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Dichlorobenzyl Alcohol

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Also known as: 1777-82-8, (2,4-dichlorophenyl)methanol, Dybenal, 2,4-dichlorobenzenemethanol, Rapidosept, Benzenemethanol, 2,4-dichloro-

Molecular Formula

C₇H₆Cl₂O

Molecular Weight

177.02 g/mol

InChI Key

DBHODFSFBXJZNY-UHFFFAOYSA-N

FDA UNII

1NKX3648J9

Dichlorobenzyl alcohol is a mild antiseptic with a broad spectrum for bacterial and virus associated with mouth and throat infections. Dichlorobenzyl alcohol is considered as an active ingredient found in several marketed OTC products by Health Canada which has categorized this agent as an anatomical therapeutic chemical. On the other hand, dichlorobenzyl alcohol is categorized by the FDA in the inactive ingredient for approved drug products.

1 2D Structure

Dichlorobenzyl Alcohol

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2,4-dichlorophenyl)methanol

2.1.2 InChI

InChI=1S/C7H6Cl2O/c8-6-2-1-5(4-10)7(9)3-6/h1-3,10H,4H2

2.1.3 InChI Key

DBHODFSFBXJZNY-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C1=CC(=C(C=C1Cl)Cl)CO

2.2 Other Identifiers

2.2.1 UNII

1NKX3648J9

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Dichlorobenzyl Alcohol

2.3.2 Depositor-Supplied Synonyms

1. 1777-82-8

2. (2,4-dichlorophenyl)methanol

3. Dybenal

4. 2,4-dichlorobenzenemethanol

5. Rapidosept

6. Benzenemethanol, 2,4-dichloro-

7. Myacide Sp

8. Benzyl Alcohol, 2,4-dichloro-

9. Chebi:48220

10. Mfcd00004606

11. Nsc-15635

12. 1nkx3648j9

13. Ncgc00181337-01

14. Dsstox_cid_21362

15. Dsstox_rid_79699

16. Dsstox_gsid_41362

17. Cas-1777-82-8

18. 2,4-dichlorobenzylalcohol

19. Einecs 217-210-5

20. Nsc 15635

21. 2,4-dichlorobenzoyl Alcohol

22. Brn 1448652

23. Unii-1nkx3648j9

24. Ai3-20619

25. Schembl41323

26. Oxiconazole Related Compound D

27. Chembl3184437

28. Dtxsid9041362

29. (2,4-dichlorophenyl)methanol #

30. Dalc2-h_000039

31. Zinc157458

32. 2,4-dichlorobenzyl Alcohol, 99%

33. Dichlorobenzyl Alcohol [ii]

34. Dichlorobenzyl Alcohol [mi]

35. Nsc15635

36. Tox21_112796

37. Tox21_300895

38. Bdbm50498198

39. Dichlorobenzyl Alcohol [inci]

40. S6067

41. Stl480884

42. Dichlorobenzyl Alcohol [vandf]

43. Akos000248902

44. Dichlorobenzyl Alcohol [mart.]

45. Tox21_112796_1

46. Am81457

47. Db13269

48. Dichlorobenzyl Alcohol [who-dd]

49. Hy-w039454

50. Ps-5315

51. Ncgc00181337-02

52. Ncgc00181337-03

53. Ncgc00254799-01

54. Ac-10679

55. Sy015811

56. Db-015914

57. Cs-0097299

58. D1837

59. Ft-0610050

60. Ft-0674330

61. 77d828

62. Oxiconazole Related Compound D [usp-rs]

63. 2,4-dichlorobenzyl Alcohol [ep Monograph]

64. Q209202

65. Sr-01000944729

66. Sr-01000944729-1

67. W-107827

68. (2,4-dichlorophenyl)methanol;2,4-dichlorobenzyl Alcohol

69. Z111479786

70. 2,4-dichlorobenzyl Alcohol, European Pharmacopoeia (ep) Reference Standard

2.4 Create Date

2005-03-26

3 Chemical and Physical Properties

Molecular Formula	C₇H₆Cl₂O
Molecular Weight	177.02 g/mol
XLogP3	2.5
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	1
Rotatable Bond Count	1
Exact Mass	175.9795702 g/mol
Monoisotopic Mass	175.9795702 g/mol
Topological Polar Surface Area	20.2 Å²
Heavy Atom Count	10
Formal Charge	0
Complexity	108
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

Dichlorobenzyl alcohol in combination with [DB13908] is available in over-the-counter products used for symptomatic relief of acute sore throat and postoperative sore throat.

5 Pharmacology and Biochemistry

5.1 Pharmacology

In vitro studies with the combination of dichlorobenzyl alcohol and amylmetacresol have shown a virucidal against a number of viruses associated with the common cold which is observed by a reduction in the viral load. In clinical trials, administration of dichlorobenzyl alcohol lozenges has been shown to generate a reduced throat soreness and to provide pain relief and relief from difficulty in swallowing 5 minutes after administration. This effect can last for even 2 hours. The relief effect was shown to reach a steady-state after 45 minutes.

5.2 ATC Code

R - Respiratory system

R02 - Throat preparations

R02A - Throat preparations

R02AA - Antiseptics

R02AA03 - Dichlorobenzyl alcohol

5.3 Absorption, Distribution and Excretion

Absorption

Dichlorobenzyl alcohol is released almost immediately from its formulation and reaches peak concentration after 3-4 minutes. The concentration in saliva after 120 minutes represents about 50% of the administered dose.

Route of Elimination

In preclinical trials, dermal administration of dichlorobenzyl alcohol results in renal elimination of 90% of the administered dose. After metabolism, dichlorobenzyl alcohol is excreted in the urine.

Volume of Distribution

This pharmacokinetic property has not been fully studied.

Clearance

This pharmacokinetic property has not been fully studied.

5.4 Metabolism/Metabolites

Dichlorobenzyl alcohol is metabolized in the liver to form hippuric acid.

5.5 Biological Half-Life

This pharmacokinetic property has not been fully studied.

5.6 Mechanism of Action

The use of dichlorobenzyl alcohol has been related to its antibacterial, antiviral and local anesthetic properties. The local anesthetic action of dichlorobenzyl alcohol is thought to be due to a reduced sodium channel blockade. The antiseptic mechanism of action of dichlorobenzyl alcohol is not fully understood but it is thought to be related to a denaturation of external proteins and rearrangement of the tertiary structure proteins.