Substance
ID:520
Names and Identifiers
Brand Name
HistamenHistazolMetodikRetolenAlermizolAstemisonAstemisanHistaminosLaridalParalerginAstemisolHismanalKelpNono-Nastizol AWaruzol
Synonyms
Astemizole
IUPAC Traditional name
astemizole
IUPAC name
1-[(4-fluorophenyl)methyl]-N-{1-[2-(4-methoxyphenyl)ethyl]piperidin-4-yl}-1H-1,3-benzodiazol-2-amine
Properties
Physical Property
Hydrophobicity(logP)
5.8
Solubility
432 mg/L
Molecule Details
Drug Groups
approved; withdrawn
Description
Astemizole is a long-acting, non-sedating second generation antihistamine used in the treatment of allergy symptoms. It was withdrawn from market by the manufacturer in 1999 due to the potential to cause arrhythmias at high doses, especially when when taken with CYP inhibitors or grapefruit juice.
Indication
Astemizole was indicated for use in the relieving allergy symptoms, particularly rhinitis and conjunctivitis. It has been withdrawn from the market however due to concerns of arrhythmias.
Pharmacology
Astemizole is a second generation H1-receptor antagonist. It does not significantly cross the blood brain barrier and therefore does not cause drowsiness or CNS depression at normal doses.
Toxicity
LD50=2052mg/kg in mice
Affected Organisms
Humans and other mammals
Biotransformation
Almost completely metabolized in the liver and primarily excreted in the feces.
Absorption
Rapidly absorbed from the gastrointestinal tract.
Half Life
1 day
Protein Binding
96.7%
References
•
Wang X, Hockerman GH, Green HW 3rd, Babbs CF, Mohammad SI, Gerrard D, Latour MA, London B, Hannon KM, Pond AL: Merg1a K+ channel induces skeletal muscle atrophy by activating the ubiquitin proteasome pathway. FASEB J. 2006 Jul;20(9):1531-3. Epub 2006 May 24.
[Pubmed]
•
Chong CR, Chen X, Shi L, Liu JO, Sullivan DJ Jr: A clinical drug library screen identifies astemizole as an antimalarial agent. Nat Chem Biol. 2006 Aug;2(8):415-6. Epub 2006 Jul 2.
[Pubmed]
External Links
Molecular Spectra
No Data Available
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References
• Wang X, Hockerman GH, Green HW 3rd, Babbs CF, Mohammad SI, Gerrard D, Latour MA, London B, Hannon KM, Pond AL: Merg1a K+ channel induces skeletal muscle atrophy by activating the ubiquitin proteasome pathway. FASEB J. 2006 Jul;20(9):1531-3. Epub 2006 May 24. Pubmed
• Chong CR, Chen X, Shi L, Liu JO, Sullivan DJ Jr: A clinical drug library screen identifies astemizole as an antimalarial agent. Nat Chem Biol. 2006 Aug;2(8):415-6. Epub 2006 Jul 2. Pubmed