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Substance Name: Astemizole [USAN:USP:INN:BAN:JAN]
RN: 68844-77-9
UNII: 7HU6337315
InChIKey: GXDALQBWZGODGZ-UHFFFAOYSA-N

Note

  • Antihistamine drug now withdrawn from the market in many countries because of rare but potentially fatal side effects.

Molecular Formula

  • C28-H31-F-N4-O

Molecular Weight

  • 458.5779
 

Classification Codes

  • Anti-Allergic
  • Anti-Allergic Agents
  • Antihistaminic
  • Drug / Therapeutic Agent
  • Histamine Agents
  • Histamine Antagonists
  • Histamine H1 Antagonists
  • Histamine H1 Antagonists, Non-Sedating
  • Human Data
  • Neurotransmitter Agents
  • Reproductive Effect
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Names and Synonyms

Name of Substance

  • Astemizole
  • Astemizole [USAN:USP:INN:BAN:JAN]

MeSH Heading

  • Astemizole

Synonyms

  • 1-((4-Fluorophenyl)methyl)-N-(1-(2-(4-methoxyphenyl)ethyl)-4-piperidinyl)- 1H-benzimidazol-2-amine
  • 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
  • 1H-Benzimidazol-2-amine, 1-((4-fluorophenyl)methyl)-N-(1-(2-(4-methoxyphenyl)eth l)-4-piperidinyl)-
  • 1H-Benzimidazol-2-amine, 1-((4-fluorophenyl)methyl)-N-(1-(2-(4-methoxyphenyl)ethyl)-4-piperidinyl)-
  • Alermizol
  • Astemison
  • Astemizol
  • Astemizol [German]
  • Astemizol [INN-Spanish]
  • Astemizole
  • Astemizolum
  • Astemizolum [INN-Latin]
  • BRN 4830190
  • CCRIS 7595
  • EINECS 272-441-9
  • Hestazol
  • Hismanal
  • Histamen
  • Histaminos
  • HSDB 6799
  • Kelp
  • Laridal
  • Metodih
  • Novo-mastizol A
  • Paralergin
  • R 42512
  • R 43,512
  • Retolen
  • UNII-7HU6337315
  • Wareezol

Systematic Names

  • 1H-Benzimidazol-2-amine, 1-((4-fluorophenyl)methyl)-N-(1-(2-(4-methoxyphenyl)ethyl)-4-piperidinyl)-
  • Astemizole
  • Benzimidazole, 1-(p-fluorobenzyl)-2-((1-(2-(p-methoxyphenyl)ethyl)piperid-4-yl)amino)-

Registry Numbers

CAS Registry Number

  • 68844-77-9

FDA UNII

  • 7HU6337315

System Generated Number

  • 0068844779

Structure Descriptors

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

Smiles

COc1ccc(CCN2CCC(CC2)Nc3nc4ccccc4n3Cc5ccc(F)cc5)cc1

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 intravenous 21800ug/kg (21.8mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 33, Pg. 381, 1983.
dog LD50 oral > 320mg/kg (320mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 251, Pg. 39, 1981.
guinea pig LD50 oral 933mg/kg (933mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 251, Pg. 39, 1981.
infant TDLo oral 3500ug/kg (3.5mg/kg) CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP

CARDIAC: EKG CHANGES NOT DIAGNOSTIC OF ABOVE

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION
Pediatric Emergency Care. Vol. 12, Pg. 102, 1996.
mouse LD50 intravenous 35mg/kg (35mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 26, Pg. 239, 1995.
mouse LD50 oral 2560mg/kg (2560mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 251, Pg. 39, 1981.
mouse LD50 subcutaneous 1928mg/kg (1928mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 26, Pg. 239, 1995.
rat LD50 intravenous 28200ug/kg (28.2mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 33, Pg. 381, 1983.
rat LD50 oral > 2560mg/kg (2560mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 251, Pg. 39, 1981.
rat LD50 subcutaneous 355mg/kg (355mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 33, Pg. 381, 1983.
women TDLo oral 1200ug/kg (1.2mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION)

CARDIAC: EKG CHANGES NOT DIAGNOSTIC OF ABOVE
Pediatric Emergency Care. Vol. 12, Pg. 102, 1996.
women TDLo oral 4mg/kg (4mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Human Toxicology. Vol. 5, Pg. 43, 1986.
women TDLo oral 4mg/kg (4mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING

CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION)

BEHAVIORAL: COMA
British Medical Journal. Vol. 292, Pg. 660, 1986.
women TDLo oral 4mg/kg (4mg/kg) CARDIAC: CHANGE IN RATE Journal of Toxicology, Clinical Toxicology. Vol. 31, Pg. 121, 1993.
women TDLo oral 5400ug/kg (5.4mg/kg) CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP

CARDIAC: EKG CHANGES NOT DIAGNOSTIC OF ABOVE

BEHAVIORAL: GENERAL ANESTHETIC
Pediatric Emergency Care. Vol. 9, Pg. 23, 1993.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 149.1 deg C   EXP
log P (octanol-water) 6.430 (none)   EST
Atmospheric OH Rate Constant 3.60E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.