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Identification
- Summary
Clemastine is an antihistamine with sedative and anticholinergic effects used to treat the symptoms of allergic rhinitis.
- Brand Names
- Wal-hist 12 Hr Relief
- Generic Name
- Clemastine
- DrugBank Accession Number
- DB00283
- Background
An ethanolamine-derivative, first generation histamine H1 antagonist used in hay fever, rhinitis, allergic skin conditions, and pruritus. It causes drowsiness.
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Clemastine (DB00283)
- Weight
- Average: 343.89
Monoisotopic: 343.170292166 - Chemical Formula
- C21H26ClNO
- Synonyms
- (+)-(2R)-2-(2-(((R)-p-chloro-α-methyl-α-phenylbenzyl)oxy)ethyl)-1-methylpyrrolidine
- (+)-(2R)-2-[2-[[(R)-p-chloro-α-methyl-α-phenylbenzyl]oxy]ethyl]-1-methylpyrrolidine
- Clemastina
- Clemastine
- Clemastinum
- External IDs
- HS-592
Pharmacology
- 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.
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Symptomatic treatment of Allergic rhinitis •••••••••••• Treatment of Allergic rhinitis •••••••••••• ••••• Used in combination to manage Allergic rhinitis Combination Product in combination with: Phenylpropanolamine (DB00397) •••••••••••• Symptomatic treatment of Angioedema •••••••••••• Symptomatic treatment of Common cold ••• ••• - Contraindications & Blackbox Warnings
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Clemastine is an antihistamine that also induces anticholinergic and sedative 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.
- Mechanism 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.
Target Actions Organism AHistamine H1 receptor antagonistHumans - Absorption
Rapidly absorbed from the gastrointestinal tract.
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
Antihistamines appear to be metabolized in the liver chiefly via mono- and didemethylation and glucuronide conjugation.
- Route of elimination
Urinary excretion is the major mode of elimination.
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
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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.
- Pathways
Pathway Category Clemastine H1-Antihistamine Action Drug action - Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of CNS depression can be increased when Clemastine is combined with 1,2-Benzodiazepine. Acebutolol The metabolism of Acebutolol can be decreased when combined with Clemastine. Acetaminophen The metabolism of Acetaminophen can be decreased when combined with Clemastine. Acetazolamide The risk or severity of CNS depression can be increased when Clemastine is combined with Acetazolamide. Acetophenazine The risk or severity of CNS depression can be increased when Clemastine is combined with Acetophenazine. - Food Interactions
- Avoid alcohol.
- Take with food.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Clemastine fumarate 19259EGQ3D 14976-57-9 PMGQWSIVQFOFOQ-YKVZVUFRSA-N - Product Images
- International/Other Brands
- Agasten (Novartis (Brazil)) / Allerhist-1 / Tavegil (Novartis) / Tavegyl (Novartis) / Tavist (Novartis) / Tavist-1 (Novartis)
- Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Clemastine Fumarate Tablet 2.68 mg/1 Oral Teva Pharmaceuticals USA, Inc. 1992-04-01 Not applicable US 
Clemastine Fumarate Tablet 2.68 mg/1 Oral Sandoz S.P.A. 1993-10-31 2016-10-31 US Clemastine Fumarate Tablet 2.68 mg/1 Oral Northwind Pharmaceuticals, LLC 2014-04-28 2014-06-25 US Clemastine Fumarate Syrup 0.67 mg/5mL Oral Chartwell Rx, Llc 1997-12-17 Not applicable US Clemastine Fumarate Syrup 0.67 mg/5mL Oral Lannett Company, Inc. 1997-12-17 Not applicable US - Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Allergy Relief Tablet 1.34 mg/1 Oral CVS Health 1996-08-28 2014-03-21 US Clemastine Fumarate Tablet 1.34 mg/1 Oral Carilion Materials Management 1993-10-31 Not applicable US Clemastine Fumarate Tablet 1.34 mg/1 Oral Physicians Total Care, Inc. 2008-06-27 Not applicable US Clemastine Fumarate Tablet 1.34 mg/1 Oral Sandoz S.P.A. 1993-10-31 2016-10-31 US Dayhist Allergy Tablet 1.34 mg/1 Oral H E B 1995-08-30 2016-12-16 US - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Tavist-D Tablets Clemastine fumarate (1 mg) + Phenylpropanolamine hydrochloride (75 mg) Tablet, extended release Oral Novartis 1992-12-31 2001-04-24 Canada 
Categories
- ATC Codes
- D04AA14 — Clemastine
- D04AA — Antihistamines for topical use
- D04A — ANTIPRURITICS, INCL. ANTIHISTAMINES, ANESTHETICS, ETC.
