bromocriptine Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
ergot alkaloid derivatives 403 25614-03-3

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • bromocriptine
  • bromocriptin
  • bromocryptine
  • ergolactin
  • 2-bromoergocriptine
  • bromocriptine mesylate
  • bromocriptine mesilate
A semisynthetic ergotamine alkaloid that is a dopamine D2 agonist. It suppresses prolactin secretion.
  • Molecular weight: 654.61
  • Formula: C32H40BrN5O5
  • CLOGP: 6.58
  • LIPINSKI: 2
  • HAC: 10
  • HDO: 3
  • TPSA: 118.21
  • ALOGS: -3.88
  • ROTB: 5

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
5 mg O
5 mg P
40 mg O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 0.80 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 2 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 2.19 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 28 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H

Approvals:

DateAgencyCompanyOrphan
June 28, 1978 FDA US PHARMS HOLDINGS I

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Blood prolactin increased 83.94 19.77 23 3414 3004 46679621
Neuroleptic malignant syndrome 82.60 19.77 31 3406 11091 46671534
Exposure during pregnancy 65.48 19.77 58 3379 108154 46574471
Visual pathway disorder 56.34 19.77 8 3429 27 46682598
Pituitary tumour 45.14 19.77 11 3426 904 46681721
Maternal exposure during pregnancy 43.09 19.77 45 3392 102504 46580121
Mediastinal fibrosis 41.65 19.77 6 3431 23 46682602
Gambling disorder 36.63 19.77 10 3427 1286 46681339
Pituitary tumour removal 35.91 19.77 5 3432 14 46682611
Prolactin-producing pituitary tumour 33.19 19.77 6 3431 113 46682512
Compulsive shopping 31.41 19.77 8 3429 787 46681838
Parkinson's disease 30.50 19.77 9 3428 1530 46681095
Pituitary tumour benign 29.72 19.77 9 3428 1672 46680953
Hypersexuality 29.70 19.77 7 3430 499 46682126
Body height increased 29.12 19.77 5 3432 69 46682556
Hyperprolactinaemia 28.59 19.77 10 3427 2922 46679703
Psychomotor hyperactivity 28.52 19.77 14 3423 9599 46673026
Pituitary haemorrhage 28.09 19.77 5 3432 86 46682539
Peripartum cardiomyopathy 26.42 19.77 5 3432 122 46682503
Catatonia 26.16 19.77 10 3427 3752 46678873
Brief psychotic disorder, with postpartum onset 25.51 19.77 4 3433 30 46682595
Muscle neoplasm 23.81 19.77 4 3433 48 46682577
Gallbladder neoplasm 23.59 19.77 4 3433 51 46682574
Tricuspid valve sclerosis 23.47 19.77 3 3434 3 46682622
Lymphatic system neoplasm 23.45 19.77 4 3433 53 46682572
Somatic delusion 23.39 19.77 6 3431 607 46682018
Arteriospasm coronary 22.95 19.77 9 3428 3612 46679013
Hemianopia heteronymous 22.57 19.77 4 3433 67 46682558
Galactorrhoea 22.54 19.77 9 3428 3788 46678837
Blood creatine phosphokinase increased 21.11 19.77 17 3420 27707 46654918
Pulmonary artery occlusion 20.53 19.77 3 3434 13 46682612
Alveolar lung disease 20.51 19.77 4 3433 115 46682510
Eating disorder 20.46 19.77 13 3424 14641 46667984
Genital swelling 19.86 19.77 4 3433 136 46682489

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Neuroleptic malignant syndrome 100.55 23.90 37 1675 16258 29934508
Gambling disorder 90.46 23.90 21 1691 1819 29948947
Serotonin syndrome 65.91 23.90 28 1684 17863 29932903
Stress cardiomyopathy 57.03 23.90 14 1698 1535 29949231
Muscle rigidity 54.85 23.90 21 1691 10240 29940526
Impulse-control disorder 53.35 23.90 13 1699 1382 29949384
Hypersexuality 37.79 23.90 10 1702 1477 29949289
Prolactin-producing pituitary tumour 33.46 23.90 5 1707 35 29950731
Borderline personality disorder 33.37 23.90 7 1705 378 29950388
Premature baby 32.99 23.90 17 1695 16674 29934092
Neonatal respiratory depression 32.55 23.90 7 1705 426 29950340
Cardiac valve disease 26.99 23.90 9 1703 2940 29947826
Blood creatine phosphokinase increased 26.25 23.90 21 1691 43827 29906939
Autonomic nervous system imbalance 24.61 23.90 8 1704 2413 29948353
Pneumonia aspiration 24.56 23.90 19 1693 37761 29913005
Blood prolactin increased 24.29 23.90 7 1705 1415 29949351

