Astemizole
Uses- Product Name
- Astemizole
- 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 Property
- 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).
- Stability:
- Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 3 months.
Safety
- 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
- Hazardous Substances Data
- 68844-77-9(Hazardous Substances Data)
- Toxicity
- LD50 orl-rat: >2560 mg/kg AIPTAK 251,39,81
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P264Wash hands thoroughly after handling.
P264Wash skin thouroughly after handling.
P271Use only outdoors or in a well-ventilated area.
P280Wear protective gloves/protective clothing/eye protection/face protection.
P302+P352IF ON SKIN: wash with plenty of soap and water.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- A2861
- Product name
- Astemizole
- Purity
- ≥98% (HPLC)
- Packaging
- 10mg
- Price
- $106
- Updated
- 2024/03/01
- Product number
- J60339
- Product name
- Astemizole, 99+%
- Packaging
- 50mg
- Price
- $171.65
- Updated
- 2024/03/01
- Product number
- 16967
- Product name
- Astemizole
- Purity
- ≥98%
- Packaging
- 25mg
- Price
- $49
- Updated
- 2024/03/01
- Product number
- 16967
- Product name
- Astemizole
- Purity
- ≥98%
- Packaging
- 50mg
- Price
- $92
- Updated
- 2024/03/01
- Product number
- A2861
- Product name
- Astemizole
- Purity
- ≥98% (HPLC)
- Packaging
- 50mg
- Price
- $251.4
- Updated
- 2024/03/01
Astemizole Chemical Properties,Usage,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 .
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.
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.
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).
storage
Store at +4°C
References
1) Richards et al. (1984), Astemizole. A review of its pharmacodynamic properties and therapeutic efficacy; Drugs, 28 38 2) Laduron et al. (1982), In vitro and in vivo binding characteristics of a new long-acting histamine H1 antagonist, astemizole; Mol. Pharmacol., 21 294
Astemizole Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from Astemizole manufacturers
- Product
- Astemizole 68844-77-9
- Price
- US $1.00-1.00/KG
- Min. Order
- 1g
- Purity
- 99%
- Supply Ability
- 50tons
- Release date
- 2020-05-08
- Product
- Astemizole 68844-77-9
- Price
- US $0.00-0.00/KG
- Min. Order
- 1g
- Purity
- 98%
- Supply Ability
- >10kg
- Release date
- 2021-07-14
- Product
- Astemizole 68844-77-9
- Price
- US $1.10/g
- Min. Order
- 1g
- Purity
- 99.9%
- Supply Ability
- 100 Tons Min
- Release date
- 2021-06-16