dihydroergotamine indications/contra

Stem definitionDrug idCAS RN
ergot alkaloid derivatives 888 511-12-6

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • dihydroergotamine mesilate
  • dihydroergotamine tartrate
  • dihydroergotamine
  • 9,10-Dihydroergotamine
  • dihydroergotamine mesylate
A 9,10alpha-dihydro derivative of ERGOTAMINE. It is used as a vasoconstrictor, specifically for the therapy of MIGRAINE DISORDERS.
  • Molecular weight: 583.69
  • Formula: C33H37N5O5
  • CLOGP: 4.77
  • LIPINSKI: 1
  • HAC: 10
  • HDO: 3
  • TPSA: 118.21
  • ALOGS: -3.41
  • ROTB: 4

Drug dosage:

DoseUnitRoute
1 mg N
4 mg O
4 mg P

Approvals:

DateAgencyCompanyOrphan
April 12, 1946 FDA VALEANT

FDA Adverse Event Reporting System

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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
Medication error 41.93 37.21 10 102 11861 3373886

Pharmacologic Action:

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SourceCodeDescription
ATC N02CA01 NERVOUS SYSTEM
ANALGESICS
ANTIMIGRAINE PREPARATIONS
Ergot alkaloids
ATC N02CA51 NERVOUS SYSTEM
ANALGESICS
ANTIMIGRAINE PREPARATIONS
Ergot alkaloids
FDA EPC N0000175766 Ergotamine Derivative
FDA Chemical/Ingredient N0000007621 Ergotamines
MeSH PA D000700 Analgesics
MeSH PA D018712 Analgesics, Non-Narcotic
MeSH PA D002317 Cardiovascular Agents
MeSH PA D002491 Central Nervous System Agents
MeSH PA D015259 Dopamine Agents
MeSH PA D018491 Dopamine Agonists
MeSH PA D018377 Neurotransmitter Agents
MeSH PA D018373 Peripheral Nervous System Agents
MeSH PA D018689 Sensory System Agents
MeSH PA D014662 Vasoconstrictor Agents
CHEBI has role CHEBI:35941 serotonergic agonist
CHEBI has role CHEBI:35481 non-narcotic analgesic
CHEBI has role CHEBI:50514 vasoconstrictor agent
CHEBI has role CHEBI:51065 dopamine agonist
CHEBI has role CHEBI:66991 sympatholytic agent

Drug Use (View source of the data)

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DiseaseRelationSNOMED_IDDOID
Migraine indication 37796009 DOID:6364
Vascular headache indication 128187005
Cluster headache syndrome indication 193031009
Bacterial septicemia contraindication 10001005
Vascular surgery procedure contraindication 30904006
Hypertensive disorder contraindication 38341003 DOID:10763
Acute nephropathy contraindication 58574008
Hepatic failure contraindication 59927004
Prinzmetal angina contraindication 87343002
Pregnancy, function contraindication 289908002
Cardiovascular event risk contraindication 395112001
Peripheral vascular disease contraindication 400047006
Breastfeeding (mother) contraindication 413712001
Disorder of coronary artery contraindication 414024009
Porphyria contraindication 418470004 DOID:13268
Hypertensive urgency contraindication 443482000

Acid dissociation constants calculated using MoKa v3.0.0

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Dissociation levelDissociation constantType (acidic/basic)
pKa1 11.58 acidic
pKa2 12.7 acidic
pKa3 13.43 acidic
pKa4 7.56 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

