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2D Structure
Also known as: 58-33-3, Promethazine hcl, Phenergan, N,n-dimethyl-1-(10h-phenothiazin-10-yl)propan-2-amine hydrochloride, Fenergan, Remsed
Molecular Formula
C17H21ClN2S
Molecular Weight
320.9  g/mol
InChI Key
XXPDBLUZJRXNNZ-UHFFFAOYSA-N
FDA UNII
R61ZEH7I1I

A phenothiazine derivative with histamine H1-blocking, antimuscarinic, and sedative properties. It is used as an antiallergic, in pruritus, for motion sickness and sedation, and also in animals.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
N,N-dimethyl-1-phenothiazin-10-ylpropan-2-amine;hydrochloride
2.1.2 InChI
InChI=1S/C17H20N2S.ClH/c1-13(18(2)3)12-19-14-8-4-6-10-16(14)20-17-11-7-5-9-15(17)19;/h4-11,13H,12H2,1-3H3;1H
2.1.3 InChI Key
XXPDBLUZJRXNNZ-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CC(CN1C2=CC=CC=C2SC3=CC=CC=C31)N(C)C.Cl
2.2 Other Identifiers
2.2.1 UNII
R61ZEH7I1I
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Atosil

2. Diphergan

3. Diprazin

4. Hydrochloride, Promethazine

5. Isopromethazine

6. Phenargan

7. Phenergan

8. Phensedyl

9. Pipolfen

10. Pipolphen

11. Proazamine

12. Promet

13. Prometazin

14. Promethazine

15. Prothazin

16. Pyrethia

17. Remsed

18. Rumergan

2.3.2 Depositor-Supplied Synonyms

1. 58-33-3

2. Promethazine Hcl

3. Phenergan

4. N,n-dimethyl-1-(10h-phenothiazin-10-yl)propan-2-amine Hydrochloride

5. Fenergan

6. Remsed

7. Promethazine (hydrochloride)

8. Diprasine

9. Diprazin

10. Fellozine

11. Pipolfen

12. Pipolphen

13. Ganphen

14. Plletia

15. Prometh Fortis

16. Prometh Plain

17. Promethazine.hcl

18. Mymethazine Fortis

19. Anergan 25

20. Promethacon

21. Promethegan

22. Romergan

23. Promethazine Chloride

24. Promethiazin

25. Zipan-25

26. V Gan

27. Lergigan

28. Pyrethia

29. Zipan-50

30. Promethazine Monohydrochloride

31. Hl 8700

32. N-(2-dimethylaminopropyl-1)phenothiazine Hydrochloride

33. 10-[2-(dimethylamino)propyl]phenothiazine Hydrochloride

34. N,n-dimethyl-1-phenothiazin-10-ylpropan-2-amine;hydrochloride

35. N-(2'-dimethylamino-2'-methyl)ethylphenothiazine Hydrochloride

36. R61zeh7i1i

37. 10-(3-dimethylaminoisopropyl)phenothiazine Hydrochloride

38. 3277 R.p.

39. Mls000069398

40. 10-(2-dimethylamino-1-propyl)phenothiazine Hydrochloride

41. Chebi:8462

42. Farganesse

43. Avomine

44. Nsc-231688

45. 58-33-3 (hcl)

