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    Also known as: 87848-99-5, Semprex, Acrivastin, Acrivastinum, Acrivastina, Bw 825c
    Molecular Formula
    C22H24N2O2
    Molecular Weight
    348.4  g/mol
    InChI Key
    PWACSDKDOHSSQD-IUTFFREVSA-N
    FDA UNII
    A20F9XAI7W
    Acrivastine
    Acrivastine is a synthetic alkylamine with non-sedative antihistaminergic activity. Acrivastine competitively blocks the histamine H1 receptor and limits the typical allergic and anaphylactic responses, including bronchoconstriction, vasodilation, increased capillary permeability, and spasmodic contraction of gastrointestinal smooth muscle, caused by actions of histamine on bronchial, and gastrointestinal smooth muscles, and on capillaries. This drug also prevents histamine-induced pain and itching of the skin and mucous membranes. (NCI05)
    Acrivastine is a Histamine-1 Receptor Antagonist. The mechanism of action of acrivastine is as a Histamine H1 Receptor Antagonist.
    1 2D Structure

    Acrivastine

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (E)-3-[6-[(E)-1-(4-methylphenyl)-3-pyrrolidin-1-ylprop-1-enyl]pyridin-2-yl]prop-2-enoic acid
    2.1.2 InChI
    InChI=1S/C22H24N2O2/c1-17-7-9-18(10-8-17)20(13-16-24-14-2-3-15-24)21-6-4-5-19(23-21)11-12-22(25)26/h4-13H,2-3,14-16H2,1H3,(H,25,26)/b12-11+,20-13+
    2.1.3 InChI Key
    PWACSDKDOHSSQD-IUTFFREVSA-N
    2.1.4 Canonical SMILES
    CC1=CC=C(C=C1)C(=CCN2CCCC2)C3=CC=CC(=N3)C=CC(=O)O
    2.1.5 Isomeric SMILES
    CC1=CC=C(C=C1)/C(=C\CN2CCCC2)/C3=CC=CC(=N3)/C=C/C(=O)O
    2.2 Other Identifiers
    2.2.1 UNII
    A20F9XAI7W
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Bw 825c

    2. Bw-825c

    3. Bw825c

    4. Semprex

    2.3.2 Depositor-Supplied Synonyms

    1. 87848-99-5

    2. Semprex

    3. Acrivastin

    4. Acrivastinum

    5. Acrivastina

    6. Bw 825c

    7. Bw-825c

    8. Bw A825c

    9. Chebi:83168

    10. (e)-6-((e)-3-(1-pyrrolidinyl)-1-p-tolylpropenyl)-2-pyridineacrylic Acid

    11. 2-propenoic Acid, 3-(6-(1-(4-methylphenyl)-3-(1-pyrrolidinyl)-1-propenyl)-2-pyridinyl)-, (e,e)-

    12. A20f9xai7w

    13. 2-propenoic Acid,3-[6-[(1e)-1-(4-methylphenyl)-3-(1-pyrrolidinyl)-1-propenyl]-2-pyridinyl]-,(2e)-

    14. (e)-3-[6-[(e)-1-(4-methylphenyl)-3-pyrrolidin-1-ylprop-1-enyl]pyridin-2-yl]prop-2-enoic Acid

    15. Ncgc00182053-02

    16. Acrivastinum [latin]

    17. Acrivastina [spanish]

    18. Acrivastine [usan:inn:ban]

    19. (2e)-3-{6-[(1e)-1-(4-methylphenyl)-3-(pyrrolidin-1-yl)prop-1-en-1-yl]pyridin-2-yl}acrylic Acid

    20. Acrivastine (usan/inn)

    21. Unii-a20f9xai7w

    22. (e)-6-((e)-3-(1-pyrrolidinyl-1-p-tolylpropenyl)-2-pyridinacrylsaeure

    23. Acrivastine [mi]

    24. Acrivastine [inn]

    25. Dsstox_cid_2555

    26. Acrivastine [usan]

    27. Acrivastine [vandf]

    28. Schembl4702

    29. Acrivastine [mart.]

    30. Chembl1224

    31. Dsstox_rid_76625

    32. Dsstox_gsid_22555

    33. Acrivastine [who-dd]

    34. Mls006010115

    35. Bidd:gt0209

    36. Bw270c

    37. Dtxsid6022555

    38. Acrivastine, >=98% (hplc)

    39. Acrivastine [orange Book]

    40. Hms3886e20

    41. Bcp06189

    42. Hy-b1510

    43. Zinc3776633

    44. Tox21_113015

    45. Ac-912

    46. Bdbm50487466

    47. Benadryl Allgy Relief Plus Decongest

    48. Mfcd00869830

    49. S5718

    50. Akos005067182

    51. Semprex-d Component Acrivastine

    52. Cs-6454

    53. Db09488

    54. Ncgc00182053-03

    55. (2e)-3-{6-[(1e)-1-(4-methylphenyl)-3-pyrrolidin-1-ylprop-1-en-1-yl]pyridin-2-yl}prop-2-enoic Acid

