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A2861

Sigma-Aldrich

Astemizole

≥98% (HPLC)

Synonym(s):

1-(4-Fluorobenzyl)-2-(1-[4-methoxyphenethyl]piperidin-4-yl)aminobenzimidazole

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About This Item

Empirical Formula (Hill Notation):
C28H31FN4O
CAS Number:
68844-77-9
Molecular Weight:
458.57
EC Number:
272-441-9
MDL number:
MFCD00153919
UNSPSC Code:
41121800
PubChem Substance ID:
329770802
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

storage condition

desiccated
protect from light

solubility

DMSO: >20 mg/mL

originator

Johnson & Johnson

storage temp.

2-8°C

SMILES string

COc1ccc(CCN2CCC(CC2)Nc3nc4ccccc4n3Cc5ccc(F)cc5)cc1

InChI

1S/C28H31FN4O/c1-34-25-12-8-21(9-13-25)14-17-32-18-15-24(16-19-32)30-28-31-26-4-2-3-5-27(26)33(28)20-22-6-10-23(29)11-7-22/h2-13,24H,14-20H2,1H3,(H,30,31)

InChI key

GXDALQBWZGODGZ-UHFFFAOYSA-N

Gene Information

human ... HRH1(3269)

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Biochem/physiol Actions

Astermizole is a potent hERG potassium channel blocker (IC50 of 0.9 nM) and may used as a pharmacological chaperone to correct folding defects and restore protein function for some mutated forms of hERG channels. It has also been studied for treatment of malaria, hERG and hEAG channel function in cancer and as a second generation antihistamine H-1 antagonist.

Features and Benefits

This compound is featured on the Potassium Channels page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
This compound was developed by Johnson & Johnson. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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M F Nilsson et al.
Reproductive toxicology (Elmsford, N.Y.), 29(2), 156-163 (2010-02-11)
Drugs blocking the potassium current IKr of the heart (via hERG channel-inhibition) have the potential to cause hypoxia-related teratogenic effects. However, this activity may be missed in conventional teratology studies because repeat dosing may cause resorptions. The aim of the
Andrew M Sawayama et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 15(43), 11723-11729 (2009-09-24)
Herein we demonstrate that a small panel of variants of cytochrome P450 BM3 from Bacillus megaterium covers the breadth of reactivity of human P450s by producing 12 of 13 mammalian metabolites for two marketed drugs, verapamil and astemizole, and one
Astemizole. A nonsedating antihistamine with fast and sustained activity.
M M Janssens
Clinical reviews in allergy, 11(1), 35-63 (1993-01-01)
Tjøstil Vlaar et al.
Angewandte Chemie (International ed. in English), 51(52), 13058-13061 (2012-11-20)
O(2) in, H(2)O out: Various diamines and related bisnucleophiles readily undergo oxidative isocyanide insertion with Pd(OAc)(2) (1 mol %) as the catalyst and O(2) as the terminal oxidant to give a diverse array of medicinally relevant N heterocycles. The utility
Chitalu C Musonda et al.
Bioorganic & medicinal chemistry letters, 19(2), 481-484 (2008-12-05)
A dual activity, conjugated approach has been taken to form hybrid molecules of two known antimalarial drugs, chloroquine (CQ) and the non-sedating H1 antagonist astemizole. A variety of linkers were investigated to conjugate the two agents into one molecule. Compounds
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