astemizole indications/contra

Stem definitionDrug idCAS RN
antihistaminics 249 68844-77-9

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • R 43 512
  • astemizole
  • astemisan
  • hismanal
  • histazol
Antihistamine drug now withdrawn from the market in many countries because of rare but potentially fatal side effects.
  • Molecular weight: 458.58
  • Formula: C28H31FN4O
  • CLOGP: 5.84
  • LIPINSKI: 1
  • HAC: 5
  • HDO: 1
  • TPSA: 42.32
  • ALOGS: -5.58
  • ROTB: 8

Drug dosage:

DoseUnitRoute
10 mg O

Approvals:

DateAgencyCompanyOrphan
Dec. 31, 1988 FDA

FDA Adverse Event Reporting System

None

Pharmacologic Action:

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SourceCodeDescription
ATC R06AX11 RESPIRATORY SYSTEM
ANTIHISTAMINES FOR SYSTEMIC USE
ANTIHISTAMINES FOR SYSTEMIC USE
Other antihistamines for systemic use
MeSH PA D018926 Anti-Allergic Agents
MeSH PA D018494 Histamine Agents
MeSH PA D006633 Histamine Antagonists
MeSH PA D006634 Histamine H1 Antagonists
MeSH PA D039563 Histamine H1 Antagonists, Non-Sedating
MeSH PA D018377 Neurotransmitter Agents
CHEBI has role CHEBI:37955 H1-receptor antagonist
CHEBI has role CHEBI:50857 anti-allergic agent

Drug Use (View source of the data)

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DiseaseRelationSNOMED_IDDOID
Allergic rhinitis indication 61582004
Sneezing indication 76067001
Chronic idiopathic urticaria indication 302162004
Allergic conjunctivitis indication 473460002 DOID:11204
Urticaria off-label use 126485001

