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    Chemistry

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    Also known as: 14976-57-9, Tavist, Agasten, Clemastine hydrogen fumarate, Meclastine fumarate, Tavegil
    Molecular Formula
    C25H30ClNO5
    Molecular Weight
    460.0  g/mol
    InChI Key
    PMGQWSIVQFOFOQ-YKVZVUFRSA-N
    FDA UNII
    19259EGQ3D
    Clemastine
    A histamine H1 antagonist used as the hydrogen fumarate in hay fever, rhinitis, allergic skin conditions, and pruritus. It causes drowsiness.
    1 2D Structure

    Clemastine

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (E)-but-2-enedioic acid;(2R)-2-[2-[(1R)-1-(4-chlorophenyl)-1-phenylethoxy]ethyl]-1-methylpyrrolidine
    2.1.2 InChI
    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
    2.1.3 InChI Key
    PMGQWSIVQFOFOQ-YKVZVUFRSA-N
    2.1.4 Canonical SMILES
    CC(C1=CC=CC=C1)(C2=CC=C(C=C2)Cl)OCCC3CCCN3C.C(=CC(=O)O)C(=O)O
    2.1.5 Isomeric SMILES
    C[C@@](C1=CC=CC=C1)(C2=CC=C(C=C2)Cl)OCC[C@H]3CCCN3C.C(=C/C(=O)O)\C(=O)O
    2.2 Other Identifiers
    2.2.1 UNII
    19259EGQ3D
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 2-(2-(1-(4-chlorophenyl)-1-phenylethoxy)ethyl)-1-methylpyrrolidine

    2. Clemastine

    3. Hs 592

    4. Hs-592

    5. Hs592

    6. Meclastine

    7. Mecloprodin

    8. Tavegyl

    9. Tavist

    2.3.2 Depositor-Supplied Synonyms

    1. 14976-57-9

    2. Tavist

    3. Agasten

    4. Clemastine Hydrogen Fumarate

    5. Meclastine Fumarate

    6. Tavegil

    7. Clemastine (fumarate)

    8. (r)-2-(2-((r)-1-(4-chlorophenyl)-1-phenylethoxy)ethyl)-1-methylpyrrolidine Fumarate

    9. Chebi:3739

    10. Mecloprodine

    11. Aloginan

    12. Xolamin

    13. 19259egq3d

    14. (+)-(2r)-2-(2-(((r)-p-chloro-alpha-methyl-alpha-phenylbenzyl)oxy)ethyl)-1-methylpyrrolidine Fumarate (1:1)

    15. 14976-57-9 (fumarate)

    16. Alphamin

    17. Anhistan

    18. Clemanil

    19. Fuluminol

    20. Inbestan

    21. Kinotomin

    22. Lacretin

    23. Lecasol

    24. Maikohis

    25. Marsthine

    26. Masletine

    27. Piloral

    28. Reconin

    29. Tavegyl

    30. Trabest

    31. Mallermin-f

    32. Telgin-g

    33. Dsstox_cid_27765

    34. Dsstox_rid_82542

    35. Dsstox_gsid_47785

    36. Tavist-1

    37. Pyrrolidine, 2-(2-(1-(4-chlorophenyl)-1-phenylethoxy)ethyl)-1-methyl-, (r-(r*,r*))-, (e)-2-butenedioate (1:1)

    38. Meclastine Hydrogen Fumarate

    39. (2e)-but-2-enedioic Acid; (2r)-2-{2-[(1r)-1-(4-chlorophenyl)-1-phenylethoxy]ethyl}-1-methylpyrrolidine

    40. (e)-but-2-enedioic Acid;(2r)-2-[2-[(1r)-1-(4-chlorophenyl)-1-phenylethoxy]ethyl]-1-methylpyrrolidine

    41. Hsdb 6507

    42. Topcare Dayhist Allergy

    43. Ncgc00016710-01

    44. Contac 12 Hour Allergy

    45. Einecs 239-055-2

    46. Cas-14976-57-9

    47. Clemastine For System Suitability

    48. Unii-19259egq3d

    49. (r)-2-[2-[(r)-1-(4-chlorophenyl)-1-phenylethoxy]ethyl]-1-methylpyrrolidine Fumarate

    50. Prestwick_680

    51. Meclastine (fumarate)

    52. Clemastinefumarate,(s)

    53. Clemastine Fumarate [usan:usp:ban:jan]

    54. Hs-592 (fumarate)

    55. (+)-2-(2-((p-chloro-alpha-methyl-alpha-phenylbenzyl)oxy)ethyl)-1-methyl Pyrrolidine Fumarate

