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    Diazoxide

    ACTIVE PHARMA INGREDIENTS

    DEVELOPMENTS

    FINISHED DOSAGE FORMULATIONS

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    2D Structure
    Also known as: 364-98-7, Proglycem, Hyperstat, Hypertonalum, Eudemine, Proglicem
    Molecular Formula
    C8H7ClN2O2S
    Molecular Weight
    230.67  g/mol
    InChI Key
    GDLBFKVLRPITMI-UHFFFAOYSA-N
    FDA UNII
    O5CB12L4FN
    A benzothiadiazine derivative that is a peripheral vasodilator used for hypertensive emergencies. It lacks diuretic effect, apparently because it lacks a sulfonamide group.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    7-chloro-3-methyl-4H-16,2,4-benzothiadiazine 1,1-dioxide
    2.1.2 InChI
    InChI=1S/C8H7ClN2O2S/c1-5-10-7-3-2-6(9)4-8(7)14(12,13)11-5/h2-4H,1H3,(H,10,11)
    2.1.3 InChI Key
    GDLBFKVLRPITMI-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CC1=NS(=O)(=O)C2=C(N1)C=CC(=C2)Cl
    2.2 Other Identifiers
    2.2.1 UNII
    O5CB12L4FN
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Hyperstat

    2. Proglycem

    2.3.2 Depositor-Supplied Synonyms

    1. 364-98-7

    2. Proglycem

    3. Hyperstat

    4. Hypertonalum

    5. Eudemine

    6. Proglicem

    7. Dizoxide

    8. Mutabase

    9. 7-chloro-3-methyl-2h-1,2,4-benzothiadiazine 1,1-dioxide

    10. Sch 6783

    11. Sch-6783

    12. Diazossido

    13. Diazoxidum

    14. Srg 95213

    15. Srg-95213

    16. Diazoxido

    17. 2h-1,2,4-benzothiadiazine, 7-chloro-3-methyl-, 1,1-dioxide

    18. Eudemine Injection

    19. Nsc-64198

    20. Nsc 76130

    21. Chebi:4495

    22. Mfcd00078578

    23. Nsc-76130

    24. O5cb12l4fn

    25. 3-methyl-7-chloro-1,2,4-benzothiadiazine 1,1-dioxide

    26. Mls000028459

    27. 7-cloro-3-metil-2h-1,2,4-benzotiodiazina-1,1-diossido

    28. 364-98-7 (free)

    29. 7-chloro-3-methyl-4h-1$l^{6},2,4-benzothiadiazine 1,1-dioxide

    30. Diazossido [italian]

    31. Nsc64198

    32. Nsc76130

    33. 7-chloro-3-methyl-2h-1,2,4-benzothiadiazine1,1-dioxide

    34. C8h7cln2o2s

    35. Diazossido [dcit]

    36. Ncgc00015380-09

    37. Cas-364-98-7

    38. Smr000058392

    39. 7-chloro-3-methyl-2h-benzo[e][1,2,4]thiadiazine 1,1-dioxide

    40. Dsstox_cid_2914

    41. Diazoxidum [inn-latin]

    42. Dsstox_rid_76786

    43. Diazoxido [inn-spanish]

    44. Dsstox_gsid_22914

    45. 7-chloro-3-methyl-4h-1,2,4-benzothiadiazine 1,1-dioxide

    46. Aroglycem

    47. 7-chloro-3-methyl-4h-benzo[e][1,2,4]thiadiazine 1,1-dioxide

    48. Hyperstat (tn)

    49. Sr-01000075314

    50. Einecs 206-668-1

    51. Nsc 64198

    52. Unii-o5cb12l4fn

    53. 7-chloro-3-methyl-2h-1,4-benzothiadiazine 1,1-dioxide

    54. Diazoxide (jan/usp/inn)

    55. Eudimine

    56. 2h-1,4-benzothiadiazine, 7-chloro-3-methyl-, 1,1-dioxide

    57. 7-chloro-3-methyl-2h-1?^{6},2,4-benzothiadiazine 1,1-dioxide

    58. 7-cloro-3-metil-2h-1,2,4-benzotiodiazina-1,1-diossido [italian]