- D04 — ANTIPRURITICS, INCL. ANTIHISTAMINES, ANESTHETICS, ETC.
- D — DERMATOLOGICALS
- R06AA — Aminoalkyl ethers
- R06A — ANTIHISTAMINES FOR SYSTEMIC USE
- R06 — ANTIHISTAMINES FOR SYSTEMIC USE
- R — RESPIRATORY SYSTEM
- Drug Categories
- Aminoalkyl Ethers
- Anti-Allergic Agents
- Antihistamines for Systemic Use
- Antihistamines for Topical Use
- Antipruritics
- Antipruritics, Incl. Antihistamines, Anesthetics, Etc.
- Central Nervous System Depressants
- Cytochrome P-450 CYP2D6 Inhibitors
- Cytochrome P-450 CYP2D6 Inhibitors (strength unknown)
- Cytochrome P-450 Enzyme Inhibitors
- Dermatologicals
- Highest Risk QTc-Prolonging Agents
- Histamine Agents
- Histamine Antagonists
- Histamine H1 Antagonists
- Neurotransmitter Agents
- Pyrrolidines
- QTc Prolonging Agents
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as diphenylmethanes. These are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Diphenylmethanes
- Direct Parent
- Diphenylmethanes
- Alternative Parents
- Benzylethers / Chlorobenzenes / N-alkylpyrrolidines / Aryl chlorides / Trialkylamines / Dialkyl ethers / Azacyclic compounds / Organopnictogen compounds / Organochlorides / Hydrocarbon derivatives
- Substituents
- Amine / Aromatic heteromonocyclic compound / Aryl chloride / Aryl halide / Azacycle / Benzylether / Chlorobenzene / Dialkyl ether / Diphenylmethane / Ether
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- monochlorobenzenes, N-alkylpyrrolidine (CHEBI:3738)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 95QN29S1ID
- CAS number
- 15686-51-8
- InChI Key
- YNNUSGIPVFPVBX-NHCUHLMSSA-N
- InChI
- InChI=1S/C21H26ClNO/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/h3-5,7-8,10-13,20H,6,9,14-16H2,1-2H3/t20-,21-/m1/s1
- IUPAC Name
- (2R)-2-{2-[1-(4-chlorophenyl)-1-phenylethoxy]ethyl}-1-methylpyrrolidine
- SMILES
- CN1CCC[C@@H]1CCO[C@](C)(C1=CC=CC=C1)C1=CC=C(Cl)C=C1
References
- Synthesis Reference
British Patent 942,152; November 20,1963; assigned to Sandoz Ltd.
- General References
- 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. [Article]
- Schran 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. [Article]
- External Links
- Human Metabolome Database
- HMDB0014428
- KEGG Drug
- D03535
- KEGG Compound
- C06913
- PubChem Compound
- 26987
- PubChem Substance
- 46506492
- ChemSpider
- 25129
- BindingDB
- 94606
- 2578
- ChEBI
- 3738
- ChEMBL
- CHEMBL1626
- ZINC
- ZINC000000402830
- Therapeutic Targets Database
- DAP000322
- PharmGKB
- PA164776997
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Clemastine
- MSDS
- Download (74.2 KB)
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample dataNot Available Completed Not Available Solid Tumors 1 somestatus stop reason just information to hide Not Available Completed Prevention Safety and Efficacy 1 somestatus stop reason just information to hide 3 Recruiting Treatment Children / Neurodevelopmental Delay / Williams Syndrome 1 somestatus stop reason just information to hide 3 Recruiting Treatment Internuclear Ophthalmoplegia / Multiple Sclerosis 1 somestatus stop reason just information to hide 3 Recruiting Treatment Williams Syndrome 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Actavis mid atlantic llc
- Novex pharma
- Silarx pharmaceuticals inc
- Teva pharmaceuticals usa inc
- Teva pharmaceuticals usa
- Wockhardt eu operations (swiss) ag
- Novartis pharmaceuticals corp
- Perrigo co
- Sandoz inc
- Packagers
- Apotex Inc.
