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Triamcinolone Acetonide

Synopsis, Chemistry

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DRUG PRODUCT COMPOSITION

CREAM;TOPICAL - 0.025% **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**, CREAM;TOPICAL - 0.1% **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**, INJECTABLE;INJECTION - 10MG/ML, SPRAY;TOPICAL - 0.147MG/GM, INJECTABLE;INJECTION - 40MG/ML, INJECTABLE;INJECTION - 80MG/ML, SPRAY, METERED;NASAL - 0.055MG/SPRAY, FOR SUSPENSION, EXTENDED RELEASE;INTRA-ARTICULAR - 32MG/VIAL, CREAM;TOPICAL - 0.025%, CREAM;TOPICAL - 0.1%, CREAM;TOPICAL - 0.5%, OINTMENT;TOPICAL - 0.025%, OINTMENT;TOPICAL - 0.1%, OINTMENT;TOPICAL - 0.5%

CREAM;TOPICAL - 0.025% **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**
CREAM;TOPICAL - 0.1% **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**
INJECTABLE;INJECTION - 10MG/ML
SPRAY;TOPICAL - 0.147MG/GM
INJECTABLE;INJECTION - 40MG/ML
INJECTABLE;INJECTION - 80MG/ML
SPRAY, METERED;NASAL - 0.055MG/SPRAY
FOR SUSPENSION, EXTENDED RELEASE;INTRA-ARTICULAR - 32MG/VIAL
CREAM;TOPICAL - 0.025%
CREAM;TOPICAL - 0.1%
CREAM;TOPICAL - 0.5%
OINTMENT;TOPICAL - 0.025%
OINTMENT;TOPICAL - 0.1%
OINTMENT;TOPICAL - 0.5%

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Also known as: 76-25-5, Azmacort, Nasacort, Aristoderm, Aristogel, Vetalog

Molecular Formula

C₂₄H₃₁FO₆

Molecular Weight

434.5 g/mol

InChI Key

YNDXUCZADRHECN-JNQJZLCISA-N

FDA UNII

F446C597KA

An esterified form of TRIAMCINOLONE. It is an anti-inflammatory glucocorticoid used topically in the treatment of various skin disorders. Intralesional, intramuscular, and intra-articular injections are also administered under certain conditions.

Triamcinolone acetonide is a Corticosteroid. The mechanism of action of triamcinolone acetonide is as a Corticosteroid Hormone Receptor Agonist.

1 2D Structure

Triamcinolone Acetonide

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(1S,2S,4R,8S,9S,11S,12R,13S)-12-fluoro-11-hydroxy-8-(2-hydroxyacetyl)-6,6,9,13-tetramethyl-5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one

2.1.2 InChI

InChI=1S/C24H31FO6/c1-20(2)30-19-10-16-15-6-5-13-9-14(27)7-8-21(13,3)23(15,25)17(28)11-22(16,4)24(19,31-20)18(29)12-26/h7-9,15-17,19,26,28H,5-6,10-12H2,1-4H3/t15-,16-,17-,19+,21-,22-,23-,24+/m0/s1

