Astemizole - DrugBank

ID Pharmacology Interactions References Trials Economics Properties Spectra Taxonomy

Targets (4)Enzymes (5)Transporters (1)

Targets (4)Enzymes (5)Transporters (1)Biointeractions (9)

Identification

Name

Astemizole

Accession Number

DB00637 (APRD00585)

Type

Small Molecule

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Approved, Withdrawn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 It was withdrawn from market by the manufacturer in 1999 due to the potential to cause arrhythmias at high doses, especially when when taken with CYP inhibitors or grapefruit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

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

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

Astémizole

Astemizolum

External IDs

BRN 4830190 / R 43,512 / R43512 / UNII-7HU6337315

Product Ingredients

Not Available

Approved Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Hismanal - Tab 10mg	Tablet	10 mg	Oral	Johnson & Johnson Merck Consumer Pharmaceuticals Of Canada	1997-01-21	1999-03-04	Canada
Hismanal Suspension 2mg/ml	Suspension	2 mg	Oral	Janssen Pharmaceutica, Division Of Janssen Ortho Inc.	1984-12-31	1997-08-12	Canada
Hismanal Tab 10mg	Tablet	10 mg	Oral	Janssen Pharmaceutica, Division Of Janssen Ortho Inc.	1984-12-31	1997-08-12	Canada

Approved Generic Prescription Products

Not Available

Approved Over the Counter Products

Not Available

Unapproved/Other Products

Not Available

International Brands

Name	Company
Acemiz	Lupin
Alerkin	Incobra
Astesen	Senosiain
Hismanal	Janssen
Histalong	Biofarma
Lergibrumizol	Bruluart
Stemiz	Cadila HC

Brand mixtures

Not Available

Categories

UNII

7HU6337315

CAS number

68844-77-9

Weight

Average: 458.5703
Monoisotopic: 458.248189839

Chemical Formula

C₂₈H₃₁FN₄O

InChI Key

GXDALQBWZGODGZ-UHFFFAOYSA-N

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)

IUPAC Name

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

SMILES

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

Pharmacology

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.

Structured Indications

Not Available

Pharmacodynamics

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.

Mechanism of action

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.

Target	Kind	Pharmacological action	Actions	Organism	UniProt ID
Histamine H1 receptor	Protein	yes	antagonist	Human	P35367	details
Potassium voltage-gated channel subfamily H member 2	Protein	unknown	inhibitor	Human	Q12809	details
Potassium voltage-gated channel subfamily H member 1	Protein	unknown	Not Available	Human	O95259	details
Microtubule-associated protein tau	Protein	unknown	Not Available	Human	P10636	details

Absorption

Rapidly absorbed from the gastrointestinal tract.

Volume of distribution

Not Available

Protein binding

96.7%

Metabolism

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

Substrate	Enzymes	Product
Astemizole	Cytochrome P450 3A4	desmethylastemizole	Details

