation of dopamine receptors and motor behavior following pulsatile and continuous dopaminergic replacement strategies in the MPTP primate model. | 2001 |
|
Cabergoline versus bromocriptine for levodopa-induced complications in Parkinson's disease. | 2001 |
|
A study of excessive daytime sleepiness and its clinical significance in three groups of Parkinson's disease patients taking pramipexole, cabergoline and levodopa mono and combination therapy. | 2001 |
|
Minor tumour shrinkage in nonfunctioning pituitary adenomas by long-term treatment with the dopamine agonist cabergoline. | 2001 Aug |
|
Effects of dopamine d2 receptor agonists in a pituitary transplantation-induced hyperprolactinaemia/anovulation model in rats. | 2001 Aug |
|
Control of red fox (Vulpes vulpes) fertility with cabergoline: dose response and timing of intervention. | 2001 Jul |
|
Laboratory and clinical experience in 55 patients with macroprolactinemia identified by a simple polyethylene glycol precipitation method. | 2001 Jun |
|
Cabergoline-induced CSF rhinorrhea in patients with macroprolactinoma. Report of three cases. | 2001 Mar |
|
Sudden daytime sleep onset in Parkinson's disease: polysomnographic recordings. | 2001 May |
|
Study of the change of prolactin and progesterone during dopaminergic agonist treatments in pseudopregnant bitches. | 2001 May 31 |
|
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 |
|
Comparison of the effects of cabergoline and bromocriptine on prolactin levels in hyperprolactinemic patients. | 2001 Sep |
|
Disorders of prolactin secretion. | 2001 Sep |
|
Medical management of prolactin-secreting pituitary adenomas. | 2002 |
|
Assessment of cabergoline as a reproductive inhibitor in coyotes (Canis latrans). | 2002 |
|
DA agonists -- ergot derivatives: bromocriptine: management of Parkinson's disease. | 2002 |
|
Control of fertility in the red fox (Vulpes vulpes): effect of a single oral dose of cabergoline in early pregnancy. | 2002 |
|
Clinical pharmacokinetic and pharmacodynamic properties of drugs used in the treatment of Parkinson's disease. | 2002 |
|
Pregnancy termination in the bitch and queen. | 2002 Aug |
|
Switch to quetiapine in antipsychotic agent-related hyperprolactinemia. | 2002 Dec |
|
Alopecia induced by dopamine agonists. | 2002 Dec 24 |
|
Macroprolactinoma associated with Cushing's disease, successfully treated with cabergoline. | 2002 Feb |
|
Treatment of Parkinson's disease and restless legs syndrome with cabergoline, a long-acting dopamine agonist. | 2002 Jul-Aug |
|
Use of cabergoline to treat primary and secondary anestrus in dogs. | 2002 Jun 1 |
|
Cabergoline can increase penile erections and libido. | 2002 Mar 12 |
|
Hyperprolactinemia: etiology, diagnosis, and management. | 2002 Nov |
|
Cabergoline plasma concentration is increased during concomitant treatment with itraconazole. | 2002 Nov |
|
Long term tolerability of high dose ergoline derived dopamine agonist therapy for the treatment of Parkinson's disease. | 2002 Nov |
|
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 |
|
Detecting dose-response using contrasts: asymptotic power and sample size determination for binomial data. | 2002 Nov 30 |
|
Autonomic failure mimicing dopamine agonist induced vertigo in a patient with macroprolactinoma. | 2002 Oct |
|
A practical synthesis of cabergoline. | 2002 Oct 4 |
|
Combination of two different dopamine agonists in the management of Parkinson's disease. | 2002 Sep |
|
Gateways to Clinical Trials. | 2002 Sep |
|
Accurate mass measurement at enhanced mass-resolution on a triple quadrupole mass-spectrometer for the identification of a reaction impurity and collisionally-induced fragment ions of cabergoline. | 2003 |
|
Treatment with cabergoline is associated with weight loss in patients with hyperprolactinemia. | 2003 Feb |
|
Radioimmunoassay of prolactin for the meerkat (Suricata suricatta), a cooperatively breeding carnivore. | 2003 Feb 1 |
|
Hyperprolactinemia in men: clinical and biochemical features and response to treatment. | 2003 Feb-Mar |
|
Involvement of PI3'-K, mitogen-activated protein kinase and protein kinase B in the up-regulation of the expression of nNOSalpha and nNOSbeta splicing variants induced by PRL-receptor activation in GH3 cells. | 2003 Mar |
|
Selective control of the estrous cycle of the dog through suppression of estrus and reduction of the length of anestrus. | 2003 Mar |
|
[Macroadenoma of the pituitary gland with moderate hyperprolactinaemia]. | 2003 Mar 28 |
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12464354
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).
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C66884
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NCI_THESAURUS |
C38149
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WHO-VATC |
QG02CB03
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WHO-ATC |
N04BC06
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NDF-RT |
N0000007618
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LIVERTOX |
135
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WHO-VATC |
QN04BC06
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NDF-RT |
N0000175827
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WHO-ATC |
G02CB03
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NDF-RT |
N0000007618
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EMA VETERINARY ASSESSMENT REPORTS |
VELACTIS [SUSPENDED]
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CHEMBL1201087
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460
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C047047
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CABERGOLINE
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81409-90-7
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37
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C47428
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5860
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II-10
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DTXSID6022719
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47579
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3286
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1084306
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54746
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Cabergoline
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SUB06041MIG
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DB00248
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LL60K9J05T
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LL60K9J05T
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M2876
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PRIMARY | Merck Index |
ACTIVE MOIETY
METABOLITE (PARENT)
SALT/SOLVATE (PARENT)