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Technical details about Prestwick3_000014, learn more about the structure, uses, toxicity, action, side effects and more

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2D Structure
Also known as: 144-80-9, Sulphacetamide, Acetosulfamine, N-((4-aminophenyl)sulfonyl)acetamide, N-acetylsulfanilamide, N-sulfanilylacetamide
Molecular Formula
C8H10N2O3S
Molecular Weight
214.24  g/mol
InChI Key
SKIVFJLNDNKQPD-UHFFFAOYSA-N
FDA UNII
4965G3J0F5

An anti-bacterial agent that is used topically to treat skin infections and orally for urinary tract infections.
Sulfacetamide is a Sulfonamide Antibacterial.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
N-(4-aminophenyl)sulfonylacetamide
2.1.2 InChI
InChI=1S/C8H10N2O3S/c1-6(11)10-14(12,13)8-4-2-7(9)3-5-8/h2-5H,9H2,1H3,(H,10,11)
2.1.3 InChI Key
SKIVFJLNDNKQPD-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CC(=O)NS(=O)(=O)C1=CC=C(C=C1)N
2.2 Other Identifiers
2.2.1 UNII
4965G3J0F5
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Acetopt

2. Acetylsulfanilamide

3. Ak Sulf

4. Ak-sulf

5. Albucid

6. Antbor

7. Belph 10

8. Belph-10

9. Bleph

10. Ceta Sulfa

11. Cetamide

12. Colircusi Sulfacetamida

13. Coliriocilina Sulfacetam

14. Isopto Cetamide

15. Sodium Sulamyd

16. Sulamyd, Sodium

17. Sulf 10

18. Sulf-10

19. Sulfacetam, Coliriocilina

20. Sulfacetamida, Colircusi

21. Sulfacetamide Monosodium Salt

22. Sulfacetamide Sodium

23. Sulfacetamide, Monosodium Salt, Anhydrous

24. Sulfacil

25. Sulfacyl

26. Sulfair

27. Sulphacetamide

2.3.2 Depositor-Supplied Synonyms

1. 144-80-9

2. Sulphacetamide

3. Acetosulfamine

4. N-((4-aminophenyl)sulfonyl)acetamide

5. N-acetylsulfanilamide

6. N-sulfanilylacetamide

7. Albucid

8. Acetosulfamin

9. Urosulfon

10. N-sulphanilylacetamide

11. Sulfacetimide

12. Acetocid

13. Sulfacet

14. Sulfacyl

15. Sulfanilacetamide

16. Formosulfacetamide

17. N-(4-aminophenyl)sulfonylacetamide

18. Albamine

19. Sulphasil

20. Urosulfone

21. Alesten

22. Oclucid

23. Region

24. Sulamyd

25. Sulfanilazetamid

26. P-aminobenzenesulfonacetamide

27. Sulf-10

28. Bleph-10

29. N-[(4-aminophenyl)sulfonyl]acetamide

30. N-acetyl-4-aminobenzenesulfonamide

31. Sulfacetamidum

32. Sulphacetamidum

33. Steramide

34. Sebizon

35. Isopto Cetamide

36. Ophthel-s

37. P-aminobenzenesulfonoacetamide

