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Astemizole

Uses
Astemizole
Astemizole structure
CAS No.
68844-77-9
Chemical Name:
Astemizole
Synonyms
r45312;MJD-30;r42512;retolen;Waruzol;R 43512;Metodik;idazole;laridal;metodih
CBNumber:
CB6741448
Molecular Formula:
C28H31FN4O
Formula Weight:
458.57
MOL File:
68844-77-9.mol

Astemizole Properties

Melting point:
172.9°C
Boiling point:
627.3±65.0 °C(Predicted)
Density 
1.1587 (estimate)
storage temp. 
2-8°C
solubility 
DMSO: >20mg/mL
pka
pKa 4.85(H2O t=25.0 I=0.025) (Uncertain);8.69(H2O t=25.0 I=0.025) (Uncertain)
form 
powder
color 
Crystals
Water Solubility 
It is soluble in DMSO (25 mg/ml ), ethanol (25 mg/ml), chloroform, methanol, and water (partly miscible).
FDA UNII
7HU6337315
ATC code
R06AX11
SAFETY
  • Risk and Safety Statements
Symbol(GHS) 
GHS07
Signal word  Warning
Hazard statements  H315-H319-H335
Precautionary statements  P305+P351+P338-P261-P280a-P304+P340-P405-P501a
Hazard Codes  Xn
Risk Statements  22-36/37/38
Safety Statements  26-36
RIDADR  UN 2811 6.1 / PGII
WGK Germany  3
RTECS  DD8968000
HS Code  2933992600
Toxicity LD50 orl-rat: >2560 mg/kg AIPTAK 251,39,81

Astemizole price More Price(7)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich A2861 Astemizole ≥98% (HPLC) 68844-77-9 10mg $88.2 2021-03-22 Buy
Sigma-Aldrich 1044301 Astemizole United States Pharmacopeia (USP) Reference Standard 68844-77-9 200mg $350 2021-03-22 Buy
Alfa Aesar J60339 Astemizole, 99+% 68844-77-9 50mg $154 2021-03-22 Buy
Cayman Chemical 16967 Astemizole ≥98% 68844-77-9 25mg $39 2021-03-22 Buy
Cayman Chemical 16967 Astemizole ≥98% 68844-77-9 50mg $74 2021-03-22 Buy

Astemizole Chemical Properties,Uses,Production

Uses

Astemizole is a histamine H1-receptor antagonist with IC50 of 4.7 nM. Astemizole is also a potent inhibitor of ether à-go-go 1 (Eag1) and Eag-related gene (Erg) potassium channels. Astemizole has antineoplastic and antipruritic effects.

Description

Astemizole belongs to the second-generation class of non-sedating, non-anticholinergic antihistamines. Its non-sedating properties appear to result from its poor penetration of the blood brain barrier. As a result it shows no potentiation of CNS depressants, including alcohol. Its long half-life allows once-daily dosing.

Chemical Properties

Crystalline Solid

Originator

Janssen (Belgium)

Uses

Nonsedating-type histamine H1-receptor antagonist. Potential for combination therapy with antivancer drugs such as doxorubicin in resistant leukemia. Antihistaminic

Uses

scabicide

Uses

Astemizole is used for preventing and treating severe seasonal and chronic allergic rhinitis, allergic conjunctivitis, hives, Quinke’s edema, other allergic conditions and dermatitis. Synonyms of this drug are hismanal, histazol, and others.

Definition

ChEBI: A piperidine compound having a 2-(4-methoxyphenyl)ethyl group at the 1-position and an N-[(4-fluorobenzyl)benzimidazol-2-yl]amino group at the 4-position.

Manufacturing Process

A mixture of 2.3 parts of 2-(4-methoxyphenyl)ethyl methanesulfonate, 4.9 parts of 1-[(4-fluorophenyl)methyl]-N-(4-piperidinyl)-1H-benzimidazol-2- amine dihydrobromide, 3.2 parts of sodium carbonate, 0.1 part of potassium iodide and 90 parts of N,N-dimethylformamide is stirred overnight at 70°C. The reaction mixture is poured onto water. The product is extracted with methylbenzene. The extract is washed with water, dried, filtered and evaporated. The residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (98:2 by volume) as eluent. The pure fractions are collected and the eluent is evaporated. The residue is crystallized from 2,2'-oxybispropane, yielding 2.2 parts (48%) of 1- (4-fluorophenylmethyl)-N-[1-[2-(4-methoxyphenyl)ethyl]-4-piperidinyl]-1Hbenzimidazol- 2-amine, MP 149.1°C.

brand name

Hismanal (Janssen);Alermizol;Astezol;Astol;Histamanal;Novo-nastizol;EISMANAL.