Route of elimination

Not Available

Half life

1 day

Clearance

Not Available

Toxicity

LD₅₀=2052mg/kg in mice

Affected organisms

Humans and other mammals

Pathways

Not Available

Pharmacogenomic Effects/ADRs

Not Available

Interactions

Drug Interactions

Drug	Interaction	Drug group
2,5-Dimethoxy-4-ethylamphetamine	2,5-Dimethoxy-4-ethylamphetamine may decrease the sedative activities of Astemizole.	Experimental, Illicit
3,4-Methylenedioxyamphetamine	3,4-Methylenedioxyamphetamine may decrease the sedative activities of Astemizole.	Experimental, Illicit
3,4-Methylenedioxymethamphetamine	3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Astemizole.	Experimental, Illicit
4-Bromo-2,5-dimethoxyamphetamine	4-Bromo-2,5-dimethoxyamphetamine may decrease the sedative activities of Astemizole.	Experimental, Illicit
Abiraterone	The serum concentration of Astemizole can be increased when it is combined with Abiraterone.	Approved
Acebutolol	The serum concentration of Acebutolol can be increased when it is combined with Astemizole.	Approved
Acetaminophen	The serum concentration of Acetaminophen can be increased when it is combined with Astemizole.	Approved
Acetylsalicylic acid	The serum concentration of Acetylsalicylic acid can be increased when it is combined with Astemizole.	Approved, Vet Approved
Afatinib	The serum concentration of Afatinib can be increased when it is combined with Astemizole.	Approved
Aldosterone	The serum concentration of Aldosterone can be increased when it is combined with Astemizole.	Experimental
Alitretinoin	The serum concentration of Alitretinoin can be increased when it is combined with Astemizole.	Approved, Investigational
Ambrisentan	The serum concentration of Ambrisentan can be increased when it is combined with Astemizole.	Approved, Investigational
Amiodarone	The serum concentration of Astemizole can be increased when it is combined with Amiodarone.	Approved, Investigational
Amitriptyline	The serum concentration of Amitriptyline can be increased when it is combined with Astemizole.	Approved
Amphetamine	Amphetamine may decrease the sedative activities of Astemizole.	Approved, Illicit
Apixaban	The serum concentration of Apixaban can be increased when it is combined with Astemizole.	Approved
Aprepitant	The serum concentration of Astemizole can be increased when it is combined with Aprepitant.	Approved, Investigational
Arsenic trioxide	The serum concentration of Arsenic trioxide can be increased when it is combined with Astemizole.	Approved, Investigational
Artemether	The metabolism of Astemizole can be decreased when combined with Artemether.	Approved
Atazanavir	The serum concentration of Astemizole can be increased when it is combined with Atazanavir.	Approved, Investigational
Atenolol	The serum concentration of Atenolol can be increased when it is combined with Astemizole.	Approved
Atomoxetine	The metabolism of Astemizole can be decreased when combined with Atomoxetine.	Approved
Axitinib	The serum concentration of Axitinib can be increased when it is combined with Astemizole.	Approved, Investigational
Benzphetamine	Benzphetamine may decrease the sedative activities of Astemizole.	Approved, Illicit
Benzylpenicilloyl Polylysine	Astemizole may decrease effectiveness of Benzylpenicilloyl Polylysine as a diagnostic agent.	Approved
Betahistine	The therapeutic efficacy of Betahistine can be decreased when used in combination with Astemizole.	Approved
Betamethasone	The serum concentration of Betamethasone can be increased when it is combined with Astemizole.	Approved, Vet Approved
Betaxolol	The metabolism of Astemizole can be decreased when combined with Betaxolol.	Approved
Bexarotene	The serum concentration of Astemizole can be decreased when it is combined with Bexarotene.	Approved, Investigational
Bicalutamide	The serum concentration of Astemizole can be increased when it is combined with Bicalutamide.	Approved
Boceprevir	The serum concentration of Astemizole can be increased when it is combined with Boceprevir.	Approved, Investigational
Bortezomib	The metabolism of Astemizole can be decreased when combined with Bortezomib.	Approved, Investigational
Bosentan	The serum concentration of Astemizole can be decreased when it is combined with Bosentan.	Approved, Investigational
Bosutinib	The serum concentration of Bosutinib can be increased when it is combined with Astemizole.	Approved
Brentuximab vedotin	The serum concentration of Brentuximab vedotin can be increased when it is combined with Astemizole.	Approved
Bromocriptine	The serum concentration of Bromocriptine can be increased when it is combined with Astemizole.	Approved, Investigational
Bupropion	The metabolism of Astemizole can be decreased when combined with Bupropion.	Approved
Cabazitaxel	The serum concentration of Cabazitaxel can be increased when it is combined with Astemizole.	Approved
Caffeine	The serum concentration of Caffeine can be increased when it is combined with Astemizole.	Approved
Camptothecin	The serum concentration of Camptothecin can be increased when it is combined with Astemizole.	Experimental
Canagliflozin	The serum concentration of Canagliflozin can be increased when it is combined with Astemizole.	Approved
Carbamazepine	The metabolism of Astemizole can be increased when combined with Carbamazepine.	Approved, Investigational
Carfilzomib	The serum concentration of Carfilzomib can be increased when it is combined with Astemizole.	Approved
Celecoxib	The metabolism of Astemizole can be decreased when combined with Celecoxib.	Approved, Investigational
Ceritinib	The serum concentration of Astemizole can be increased when it is combined with Ceritinib.	Approved
Cerivastatin	The serum concentration of Cerivastatin can be increased when it is combined with Astemizole.	Withdrawn
Chloroquine	The metabolism of Astemizole can be decreased when combined with Chloroquine.	Approved, Vet Approved
Chlorphentermine	Chlorphentermine may decrease the sedative activities of Astemizole.	Illicit, Withdrawn
Chlorpromazine	The serum concentration of Chlorpromazine can be increased when it is combined with Astemizole.	Approved, Vet Approved
Cholecalciferol	The metabolism of Astemizole can be decreased when combined with Cholecalciferol.	Approved, Nutraceutical
Cimetidine	The serum concentration of Cimetidine can be increased when it is combined with Astemizole.	Approved
Cinacalcet	The metabolism of Astemizole can be decreased when combined with Cinacalcet.	Approved
Ciprofloxacin	The serum concentration of Ciprofloxacin can be increased when it is combined with Astemizole.	Approved, Investigational
Cisplatin	The serum concentration of Cisplatin can be increased when it is combined with Astemizole.	Approved
Citalopram	The serum concentration of Citalopram can be increased when it is combined with Astemizole.	Approved
Clarithromycin	The serum concentration of Astemizole can be increased when it is combined with Clarithromycin.	Approved
Clemastine	The metabolism of Astemizole can be decreased when combined with Clemastine.	Approved
Clobazam	The serum concentration of Clobazam can be increased when it is combined with Astemizole.	Approved, Illicit
Clomifene	The serum concentration of Clomifene can be increased when it is combined with Astemizole.	Approved, Investigational
Clomipramine	The metabolism of Astemizole can be decreased when combined with Clomipramine.	Approved, Vet Approved
Clonidine	The serum concentration of Clonidine can be increased when it is combined with Astemizole.	Approved
Clopidogrel	The serum concentration of Clopidogrel can be increased when it is combined with Astemizole.	Approved, Nutraceutical
Clotrimazole	The metabolism of Astemizole can be decreased when combined with Clotrimazole.	Approved, Vet Approved
Clozapine	The serum concentration of Clozapine can be increased when it is combined with Astemizole.	Approved
Cobicistat	The serum concentration of Astemizole can be increased when it is combined with Cobicistat.	Approved
Cobimetinib	The serum concentration of Cobimetinib can be increased when it is combined with Astemizole.	Approved
Cocaine	The metabolism of Astemizole can be decreased when combined with Cocaine.	Approved, Illicit
Colchicine	The serum concentration of Colchicine can be increased when it is combined with Astemizole.	Approved
Conivaptan	The serum concentration of Astemizole can be increased when it is combined with Conivaptan.	Approved, Investigational
Conjugated estrogens	The serum concentration of Conjugated Equine Estrogens can be increased when it is combined with Astemizole.	Approved
Crizotinib	The metabolism of Astemizole can be decreased when combined with Crizotinib.	Approved
