AstemizoleA potent and selective H1-receptor antagonist that displays antihistamine and antimalarial activity

Astemizole (CAS 68844-77-9)

Astemizole | CAS 68844-77-9 is rated 5.0 out of 5 by 1.
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Synonym: Hismanal;1-[(4-Fluorophenyl)methyl]-N-[1-[2-(4-methoxyphenyl)ethyl]-4-piperidinyl]-1H-benzimidazol-2-amine
Application: A potent and selective H1-receptor antagonist that displays antihistamine and antimalarial activity
CAS Number: 68844-77-9
Purity: ≥97%
Molecular Weight: 458.58
Molecular Formula: C28H31FN4O
* Refer to Certificate of Analysis for lot specific data (including water content).
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Astemizole is a potent antihistamine (H1-receptor antagonist; IC50 = 4 nM) that displays selectivity over dopamine, 5-HT, and muscarinic acetylcholine receptors. This compound has shown potent hERG K+ channel blocking activity (IC50 = 0.9 nM), antimalarial activity in multidrug resistant strains in vitro (IC50 = 227 - 734 nM), and has been used as a chaperone to correct folding defects and restore protein function for some mutated forms of hERG channels.


References

1. Laduron, P.M., et al. 1982. Mol. Pharmacol. 21: 294-300. PMID: 6124876
2. Richards, D.M., et al. 1984. Drugs. 28: 38-61. PMID: 6204835
3. Ishikawa, M., et al. 2000. Biol. Pharm. Bull. 23: 112-115. PMID: 10706423
4. Ficker, E., et al. 2002. J. Biol. Chem. 277: 4989-4998. PMID: 11741928
5. Chong, C.R., et al. 2006. Nat. Chem. Biol. 2: 415-416. PMID: 16816845
6. Roy, J., et al. 2008. Oncol. Rep. 19: 1511-1516. PMID: 18497958
7. Wang, L., et al. 2009. Mol. Pharmacol. 75: 927-937. PMID: 19139152

Appearance :
Crystalline
Physical State :
Solid
Solubility :
Soluble in DMSO (25 mg/ml ), ethanol (25 mg/ml), chloroform, methanol, and water (partly miscible).
Storage :
Store at room temperature
Melting Point :
267.15° C (Predicted)
Boiling Point :
~627.3° C at 760 mmHg (Predicted)
Density :
~1.2 g/cm3 (Predicted)
Refractive Index :
n20D 1.62 (Predicted)
IC50 :
Histamine H1: IC50 = 4 nM; hERG K+ channel: IC50 = 0.9 nM; P-glycoprotein 1: IC50 = 300 nM (human); Dopamine D1 receptor: IC50 = 4.01 µM (human); Serotonin 2a receptor: IC50 = 20 nM (human)
Ki Data :
HERG: Ki= 2.9 nM (human); Alpha-1d adrenergic recepto: Ki= 9.9 nM (rat); Serotonin 2a receptor: Ki= 5.58 nM (human); Melanocortin receptor 4: Ki= 13.5 µM (human); Histamine H1 receptor: Ki= 1.61 nM (human); Dopamine D3 receptor: Ki= 148 nM (human)
pK Values :
pKb: 8.68 (Predicted)
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
WGK Germany :
3
RTECS :
DD8968000
PubChem CID :
2247
Merck Index :
14: 856
MDL Number :
MFCD00153919
EC Number :
272-441-9
SMILES :
COC1=CC=C(C=C1)CCN2CCC(CC2)NC3=NC4=CC=CC=C4N3CC5=CC=C(C=C5)F

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Certificate of Analysis

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Rated 5 out of 5 by from Roy et al Roy et al. (PubMed ID 18497958) found that Astemizole, a human ether-a-go-go (hEAG) potassium channel inhibitor, blocked MCF-7 cell proliferation. -SCBT Publication Review
Date published: 2015-05-04
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