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Chemistry

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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

Bromodiphenhydramine

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 Formula	C₁₇H₂₀BrNO
Molecular Weight	334.2 g/mol
XLogP3	4
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	6
Exact Mass	333.07283 g/mol
Monoisotopic Mass	333.07283 g/mol
Topological Polar Surface Area	12.5 Å²
Heavy Atom Count	20
Formal Charge	0
Complexity	258
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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.

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