    56. Schembl33403

    57. Schembl41468

    58. Spectrum1500191

    59. Chembl1200795

    60. Dtxsid6047785

    61. Hms500o07

    62. Hy-b0298a

    63. Clemastine Fumarate [jan]

    64. Clemastine Fumarate [hsdb]

    65. Clemastine Fumarate [usan]

    66. Hms1568n14

    67. Hms1920o13

    68. Hms2091e20

    69. Hms2095n14

    70. Hms3267l12

    71. Hms3412b19

    72. Hms3676b19

    73. Hms3712n14

    74. Hms3884k12

    75. Pharmakon1600-01500191

    76. Clemastine Fumarate [vandf]

    77. Bcp27945

    78. Clemastine Fumarate [mart.]

    79. Tox21_110574

    80. Ccg-40028

    81. Clemastine Fumarate [usp-rs]

    82. Clemastine Fumarate [who-dd]

    83. Mfcd00137486

    84. Nsc756685

    85. S1847

    86. Akos015896237

    87. Akos037643271

    88. Tox21_110574_1

    89. Ac-1338

    90. Clemastine Fumarate [orange Book]

    91. Clemastine Hydrogen Fumarate [mi]

    92. Ncgc00016710-05

    93. Ncgc00180903-01

    94. Ncgc00180903-02

    95. (r-(r*,r*))-2-(2-(1-(p-chlorophenyl)-1-phenylethoxy)ethyl)-1-methylpyrrolidinium Hydrogen Fumarate

    96. As-12093

    97. Bc164321

    98. Clemastine Fumarate [ep Monograph]

    99. Pyrrolidine, 2-(2-((p-chloro-alpha-methyl-alpha-phenylbenzyl)oxy)ethyl)-1-methyl-, (+)-, Fumarate (1:1)

    100. Clemastine Fumarate [usp Monograph]

    101. Clemastine Fumarate Salt, >=98% (hplc)

    102. Sw196835-3

    103. Tavist-d Component Clemastine Fumarate

    104. H10994

    105. Clemastine Fumarate Component Of Tavist-d

    106. 976c579

    107. Sr-05000001590

    108. Sr-05000001590-1

    109. Q27106180

    110. Clemastine Fumarate, European Pharmacopoeia (ep) Reference Standard

    111. Clemastine Fumarate, United States Pharmacopeia (usp) Reference Standard

    112. (2r)-2-[2-[(1r)-1-(4-chlorophenylethoxy]ethyl]-1-methyl-2-pyrrolidine Fumarate

    113. Clemastine For System Suitability, European Pharmacopoeia (ep) Reference Standard

    114. (+)-(2r)-2-(2-(((r)-p-chloro-.alpha.-methyl-.alpha.-phenylbenzyl)oxy)ethyl)-1-methylpyrrolidine Fumarate (1:1)

    115. (2r)-2-[2-[(1r)-1-(4-chlorophenyl)-1-phenylethoxy]ethyl]-1-methylpyrrolidin-1-ium;(e)-4-hydroxy-4-oxobut-2-enoate

    116. (2r)-2-{2-[(1r)-1-(4-chlorophenyl)-1-phenylethoxy]ethyl}-1-methylpyrrolidine (2e)-but-2-enedioate

    117. (2r)-2-{2-[(1r)-1-(4-chlorophenyl)-1-phenylethoxy]ethyl}-1-methylpyrrolidinium (2e)-3-carboxyprop-2-enoate

    118. Pyrrolidine,2-[2-[(1r)-1-(4-chlorophenyl)-1-phenylethoxy]ethyl]-1-methyl-, (2r)-,(2e)-2-butenedioate (1:1)

    2.4 Create Date
    2005-06-24
    3 Chemical and Physical Properties
    Molecular Weight 460.0 g/mol
    Molecular Formula C25H30ClNO5
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count6
    Rotatable Bond Count8
    Exact Mass459.1812508 g/mol
    Monoisotopic Mass459.1812508 g/mol
    Topological Polar Surface Area87.1 Ų
    Heavy Atom Count32
    Formal Charge0
    Complexity495
    Isotope Atom Count0
    Defined Atom Stereocenter Count2
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count1
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count2
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 4  
    Drug NameClemastine fumarate
    Active IngredientClemastine fumarate
    Dosage FormTablet; Syrup
    RouteOral
    Strength1.34mg; 2.68mg; eq 0.5mg base/5ml
    Market StatusOver the Counter; Prescription
    CompanyWockhardt; Teva; Perrigo; Sandoz

