Astemizole

Các tên gọi khác (7 ) :

1-(P-Fluorobenzyl)-2-((1-(2-(P-methoxyphenyl)ethyl)piperid-4-yl)amino)benzimidazole
1-(P-Fluorobenzyl)-2-((1-(P-methoxyphenethyl)-4-piperidyl)amino)benzimidazole
Astemison
Astemizol
Astemizol
Astémizole
Astemizolum

Thuốc chống dị ứng & dùng trong các trường hợp quá mẫn

Thuốc Gốc

Small Molecule

CAS: 68844-77-9

ATC: R06AX11

CTHH: C₂₈H₃₁FN₄O

PTK: 458.5703

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 It was withdrawn from market by the manufacturer in 1999 due to the potential to cause arrhythmias at high doses, especially when when taken with CYP inhibitors or grapefruit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.

Nhận Dạng Quốc Tế & Đặc Tính Hóa Học

Công thức hóa học

C₂₈H₃₁FN₄O

Phân tử khối

458.5703

Monoisotopic mass

458.248189839

InChI

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

InChIKey=GXDALQBWZGODGZ-UHFFFAOYSA-N

IUPAC Name

1-[(4-fluorophenyl)methyl]-N-{1-[2-(4-methoxyphenyl)ethyl]piperidin-4-yl}-1H-1,3-benzodiazol-2-amine

Traditional IUPAC Name

astemizole

SMILES

COC1=CC=C(CCN2CCC(CC2)NC2=NC3=CC=CC=C3N2CC2=CC=C(F)C=C2)C=C1

Độ tan chảy

149.1 °C

Độ hòa tan

432 mg/L

logP

5.8

logS

-5.6

pKa (Strongest Basic)

8.75

PSA

42.32 Å²

Refractivity

135.64 m³·mol^-1

Polarizability

52.08 Å³

Rotatable Bond Count

H Bond Acceptor Count

H Bond Donor Count

Physiological Charge

Number of Rings

Bioavailability

MDDR-Like Rule

true

Dược Lực Học : 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.

Cơ Chế Tác Dụng : 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 It was withdrawn from market by the manufacturer in 1999 due to the potential to cause arrhythmias at high doses, especially when when taken with CYP inhibitors or grapefruit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. Astemizole competes with histamine for binding at H₁-receptor sites in the GI tract, uterus, large blood vessels, and bronchial muscle. This reversible binding of astemizole to H₁-receptors suppresses the formation of edema, flare, and pruritus resulting from histaminic activity. As the drug does not readily cross the blood-brain barrier and preferentially binds at H1 receptors in the peripehery rather than within the brain, CNS depression is minimal. Astemizole may also act on H₃-receptors, producing adverse effects.

Dược Động Học :

▧ Absorption :
Rapidly absorbed from the gastrointestinal tract.
▧ Protein binding :
96.7%
▧ Metabolism :
Almost completely metabolized in the liver and primarily excreted in the feces.
▧ Half Life :
1 day

Độc Tính : LD₅₀=2052mg/kg in mice

Chỉ Định : 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.

Tương Tác Thuốc :

Amprenavir Increased risk of cardiotoxicity and arrhythmias
Aprepitant Increased risk of cardiotoxicity and arrhythmias
Bepridil Increased risk of cardiotoxicity and arrhythmias
Cimetidine Increased risk of cardiotoxicity and arrhythmias
Cisapride Increased risk of cardiotoxicity and arrhythmias
Clarithromycin Increased risk of cardiotoxicity and arrhythmias
Delavirdine Increased risk of cardiotoxicity and arrhythmias
Efavirenz Increased risk of cardiotoxicity and arrhythmias
Erythromycin Increased risk of cardiotoxicity and arrhythmias
Fluoxetine Increased risk of cardiotoxicity and arrhythmias
Fluvoxamine Increased risk of cardiotoxicity and arrhythmias
Fosamprenavir Increased risk of cardiotoxicity and arrhythmias
Grepafloxacin Increased risk of cardiotoxicity and arrhythmias
Indinavir Increased risk of cardiotoxicity and arrhythmias
Itraconazole Increased risk of cardiotoxicity and arrhythmias
Josamycin Increased risk of cardiotoxicity and arrhythmias
Ketoconazole Increased risk of cardiotoxicity and arrhythmias
Mesoridazine Increased risk of cardiotoxicity and arrhythmias
Mibefradil Increased risk of cardiotoxicity and arrhythmias
Nefazodone Increased risk of cardiotoxicity and arrhythmias
Nelfinavir Increased risk of cardiotoxicity and arrhythmias
Posaconazole Contraindicated co-administration
Quinine Increased risk of cardiotoxicity and arrhythmias
Quinupristin This combination presents an increased risk of toxicity
Ritonavir Increased risk of cardiotoxicity and arrhythmias
Saquinavir Increased risk of cardiotoxicity and arrhythmias
Sparfloxacin Increased risk of cardiotoxicity and arrhythmias
Telavancin Additive QTc-prolongation may occur. Concomitant therapy should be avoided.
Telithromycin Increased risk of cardiotoxicity and arrhythmias
Thioridazine Increased risk of cardiotoxicity and arrhythmias
Tipranavir Tipranavir, co-administered with Ritonavir, may increase the plasma concentration of Astemizole. Concomitant therapy is contraindicated.
Troleandomycin Increased risk of cardiotoxicity and arrhythmias
Voriconazole Increased risk of cardiotoxicity and arrhythmias

Liều Lượng & Cách Dùng : Tablet - Oral

Dữ Kiện Thương Mại

Nhà Sản Xuất

Công ty : Lupin

Sản phẩm biệt dược : Acemiz
Công ty : Incobra

Sản phẩm biệt dược : Alerkin
Công ty : Senosiain

Sản phẩm biệt dược : Astesen
Công ty : Janssen

Sản phẩm biệt dược : Hismanal
Công ty : Biofarma

Sản phẩm biệt dược : Histalong
Công ty : Bruluart

Sản phẩm biệt dược : Lergibrumizol
Công ty : Cadila HC

Sản phẩm biệt dược : Stemiz

Tài Liệu Tham Khảo Thêm

drugbank

http://www.drugbank.ca/drugs/DB00637

PubChem Compound

http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=2247

PubChem Substance

http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46508569

KEGG Compound

http://www.genome.jp/dbget-bin/www_bget?cpd:C06832

KEGG Drug

http://www.genome.jp/dbget-bin/www_bget?drug:D00234

ChemSpider

http://www.chemspider.com/Chemical-Structure.2160.html

BindingDB

http://www.bindingdb.org/bind/chemsearch/marvin/MolStructure.jsp?monomerid=24226

PharmGKB

http://www.pharmgkb.org/drug/PA448498

Wikipedia

http://en.wikipedia.org/wiki/Astemizole

RxList

http://www.rxlist.com/cgi/generic/astem.htm

Drugs.com

http://www.drugs.com/mtm/astemizole.html

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