Therapeutic Function

Antiallergic, Antihistaminic

World Health Organization (WHO)

The first clinically interesting histamine ti-antagonists were introduced in the late forties and early fifties. Several histamine ti-antagonists have a similar cardiac effect to that seen with astemizole and terfenadine. Serious cardiovascular adverse reactions have been reported when used concomitantly with imidazole antifungals and macrolide antibiotics.

Biological Activity

Orally active, potent histamine H 1 antagonist (IC 50 = 4 nM) that displays 20-fold, > 250-fold and > 250-fold selectivity over 5-HT, dopamine and muscarinic acetylcholine receptors respectively. Exhibits antimalarial activity in multidrug resistant strains in vitro (IC 50 = 227 - 734 nM). Also potent hERG K + channel blocker (IC 50 = 0.9 nM) that displays cardiotoxicity in vivo .

Safety Profile

Poison by subcutaneous andintravenous routes. Moderately toxic by ingestion. Humansystemic effects by ingestion: arrhythmias, coma, nauseaor vomiting, somnolence. When heated to decompositionit emits toxic fumes of F?? and NOx.

Chemical Synthesis

Astemizole, 1-[(4-fluorophenyl)methyl]-N-[1-[2-(4-methoxyphenyl) ethyl]-4- piperidinyl]-benzimidazol-2-amine (16.1.31), is synthesized in a multi-stage synthesis from 1-carbethoxy-4-aminopiperidine and 2-nitroisothiocyanobenzol, from which a derivative of thiourea (16.1.26) is synthesized upon their reaction. The nitro group of the product is reduced and the further S-methoxided. In reaction conditions intermolecular cyclization into a derivative of benimidazol, N-[1-[2-(4-carethoxy)]-4-piperidinyl]benzimidazol-2-amine (16.1.28) occurs. The obtained aminobenzimidazole derivative is alkylated with 4-fluorobenzylchoride into 1-[(flurophenyl)methyl]-N-[1-[2-(4-carethoxy)]-4-piperidinyl] benzimidazol- 2-amine (16.1.29). The carbethoxyl group of the resulting compound (16.1.29) is hydrolyzed by hydrobromic acid, forming a non-substituted on the nitrogen atom derivative of piperidine (16.1.30), the alkylation of which with 2-(4-methoxyphenyl)ethylmetanesulfonate leads to the formation of astemizole (16.1.31).

Astemizole Preparation Products And Raw materials

Raw materials

Preparation Products


Astemizole Suppliers

Global( 121)Suppliers
Supplier Tel Fax Email Country ProdList Advantage
ATK CHEMICAL COMPANY LIMITED
+86 21 5161 9050/ 5187 7795
+86 21 5161 9052/ 5187 7796 ivan@atkchemical.com CHINA 26751 60
CONIER CHEM AND PHARMA LIMITED
86-18523575427
sales@conier.com CHINA 47498 58
Shaanxi Dideu Medichem Co. Ltd
13772537765
029-88380327 1010@dideu.com CHINA 3993 58
Target Molecule Corp
18019718960 781-999-5354
marketing@targetmol.com United States 19232 58
Shaanxi Dideu Medichem Co. Ltd
18192503167 +86-29-89586680
+86-29-88380327 1005@dideu.com CHINA 9938 58
Dideu Industries Group Limited
029-88380327
Service@dideu.com CHINA 30013 58
AFINE CHEMICALS LIMITED
008657185134551
008657185134895 info@afinechem.com CHINA 15559 58
Shanghai kingmorn biotechnology Co.,Ltd.
15000569291 021-62200788
2199306478@qq.com CHINA 100 58
J & K SCIENTIFIC LTD. 400-666-7788 010-82848833-
86-10-82849933 jkinfo@jkchemical.com;market6@jkchemical.com China 96815 76
3B Pharmachem (Wuhan) International Co.,Ltd. 18930552037 821-50328103-801
86-21-50328109 3bsc@sina.com China 15877 69

View Lastest Price from Astemizole manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2021-07-20 Astemizole
68844-77-9
US $1.00-1.00 / KG 1g 99% 50tons Shaanxi Dideu Medichem Co. Ltd
2021-07-16 Astemizole
68844-77-9
US $0.00-0.00 / KG 1g 98% >10kg Shanghai kingmorn biotechnology Co.,LTD.
2021-06-17 Astemizole USP/EP/BP
68844-77-9
US $1.10 / g 1g 99.9% 100 Tons Min Dideu Industries Group Limited

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