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

Stem definitionDrug idCAS RN
1043 113-15-5

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • ergotamine
  • ergotamin
  • ergotamine tartrate
  • ergotaminine
A vasoconstrictor found in ergot of Central Europe. It is a serotonin agonist that has been used as an oxytocic agent and in the treatment of MIGRAINE DISORDERS.
  • Molecular weight: 581.67
  • Formula: C33H35N5O5
  • CLOGP: 4.66
  • LIPINSKI: 1
  • HAC: 10
  • HDO: 3
  • TPSA: 118.21
  • ALOGS: -3.42
  • ROTB: 4

  • Status: OFP

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

Drug dosage:

DoseUnitRoute
4 mg Inhal.aerosol
4 mg O
4 mg P
4 mg R
4 mg SL
4 mg O
4 mg O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 2 mg/mL Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 0.15 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 2 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 3.60 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 15 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.02 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 2.10 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Nov. 26, 1948 FDA

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
Ergot poisoning 381.22 35.28 44 548 185 46685285
Drug interaction 115.21 35.28 54 538 203040 46482430
Stress cardiomyopathy 41.05 35.28 11 581 7773 46677697

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
Ergot poisoning 141.38 58.99 16 280 73 29952109

Pharmacologic Action:

SourceCodeDescription
ATC N02CA02 NERVOUS SYSTEM
ANALGESICS
ANTIMIGRAINE PREPARATIONS
Ergot alkaloids
ATC N02CA52 NERVOUS SYSTEM
ANALGESICS
ANTIMIGRAINE PREPARATIONS
Ergot alkaloids
ATC N02CA72 NERVOUS SYSTEM
ANALGESICS
ANTIMIGRAINE PREPARATIONS
Ergot alkaloids
FDA CS M0007665 Ergotamines
FDA EPC N0000175766 Ergotamine Derivative
MeSH PA D018663 Adrenergic Agents
MeSH PA D000322 Adrenergic Agonists
MeSH PA D058646 Adrenergic alpha-1 Receptor Agonists
MeSH PA D000316 Adrenergic alpha-Agonists
MeSH PA D000700 Analgesics
MeSH PA D018712 Analgesics, Non-Narcotic
MeSH PA D002317 Cardiovascular Agents
MeSH PA D002491 Central Nervous System Agents
MeSH PA D018377 Neurotransmitter Agents
MeSH PA D010120 Oxytocics
MeSH PA D018373 Peripheral Nervous System Agents
MeSH PA D012102 Reproductive Control Agents
MeSH PA D018689 Sensory System Agents
MeSH PA D018490 Serotonin Agents
MeSH PA D017366 Serotonin Receptor Agonists
MeSH PA D014662 Vasoconstrictor Agents
CHEBI has role CHEBI:25442 mycotoxins
CHEBI has role CHEBI:35569 alpha-adrenergic receptor agonist
CHEBI has role CHEBI:35941 serotonergic agonists