    59. Proglycem (tn)

    60. Prestwick_163

    61. Diazoxide [usan:usp:inn:ban:jan]

    62. Tocris-0964

    63. Diazoxide [inn]

    64. Diazoxide [jan]

    65. Opera_id_608

    66. Diazoxide [mi]

    67. Diazoxide [usan]

    68. Prestwick0_000087

    69. Prestwick1_000087

    70. Prestwick2_000087

    71. Prestwick3_000087

    72. Spectrum3_000735

    73. Spectrum4_001248

    74. Diazoxide [vandf]

    75. Lopac-d-9035

    76. Chembl181

    77. Diazoxide [mart.]

    78. D 9035

    79. Diazoxide [usp-rs]

    80. Diazoxide [who-dd]

    81. Diazoxide [who-ip]

    82. Cbiol_001750

    83. Lopac0_000404

    84. Schembl41254

    85. Bspbio_000014

    86. Bspbio_001307

    87. Bspbio_002290

    88. Kbiogr_000027

    89. Kbiogr_001776

    90. Kbioss_000027

    91. Mls001076071

    92. Mls001424164

    93. Spectrum2300206

    94. Spbio_001953

    95. Bpbio1_000016

    96. Gtpl2409

    97. Diazoxide [orange Book]

    98. Chembl1518123

    99. Diazoxide [ep Monograph]

    100. Dtxsid7022914

    101. Bdbm86248

    102. Kbio2_000027

    103. Kbio2_002595

    104. Kbio2_005163

    105. Kbio3_000053

    106. Kbio3_000054

    107. Kbio3_001510

    108. Diazoxide [usp Monograph]

    109. Diazoxidum [who-ip Latin]

    110. Bio1_000036

    111. Bio1_000525

    112. Bio1_001014

    113. Bio2_000027

    114. Bio2_000507

    115. Hms1361b09

    116. Hms1568a16

    117. Hms1791b09

    118. Hms1922l22

    119. Hms1989b09

    120. Hms2051p20

    121. Hms2089l04

    122. Hms2093n12

    123. Hms2095a16

    124. Hms2234b23

    125. Hms3261a10

    126. Hms3267i11

    127. Hms3371l13

    128. Hms3393p20

    129. Hms3402b09

    130. Hms3411l18

    131. Hms3675l18

    132. Hms3712a16

    133. Hms3885h12

    134. Pharmakon1600-02300206

    135. 2h-1,2, 4-benzothiadiazine, 7-chloro-3-methyl-, 1,1-dioxide

    136. 7-chloro-3-methyl-1lambda~4~,2,4-benzothiadiazin-1-ol 1-oxide

    137. 7-chloro-3-methyl-4h-1lambda6,2,4-benzothiadiazine 1,1-dioxide

    138. Bcp26107

    139. Hy-b1140

    140. Nsc_3019

    141. Zinc3872277

    142. Tox21_110132

    143. Tox21_500404

    144. Bdbm50237612

    145. Kc-115

    146. Nsc759574

    147. S4630

    148. Akos015896340

    149. Akos024458715

    150. Tox21_110132_1

    151. Ccg-101062

    152. Ccg-204497

    153. Cs-4745

    154. Db01119

    155. Ks-1444

    156. Lp00404

    157. Nc00312

    158. Nsc-759574

    159. Sdccgsbi-0050390.p002

    160. Idi1_033777

    161. Diazoxide 100 Microg/ml In Acetonitrile

    162. Ncgc00015380-01

    163. Ncgc00015380-02

    164. Ncgc00015380-03

    165. Ncgc00015380-04

    166. Ncgc00015380-05

    167. Ncgc00015380-06

    168. Ncgc00015380-07

    169. Ncgc00015380-08

    170. Ncgc00015380-10

    171. Ncgc00015380-11

    172. Ncgc00015380-12

    173. Ncgc00015380-13

    174. Ncgc00015380-20

    175. Ncgc00022882-03

    176. Ncgc00024907-01

    177. Ncgc00024907-02

    178. Ncgc00024907-03

    179. Ncgc00024907-04

    180. Ncgc00024907-05

    181. Ncgc00024907-06

    182. Ncgc00024907-07

    183. Ncgc00024907-08

    184. Ncgc00261089-01

    185. Cas_364-98-7

    186. Sy066792

    187. Db-048966

    188. B6526

    189. D5402

    190. Eu-0100404

    191. Ft-0603087

    192. Vu0239714-6

    193. C06949

    194. D00294

    195. F12855

    196. 364d987

    197. A823275

    198. Q420009

    199. Sr-01000075314-1

    200. Sr-01000075314-3

    201. Sr-01000075314-4

    202. Sr-01000075314-6

    203. 3-methyl-7-chloro-1,2,4-benzothiadiazine1,1-dioxide

    204. Brd-k73109821-001-05-2

    205. Brd-k73109821-001-10-2

    206. Diazoxide, European Pharmacopoeia (ep) Reference Standard

    207. 4h-1,2,4-benzothiadiazine, 7-chloro-3-methyl-, 1,1-dioxide