Pharmacologic Action:

SourceCodeDescription
ATC G02CB01 GENITO URINARY SYSTEM AND SEX HORMONES
OTHER GYNECOLOGICALS
OTHER GYNECOLOGICALS
Prolactine inhibitors
ATC N04BC01 NERVOUS SYSTEM
ANTI-PARKINSON DRUGS
DOPAMINERGIC AGENTS
Dopamine agonists
FDA CS M0007652 Ergolines
CHEBI has role CHEBI:48407 antiparkinson agent
CHEBI has role CHEBI:49020 hormone antagonists
CHEBI has role CHEBI:51065 agonista dopaminergico
CHEBI has role CHEBI:66956 antidyskinetic drugs
MeSH PA D018726 Anti-Dyskinesia Agents
MeSH PA D000978 Antiparkinson Agents
MeSH PA D002491 Central Nervous System Agents
MeSH PA D015259 Dopamine Agents
MeSH PA D018491 Dopamine Agonists
MeSH PA D006727 Hormone Antagonists
MeSH PA D018377 Neurotransmitter Agents
FDA EPC N0000175827 Ergot Derivative

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Postencephalitic parkinsonism indication 19972008 DOID:14332
Parkinson's disease indication 49049000 DOID:14330
Acromegaly indication 74107003 DOID:2449
Hyperprolactinemia indication 237662005 DOID:12700
Type 2 Diabetes Mellitus Treatment Adjunct indication
Neuroleptic malignant syndrome off-label use 15244003 DOID:14464
Hypertensive disorder contraindication 38341003 DOID:10763
Mild pre-eclampsia contraindication 41114007
Severe pre-eclampsia contraindication 46764007
Pregnancy-induced hypertension contraindication 48194001
Eclampsia in pregnancy contraindication 198992004
Cerebrovascular accident contraindication 230690007
Disease of liver contraindication 235856003 DOID:409
Breastfeeding (mother) contraindication 413712001
Disorder of coronary artery contraindication 414024009
Hypertensive urgency contraindication 443482000
Psychiatric Disturbance contraindication

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 11.98 acidic
pKa2 12.93 acidic
pKa3 5.98 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
D(2) dopamine receptor GPCR AGONIST Ki 9.70 WOMBAT-PK CHEMBL
Alpha-1B adrenergic receptor GPCR Ki 8.86 PDSP
5-hydroxytryptamine receptor 1D GPCR Ki 8 WOMBAT-PK
5-hydroxytryptamine receptor 6 GPCR AGONIST Ki 7.50 IUPHAR
D(4) dopamine receptor GPCR ANTAGONIST Ki 6.40 IUPHAR
D(1B) dopamine receptor GPCR AGONIST Ki 6.30 IUPHAR
D(1A) dopamine receptor GPCR AGONIST Ki 6.20 IUPHAR
Beta-1 adrenergic receptor GPCR Ki 5.86 DRUG MATRIX
Cytochrome P450 3A4 Enzyme IC50 5.70 DRUG MATRIX
Alpha-1D adrenergic receptor GPCR Ki 8.55 DRUG MATRIX
D(3) dopamine receptor GPCR AGONIST Ki 7.50 WOMBAT-PK
Alpha-1A adrenergic receptor GPCR Ki 8.38 WOMBAT-PK
5-hydroxytryptamine receptor 2B GPCR Ki 7.30 WOMBAT-PK
5-hydroxytryptamine receptor 1A GPCR Ki 7.90 WOMBAT-PK
Alpha-2A adrenergic receptor GPCR Ki 8 WOMBAT-PK
Alpha-2C adrenergic receptor GPCR Ki 7.60 WOMBAT-PK
5-hydroxytryptamine receptor 1B GPCR Ki 6.50 WOMBAT-PK
Alpha-2B adrenergic receptor GPCR Ki 7.50 WOMBAT-PK
5-hydroxytryptamine receptor 2C GPCR Ki 6.10 WOMBAT-PK
5-hydroxytryptamine receptor 2A GPCR Ki 7 WOMBAT-PK
Beta-2 adrenergic receptor GPCR Ki 6.13 PDSP
Androgen receptor Transcription factor Ki 5.82 DRUG MATRIX
Alpha-1B adrenergic receptor GPCR Ki 8.71 DRUG MATRIX
5-hydroxytryptamine receptor 1B GPCR Ki 7.33 DRUG MATRIX
Dopamine receptor GPCR IC50 7.55 CHEMBL
Adrenergic receptor alpha-2 GPCR IC50 6.29 CHEMBL
Cerebral cortex alpha adrenergic receptor GPCR IC50 6.29 CHEMBL
D(2) dopamine receptor GPCR Kd 8.40 CHEMBL
5-hydroxytryptamine receptor 1A GPCR IC50 8.25 CHEMBL
Alpha-1A adrenergic receptor GPCR IC50 8.16 CHEMBL
Vesicular glutamate transporter 3 Unclassified IC50 4.66 CHEMBL
5-hydroxytryptamine receptor 7 GPCR AGONIST Ki 8 IUPHAR
5-hydroxytryptamine receptor 6 GPCR AGONIST Ki 7.50 IUPHAR