2.1.3 InChI Key

YNDXUCZADRHECN-JNQJZLCISA-N

2.1.4 Canonical SMILES

CC1(OC2CC3C4CCC5=CC(=O)C=CC5(C4(C(CC3(C2(O1)C(=O)CO)C)O)F)C)C

2.1.5 Isomeric SMILES

C[C@]12C[C@@H]([C@]3([C@H]([C@@H]1C[C@@H]4[C@]2(OC(O4)(C)C)C(=O)CO)CCC5=CC(=O)C=C[C@@]53C)F)O

2.2 Other Identifiers

2.2.1 UNII

F446C597KA

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Acetonide, Triamcinolone

2. Azmacort

3. Cinonide

4. Kenacort A

5. Kenalog

6. Kenalog 40

7. Tricort 40

8. Tricort-40

9. Tricort40

2.3.2 Depositor-Supplied Synonyms

1. 76-25-5

2. Azmacort

3. Nasacort

4. Aristoderm

5. Aristogel

6. Vetalog

7. Kenalog

8. Tricinolon

9. Oralone

10. Rineton

11. Solodelf

12. Tramacin

13. Triacet

14. Triderm

15. Zilretta

16. Nasacort Aq

17. Volon A

18. Triaceton

19. Triacort

20. Triesence

21. Flutex

22. Flutone

23. Oracort

24. Triatex

25. Trymex

26. Allernaze

27. Aristocort A

28. Triam-injekt

29. Adcortyl A

30. Kenalog-h

31. Omcilon A

32. Tri-nasal

33. Nasacort Hfa

34. Coupe-a

35. Kenalog In Orabase

36. Aristocort Acetonide

37. Kenalog-10

38. Kenalog-40

39. Triamcinolone 16,17-acetonide

40. Trivaris

41. Triamcincolone Acetonide

42. Volon A 40

43. Kenacort-a

44. Kenalone

45. Triamcinolone (acetonide)

46. Nasacort Allergy 24 Hour

47. Triamcinolone Acetonide In Absorbase

48. Acetospan

49. Chebi:71418

50. Triamonide 40

51. Fx006

52. 9alpha-fluoro-16alpha-17alpha-isopropyledenedioxyprednisolone

53. Nsc-21916

54. Triamsinolone Acetonide

55. Fx-006

56. Mls000028538

57. (11beta,16alpha)-9-fluoro-11,21-dihydroxy-16,17-[(1-methylethylidene)bis(oxy)]pregna-1,4-diene-3,20-dione

58. F446c597ka

59. Tac-3

60. Kenalog 40

61. Tricort-40

62. Smr000058335

63. Dsstox_cid_1371

64. Dsstox_rid_76115

65. Dsstox_gsid_21371

66. Extracort

67. Ftorocort

68. Respicort

69. Volonimat

70. (4as,4br,5s,6as,6bs,9ar,10as,10bs)-4b-fluoro-5-hydroxy-6b-(hydroxyacetyl)-4a,6a,8,8-tetramethyl-4a,4b,5,6,6a,6b,9a,10,10a,10b,11,12-dodecahydro-2h-naphtho[2',1':4,5]indeno[1,2-d][1,3]dioxol-2-one

71. (4as,4br,5s,6as,6bs,9ar,10as,10bs)-4b-fluoro-6b-glycoloyl-5-hydroxy-4a,6a,8,8-tetramethyl-4a,4b,5,6,6a,6b,9a,10,10a,10b,11,12-dodecahydro-2h-naphtho[2',1':4,5]indeno[1,2-d][1,3]dioxol-2-one

72. Ledercort Cream

73. Vetalog (veterinary)

74. Trianex

75. 9alpha-fluoro-16alpha-hydroxyprednisolone 16alpha,17alpha-acetonide

76. Mfcd00056834

77. 9alpha-fluoro-16alpha-17alpha-isopropylidenedioxy-delta-1-hydrocortisone

78. 9-fluoro-11beta,16alpha,17,21-tetrahydroxypregna-1,4-diene-3,20-dione-16,17-acetonide

79. 9alpha-fluoro-11beta,21-dihydroxy-16alpha,17-isopropylidenedioxy-1,4-pregnadiene,3,20-dione

80. Cas-76-25-5

81. 9alpha-fluoro-11beta,21-dihydroxy-16alpha,17alpha-isopropylidenedioxypregna-1,4-diene-3,20-dione

82. Panolog Ointment (veterinary)

83. Triamcinolone Acetonide [jan]

84. Ccris 5231

85. Mls002638825

86. Einecs 200-948-7

87. Nsc 21916

88. Brn 0060069

89. Nystadermal

90. Audicort

91. Aureocort

92. Remiderm

93. Remotic

94. Silderm

95. Unii-f446c597ka

96. Tri-adcortyl

97. 9alpha-fluoro-16-hydroxyprednisolone Acetonide

98. Gppe Ear Oint

99. 9?-fluoro-11?,21-dihydroxy-16?,17?-isopropylidenedioxypregna-1,4-diene-3,20-dione

100. 9-alpha-fluoro-16-hydroxyprednisolone Acetonide

101. Kenalone, Solodelf

102. Ncgc00023193-04

103. Azmacort (tn)

104. Nasacort (tn)

105. Gppe Ear Dps Cap

106. Adcortyl In Orabase

107. Kenalog (tn)

108. Pevaryl T.c.

109. Xipere

110. Pregna-1,4-diene-3,20-dione, 9-fluoro-11,21-dihydroxy-16,17-((1-methylethylidene)bis(oxy))-, (11beta,16alpha)-

111. Triamcinolone-acetonide

112. Asmacort [common Misspelling Of Azmacort]

113. Opera_id_232

114. 9-alpha-fluoro-16-alpha-17-alpha-isopropyledenedioxyprednisolone

115. Triamcinolone Acetonide [usp:inn:ban:jan]

116. 9-alpha-fluoro-16-alpha-hydroxyprednisolone 16-alpha,17-alpha-acetonide

117. 9-alpha-fluoro-16-alpha-17-alpha-isopropylidenedioxy-delta-1-hydrocortisone

118. Schembl4689

119. 9-alpha-fluoro-11-beta,21-dihydroxy-16-alpha-isopropylidenedioxy-1,4-pregnadiene,3,20-dione

