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Prestwick3_000087

Prestwick3_000087

Synopsis, Chemistry

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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

Prestwick3_000087

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 Formula	C₈H₇ClN₂O₂S
Molecular Weight	230.67 g/mol
XLogP3	1.2
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	0
Exact Mass	229.9916763 g/mol
Monoisotopic Mass	229.9916763 g/mol
Topological Polar Surface Area	66.9 Å²
Heavy Atom Count	14
Formal Charge	0
Complexity	360
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 Information

1 of 2
Drug Name	Proglycem
PubMed Health	Diazoxide (By mouth)
Drug Classes	Gastrointestinal Agent, Glucose Regulation, Antihypoglycemic
Drug Label	PROGLYCEM (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 Ingredient	Diazoxide
Dosage Form	Suspension
Route	Oral
Strength	50mg/ml
Market Status	Prescription
Company	Teva Branded Pharm

2 of 2
Drug Name	Proglycem
PubMed Health	Diazoxide (By mouth)
Drug Classes	Gastrointestinal Agent, Glucose Regulation, Antihypoglycemic
Drug Label	PROGLYCEM (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 Ingredient	Diazoxide
Dosage Form	Suspension
Route	Oral
Strength	50mg/ml
Market Status	Prescription
Company	Teva 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.

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