    2 of 4  
    Drug NameTavist-1
    Drug LabelClemastine belongs to the benzhydryl ether group of antihistaminic compounds. The chemical name is (+)-(2R)-2-[2-[[(R)-p-Chloro--methyl--phenylbenzyl]-oxy]ethyl]-1-methylpyrrolidine fumarate (1:1).C21H26C1NO.C4H4O4 M.W. 459.97Each tablet for oral...
    Active IngredientClemastine fumarate
    Dosage FormTablet
    RouteOral
    Strength1.34mg
    Market StatusOver the Counter
    CompanyNovartis

    3 of 4  
    Drug NameClemastine fumarate
    Active IngredientClemastine fumarate
    Dosage FormTablet; Syrup
    RouteOral
    Strength1.34mg; 2.68mg; eq 0.5mg base/5ml
    Market StatusOver the Counter; Prescription
    CompanyWockhardt; Teva; Perrigo; Sandoz

    4 of 4  
    Drug NameTavist-1
    Drug LabelClemastine belongs to the benzhydryl ether group of antihistaminic compounds. The chemical name is (+)-(2R)-2-[2-[[(R)-p-Chloro--methyl--phenylbenzyl]-oxy]ethyl]-1-methylpyrrolidine fumarate (1:1).C21H26C1NO.C4H4O4 M.W. 459.97Each tablet for oral...
    Active IngredientClemastine fumarate
    Dosage FormTablet
    RouteOral
    Strength1.34mg
    Market StatusOver the Counter
    CompanyNovartis

    4.2 Therapeutic Uses

    For the symptomatic treatment of allergic rhinitis in adults and children 12 years of age and older ...

    McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 92. Bethesda, MD: American Society of Hospital Pharmacists, Inc., 1992 (Plus Supplements 1992)., p. 15

    For the symptomatic treatment of mild allergic urticaria and angioedema in adults and children 12 years of age and older ...

    McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 92. Bethesda, MD: American Society of Hospital Pharmacists, Inc., 1992 (Plus Supplements 1992)., p. 15

    This multicenter, double blind, randomized parallel group study compared 3 wk treatment with either loratadine (Clarityn) 10 mg once daily, or clemastine (Tavegyl) 1 mg twice daily, and placebo in outpatients with active perennial allergic rhinitis. 155 patients were evaluated for efficacy and safety. Grading of four nasal and three non-nasal symptoms, rhinoscopy signs, and therapeutic response was performed on treatment days 6, 13, and 20. Patients recorded daily symptoms and possible adverse experiences in a diary, also indicating when symptoms of active rhinitis were relieved. Loratadine and clemastine were statistically significantly superior to placebo throughout the study (p < 0.05), based on assessment of patients' nasal and eye symptoms, patients' diary scores, rhinoscopy signs of symptoms, and onset of relief. The loratadine group showed a statistically significantly (p < 0.05) faster onset of relief of symptoms compared with the group treated with clemastine. Concerning nasal stuffiness, loratadine was significantly (p < 0.05) superior to clemastine after 1 week's treatment. Reports of adverse reactions showed that significantly (p < 0.05) more patients complained of sedation in the clemastine than in the loratadine group. Regarding other adverse experiences and laboratory tests, the three treatment groups were statistically comparable (p < 0.05). The study showed that compared with placebo both loratadine and clemastine were effective in relieving nasal and eye symptoms in patients with perennial allergic rhinitis. Loratadine was safe and well tolerated and was significantly less sedative than clemastine; loratadine may therefore possess an advantage in clinical use in the treatment of perennial allergic rhinitis.

    PMID:2143361 Frolund L et al; Allergy 45 (4): 254-61 (1990)

    The effects of cromolyn sodium (sodium cromoglycate), clemastine and ketotifen administered to the nasal mucosa of seasonal and perennial allergic rhinitis patients 30 min before provocation with histamine and allergen were compared in a randomized, double blind, placebo controlled study. Clemastine and cromolyn sodium, but not ketotifen, significantly inhibited the nasal response to increasing concentrations of histamine. None of the drugs administered in the concentrations used significantly inhibited the nasal response to allergen.

