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    Benzothiazide

    ACTIVE PHARMA INGREDIENTS

    FINISHED DOSAGE FORMULATIONS

    PharmaCompass
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    2D Structure
    Also known as: 91-33-8, Benzothiazide, Aquatag, Dihydrex, Lemazide, Fovane
    Molecular Formula
    C15H14ClN3O4S3
    Molecular Weight
    431.9  g/mol
    InChI Key
    NDTSRXAMMQDVSW-UHFFFAOYSA-N
    FDA UNII
    1TD8J48L61
    Benzthiazide is an intermediate acting agent belonging to the class of thiazide diuretics. Benzthiazide, also known as benzothiazide, is no longer commercially available in the United States.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    3-(benzylsulfanylmethyl)-6-chloro-1,1-dioxo-4H-16,2,4-benzothiadiazine-7-sulfonamide
    2.1.2 InChI
    InChI=1S/C15H14ClN3O4S3/c16-11-6-12-14(7-13(11)25(17,20)21)26(22,23)19-15(18-12)9-24-8-10-4-2-1-3-5-10/h1-7H,8-9H2,(H,18,19)(H2,17,20,21)
    2.1.3 InChI Key
    NDTSRXAMMQDVSW-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    C1=CC=C(C=C1)CSCC2=NS(=O)(=O)C3=CC(=C(C=C3N2)Cl)S(=O)(=O)N
    2.2 Other Identifiers
    2.2.1 UNII
    1TD8J48L61
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Benzothiazide

    2.3.2 Depositor-Supplied Synonyms

    1. 91-33-8

    2. Benzothiazide

    3. Aquatag

    4. Dihydrex

    5. Lemazide

    6. Fovane

    7. Exna

    8. Urese

    9. Freeuril

    10. Diucen

    11. Edemex

    12. Exosalt

    13. Proaqua

    14. Diucene

    15. Regulon

    16. Pfizer 1393

    17. Benzotiazida

    18. Benzthiazidum

    19. 3-benzylthiomethyl-6-chloro-7-sulfamoyl-1,2,4-benzothiadiazine 1,1-dioxide

    20. P 1393

    21. 3-((benzylthio)methyl)-6-chloro-7-sulfamoyl-2h-benzo-1,2,4-thiadiazine 1,1-dioxide

    22. 6-chloro-7-sulfamoyl-3-benzylthiomethyl-2h-1,2,4-benzothiadiazine 1,1-dioxide

    23. Nsc-755902

    24. 2h-1,2,4-benzothiadiazine-7-sulfonamide, 3-((benzylthio)methyl)-6-chloro-, 1,1-dioxide

    25. 2h-1,2,4-benzothiadiazine-7-sulfonamide, 6-chloro-3-(((phenylmethyl)thio)methyl)-, 1,1-dioxide

    26. 2h-1,2,4-benzothiadiazine-7-sulfonamide, 6-chloro-3-[[(phenylmethyl)thio]methyl]-, 1,1-dioxide

    27. 3-((benzylthio)methyl)-6-chloro-2h-1,2,4-benzothiadiazine-7-sulfonamide 1,1-dioxide

    28. Mls000069562

    29. Chebi:3047

    30. Aquapres

    31. Aquasec

    32. Urazide

    33. Fouane

    34. 1td8j48l61

    35. Hy-drine

    36. Pro-aqua

    37. Aqua-scrip

    38. Rid-ema

    39. 3-benzylthiomethyl-6-chloro-2h-1,2,4-benzothiadiazine-7-sulfonamide 1,1-dioxide

    40. 6-chloro-3-(((phenylmethyl)thio)methyl)-2h-1,2,4-benzothiadiazine-7-sulfonamide 1,1-dioxide

    41. S-aqua

    42. Cas-91-33-8

    43. Ncgc00016347-01

    44. Benztiazide

    45. Benztiazide [dcit]

    46. Smr000058805

    47. Hydrine

    48. Dsstox_cid_2658

    49. 6-chloro-1,1-dioxo-3-(phenylmethylsulfanylmethyl)-4h-benzo[e][1,2,4]thiadiazine-7-sulfonamide