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TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
5-hydroxytryptamine receptor 1D GPCR AGONIST Ki 9.90 IUPHAR CHEMBL
5-hydroxytryptamine receptor 1B GPCR AGONIST Ki 9.20 IUPHAR
5-hydroxytryptamine receptor 1F GPCR AGONIST Ki 7.10 IUPHAR
5-hydroxytryptamine receptor 7 GPCR ANTAGONIST Ki 8 IUPHAR
5-hydroxytryptamine receptor 1E GPCR AGONIST Ki 5.60 IUPHAR
D(1A) dopamine receptor GPCR Ki 5.92 DRUG MATRIX
D(2) dopamine receptor GPCR Ki 8.53 DRUG MATRIX
Alpha-2A adrenergic receptor GPCR Ki 9.41 DRUG MATRIX
Cytochrome P450 3A4 Enzyme IC50 5.30 DRUG MATRIX
5-hydroxytryptamine receptor 1A GPCR Ki 9.42 DRUG MATRIX
5-hydroxytryptamine receptor 2A GPCR Ki 8.64 DRUG MATRIX
5-hydroxytryptamine receptor 2B GPCR Ki 8.36 DRUG MATRIX
5-hydroxytryptamine receptor 2C GPCR Ki 7.33 DRUG MATRIX
Alpha-2B adrenergic receptor GPCR Ki 8.75 DRUG MATRIX
D(3) dopamine receptor GPCR Ki 8.74 DRUG MATRIX
Alpha-2C adrenergic receptor GPCR Ki 8.82 DRUG MATRIX
Alpha-1D adrenergic receptor GPCR Ki 8.69 DRUG MATRIX
5-hydroxytryptamine receptor 5A GPCR WOMBAT-PK
Alpha-1B adrenergic receptor GPCR WOMBAT-PK
Alpha-1A adrenergic receptor GPCR WOMBAT-PK
Solute carrier family 22 member 2 Transporter IC50 4.30 CHEMBL
Multidrug and toxin extrusion protein 2 Transporter IC50 4.90 CHEMBL
Multidrug and toxin extrusion protein 1 Transporter IC50 5.55 CHEMBL
5-hydroxytryptamine receptor 4 GPCR Ki 6.80 DRUG MATRIX
Alpha-1B adrenergic receptor GPCR Ki 8.35 DRUG MATRIX
5-hydroxytryptamine receptor 1B GPCR Ki 9.42 DRUG MATRIX
Adrenergic receptor alpha-2 GPCR IC50 8.43 CHEMBL
Gastrin/cholecystokinin type B receptor GPCR IC50 4.64 CHEMBL
5-hydroxytryptamine receptor 1A GPCR IC50 9.18 CHEMBL
Alpha-1A adrenergic receptor GPCR IC50 8.30 CHEMBL
5-hydroxytryptamine receptor 6 GPCR ANTAGONIST Ki 8.30 IUPHAR
5-hydroxytryptamine receptor 7 GPCR ANTAGONIST Ki 6.80 IUPHAR

External reference:

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IDSource
DB00320 DRUGBANK_ID
121 IUPHAR_LIGAND_ID
C0771983 UMLSCUI
D02211 KEGG_DRUG
436O5HM03C UNII
2022 INN_ID
5989-77-5 SECONDARY_CAS_RN
3418 RXNORM
387267005 SNOMEDCT_US
48875009 SNOMEDCT_US
d00211 MMSL
4019721 VANDF
N0000147813 NDFRT
N0000005941 NDFRT
004529 NDDF
CHEMBL1732 ChEMBL_ID
CHEMBL1200517 ChEMBL_ID
D004087 MESH_DESCRIPTOR_UI
10531 PUBCHEM_CID
CHEBI:4562 CHEBI
2GM PDB_CHEM_ID

Pharmaceutical products:

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ProductCategoryIngredientsNDCFormQuantityRoute MarketingLabel
Dihydroergotamine Mesylate HUMAN PRESCRIPTION DRUG LABEL 1 0143-9273 INJECTION 1 mg INTRAMUSCULAR ANDA 14 sections
Migranal HUMAN PRESCRIPTION DRUG LABEL 1 0187-0245 SPRAY 4 mg NASAL NDA 16 sections
Dihydroergotamine Mesylate HUMAN PRESCRIPTION DRUG LABEL 1 0574-0850 INJECTION, SOLUTION 1 mg SUBCUTANEOUS ANDA 14 sections
D.H.E. 45 HUMAN PRESCRIPTION DRUG LABEL 1 66490-041 INJECTION, SOLUTION 1 mg INTRAVENOUS NDA 15 sections
Dihydroergotamine Mesylate HUMAN PRESCRIPTION DRUG LABEL 1 68682-357 SPRAY 4 mg NASAL NDA authorized generic 16 sections