- Boca Pharmacal
- CVS Pharmacy
- Dispensing Solutions
- H.J. Harkins Co. Inc.
- Kroger Co.
- Major Pharmaceuticals
- Murfreesboro Pharmaceutical Nursing Supply
- Novartis AG
- Novex Pharma
- Nucare Pharmaceuticals Inc.
- Perrigo Co.
- Pharmaceutical Utilization Management Program VA Inc.
- Pharmedix
- Physicians Total Care Inc.
- Prescript Pharmaceuticals
- Professional Co.
- Qualitest
- Sandoz
- Silarx Pharmaceuticals
- Teva Pharmaceutical Industries Ltd.
- United Research Laboratories Inc.
- Wockhardt Ltd.
- Dosage Forms
Form Route Strength Syrup Oral 0.5 mg/1mL Syrup Oral 0.5 mg/5mL Syrup Oral 0.67 mg/5mL Tablet Oral 1.34 mg/1 Tablet Oral 2.68 mg/1 Solution Intramuscular; Intravenous 2 mg Gel Topical Syrup Oral Tablet Oral Syrup Oral 0.5 mg / 5 mL Tablet Oral 1 mg Tablet, extended release Oral - Prices
Unit description Cost Unit Clemastine fumarate powder 255.0USD g Clemastine Fumarate 0.67 mg/5ml Syrup 120ml Bottle 22.2USD bottle Clemastine Fumarate 2.68 mg tablet 0.9USD tablet Clemastine fum 2.68 mg tablet 0.86USD tablet Tavist nd 10 mg tablet 0.74USD tablet Clemastine fum 1.34 mg tablet 0.58USD tablet Tavist-1 1.34 mg tablet 0.5USD tablet Clemastine Fumarate 1.34 mg tablet 0.34USD tablet Dayhist tablet 0.31USD tablet CVS Pharmacy dayhist allergy tablet 0.28USD tablet Dayhist-1 1.34 mg tablet 0.25USD tablet Tavist max-str sinus caplet 0.17USD caplet DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 178 °C (hydrogen fumarate formulation) Not Available water solubility Soluble (hydrogen fumarate formulation) Not Available logP 5.2 Not Available - Predicted Properties
Property Value Source Water Solubility 0.000405 mg/mL ALOGPS logP 5.29 ALOGPS logP 4.92 Chemaxon logS -5.9 ALOGPS pKa (Strongest Basic) 9.55 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 12.47 Å2 Chemaxon Rotatable Bond Count 6 Chemaxon Refractivity 101.65 m3·mol-1 Chemaxon Polarizability 39.06 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9942 Blood Brain Barrier + 0.9918 Caco-2 permeable + 0.6652 P-glycoprotein substrate Substrate 0.6659 P-glycoprotein inhibitor I Inhibitor 0.808 P-glycoprotein inhibitor II Inhibitor 0.8388 Renal organic cation transporter Inhibitor 0.8471 CYP450 2C9 substrate Non-substrate 0.819 CYP450 2D6 substrate Non-substrate 0.9116 CYP450 3A4 substrate Substrate 0.7176 CYP450 1A2 substrate Non-inhibitor 0.9045 CYP450 2C9 inhibitor Non-inhibitor 0.907 CYP450 2D6 inhibitor Inhibitor 0.8931 CYP450 2C19 inhibitor Inhibitor 0.8993 CYP450 3A4 inhibitor Inhibitor 0.7028 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.5 Ames test Non AMES toxic 0.7454 Carcinogenicity Non-carcinogens 0.8549 Biodegradation Not ready biodegradable 0.9972 Rat acute toxicity 2.9450 LD50, mol/kg Not applicable hERG inhibition (predictor I) Strong inhibitor 0.5986 hERG inhibition (predictor II) Inhibitor 0.8702
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-0159-9381000000-2be9b3484b69dbb1ec63 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-001l-1915000000-e47fd592bf1617d681f6 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0006-3197000000-7c3770d8fb13d8cd5bb3 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0006-7901000000-d5c2eef4c56ee9ad9cf2 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-001i-4931000000-00255db249ba328f7dad Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0gc9-3920000000-2f3d62f3e87a8448c45a Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-000i-1900000000-f3705f9d64e00d2015a8 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 177.003609 predictedDarkChem Lite v0.1.0 [M-H]- 177.78992 predictedDeepCCS 1.0 (2019) [M+H]+ 177.232009 predictedDarkChem Lite v0.1.0 [M+H]+ 180.19118 predictedDeepCCS 1.0 (2019) [M+Na]+ 177.162709 predictedDarkChem Lite v0.1.0 [M+Na]+ 187.35234 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- G-protein-coupled receptor for histamine, a biogenic amine that functions as an immune modulator and a neurotransmitter (PubMed:33828102, PubMed:8280179). Through the H1 receptor, histamine mediates the contraction of smooth muscles and increases capillary permeability due to contraction of terminal venules. Also mediates neurotransmission in the central nervous system and thereby regulates circadian rhythms, emotional and locomotor activities as well as cognitive functions (By similarity)
