CABERGOLINE

Search structure
Trade Names:
Synonyms:
Status: Approved (1996)
Entry Type: Small molecule
Molecule Category: UNKNOWN
ATC: G02CB03
UNII: LL60K9J05T

Structure
InChI Key KORNTPPJEAJQIU-KJXAQDMKSA-N
Smile C=CCN1C[C@H](C(=O)N(CCCN(C)C)C(=O)NCC)C[C@@H]2c3cccc4[nH]cc(c34)C[C@H]21
InChI
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

Physicochemical Descriptors

Property Name Value
Molecular Formula C26H37N5O2
Molecular Weight 451.62
AlogP 3.19
Hydrogen Bond Acceptor 4.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 8.0
Polar Surface Area 71.68
Molecular species BASE
Aromatic Rings 2.0
Heavy Atoms 33.0

Pharmacology

Action Mechanism of Action Reference
AGONIST Dopamine D2 receptor agonist Wikipedia FDA
Primary Target
D2 receptor
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Monoamine receptor Serotonin receptor
13 - - 1 -

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Diabetes Mellitus 3 D003920 ClinicalTrials
Restless Legs Syndrome 3 D012148 ClinicalTrials
Ovarian Hyperstimulation Syndrome 3 D016471 ClinicalTrials
Acromegaly 3 D000172 ClinicalTrials
Pituitary ACTH Hypersecretion 2 D047748 ClinicalTrials
Infertility 2 D007246 ClinicalTrials
Cocaine-Related Disorders 2 D019970 ClinicalTrials
Endometriosis 2 D004715 ClinicalTrials
Paget Disease, Extramammary 2 D010145 ClinicalTrials
Substance-Related Disorders 1 D019966 ClinicalTrials
Obesity 1 D009765 ClinicalTrials
Breast Neoplasms 0 D001943 ClinicalTrials