    208. 7-chloro-3-methyl-4h-1

    209. E?,2,4-benzothiadiazine-1,1-dione

    210. 7-chloro-3-methyl-4h-1

    211. E6,2,4-benzothiadiazine 1,1-dioxide

    212. Diazoxide, United States Pharmacopeia (usp) Reference Standard

    213. 7-chloro-3-methyl-2h-1$l^{6},2,4-benzothiadiazine 1,1-dioxide

    214. 7-chloro-3-methyl-4h-1$l^{6},2,4-benzothiadiazine-1,1-dione

    2.4 Create Date
    2005-03-25
    3 Chemical and Physical Properties
    Molecular Weight 230.67 g/mol
    Molecular Formula C8H7ClN2O2S
    XLogP31.2
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count3
    Rotatable Bond Count0
    Exact Mass229.9916763 g/mol
    Monoisotopic Mass229.9916763 g/mol
    Topological Polar Surface Area66.9 Ų
    Heavy Atom Count14
    Formal Charge0
    Complexity360
    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 Drug Information
    1 of 2  
    Drug NameProglycem
    PubMed HealthDiazoxide (By mouth)
    Drug ClassesGastrointestinal Agent, Glucose Regulation, Antihypoglycemic
    Drug LabelPROGLYCEM (diazoxide) is a nondiuretic benzothiadiazine derivative taken orally for the management of symptomatic hypoglycemia. PROGLYCEM Capsules contain 50 mg diazoxide, USP. The Suspension contains 50 mg of diazoxide, USP in each milliliter an...
    Active IngredientDiazoxide
    Dosage FormSuspension
    RouteOral
    Strength50mg/ml
    Market StatusPrescription
    CompanyTeva Branded Pharm

    2 of 2  
    Drug NameProglycem
    PubMed HealthDiazoxide (By mouth)
    Drug ClassesGastrointestinal Agent, Glucose Regulation, Antihypoglycemic
    Drug LabelPROGLYCEM (diazoxide) is a nondiuretic benzothiadiazine derivative taken orally for the management of symptomatic hypoglycemia. PROGLYCEM Capsules contain 50 mg diazoxide, USP. The Suspension contains 50 mg of diazoxide, USP in each milliliter an...
    Active IngredientDiazoxide
    Dosage FormSuspension
    RouteOral
    Strength50mg/ml
    Market StatusPrescription
    CompanyTeva Branded Pharm

    4.2 Drug Indication

    Used parentally to treat hypertensive emergencies. Also used to treat hypoglycemia secondary to insulinoma.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Diazoxide is a potassium channel activator. Its mechanism of action revolves around enhancing cell membrane permeability to potassium ions. This action consequently elicits the relaxation of local smooth muscles. This switches off voltage-gated calcium ion channels which inhibits the generation of an action potential.

    5.2 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.)

    Vasodilator Agents

    Drugs used to cause dilation of the blood vessels. (See all compounds classified as Vasodilator Agents.)

    5.3 ATC Code

    C - Cardiovascular system

    C02 - Antihypertensives

    C02D - Arteriolar smooth muscle, agents acting on

    C02DA - Thiazide derivatives

    C02DA01 - Diazoxide

    V - Various

    V03 - All other therapeutic products

    V03A - All other therapeutic products

    V03AH - Drugs for treatment of hypoglycemia

    V03AH01 - Diazoxide

    5.4 Absorption, Distribution and Excretion

    Absorption

    Readily absorbed following oral administration.

    Route of Elimination

    Proglycem is extensively bound (more than 90%) to serum proteins, and is excreted in the kidneys.

    5.5 Metabolism/Metabolites

    Hepatic.

    5.6 Biological Half-Life

    28 ±8.3 hours in normal adults.

    5.7 Mechanism of Action

    Diazoxide inhibits insulin release from the pancreas, by opening potassium channels in the beta cell membrane. Diazoxide is chemically related to thiazide diuretics but does not inhibit carbonic anhydrase and does not have chloriuretic or natriuretic activity. It also exhibits hypotensive activity by reducing arteriolar smooth muscle and vascular resistance.