120. Chembl1504

121. 5-19-06-00568 (beilstein Handbook Reference)

122. 9-alpha-fluoro-11-beta,21-dihydroxy-16-alpha,17-alpha-isopropylidenedioxypregna-1,4-diene-3,20-dione

123. 9-fluoro-11beta,16alpha,17,21-tetrahydroxypregna-1,4-diene-3,20-dione Cyclic 16,17-acetal With Acetone

124. Mls001148264

125. Mls002207192

126. 9.alpha.-fluoro-16.alpha.-17.alpha.-isopropyledenedioxyprednisolone

127. Gtpl2867

128. Dtxsid6021371

129. Cls1001

130. 9.alpha.-fluoro-16.alpha.-hydroxyprednisolone 16.alpha.,17.alpha.-acetonide

131. Hms2232f22

132. Hms3259a20

133. 9-fluoro-11.beta.,16.alpha.,17,21-tetrahydroxypregna-1,4-diene-3,20-dione Cyclic 16,17-acetal With Acetone

134. 9alpha-fluoro-11beta,21-dihydroxy-16alpha,17-isopropylidenedioxy-1,4-pregnadiene-3,20-dione

135. Cls-1001

136. Hy-b0636

137. Nsc21916

138. Zinc3875481

139. Tox21_110885

140. Tox21_201795

141. Tox21_303014

142. Triamcinolone Acetonide [mi]

143. Bdbm50248362

144. Triamcinolone Acetonide (jp17/usp)

145. Akos015894871

146. Tox21_110885_1

147. Ac-1239

148. Ccg-269068

149. Ks-5330

150. Nc00591

151. Triamcinolone Acetonide [mart.]

152. Triamcinolone Acetonide [vandf]

153. Triamcinolone Acetonide [usp-rs]

154. Triamcinolone Acetonide [who-dd]

155. Ncgc00023193-05

156. Ncgc00023193-06

157. Ncgc00256560-01

158. Ncgc00259344-01

159. (4as,4br,5s,6as,6bs,9ar,10as,10bs)-4b-fluoro-5-hydroxy-6b-(hydroxyacetyl)-4a,6a,8,8-tetramethyl-4a,4b,5,6,6a,6b,9a,10,10a,10b,11,12-dodecahydro-2h,8h-naphtho[2',1':4,5]indeno[1,2-d][1,3]dioxol-2-one

