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Product Details:

  • CAS No: 14976-57-9
  • AHFC code:
  • Synonyms: (+)-(2R)-2-(2-(((R)-p-Chloro-alpha-methyl-alpha-phenylbenzyl)oxy)ethyl)-1-methylpyrrolidine fumarate (1:1), (+)-2-(2-((p-Chloro-alpha-methyl-alpha-phenylbenzyl)oxy)ethyl)-1-methyl pyrrolidine fumarate, Agasten, Aloginan, Alphamin, Anhistan, Clemanil, Clemastine fumarate, Clemastine hydrogen fumarate, EINECS 239-055-2, Fuluminol, HSDB 6507, Inbestan, Kinotomin, Lacretin, Lecasol, Maikohis, Mallermin-F, Marsthine, Masletine, Meclastine hydrogen fumarate, Mecloprodine, Piloral, Pyrrolidine, 2-(2-(1-(4-chlorophenyl)-1-phenylethoxy)ethyl)-1-methyl-, (R-(R*,R*))-, (E)-2-butenedioate (1:1), Reconin, Tavegil, Tavegyl, Tavist, Tavist-1, Telgin-G, Topcare dayhist allergy, Trabest, UNII-19259EGQ3D, Xolamin
  • ATC Code:
  • Chemical Formula: C21-H26-Cl-N-O.C4-H4-O4
  • Molecular Weight:
  • Assay/Purity: Typically NLT 98%
  • DrugBank:
  • SMILES: c1([C,,](c2ccccc2)(OCC[C,,H]2[N,,](CCC2)C)C)ccc(Cl)cc1.C(=CC(O)=O)C(O)=O
  • InChl: InChI=1S/C21H26ClNO.C4H4O4/c1-21(17-7-4-3-5-8-17,18-10-12-19(22)13-11-18)24-16-14-20-9-6-15-23(20)2;5-3(6)1-2-4(7)8/h3-5,7-8,10-13,20H,6,9,14-16H2,1-2H3;1-2H,(H,5,6)(H,7,8)/b;2-1+/t20-,21-;/m1./s1
  • PubChem:
  • IUPAC: (R-(R*,R*))-2-(2-(1-(p-Chlorophenyl)-1-phenylethoxy)ethyl)- 1-methylpyrrolidinium hydrogen fumarate

Additional Details

Indication:
For the relief of symptoms associated with allergic rhinitis such as sneezing, rhinorrhea, pruritus and acrimation. Also for the management of mild, uncomplicated allergic skin manifestations of urticaria and angioedema. Used as self-medication for temporary relief of symptoms associated with the common cold.
Pharmacodynamics:
Clemastine is an antihistamine with anticholinergic (drying) and sedative side effects. Antihistamines competitively antagonize various physiological effects of histamine including increased capillary permeability and dilatation, the formation of edema, the “flare” and “itch” response, and gastrointestinal and respiratory smooth muscle constriction. Within the vascular tree, H1- receptor antagonists inhibit both the vasoconstrictor and vasodilator effects of histamine. Depending on the dose, H1- receptor antagonists can produce CNS stimulation or depression. Most antihistamines exhibit central and/or peripheral anticholinergic activity. Antihistamines act by competitively blocking H1- receptor sites. Antihistamines do not pharmacologically antagonize or chemically inactivate histamine, nor do they prevent the release of histamine.
Mode of Action:
Clemastine is a selective histamine H1 antagonist and binds to the histamine H1 receptor. This blocks the action of endogenous histamine, which subsequently leads to temporary relief of the negative symptoms brought on by histamine.
Metabolism:
Antihistamines appear to be metabolized in the liver chiefly via mono- and didemethylation and glucuronide conjugation.
Toxicity:
Oral LD50 in rat and mouse is 3550 mg/kg and 730 mg/kg, respectively. Antihistamine overdosage reactions may vary from central nervous system depression to stimulation. In children, stimulation predominates initially in a syndrome which may include excitement, hallucinations, ataxia, incoordination, muscle twitching, athetosis, hyperthermia, cyanosis convulsions, tremors, and hyperreflexia followed by postictal depression and cardio-respiratory arrest. Convulsions in children may be preceded by mild depression. Dry mouth, fixed dilated pupils, flushing of the face, and fever are common. In adults, CNS depression, ranging from drowsiness to coma, is more common.
General Reference:
Hayashi H, Okajima M, Yamada K: Atrial T (Ta) loop in dogs with or without atrial injury. Am Heart J. 1976 May;91(5):607-17. PubmedSchran HF, Petryk L, Chang CT, O’Connor R, Gelbert MB: The pharmacokinetics and bioavailability of clemastine and phenylpropanolamine in single-component and combination formulations. J Clin Pharmacol. 1996 Oct;36(10):911-22. Pubmed
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