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Chemistry

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Also known as: 577-11-7, Dioctyl sodium sulfosuccinate, Dioctyl sulfosuccinate sodium salt, Aerosol ot, Constonate, Dioctylal

Molecular Formula

C₂₀H₃₇NaO₇S

Molecular Weight

444.6 g/mol

InChI Key

APSBXTVYXVQYAB-UHFFFAOYSA-M

FDA UNII

F05Q2T2JA0

All-purpose surfactant, wetting agent, and solubilizer used in the drug, cosmetics, and food industries. It has also been used in laxatives and as cerumenolytics. It is usually administered as either the calcium, potassium, or sodium salt.

1 2D Structure

Docusate Sodium

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

sodium;1,4-bis(2-ethylhexoxy)-1,4-dioxobutane-2-sulfonate

2.1.2 InChI

InChI=1S/C20H38O7S.Na/c1-5-9-11-16(7-3)14-26-19(21)13-18(28(23,24)25)20(22)27-15-17(8-4)12-10-6-2;/h16-18H,5-15H2,1-4H3,(H,23,24,25);/q;+1/p-1

2.1.3 InChI Key

APSBXTVYXVQYAB-UHFFFAOYSA-M

2.1.4 Canonical SMILES

CCCCC(CC)COC(=O)CC(C(=O)OCC(CC)CCCC)S(=O)(=O)[O-].[Na+]