160. Pregna-1,4-diene-3,20-dione, 9-fluoro-11-beta,16-alpha,17,21-tetrahydroxy-, Cyclic 16,17-acetal With Acetone

161. Pregna-1,4-diene-3,20-dione, 9-fluoro-11beta,16alpha,17,21-tetrahydroxy-, Cyclic 16,17-acetal With Acetone

162. Triamcinolone Acetonide [green Book]

163. Triamcinolone Acetonide, Analytical Standard

164. S1628

165. Triamcinolone Acetonide [orange Book]

166. Triamcinolone Acetonide [ep Monograph]

167. C08183

168. D00983

169. Dimethyl2-(3-nitro-2-pyridyl)malonate

170. Mycolog Component Triamcinolone Acetonide

171. Mykacet Component Triamcinolone Acetonide

172. Triamcinolone Acetonide [usp Monograph]

173. 9.alpha.-fluoro-16-hydroxyprednisolone Acetonide

174. Ab00383012-11

175. Ab00383012_12

176. Mytrex A Component Triamcinolone Acetonide

177. Mytrex F Component Triamcinolone Acetonide

178. 056t834

179. A856341

180. Triamcinolone Acetonide 100 Microg/ml In Methanol

181. Triamcinolone Acetonide Component Of Mycolog

182. Triamcinolone Acetonide Component Of Mykacet

183. Q-201855

184. Q2211240

185. Triamcinolone Acetonide 1000 Microg/ml In Methanol

186. Triamcinolone Acetonide Component Of Mytrex A

187. Triamcinolone Acetonide Component Of Mytrex F

188. 9.alpha.-fluoro-11.beta.,4-pregnadiene,3,20-dione

189. Brd-k53790871-001-08-6

190. Triamcinolone Hexacetonide Impurity A [ep Impurity]

191. Triamcinolone Acetonide, European Pharmacopoeia (ep) Reference Standard

192. Triamcinolone Acetonide, United States Pharmacopeia (usp) Reference Standard

193. Triamcinolone Acetonide; 76-25-5; Azmacort; Aristogel; Nasacort;

194. Wln: T F5 E5 B666 Go Io Rv Ahtttt&j A1 Bf Cq E1 Fv1q H1 H1

195. 9.alpha.-fluoro-16.alpha.-17.alpha.-isopropylidenedioxy-.delta.-1-hydrocortisone

196. Pregna-1,20-dione, 9-fluoro-11.beta.,21-dihydroxy-16.alpha.,17-(isopropylidenedioxy)-

197. Triamcinolone Acetonide, Pharmaceutical Secondary Standard; Certified Reference Material

198. 1ta

199. Pregna-1,20-dione, 9-fluoro-11,21-dihydroxy-16,17-[(1-methylethylidene)bis(oxy)]-, (11.beta.,16.alpha.)-

200. Pregna-1,20-dione, 9-fluoro-11.beta.,16.alpha.,17,21-tetrahydroxy-, Cyclic 16,17-acetal With Acetone

201. Pregna-1,20-dione, 9-fluoro-11.beta.,16.alpha.,17,21-tetrahydroxy-,cyclic 16,17-acetal With Acetone

202. Triamcinolone Acetonide For System Suitability, European Pharmacopoeia (ep) Reference Standard

2.4 Create Date

2005-03-26

3 Chemical and Physical Properties

Molecular Formula	C₂₄H₃₁FO₆
Molecular Weight	434.5 g/mol
XLogP3	2.5
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	2
Exact Mass	434.21046687 g/mol
Monoisotopic Mass	434.21046687 g/mol
Topological Polar Surface Area	93.1 Å²
Heavy Atom Count	31
Formal Charge	0
Complexity	925
Isotope Atom Count	0
Defined Atom Stereocenter Count	8
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 10
Drug Name	Kenalog-10
Drug Label	Kenalog-10 Injection (triamcinolone acetonide injectable suspension, USP) is triamcinolone acetonide, a synthetic glucocorticoid corticosteroid with marked anti-inflammatory action, in a sterile aqueous suspension suitable for intralesional and int...
Active Ingredient	Triamcinolone acetonide
Dosage Form	Injectable
Route	Injection
Strength	10mg/ml
Market Status	Prescription
Company	Apothecon

2 of 10
Drug Name	Kenalog-40
Drug Label	Kenalog-40 Injection (triamcinolone acetonide injectable suspension, USP) is a synthetic glucocorticoid corticosteroid with anti-inflammatory action. THIS FORMULATION IS SUITABLE FOR INTRAMUSCULAR AND INTRA-ARTICULAR USE ONLY. THIS FORMULATION IS N...
Active Ingredient	Triamcinolone acetonide
Dosage Form	Injectable
Route	Injection
Strength	40mg/ml
Market Status	Prescription
Company	Apothecon

3 of 10
Drug Name	Triamcinolone acetonide
Drug Label	Triamcinolone acetonide, USP, the active ingredient in Nasacort HFA Nasal Aerosol, is a glucocorticosteroid with a molecular weight of 434.5, the chemical designation 9-Fluoro-11,16,17,21-tetrahydroxypregna-1,4-diene-3,20-dione cyclic 16,17-ace...
Active Ingredient	Triamcinolone acetonide
Dosage Form	Ointment; Spray, metered; Paste; Cream; Lotion
Route	Dental; Nasal; Topical
Strength	0.5%; 0.055mg/spray; 0.1%; 0.025%
Market Status	Prescription
Company	Wockhardt; Taro; Lyne; Fougera Pharms; Teva Pharms; Versapharm; Vintage; Perrigo New York; Wockhardt Eu Operatn

4 of 10
Drug Name	Triamcinolone acetonide in absorbase
Drug Label	TRIESENCE (triamcinolone acetonide injectable suspension) 40 mg/mL is a synthetic corticosteroid with anti-inflammatory action. Each mL of the sterile, aqueous suspension provides 40 mg of triamcinolone acetonide, with sodium chloride for isotonici...
Active Ingredient	Triamcinolone acetonide
Dosage Form	Ointment
Route	Topical
Strength	0.05%
Market Status	Prescription
Company	Carolina Medcl