    50. Dsstox_rid_76677

    51. Dsstox_gsid_22658

    52. Benzthiazidum [inn-latin]

    53. Benzotiazida [inn-spanish]

    54. 6-chloro-3-{[(phenylmethyl)thio]methyl}-2h-1,2,4-benzothiadiazine-7-sulfonamide 1,1-dioxide

    55. Benzthazide; 3-[(benzylsulfanyl)methyl]-6-chloro-4h-1,2,4-benzothiadiazine-7-sulfonamide 1,1-dioxide

    56. Exna (tn)

    57. Hsdb 3296

    58. Sr-05000001574

    59. Benzthiazide (jan/inn)

    60. Einecs 202-061-0

    61. Unii-1td8j48l61

    62. 3-(benzylsulfanylmethyl)-6-chloro-1,1-dioxo-2h-1?^{6},2,4-benzothiadiazine-7-sulfonamide

    63. Benzthiazide [usp:inn:ban:jan]

    64. Prestwick_993

    65. Benzthiazide-anhydrate

    66. 3-((benzylthio)methyl)-6-chloro-2h-1,2,4-benzothiadiazine-7-sulfonamide1,1-dioxide

    67. Spectrum_000076

    68. Opera_id_1644

    69. Prestwick0_000824

    70. Prestwick1_000824

    71. Prestwick2_000824

    72. Prestwick3_000824

    73. Spectrum2_001141

    74. Spectrum3_000315

    75. Spectrum4_000250

    76. Spectrum5_000882

    77. Benzthiazide [mi]

    78. Benzthiazide [inn]

    79. Benzthiazide [jan]

    80. Benzthiazide [hsdb]

    81. 2h-1,2,4-benzothiadiazine-7-sulfonamide, 3-((benzylthio)menthyl)-6-chloro-, 1,1-dioxide

    82. 3-((benzylthio)methyl)-6-chloro-7-sulfamoyl-2h-benzo-1,2,4-thiadiazine-1,1-dioxide

    83. Benzthiazide [vandf]

    84. Schembl26257

    85. Benzthiazide [mart.]

    86. Bspbio_000747

    87. Bspbio_001910

    88. Kbiogr_000660

    89. Kbioss_000476

    90. Benzthiazide [who-dd]

    91. Divk1c_000491

    92. Spectrum1500141

    93. Spbio_001061

    94. Spbio_002668

    95. Bpbio1_000823

    96. Gtpl7125

    97. Chembl1201039

    98. Dtxsid4022658

    99. Hms501i13

    100. Kbio1_000491

    101. Kbio2_000476

    102. Kbio2_003044

    103. Kbio2_005612

    104. Kbio3_001410

    105. Ninds_000491

    106. Benzthiazide [orange Book]

    107. Hms1570f09

    108. Hms1920g11

    109. Hms2091m13

    110. Hms2097f09

    111. Hms2234j10

    112. Hms3370l07

    113. Hms3714f09

    114. Pharmakon1600-01500141

    115. Hy-b1424

    116. Zinc3871698

    117. Tox21_110387

    118. Ccg-40326

    119. Nsc755902

    120. Akos015889538

    121. Tox21_110387_1

    122. Db00562

    123. Nsc 755902

    124. 3-[(benzylsulfanyl)methyl]-6-chloro-2h-1,2,4-benzothiadiazine-7-sulfonamide 1,1-dioxide

    125. Idi1_000491

    126. Ncgc00016347-02

    127. Ncgc00016347-03

    128. Ncgc00016347-04

    129. Ncgc00016347-07

    130. Ncgc00094599-01

    131. Ncgc00094599-02

    132. As-56353

    133. Sbi-0051294.p003

    134. Cs-0013136

    135. Ft-0622764

    136. Sw197075-3

    137. C07759

    138. D00651

    139. D93059

    140. Ab00051924_04

    141. Ab00051924_05

    142. Q2889971

    143. Sr-05000001574-1

    144. Sr-05000001574-2

    145. Brd-k21450440-001-05-4

    146. Brd-k21450440-001-08-8

    147. Z1692496506

    148. 3-((benzylthio)methyl)-6-chloro-1,2,4-benzothiadiazine-7-sulfonamide 1,1-dioxide