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Migraine indication 37796009 DOID:6364
Vascular headache indication 128187005
Cluster headache syndrome indication 193031009
Cluster Headache Prevention indication
Brain damage contraindication 2470005
Necrotizing enterocolitis in fetus OR newborn contraindication 2707005
Tachyarrhythmia contraindication 6285003
Suicidal thoughts contraindication 6471006
Urinary tract obstruction contraindication 7163005 DOID:5200
Alcoholism contraindication 7200002
Hyperammonemia contraindication 9360008
Bacterial septicemia contraindication 10001005 DOID:0040085
Peptic ulcer contraindication 13200003 DOID:750
Chronic obstructive lung disease contraindication 13645005 DOID:3083
Hepatic encephalopathy contraindication 13920009 DOID:13413
Severe chronic ulcerative colitis contraindication 14311001
Toxic megacolon contraindication 28536002 DOID:1770
Atony of colon contraindication 29479008
Vascular surgery procedure contraindication 30904006
Hyperthyroidism contraindication 34486009 DOID:7998
Depressive disorder contraindication 35489007
Hypertensive disorder contraindication 38341003 DOID:10763
Complete trisomy 21 syndrome contraindication 41040004 DOID:14250
Hyperactive behavior contraindication 44548000
Conduction disorder of the heart contraindication 44808001
Achalasia of esophagus contraindication 45564002 DOID:9164
Chronic heart failure contraindication 48447003
Retroperitoneal fibrosis contraindication 49120005
Fibrosis of lung contraindication 51615001 DOID:3770
Paralytic ileus contraindication 55525008 DOID:8442
Peptic reflux disease contraindication 57643001
Acute nephropathy contraindication 58574008
Hepatic failure contraindication 59927004
Diarrhea contraindication 62315008
Thrombophlebitis contraindication 64156001 DOID:3875
Ulcerative colitis contraindication 64766004 DOID:8577
Poisoning by phenobarbital contraindication 64921004
Drug AND/OR toxin-induced diarrhea contraindication 65979008
Substance abuse contraindication 66214007
Agoraphobia contraindication 70691001 DOID:593
Hepatic coma contraindication 72836002 DOID:12550
Sleep apnea contraindication 73430006 DOID:0050847
Spastic paralysis contraindication 78403003
Disturbance of salivary secretion contraindication 78948009
Hiatal hernia contraindication 84089009 DOID:12642
Prinzmetal angina contraindication 87343002
Kidney disease contraindication 90708001 DOID:557
Myasthenia gravis contraindication 91637004 DOID:437
Gastrointestinal obstruction contraindication 126765001
Seizure disorder contraindication 128613002
Autonomic dysreflexia contraindication 129618003
Bleeding contraindication 131148009
Obsessive-compulsive disorder contraindication 191736004 DOID:10933
Insomnia contraindication 193462001
Impaired renal function disorder contraindication 197663003
Myocardial dysfunction contraindication 233928007
Peripheral ischemia contraindication 233958001
Disease of liver contraindication 235856003 DOID:409
Bladder outflow obstruction contraindication 236645006
Sepsis syndrome contraindication 238150007
Pyloric obstruction contraindication 244815007
Sleep automatism contraindication 247962006
Raynaud's phenomenon contraindication 266261006
Benign prostatic hyperplasia contraindication 266569009
Dyspnea contraindication 267036007
Retention of urine contraindication 267064002
Anemia contraindication 271737000 DOID:2355
Drowsy contraindication 271782001
Cerebral ischemia contraindication 287731003
Pregnancy, function contraindication 289908002
Thrombocytopenic disorder contraindication 302215000 DOID:1588
Neutropenic disorder contraindication 303011007 DOID:1227
Panic disorder contraindication 371631005 DOID:594
Angle-closure glaucoma contraindication 392291006 DOID:13550
Cardiovascular event risk contraindication 395112001
Gastric ulcer contraindication 397825006 DOID:10808
Peripheral vascular disease contraindication 400047006
Respiratory insufficiency contraindication 409623005
Breastfeeding (mother) contraindication 413712001
Chronic lung disease contraindication 413839001
Disorder of coronary artery contraindication 414024009
Myocardial ischemia contraindication 414795007 DOID:3393
Myocardial infarction in recovery phase contraindication 418044006
Porphyria contraindication 418470004
Fibrosis of pleura contraindication 442110002
Hypertensive urgency contraindication 443482000
Acute exacerbation of asthma contraindication 708038006
Severe Pruritus contraindication
Ergot Alkaloid Toxicity contraindication