Cyclosporine	The metabolism of Astemizole can be decreased when combined with Cyclosporine.	Approved, Investigational, Vet Approved
Dabigatran etexilate	The serum concentration of the active metabolites of Dabigatran etexilate can be increased when Dabigatran etexilate is used in combination with Astemizole.	Approved
Dabrafenib	The serum concentration of Astemizole can be decreased when it is combined with Dabrafenib.	Approved
Dactinomycin	The serum concentration of Dactinomycin can be increased when it is combined with Astemizole.	Approved
Dapagliflozin	The serum concentration of Dapagliflozin can be increased when it is combined with Astemizole.	Approved
Darifenacin	The metabolism of Astemizole can be decreased when combined with Darifenacin.	Approved, Investigational
Darunavir	The serum concentration of Astemizole can be increased when it is combined with Darunavir.	Approved
Dasatinib	The serum concentration of Astemizole can be increased when it is combined with Dasatinib.	Approved, Investigational
Daunorubicin	The serum concentration of Daunorubicin can be increased when it is combined with Astemizole.	Approved
Debrisoquin	The serum concentration of Debrisoquin can be increased when it is combined with Astemizole.	Approved
Deferasirox	The serum concentration of Astemizole can be decreased when it is combined with Deferasirox.	Approved, Investigational
Delavirdine	Delavirdine may increase the arrhythmogenic activities of Astemizole.	Approved
Desipramine	The metabolism of Astemizole can be decreased when combined with Desipramine.	Approved
Dexamethasone	The serum concentration of Astemizole can be decreased when it is combined with Dexamethasone.	Approved, Investigational, Vet Approved
Dextroamphetamine	Dextroamphetamine may decrease the sedative activities of Astemizole.	Approved, Illicit
Diazepam	The serum concentration of Diazepam can be increased when it is combined with Astemizole.	Approved, Illicit, Vet Approved
Diethylpropion	Diethylpropion may decrease the sedative activities of Astemizole.	Approved, Illicit
Diethylstilbestrol	The serum concentration of Diethylstilbestrol can be increased when it is combined with Astemizole.	Approved
Digitoxin	The serum concentration of Digitoxin can be increased when it is combined with Astemizole.	Approved
Digoxin	The serum concentration of Digoxin can be increased when it is combined with Astemizole.	Approved
Dihydroergotamine	The metabolism of Astemizole can be decreased when combined with Dihydroergotamine.	Approved
Dihydrotestosterone	The serum concentration of Dihydrotestosterone can be increased when it is combined with Astemizole.	Illicit
Diltiazem	The metabolism of Astemizole can be decreased when combined with Diltiazem.	Approved
Diphenhydramine	The metabolism of Astemizole can be decreased when combined with Diphenhydramine.	Approved
Dipyridamole	The serum concentration of Dipyridamole can be increased when it is combined with Astemizole.	Approved
Docetaxel	The serum concentration of Docetaxel can be increased when it is combined with Astemizole.	Approved, Investigational
Domperidone	The serum concentration of Domperidone can be increased when it is combined with Astemizole.	Approved, Investigational, Vet Approved
Doxorubicin	The serum concentration of Doxorubicin can be increased when it is combined with Astemizole.	Approved, Investigational
Doxycycline	The metabolism of Astemizole can be decreased when combined with Doxycycline.	Approved, Investigational, Vet Approved
Dronedarone	The metabolism of Astemizole can be decreased when combined with Dronedarone.	Approved
Duloxetine	The metabolism of Astemizole can be decreased when combined with Duloxetine.	Approved
Edoxaban	The serum concentration of Edoxaban can be increased when it is combined with Astemizole.	Approved
Efavirenz	The serum concentration of Astemizole can be decreased when it is combined with Efavirenz.	Approved, Investigational
Eletriptan	The serum concentration of Eletriptan can be increased when it is combined with Astemizole.	Approved, Investigational
Eliglustat	The metabolism of Astemizole can be decreased when combined with Eliglustat.	Approved
Enzalutamide	The serum concentration of Astemizole can be decreased when it is combined with Enzalutamide.	Approved
Epinastine	The serum concentration of Epinastine can be increased when it is combined with Astemizole.	Approved, Investigational
Erlotinib	The serum concentration of Erlotinib can be increased when it is combined with Astemizole.	Approved, Investigational
Erythromycin	The metabolism of Astemizole can be decreased when combined with Erythromycin.	Approved, Vet Approved
Eslicarbazepine acetate	The serum concentration of Astemizole can be decreased when it is combined with Eslicarbazepine acetate.	Approved
Estradiol	The serum concentration of Estradiol can be increased when it is combined with Astemizole.	Approved, Investigational, Vet Approved
Estriol	The serum concentration of Estriol can be increased when it is combined with Astemizole.	Approved, Vet Approved
Estrone	The serum concentration of Estrone can be increased when it is combined with Astemizole.	Approved
Ethinyl Estradiol	The serum concentration of Ethinyl Estradiol can be increased when it is combined with Astemizole.	Approved
Etoposide	The serum concentration of Etoposide can be increased when it is combined with Astemizole.	Approved
Etravirine	The serum concentration of Astemizole can be decreased when it is combined with Etravirine.	Approved
Everolimus	The serum concentration of Everolimus can be increased when it is combined with Astemizole.	Approved
Ezetimibe	The serum concentration of Ezetimibe can be increased when it is combined with Astemizole.	Approved
Fesoterodine	The serum concentration of Fesoterodine can be increased when it is combined with Astemizole.	Approved
Fexofenadine	The serum concentration of Fexofenadine can be increased when it is combined with Astemizole.	Approved
Fidaxomicin	The serum concentration of Fidaxomicin can be increased when it is combined with Astemizole.	Approved
Fluconazole	The metabolism of Astemizole can be decreased when combined with Fluconazole.	Approved
Fluoxetine	The metabolism of Astemizole can be decreased when combined with Fluoxetine.	Approved, Vet Approved
Fluticasone furoate	The serum concentration of Fluticasone furoate can be increased when it is combined with Astemizole.	Approved
Fluvoxamine	The metabolism of Astemizole can be decreased when combined with Fluvoxamine.	Approved, Investigational
Fosamprenavir	The metabolism of Astemizole can be decreased when combined with Fosamprenavir.	Approved
Fosaprepitant	The serum concentration of Astemizole can be increased when it is combined with Fosaprepitant.	Approved
Fosphenytoin	The metabolism of Astemizole can be increased when combined with Fosphenytoin.	Approved
Fusidic Acid	The serum concentration of Astemizole can be increased when it is combined with Fusidic Acid.	Approved
Gefitinib	The serum concentration of Gefitinib can be increased when it is combined with Astemizole.	Approved, Investigational
Gemcitabine	The serum concentration of Gemcitabine can be increased when it is combined with Astemizole.	Approved
Grazoprevir	The serum concentration of Grazoprevir can be increased when it is combined with Astemizole.	Approved
Grepafloxacin	The serum concentration of Grepafloxacin can be increased when it is combined with Astemizole.	Withdrawn
Haloperidol	The serum concentration of Haloperidol can be increased when it is combined with Astemizole.	Approved
Hyaluronidase	The therapeutic efficacy of Hyaluronidase can be decreased when used in combination with Astemizole.	Approved, Investigational
Hydrocortisone	The serum concentration of Hydrocortisone can be increased when it is combined with Astemizole.	Approved, Vet Approved
Hydroxyamphetamine	Hydroxyamphetamine hydrobromide may decrease the sedative activities of Astemizole.	Approved
Ibuprofen	The serum concentration of Ibuprofen can be increased when it is combined with Astemizole.	Approved
Idelalisib	The serum concentration of Astemizole can be increased when it is combined with Idelalisib.	Approved
Imatinib	The metabolism of Astemizole can be decreased when combined with Imatinib.	Approved
Imipramine	The serum concentration of Imipramine can be increased when it is combined with Astemizole.	Approved
Indacaterol	The serum concentration of Indacaterol can be increased when it is combined with Astemizole.	Approved
Indinavir	The serum concentration of Astemizole can be increased when it is combined with Indinavir.	Approved
Indomethacin	The serum concentration of Indomethacin can be increased when it is combined with Astemizole.	Approved, Investigational
Irinotecan	The serum concentration of Irinotecan can be increased when it is combined with Astemizole.	Approved, Investigational