    149. 3-((benzylthio)methyl)-6-chloro-4h-benzo[e][1,2,4]thiadiazine-7-sulfonamide 1,1-dioxide

    150. 3-(benzylsulfanylmethyl)-6-chloro-1,1-dioxo-4h-1$l^{6},2,4-benzothiadiazine-7-sulfonamide

    151. 3-(benzylsulfanylmethyl)-6-chloro-1,1-dioxo-4h-1lambda6,2,4-benzothiadiazine-7-sulfonamide

    152. 3-[(benzylsulfanyl)methyl]-6-chloro-2h-1,2,4-benzothiadiazine-7-sulfonamide 1,1-dioxide #

    153. 2h-1,2,4-benzothiadiazine-7-sulfonamide, 6-chloro-3-(((phenylmethyl)thio)methyl)-, Dioxide-1,1-

    154. 3-[(benzylsulfanyl)methyl]-6-chloro-1,1-dioxo-2h-1lambda6,2,4-benzothiadiazine-7-sulfonamide

    155. 3-[(benzylsulfanyl)methyl]-6-chloro-1,1-dioxo-4h-1$l^{6},2,4-benzothiadiazine-7-sulfonamide

    156. 6-chloro-3[[(phenylmethyl)thio]ethyl]4h-1,2,4-benzthothiadiazine- 7-sulfonamide-1,1-dioxide

    2.4 Create Date
    2005-03-25
    3 Chemical and Physical Properties
    Molecular Weight 431.9 g/mol
    Molecular Formula C15H14ClN3O4S3
    XLogP31.7
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count7
    Rotatable Bond Count5
    Exact Mass430.9834972 g/mol
    Monoisotopic Mass430.9834972 g/mol
    Topological Polar Surface Area161 Ų
    Heavy Atom Count26
    Formal Charge0
    Complexity739
    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

    Diuretics, Thiazide

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

    IT IS ABOUT 10 TIMES AS POTENT ON MG BASIS AS CHLOROTHIAZIDE.

    Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 869

    THIAZIDE DRUGS...USUALLY FIRST DRUG TO BE EMPLOYED IN TREATMENT OF HYPERTENSION. SINCE THIAZIDES INDUCE ONLY LIMITED (10%) REDN IN BLOOD PRESSURE THEY ARE USEFUL EITHER IN MILD CASES OF HYPERTENSION OR AS ADJUNCTIVE THERAPY TO OTHER DRUGS. /THIAZIDE DIURETICS/

    Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 868

    THIAZIDE DIURETICS ARE EFFECTIVE AS ADJUNCTIVE THERAPY IN EDEMA ASSOC WITH CONGESTIVE HEART FAILURE, HEPATIC CIRRHOSIS, & CORTICOSTEROID & ESTROGEN THERAPY, AS WELL AS EDEMA DUE TO VARIOUS FORMS OF RENAL DYSFUNCTION...& SEVERE EDEMA DUE TO PREGNANCY. /THIAZIDE DIURETICS/

    Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 868

    For more Therapeutic Uses (Complete) data for BENZTHIAZIDE (8 total), please visit the HSDB record page.

    4.2 Drug Warning

    THEY SHOULD...BE USED WITH CAUTION IN PT WITH IMPAIRED LIVER FUNCTION. /THIAZIDE DIURETICS/

    Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 868

    PERIODIC SERUM ELECTROLYTE DETERMINATION SHOULD BE DONE ON ALL PATIENTS IN ORDER TO DETECT ELECTROLYTE IMBALANCE SUCH AS HYPONATREMIA, HYPOCHLOREMIC ALKALOSIS, & HYPOKALEMIA. /THIAZIDE DIURETICS/

    Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 868

    THIAZIDE DIURETICS ARE CONTRAINDICATED IN ANURIA, PATIENTS HYPERSENSITIVE TO THESE & OTHER SULFONAMIDE DRUGS, & IN OTHERWISE HEALTHY PREGNANT WOMEN WITH OR WITHOUT MILD EDEMA. ...SHOULD BE USED WITH CAUTION IN PT WITH RENAL DISEASE, SINCE THEY MAY PPT AZOTEMIA. /THIAZIDE DIURETICS/

    Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 868

    CLINICAL TOXICITY...USUALLY RESULTS FROM UNEXPECTED HYPERSENSITIVITY. CASES OF...PURPURA, DERMATITIS WITH PHOTOSENSITIVITY, DEPRESSION OF FORMED ELEMENTS OF BLOOD, & NECROTIZING VASCULITIS HAVE BEEN REPORTED. /THIAZIDE DIURETICS/

    Gilman, A. G., L. S. Goodman, and A. Gilman. (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 6th ed. New York: Macmillan Publishing Co., Inc. 1980., p. 902

    For more Drug Warnings (Complete) data for BENZTHIAZIDE (8 total), please visit the HSDB record page.

    4.3 Minimum/Potential Fatal Human Dose

    3. 3= MODERATELY TOXIC: PROBABLE ORAL LETHAL DOSE (HUMAN) 0.5-5 G/KG, BETWEEN 1 OZ & 1 PINT FOR 70 KG PERSON (150 LB). /BENZOTHIADIAZIDE DIURETICS/

    Gosselin, R.E., H.C. Hodge, R.P. Smith, and M.N. Gleason. Clinical Toxicology of Commercial Products. 4th ed. Baltimore: Williams and Wilkins, 1976., p. II-239

    4.4 Drug Indication

    For the treatment of high blood pressure and management of edema.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Benzthiazide is used to treat hypertension and edema. Like other thiazides, benzthiazide promotes water loss from the body (diuretics). They inhibit Na+/Cl- reabsorption from the distal convoluted tubules in the kidneys. Thiazides also cause loss of potassium and an increase in serum uric acid. Thiazides are often used to treat hypertension, but their hypotensive effects are not necessarily due to their diuretic activity. Thiazides have been shown to prevent hypertension-related morbidity and mortality although the mechanism is not fully understood. Thiazides cause vasodilation by activating calcium-activated potassium channels (large conductance) in vascular smooth muscles and inhibiting various carbonic anhydrases in vascular tissue.

    5.2 Absorption, Distribution and Excretion

    Absorption

    Absorbed in the digestive tract.

    DIURESIS OCCURS WITHIN 2 HR & LASTS 12-18 HR.

    Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 869

    THIAZIDES ARE ABSORBED FROM GI TRACT & OWE THEIR USEFULNESS LARGELY TO THEIR EFFECTIVENESS BY ORAL ROUTE. ABSORPTION IS RELATIVELY RAPID. MOST AGENTS SHOW DEMONSTRABLE DIURETIC EFFECT WITHIN HR AFTER ORAL ADMIN. /THIAZIDE DIURETICS/

    Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 831

    IN GENERAL, THIAZIDES WITH RELATIVELY LONG DURATIONS OF ACTION SHOW PROPORTIONATELY HIGH DEGREE OF BINDING TO PLASMA PROTEINS & ARE REABSORBED BY RENAL TUBULES. ... DRUG PASSES READILY THROUGH PLACENTAL BARRIER TO FETUS. ALL THIAZIDES PROBABLY UNDERGO ACTIVE SECRETION IN PROXIMAL TUBULE. /THIAZIDE DIURETICS/

    Gilman, A. G., L. S. Goodman, and A. Gilman. (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 6th ed. New York: Macmillan Publishing Co., Inc. 1980., p. 902

    DISTRIBUTED IN EXTRACELLULAR SPACE & /CROSSES/ PLACENTA /& APPEARS IN CORD BLOOD/. ONSET OF DIURETIC ACTION...2 HR...PEAK EFFECT...3 TO 6 HR...APPROX DURATION OF /ACTION OF SINGLE DOSE 12-18 HR/. EXCRETED BY GLOMERULAR FILTRATION & ACTIVE SECRETION IN PROXIMAL TUBULE /HUMAN, ORAL/.

