Basic information
- CAS
14976-57-9- Standard SMILES
CN1CCC[C@@H]1CCO[C@](C)(c1ccccc1)c1ccc(Cl)cc1.O=C(O)/C=C/C(=O)O- InChIKey
PMGQWSIVQFOFOQ-YKVZVUFRSA-N- Molecular formula
- C25H30ClNO5
- Average molar mass
- 460 g/mol
- Monoisotopic mass
- 459.1812508
Overview
Clemastine fumarate is 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 conditions. It has a role as a H1-receptor antagonist, a muscarinic antagonist, an anti-allergic agent and an antipruritic drug. It contains a clemastine.
Names & identifiers
- Preferred name
- Clemastine Fumarate
- IUPAC
- (E)-but-2-enedioic acid;(2R)-2-[2-[(1R)-1-(4-chlorophenyl)-1-phenylethoxy]ethyl]-1-methylpyrrolidine
- English name
- Clemastine fumarate
- Molecular formula
- C21H26ClNO.C4H4O4
- Molecular weight
- 459.96
Names & synonyms
CLEMASTINE FUMARATE14976-57-9AgastenTavistMecloprodineAloginanXolaminClemastine hydrogen fumarateAlphaminAnhistanClemanilFuluminol
Show more names
hs592Alagyltavegiltavegyltrabest
InbestanKinotominLacretinMarsthineMasletineLecasolPiloralReconin
Database identifiers
- CAS
14976-57-9、15686-51-8- PubChem CID
- 5281069
- DTXSID
DTXSID6047785- ChEMBL
CHEMBL1200795- ChEBI
CHEBI:3739- UNII
- 19259EGQ3D
- EC Number
- 239-055-2
Properties
Computed structural properties
- Topological polar surface area
- 87.1 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 8
- Heavy atoms
- 32
- Formal charge
- 0
- Complexity
- 495
Experimental & physicochemical properties
OdorOdorless
Color/FormColorless to faintly yellow crystalline powder
SolubilityVery slightly soluble in water and sparingly soluble in alcohol.
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Boiling Point154 °C at 0.02 mm Hg
Melting Point177-178 °C
Other Experimental Properties154 °C at 0.02 mm Hg (free base)
Physicochemical properties
- Melting point
- 158 · 158-162°C
- alpha
- 21 · D21 +16.9° (methanol)
- Boiling point
- 154 °C · 154°C (rough estimate)
- Density
- 1.0247 · 1.0247 (rough estimate)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 66.7% (12 of 18) of all reports.
Warning
H400 (22.2%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]
P273, P391, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 18 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
FDA Requirements
Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392).
The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed drug products, incl clemastine fumarate, approved on the basis of safety and effectiveness by FDA under sections 505 and 507 of the Federal Food, Drug, and Cosmetic Act. /From the Prescription Drug Product List/
Hazard Classes and CategoriesAquatic Acute 1 (22.2%)
Toxicology
Body BurdenFollowing oral administration of 2.68 mg of clemastine fumarate daily for 3 days in one nursing woman, a milk clemastine concentration of about 5-10 ug/ml occurred 20 hours after the last dose of the drug.
Milk ConcentrationsFollowing oral administration of 2.68 mg of clemastine fumarate daily for 3 days in one nursing woman, a milk clemastine concentration of about 5-10 ug/ml occurred 20 hours after the last dose of the drug.
Chemistry & industry
Pharmacology
Mechanism of Action
Inhibitory effects of various histamine receptor-blocking agents including antiallergic agents on metabolic activations of neutrophils were examined by measuring leukotrienes (C4, D4 and E4) formation, arachidonic acid release and superoxide generation. The stimulation of neutrophils by calcium ionophore causes the production of leukotrienes concomitantly with the release of arachidonic acid from the cells and these were effectively diminished with a variety of antihistaminic agents. Almost all the histamine H1 receptor-blocking drugs studied here showed as inhibitors of the metabolic activations of neutrophils, although the degree was dependent on the drug concentrations. The order of potency of the inhibitory effects on the arachidonic acid release were: homochlorcyclizine, clemastine, and azelastine (IC50 < 20 microM) greater than oxatomide (IC50 < 60 microM) and diphenylpyraline greater than triprolidine, meclizine, diphenhydramine (IC50 > 100 microM). The superoxide generation from neutrophils activated by phorbol 12-myristate 13-acetate was also effectively inhibited by these agents, but generally lower concentrations were required to obtain the same degrees of effects. These results indicated that some of the histamine H1 receptor-blocking drugs, such as clemastine and homochlorcyclizine, may act as inhibitors of formation of leukotrienes at the locus of inflammation.
Metabolism/Metabolites
The exact metabolic fate of clemastine is not clearly established, but the drug appears to be extensively metabolized. Clemastine and its metabolites are eliminated principally in urine.
Time to peak concentration: 2-4 hr
MeSH Pharmacological Classification
Agents, usually topical, that relieve itching (pruritus).
Drugs that selectively bind to but do not activate histamine H1 receptors, thereby blocking the actions of endogenous histamine. Included here are the classical antihistaminics that antagonize or prevent the action of histamine mainly in immediate hypersensitivity. They act in the bronchi, capillaries, and some other smooth muscles, and are used to prevent or allay motion sickness, seasonal rhinitis, and allergic dermatitis and to induce somnolence. The effects of blocking central nervous system H1 receptors are not as well understood.
Agents that are used to treat allergic reactions. Most of these drugs act by preventing the release of inflammatory mediators or inhibiting the actions of released mediators on their target cells. (From AMA Drug Evaluations Annual, 1994, p475)
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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