Related Entries

Scaffolds

Side Effects from Label

Side effects Relative Frequency (%) Labels
Gastrointestinal disorders Nausea 43.3
Gastrointestinal disorders Nausea 29.9
Gastrointestinal disorders Nausea 28.5
Cardiac disorders Dizziness 27.0
Nervous system disorders Headache 26.8
Gastrointestinal disorders Nausea 26.8
Nervous system disorders Headache 26.2
Nervous system disorders Headache 26.0
Nervous system disorders Headache 25.6
Nervous system disorders Headache
Gastrointestinal disorders Nausea 25.0
Nervous system disorders Dyskinesia
Gastrointestinal disorders Constipation 22.7
Gastrointestinal disorders Nausea 20.7
Gastrointestinal disorders Nausea
Cardiac disorders Dizziness 18.7
Nervous system disorders Somnolence 18.3
Cardiac disorders Dizziness 18.2
Nervous system disorders Somnolence 17.5
Nervous system disorders Insomnia 17.3
Cardiac disorders Dizziness 17.2
Nervous system disorders Dyskinesia 16.4
Gastrointestinal disorders Nausea 16.4
Gastrointestinal disorders Constipation 15.4
Cardiac disorders Dizziness 14.9
Nervous system disorders Hypokinesia
Nervous system disorders Orthostatic hypotension 12.6
Psychiatric disorders Anxiety 11.1
General disorders and administration site conditions Hyperhidrosis 11.1
Nervous system disorders Insomnia 10.9
Cardiac disorders Dizziness
Gastrointestinal disorders Nausea
Nervous system disorders Orthostatic hypotension 10.5
Nervous system disorders Orthostatic hypotension 10.4
Cardiac disorders Dizziness 10.3
Gastrointestinal disorders Dry mouth 10.1
General disorders and administration site conditions Asthenia
Nervous system disorders Insomnia
Gastrointestinal disorders Constipation 9.52
Gastrointestinal disorders Dry mouth 9.5
Nervous system disorders Dyskinesia 9.1
Gastrointestinal disorders Constipation 9.09
Psychiatric disorders Anxiety 9.0
Psychiatric disorders Hallucination 9.0
General disorders and administration site conditions Asthenia 8.93
Psychiatric disorders Hallucination 8.6
Cardiac disorders Oedema peripheral 8.5
Cardiac disorders Dizziness 8.3
Gastrointestinal disorders Abdominal pain 8.23
Gastrointestinal disorders Gastrointestinal pain 8.23
Infections and infestations Influenza 8.2
Nervous system disorders Orthostatic hypotension 8.2
Nervous system disorders Insomnia 7.8
General disorders and administration site conditions Asthenia 7.79
General disorders and administration site conditions Fatigue 7.79
Gastrointestinal disorders Gastritis 7.6
Psychiatric disorders Sleep disorder 7.6
Nervous system disorders Insomnia 7.4
Gastrointestinal disorders Vomiting 7.2
General disorders and administration site conditions Asthenia 7.14
General disorders and administration site conditions Fatigue 7.14
Nervous system disorders Headache 7.1
Infections and infestations Influenza 7.1
Gastrointestinal disorders Dyspepsia 6.93
Gastrointestinal disorders Vomiting 6.93
Gastrointestinal disorders Constipation 6.79
Musculoskeletal and connective tissue disorders Arthralgia 6.7
General disorders and administration site conditions Decreased appetite 6.7
Gastrointestinal disorders Gastritis 6.7
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 6.7
Infections and infestations Bronchitis 6.6
Nervous system disorders Orthostatic hypotension
General disorders and administration site conditions Asthenia 6.49
Infections and infestations Bronchitis 6.3
Nervous system disorders Dyskinesia 6.3
Nervous system disorders Headache 5.9
Nervous system disorders Somnolence 5.9
General disorders and administration site conditions Asthenia 5.88
Musculoskeletal and connective tissue disorders Back pain 5.8
Nervous system disorders Confusional state 5.8
General disorders and administration site conditions Feeling abnormal 5.8
Infections and infestations Urinary tract infection 5.8
Musculoskeletal and connective tissue disorders Back pain 5.7
Infections and infestations Urinary tract infection 5.7
Vascular disorders Hypotension 5.5
Nervous system disorders Somnolence 5.5
Gastrointestinal disorders Abdominal pain 5.43
Gastrointestinal disorders Gastrointestinal pain 5.43
Psychiatric disorders Sleep disorder 5.4
Gastrointestinal disorders Abdominal pain 5.36
Gastrointestinal disorders Gastrointestinal pain 5.36
Nervous system disorders Somnolence 5.36
