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Substance Name: Terfenadine [USAN:USP:INN:BAN:JAN]
RN: 50679-08-8
UNII: 7BA5G9Y06Q
InChIKey: GUGOEEXESWIERI-UHFFFAOYSA-N

Note

  • A selective histamine H1-receptor antagonist devoid of central nervous system depressant activity. The drug was used for ALLERGY but withdrawn due to causing LONG QT SYNDROME.

Molecular Formula

  • C32-H41-N-O2

Molecular Weight

  • 471.681
 

Classification Codes

  • Antihistaminic
  • Drug / Therapeutic Agent
  • Histamine Agents
  • Histamine Antagonists
  • Histamine H1 Antagonists
  • Histamine H1 Antagonists, Non-Sedating
  • Human Data
  • Neurotransmitter Agents
  • Reproductive Effect

Names and Synonyms

Name of Substance

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

MeSH Heading

  • Terfenadine

Synonyms

  • 1-(4-tert-Butylphenyl)-4-(4-(alpha-hydroxybenzhydryl)piperidino)-butan-1-ol
  • 1-(p-tert-Butylphenyl)-4-(4'-(alpha-hydroxydiphenylmethyl)-1'-piperidyl)butanol
  • 1-Piperidinebutanol, alpha-(4-(1,1-dimethylethyl)phenyl)-4-(hydroxydiphenylmethyl)-
  • Aldaban
  • Allerplus
  • alpha-(4-(1,1-Dimethylethyl)phenyl)-4-(hydroxydiphenylmethyl)-1-piperidinebutanol
  • alpha-(p-tert-Butylphenyl)-4-(hydroxydiphenylmethyl)-1-piperidinebutanol
  • BRN 5857899
  • EINECS 256-710-8
  • HSDB 6508
  • MDL 9918
  • Nebralin
  • RMI 9918
  • Seldane
  • Teldane
  • Teldanex
  • Terdin
  • Terfen
  • Terfenadina
  • Terfenadina [INN-Spanish]
  • Terfenadine
  • Terfenadinum
  • Terfenadinum [INN-Latin]
  • Ternadin
  • Triludan
  • UNII-7BA5G9Y06Q

Systematic Names

  • 1-Piperidinebutanol, alpha-(4-(1,1-dimethylethyl)phenyl)-4-(hydroxydiphenylmethyl)-
  • Terfenadine

Registry Numbers

CAS Registry Number

  • 50679-08-8

FDA UNII

  • 7BA5G9Y06Q

System Generated Number

  • 0050679088

Structure Descriptors

InChI

1S/C32H41NO2/c1-31(2,3)26-18-16-25(17-19-26)30(34)15-10-22-33-23-20-29(21-24-33)32(35,27-11-6-4-7-12-27)28-13-8-5-9-14-28/h4-9,11-14,16-19,29-30,34-35H,10,15,20-24H2,1-3H3

InChIKey

GUGOEEXESWIERI-UHFFFAOYSA-N

Smiles

C(C1CCN(CCC[C@@H](c2ccc(C(C)(C)C)cc2)O)CC1)(c1ccccc1)(c1ccccc1)O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
child TDLo oral 3mg/kg (3mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" British Medical Journal. Vol. 293, Pg. 536, 1986.
dog LD oral > 1500mg/kg (1500mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING Oyo Yakuri. Pharmacometrics. Vol. 31, Pg. 845, 1986.
guinea pig LD50 oral > 2gm/kg (2000mg/kg)   Merck Index. Vol. 11, Pg. 1443, 1989.
human TDLo oral 857ug/kg (0.857mg/kg) BEHAVIORAL: CHANGES IN PSYCHOPHYSIOLOGICAL TESTS

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: ALTERATION OF OPERANT CONDITIONING
European Journal of Clinical Pharmacology. Vol. 47, Pg. 331, 1994.
mammal (species unspecified) LD50 intraperitoneal 43mg/kg (43mg/kg)   Journal of Medicinal Chemistry. Vol. 38, Pg. 2472, 1995.
man TDLo oral 857ug/kg (0.857mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" British Medical Journal. Vol. 293, Pg. 536, 1986.
man TDLo oral 36mg/kg/3W-I (36mg/kg) LIVER: "JAUNDICE, CHOLESTATIC"

LIVER: LIVER FUNCTION TESTS IMPAIRED
Lancet. Vol. 348, Pg. 552, 1996.
man TDLo oral 156mg/kg/13W- (156mg/kg) SKIN AND APPENDAGES (SKIN): HAIR: OTHER British Medical Journal. Vol. 291, Pg. 940, 1985.
mouse LD50 intraperitoneal 100mg/kg (100mg/kg)   United States Patent Document. Vol. #4908365,
mouse LD50 oral 5gm/kg (5000mg/kg)   Pharmacy International. Vol. 4, Pg. 252, 1983.
mouse LD50 subcutaneous > 4500mg/kg (4500mg/kg)   Drugs in Japan Vol. -, Pg. 707, 1990.
rat LD50 intraperitoneal 154mg/kg (154mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 21, Pg. 319, 1990.
rat LD50 oral 5gm/kg (5000mg/kg)   Pharmacy International. Vol. 4, Pg. 252, 1983.
rat LD50 subcutaneous > 1250mg/kg (1250mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 21, Pg. 319, 1990.
women TDLo oral 1200ug/kg (1.2mg/kg)   British Medical Journal. Vol. 293, Pg. 536, 1986.
women TDLo oral 1200ug/kg (1.2mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" British Medical Journal. Vol. 293, Pg. 536, 1986.
women TDLo oral 190mg/kg/23W- (190mg/kg) LIVER: LIVER FUNCTION TESTS IMPAIRED

LIVER: "JAUNDICE, OTHER OR UNCLASSIFIED"

BEHAVIORAL: MUSCLE WEAKNESS
Annals of Internal Medicine. Vol. 103, Pg. 634, 1985.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 147 deg C   EXP
log P (octanol-water) 7.620 (none)   EST
Water Solubility 0.0963 mg/L 25 EXP
Atmospheric OH Rate Constant 1.38E-10 cm3/molecule-sec 25 EST

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