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DSSTox_CID_2922
Also known as: Diclofenamide, 120-97-8, 4,5-dichlorobenzene-1,3-disulfonamide, Dichlofenamide, Dichlorophenamide, Daranide
Molecular Formula
C6H6Cl2N2O4S2
Molecular Weight
305.2  g/mol
InChI Key
GJQPMPFPNINLKP-UHFFFAOYSA-N
FDA UNII
VVJ6673MHY

A carbonic anhydrase inhibitor that is used in the treatment of glaucoma.
Dichlorphenamide is a Carbonic Anhydrase Inhibitor. The mechanism of action of dichlorphenamide is as a Carbonic Anhydrase Inhibitor.
1 2D Structure

DSSTox_CID_2922

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
4,5-dichlorobenzene-1,3-disulfonamide
2.1.2 InChI
InChI=1S/C6H6Cl2N2O4S2/c7-4-1-3(15(9,11)12)2-5(6(4)8)16(10,13)14/h1-2H,(H2,9,11,12)(H2,10,13,14)
2.1.3 InChI Key
GJQPMPFPNINLKP-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C1=C(C=C(C(=C1S(=O)(=O)N)Cl)Cl)S(=O)(=O)N
2.2 Other Identifiers
2.2.1 UNII
VVJ6673MHY
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Daranide

