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(2,3-Dichloro-4-(2-thenoyl)phenoxy)acetic Acid

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Chemistry

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Also known as: Ticrynafen, 40180-04-9, Thienylic acid, Selacryn, Diflurex, Ticrex

Molecular Formula

C₁₃H₈Cl₂O₄S

Molecular Weight

331.2 g/mol

InChI Key

AGHANLSBXUWXTB-UHFFFAOYSA-N

FDA UNII

HC95205SY4

A novel diuretic with uricosuric action. It has been proposed as an antihypertensive agent.

1 2D Structure

Ticrynafen

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-[2,3-dichloro-4-(thiophene-2-carbonyl)phenoxy]acetic acid

2.1.2 InChI

InChI=1S/C13H8Cl2O4S/c14-11-7(13(18)9-2-1-5-20-9)3-4-8(12(11)15)19-6-10(16)17/h1-5H,6H2,(H,16,17)

2.1.3 InChI Key

AGHANLSBXUWXTB-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C1=CSC(=C1)C(=O)C2=C(C(=C(C=C2)OCC(=O)O)Cl)Cl

2.2 Other Identifiers

2.2.1 UNII

HC95205SY4

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Acid, Thienylic

2. Acid, Tienilic

3. Anp 3624

4. Anp-3624

5. Anp3624

6. Selacryn

7. Skf 62698

8. Skf-62698

9. Skf62698

10. Thienylic Acid

11. Ticrynafen

2.3.2 Depositor-Supplied Synonyms

1. Ticrynafen

2. 40180-04-9

3. Thienylic Acid

4. Selacryn

5. Diflurex

6. Ticrex

7. Ticrynafen [usan]

8. Acido Tienilico

9. Acide Tienilique

10. Acidum Tienilicum

11. 2-(2,3-dichloro-4-(thiophene-2-carbonyl)phenoxy)acetic Acid

12. (2,3-dichloro-4-(2-thenoyl)phenoxy)acetic Acid

13. 4-(2-thienylketo)-2,3-dichlorophenoxyacetic Acid

14. 2-[2,3-dichloro-4-(thiophene-2-carbonyl)phenoxy]acetic Acid

15. (2,3-dichloro-4-(2-thiophenecarbonyl)phenoxy)acetic Acid

16. Tienilic Acid [inn]

17. [2,3-dichloro-4-(2-thienylcarbonyl)phenoxy]acetic Acid

18. Sk&f 62698

19. (2,3-dichloro-4-(2-thienylcarbonyl)phenoxy)acetic Acid

20. Chebi:9590

21. Chembl267744

22. 4-(2-theonyl)-2,3-dichlorphenoxyessigsaeure

23. Anp 362

24. Acetic Acid, (2,3-dichloro-4-(2-thienylcarbonyl)phenoxy)-

25. Hc95205sy4

26. Ticrynafen (usan)

27. Tienilic Acid (inn)

28. Ncgc00159454-02

29. Ncgc00159454-03

30. Acetic Acid, [2,3-dichloro-4-(2-thienylcarbonyl)phenoxy]-

31. Dsstox_cid_3670

32. Dsstox_rid_77137

33. Dsstox_gsid_23670

34. Tienilico Acido [spanish]

35. Acide Tienilique [inn-french]

36. Acido Tienilico [inn-spanish]

37. Acidum Tienilicum [inn-latin]

38. Tienilico Acido

39. 2-{2,3-dichloro-4-[(thiophen-2-yl)carbonyl]phenoxy}acetic Acid

40. Anp 3624

41. Skf 62698

42. Cas-40180-04-9

43. Ccris 5489

44. Einecs 254-826-3

45. Ce 3624

46. Fr 3068

47. Brn 1260086

48. Ticrynafan

49. {[2,3-dichloro-4-(2-thienylcarbonyl)phenyl]oxy}acetic Acid

50. 4-(2-theonyl)-2,3-dichlorphenoxyessigsaeure [german]

51. Tienilic-acid

52. Unii-hc95205sy4

53. Selacryn (tn)

54. Ticrynafen [mi]

55. Ticrynafen, Tienilic Acid

56. 5-18-02-00008 (beilstein Handbook Reference)

57. Schembl123608

58. Tienilic Acid [mart.]

59. Zinc2166

60. Tienilic Acid [who-dd]

61. Dtxsid4023670

62. Hms3650c20

63. Tienilic Acid, >=98% (hplc)

64. Tox21_111681

65. Tox21_111682

66. Bdbm50090674

67. Mfcd00867339

68. Akos000280732

69. Db04831

70. Sk&f-62698

71. Ncgc00159454-04

72. Ncgc00159454-09

73. Da-20731

74. Hy-21065

75. Cs-0012688

76. Ft-0675229

77. D02386

78. 7z-0042

79. Sr-00000000556

80. Q7801054

81. Sr-00000000556-2

82. Brd-k34098590-001-01-3

83. 2,3-dichloro-4-(2-thienylcarbonyl)-phenoxyacetic Acid

84. [2,3-dichloro-4-(thiophene-2-carbonyl)-phenoxy]-acetic Acid

85. [2,3-dichloro-4-(thiophene-2-carbonyl)-phenoxyl]-acetic Acid

86. 2-(2,3-dichloro-4-(thiophene-2-carbonyl)phenoxy)aceticacid

87. [2,3-dichloro-4-(thiophene-2-carbonyl)-phenoxy]-acetic Acid(ticrynafen)

88. [2,3-dichloro-4-(thiophene-2-carbonyl)-phenoxy]-acetic Acid(tienilic Acid)

89. [2,3-dichloro-4-(thiophene-2-carbonyl)-phenoxy]-acetic Acid (tienilic Acid)

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₁₃H₈Cl₂O₄S
Molecular Weight	331.2 g/mol
XLogP3	4.1
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	5
Exact Mass	329.9520353 g/mol
Monoisotopic Mass	329.9520353 g/mol
Topological Polar Surface Area	91.8 Å²
Heavy Atom Count	20
Formal Charge	0
Complexity	379
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

For the treatment of hypertension.

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Antihypertensive Agents

Drugs used in the treatment of acute or chronic vascular HYPERTENSION regardless of pharmacological mechanism. Among the antihypertensive agents are DIURETICS; (especially DIURETICS, THIAZIDE); ADRENERGIC BETA-ANTAGONISTS; ADRENERGIC ALPHA-ANTAGONISTS; ANGIOTENSIN-CONVERTING ENZYME INHIBITORS; CALCIUM CHANNEL BLOCKERS; GANGLIONIC BLOCKERS; and VASODILATOR AGENTS. (See all compounds classified as Antihypertensive Agents.)

Uricosuric Agents

Gout suppressants that act directly on the renal tubule to increase the excretion of uric acid, thus reducing its concentrations in plasma. (See all compounds classified as Uricosuric Agents.)

Diuretics

Agents that promote the excretion of urine through their effects on kidney function. (See all compounds classified as Diuretics.)

5.2 ATC Code

C - Cardiovascular system

C03 - Diuretics

C03C - High-ceiling diuretics

C03CC - Aryloxyacetic acid derivatives

C03CC02 - Tienilic acid

5.3 Metabolism/Metabolites

Ticrynafen has known human metabolites that include Thiophene-4,5-epoxide and Tienilic acid-s-oxide.

S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560

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