2.2 Other Identifiers

2.2.1 UNII

F05Q2T2JA0

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Aerosol Ot

2. Colace

3. Deh Na Ss

4. Deh-na-ss

5. Diethylhexyl Sodium Sulfosuccinate

6. Dioctyl Sulfosuccinate

7. Dioctyl Sulfosuccinate, Sodium

8. Dioctyl Sulfosuccinates

9. Dioctyl Sulfosuccinic Acid

10. Dioctyl Sulfosuccinic Acid, Ammonium Salt

11. Dioctyl Sulfosuccinic Acid, Barium Salt

12. Dioctyl Sulfosuccinic Acid, Calcium Salt

13. Dioctyl Sulfosuccinic Acid, Magnesium Salt

14. Dioctyl Sulfosuccinic Acid, Potassium Salt

15. Dioctyl Sulfosuccinic Acid, Sodium Salt

16. Dioctylsulfosuccinate

17. Dioctylsulphosuccinate, Sodium

18. Docusate

19. Docusate Calcium

20. Docusate Potassium

21. Doss

22. Sodium Bis(2-ethylhexyl)sulfosuccinate

23. Sodium Dioctyl Sulfosuccinate

24. Sodium Dioctylsulphosuccinate

25. Sodium Sulfosuccinate, Diethylhexyl

26. Sulfosuccinate, Diethylhexyl Sodium

27. Sulfosuccinate, Dioctyl

28. Sulfosuccinates, Dioctyl

29. Sulfosuccinic Acid Bis(2-ethylhexyl) Ester

2.3.2 Depositor-Supplied Synonyms

1. 577-11-7

2. Dioctyl Sodium Sulfosuccinate

3. Dioctyl Sulfosuccinate Sodium Salt

4. Aerosol Ot

5. Constonate

6. Dioctylal

7. Diotilan

8. Disonate

9. Molatoc

10. Regutol

11. Doxol

12. Nevax

13. Velmol

14. Docusate (sodium)

15. Doxinate

16. Colace

17. Dialose

18. Molcer

19. Soliwax

20. Waxsol

21. Docusate Sodium Salt

22. Diox

23. Manoxol Ot

24. Adekacol Ec 8600

25. Bis(2-ethylhexyl) Sulfosuccinate Sodium Salt

26. Dioctyl Sulfosuccinate Sodium

27. Comfolax

28. Coprola

29. Dulcivac

30. Eurowet

31. Jamylene

32. Empimin Op70

33. Sanmorin Ot 70n

34. Airrol Ct-1

35. Mackanate Dos-70

36. Nikkol Otp-75

37. Triton Gr-pg 70

38. Gemtex Pa-70

39. Rapisol A 30

40. Bis(2-ethylhexyl) Sodium Sulfosuccinate

41. Nissan Rapisol A 30

42. Dioctyl Ester Of Sodium Sulfosuccinic Acid

43. Ins No.480

44. Monawet Mo 65-150

45. Sodium 1,4-bis[(2-ethylhexyl)oxy]-1,4-dioxobutane-2-sulfonate

46. Ins-480

47. Butanedioic Acid, Sulfo-, 1,4-bis(2-ethylhexyl) Ester, Sodium Salt

48. F05q2t2ja0

49. Sodium 1,4-bis(2-ethylhexyl) Sulfosuccinate

50. Diethylhexyl Sodium Sulfosuccinate

51. Sodium Docusate

52. Nsc-760404

53. Aot

54. Diomedicone

55. Clestol

56. Complemix

57. Defilin

58. Dioctlyn

59. Diosuccin

60. Dulsivac

61. Laxinate

62. Mervamine

63. Molofac

64. Requtol

65. Sobital

66. Coprol

67. Diovac

68. Konlax

69. Kosate

70. Obston

71. Softil

72. Revac

73. E 480

74. E-480

75. Modane Soft

76. Dsstox_cid_2959

77. Alcopol O

78. Alphasol Ot

79. Manoxal Ot

80. Sulfimel Dos

81. Aerosol Aot

82. Aerosol Gpg

83. Wetaid Sr

84. Dsstox_rid_76808

85. Aerosol Ot-a

86. Dsstox_gsid_22959

87. Laxinate 100

88. Sanmorin Ot 70

89. Triton Gr 7

90. Triton Gr-5

91. Aerosol Ot 70pg

92. Aerosol Ot 75

93. Celanol Dos 65

94. Celanol Dos 75

95. Dess

96. Humifen Wt 27g

97. Monawet Md 70e

98. Solusol-75%

99. Nikkol Otp 70

100. Aerosol A 501

101. Alkasurf Ss-o 75

102. Solusol-100%

103. Nekal Wt-27

104. Berol 478

105. Coloxyl

106. Dioctyl

107. Docolace

108. Docuprene

109. Geriplex

110. Silace

111. Unilax

112. Bloat Treatment

113. Docusato Sodico

114. Sodium Bis(2-ethylhexyl) Sulfosuccinate

115. Dioctyl Sodium Sulfosuccinate (jan)

116. Docusate Sodique

117. Dialose Plus

118. Natrii Dioctylsulfosuccinas

119. Tex-wet 1001

120. Senokot S

121. Correctol Caplets

122. Correctol Tablets

123. Senokap Dss

124. Docusatum Natricum

125. D-s-s

126. Doc Q Lace

127. Cas-577-11-7