Isavuconazonium	The metabolism of Astemizole can be decreased when combined with Isavuconazonium.	Approved, Investigational
Isoniazid	The metabolism of Astemizole can be decreased when combined with Isoniazid.	Approved
Isradipine	The metabolism of Astemizole can be decreased when combined with Isradipine.	Approved
Itraconazole	The serum concentration of Astemizole can be increased when it is combined with Itraconazole.	Approved, Investigational
Ivacaftor	The serum concentration of Astemizole can be increased when it is combined with Ivacaftor.	Approved
Ivermectin	The serum concentration of Ivermectin can be increased when it is combined with Astemizole.	Approved, Vet Approved
Ketazolam	The serum concentration of Ketazolam can be increased when it is combined with Astemizole.	Approved
Ketoconazole	Ketoconazole may increase the QTc-prolonging activities of Astemizole.	Approved, Investigational
Ketoconazole	The serum concentration of Astemizole can be increased when it is combined with Ketoconazole.	Approved, Investigational
Lamivudine	The serum concentration of Lamivudine can be increased when it is combined with Astemizole.	Approved, Investigational
Lamotrigine	The serum concentration of Lamotrigine can be increased when it is combined with Astemizole.	Approved, Investigational
Lansoprazole	The serum concentration of Lansoprazole can be increased when it is combined with Astemizole.	Approved, Investigational
Ledipasvir	The serum concentration of Ledipasvir can be increased when it is combined with Astemizole.	Approved
Lenalidomide	The serum concentration of Lenalidomide can be increased when it is combined with Astemizole.	Approved
Lenvatinib	The serum concentration of Lenvatinib can be increased when it is combined with Astemizole.	Approved
Levetiracetam	The serum concentration of Levetiracetam can be increased when it is combined with Astemizole.	Approved, Investigational
Levofloxacin	The serum concentration of Levofloxacin can be increased when it is combined with Astemizole.	Approved, Investigational
Levomilnacipran	The serum concentration of Levomilnacipran can be increased when it is combined with Astemizole.	Approved
Linagliptin	The serum concentration of Linagliptin can be increased when it is combined with Astemizole.	Approved
Lisdexamfetamine	Lisdexamfetamine may decrease the sedative activities of Astemizole.	Approved, Investigational
Loperamide	The serum concentration of Loperamide can be increased when it is combined with Astemizole.	Approved
Lopinavir	The serum concentration of Astemizole can be increased when it is combined with Lopinavir.	Approved
Lorcaserin	The metabolism of Astemizole can be decreased when combined with Lorcaserin.	Approved
Losartan	The serum concentration of Losartan can be increased when it is combined with Astemizole.	Approved
Lovastatin	The metabolism of Astemizole can be decreased when combined with Lovastatin.	Approved, Investigational
Luliconazole	The serum concentration of Astemizole can be increased when it is combined with Luliconazole.	Approved
Lumacaftor	The metabolism of Astemizole can be increased when combined with Lumacaftor.	Approved
Lumefantrine	The metabolism of Astemizole can be decreased when combined with Lumefantrine.	Approved
Mannitol	The serum concentration of Mannitol can be increased when it is combined with Astemizole.	Approved, Investigational
Mephedrone	Mephedrone may decrease the sedative activities of Astemizole.	Investigational
Mephentermine	Mephentermine may decrease the sedative activities of Astemizole.	Approved
Methadone	The metabolism of Astemizole can be decreased when combined with Methadone.	Approved
Methamphetamine	Methamphetamine may decrease the sedative activities of Astemizole.	Approved, Illicit
Methotrexate	The serum concentration of Methotrexate can be increased when it is combined with Astemizole.	Approved
Methotrimeprazine	The metabolism of Astemizole can be decreased when combined with Methotrimeprazine.	Approved
Methylprednisolone	The serum concentration of Methylprednisolone can be increased when it is combined with Astemizole.	Approved, Vet Approved
Metoprolol	The serum concentration of Metoprolol can be increased when it is combined with Astemizole.	Approved, Investigational
Midazolam	The serum concentration of Midazolam can be increased when it is combined with Astemizole.	Approved, Illicit
Mifepristone	The serum concentration of Astemizole can be increased when it is combined with Mifepristone.	Approved, Investigational
Mirabegron	The serum concentration of Mirabegron can be increased when it is combined with Astemizole.	Approved
Mitotane	The serum concentration of Astemizole can be decreased when it is combined with Mitotane.	Approved
Mitoxantrone	The serum concentration of Mitoxantrone can be increased when it is combined with Astemizole.	Approved, Investigational
MMDA	MMDA may decrease the sedative activities of Astemizole.	Experimental, Illicit
Modafinil	The serum concentration of Astemizole can be decreased when it is combined with Modafinil.	Approved, Investigational
Morphine	The serum concentration of Morphine can be increased when it is combined with Astemizole.	Approved, Investigational
Mycophenolate mofetil	The serum concentration of Mycophenolate mofetil can be increased when it is combined with Astemizole.	Approved, Investigational
Nadolol	The serum concentration of Nadolol can be increased when it is combined with Astemizole.	Approved
Nafcillin	The serum concentration of Astemizole can be decreased when it is combined with Nafcillin.	Approved
Naloxegol	The serum concentration of Naloxegol can be increased when it is combined with Astemizole.	Approved
Naloxone	The serum concentration of Naloxone can be increased when it is combined with Astemizole.	Approved, Vet Approved
Nefazodone	The serum concentration of Astemizole can be increased when it is combined with Nefazodone.	Approved, Withdrawn
Nelfinavir	The serum concentration of Astemizole can be increased when it is combined with Nelfinavir.	Approved
Netupitant	The serum concentration of Astemizole can be increased when it is combined with Netupitant.	Approved
Nevirapine	The metabolism of Astemizole can be increased when combined with Nevirapine.	Approved
Nicardipine	The serum concentration of Nicardipine can be increased when it is combined with Astemizole.	Approved
Nifedipine	The serum concentration of Nifedipine can be increased when it is combined with Astemizole.	Approved
Nilotinib	The metabolism of Astemizole can be decreased when combined with Nilotinib.	Approved, Investigational
Nintedanib	The serum concentration of Nintedanib can be increased when it is combined with Astemizole.	Approved
Nizatidine	The serum concentration of Nizatidine can be increased when it is combined with Astemizole.	Approved
Olanzapine	The serum concentration of Olanzapine can be increased when it is combined with Astemizole.	Approved, Investigational
Olaparib	The metabolism of Astemizole can be decreased when combined with Olaparib.	Approved
Ombitasvir	The serum concentration of Ombitasvir can be increased when it is combined with Astemizole.	Approved
Osimertinib	The serum concentration of Astemizole can be increased when it is combined with Osimertinib.	Approved
Paclitaxel	The serum concentration of Paclitaxel can be increased when it is combined with Astemizole.	Approved, Vet Approved
Palbociclib	The serum concentration of Astemizole can be increased when it is combined with Palbociclib.	Approved
Panobinostat	The serum concentration of Astemizole can be increased when it is combined with Panobinostat.	Approved, Investigational
Paroxetine	The metabolism of Astemizole can be decreased when combined with Paroxetine.	Approved, Investigational
Pazopanib	The serum concentration of Pazopanib can be increased when it is combined with Astemizole.	Approved
Peginterferon alfa-2b	The serum concentration of Astemizole can be decreased when it is combined with Peginterferon alfa-2b.	Approved
Pentobarbital	The metabolism of Astemizole can be increased when combined with Pentobarbital.	Approved, Vet Approved
Phenobarbital	The metabolism of Astemizole can be increased when combined with Phenobarbital.	Approved
Phentermine	Phentermine may decrease the sedative activities of Astemizole.	Approved, Illicit
Phenytoin	The metabolism of Astemizole can be increased when combined with Phenytoin.	Approved, Vet Approved
Pitavastatin	The serum concentration of Pitavastatin can be increased when it is combined with Astemizole.	Approved
Pomalidomide	The serum concentration of Pomalidomide can be increased when it is combined with Astemizole.	Approved