46. Allerfen

47. Duplamin

48. Frinova

49. Goodnight

50. Hibechin

51. Histantil

52. Kinetosin

53. Phenadoz

54. Phencen

55. Primine

56. Promantine

57. Promine

58. Proneurin

59. Smr000058379

60. Soporil

61. Bonnox

62. Closin

63. Dorme

64. Prome

65. (+-)-10-(2-(dimethylamino)propyl)phenothiazine Monohydrochloride

66. Eusedon Mono

67. Phenergan Fortis

68. Dsstox_cid_1192

69. Pms Promethazine

70. Promethazine Plain

71. Dsstox_rid_76002

72. Dsstox_gsid_21192

73. 1435933-86-0

74. Anergan 50

75. Promethazine Hydrochloride 100 Microg/ml In Acetonitrile

76. Phenergan Plain

77. Promethiazin [german]

78. Ccris 5873

79. Phenergan Hydrochloride

80. Promethazine Hydrochloride [jan]

81. Promethazinehydrochloride

82. Einecs 200-375-2

83. Mfcd00012652

84. Unii-r61zeh7i1i

85. Nsc 231688

86. Genphen

87. Sr-01000002993

88. Phanergan D

89. Phenergan (tn)

90. Promethegan (tn)

91. 10-(2-dimethylaminopropyl)phenothiazine Hydrochloride

92. Component Of Mepergan

93. Promethazine Hydrochloride [usp:jan]

94. Promethazine-d3 Hcl

95. 10-(2-(dimethylamino)propyl)phenothiazine Monohydrochloride

96. Cpd000058379

97. Phenothiazine, 10-(2-(dimethylamino)-propyl)-, Hydrochloride

98. Pronase [jan]

99. Promethazine Hydrochlorine

100. Cas-58-33-3

101. Opera_id_1745

102. 10h-phenothiazine-10-ethanamine, N,n,alpha-trimethyl-, Monohydrochloride

103. Diprazinum [who-ip]

104. Schembl41904

105. Mls001074184

106. Mls002548850

107. Spectrum1500510

108. Chembl1200750

109. Dtxsid3021192

110. Promethazine Hydrochloride Solution

111. Hms1570b18

112. Hms1920l16

113. Pharmakon1600-01500510

114. Hy-b0781

115. N,n-dimethyl-1-phenothiazin-10-yl-propan-2-amine Hydrochloride

116. Phenothiazine, 10-(2-(dimethylamino)propyl)-, Monohydrochloride

117. Promethazine For Peak Identification

118. Tox21_202264

119. Tox21_302878

120. Tox21_500899

121. Nsc231688

122. Nsc757301

123. S4293

124. 10h-phenothiazine-10-ethanamine, N,n,.alpha.-trimethyl-, Monohydrochloride

125. Akos016339657

126. Ccg-207895

127. Cs-3543

128. Ks-1385

129. Lp00899

130. Nc00471

131. Nsc-757301

132. Promethazine Hydrochloride (jp17/usp)

133. Promethazine Hydrochloride [mi]

134. Rp-3389

135. 10h-phenothiazine-10-ethanamine, N,n,alpha-trimethyl-, Monohydrochloride, (+-)-

136. Ncgc00089735-04

137. Ncgc00094215-01

138. Ncgc00094215-02

139. Ncgc00094215-03

140. Ncgc00094215-04

141. Ncgc00094215-05

142. Ncgc00256588-01

143. Ncgc00259813-01

144. Ncgc00261584-01

145. Ac-12482

146. Bp166198

147. Promethazine Hydrochloride [mart.]

148. Promethazine Hydrochloride [vandf]

149. Promethazine Hydrochloride [usp-rs]

150. Promethazine Hydrochloride [who-dd]

151. Promethazine Hydrochloride [who-ip]

152. Db-053186

153. Eu-0100899

154. P2029

155. Sw197234-3

156. D00480

157. D92182

158. P 4651

159. Promethazine Hydrochloride [orange Book]

160. Promethazine Hydrochloride [ep Monograph]

161. Promethazine Hydrochloride [usp Impurity]

162. Wln: T C666 Bn Isj B1y1&n1&1 &gh

163. A831833

164. Promethazine Hydrochloride [usp Monograph]

165. Promethazini Hydrochloridum [who-ip Latin]

166. Mepergan Component Promethazine Hydrochloride

167. Sr-01000002993-2

168. Sr-01000002993-7

169. W-105399

170. Promethazine Hydrochloride Component Of Mepergan

171. Q27108086

172. F0138-3355

173. Phenergan Vc Component Promethazine Hydrochloride

174. Pherazine Dm Component Promethazine Hydrochloride

175. Pherazine Vc Component Promethazine Hydrochloride

176. Z1259273234

177. ((c)i)-promethazine-d4 Hcl (phenothiazine-1,3,7,9-d4)

178. Promethazine Dm Component Promethazine Hydrochloride

179. Promethazine Hydrochloride Component Of Phenergan Vc

180. Promethazine Hydrochloride Component Of Pherazine Dm

181. Promethazine Hydrochloride Component Of Pherazine Vc

182. Promethazine Vc Component Promethazine Hydrochloride

183. N,n-dimethyl-1-(10-phenothiazinyl)-2-propanamine Hydrochloride

184. N-(2'-dimethylamino-2'-methylaethyl)-phenothiazin Hydrochlorid

185. N-(2'-dimethylamino-2-methylethyl)phenothiazine Hydrochloride

186. Promethazine Hydrochloride Component Of Promethazine Dm

187. Promethazine Hydrochloride Component Of Promethazine Vc

188. Promethazine Hydrochloride, Vetranal(tm), Analytical Standard

189. N,n-dimethyl-1-phenothiazin-10-ylpropan-2-amine;hydron;chloride

190. (+/-)-10-(2-(dimethylamino)propyl)phenothiazine Monohydrochloride

191. 10h-phenothiazine-10-ethanamine,n,.alpha.-trimethyl-, Monohydrochloride

192. Dimethyl[1-(10h-phenothiazin-10-yl)propan-2-yl]amine Hydrochloride

193. N,n-dimethyl-1-(10h-phenothiazin-10-yl)-2-propanamine Hydrochloride

194. Promethazine Hydrochloride 1.0 Mg/ml In Dimethyl Sulfoxide (as Free Base)

195. Promethazine Hydrochloride, European Pharmacopoeia (ep) Reference Standard

196. Promethazine Hydrochloride, Vial Of 25 Mg, Certified Reference Material

197. 10h-phenothiazine-10-ethanamine, N,n,.alpha.-trimethyl-, Monohydrochloride, (+/-)-