38. N'-acetylsulfanilamide

39. Sulfacetamida

40. Bleph-10 Liquifilm

41. Op-sulfa 30

42. Sulfacylum

43. Sulfacel-15

44. Acetamide, N-sulfanilyl-

45. Klaron

46. N-((p-aminophenyl)sulfonyl)acetamide

47. N(sup1)-acetylsulfanilamide

48. A-500

49. Ocusulf-10

50. Sulfair-15

51. Sulten-10

52. N-(4-aminophenylsulfonyl)acetamide

53. Sulster

54. Sulf-15

55. N-[(p-aminophenyl)sulfonyl]acetamide

56. Fml-s

57. N(sup 1)-acetyl-4-aminophenylsulfonamide

58. Sulfanilamide, N(sup 1)-acetyl-

59. Acetamide, N-((4-aminophenyl)sulfonyl)-

60. Acetamide, N-[(4-aminophenyl)sulfonyl]-

61. Nsc 63871

62. N-(p-aminobenzenesulfonyl)acetamide

63. N(1)-acetylsulfanilamide

64. Mfcd00066501

65. Nsc-63871

66. Chembl455

67. Triple Sulfa (sulfacetamide)

68. Metimyd

69. Mls000069710

70. Solfacetamide

71. Chebi:63845

72. Ocusulf-30

73. Bleph-30

74. N-acetyl-4-amino-benzenesulfonamide

75. N(1)-acetyl-4-aminophenylsulfonamide

76. 4965g3j0f5

77. Sulfacyl (van)

78. Ncgc00018242-04

79. Ncgc00018242-07

80. Smr000058173

81. N1-acetylsulfanilamide

82. Solfacetamide [dcit]

83. Sulfacetamide 100 Microg/ml In Acetonitrile

84. Dsstox_cid_6060

85. 5414-91-5

86. Dsstox_rid_78000

87. Sulfanilazetamid [german]

88. Dsstox_gsid_26060

89. N-acetylsulfanilamine

90. Sulfacetamidum [inn-latin]

91. Sulfacetamida [inn-spanish]

92. N(sup 1)-acetylsulfanilamide

93. Caswell No. 808a

94. Cas-144-80-9

95. Ccris 6273

96. Einecs 205-640-6

97. Sulfacetamide (usp/inn)

98. Epa Pesticide Chemical Code 077904

99. Brn 0981718

100. Ai3-26837

101. Sulfacetamide [usp:inn:ban]

102. Unii-4965g3j0f5

103. Sulfacetamide, 1

104. Cetapred

105. Predamide

106. Spectrum_000984

107. Opera_id_1990

108. Prestwick0_000014

109. Prestwick1_000014

110. Prestwick2_000014

111. Prestwick3_000014

112. Spectrum2_001318

113. Spectrum3_001017

114. Spectrum4_001146

115. Spectrum5_001230

116. Wln: Zr Dswmv1

117. Sulfacetamide [mi]

118. Cbchromo1_000180

119. Sulfanilamide, N1-acetyl-

120. 4-acetylaminosulfonylaniline

121. Sulfacetamide [inn]

122. Nciopen2_002838

123. Sulfacetamide, >=98.0%

124. Oprea1_686524

125. Oprea1_810285

126. Schembl40863

127. Bspbio_000047

128. Bspbio_002773

129. Cbdive_013934

130. Kbiogr_001691

131. Kbioss_001464

132. Sulfacetamide [vandf]

133. 4-14-00-02662 (beilstein Handbook Reference)