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 11.58 acidic
pKa2 12.56 acidic
pKa3 13.71 acidic
pKa4 6.51 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
5-hydroxytryptamine receptor 1D GPCR AGONIST Ki 9.10 CHEMBL CHEMBL
5-hydroxytryptamine receptor 2B GPCR AGONIST Ki 8.90 IUPHAR
5-hydroxytryptamine receptor 6 GPCR AGONIST Ki 8.60 IUPHAR
5-hydroxytryptamine receptor 1E GPCR AGONIST Ki 6.30 IUPHAR
5-hydroxytryptamine receptor 2A GPCR AGONIST Ki 9 IUPHAR
5-hydroxytryptamine receptor 2C GPCR AGONIST Ki 8.70 IUPHAR
5-hydroxytryptamine receptor 1F GPCR AGONIST Ki 6.80 IUPHAR
Beta-1 adrenergic receptor GPCR Ki 5.62 DRUG MATRIX
Beta-2 adrenergic receptor GPCR Ki 5.72 DRUG MATRIX
D(1A) dopamine receptor GPCR Ki 6.06 DRUG MATRIX
D(2) dopamine receptor GPCR Ki 8.84 DRUG MATRIX
Alpha-2A adrenergic receptor GPCR Ki 9.10 DRUG MATRIX
Cytochrome P450 3A4 Enzyme IC50 6 DRUG MATRIX
5-hydroxytryptamine receptor 1A GPCR Ki 9.35 DRUG MATRIX
Alpha-2B adrenergic receptor GPCR Ki 8.75 DRUG MATRIX
D(3) dopamine receptor GPCR Ki 8.84 DRUG MATRIX
Alpha-2C adrenergic receptor GPCR Ki 8.74 DRUG MATRIX
Alpha-1D adrenergic receptor GPCR Ki 8.49 DRUG MATRIX
Tyrosine-protein kinase Lck Kinase IC50 5.19 DRUG MATRIX
Tyrosine-protein kinase Fyn Kinase IC50 5.50 DRUG MATRIX
Thromboxane-A synthase Enzyme IC50 5.51 DRUG MATRIX
Alpha-1A adrenergic receptor GPCR AGONIST WOMBAT-PK
D(1B) dopamine receptor GPCR Ki 6.77 PDSP
Muscarinic acetylcholine receptor M1 GPCR Ki 6.06 PDSP
Muscarinic acetylcholine receptor M2 GPCR Ki 6.04 PDSP
5-hydroxytryptamine receptor 1B GPCR Ki 8.68 CHEMBL
5-hydroxytryptamine receptor 5A GPCR Ki 7.85 CHEMBL
5-hydroxytryptamine receptor 6 GPCR AGONIST Ki 8.60 IUPHAR
5-hydroxytryptamine receptor 4 GPCR Ki 6.58 DRUG MATRIX
Alpha-1B adrenergic receptor GPCR Ki 8.34 DRUG MATRIX
5-hydroxytryptamine receptor 1B GPCR Ki 10.04 DRUG MATRIX
Cholecystokinin A receptor GPCR IC50 4.47 CHEMBL
Adenylate cyclase Unclassified IC50 4.15 CHEMBL
Gastrin/cholecystokinin type B receptor GPCR IC50 4.77 CHEMBL
5-hydroxytryptamine receptor 1A GPCR IC50 9.11 CHEMBL
Alpha-1A adrenergic receptor GPCR IC50 8.09 CHEMBL
5-hydroxytryptamine receptor 2C GPCR AGONIST Ki 7.90 IUPHAR
5-hydroxytryptamine receptor 2A GPCR AGONIST Ki 8 IUPHAR
5-hydroxytryptamine receptor 1F Unclassified AGONIST IC50 7.30 IUPHAR
5-hydroxytryptamine receptor 7 GPCR ANTAGONIST Ki 7.30 IUPHAR
5-hydroxytryptamine receptor 5A Unclassified ANTAGONIST Ki 8.40 IUPHAR
5-hydroxytryptamine receptor 5A Unclassified ANTAGONIST Ki 8.20 IUPHAR

External reference:

IDSource
4022407 VUID
N0000020412 NUI
D00679 KEGG_DRUG
379-79-3 SECONDARY_CAS_RN
4018515 VANDF
4022407 VANDF
C0014710 UMLSCUI
CHEBI:64318 CHEBI
ERM PDB_CHEM_ID
CHEMBL442 ChEMBL_ID
CHEMBL2448612 ChEMBL_ID
DB00696 DRUGBANK_ID
D004878 MESH_DESCRIPTOR_UI
8223 PUBCHEM_CID
149 IUPHAR_LIGAND_ID
391 INN_ID
PR834Q503T UNII
4025 RXNORM
44346 MMSL
4674 MMSL
d00222 MMSL
000678 NDDF
004526 NDDF
32647002 SNOMEDCT_US
395975005 SNOMEDCT_US
396046007 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
ERGOTAMINE HUMAN PRESCRIPTION DRUG LABEL 2 0143-2120 TABLET, FILM COATED 1 mg ORAL ANDA 22 sections
MIGERGOT HUMAN PRESCRIPTION DRUG LABEL 2 0713-0166 SUPPOSITORY 2 mg RECTAL ANDA 14 sections
Cafergot HUMAN PRESCRIPTION DRUG LABEL 2 0781-5405 TABLET, FILM COATED 1 mg ORAL ANDA 23 sections
Ergomar HUMAN PRESCRIPTION DRUG LABEL 1 10802-1202 TABLET, ORALLY DISINTEGRATING 2 mg SUBLINGUAL ANDA 24 sections
ergotamine tartrate and caffeine HUMAN PRESCRIPTION DRUG LABEL 2 24470-917 TABLET, FILM COATED 1 mg ORAL ANDA 24 sections
ergotamine tartrate and caffeine HUMAN PRESCRIPTION DRUG LABEL 2 46672-198 TABLET, FILM COATED 1 mg ORAL ANDA 24 sections
Ergomar Sublingual HUMAN PRESCRIPTION DRUG LABEL 1 70720-120 TABLET 2 mg ORAL ANDA 25 sections
Migergot HUMAN PRESCRIPTION DRUG LABEL 2 75987-090 SUPPOSITORY 2 mg RECTAL ANDA 22 sections