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Also known as: 5-methyl-2-pentylphenol, 1300-94-3, 5-methyl-2-n-pentylphenol, 6-pentyl-m-cresol, 6-amyl-m-cresol, 6-n-amyl-m-cresol

Molecular Formula

C₁₂H₁₈O

Molecular Weight

178.27 g/mol

InChI Key

CKGWFZQGEQJZIL-UHFFFAOYSA-N

FDA UNII

05W904P57F

Amylmetacresol is an antiseptic available in Canada over-the-counter in a number of lozenges for the treatment of sore throat and minor mouth infections,. Amylmetacresol is often combined with dichlorobenzyl alcohol and menthol in the commonly used sore throat lozenges, known as Strepsils. The acute sore throat (pharyngitis) is one of the most common conditions for which children are seen in the primary care setting. Pharyngitis is normally caused by viruses and proves benign and self-limiting. Clinically proven, over-the-counter throat lozenges offer rapid and effective relief of acute sore throat symptoms, and are increasingly important in the management of this condition.

1 2D Structure

Amylmetacresol

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

5-methyl-2-pentylphenol

2.1.2 InChI

InChI=1S/C12H18O/c1-3-4-5-6-11-8-7-10(2)9-12(11)13/h7-9,13H,3-6H2,1-2H3

2.1.3 InChI Key

CKGWFZQGEQJZIL-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CCCCCC1=C(C=C(C=C1)C)O

2.2 Other Identifiers

2.2.1 UNII

05W904P57F

2.3 Synonyms

2.3.1 Depositor-Supplied Synonyms

1. 5-methyl-2-pentylphenol

2. 1300-94-3

3. 5-methyl-2-n-pentylphenol

4. 6-pentyl-m-cresol

5. 6-amyl-m-cresol

6. 6-n-amyl-m-cresol

7. 6-n-pentyl-m-cresol

8. Amylmetacresolum

9. Phenol, 5-methyl-2-pentyl-

10. Amyl Metacresol

11. 2-amyl-5-methylphenol

12. Chebi:48213

13. 05w904p57f

14. Ncgc00180998-01

15. Amilmetacresol

16. Amilmetacresol [spanish]

17. Amylmetacresolum [latin]

18. Amylmetacresol [inn:ban]

19. Brn 2440952

20. M-cresol, 6-pentyl-

21. Einecs 215-094-0

22. Unii-05w904p57f

23. Amylmetacresol [inn]

24. Dsstox_cid_26791

25. Dsstox_rid_81908

26. Dsstox_gsid_46791

27. 3-06-00-02005 (beilstein Handbook Reference)

28. Amylmetacresol [vandf]

29. Schembl302197

30. Amylmetacresol [mart.]

31. Amyl Metacresol [vandf]

32. Amylmetacresol [who-dd]

33. Chembl1512677

34. Dtxsid8046791

35. 6-n-amyl-m-cresol [mi]

36. Baa30094

37. Zinc2039651

38. Amylmetacresol [ep Impurity]

39. Tox21_112651

40. Amylmetacresol [ep Monograph]

41. Mfcd00127710

42. S6173

43. Stl453583

44. Akos015912095

45. Db13908

46. 5-methyl-2-n-pentylphenol, Aldrichcpr

47. Ds-15450

48. Cas-1300-94-3

49. Hy-121527

50. Cs-0082471

51. Ft-0620948

52. Amylmetacresol 100 Microg/ml In Acetonitrile

53. A888790

54. Sr-01000944860

55. Q1946346

56. Sr-01000944860-1

57. W-108357

2.4 Create Date

2005-08-08

3 Chemical and Physical Properties

Molecular Formula	C₁₂H₁₈O
Molecular Weight	178.27 g/mol
XLogP3	4.4
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	1
Rotatable Bond Count	4
Exact Mass	178.135765193 g/mol
Monoisotopic Mass	178.135765193 g/mol
Topological Polar Surface Area	20.2 Å²
Heavy Atom Count	13
Formal Charge	0
Complexity	133
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

Sore throat, minor mouth and throat infections,,.

5 Pharmacology and Biochemistry

5.1 Pharmacology

The mixture of amylmetacresol throat lozenge medications markedly reduces the infectivity of certain infectious viruses in the throat and in cough droplets, thus reducing opportunities for person-to-person transmission. In addition, it relieves symptoms of sore throat/irritation of the throat,. Amylmetacresol is thought to inhibit the inflammatory and pain mediators that are involved in the inflammation of the mouth and throat mucous membranes, as well as the sore throat.

5.2 Absorption, Distribution and Excretion

Absorption

Rapidly absorbed and eliminated.

5.3 Mechanism of Action

The mechanism of virucidal action is not fully elucidated, however it is suggested that denaturation of external protein spikes, a pH-induced rearrangement of the tertiary structure of attachment proteins, or a selective effect on viral lipid membranes/proteinlipid interaction is responsible for this action. Amylmetacresol is an antibacterial and antiviral agent, and blocks voltage-gated Na channels in a local anesthetic-like manner.

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