Structure via PubChem · Public domain (PubChem)
astemizole
Sign in to saveAlso known as 1-(p-fluorobenzyl)-2-{[1-(p-methoxyphenethyl)-4-piperidyl]amino}benzimidazole, 1-(p-fluorobenzyl)-2-({1-[2-(p-methoxyphenyl)ethyl]piperid-4-yl}amino)benzimidazole
Astemizole (marketed under the brand name Hismanal, developmental code R43512) was a second-generation antihistamine drug that has a long duration of action. Astemizole was discovered by Janssen Pharmaceutica in 1977. It was withdrawn from the market globally in 1999 because of rare but potentially fatal side effects (QTc interval prolongation and related arrhythmias due to hERG channel blockade).
Chemical data
- Formula
- C28H31FN4O
- Molecular weight
- 458.6 g/mol
- IUPAC name
- 1-[(4-fluorophenyl)methyl]-N-[1-[2-(4-methoxyphenyl)ethyl]piperidin-4-yl]benzimidazol-2-amine
- SMILES
- COC1=CC=C(C=C1)CCN2CCC(CC2)NC3=NC4=CC=CC=C4N3CC5=CC=C(C=C5)F
- InChIKey
- GXDALQBWZGODGZ-UHFFFAOYSA-N
- XLogP
- 6
- Polar surface area
- 42.3 Ų
- H-bond donors
- 1
- H-bond acceptors
- 5
- Formal charge
- 0
via PubChem
Research
888 papers- Astemizole: a long-acting, nonsedating antihistamine.Drug intelligence & clinical pharmacy · 1987
- Astemizole. A review of its pharmacodynamic properties and therapeutic efficacy.Drugs · 1984
- Astemizole: an old anti-histamine as a new promising anti-cancer drug.Anti-cancer agents in medicinal chemistry · 2011
- Astemizole as a drug to inhibit the effect of SARS-COV-2 in vitro.Microbial pathogenesis · 2021
- [Astemizole: its pharmacokinetics and pharmacologic properties].Allergie et immunologie · 1990
via PubMed
Wikidata facts
- Subclass of
- heterocyclic compound
- Has part
- nitrogen
- Mass
- 458.248
- Has use
- medication
Show 8 more facts
- significant drug interaction
- thioridazine
- chemical formula
- C₂₈H₃₁FN₄O
- medical condition treated
- urticaria
- canonical SMILES
- COC1=CC=C(C=C1)CCN2CCC(CC2)NC3=NC4=CC=CC=C4N3CC5=CC=C(C=C5)F
- World Health Organisation international non-proprietary name
- astemizole
- defined daily dose
- 10
- physically interacts with
- Potassium voltage-gated channel subfamily H member 2
- Commons category
- Astemizole
via Wikidata · CC0
~2 min read
Encyclopedic overview
4 sectionsContents
- Pharmacology
- Toxicity
- References
- External links
Astemizole (marketed under the brand name Hismanal, developmental code R43512) was a second-generation antihistamine drug that has a long duration of action. Astemizole was discovered by Janssen Pharmaceutica in 1977. It was withdrawn from the market globally in 1999 because of rare but potentially fatal side effects (QTc interval prolongation and related arrhythmias due to hERG channel blockade).
==Pharmacology== Astemizole is a histamine H1-receptor antagonist. It has anticholinergic and antipruritic effects.
Excerpted from Wikipedia’s “astemizole” article, available under the CC BY-SA 4.0 licence.