CAS 68844-77-9|Histazol|Retolen|astemizole|Astemison|Hismanal|Nono-Nastizol A|Metodik|Kelp|Astemizole|Laridal|Paralergin|Histamen|Astemisan|Histaminos|1-[(4-fluorophenyl)methyl]-N-{1-[2-(4-methoxyph...

基本信息

化学结构

分子式

C₂₈H₃₁FN₄O

分子量

458.5703432

精确质量

458.24818985

电荷

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)

InChIKey

GXDALQBWZGODGZ-UHFFFAOYSA-N

Canonic Smiles

COc1ccc(cc1)CCN1CCC(CC1)Nc1nc2c(n1Cc1ccc(cc1)F)cccc2

Isomeric Smiles

Fc1ccc(Cn2c(NC3CCN(CC3)CCc3ccc(OC)cc3)nc3c2cccc3)cc1

计算属性

JChem

质子受体

质子供体

LogD (pH = 5.5)

1.4488908

LogD (pH = 7.4)

3.9728467

Log P

5.3896523

摩尔折射率

135.6432

极化性

52.523415

极化表面积

42.32

可自由旋转的化学键

里宾斯基五规则

false

ALOGPS 2.1

Log P

5.92

LOG S

-5.58

溶解度

1.20e-03 g/l

数据来源

名称和标识

商标名

RetolenAstemisonHistamenHistaminosKelpLaridalHismanalNono-Nastizol AHistazolAlermizolAstemisolMetodikAstemisanParalerginWaruzol

IUPAC传统名

astemizole

IUPAC标准名

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

别名

Astemizole1-(4-Fluorobenzyl)-2-(1-[4-methoxyphenethyl]piperidin-4-yl)aminobenzimidazoleAstemizole1-(4-fluorobenzyl)-2-(1-(4-methoxyphenethyl)piperidin-4-yl)aminobenzimidazoleRetolenHistamenWaruzolAstemisanR 42512ParalerginR 43512Hismanal1-[(4-Fluorophenyl)methyl]-N-[1-[2-(4-methoxyphenyl)ethyl]-4-piperidinyl]-1H-benzimidazol-2-amine

名称和标识

数据登录号

PubChem SID

PubChem CID

CAS号

EC号

MDL号

数据登录号

化合物性质

产品相关信息

Empirical Formula (Hill Notation)

C28H31FN4O

纯度

≥98% (HPLC)

98%

质检报告

下载链接

化合物性质

分子相关蛋白质

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分子图谱

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描述信息

DrugBank

DB00637

Drug Groups

approved; withdrawn

Description

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 It was withdrawn from market by the manufacturer in 1999 due to the potential to cause arrhythmias at high doses, especially when when taken with CYP inhibitors or grapefruit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

Indication

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 It has been withdrawn from the market however due to concerns of arrhythmias.

Pharmacology

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.

Toxicity

LD₅₀=2052mg/kg in mice

Affected Organisms

Humans and other mammals

Biotransformation

Almost completely metabolized in the liver and primarily excreted in the feces.

Absorption

Rapidly absorbed from the gastrointestinal tract.

Half Life

1 day

Protein Binding

96.7%

References

• Wang X, Hockerman GH, Green HW 3rd, Babbs CF, Mohammad SI, Gerrard D, Latour MA, London B, Hannon KM, Pond AL: Merg1a K+ channel induces skeletal muscle atrophy by activating the ubiquitin proteasome pathway. FASEB J. 2006 Jul;20(9):1531-3. Epub 2006 May 24. [Pubmed]

• Chong CR, Chen X, Shi L, Liu JO, Sullivan DJ Jr: A clinical drug library screen identifies astemizole as an antimalarial agent. Nat Chem Biol. 2006 Aug;2(8):415-6. Epub 2006 Jul 2. [Pubmed]

External Links

• [Wikipedia]

• [RxList]

• [Drugs.com]

Sigma Aldrich

A2861

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.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. A2861.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

TRC

A790030

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

描述信息

参考文献

PubChem文献

数据源提供

• Chong CR, Chen X, Shi L, Liu JO, Sullivan DJ Jr: A clinical drug library screen identifies astemizole as an antimalarial agent. Nat Chem Biol. 2006 Aug;2(8):415-6. Epub 2006 Jul 2. Pubmed

• Laduron, P.M., et al.: Mol. Pharmacol., 21, 294 (1981)

• Wauquier, A., et al.: Eur. J. Pharmacol., 72, 245 (1981)

• Ishikawa, M., et al.: Biol.

• Richards, D.M., et al.: Drugs, 28, 38 (1981)

• Al-Obaid, A.M., et al.: Anal. Profiles Drug Subs., 20, 173 (1981)

参考文献

生物活性

PubChem BioAssay

生物活性

名称和标识

商标名

RetolenAstemisonHistamenHistaminosKelpLaridalHismanalNono-Nastizol AHistazolAlermizolAstemisolMetodikAstemisanParalerginWaruzol

IUPAC传统名

astemizole

IUPAC标准名

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

别名

数据登录号

PubChem SID

PubChem CID

CAS号

EC号

MDL号

描述信息

DB00637

Drug Groups

approved; withdrawn

Description

Indication

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.

Pharmacology

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.

Toxicity

LD₅₀=2052mg/kg in mice

Affected Organisms

Humans and other mammals

Biotransformation

Almost completely metabolized in the liver and primarily excreted in the feces.

Absorption

Rapidly absorbed from the gastrointestinal tract.

Half Life

1 day

Protein Binding

96.7%

References

• Chong CR, Chen X, Shi L, Liu JO, Sullivan DJ Jr: A clinical drug library screen identifies astemizole as an antimalarial agent. Nat Chem Biol. 2006 Aug;2(8):415-6. Epub 2006 Jul 2. [Pubmed]

External Links

• [Wikipedia]

• [RxList]

• [Drugs.com]

Sigma Aldrich

A2861

TRC

A790030

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

参考文献

PubChem文献

数据源提供

• Chong CR, Chen X, Shi L, Liu JO, Sullivan DJ Jr: A clinical drug library screen identifies astemizole as an antimalarial agent. Nat Chem Biol. 2006 Aug;2(8):415-6. Epub 2006 Jul 2. Pubmed

• Laduron, P.M., et al.: Mol. Pharmacol., 21, 294 (1981)

• Wauquier, A., et al.: Eur. J. Pharmacol., 72, 245 (1981)

• Ishikawa, M., et al.: Biol.

• Richards, D.M., et al.: Drugs, 28, 38 (1981)

• Al-Obaid, A.M., et al.: Anal. Profiles Drug Subs., 20, 173 (1981)

生物活性

PubChem BioAssay

化合物性质

产品相关信息

Empirical Formula (Hill Notation)

C28H31FN4O

纯度

≥98% (HPLC)

98%

质检报告

下载链接

化合物信息

ID:519