Clobutinol HCl

Synopsis, Chemistry

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Also known as: 14860-49-2, Clobutinol [inn], Clobutinolum, Iversal, 1-(4-chlorophenyl)-4-(dimethylamino)-2,3-dimethylbutan-2-ol, Clobutinol (inn)

Molecular Formula

C₁₄H₂₂ClNO

Molecular Weight

255.78 g/mol

InChI Key

KVHHQGIIZCJATJ-UHFFFAOYSA-N

FDA UNII

1NY2IX043A

Clobutinol is a cough suppressant that is withdrawn from the US and EU markets. Clobutinol may prolong the QT interval. In 2007, Clobutinol was determined to cause cardiac arrhythmia in some patients.

1 2D Structure

Clobutinol HCl

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

1-(4-chlorophenyl)-4-(dimethylamino)-2,3-dimethylbutan-2-ol

2.1.2 InChI

InChI=1S/C14H22ClNO/c1-11(10-16(3)4)14(2,17)9-12-5-7-13(15)8-6-12/h5-8,11,17H,9-10H2,1-4H3

2.1.3 InChI Key

KVHHQGIIZCJATJ-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC(CN(C)C)C(C)(CC1=CC=C(C=C1)Cl)O

2.2 Other Identifiers

2.2.1 UNII

1NY2IX043A

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Biotetrussin

2. Chlorodimenol

3. Clobutinol Hydrochloride

4. Kat 250

5. Petoxil

6. Silomat

2.3.2 Depositor-Supplied Synonyms

1. 14860-49-2

2. Clobutinol [inn]

3. Clobutinolum

4. Iversal

5. 1-(4-chlorophenyl)-4-(dimethylamino)-2,3-dimethylbutan-2-ol

6. Clobutinol (inn)

7. Iversal (tn)

8. 1-(4-chlorophenyl)-2,3-dimethyl-4-dimethylamino-2-butanol

9. C14h22clno

10. 1ny2ix043a

11. R05db03

12. Kat 256 [as Hydrochloride]

13. Clobutinolum [inn-latin]

14. Benzeneethanol, 4-chloro-.alpha.-[2-(dimethylamino)-1-methylethyl]-.alpha.-methyl-

15. Ncgc00159437-02

16. Einecs 238-926-4

17. Brn 2843490

18. Unii-1ny2ix043a

19. Benzeneethanol, 4-chloro-.alpha.-(2-(dimethylamino)-1-methylethyl)-.alpha.-methyl-

20. Clobutinol [mi]

21. 4-chloro-alpha(2-(dimethylamino)-1-methylethyl)alpha-methylbenzeneethanol

22. Benzeneethanol, 4-chloro-alpha-(2-(dimethylamino)-1-methyl)-alpha-methyl-

23. Benzeneethanol, 4-chloro-alpha-(2-(dimethylamino)-1-methylethyl)-alpha-methyl-

24. P-chloro-alpha-(2-(dimethylamino)-1-methylethyl)-alpha-methyl-phenethyl Alcohol

25. Clobutinol [who-dd]

26. P-cloro-alpha-(2-(dimetilamino)-1-metiletil)-alpha-metil Fenetil Alcool [italian]

27. Kat 256 Free Base

28. Kat-256 Free Base

29. Schembl148543

30. Chembl1474889

31. Dtxsid2022838

32. Chebi:94381

33. P-chloro-alpha-(2-(dimethylamino)-1-methylethyl)-alpha-methylphenethyl Alcohol

34. P-cloro-alpha-(2-(dimetilamino)-1-metiletil)-alpha-metil Fenetil Alcool

35. Db09004

36. Phenethyl Alcohol, P-chloro-.alpha.-[2-(dimethylamino)-1-methylethyl]-.alpha.-methyl-

37. Phenethyl Alcohol, P-chloro-alpha-(2-(dimethylamino)-1-methylethyl)-alpha-methyl-

38. Hy-148144

39. Cs-0613654

40. Ft-0714887

41. D07716

42. Diethylenetriamine Crosslinked With Epichlorohydrin

43. Q415654

44. Brd-a43809092-003-01-3

45. 1-(4-chlorophenyl)-4-(dimethylamino)-2,3-dimethyl-2-butanol

46. (2s)-1-(4-chlorophenyl)-4-(dimethylamino)-2,3-dimethylbutan-2-ol

47. Benzeneethanol, 4-chloro-.alpha.-(2-(dimethylamino)-1-methyl)-.alpha.-methyl-

48. P-chloro-.alpha.-(2-(dimethylamino)-1-methylethyl)-.alpha.-methyl-phenethyl Alcohol

49. P-chloro-.alpha.-(2-(dimethylamino)-1-methylethyl)-.alpha.-methylphenethyl Alcohol

50. P-chloro-.alpha.-[2-(dimethylamino)-1-methylethyl]-.alpha.-methylphenyl Alcohol

51. P-cloro-.alpha.-(2-(dimetilamino)-1-metiletil)-.alpha.-metil Fenetil Alcool

2.4 Create Date

2005-03-27

3 Chemical and Physical Properties

Molecular Formula	C₁₄H₂₂ClNO
Molecular Weight	255.78 g/mol
XLogP3	3.2
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	5
Exact Mass	255.1389920 g/mol
Monoisotopic Mass	255.1389920 g/mol
Topological Polar Surface Area	23.5 Å²
Heavy Atom Count	17
Formal Charge	0
Complexity	226
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	2
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Antitussive Agents

Agents that suppress cough. They act centrally on the medullary cough center. EXPECTORANTS, also used in the treatment of cough, act locally. (See all compounds classified as Antitussive Agents.)

4.2 ATC Code

R - Respiratory system

R05 - Cough and cold preparations

R05D - Cough suppressants, excl. combinations with expectorants

R05DB - Other cough suppressants

R05DB03 - Clobutinol