    PMID:3117084 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1386248 Corrado OJ et al; Br J Clin Pharmacol 24 (Sep): 283-92 (1987)

    4.3 Drug Warning

    Drugs contraindicated during lactation include ... clemastine.

    Ellenhorn, M.J. and D.G. Barceloux. Medical Toxicology - Diagnosis and Treatment of Human Poisoning. New York, NY: Elsevier Science Publishing Co., Inc. 1988., p. 113

    There are no adequate and controlled studies to date using clemastine fumarate alone or in fixed combination with phenylpropanolamine in pregnant women, and the drug should be used during pregnancy only when clearly needed.

    McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 92. Bethesda, MD: American Society of Hospital Pharmacists, Inc., 1992 (Plus Supplements 1992)., p. 15

    Because of the potential for serious adverse reactions to clemastine in nursing infants, a decision should be made whether to discontinue nursing or the drug, taking into account the importance of the drug to the woman.

    McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 92. Bethesda, MD: American Society of Hospital Pharmacists, Inc., 1992 (Plus Supplements 1992)., p. 15

    Drugs that have been associated with Significant Effects on some Nursing Infants and should be given to Nursing Mothers with Caution: Clemastine: Drowsiness, irritability, refusal to feed, high-pitched cry, neck stiffness (1 case). /from Table 5/

    Report of the American Academy of Pediatrics Committee on Drugs in Pediatrics 93 (1): 139 (1994)

    5 Pharmacology and Biochemistry
    5.1 MeSH Pharmacological Classification

    Antipruritics

    Agents, usually topical, that relieve itching (pruritus). (See all compounds classified as Antipruritics.)

    Anti-Allergic Agents

    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) (See all compounds classified as Anti-Allergic Agents.)

    Histamine H1 Antagonists

    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. (See all compounds classified as Histamine H1 Antagonists.)

    5.2 Absorption, Distribution and Excretion

    In 12 healthy subjects given clemastine fumarate by mouth peak plasma concentrations occurred after 3 to 5 hr. After intravenous injection in 3 subjects a rapid decline in plasma concentration during the first 30 minutes occurred followed by a slow rise to peak concentration 2 to 3 hours after administraton. In 5 subjects given clemastine fumarate the ability to inhibit histamine flares correlated well with plasma concentation.

    Reynolds, J.E.F., Prasad, A.B. (eds.) Martindale-The Extra Pharmacopoeia. 28th ed. London: The Pharmaceutical Press, 1982., p. 1307

    Clemastine fumarate is rapidly and almost completely absorbed from the GI tract. Peak plasma concentrations of the drug are attained within 2-5 hours after a single oral dose. Following oral administration of clemastine fumarate, the antihistaminic effect of the drug (as measured by suppression of the wheal response induced by intradermal injection of histamine) is maximal within 5-7 hours and persists for 10-12 and, in some individuals, up to 24 hours.

    McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 92. Bethesda, MD: American Society of Hospital Pharmacists, Inc., 1992 (Plus Supplements 1992)., p. 14

    Distribution of clemastine into human body fluids and tissues has not been fully characterized, but the drug has been shown to distribute into milk. Following 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 and was about 25-50% of the stimultaneous maternal plasma drug concentration; clemastine was undetectable in milk 6 days after discontuance of the drug.

    McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 92. Bethesda, MD: American Society of Hospital Pharmacists, Inc., 1992 (Plus Supplements 1992)., p. 14

    Clemastine and its metabolites are eliminated principally in urine.

    McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 92. Bethesda, MD: American Society of Hospital Pharmacists, Inc., 1992 (Plus Supplements 1992)., p. 14

    5.3 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.

    McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 92. Bethesda, MD: American Society of Hospital Pharmacists, Inc., 1992 (Plus Supplements 1992)., p. 14

    Time to peak concentration: 2-4 hr

    US Pharmacopeial Convention; US Pharmacopeia Dispensing Information (USP DI); Drug Information for the Health Care Professional 12th ed, V.I p.403 (1992)

    5.4 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.

    PMID:1678430 Taniguchi K et al; J Pharmacobiodyn 14 (2): 87-93 (1991)

    API Reference Price

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    18-Aug-2022
    04-Sep-2024
    KGS
    overview
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    Average Price (USD/KGS)

    Number of Transactions

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    Quantity (KGS) & Unit rate (USD/KGS) over time

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    (USD/KGS)    		 Number of Transactions

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