Clemastine fumarate

Clemastine fumarate Basic information
Product Name:Clemastine fumarate
Synonyms:CLEMASTINE FUMARATE;CLEMASTINE FUMARATE SALT;(+)-2-(2-((p-chloro-alpha-methyl-alpha-phenylbenzyl)oxy)ethyl)-1-methylpyrro;(+)-2-(2-((p-chloro-alpha-methyl-alpha-phenylbenzyl)oxy)ethyl)-1-methylpyrroli;(+)-lfumarate(1:1);1-methyl-2-(2-(methyl-p-chlorodiphenylmethyloxy)ethyl)pyrrolidine;(2R)-2-[2-[(1R)-1-(4-CHLOROPHENYLETHOXY)]ETHYL]-1-METHYL-2-PYRROLIDINE FUMARATE;2-(2-(1-(4-chlorophenyl)-1-phenylethoxy)ethyl)-1-methylpyrrolidine
CAS:14976-57-9
MF:C25H30ClNO5
MW:459.96
EINECS:239-055-2
Product Categories:antianaphylaxis;TAVIST;Histaminergics;Antagonists;Neurotransmitters;Aromatics;Chiral Reagents;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
Mol File:14976-57-9.mol
Clemastine fumarate Structure
Clemastine fumarate Chemical Properties
Melting point 158-162°C
alpha D21 +16.9° (methanol)
Boiling point 154°C (rough estimate)
density 1.0247 (rough estimate)
refractive index 1.5790 (estimate)
storage temp. 2-8°C
solubility DMSO: soluble5mg/mL (clear solution; warmed)
form powder
color white to beige
optical activity[α]/D +15 to +25°, c = 1 in methanol
InChIKeyPMGQWSIVQFOFOQ-YKVZVUFRSA-N
CAS DataBase Reference14976-57-9(CAS DataBase Reference)
Safety Information
WGK Germany 3
RTECS UY0704600
HS Code 2933992600
Hazardous Substances Data14976-57-9(Hazardous Substances Data)
ToxicityLD50 in mice, rats (mg/kg): 730, 3550 orally; 43, 82 i.v. (Weimann)
Clemastine fumarate Usage And Synthesis
Chemical PropertiesWhite Solid
OriginatorTavegyl,Sandoz,France,1967
UsesH1 Histamine receptor antagonist. Antihistaminic.
Usesanti-inflammatory
UsesClemastine fumarate is a selective histamine H1 receptor antagonist (Ki = 0.26 nM) that also displays high affinity for muscarinic receptors (Ki = 16 nM). It has also recently been identified as a positive allosteric modulator of P2X7 receptor signaling. Clemastine fumarate has long been used to inhibit histamine-induced bronchoconstriction in asthma and airway hyperresponsive studies.
DefinitionChEBI: The fumaric acid salt of clemastine. An antihistamine with antimuscarinic and moderate sedative properties, it is used for the symptomatic relief of allergic conditions such as rhinitis, urticaria, conjunctivitis and in pruritic (severe itching) skin condi ions.
Manufacturing Process9.9 g of α-methyl-p-chlorobenzhydrol are added to a suspension of 2.3 g of powdered sodamide in 30 cc of benzene. Subsequently 7.4 g of Nmethylpyrrolidyl-(2)-ethyl chloride are added and the solution is heated to the boil at reflux for 20 hours. Then shaking is first effected with water and then 4 times each time with 25 cc of 2 N hydrochloric acid. The acid extracts are made alkaline with potassium hydroxide solution while cooling strongly, and the precipitated oil is extracted with ether. After drying of the ethereal solution over potassium carbonate, the solvent is evaporated and the residue is fractionally distilled in a high vacuum, whereby N-methyl-2-[2'-(α-methyl-pchlorobenzhydryloxy)-ethyl]-pyrrolidine boils over at 154°C/0.02 mm Hg. The base is converted to the fumarate by reaction with fumaric acid.
Brand nameTavist (Novartis).
Therapeutic FunctionAntihistaminic
General DescriptionDextrorotatory clemastine, R,R-2[2[1-(4-chlorophenyl)-1-phenylethoxy]ethyl]-1- methylpyrrolidine hydrogen furnarate (1:1) (Tavist), has two chiral centers, each of which has the (R) absolute configuration. A comparison of the activities of the enantiomers indicates that the asymmetric center close to the terminal side chain nitrogen is of lesser importance to antihistaminic activity.
? This member of the ethanolamine series is characterized by a long duration of action, with an activity that reaches a maximum in 5 to 7 hours and persists for 10 to 12 hours. It is well absorbed when administered orally, and it is excreted primarily in the urine. The side effects are those usually encountered with this series of antihistamines. Clemastine is closely related to chlorphenoxamine, which is used for its central cholinergic-blocking activity. Therefore, it is not surprising that clemastine has significant antimuscarinic activity.
Biological ActivityH 1 -receptor antagonist. Clinically-used antihistamine.
Biochem/physiol ActionsClemastine fumarate is an antihistamine H1-antagonist and anticholinergic that also has antipruritic activity.
Veterinary Drugs and TreatmentsClemastine may be used for symptomatic relief of histamine1-related allergic conditions.
storageStore at RT
Clemastine fumarate Preparation Products And Raw materials
Raw materialsSodium amide-->Fumaric acid
Trinexapac-ethyl Clemastine Ethanol Ferrous fumarate 4-Ethoxyphenol FUMARATE DIETHOXYMETHANE Disodium fumarate Ethoxyquin Ketotifen fumarate Fumaric acid ISOXADIFEN-ETHYL Dimethyl fumarate 2-Ethoxyethanol Diethyl ether Ethyl acetate Bisoprolol fumarate 2-Ethoxyphenol

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