- Specific Function
- G protein-coupled serotonin receptor activity
- Gene Name
- HRH1
- Uniprot ID
- P35367
- Uniprot Name
- Histamine H1 receptor
- Molecular Weight
- 55783.61 Da
References
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
- Taniguchi K, Urakami M, Takanaka K: [Effects of antiallergic agents on polymorphonuclear leukocytes. The inhibition of arachidonic acid release and superoxide production]. Nihon Yakurigaku Zasshi. 1987 Aug;90(2):97-103. [Article]
- Hallberg T, Dohlsten M, Baldetorp B: Demonstration of histamine receptors on human platelets by flow cytometry. Scand J Haematol. 1984 Feb;32(2):113-8. [Article]
- Dorsch W, Hintschich C, Neuhauser J, Weber J: Sequential histamine inhalations cause increased bronchial histamine reactivity in guinea pigs: role of platelets, thromboxanes and prostacyclin. Naunyn Schmiedebergs Arch Pharmacol. 1984 Sep;327(2):148-55. [Article]
- Taniguchi K, Masuda Y, Takanaka K: Inhibitory effects of histamine H1 receptor blocking drugs on metabolic activations of neutrophils. J Pharmacobiodyn. 1991 Feb;14(2):87-93. [Article]
- Oishi R, Shishido S, Yamori M, Saeki K: Comparison of the effects of eleven histamine H1-receptor antagonists on monoamine turnover in the mouse brain. Naunyn Schmiedebergs Arch Pharmacol. 1994 Feb;349(2):140-4. [Article]
- Thomas RH, Browne PD, Kirby JD: The influence of ranitidine, alone and in combination with clemastine, on histamine-mediated cutaneous weal and flare reactions in human skin. Br J Clin Pharmacol. 1985 Oct;20(4):377-82. [Article]
- Thomson NC, Kerr JW: Effect of inhaled H1 and H2 receptor antagonist in normal and asthmatic subjects. Thorax. 1980 Jun;35(6):428-34. [Article]
- 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. [Article]
- Schran 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. [Article]
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of fatty acids, steroids and retinoids (PubMed:18698000, PubMed:19965576, PubMed:20972997, PubMed:21289075, PubMed:21576599). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:18698000, PubMed:19965576, PubMed:20972997, PubMed:21289075, PubMed:21576599). Catalyzes the epoxidation of double bonds of polyunsaturated fatty acids (PUFA) (PubMed:19965576, PubMed:20972997). Metabolizes endocannabinoid arachidonoylethanolamide (anandamide) to 20-hydroxyeicosatetraenoic acid ethanolamide (20-HETE-EA) and 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid ethanolamides (EpETrE-EAs), potentially modulating endocannabinoid system signaling (PubMed:18698000, PubMed:21289075). Catalyzes the hydroxylation of carbon-hydrogen bonds. Metabolizes cholesterol toward 25-hydroxycholesterol, a physiological regulator of cellular cholesterol homeostasis (PubMed:21576599). Catalyzes the oxidative transformations of all-trans retinol to all-trans retinal, a precursor for the active form all-trans-retinoic acid (PubMed:10681376). Also involved in the oxidative metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants
- Specific Function
- anandamide 11,12 epoxidase activity
- Gene Name
- CYP2D6
- Uniprot ID
- P10635
- Uniprot Name
- Cytochrome P450 2D6
- Molecular Weight
- 55768.94 Da
References
- Flockhart Table of Drug Interactions [Link]
Drug created at June 13, 2005 13:24 / Updated at October 30, 2024 22:59