Ponatinib	The serum concentration of Ponatinib can be increased when it is combined with Astemizole.	Approved
Posaconazole	The serum concentration of Astemizole can be increased when it is combined with Posaconazole.	Approved, Investigational, Vet Approved
Pravastatin	The serum concentration of Pravastatin can be increased when it is combined with Astemizole.	Approved
Prazosin	The serum concentration of Prazosin can be increased when it is combined with Astemizole.	Approved
Prednisolone	The serum concentration of Prednisolone can be increased when it is combined with Astemizole.	Approved, Vet Approved
Prednisone	The serum concentration of Prednisone can be increased when it is combined with Astemizole.	Approved, Vet Approved
Primidone	The metabolism of Astemizole can be increased when combined with Primidone.	Approved, Vet Approved
Progesterone	The serum concentration of Progesterone can be increased when it is combined with Astemizole.	Approved, Vet Approved
Promazine	The metabolism of Astemizole can be decreased when combined with Promazine.	Approved, Vet Approved
Propranolol	The serum concentration of Propranolol can be increased when it is combined with Astemizole.	Approved, Investigational
Prucalopride	The serum concentration of Prucalopride can be increased when it is combined with Astemizole.	Approved
Pseudoephedrine	Pseudoephedrine may decrease the sedative activities of Astemizole.	Approved
Quetiapine	The serum concentration of Quetiapine can be increased when it is combined with Astemizole.	Approved
Quinidine	The metabolism of Astemizole can be decreased when combined with Quinidine.	Approved
Quinine	The serum concentration of Quinine can be increased when it is combined with Astemizole.	Approved
Ranitidine	The serum concentration of Ranitidine can be increased when it is combined with Astemizole.	Approved
Ranolazine	The serum concentration of Ranolazine can be increased when it is combined with Astemizole.	Approved, Investigational
Reserpine	The serum concentration of Reserpine can be increased when it is combined with Astemizole.	Approved
Rifabutin	The metabolism of Astemizole can be increased when combined with Rifabutin.	Approved
Rifampicin	The metabolism of Astemizole can be increased when combined with Rifampicin.	Approved
Rifapentine	The metabolism of Astemizole can be increased when combined with Rifapentine.	Approved
Rifaximin	The serum concentration of Rifaximin can be increased when it is combined with Astemizole.	Approved, Investigational
Risperidone	The serum concentration of Risperidone can be increased when it is combined with Astemizole.	Approved, Investigational
Ritobegron	Ritobegron may decrease the sedative activities of Astemizole.	Investigational
Ritonavir	The serum concentration of Astemizole can be increased when it is combined with Ritonavir.	Approved, Investigational
Rivaroxaban	The serum concentration of Rivaroxaban can be increased when it is combined with Astemizole.	Approved
Rolapitant	The metabolism of Astemizole can be decreased when combined with Rolapitant.	Approved
Romidepsin	The serum concentration of Romidepsin can be increased when it is combined with Astemizole.	Approved, Investigational
Ropinirole	The metabolism of Astemizole can be decreased when combined with Ropinirole.	Approved, Investigational
Salicylic acid	The serum concentration of Salicylic acid can be increased when it is combined with Astemizole.	Approved, Vet Approved
Saquinavir	The serum concentration of Astemizole can be increased when it is combined with Saquinavir.	Approved, Investigational
Selexipag	The serum concentration of Selexipag can be increased when it is combined with Astemizole.	Approved
Sertraline	The metabolism of Astemizole can be decreased when combined with Sertraline.	Approved
Sildenafil	The metabolism of Astemizole can be decreased when combined with Sildenafil.	Approved, Investigational
Silodosin	The serum concentration of Silodosin can be increased when it is combined with Astemizole.	Approved
Siltuximab	The serum concentration of Astemizole can be decreased when it is combined with Siltuximab.	Approved
Simeprevir	The serum concentration of Astemizole can be increased when it is combined with Simeprevir.	Approved
Sitagliptin	The serum concentration of Sitagliptin can be increased when it is combined with Astemizole.	Approved, Investigational
Sofosbuvir	The serum concentration of Sofosbuvir can be increased when it is combined with Astemizole.	Approved
Sorafenib	The serum concentration of Sorafenib can be increased when it is combined with Astemizole.	Approved, Investigational
Sparfloxacin	The serum concentration of Sparfloxacin can be increased when it is combined with Astemizole.	Approved
Sphingosine	The serum concentration of Sphingosine can be increased when it is combined with Astemizole.	Experimental
St. John's Wort	The serum concentration of Astemizole can be decreased when it is combined with St. John's Wort.	Nutraceutical
Stiripentol	The serum concentration of Astemizole can be increased when it is combined with Stiripentol.	Approved
Sulfisoxazole	The metabolism of Astemizole can be decreased when combined with Sulfisoxazole.	Approved, Vet Approved
Tacrolimus	The serum concentration of Tacrolimus can be increased when it is combined with Astemizole.	Approved, Investigational
Tamoxifen	The serum concentration of Tamoxifen can be increased when it is combined with Astemizole.	Approved
Taurocholic Acid	The serum concentration of Taurocholic Acid can be increased when it is combined with Astemizole.	Experimental
Technetium Tc-99m sestamibi	The serum concentration of Technetium Tc-99m sestamibi can be increased when it is combined with Astemizole.	Approved
Telaprevir	The serum concentration of Astemizole can be increased when it is combined with Telaprevir.	Withdrawn
Telithromycin	The serum concentration of Astemizole can be increased when it is combined with Telithromycin.	Approved
Temsirolimus	The serum concentration of Temsirolimus can be increased when it is combined with Astemizole.	Approved
Terbinafine	The metabolism of Astemizole can be decreased when combined with Terbinafine.	Approved, Investigational, Vet Approved
Thioridazine	The metabolism of Astemizole can be decreased when combined with Thioridazine.	Withdrawn
Ticagrelor	The serum concentration of Ticagrelor can be increased when it is combined with Astemizole.	Approved
Ticlopidine	The metabolism of Astemizole can be decreased when combined with Ticlopidine.	Approved
Timolol	The serum concentration of Timolol can be increased when it is combined with Astemizole.	Approved
Tipranavir	The metabolism of Astemizole can be decreased when combined with Tipranavir.	Approved, Investigational
Tocilizumab	The serum concentration of Astemizole can be decreased when it is combined with Tocilizumab.	Approved
Tolvaptan	The serum concentration of Tolvaptan can be increased when it is combined with Astemizole.	Approved
Topotecan	The serum concentration of Topotecan can be increased when it is combined with Astemizole.	Approved, Investigational
Toremifene	The serum concentration of Toremifene can be increased when it is combined with Astemizole.	Approved, Investigational
Tranylcypromine	The metabolism of Astemizole can be decreased when combined with Tranylcypromine.	Approved
Trastuzumab emtansine	The serum concentration of Trastuzumab emtansine can be increased when it is combined with Astemizole.	Approved
Ulipristal	The serum concentration of Ulipristal can be increased when it is combined with Astemizole.	Approved
Umeclidinium	The serum concentration of Umeclidinium can be increased when it is combined with Astemizole.	Approved
Vecuronium	The serum concentration of Vecuronium can be increased when it is combined with Astemizole.	Approved
Venetoclax	The serum concentration of Venetoclax can be increased when it is combined with Astemizole.	Approved
Venlafaxine	The metabolism of Astemizole can be decreased when combined with Venlafaxine.	Approved
Verapamil	The metabolism of Astemizole can be decreased when combined with Verapamil.	Approved
Vinblastine	The serum concentration of Vinblastine can be increased when it is combined with Astemizole.	Approved
Vincristine	The serum concentration of Vincristine can be increased when it is combined with Astemizole.	Approved, Investigational
Vismodegib	The serum concentration of Vismodegib can be increased when it is combined with Astemizole.	Approved
Voriconazole	The serum concentration of Astemizole can be increased when it is combined with Voriconazole.	Approved, Investigational
Zidovudine	The serum concentration of Zidovudine can be increased when it is combined with Astemizole.	Approved
Ziprasidone	The metabolism of Astemizole can be decreased when combined with Ziprasidone.	Approved