    56. Acrivastine Component Of Semprex-d

    57. As-14623

    58. Smr004701250

    59. Cas-87848-99-5

    60. D02760

    61. D70156

    62. 848a995

    63. A916142

    64. Q342745

    65. Sr-01000942220

    66. Q-200590

    67. Sr-01000942220-1

    68. (e)-3-{6-[3-pyrrolidino-1-(4-tolyl)prop-1e-enyl]-2-pyridyl}acrylic Acid

    69. 6-(3-(1-pyrrolidinyl)-1-p-tolylpropenyl)-2-pyridineacrylic Acid

    70. (e)-3-(6-((e)-3-(pyrrolidin-1-yl)-1-(p-tolyl)prop-1-en-1-yl)pyridin-2-yl)acrylic Acid

    71. 3-(6-(1-(4-methylphenyl)-3-(1-pyrrolidinyl)-1-propenyl)-2-pyridinyl)-

    72. 2-propenoic Acid, 3-[6-[(1e)-1-(4-methylphenyl)-3-(1-pyrrolidinyl)-1-propen-1-yl]-2-pyridinyl]-, (2e)-

    2.4 Create Date
    2005-09-16
    3 Chemical and Physical Properties
    Molecular Weight 348.4 g/mol
    Molecular Formula C22H24N2O2
    XLogP31.6
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count4
    Rotatable Bond Count6
    Exact Mass348.183778013 g/mol
    Monoisotopic Mass348.183778013 g/mol
    Topological Polar Surface Area53.4 Ų
    Heavy Atom Count26
    Formal Charge0
    Complexity514
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count2
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    For the relief of symptoms associated with seasonal allergic rhinitis such as sneezing, rhinorrhea, pruritus, lacrimation, and nasal congestion.

    FDA Label

    5 Pharmacology and Biochemistry
    5.1 MeSH Pharmacological Classification

    Histamine H1 Antagonists, Non-Sedating

    A class of non-sedating drugs that bind to but do not activate histamine receptors (DRUG INVERSE AGONISM), thereby blocking the actions of histamine or histamine agonists. These antihistamines represent a heterogenous group of compounds with differing chemical structures, adverse effects, distribution, and metabolism. Compared to the early (first generation) antihistamines, these non-sedating antihistamines have greater receptor specificity, lower penetration of BLOOD-BRAIN BARRIER, and are less likely to cause drowsiness or psychomotor impairment. (See all compounds classified as Histamine H1 Antagonists, Non-Sedating.)

    5.2 FDA Pharmacological Classification
    5.2.1 Active Moiety
    ACRIVASTINE
    5.2.2 FDA UNII
    A20F9XAI7W
    5.2.3 Pharmacological Classes
    Established Pharmacologic Class [EPC] - Histamine-1 Receptor Antagonist
    5.3 ATC Code

    R - Respiratory system

    R06 - Antihistamines for systemic use

    R06A - Antihistamines for systemic use

    R06AX - Other antihistamines for systemic use

    R06AX18 - Acrivastine

    5.4 Absorption, Distribution and Excretion

    Absorption

    Acrivastine was absorbed rapidly from the combination capsule following oral administration and was as bioavailable as a solution of acrivastine. After administration of SEMPREX-D Capsules, maximum plasma acrivastine concentrations were achieved at 1.14 0.23 hour.

    Route of Elimination

    A mass balance study in 7 healthy volunteers showed that acrivastine is primarily eliminated by the kidneys. Over a 72-hour collection period, about 84% of the administered total radioactivity was recovered in urine and about 13% in feces, for a combined recovery of about 97%.

    Volume of Distribution

    0.46 0.05 L/kg

    Clearance

    2.9 0.7 mL/min/kg

    5.5 Biological Half-Life

    The mean terminal half-life for acrivastine was 1.9 0.3 hours following single oral doses and increased to 3.5 1.9 hours at steady state. The terminal half-life for the propionic acid metabolite was 3.8 1.4 hours.

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