134. Mls001076499

135. Divk1c_000227

136. Spectrum1500545

137. Sulfacetamide [mart.]

138. Spbio_001415

139. Spbio_001968

140. Sulfacetamide [who-dd]

141. Sulfacetamide [who-ip]

142. Bpbio1_000053

143. Dtxsid8026060

144. Hms500l09

145. Kbio1_000227

146. Kbio2_001464

147. Kbio2_004032

148. Kbio2_006600

149. Kbio3_001993

150. 4-[(acetylamino)sulfonyl]aniline

151. Ninds_000227

152. 4-[(acetylamino) Sulfonyl]aniline

153. Hms1921a11

154. Hms2092i13

155. Hms2232k07

156. Hms3259g06

157. Hms3374o02

158. Pharmakon1600-01500545

159. Sulfacetamide [orange Book]

160. Sulfacetamide, >=98.0% (nt)

161. Hy-n7123

162. Nsc63871

163. Zinc5179119

164. Sulfacetamide (triple Sulfa)

165. Sulfacetamide [usp Impurity]

166. Tox21_110846

167. Tox21_201999

168. Tox21_303100

169. Ac2473

170. Bbl012083

171. Bdbm50316126

172. Ccg-39256

173. Nsc757323

174. S5546

175. Stk068185

176. Trysul Component Sulfacetamide

177. Sulfacetamidum [who-ip Latin]

178. Sultrin Component Sulfacetamide

179. Vagilia Component Sulfacetamide

180. Akos000119729

181. N-[(4-aminobenzene)sulfonyl]acetamide

182. Tox21_110846_1

183. Ac-7630

184. Db00634

185. Ks-5327

186. Nc00538

187. Nsc-757323

188. Gyne-sulf Component Sulfacetamide

189. Idi1_000227

190. Sulfacetamide Component Of Trysul

191. Ncgc00018242-01

192. Ncgc00018242-02

193. Ncgc00018242-03

194. Ncgc00018242-05

195. Ncgc00018242-06

196. Ncgc00018242-08

197. Ncgc00021857-03

198. Ncgc00021857-04

199. Ncgc00021857-05

200. Ncgc00257159-01

201. Ncgc00259548-01

202. Sulfacetamide 100 Microg/ml In Methanol

203. Sulfacetamide Component Of Sultrin

204. Sulfacetamide Component Of Vagilia

205. Sy014752

206. Sbi-0051519.p003

207. Db-042749

208. Sulfacetamide Component Of Gyne-sulf

209. Cs-0013812

210. Ft-0631838

211. S0577

212. Sulfadimidine Impurity E [ep Impurity]

213. D05947

214. Ab00052094_14

215. Sr-01000000194

216. Sulfacetamide, Vetranal(tm), Analytical Standard

217. Triple Sulfa (sulfacetamide) [orange Book]

218. Q-201757

219. Q2022983

220. Sr-01000000194-2

221. Sulfacetamide, Antibiotic For Culture Media Use Only

222. Brd-k21520694-001-12-3

223. N-((4-aminophenyl)sulfonyl)acetamide [who-ip]

224. Sulfacetamide, United States Pharmacopeia (usp) Reference Standard

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 214.24 g/mol
Molecular Formula C8H10N2O3S
XLogP3-1
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count4
Rotatable Bond Count2
Exact Mass214.04121336 g/mol
Monoisotopic Mass214.04121336 g/mol
Topological Polar Surface Area97.6 Ų
Heavy Atom Count14
Formal Charge0
Complexity299
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 6  
Drug NameBleph-10
PubMed HealthSulfacetamide
Drug ClassesAntiacne Antibacterial, Antibiotic, Antiseborrheic, Dermatological Agent
Drug LabelBLEPH-10 (sulfacetamide sodium ophthalmic solution, USP) 10% is a sterile, topical anti-bacterial agent for ophthalmic use. The active ingredient is represented by the following structural formula:...
Active IngredientSulfacetamide sodium
Dosage FormSolution/drops
RouteOphthalmic
Strength10%
Market StatusPrescription
CompanyAllergan

2 of 6  
Drug NameCetamide
PubMed HealthSulfacetamide/Sulfur (On the skin)
Drug ClassesAntiacne, Antiacne Antibacterial, Antibacterial, Antibacterial Cleansing Agent, Antiseborrheic, Keratolytic
Drug LabelEach gram contains 100 mg of sodium sulfacetamide in a vehicle consisting of: cocamidopropyl betaine, disodium EDTA, methylparaben, PEG-60 almond triglycerides, PEG-150 pentaerythrityl tetrastearate (and) aqua (and) PEG-6 caprylic/capric glycerides,...
Active IngredientSulfacetamide sodium
Dosage FormOintment
RouteOphthalmic
Strength10%
Market StatusPrescription
CompanyAlcon

3 of 6  
Drug NameKlaron
PubMed HealthSulfacetamide
Drug ClassesAntiacne Antibacterial, Antibiotic, Antiseborrheic, Dermatological Agent
Drug LabelEach mL of Klaron (sodium sulfacetamide lotion) Lotion, 10% contains 100 mg of sodium sulfacetamide in a vehicle consisting of purified water; propylene glycol; lauramide DEA (and) diethanolamine; polyethylene glycol 400, monolaurate; hydroxyethyl...
Active IngredientSulfacetamide sodium
Dosage FormLotion
RouteTopical
Strength10%
Market StatusPrescription
CompanyValeant Bermuda

4 of 6  
Drug NameBleph-10
PubMed HealthSulfacetamide
Drug ClassesAntiacne Antibacterial, Antibiotic, Antiseborrheic, Dermatological Agent
Drug LabelBLEPH-10 (sulfacetamide sodium ophthalmic solution, USP) 10% is a sterile, topical anti-bacterial agent for ophthalmic use. The active ingredient is represented by the following structural formula:...
Active IngredientSulfacetamide sodium
Dosage FormSolution/drops
RouteOphthalmic
Strength10%
Market StatusPrescription
CompanyAllergan