198. 10h-phenothiazine-10-ethanamine, N,n,alpha-trimethyl-, Hydrochloride (1:1)

199. Promethazine For Peak Identification, European Pharmacopoeia (ep) Reference Standard

200. Promethazine Hydrochloride, Pharmaceutical Secondary Standard; Certified Reference Material

201. Promethazine Hydrochloride, United States Pharmacopeia (usp) Reference Standard

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 320.9 g/mol
Molecular Formula C17H21ClN2S
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count3
Rotatable Bond Count3
Exact Mass320.1113975 g/mol
Monoisotopic Mass320.1113975 g/mol
Topological Polar Surface Area31.8 Ų
Heavy Atom Count21
Formal Charge0
Complexity298
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count2
4 Drug and Medication Information
4.1 Drug Information
1 of 4  
Drug NamePromethazine hydrochloride
Drug LabelDESCRIPTIONPromethazine hydrochloride is a racemic compound.Promethazine hydrochloride, a phenothiazine derivative, is designated chemically as 10H-Phenothiazine-10-ethanamine, N,N,-trimethyl-, monohydrochloride, ()-with the following structural...
Active IngredientPromethazine hydrochloride
Dosage FormTablet; Syrup; Suppository; Injectable
RouteRectal; Injection; Oral
Strength25mg; 50mg/ml; 25mg/ml; 6.25mg/5ml; 50mg; 12.5mg
Market StatusPrescription
CompanyVintage Pharms; Amneal Pharms; Wockhardt; Hospira; Sun Pharm Inds; Teva Pharms Usa; Taro; Sandoz; Watson Labs; Amneal Pharms Ny; Hi Tech Pharma; Caraco; Hikma Maple; Kvk Tech; X-gen Pharms; Vintage; Emcure Pharms Usa; Perrigo New York; Luitpold; Zydus Pha

2 of 4  
Drug NamePromethazine plain
Active IngredientPromethazine hydrochloride
Dosage FormSyrup
RouteOral
Strength6.25mg/5ml
Market StatusPrescription
CompanyWockhardt

3 of 4  
Drug NamePromethazine hydrochloride
Drug LabelDESCRIPTIONPromethazine hydrochloride is a racemic compound.Promethazine hydrochloride, a phenothiazine derivative, is designated chemically as 10H-Phenothiazine-10-ethanamine, N,N,-trimethyl-, monohydrochloride, ()-with the following structural...
Active IngredientPromethazine hydrochloride
Dosage FormTablet; Syrup; Suppository; Injectable
RouteRectal; Injection; Oral
Strength25mg; 50mg/ml; 25mg/ml; 6.25mg/5ml; 50mg; 12.5mg
Market StatusPrescription
CompanyVintage Pharms; Amneal Pharms; Wockhardt; Hospira; Sun Pharm Inds; Teva Pharms Usa; Taro; Sandoz; Watson Labs; Amneal Pharms Ny; Hi Tech Pharma; Caraco; Hikma Maple; Kvk Tech; X-gen Pharms; Vintage; Emcure Pharms Usa; Perrigo New York; Luitpold; Zydus Pha

4 of 4  
Drug NamePromethazine plain
Active IngredientPromethazine hydrochloride
Dosage FormSyrup
RouteOral
Strength6.25mg/5ml
Market StatusPrescription
CompanyWockhardt

5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Anti-Allergic Agents

Agents that are used to treat allergic reactions. Most of these drugs act by preventing the release of inflammatory mediators or inhibiting the actions of released mediators on their target cells. (From AMA Drug Evaluations Annual, 1994, p475) (See all compounds classified as Anti-Allergic Agents.)


Histamine H1 Antagonists

Drugs that selectively bind to but do not activate histamine H1 receptors, thereby blocking the actions of endogenous histamine. Included here are the classical antihistaminics that antagonize or prevent the action of histamine mainly in immediate hypersensitivity. They act in the bronchi, capillaries, and some other smooth muscles, and are used to prevent or allay motion sickness, seasonal rhinitis, and allergic dermatitis and to induce somnolence. The effects of blocking central nervous system H1 receptors are not as well understood. (See all compounds classified as Histamine H1 Antagonists.)


Antipruritics

Agents, usually topical, that relieve itching (pruritus). (See all compounds classified as Antipruritics.)


5.2 FDA Pharmacological Classification
5.2.1 Pharmacological Classes
Phenothiazines [CS]; Phenothiazine [EPC]