General disorders and administration site conditions Hyperhidrosis 5.2
Vascular disorders Hypertension 5.2
Cardiac disorders Oedema peripheral 5.2
Infections and infestations Upper respiratory tract infection 5.2
Gastrointestinal disorders Abdominal pain
Gastrointestinal disorders Abdominal pain 5.0
Psychiatric disorders Depression
Cardiac disorders Dizziness
Gastrointestinal disorders Gastrointestinal pain
Gastrointestinal disorders Gastrointestinal pain 5.0
General disorders and administration site conditions Hot flush
Reproductive system and breast disorders Menopausal symptoms
Nervous system disorders Somnolence
Gastrointestinal disorders Dyspepsia 4.98
Gastrointestinal disorders Constipation 4.9
Nervous system disorders Headache
Infections and infestations Upper respiratory tract infection
Psychiatric disorders Euphoric mood 4.8
Psychiatric disorders Hallucination 4.8
Cardiac disorders Palpitations 4.8
Nervous system disorders Confusional state 4.7
Psychiatric disorders Euphoric mood 4.7
General disorders and administration site conditions Feeling abnormal 4.7
Gastrointestinal disorders Vomiting 4.7
Nervous system disorders Hypokinesia 4.6
General disorders and administration site conditions Asthenia 4.52
General disorders and administration site conditions Fatigue 4.52
Gastrointestinal disorders Vomiting 4.5
Ear and labyrinth disorders Vertigo 4.33
General disorders and administration site conditions Decreased appetite 4.3
Gastrointestinal disorders Diarrhoea 4.3
Gastrointestinal disorders Dyspepsia 4.3
Psychiatric disorders Hallucination 4.3
Nervous system disorders Headache 4.3
Psychiatric disorders Nightmare 4.3
Cardiac disorders Palpitations 4.3
Infections and infestations Pneumonia 4.3
Infections and infestations Upper respiratory tract infection 4.3
Gastrointestinal disorders Vomiting 4.2
Gastrointestinal disorders Constipation
Ear and labyrinth disorders Vertigo 4.07
Gastrointestinal disorders Vomiting 4.07
General disorders and administration site conditions Asthenia 4.0
Nervous system disorders Orthostatic hypotension 4.0
Infections and infestations Rhinitis 3.9
Musculoskeletal and connective tissue disorders Arthropathy 3.8
General disorders and administration site conditions Asthenia 3.8
Nervous system disorders Confusional state 3.8
Gastrointestinal disorders Constipation 3.8
Nervous system disorders Dyskinesia 3.8
General disorders and administration site conditions Feeling abnormal 3.8
Musculoskeletal and connective tissue disorders Osteoarthritis 3.8
Nervous system disorders Orthostatic hypotension 3.57
Nervous system disorders Headache 3.5
Vascular disorders Hypotension 3.5
Reproductive system and breast disorders Breast pain 3.46
Cardiac disorders Oedema peripheral 3.4
General disorders and administration site conditions Pain 3.4
Nervous system disorders Confusional state 3.3
Cardiac disorders Dyspnoea 3.3
General disorders and administration site conditions Feeling abnormal 3.3
Psychiatric disorders Hallucination
Reproductive system and breast disorders Prostatic disorder 3.3
Psychiatric disorders Depression 3.17
Gastrointestinal disorders Diarrhoea 3.03
Cardiac disorders Oedema peripheral 3.0
Psychiatric disorders Depression 2.98
General disorders and administration site conditions Hot flush 2.71
Reproductive system and breast disorders Menopausal symptoms 2.71
General disorders and administration site conditions Pain 2.6
Nervous system disorders Paraesthesia 2.6
Gastrointestinal disorders Dyspepsia 2.38
Psychiatric disorders Nervousness 2.38
Psychiatric disorders Tension 2.38
Gastrointestinal disorders Vomiting 2.38
Reproductive system and breast disorders Breast pain 2.26
Gastrointestinal disorders Dry mouth 2.26
Nervous system disorders Paraesthesia 2.26
Nervous system disorders Somnolence 2.26
Psychiatric disorders Depression 2.16
Psychiatric disorders Nervousness 2.16
Cardiac disorders Palpitations 2.16
Nervous system disorders Somnolence 2.16
Psychiatric disorders Tension 2.16
Gastrointestinal disorders Diarrhoea 2.0
Gastrointestinal disorders Dry mouth 2.0
Gastrointestinal disorders Flatulence 2.0
Nervous system disorders Paraesthesia 2.0
Gastrointestinal disorders Diarrhoea 1.81
Gastrointestinal disorders Flatulence 1.81