128. Sodium Dioctyl Sulphosuccinate

129. Feen-a-mint Pills

130. Dioctyl Sodium Sulfosuccinate [jan]

131. Correctol Extra Gentle Tablets

132. Docusate Sodique [inn-french]

133. Docusato Sodico [inn-spanish]

134. Docusatum Natricum [inn-latin]

135. Hsdb 3065

136. 2-ethylhexyl Sulfosuccinate Sodium

137. Ncgc00164140-03

138. Einecs 209-406-4

139. Sv 102

140. Bis(2-ethylhexyl)sodium Sulfosuccinate

141. Dioctyl Ester Of Sodium Sulfosuccinate

142. Di-(2-ethylhexyl) Sodium Sulfosuccinate

143. Sodium Di-(2-ethylhexyl) Sulfosuccinate

144. Dioctyl Sodium Sulphosuccinat

145. Unii-f05q2t2ja0

146. Prenexa

147. Purgasol

148. Vinacol

149. Bis(2-ethylhexyl) S-sodium Sulfosuccinate

150. Ai3-00239

151. Docusate Sod

152. Sodium 1,4-bis(2-ethylhexyl)sulfosuccinate

153. 1,4-bis(2-ethylhexyl) Sodium Sulfosuccinate

154. Sodium Sulfodi-(2-ethylhexyl)-sulfosuccinate

155. Senexon-s

156. Folca[s Care Pme

157. Folcal Dha

158. Senna-s

159. Di(2-ethylhexyl)sulfosuccinic Acid, Sodium Salt

160. Bis(ethylhexyl) Ester Of Sodium Sulfosuccinic Acid

161. Bis-2-ethylhexylester Sulfojantaranu Sodneho [czech]

162. Colace (tn)

163. Mfcd00012455

164. Sodium Di(2-ethylhexyl)sulfosuccinate

165. Sulfosuccinic Acid, Bis(2-ethylhexyl)ester Sodium Salt

166. Docusate Sodium [usan:usp:inn:ban]

167. Sol Sodowej Sulfobursztynianu Dwu-2-etyloheksylowego [polish]

168. Docusate Sodium (usp)

169. Docusate Sodium Solution

170. Bis-2-ethylhexylester Sulfojantaranu Sodneho

171. Chemax Doss/75e

172. Succinic Acid, Sulfo-, 1,4-bis(2-ethylhexyl) Ester, Sodium Salt

173. Ncgc00183136-01

174. Ec 209-406-4

175. Schembl4113

176. Docusate Sodium [ii]

177. Docusate Sodium [mi]

178. Mls004773938

179. Docusate Sodium [inn]

180. 1,4-bis(2-ethylhexyl)sulfobutanedioate, Sodium Salt

181. Sol Sodowej Sulfobursztynianu Dwu-2-etyloheksylowego

182. Docusate Sodium [hsdb]

183. Docusate Sodium [usan]

184. Chebi:4674

185. Sulfosuccinic Acid Bis(2-ethylhexyl) Ester Sodium Salt

186. Docusate Sodium [vandf]

187. Chembl1905872

188. Docusate Sodium [mart.]

189. Dtxsid8022959

190. Correctol Stool Softener Laxative

191. Docusate Sodium [usp-rs]

192. Docusate Sodium [who-dd]

193. Sulfosuccinic Acid, Di-(2-ethylhexyl) Ester, Sodium Salt

194. Hms3264p07

195. Hms3885b10

196. Sodium;1,4-bis(2-ethylhexoxy)-1,4-dioxobutane-2-sulfonate

197. Bcp31325

198. Hy-b1268

199. 4-(4-bromophenoxymethyl)benzoicacid

200. Aerosol™ Ot, Solid Anhydrous

201. Sodium Dioctyl Sulfosuccinate (inn)

202. Tox21_112087

203. Tox21_113469

204. Tox21_201342

205. Tox21_300496

206. S4588

207. Dioctyl Disodium Sulfosuccinate

208. Akos015901806

209. Docusate Sodium [usp Impurity]

210. Ccg-213234

211. Cs-4813

212. Docusate Sodium [usp Monograph]

213. Nsc 760404

214. Sodium Di(2-ethylhexyl) Sulfosuccinate

215. Docusate Sodium Salt, Bioxtra, >=99%

216. Docusate Sodium Solution [vandf]

217. Dioctyl Sulfosuccinate Sodium Salt, 96%

218. Ncgc00164140-01

219. Ncgc00254414-01

220. Ncgc00258894-01

221. As-13347

222. E480

223. Smr001595510

224. Aerosol™ Ot Solution, 10% (w/w)

225. Dioctyl Sodium Sulfosuccinate [fcc]

226. Dioctyl Sodium Sulfosuccinate With Ethanol

227. Bis(2-ethylhexyl) Sulfosuccinatesodium Salt

228. Dioctyl Sulfosuccinate Sodium Salt, >=97%

229. Aec Diethylhexyl Sodium Sulfosuccinate

230. Ft-0689234

231. D00305

232. Docusate Sodium Salt, P.a., 99.0-100.5%

233. E77584

234. Diethylhexyl Sodium Sulfosuccinate [inci]

235. Docusate Sodium Salt, Purum, >=96.0% (tlc)

236. Docusate Sodium Salt, Bioultra, >=99.0% (tlc)