Food Interactions

Take on an empty stomach, food decreases absorption by 60%.

References

Synthesis Reference

Godelieve Irma Christine Maria Heylen, Cornelus Gerardus Maria Janssen, Jurzak Mirek, Henricus Petrus Martinus Maria Van Assouw, "Radiolabeled astemizole and method of making." U.S. Patent US07541476, issued June 02, 2009.

US07541476

General 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:16723379 ]
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:16816845 ]

External Links

Resource	Link
Human Metabolome Database (HMDB)	HMDB14775
KEGG Drug	D00234
KEGG Compound	C06832
PubChem Compound	2247
PubChem Substance	46508569
ChemSpider	2160
BindingDB	24226
ChEBI	2896
ChEMBL	CHEMBL296419
Therapeutic Targets Database	DAP000326
PharmGKB	PA448498
IUPHAR	2603
Guide to Pharmacology	2603
Drug Product Database	1879
RxList	http://www.rxlist.com/cgi/generic/astem.htm
Drugs.com	http://www.drugs.com/mtm/astemizole.html
Wikipedia	Astemizole

ATC Codes

R06AX11 — Astemizole

AHFS Codes

Not Available

PDB Entries

Not Available

FDA label

Not Available

MSDS

Download (57.2 KB)

Clinical Trials

Not Available

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage forms

Form	Route	Strength
Tablet	Oral	10 mg
Suspension	Oral	2 mg

Prices

Not Available

Patents

Not Available

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	149.1 °C	PhysProp
water solubility	432 mg/L	Not Available
logP	5.8	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.0012 mg/mL	ALOGPS
logP	5.92	ALOGPS
logP	5.39	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Basic)	8.75	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	42.32 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	135.64 m³·mol^-1	ChemAxon
Polarizability	52.08 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted ADMET features