General disorders and administration site conditions Pain 1.81
Vascular disorders Hypotension 1.73
Skin and subcutaneous tissue disorders Acne 1.36
Psychiatric disorders Anxiety 1.36
General disorders and administration site conditions Decreased appetite 1.36
Cardiac disorders Dizziness 1.36
Vascular disorders Hypotension 1.36
Nervous system disorders Insomnia 1.36
Nervous system disorders Loss of consciousness 1.36
Vascular disorders Shock 1.36
Cardiac disorders Syncope 1.36
Psychiatric disorders Anxiety 1.3
General disorders and administration site conditions Decreased appetite 1.3
Cardiac disorders Dizziness 1.3
Gastrointestinal disorders Flatulence 1.3
General disorders and administration site conditions Hot flush 1.3
Nervous system disorders Loss of consciousness 1.3
Reproductive system and breast disorders Menopausal symptoms 1.3
Vascular disorders Shock 1.3
Cardiac disorders Syncope 1.3
Reproductive system and breast disorders Breast pain 1.19
Reproductive system and breast disorders Dysmenorrhoea 1.19
General disorders and administration site conditions Hot flush 1.19
Reproductive system and breast disorders Menopausal symptoms 1.19
Nervous system disorders Paraesthesia 1.19
Ear and labyrinth disorders Vertigo 1.19
Eye disorders Visual impairment 1.19
Psychiatric disorders Anxiety 1.0
Nervous system disorders Disturbance in attention 1.0
Cardiac disorders Dizziness 1.0
Reproductive system and breast disorders Dysmenorrhoea 1.0
Cardiac disorders Gravitational oedema 1.0
Vascular disorders Hypotension 1.0
Nervous system disorders Loss of consciousness 1.0
Social circumstances Mental disability 1.0
Cardiac disorders Oedema peripheral 1.0
Cardiac disorders Palpitations 1.0
Skin and subcutaneous tissue disorders Pruritus 1.0
Infections and infestations Rhinitis 1.0
Vascular disorders Shock 1.0
Cardiac disorders Syncope 1.0
Musculoskeletal and connective tissue disorders Arthralgia 0.905
General disorders and administration site conditions Discomfort 0.905
Nervous system disorders Disturbance in attention 0.905
Reproductive system and breast disorders Dysmenorrhoea 0.905
General disorders and administration site conditions Feeling abnormal 0.905
Cardiac disorders Gravitational oedema 0.905
General disorders and administration site conditions Ill-defined disorder 0.905
General disorders and administration site conditions Influenza like illness 0.905
General disorders and administration site conditions Malaise 0.905
Social circumstances Mental disability 0.905
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 0.905
Psychiatric disorders Nervousness 0.905
Cardiac disorders Oedema peripheral 0.905
Cardiac disorders Palpitations 0.905
Eye disorders Periorbital oedema 0.905
Skin and subcutaneous tissue disorders Pruritus 0.905
Infections and infestations Rhinitis 0.905
Psychiatric disorders Tension 0.905
Gastrointestinal disorders Throat irritation 0.905
Gastrointestinal disorders Toothache 0.905
Eye disorders Visual impairment 0.905
Gastrointestinal disorders Dry mouth 0.866
Nervous system disorders Insomnia 0.866
Eye disorders Periorbital oedema 0.866
Eye disorders Visual impairment 0.866

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
Nervous system disorders
15.03
Psychiatric disorders
11.27
General disorders and administration site conditions
10.02
Vascular disorders
8.15
Cardiac disorders
7.3
Injury, poisoning and procedural complications
6.83
Investigations
4.86
Respiratory, thoracic and mediastinal disorders
4.41
Gastrointestinal disorders
4.4
Neoplasms benign, malignant and unspecified (incl cysts and polyps)
3.27
Endocrine disorders
3.14
Eye disorders
2.86
Musculoskeletal and connective tissue disorders
2.61
Metabolism and nutrition disorders
2.22
Reproductive system and breast disorders
2.13
Pregnancy, puerperium and perinatal conditions
2.08
Skin and subcutaneous tissue disorders
2.05

Cross References

Resources Reference
CAS NUMBER 81409-90-7
ChEBI 3286
ChEMBL CHEMBL1201087
DrugBank DB00248
DrugCentral 460
EPA CompTox DTXSID6022719
FDA SRS LL60K9J05T
Human Metabolome Database HMDB0014393
Guide to Pharmacology 37
KEGG C08187
PharmGKB PA448708
PubChem 54746
SureChEMBL SCHEMBL42292
ZINC ZINC000003800008
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