2. Dichlofenamide

3. Diclofenamid

4. Glauconide

2.3.2 Depositor-Supplied Synonyms

1. Diclofenamide

2. 120-97-8

3. 4,5-dichlorobenzene-1,3-disulfonamide

4. Dichlofenamide

5. Dichlorophenamide

6. Daranide

7. Antidrasi

8. Dichlorphenamid

9. Glauconide

10. Glaucol

11. Oratrol

12. 1,3-benzenedisulfonamide, 4,5-dichloro-

13. 4,5-dichloro-m-benzenedisulfonamide

14. Diclofenamida

15. Diclofenamidum

16. 1,3-disulfamyl-4,5-dichlorobenzene

17. Diclofenamidum [inn-latin]

18. 1,3-disulfamoyl-4,5-dichlorobenzene

19. 4,5-dichloro-1,3-disulfamoylbenzene

20. Diclofenamida [inn-spanish]

21. 3,4-dichloro-5-sulfamylbenzenesulfonamide

22. Keveyis

23. 4,5-dichloro-1,3-benzenedisulfonamide

24. Cb 8000

25. M-benzenedisulfonamide, 4,5-dichloro-

26. Diclofenamide [inn]

27. Dichlorphenamide (usp)

28. Dichlorphenamide [usp]

29. Chembl17

30. Diclofenamid

31. Vvj6673mhy

32. Barastonin

33. Dichlorphenamide (diclofenamide)

34. Glajust

35. Glaumid

36. Glafco

37. Chebi:101085

38. 4,5-dichloro-benzene-1,3-disulfonic Acid Diamide

39. Ncgc00016371-01

40. Cas-120-97-8

41. Dasanide

42. Daranide (tn)

43. Hsdb 3267

44. 120d978

45. Dichlorophenamide (dcp)

46. Einecs 204-440-6

47. Unii-vvj6673mhy

48. Brn 2703329

49. Diclorfenamida

50. Diclorfenammide

51. Sulfonamide 4

52. 2pou

53. 4,5-dichloro-m-benzendisulfonamide

54. Keveyis (tn)

55. Prestwick_1071

56. Dichlorophenamide, Dcp

57. Prestwick0_000809

58. Prestwick1_000809

59. Prestwick2_000809

60. Prestwick3_000809

61. Diclofenamide (jan/inn)

62. Dsstox_cid_2922

63. Diclofenamide [jan]

64. Dsstox_rid_76789

65. Dsstox_gsid_22922

66. Bspbio_000677

67. Dichlorphenamide [mi]

68. Mls002154010

69. Diclofenamide [mart.]

70. Schembl112376

71. Spbio_002598

72. Dichlorphenamide [hsdb]

73. Diclofenamide [who-dd]

74. Bpbio1_000745

75. Gtpl6807

76. Dtxsid1022922

77. Bdbm10883

78. Amy7513

79. Dichlorphenamide [usp-rs]

80. Hms1570b19

81. Hms2097b19

82. Hms2236i07

83. Hms3373g04

84. Hms3655h06

85. Hms3714b19

86. Hms3745k19

87. Zinc896918

88. Bcp22591

89. Ex-a1311

90. Hy-b0397

91. Tox21_110401

92. Mfcd00148948

93. S2177

94. 4,5-dichlorobenzene1,3-disulfonamide

95. Dichlorphenamide [orange Book]

96. Akos015899860

97. Ccg-220809

98. Db01144

99. Dichlorphenamide [usp Impurity]

100. 4,5-dicholorobenzene-1,3-disulfonamide

101. Dichlorphenamide [usp Monograph]

102. Ncgc00016371-02

103. Ncgc00016371-04

104. Ncgc00016371-05

105. Ncgc00016371-06

106. Ncgc00016371-08

107. Ac-25007

108. As-63955

109. I7a

110. Smr001233338

111. 4,5-dichloro-1,3-benzenedisulfonamide #

112. Ft-0648264

113. Sw197138-3

114. A21072

115. C07459

116. D00518

117. Sr-01000841825

118. Q3706987

119. Sr-01000841825-2

120. W-108466

121. Brd-k71499074-001-03-8

122. Dichlorphenamide, United States Pharmacopeia (usp) Reference Standard

123. Diclofenamide; Dichlofenamide; Daranide; 4,5-dichlorobenzene-1,3-disulfonamide

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 305.2 g/mol
Molecular Formula C6H6Cl2N2O4S2
XLogP30.3
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count6
Rotatable Bond Count2
Exact Mass303.9146044 g/mol
Monoisotopic Mass303.9146044 g/mol
Topological Polar Surface Area137 Ų
Heavy Atom Count16
Formal Charge0
Complexity452
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Therapeutic Uses

Carbonic Anhydrase Inhibitors

National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)


...USED IN TREATMENT OF PRIMARY GLAUCOMA, ACUTE PHASE OF SECONDARY GLAUCOMA, & IN PREOPERATIVE CONTROL OF INTRAOCULAR TENSION. ... ALTHOUGH IT HAS DIURETIC PROPERTIES, IT IS NOT PROMOTED FOR THIS PURPOSE.

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 866


...DRUG HAS BEEN FOUND TO INHIBIT EPILEPTIC SEIZURES & TO DECR RATE OF SPINAL FLUID FORMATION. /ACETAZOLAMIDE/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 827


...REDUCES RATE OF AQ HUMOR FORMATION; INTRAOCULAR PRESSURE IN PT WITH GLAUCOMA IS CORRESPONDINGLY REDUCED. THIS ACTION OF DRUG APPEARS TO BE INDEPENDENT OF SYSTEMIC ACID-BASE BALANCE. /ACETAZOLAMIDE/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 827


For more Therapeutic Uses (Complete) data for DICHLORPHENAMIDE (11 total), please visit the HSDB record page.


4.2 Drug Warning

IT HAS BEEN SUGGESTED THAT POSTOPERATIVE USE /AFTER IRIDECTOMY/...MAY ADVERSELY AFFECT OUTCOME OF FILTERING OPERATIONS BY REDUCING SIZE OF RESULTANT DRAINAGE BLEB & DELAYING REFORMATION OF ANTERIOR CHAMBER. /CARBONIC ANHYDRASE INHIBITORS/

American Medical Association, AMA Department of Drugs, AMA Drug Evaluations. 3rd ed. Littleton, Massachusetts: PSG Publishing Co., Inc., 1977., p. 933


...SHOULD BE USED CAUTIOUSLY IN PT WITH OBSTRUCTIVE PULMONARY DISEASE BECAUSE THEY MAY PPT ACUTE RESPIRATORY FAILURE. /CARBONIC ANHYDRASE INHIBITORS/

American Medical Association, AMA Department of Drugs, AMA Drug Evaluations. 3rd ed. Littleton, Massachusetts: PSG Publishing Co., Inc., 1977., p. 933


DIURESIS MAY BE TROUBLESOME INITIALLY BUT SUBSIDES DURING CONTINUED THERAPY BECAUSE OF PERSISTENT METABOLIC ACIDOSIS. /CARBONIC ANHYDRASE INHIBITORS/

American Medical Association, AMA Department of Drugs, AMA Drug Evaluations. 3rd ed. Littleton, Massachusetts: PSG Publishing Co., Inc., 1977., p. 932


...BE GIVEN CAUTIOUSLY TO PT...WITH DISEASES ASSOC WITH INCR MINERALOCORTICOID ACTIVITY (EG, PRIMARY HYPERALDOSTERONISM, CUSHING'S SYNDROME) & THOSE RECEIVING POTASSIUM-WASTING DRUGS (EG, THIAZIDES, LOOP DIURETICS, CORTICOSTEROIDS). /CARBONIC ANHYDRASE INHIBITORS/

American Medical Association, AMA Department of Drugs, AMA Drug Evaluations. 3rd ed. Littleton, Massachusetts: PSG Publishing Co., Inc., 1977., p. 933


For more Drug Warnings (Complete) data for DICHLORPHENAMIDE (7 total), please visit the HSDB record page.