5 of 6  
Drug NameCetamide
PubMed HealthSulfacetamide/Sulfur (On the skin)
Drug ClassesAntiacne, Antiacne Antibacterial, Antibacterial, Antibacterial Cleansing Agent, Antiseborrheic, Keratolytic
Drug LabelEach gram contains 100 mg of sodium sulfacetamide in a vehicle consisting of: cocamidopropyl betaine, disodium EDTA, methylparaben, PEG-60 almond triglycerides, PEG-150 pentaerythrityl tetrastearate (and) aqua (and) PEG-6 caprylic/capric glycerides,...
Active IngredientSulfacetamide sodium
Dosage FormOintment
RouteOphthalmic
Strength10%
Market StatusPrescription
CompanyAlcon

6 of 6  
Drug NameKlaron
PubMed HealthSulfacetamide
Drug ClassesAntiacne Antibacterial, Antibiotic, Antiseborrheic, Dermatological Agent
Drug LabelEach mL of Klaron (sodium sulfacetamide lotion) Lotion, 10% contains 100 mg of sodium sulfacetamide in a vehicle consisting of purified water; propylene glycol; lauramide DEA (and) diethanolamine; polyethylene glycol 400, monolaurate; hydroxyethyl...
Active IngredientSulfacetamide sodium
Dosage FormLotion
RouteTopical
Strength10%
Market StatusPrescription
CompanyValeant Bermuda

4.2 Drug Indication

For the treatment of bacterial vaginitis, keratitis, acute conjunctivitis, and blepharitis.


FDA Label


5 Pharmacology and Biochemistry
5.1 Pharmacology

Sulfacetamide is a sulfonamide antibiotic with bacteriostatic actions and broad-spectrum activity against most gram-positive and many gram-negative organisms. However, many strains of an individual species may be resistant. Sulfonamides inhibit multiplication of bacteria by acting as competitive inhibitors of p-aminobenzoic acid in the folic acid metabolism cycle. Bacterial sensitivity is the same for the various sulfonamides, and resistance to one sulfonamide indicates resistance to all. Most sulfonamides are readily absorbed orally. However, parenteral administration is difficult, since the soluble sulfonamide salts are highly alkaline and irritating to the tissues. The sulfonamides are widely distributed throughout all tissues. High levels are achieved in pleural, peritoneal, synovial, and ocular fluids. Although these drugs are no longer used to treat meningitis, CSF levels are high in meningeal infections. Their antibacterial action is inhibited by pus.


5.2 MeSH Pharmacological Classification

Anti-Bacterial Agents

Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)


Anti-Infective Agents, Local

Substances used on humans and other animals that destroy harmful microorganisms or inhibit their activity. They are distinguished from DISINFECTANTS, which are used on inanimate objects. (See all compounds classified as Anti-Infective Agents, Local.)


Anti-Infective Agents, Urinary

Substances capable of killing agents causing urinary tract infections or of preventing them from spreading. (See all compounds classified as Anti-Infective Agents, Urinary.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
SULFACETAMIDE
5.3.2 FDA UNII
4965G3J0F5
5.3.3 Pharmacological Classes
Chemical Structure [CS] - Sulfonamides
5.4 ATC Code

D - Dermatologicals

D10 - Anti-acne preparations

D10A - Anti-acne preparations for topical use

D10AF - Antiinfectives for treatment of acne

D10AF06 - Sulfacetamide


S - Sensory organs

S01 - Ophthalmologicals

S01A - Antiinfectives

S01AB - Sulfonamides

S01AB04 - Sulfacetamide


5.5 Biological Half-Life

7-12.8 hours


5.6 Mechanism of Action

Sulfacetamide is a competitive inhibitor of bacterial para-aminobenzoic acid (PABA), an essential component for bacterial growth (according to the Woods-Fildes theory). The inhibited reaction is necessary in these organisms for the synthesis of folic acid.


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