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    bromazine

    ACTIVE PHARMA INGREDIENTS

    FINISHED DOSAGE FORMULATIONS

    DIGITAL CONTENT

    REF. STANDARDS & IMPURITIES

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    2D Structure
    Also known as: Bromodiphenhydramine, Bromdiphenhydramine, 118-23-0, Histabromamine, Deserol, Neo-benadryl
    Molecular Formula
    C17H20BrNO
    Molecular Weight
    334.2  g/mol
    InChI Key
    NUNIWXHYABYXKF-UHFFFAOYSA-N
    FDA UNII
    T032BI7727
    Bromodiphenhydramine is a brominated derivative of diphenhydramine, an ethanolamine derivative and histamine H1 receptor antagonist with anti-allergic, sedative, antiemetic and anticholinergic properties. Bromazine competitively and selectively blocks central and peripheral histamine H1 receptors, thereby alleviating the symptoms caused by endogenous histamine on bronchial, capillary and gastrointestinal (GI) smooth muscles. This prevents histamine-induced bronchoconstriction, vasodilation, increased capillary permeability, itching, and spasmodic contractions of GI smooth muscle. In addition, bromazine binds to and blocks peripheral and central muscarinic receptors.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    2-[(4-bromophenyl)-phenylmethoxy]-N,N-dimethylethanamine
    2.1.2 InChI
    InChI=1S/C17H20BrNO/c1-19(2)12-13-20-17(14-6-4-3-5-7-14)15-8-10-16(18)11-9-15/h3-11,17H,12-13H2,1-2H3
    2.1.3 InChI Key
    NUNIWXHYABYXKF-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CN(C)CCOC(C1=CC=CC=C1)C2=CC=C(C=C2)Br
    2.2 Other Identifiers
    2.2.1 UNII
    T032BI7727
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Ambodryl

    2. Bromodiphenhydramine

    3. Bromodiphenhydramine Hydrochloride

    2.3.2 Depositor-Supplied Synonyms

    1. Bromodiphenhydramine

    2. Bromdiphenhydramine

    3. 118-23-0

    4. Histabromamine

    5. Deserol

    6. Neo-benadryl

    7. Bromazina

    8. Bromazinum

    9. Amodryl

    10. Ambodryl

    11. Bromazin

    12. 2-[(4-bromophenyl)-phenylmethoxy]-n,n-dimethylethanamine

    13. 2-(p-bromo-alpha-phenylbenzyloxy)-n,n-dimethylethylamine

    14. Beta-(p-bromobenzhydryloxy)ethyldimethylamine

    15. 2-((4-bromophenyl)(phenyl)methoxy)-n,n-dimethylethanamine

    16. N-2-(4-bromobenzhydryloxy)ethyldimethylamine

    17. Beta-dimethylaminoethyl P-bromobenzhydryl Ether

    18. Chebi:59177

    19. Bromdiphenhydraminum

    20. T032bi7727

    21. 2-[(4-bromophenyl)(phenyl)methoxy]-n,n-dimethylethanamine

    22. Ethanamine, 2-[(4-bromophenyl)phenylmethoxy]-n,n-dimethyl-

    23. Bromo-benadryl

    24. Bromazine [inn:ban]

    25. 2-(4-bromobenzhydryloxy)-nn-dimethylethylamine

    26. Bromazinum [inn-latin]

    27. Bromazina [inn-spanish]

    28. Ethanamine, 2-((4-bromophenyl)phenylmethoxy)-n,n-dimethyl-

    29. (6r,7r)-7-[[(z)-2-(2-amino-1,3-thiazol-4-yl)-4-carboxybut-2-enoyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid,dihydrate