Property	Value	Probability
Human Intestinal Absorption	+	1.0
Blood Brain Barrier	+	0.765
Caco-2 permeable	+	0.5217
P-glycoprotein substrate	Substrate	0.8162
P-glycoprotein inhibitor I	Inhibitor	0.8563
P-glycoprotein inhibitor II	Inhibitor	0.8995
Renal organic cation transporter	Inhibitor	0.7708
CYP450 2C9 substrate	Non-substrate	0.8732
CYP450 2D6 substrate	Substrate	0.8918
CYP450 3A4 substrate	Substrate	0.6777
CYP450 1A2 substrate	Inhibitor	0.9107
CYP450 2C9 inhibitor	Non-inhibitor	0.9071
CYP450 2D6 inhibitor	Inhibitor	0.8932
CYP450 2C19 inhibitor	Inhibitor	0.8994
CYP450 3A4 inhibitor	Non-inhibitor	0.5127
CYP450 inhibitory promiscuity	High CYP Inhibitory Promiscuity	0.9096
Ames test	Non AMES toxic	0.6444
Carcinogenicity	Non-carcinogens	0.9553
Biodegradation	Not ready biodegradable	1.0
Rat acute toxicity	2.2847 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Strong inhibitor	0.9267
hERG inhibition (predictor II)	Inhibitor	0.8575

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum Type	Description	Splash Key
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available

Taxonomy

Description

This compound belongs to the class of chemical entities known as benzimidazoles. These are organic compounds containing a benzene ring fused to an imidazole ring (five member ring containing a nitrogen atom, 4 carbon atoms, and two double bonds).

Kingdom

Chemical entities

Super Class

Organic compounds

Class

Organoheterocyclic compounds

Sub Class

Benzimidazoles

Direct Parent

Benzimidazoles

Alternative Parents

Phenethylamines / Anisoles / Methoxybenzenes / Phenoxy compounds / Alkyl aryl ethers / Fluorobenzenes / Aralkylamines / N-substituted imidazoles / Aryl fluorides / Piperidines

Substituents

Benzimidazole / Phenethylamine / Anisole / Phenoxy compound / Phenol ether / Methoxybenzene / Alkyl aryl ether / Fluorobenzene / Halobenzene / Aralkylamine

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

piperidines, benzimidazoles (CHEBI:2896 )

Targets

Details

1. Histamine H1 receptor

Kind: Protein
Organism: Human
Pharmacological action: yes
Actions: antagonist

General Function:: Histamine receptor activity
Specific Function:: In peripheral tissues, the H1 subclass of histamine receptors mediates the contraction of smooth muscles, increase in capillary permeability due to contraction of terminal venules, and catecholamine release from adrenal medulla, as well as mediating neurotransmission in the central nervous system.
Gene Name:: HRH1
Uniprot ID:: P35367
Molecular Weight:: 55783.61 Da

References

Salata JJ, Jurkiewicz NK, Wallace AA, Stupienski RF 3rd, Guinosso PJ Jr, Lynch JJ Jr: Cardiac electrophysiological actions of the histamine H1-receptor antagonists astemizole and terfenadine compared with chlorpheniramine and pyrilamine. Circ Res. 1995 Jan;76(1):110-9. [PubMed:8001268 ]
Howarth PH, Emanuel MB, Holgate ST: Astemizole, a potent histamine H1-receptor antagonist: effect in allergic rhinoconjunctivitis, on antigen and histamine induced skin weal responses and relationship to serum levels. Br J Clin Pharmacol. 1984 Jul;18(1):1-8. [PubMed:6146346 ]
Kaliner MA, Check WA: Non-sedating antihistamines. Allergy Proc. 1988 Nov-Dec;9(6):649-63. [PubMed:3147222 ]
Cavero I, Mestre M, Guillon JM, Heuillet E, Roach AG: Preclinical in vitro cardiac electrophysiology: a method of predicting arrhythmogenic potential of antihistamines in humans? Drug Saf. 1999;21 Suppl 1:19-31; discussion 81-7. [PubMed:10597865 ]
Llenas J, Cardelus I, Heredia A, de Mora F, Gristwood RW: Cardiotoxicity of histamine and the possible role of histamine in the arrhythmogenesis produced by certain antihistamines. Drug Saf. 1999;21 Suppl 1:33-8; discussion 81-7. [PubMed:10597866 ]
Richards DM, Brogden RN, Heel RC, Speight TM, Avery GS: Astemizole. A review of its pharmacodynamic properties and therapeutic efficacy. Drugs. 1984 Jul;28(1):38-61. [PubMed:6204835 ]
Krstenansky PM, Cluxton RJ Jr: Astemizole: a long-acting, nonsedating antihistamine. Drug Intell Clin Pharm. 1987 Dec;21(12):947-53. [PubMed:2892659 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Details

2. Potassium voltage-gated channel subfamily H member 2

Kind: Protein
Organism: Human
Pharmacological action: unknown
Actions: inhibitor

General Function:: Voltage-gated potassium channel activity involved in ventricular cardiac muscle cell action potential repolarization
Specific Function:: Pore-forming (alpha) subunit of voltage-gated inwardly rectifying potassium channel. Channel properties are modulated by cAMP and subunit assembly. Mediates the rapidly activating component of the delayed rectifying potassium current in heart (IKr). Isoforms USO have no channel activity by themself, but modulates channel characteristics by forming heterotetramers with other isoforms which are r...
Gene Name:: KCNH2
Uniprot ID:: Q12809
Molecular Weight:: 126653.52 Da

References

Zhou Z, Vorperian VR, Gong Q, Zhang S, January CT: Block of HERG potassium channels by the antihistamine astemizole and its metabolites desmethylastemizole and norastemizole. J Cardiovasc Electrophysiol. 1999 Jun;10(6):836-43. [PubMed:10376921 ]
Chachin M, Katayama Y, Yamada M, Horio Y, Ohmura T, Kitagawa H, Uchida S, Kurachi Y: Epinastine, a nonsedating histamine H1 receptor antagonist, has a negligible effect on HERG channel. Eur J Pharmacol. 1999 Jun 25;374(3):457-60. [PubMed:10422790 ]
Taglialatela M, Castaldo P, Pannaccione A, Giorgio G, Genovese A, Marone G, Annunziato L: Cardiac ion channels and antihistamines: possible mechanisms of cardiotoxicity. Clin Exp Allergy. 1999 Jul;29 Suppl 3:182-9. [PubMed:10444235 ]
Grzelewska-Rzymowska I, Pietrzkowicz M, Gorska M: [The effect of second generation histamine antagonists on the heart]. Pneumonol Alergol Pol. 2001;69(3-4):217-26. [PubMed:11575008 ]
Chiu PJ, Marcoe KF, Bounds SE, Lin CH, Feng JJ, Lin A, Cheng FC, Crumb WJ, Mitchell R: Validation of a [3H]astemizole binding assay in HEK293 cells expressing HERG K+ channels. J Pharmacol Sci. 2004 Jul;95(3):311-9. [PubMed:15272206 ]