237. Docusate Sodium, Meets Usp Testing Specifications

238. Dioctyl Sodium Sulfosuccinate With Diethylene Glycol

239. Dioctyl Sodium Sulfosuccinate With Propylene Glycol

240. Q2815334

241. W-105447

242. F8880-5559

243. Docusate Sodium, British Pharmacopoeia (bp) Reference Standard

244. Docusate Sodium, European Pharmacopoeia (ep) Reference Standard

245. Sodium 1,4-bis(2-ethylhexyloxy)-1,4-dioxobutane-2-sulfonate

246. Docusate Sodium, United States Pharmacopeia (usp) Reference Standard

247. Dioctyl Sodium Sulfosuccinate With Diethylene Glycol And Glycol Ethers

248. 1,4-bis(2-ethylhexyl)sodiumsulfosuccinate Pound>>dioctyl Sulfosuccinate Sodium Salt

249. Butanedioic Acid, 2-sulfo-, 1,4-bis(2-ethylhexyl) Ester, Sodium Salt (1:1)

250. Yal

2.4 Create Date

2008-02-05

3 Chemical and Physical Properties

Molecular Formula	C₂₀H₃₇NaO₇S
Molecular Weight	444.6 g/mol
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	18
Exact Mass	444.21576897 g/mol
Monoisotopic Mass	444.21576897 g/mol
Topological Polar Surface Area	118 Å²
Heavy Atom Count	29
Formal Charge	0
Complexity	546
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	3
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

4 Drug and Medication Information

4.1 Therapeutic Uses

Cathartics; Excipients; Surface-Active Agents

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

Oral bulk-forming, lubricant, and stool softener laxatives are indicated prophylactically in patients who should not strain during defecation, such as those with an episiotomy wound, painful thrombosed hemorrhoids, fissures or perianal abbesses, body wall and diaphragmatic hernias, anorectal stenosis, or postmyocardial infarction. /Laxatives; Included in US product labeling/

USP Convention. USPDI-Drug Information for the Health Care Professional. 14th ed. Volume I. Rockville, MD: United States Pharmacopeial Convention, Inc., 1994. (Plus Updates)., p. 1704

Oral laxatives are indicated for the short-term relief of constipation. Oral bulk-forming laxatives, stimulant laxatives, and carbon dioxide-releasing suppositories are indicated to facilitate defecation in geriatric patients with diminished colonic motor response. Oral bulk-forming laxatives and stool softener laxatives are preferred to treat constipation that may occur during pregnancy and postpartum to help re-establish normal bowel function or to avoid straining if hemorrhoids are present. In severe cases of constipation, such as with fecal impaction, mineral oil and stool softener laxatives administered orally or rectally are indicated to soften the impacted feces. To help complete the evacuation of the impacted colon, a rectal stimulant or saline laxative may follow. /Laxatives; Included in US product labeling/

USP Convention. USPDI-Drug Information for the Health Care Professional. 14th ed. Volume I. Rockville, MD: United States Pharmacopeial Convention, Inc., 1994. (Plus Updates)., p. 1704

4.2 Drug Warning

Laxatives should not be given to young children (up to 6 years of age) unless prescribed by a physician. Since children are not usually able to describe their symptoms precisely, proper diagnosis should precede the use of a laxative. This will avoid the complication of an existing condition(e.g., appendicitis) or the appearance of more severe side effects. /Laxatives/

USP Convention. USPDI-Drug Information for the Health Care Professional. 14th ed. Volume I. Rockville, MD: United States Pharmacopeial Convention, Inc., 1994. (Plus Updates)., p. 1705