Acid dissociation constants calculated using MoKa v3.0.0

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Dissociation levelDissociation constantType (acidic/basic)
pKa1 8.47 Basic
pKa2 5.81 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
Histamine H1 receptor GPCR ANTAGONIST A2 8.58 WOMBAT-PK SCIENTIFIC LITERATURE
Beta-1 adrenergic receptor GPCR Ki 5.00 DRUG MATRIX
Mu-type opioid receptor GPCR Ki 6.22 DRUG MATRIX
D(1A) dopamine receptor GPCR Ki 5.70 DRUG MATRIX
D(2) dopamine receptor GPCR Ki 5.82 DRUG MATRIX
Alpha-2A adrenergic receptor GPCR Ki 5.74 DRUG MATRIX
Sigma non-opioid intracellular receptor 1 Membrane receptor Ki 6.03 DRUG MATRIX
Sodium-dependent serotonin transporter Transporter Ki 6.15 DRUG MATRIX
Sodium-dependent noradrenaline transporter Transporter Ki 5.87 DRUG MATRIX
5-hydroxytryptamine receptor 1A GPCR Ki 6.36 DRUG MATRIX
5-hydroxytryptamine receptor 2A GPCR Ki 8.25 DRUG MATRIX
5-hydroxytryptamine receptor 2B GPCR Ki 8.13 DRUG MATRIX
5-hydroxytryptamine receptor 2C GPCR Ki 7.03 DRUG MATRIX
5-hydroxytryptamine receptor 6 GPCR Ki 5.82 DRUG MATRIX
Alpha-2B adrenergic receptor GPCR Ki 5.76 DRUG MATRIX
D(3) dopamine receptor GPCR Ki 6.83 DRUG MATRIX
Histamine H2 receptor GPCR Ki 5.78 DRUG MATRIX
Muscarinic acetylcholine receptor M1 GPCR Ki 6.59 DRUG MATRIX
Muscarinic acetylcholine receptor M2 GPCR Ki 6.30 DRUG MATRIX
Muscarinic acetylcholine receptor M3 GPCR Ki 6.75 DRUG MATRIX
Muscarinic acetylcholine receptor M4 GPCR Ki 6.59 DRUG MATRIX
Muscarinic acetylcholine receptor M5 GPCR Ki 6.30 DRUG MATRIX
Beta-3 adrenergic receptor GPCR Ki 5.22 DRUG MATRIX
Alpha-2C adrenergic receptor GPCR Ki 6.55 DRUG MATRIX
Sodium-dependent dopamine transporter Transporter Ki 6.10 DRUG MATRIX
Adenosine receptor A3 GPCR Ki 4.78 DRUG MATRIX
D(4) dopamine receptor GPCR Ki 5.67 DRUG MATRIX
Alpha-1D adrenergic receptor GPCR Ki 8.00 DRUG MATRIX
5-hydroxytryptamine receptor 3A Ion channel Ki 7.02 DRUG MATRIX
Kappa-type opioid receptor GPCR Ki 5.58 DRUG MATRIX
Delta-type opioid receptor GPCR Ki 5.34 DRUG MATRIX
Epidermal growth factor receptor Kinase IC50 5.22 DRUG MATRIX
Substance-P receptor GPCR Ki 5.06 DRUG MATRIX
Tyrosine-protein kinase Lck Kinase IC50 4.70 DRUG MATRIX
Tyrosine-protein kinase Fyn Kinase IC50 5.55 DRUG MATRIX
Receptor tyrosine-protein kinase erbB-2 Kinase IC50 4.88 DRUG MATRIX
Substance-K receptor GPCR Ki 6.00 DRUG MATRIX
Sodium/nucleoside cotransporter 1 Transporter Ki 5.31 DRUG MATRIX
Melanocortin receptor 4 GPCR Ki 4.87 DRUG MATRIX
Melanocortin receptor 5 GPCR Ki 5.67 DRUG MATRIX
Melanocortin receptor 3 GPCR Ki 4.87 DRUG MATRIX
Calmodulin Cytosolic other IC50 6 WOMBAT-PK
ATP-binding cassette sub-family G member 2 Transporter WOMBAT-PK
Multidrug resistance protein 1 Transporter IC50 6.05 WOMBAT-PK
Cytochrome P450 3A4 Enzyme IC50 5.48 WOMBAT-PK
Potassium voltage-gated channel subfamily H member 2 Ion channel IC50 9.05 WOMBAT-PK
Histamine H4 receptor GPCR Ki 5.10 CHEMBL
Somatostatin receptor type 5 GPCR Ki 5.39 CHEMBL
Multidrug and toxin extrusion protein 1 Transporter IC50 4.58 CHEMBL
Polycomb protein EED Unclassified IC50 4.03 CHEMBL
Glycine receptor subunit alpha-1 Ion channel EC50 5.38 CHEMBL
Potassium voltage-gated channel subfamily H member 1 Ion channel IC50 6.70 IUPHAR
Alpha-1B adrenergic receptor GPCR Ki 7.02 DRUG MATRIX
5-hydroxytryptamine receptor 1B GPCR Ki 6.20 DRUG MATRIX
Membrane-associated progesterone receptor component 1 Membrane receptor Ki 6.73 DRUG MATRIX
Protein farnesyltransferase Enzyme IC50 8.70 CHEMBL
5-hydroxytryptamine receptor 1A GPCR IC50 6.12 CHEMBL
Alpha-1A adrenergic receptor GPCR IC50 7.62 CHEMBL

External reference:

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IDSource
2603 IUPHAR_LIGAND_ID
4019379 VUID
N0000147536 NUI
C0085170 UMLSCUI
D00234 KEGG_DRUG
7HU6337315 UNII
4755 INN_ID
DB00637 DRUGBANK_ID
CHEMBL296419 ChEMBL_ID
4019379 VANDF
N0000007383 NDFRT
N0000147536 NDFRT
003413 NDDF
42328 RXNORM
387333002 SNOMEDCT_US
59456005 SNOMEDCT_US
4224 MMSL
d00794 MMSL
2247 PUBCHEM_CID
D016589 MESH_DESCRIPTOR_UI
CHEBI:2896 CHEBI

Pharmaceutical products:

None