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Oxyphenonium

Oxyphenonium

Synopsis, Chemistry

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Also known as: 50-10-2, Spasmophen, Oxifenon, Oxyfenon, Oxyphenon, Antrenyl

Molecular Formula

C₂₁H₃₄BrNO₃

Molecular Weight

428.4 g/mol

InChI Key

UKLQXHUGTKWPSR-UHFFFAOYSA-M

FDA UNII

S9421HWB3Z

A quaternary ammonium anticholinergic agent with peripheral side effects similar to those of ATROPINE. It is used as an adjunct in the treatment of gastric and duodenal ulcer, and to relieve visceral spasms. The drug has also been used in the form of eye drops for mydriatic effect.

1 2D Structure

Oxyphenonium

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-(2-cyclohexyl-2-hydroxy-2-phenylacetyl)oxyethyl-diethyl-methylazanium;bromide

2.1.2 InChI

InChI=1S/C21H34NO3.BrH/c1-4-22(3,5-2)16-17-25-20(23)21(24,18-12-8-6-9-13-18)19-14-10-7-11-15-19;/h6,8-9,12-13,19,24H,4-5,7,10-11,14-17H2,1-3H3;1H/q+1;/p-1

2.1.3 InChI Key

UKLQXHUGTKWPSR-UHFFFAOYSA-M

2.1.4 Canonical SMILES

CC[N+](C)(CC)CCOC(=O)C(C1CCCCC1)(C2=CC=CC=C2)O.[Br-]

2.2 Other Identifiers

2.2.1 UNII

S9421HWB3Z

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 2-((cyclohexylhydroxyphenylacetyl)oxy)-n,n-diethyl-n-methylethanaminium

2. Atrenyl

3. Bromide, Oxyphenonium

4. Chloride, Oxyphenonium

5. Iodide, Oxyphenonium

6. Metacin

7. Methacin

8. Oxyphenon

9. Oxyphenonium

10. Oxyphenonium Bromide, (+)-isomer

11. Oxyphenonium Bromide, (+-)-isomer

12. Oxyphenonium Bromide, (-)-isomer

13. Oxyphenonium Chloride

14. Oxyphenonium Iodide

15. Oxyphenonium Iodide, (r)-isomer

16. Oxyphenonium Iodide, (s)-isomer

17. Oxyphenonium, (+-)-isomer

18. Oxyphenonium, (r)-isomer

19. Oxyphenonium, (s)-isomer

20. Spastrex

2.3.2 Depositor-Supplied Synonyms

1. 50-10-2

2. Spasmophen

3. Oxifenon

4. Oxyfenon

5. Oxyphenon

6. Antrenyl

7. Oxyphenoniumbromide

8. Antrenil

9. Spasmodin

10. Ba-5473

11. Oxyphenonium (bromide)

12. Nsc-759248

13. Mls000028620

14. S9421hwb3z

15. 2-(2-cyclohexyl-2-hydroxy-2-phenylacetyl)oxyethyl-diethyl-methylazanium;bromide

16. Smr000058660

17. Subranyl

18. Antrenyl Bromide

19. C-5473

20. Oxyphenonium Bromide (inn)

21. Dsstox_cid_25632

22. Dsstox_rid_81014

23. Ethanaminium, 2-((cyclohexylhydroxyphenylacetyl)oxy)-n,n-diethyl-n-methyl-, Bromide

24. Dsstox_gsid_45632

25. Oxyphenonium Bromide [inn]

26. Cas-50-10-2

27. Oxyphenonii Bromidum

28. Bromuro De Oxifenonio

29. Bromure D'oxyphenonium

30. Oxyphenonium Bromide [inn:ban]

31. Oxyphenonii Bromidum [inn-latin]

32. Ncgc00018256-02

33. Einecs 200-010-7

34. Bromure D'oxyphenonium [inn-french]

35. Bromuro De Oxifenonio [inn-spanish]

36. Unii-s9421hwb3z

37. C 5473

38. Antrenyl (tn)

39. Opera_id_1635

40. Diethyl(2-hydroxyethyl)methylammonium Bromide Alpha-phenylcyclohexaneglycolate

41. Regid_for_cid_5748

42. Mls001076268

43. Mls001424168

44. Schembl248890

45. Chembl1200906

46. Dtxsid4045632

47. Oxyphenonium Bromide [mi]

48. Hms2052o07

49. Hms2230j18

50. Hms3371m04

51. Hms3394o07

52. Pharmakon1600-01505783

53. (+/-)-oxyphenonium Bromide

54. Oxyphenonium Bromide [vandf]

55. Tox21_110851

56. Nsc759248

57. Oxyphenonium Bromide [mart.]

58. Oxyphenonium Bromide [who-dd]

59. Akos030507607

60. Tox21_110851_1

61. Ccg-101094

62. Ccg-213986

63. Nc00344

64. Ammonium, Diethyl(2-hydroxyethyl)methyl-, Bromide, Alpha-phenylcyclohexaneglycolate

65. Ncgc00018256-06

66. Oxyphenonium Bromide [orange Book]

67. D06877

68. Sr-01000003140

69. Q7116109

70. Sr-01000003140-4

71. Z1551429731

72. {2-[(2-cyclohexyl-2-hydroxy-2-phenylacetyl)oxy]ethyl}diethylmethylazanium Bromide

73. 2-(2-cyclohexyl-2-hydroxy-2-phenylacetoxy)-n,n-diethyl-n-methylethan-1-aminium Bromide

74. Diethyl(2-hydroxyethyl)methylammonium Bromide .alpha.-phenylcyclohexaneglycolate

75. Ethanaminium, 2-((2-cyclohexyl-2-hydroxy-2-phenylacetyl)oxy)-n,n-diethyl-n-methyl-, Bromide (1:1)

2.4 Create Date

2005-06-29

3 Chemical and Physical Properties

Molecular Formula	C₂₁H₃₄BrNO₃
Molecular Weight	428.4 g/mol
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	9
Exact Mass	427.17221 g/mol
Monoisotopic Mass	427.17221 g/mol
Topological Polar Surface Area	46.5 Å²
Heavy Atom Count	26
Formal Charge	0
Complexity	409
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	2

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Mydriatics

Agents that dilate the pupil. They may be either sympathomimetics or parasympatholytics. (See all compounds classified as Mydriatics.)

Muscarinic Antagonists

Drugs that bind to but do not activate MUSCARINIC RECEPTORS, thereby blocking the actions of endogenous ACETYLCHOLINE or exogenous agonists. Muscarinic antagonists have widespread effects including actions on the iris and ciliary muscle of the eye, the heart and blood vessels, secretions of the respiratory tract, GI system, and salivary glands, GI motility, urinary bladder tone, and the central nervous system. (See all compounds classified as Muscarinic Antagonists.)

Parasympatholytics

Agents that inhibit the actions of the parasympathetic nervous system. The major group of drugs used therapeutically for this purpose is the MUSCARINIC ANTAGONISTS. (See all compounds classified as Parasympatholytics.)