Side/Adverse Effects: Those indicating need for medical attention: Incidence rare: Allergies, undetermined (skin rash). /Laxatives/

USP Convention. USPDI-Drug Information for the Health Care Professional. 14th ed. Volume I. Rockville, MD: United States Pharmacopeial Convention, Inc., 1994. (Plus Updates)., p. 1707

Side/Adverse Effects: Those indicating need for medical attention only if they continue or are bothersome: Incidence less frequent: Stomach and/or intestinal cramping; throat irritation - with liquid forms. /Laxatives/

USP Convention. USPDI-Drug Information for the Health Care Professional. 14th ed. Volume I. Rockville, MD: United States Pharmacopeial Convention, Inc., 1994. (Plus Updates)., p. 1707

Because concurrent use of the docusate salts may increase the absorption of mineral oil, their concomitant administration is not recommended. /Docusate salts/

American Medical Association, Council on Drugs. AMA Drug Evaluations Annual 1994. Chicago, IL: American Medical Association, 1994., p. 952

For more Drug Warnings (Complete) data for BIS(2-ETHYLHEXYL) SODIUM SULFOSUCCINATE (7 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).

Gosselin, R.E., R.P. Smith, H.C. Hodge. Clinical Toxicology of Commercial Products. 5th ed. Baltimore: Williams and Wilkins, 1984., p. II-274

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Surface-Active Agents

Agents that modify interfacial tension of water; usually substances that have one lipophilic and one hydrophilic group in the molecule; includes soaps, detergents, emulsifiers, dispersing and wetting agents, and several groups of antiseptics. (See all compounds classified as Surface-Active Agents.)

5.2 ATC Code

A06AA02

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

A - Alimentary tract and metabolism

A06 - Drugs for constipation

A06A - Drugs for constipation

A06AA - Softeners, emollients

A06AA02 - Docusate sodium

5.3 Absorption, Distribution and Excretion

...DRUG IS ABSORBED FROM GI TRACT & IS EXCRETED IN SIGNIFICANT CONCN IN BILE.

Gilman, A.G., T.W. Rall, A.S. Nies and P. Taylor (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 8th ed. New York, NY. Pergamon Press, 1990., p. 922

SINCE THE DRUG IS ABSORBED FROM GI TRACT & IS EXCRETED IN SIGNIFICANT CONCN IN BILE...

Gilman, A.G., T.W. Rall, A.S. Nies and P. Taylor (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 8th ed. New York, NY. Pergamon Press, 1990., p. 922

5.4 Mechanism of Action

In vitro studies suggest that these salts of dioctylsulfosuccinic acid lower the surface tension of the stool to permit water and lipids to enter more readily and thus soften the feces. ... More recent evidence indicates that they may stimulate the secretion of water and electrolytes on contact with the mucosa.

American Medical Association, Council on Drugs. AMA Drug Evaluations Annual 1994. Chicago, IL: American Medical Association, 1994., p. 949

Reduce surface film tension of interfacing liquid contents of the bowel, promoting permeation of additional liquid into the stool to form a softer mass. /Laxatives/

USP Convention. USPDI-Drug Information for the Health Care Professional. 14th ed. Volume I. Rockville, MD: United States Pharmacopeial Convention, Inc., 1994. (Plus Updates)., p. 1705

API SUPPLIERS

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USDMF

01

Mallinckrodt Inc

Ireland

Pharmtech & Ingredients

Not Confirmed

02

E Merck

Germany

Pharmtech & Ingredients

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03

Napp Chemicals Inc

U.S.A

Pharmtech & Ingredients

Not Confirmed

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Cytec Industries Inc

Belgium

Pharmtech & Ingredients

Not Confirmed

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CYTEC INDUSTRIES INC. Princeton US

Belgium

Pharmtech & Ingredients

Not Confirmed

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01

Cytec Industries Inc.

Belgium

Pharmtech & Ingredients

Not Confirmed

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API Reference Price

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