5 of 10
Drug Name	Triesence
Active Ingredient	Triamcinolone acetonide
Dosage Form	Injectable
Route	Intravitreal; suspension
Strength	40mg/ml (40mg/ml); 40mgml
Market Status	Prescription
Company	Alcon; Alcon Res

6 of 10
Drug Name	Kenalog-10
Drug Label	Kenalog-10 Injection (triamcinolone acetonide injectable suspension, USP) is triamcinolone acetonide, a synthetic glucocorticoid corticosteroid with marked anti-inflammatory action, in a sterile aqueous suspension suitable for intralesional and int...
Active Ingredient	Triamcinolone acetonide
Dosage Form	Injectable
Route	Injection
Strength	10mg/ml
Market Status	Prescription
Company	Apothecon

7 of 10
Drug Name	Kenalog-40
Drug Label	Kenalog-40 Injection (triamcinolone acetonide injectable suspension, USP) is a synthetic glucocorticoid corticosteroid with anti-inflammatory action. THIS FORMULATION IS SUITABLE FOR INTRAMUSCULAR AND INTRA-ARTICULAR USE ONLY. THIS FORMULATION IS N...
Active Ingredient	Triamcinolone acetonide
Dosage Form	Injectable
Route	Injection
Strength	40mg/ml
Market Status	Prescription
Company	Apothecon

8 of 10
Drug Name	Triamcinolone acetonide
Drug Label	Triamcinolone acetonide, USP, the active ingredient in Nasacort HFA Nasal Aerosol, is a glucocorticosteroid with a molecular weight of 434.5, the chemical designation 9-Fluoro-11,16,17,21-tetrahydroxypregna-1,4-diene-3,20-dione cyclic 16,17-ace...
Active Ingredient	Triamcinolone acetonide
Dosage Form	Ointment; Spray, metered; Paste; Cream; Lotion
Route	Dental; Nasal; Topical
Strength	0.5%; 0.055mg/spray; 0.1%; 0.025%
Market Status	Prescription
Company	Wockhardt; Taro; Lyne; Fougera Pharms; Teva Pharms; Versapharm; Vintage; Perrigo New York; Wockhardt Eu Operatn

9 of 10
Drug Name	Triamcinolone acetonide in absorbase
Drug Label	TRIESENCE (triamcinolone acetonide injectable suspension) 40 mg/mL is a synthetic corticosteroid with anti-inflammatory action. Each mL of the sterile, aqueous suspension provides 40 mg of triamcinolone acetonide, with sodium chloride for isotonici...
Active Ingredient	Triamcinolone acetonide
Dosage Form	Ointment
Route	Topical
Strength	0.05%
Market Status	Prescription
Company	Carolina Medcl

10 of 10
Drug Name	Triesence
Active Ingredient	Triamcinolone acetonide
Dosage Form	Injectable
Route	Intravitreal; suspension
Strength	40mg/ml (40mg/ml); 40mgml
Market Status	Prescription
Company	Alcon; Alcon Res

4.2 Drug Indication

Visualisation during vitrectomy

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Anti-Inflammatory Agents

Substances that reduce or suppress INFLAMMATION. (See all compounds classified as Anti-Inflammatory Agents.)

Glucocorticoids

A group of CORTICOSTEROIDS that affect carbohydrate metabolism (GLUCONEOGENESIS, liver glycogen deposition, elevation of BLOOD SUGAR), inhibit ADRENOCORTICOTROPIC HORMONE secretion, and possess pronounced anti-inflammatory activity. They also play a role in fat and protein metabolism, maintenance of arterial blood pressure, alteration of the connective tissue response to injury, reduction in the number of circulating lymphocytes, and functioning of the central nervous system. (See all compounds classified as Glucocorticoids.)

Immunosuppressive Agents

Agents that suppress immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-CELLS or by inhibiting the activation of HELPER CELLS. While immunosuppression has been brought about in the past primarily to prevent rejection of transplanted organs, new applications involving mediation of the effects of INTERLEUKINS and other CYTOKINES are emerging. (See all compounds classified as Immunosuppressive Agents.)

5.2 FDA Pharmacological Classification

5.2.1 Active Moiety

TRIAMCINOLONE ACETONIDE

5.2.2 FDA UNII

F446C597KA

5.2.3 Pharmacological Classes

Corticosteroid [EPC]; Corticosteroid Hormone Receptor Agonists [MoA]