    30. Einecs 204-238-8

    31. Bromazin Base

    32. Deserol Base

    33. Unii-t032bi7727

    34. Bromo-benadryl Base

    35. Bromodiphen-hydramine

    36. 4-bromodiphen Hydramine

    37. Bromazine [inn]

    38. Diphenhydramine Impurity C

    39. Dsstox_cid_2688

    40. Bromazine [who-dd]

    41. Dsstox_rid_97539

    42. Dsstox_gsid_22688

    43. Schembl29806

    44. Gtpl7132

    45. Dimenhydrinate Impurity H

    46. Chembl1201245

    47. Dtxsid6022688

    48. Bdbm81465

    49. Bromodiphenhydramine [mi]

    50. (+/-)-bromodiphenhydramine

    51. 2-{[(4-bromophenyl)(phenyl)methyl]oxy}-n,n-dimethylethanamine

    52. Bromodiphenhydramine [vandf]

    53. Cas_2444

    54. Hy-b1568

    55. Nsc_2444

    56. Tox21_113667

    57. Pdsp1_000145

    58. Pdsp2_000144

    59. Bromodiphenhydramine, (+/-)-

    60. Db01237

    61. Ncgc00249891-01

    62. Cas-118-23-0

    63. Cs-0013459

    64. .beta.-(p-bromobenzhydryloxy)ethyldimethylamine

    65. 4-bromodiphen Hydramine [usp Impurity]

    66. Dimenhydrinate Impurity H [ep Impurity]

    67. L001164

    68. Sr-01000944388

    69. Q4926102

    70. Sr-01000944388-1

    71. {2-[(4-bromophenyl)(phenyl)methoxy]ethyl}dimethylamine

    72. 2-[(4-bromophenyl)(phenyl)methoxy]-n,n-dimethylethanamine #

    73. 2-[(p-bromo-.alpha.-phenylbenzyl)oxy]-n,n-dimethylethylamine

    74. Diphenhydramine Hydrochloride Impurity C [ep Impurity]

    75. Ethylamine, 2-[(p-bromo-.alpha.-phenylbenzyl)oxy]-n,n-dimethyl-

    2.4 Create Date
    2005-03-25
    3 Chemical and Physical Properties
    Molecular Weight 334.2 g/mol
    Molecular Formula C17H20BrNO
    XLogP34
    Hydrogen Bond Donor Count0
    Hydrogen Bond Acceptor Count2
    Rotatable Bond Count6
    Exact Mass333.07283 g/mol
    Monoisotopic Mass333.07283 g/mol
    Topological Polar Surface Area12.5 Ų
    Heavy Atom Count20
    Formal Charge0
    Complexity258
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count1
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    For management of symptoms related to hay fever and other types of allergy and used to help bring up phlegm, thin secretions, and make a cough productive.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Bromodiphenhydramine is an antihistamine of the ethanolamine class. Ethanolamine antihistamines have significant antimuscarinic activity and produce marked sedation in most patients. In addition to the usual allergic symptoms, the drug also treats irritant cough and nausea, vomiting, and vertigo associated with motion sickness. It also is used commonly to treat drug-induced extrapyramidal symptoms as well as to treat mild cases of Parkinson's disease. Rather than preventing the release of histamine, as do cromolyn and nedocromil, Bromodiphenhydramine competes with free histamine for binding at HA-receptor sites. Bromodiphenhydramine competitively antagonizes the effects of histamine on HA-receptors in the GI tract, uterus, large blood vessels, and bronchial muscle. Ethanolamine derivatives have greater anticholinergic activity than do other antihistamines, which probably accounts for the antidyskinetic action of Bromodiphenhydramine. This anticholinergic action appears to be due to a central antimuscarinic effect, which also may be responsible for its antiemetic effects, although the exact mechanism is unknown.

    5.2 ATC Code

    R - Respiratory system

    R06 - Antihistamines for systemic use

    R06A - Antihistamines for systemic use

    R06AA - Aminoalkyl ethers

    R06AA01 - Bromazine

    5.3 Absorption, Distribution and Excretion

    Absorption

    Well absorbed in the digestive tract.

    5.4 Metabolism/Metabolites

    Hepatic (cytochrome P-450 system); some renal.

    5.5 Biological Half-Life

    1 to 4 hours

    5.6 Mechanism of Action

    Bromodiphenhydramine competes with free histamine for binding at HA-receptor sites. This antagonizes the effects of histamine on HA-receptors, leading to a reduction of the negative symptoms brought on by histamine HA-receptor binding.