External reference:

IDSource
4019639 VUID
N0000147732 NUI
D00780 KEGG_DRUG
22260-51-1 SECONDARY_CAS_RN
4018752 VANDF
4019639 VANDF
C0006230 UMLSCUI
CHEBI:3181 CHEBI
08Y PDB_CHEM_ID
CHEMBL493 ChEMBL_ID
CHEMBL1200503 ChEMBL_ID
CHEMBL311816 ChEMBL_ID
DB01200 DRUGBANK_ID
D001971 MESH_DESCRIPTOR_UI
3365 INN_ID
31101 PUBCHEM_CID
35 IUPHAR_LIGAND_ID
3A64E3G5ZO UNII
142426 RXNORM
10007 MMSL
4300 MMSL
d00178 MMSL
002117 NDDF
002118 NDDF
116656002 SNOMEDCT_US
387039007 SNOMEDCT_US
46293006 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Bromocriptine Mesylate HUMAN PRESCRIPTION DRUG LABEL 1 0378-2042 TABLET 2.50 mg ORAL ANDA 22 sections
Bromocriptine Mesylate HUMAN PRESCRIPTION DRUG LABEL 1 0378-7096 CAPSULE 5 mg ORAL ANDA 22 sections
Bromocriptine mesylate HUMAN PRESCRIPTION DRUG LABEL 1 0574-0106 TABLET 2.50 mg ORAL ANDA 22 sections
Bromocriptine mesylate HUMAN PRESCRIPTION DRUG LABEL 1 0781-5325 TABLET 2.50 mg ORAL ANDA 18 sections
Parlodel HUMAN PRESCRIPTION DRUG LABEL 1 30698-201 CAPSULE, GELATIN COATED 5 mg ORAL NDA 21 sections
Parlodel HUMAN PRESCRIPTION DRUG LABEL 1 30698-202 TABLET 2.50 mg ORAL NDA 21 sections
Bromocriptine Mesylate HUMAN PRESCRIPTION DRUG LABEL 1 54868-5667 TABLET 2.50 mg ORAL ANDA 22 sections
Bromocriptine Mesylate HUMAN PRESCRIPTION DRUG LABEL 1 60687-286 TABLET 2.50 mg ORAL ANDA 18 sections
BROMOCRIPTINE MESYLATE HUMAN PRESCRIPTION DRUG LABEL 1 63304-158 CAPSULE 5 mg ORAL NDA 14 sections
BROMOCRIPTINE MESYLATE HUMAN PRESCRIPTION DRUG LABEL 1 63304-962 TABLET 2.50 mg ORAL NDA 14 sections
Bromocriptine mesylate HUMAN PRESCRIPTION DRUG LABEL 1 65841-654 CAPSULE 5 mg ORAL ANDA 1 sections
CYCLOSET HUMAN PRESCRIPTION DRUG LABEL 1 68012-258 TABLET 0.80 mg ORAL NDA 30 sections
Bromocriptine mesylate HUMAN PRESCRIPTION DRUG LABEL 1 68151-1305 TABLET 2.50 mg ORAL ANDA 23 sections
Bromocriptine mesylate HUMAN PRESCRIPTION DRUG LABEL 1 68382-110 CAPSULE 5 mg ORAL ANDA 13 sections
CYCLOSET HUMAN PRESCRIPTION DRUG LABEL 1 73515-123 TABLET 0.80 mg ORAL NDA 28 sections