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    Chemistry

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    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
    Dichlorphenamide
    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

    Dichlorphenamide

    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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    [{"dataSource":"API Import","activeIngredients":"DICHLORPHENAMIDE","year":"2021","qtr":"Q2","strtotime":1620585000,"product":"KEVEYIS (DICHLORPHENAMIDE) TABLETS, 50 MG - 100 COUNTS NDC71O9O-001-01 LOT# 322206, ( 100 TABLETS )(FORRESEARCH USE ONLY","address":"","city":"","supplier":"NOVITIUM PHARMA LLC","supplierCountry":"UNITED STATES","foreign_port":"NEW YORK - JOHN F. K","customer":"SCITUS PHARMA SERVICES ","customerCountry":"INDIA","quantity":"0.20","actualQuantity":"0.2","unit":"KGS","unitRateFc":"10000","totalValueFC":"2041","currency":"USD","unitRateINR":"747500","date":"10-May-2021","totalValueINR":"149500","totalValueInUsd":"2041","indian_port":"MADRAS AIR","hs_no":"29372900","bill_no":"3888820","productDescription":"API","marketType":"REGULATED MARKET","country":"UNITED STATES","selfForZScoreResived":"Pharma Grade","supplierPort":"NEW YORK - JOHN F. K","supplierAddress":"","customerAddress":""}]
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