4.3 Drug Indication

For adjunctive treatment of: chronic simple (open-angle) glaucoma, secondary glaucoma, and preoperatively in acute angle-closure glaucoma where delay of surgery is desired in order to lower intraocular pressure


5 Pharmacology and Biochemistry
5.1 Pharmacology

Dichlorphenamide is an oral carbonic anhydrase inhibitor indicated for adjunctive treatment of: chronic simple (open-angle) glaucoma, secondary glaucoma, and preoperatively in acute angle-closure glaucoma where delay of surgery is desired in order to lower intraocular pressure. Carbonic anhydrase inhibitors reduce intraocular pressure by partially suppressing the secretion of aqueous humor (inflow).


5.2 MeSH Pharmacological Classification

Carbonic Anhydrase Inhibitors

A class of compounds that reduces the secretion of H+ ions by the proximal kidney tubule through inhibition of CARBONIC ANHYDRASES. (See all compounds classified as Carbonic Anhydrase Inhibitors.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
DICHLORPHENAMIDE
5.3.2 FDA UNII
VVJ6673MHY
5.3.3 Pharmacological Classes
Carbonic Anhydrase Inhibitors [MoA]; Sulfonamides [CS]; Carbonic Anhydrase Inhibitor [EPC]
5.4 ATC Code

S - Sensory organs

S01 - Ophthalmologicals

S01E - Antiglaucoma preparations and miotics

S01EC - Carbonic anhydrase inhibitors

S01EC02 - Diclofenamide


5.5 Mechanism of Action

Carbonic anhydrase inhibitors reduce intraocular pressure by partially suppressing the secretion of aqueous humor (inflow), although the mechanism by which they do this is not fully understood. Evidence suggests that HCO3- ions are produced in the ciliary body by hydration of carbon dioxide under the influence of carbonic anhydrase and diffuse into the posterior chamber which contains more Na+ and HCO3- ions than does plasma and consequently is hypertonic. Water is then attracted to the posterior chamber by osmosis, resulting in a drop in pressure.


PHOSPHATURIA MAY BE RELATED TO DIRECT STIMULATION...OF CYCLIC ADENOSINE 3',5'-MONOPHOSPHATE...PRODN BY KIDNEY. ...DRUG ACTS SIMILARLY TO PARATHYROID HORMONE IN ENHANCING URINARY EXCRETION OF PHOSPHATE & CYCLIC AMP, IN CONTRAST TO ITS ANTAGONISM OF ACTION OF HORMONE ON BONE. /ACETAZOLAMIDE/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 826


...INHIBITION OF...CARBONIC ANHYDRASE. ...IS NONCOMPETITIVE. ...ENZYME IS NORMALLY PRESENT IN TISSUES IN HUGE EXCESS. MORE THAN 99% OF ENZYME ACTIVITY IN KIDNEY MUST BE INHIBITED BEFORE PHYSIOLOGICAL EFFECTS BECOME APPARENT. ENZYME...IS DOMINANT TISSUE COMPONENT TO WHICH INHIBITORS BECOME BOUND. /ACETAZOLAMIDE/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 826


/CHANGES IN URINE/...MAY BE ATTRIBUTED TO INHIBITION OF (+)H SECRETION BY RENAL TUBULE. ... CURRENT EVIDENCE INDICATES GREATER EFFECT ON PROXIMAL THAN ON DISTAL TUBULE, WITH LITTLE OR NO EFFECT ON ASCENDING LIMB. ...PHOSPHATURIA...USED AS INDEX OF LOCALIZING DIURETIC ACTION... /ACETAZOLAMIDE/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 826


...INCR URINARY EXCRETION OF BICARBONATE & FIXED CATION, MOSTLY SODIUM. AS RESULT, CONCN OF BICARBONATE IN EXTRACELLULAR FLUID DECR & METABOLIC ACIDOSIS RESULTS. ...RENAL RESPONSE TO ACETAZOLAMIDE IS GREATLY REDUCED.../BUT/ DIURETIC RESPONSE IS ENHANCED. /ACETAZOLAMIDE/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 826


DRUG LOWERS INTRAOCULAR PRESSURE BY REDUCING RATE OF SECRETION OF AQ HUMOR.

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 867


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