Details

3. Potassium voltage-gated channel subfamily H member 1

Kind: Protein
Organism: Human
Pharmacological action: unknown

General Function:: Phosphorelay sensor kinase activity
Specific Function:: Pore-forming (alpha) subunit of a voltage-gated delayed rectifier potassium channel (PubMed:22732247). Channel properties may be modulated by subunit assembly, but not by cyclic nucleotides (By similarity). Mediates IK(NI) current in myoblasts (PubMed:9738473). Involved in the regulation of cell proliferation and differentiation, in particular adipogenic and osteogenic differentiation in bone m...
Gene Name:: KCNH1
Uniprot ID:: O95259
Molecular Weight:: 111421.76 Da

References

Garcia-Ferreiro RE, Kerschensteiner D, Major F, Monje F, Stuhmer W, Pardo LA: Mechanism of block of hEag1 K+ channels by imipramine and astemizole. J Gen Physiol. 2004 Oct;124(4):301-17. Epub 2004 Sep 13. [PubMed:15365094 ]

Details

4. Microtubule-associated protein tau

Kind: Protein
Organism: Human
Pharmacological action: unknown

General Function:: Structural constituent of cytoskeleton
Specific Function:: Promotes microtubule assembly and stability, and might be involved in the establishment and maintenance of neuronal polarity. The C-terminus binds axonal microtubules while the N-terminus binds neural plasma membrane components, suggesting that tau functions as a linker protein between both. Axonal polarity is predetermined by TAU/MAPT localization (in the neuronal cell) in the domain of the ce...
Gene Name:: MAPT
Uniprot ID:: P10636
Molecular Weight:: 78927.025 Da

References

Rojo LE, Alzate-Morales J, Saavedra IN, Davies P, Maccioni RB: Selective interaction of lansoprazole and astemizole with tau polymers: potential new clinical use in diagnosis of Alzheimer's disease. J Alzheimers Dis. 2010;19(2):573-89. doi: 10.3233/JAD-2010-1262. [PubMed:20110603 ]

Enzymes

Details

1. Cytochrome P450 3A4

Kind: Protein
Organism: Human
Pharmacological action: unknown
Actions: substrateinhibitor

General Function:: Vitamin d3 25-hydroxylase activity
Specific Function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular Weight:: 57342.67 Da

References

Nicolas JM, Whomsley R, Collart P, Roba J: In vitro inhibition of human liver drug metabolizing enzymes by second generation antihistamines. Chem Biol Interact. 1999 Nov 15;123(1):63-79. [PubMed:10597902 ]
Matsumoto S, Yamazoe Y: Involvement of multiple human cytochromes P450 in the liver microsomal metabolism of astemizole and a comparison with terfenadine. Br J Clin Pharmacol. 2001 Feb;51(2):133-42. [PubMed:11259984 ]
Cvetkovic RS, Goa KL: Lopinavir/ritonavir: a review of its use in the management of HIV infection. Drugs. 2003;63(8):769-802. [PubMed:12662125 ]
Goto A, Adachi Y, Inaba A, Nakajima H, Kobayashi H, Sakai K: Identification of human p450 isoforms involved in the metabolism of the antiallergic drug, oxatomide, and its inhibitory effect on enzyme activity. Biol Pharm Bull. 2004 May;27(5):684-90. [PubMed:15133245 ]
Goto A, Ueda K, Inaba A, Nakajima H, Kobayashi H, Sakai K: Identification of human P450 isoforms involved in the metabolism of the antiallergic drug, oxatomide, and its kinetic parameters and inhibition constants. Biol Pharm Bull. 2005 Feb;28(2):328-34. [PubMed:15684493 ]
Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]

Details

2. Cytochrome P450 3A5

Kind: Protein
Organism: Human
Pharmacological action: unknown
Actions: substrate

General Function:: Oxygen binding
Specific Function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:: CYP3A5
Uniprot ID:: P20815
Molecular Weight:: 57108.065 Da

References

Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]

Details

3. Cytochrome P450 3A7

Kind: Protein
Organism: Human
Pharmacological action: unknown
Actions: substrate

General Function:: Oxygen binding
Specific Function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:: CYP3A7
Uniprot ID:: P24462
Molecular Weight:: 57525.03 Da

References

Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]

Details

4. Cytochrome P450 2D6

Kind: Protein
Organism: Human
Pharmacological action: unknown
Actions: substrate

General Function:: Steroid hydroxylase activity
Specific Function:: Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:: CYP2D6
Uniprot ID:: P10635
Molecular Weight:: 55768.94 Da

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Details

5. Cytochrome P450 2J2

Kind: Protein
Organism: Human
Pharmacological action: unknown
Actions: substrate

General Function:: Steroid hydroxylase activity
Specific Function:: This enzyme metabolizes arachidonic acid predominantly via a NADPH-dependent olefin epoxidation to all four regioisomeric cis-epoxyeicosatrienoic acids. One of the predominant enzymes responsible for the epoxidation of endogenous cardiac arachidonic acid pools.
Gene Name:: CYP2J2
Uniprot ID:: P51589
Molecular Weight:: 57610.165 Da

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Transporters

Details

1. Multidrug resistance protein 1

Kind: Protein
Organism: Human
Pharmacological action: unknown
Actions: inhibitor

General Function:: Xenobiotic-transporting atpase activity
Specific Function:: Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name:: ABCB1
Uniprot ID:: P08183
Molecular Weight:: 141477.255 Da

References

Schwab D, Fischer H, Tabatabaei A, Poli S, Huwyler J: Comparison of in vitro P-glycoprotein screening assays: recommendations for their use in drug discovery. J Med Chem. 2003 Apr 24;46(9):1716-25. [PubMed:12699389 ]
Ishikawa M, Fujita R, Takayanagi M, Takayanagi Y, Sasaki K: Reversal of acquired resistance to doxorubicin in K562 human leukemia cells by astemizole. Biol Pharm Bull. 2000 Jan;23(1):112-5. [PubMed:10706423 ]

Drug created on June 13, 2005 07:24 / Updated on July 18, 2017 16:51

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Structure for DB00637 (Astemizole)

Targets

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Enzymes

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Transporters

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