    American Society of Hospital Pharmacists. Data supplied on contract from American Hospital Formulary Service and other current ASHP sources., p. 1975

    ONSET OF HYPOTENSIVE ACTION...3 TO 4 DAYS, &...ACTION DISSIPATES...1ST WK AFTER DISCONTINUING CHRONIC THERAPY. /APPEARS/ IN MILK OF NURSING MOTHERS /HUMAN, ORAL/.

    American Society of Hospital Pharmacists. Data supplied on contract from American Hospital Formulary Service and other current ASHP sources., p. 1975

    5.3 Mechanism of Action

    As a diuretic, benzthiazide inhibits active chloride reabsorption at the early distal tubule via the Na-Cl cotransporter, resulting in an increase in the excretion of sodium, chloride, and water. Thiazides like benzthiazide also inhibit sodium ion transport across the renal tubular epithelium through binding to the thiazide sensitive sodium-chloride transporter. This results in an increase in potassium excretion via the sodium-potassium exchange mechanism. The antihypertensive mechanism of benzthiazide is less well understood although it may be mediated through its action on carbonic anhydrases in the smooth muscle or through its action on the large-conductance calcium-activated potassium (KCa) channel, also found in the smooth muscle.

    ...BENZOTHIADIIDIDES HAVE DIRECT EFFECT ON RENAL TUBULAR TRANSPORT OF SODIUM & CHLORIDE...INDEPENDENT OF ANY EFFECT ON CARBONIC ANHYDRASE. /THIAZIDE DIURETICS/

    Gilman, A. G., L. S. Goodman, and A. Gilman. (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 6th ed. New York: Macmillan Publishing Co., Inc. 1980., p. 899

    ...BENEFICIAL EFFECTS /OF THIAZIDES/ APPEAR TO RESULT FROM ALTERED SODIUM BALANCE. ...INITIATION OF TREATMENT...CARDIAC OUTPUT IS DECR & BLOOD VOL... DIMINISHED. ...CHRONIC THERAPY CARDIAC OUTPUT RETURNS TO NORMAL, PERIPHERAL VASCULAR RESISTANCE FALLS &...SMALL REDN IN EXTRACELLULAR WATER & PLASMA VOL. /THIAZIDE DIURETICS/

    Gilman, A. G., L. S. Goodman, and A. Gilman. (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 6th ed. New York: Macmillan Publishing Co., Inc. 1980., p. 803

    /DOMINANT ACTION OF THIAZIDES IS TO INCR/ RENAL EXCRETION OF SODIUM & CHLORIDE & ACCOMPANYING VOL OF WATER. ...VIRTUALLY INDEPENDENT OF ACID-BASE BALANCE. ... EVOKE SIGNIFICANT AUGMENTATION OF POTASSIUM EXCRETION. THEY VARY WIDELY IN THEIR POTENCY AS INHIBITORS OF CARBONIC ANHYDRASE. /THIAZIDE DIURETICS/

    Gilman, A. G., L. S. Goodman, and A. Gilman. (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 6th ed. New York: Macmillan Publishing Co., Inc. 1980., p. 901

    UNILATERAL RENAL INTRA-ARTERIAL INJECTION OF THIAZIDES PRODUCES A UNILATERAL DIURETIC RESPONSE, INDICATING A DIRECT RENAL ACTION. ...THIAZIDES...ACTIVELY SECRETED IN PROXIMAL TUBULE. ... DEPENDING ON THIAZIDE, ITS DOSAGE & SOLUTES MEASURED, ITS ACTION ON ELECTROLYTE TRANSPORT MAY OR MAY NOT BE BLOCKED. /THIAZIDE DIURETICS/

    Gilman, A. G., L. S. Goodman, and A. Gilman. (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 6th ed. New York: Macmillan Publishing Co., Inc. 1980., p. 901

    For more Mechanism of Action (Complete) data for BENZTHIAZIDE (11 total), please visit the HSDB record page.