ContaminantDB: Astemizole

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (15)XML

Record Information

Version

1.0

Creation Date

2009-07-21 20:27:18 UTC

Update Date

2026-05-14 16:44:46 UTC

Accession Number

CHEM002235

Identification

Common Name

Astemizole

Class

Small Molecule

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 It was withdrawn from market by the manufacturer in 1999 due to the potential to cause arrhythmias at high doses, especially when when taken with CYP inhibitors or grapefruit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

Contaminant Sources

EAFUS Chemicals
HMDB Contaminants - Urine
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Amine
Anti-Allergic Agent
Drug
Ether
Histamine Antagonist
Histamine H1 Antagonist, Non-Sedating
Human Neurotoxin
Metabolite
Organic Compound
Organofluoride
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-(p-Fluorobenzyl)-2-((1-(2-(p-methoxyphenyl)ethyl)piperid-4-yl)amino)benzimidazole	ChEBI
1-(p-Fluorobenzyl)-2-((1-(p-methoxyphenethyl)-4-piperidyl)amino)benzimidazole	ChEBI
Astemison	ChEBI
Astemizol	ChEBI
Astemizolum	ChEBI
Hismanal	Kegg
Alonga brand OF astemizole	HMDB
Astemizole alacan brand	HMDB
Astemizole byk brand	HMDB
Astemizole diba brand	HMDB
Astemizole esteve brand	HMDB
Astemizole senosiain brand	HMDB
Astemizole ratiopharm brand	HMDB
Esteve brand OF astemizole	HMDB
Fustery brand OF astemizole	HMDB
Histaminos	HMDB
ICN brand OF astemizole	HMDB
Rifedot	HMDB
Rimbol	HMDB
Senosiain brand OF astemizole	HMDB
Smaller brand OF astemizole	HMDB
Alonga, astemizol	HMDB
Astemina	HMDB
Astemizol alonga	HMDB
Astemizole icn brand	HMDB
Astemizole medinsa brand	HMDB
Astemizole merck brand	HMDB
Astemizole smaller brand	HMDB
Astemizole urbion brand	HMDB
Astemizole vita brand	HMDB
Astesen	HMDB
Hubermizol	HMDB
Laridal	HMDB
Lesvi brand OF astemizole	HMDB
Reig jofre brand OF astemizole	HMDB
Romadin	HMDB
Urbion brand OF astemizole	HMDB
Ratiopharm brand OF astemizole	HMDB
Ratiopharm, astemizol	HMDB
Astemizole alonga brand	HMDB
Astemizole elfar brand	HMDB
Astemizole fustery brand	HMDB
Astemizole janssen brand	HMDB
Astemizole lesvi brand	HMDB
Astemizole mcneil brand	HMDB
Astemizole septa brand	HMDB
Byk brand OF astemizole	HMDB
Diba brand OF astemizole	HMDB
Elfar brand OF astemizole	HMDB
Emdar	HMDB
Fustermizol	HMDB
McNeil brand OF astemizole	HMDB
Merck brand OF astemizole	HMDB
Simprox	HMDB
Urdrim	HMDB
Alacan brand OF astemizole	HMDB
Alermizol	HMDB
Astemizol ratiopharm	HMDB
Esmacen	HMDB
Janssen brand OF astemizole	HMDB
Medinsa brand OF astemizole	HMDB
Paralergin	HMDB
Retolen	HMDB
Septa brand OF astemizole	HMDB
Vita brand OF astemizole	HMDB

Chemical Formula

C₂₈H₃₁FN₄O

Average Molecular Mass

458.570 g/mol

Monoisotopic Mass

458.248 g/mol

CAS Registry Number

68844-77-9

IUPAC Name

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

Traditional Name

astemizole

SMILES

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

InChI Identifier

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

GXDALQBWZGODGZ-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds 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

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzimidazoles

Sub Class

Not Available

Direct Parent

Benzimidazoles

Alternative Parents

Substituents

Benzimidazole
Phenethylamine
Anisole
Phenoxy compound
Phenol ether
Methoxybenzene
Alkyl aryl ether
Fluorobenzene
Halobenzene
Aralkylamine
Piperidine
Benzenoid
Aryl fluoride
Aryl halide
N-substituted imidazole
Monocyclic benzene moiety
Heteroaromatic compound
Azole
Imidazole
Tertiary aliphatic amine
Tertiary amine
Azacycle
Ether
Hydrocarbon derivative
Amine
Organic oxygen compound
Organic nitrogen compound
Organohalogen compound
Organofluoride
Organonitrogen compound
Organooxygen compound
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

piperidines (CHEBI:2896 )
benzimidazoles (CHEBI:2896 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Biological Roles

H1-receptor antagonist

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	149.1°C
Boiling Point	Not Available
Solubility	432 mg/L

Predicted Properties

Property	Value	Source
Water Solubility	0.0012 g/L	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

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-1922000000-2742ecd8a8c6af4db428	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0110900000-7c47b2813568251daf1e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-052r-1947600000-b67040fd618da0f36a6a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0016-2940000000-e1a0cda3eae5d6bc1cf6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0010900000-e80e4e306be153aeab7c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0abc-0145900000-d00ee25e0101b4beb25a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01qd-3893000000-dae89e0c7d17da3e1c78	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0000900000-416ae1ceda818e4c922c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0200900000-3d85252f27ae2ba0258e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0570-1624900000-4ea28e09b60d7c3b3618	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0000900000-afe434091fa2787a5ed5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0000900000-142d31f8c19fb007efb7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a59-0794800000-0f835aeecbc38bc493f2	Spectrum

Toxicity Profile

Route of Exposure

Oral. Rapidly absorbed from the gastrointestinal tract.

Mechanism of Toxicity

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.

Metabolism

It is metabolized by CYP3A4. [Wikidpedia]. Almost completely metabolized in the liver and primarily excreted in the feces. Half Life: 1 day

Toxicity Values

LD50: 2052mg/kg (Mouse) (1)

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Astemizole tablets are indicated for the relief of symptoms associated with seasonal allergic rhinitis and chronic idiopathic urticaria. (6). 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.

Minimum Risk Level

Not Available

Health Effects

Cardiovascular adverse events. In some cases, recognition of severe arrhythmias has been preceded by episodes of syncope. Similarly, rare cases of hypotension, palpitations, and dizziness have also been reported with Astemizole use, which may reflect undetected ventricular arrhythmia. (6)

Symptoms

Not Available

Treatment

In the event of overdosage, supportive measures including gastric lavage and emesis should be employed. (5)

Concentrations

Not Available

External Links

DrugBank ID

DB00637

HMDB ID

HMDB0014775

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

Not Available

ECMDB ID

Not Available

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.

MSDS

Link

General References

1. 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.

2. 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.

Astemizole (CHEM002235)

Structure for CHEM002235: Astemizole