List of Certificates of Suitability (CEPs) for NCGC00024866-03 Active Pharmaceutical Ingredient issued by the EDQM and listed on PharmaCompass.com

NCGC00024866-03

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8EXCIPIENTS BY APPLICATIONS

Chemistry

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Also known as: 1508-75-4, Mydriacyl, Mydriaticum, Bistropamide, Tropicacyl, Visumidriatic

Molecular Formula

C₁₇H₂₀N₂O₂

Molecular Weight

284.35 g/mol

InChI Key

BGDKAVGWHJFAGW-UHFFFAOYSA-N

FDA UNII

N0A3Z5XTC6

One of the MUSCARINIC ANTAGONISTS with pharmacologic action similar to ATROPINE and used mainly as an ophthalmic parasympatholytic or mydriatic.

Tropicamide is an Anticholinergic. The mechanism of action of tropicamide is as a Cholinergic Antagonist.

1 2D Structure

Tropicamide

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

N-ethyl-3-hydroxy-2-phenyl-N-(pyridin-4-ylmethyl)propanamide

2.1.2 InChI

InChI=1S/C17H20N2O2/c1-2-19(12-14-8-10-18-11-9-14)17(21)16(13-20)15-6-4-3-5-7-15/h3-11,16,20H,2,12-13H2,1H3

2.1.3 InChI Key

BGDKAVGWHJFAGW-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CCN(CC1=CC=NC=C1)C(=O)C(CO)C2=CC=CC=C2

2.2 Other Identifiers

2.2.1 UNII

N0A3Z5XTC6

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Colircusi Tropicamida

2. Minims Tropicamide

3. Mydral

4. Mydriafair

5. Mydriaticum

6. Mydrum

7. N-ethyl-alpha-(hydroxymethyl)-n-(4-pyridinylmethyl)benzeneacetamide

8. N-ethyl-n-(4-pyridylmethyl)tropamide

9. Ocu Tropic

10. Ocu-tropic

11. Ocutropic

12. Tropicacyl

13. Tropicamide Faure

14. Tropicamide Minims

15. Tropicamide Monofree

16. Tropicamide Monohydrochloride, (r)-isomer

17. Tropicamide Monohydrochloride, (s)-isomer

18. Tropicamide, (+-)-isomer

19. Tropicamide, (r)-isomer

20. Tropicamide, (s)-isomer

2.3.2 Depositor-Supplied Synonyms

1. 1508-75-4

2. Mydriacyl

3. Mydriaticum

4. Bistropamide

5. Tropicacyl

6. Visumidriatic

7. N-ethyl-3-hydroxy-2-phenyl-n-(pyridin-4-ylmethyl)propanamide

8. Tropicamidum

9. Ro 1-7683

10. N-ethyl-2-phenyl-n-(4-pyridylmethyl)hydracrylamide

11. Mydriafair

12. Minims Tropicamide

13. Epitromina

14. Tropikamid

15. Mydrum

16. Nsc-757372

17. N0a3z5xtc6

18. Tropimil

19. Ncgc00016065-07

20. Tropicamida

21. Ro-1-7683

22. Benzeneacetamide, N-ethyl-.alpha.-(hydroxymethyl)-n-(4-pyridinylmethyl)-

23. Dsstox_cid_25220

24. Dsstox_rid_80757

25. Dsstox_gsid_45220

26. Tropicamidum [inn-latin]

27. Tropicamida [inn-spanish]

28. Tropicamid

29. Mydriacyl (tn)

30. N-ethyl-n-(4-pyridylmethyl)tropamid

31. N-ethyl-n-(4-pyridylmethyl)tropamide

32. Smr000058523

33. Sr-01000075351

34. Einecs 216-140-2

35. Unii-n0a3z5xtc6

36. N-ethyl-alpha-(hydroxymethyl)-n-(4-pyridinylmethyl)benzeneacetamide

37. Brn 0285563

38. Tropicamide, Solid

39. Benzeneacetamide, N-ethyl-alpha-(hydroxymethyl)-n-(4-pyridinylmethyl)-

40. Prestwick_487

41. Cas-1508-75-4

42. Component Of Paremyd

43. Mfcd00058580

44. Hydracrylamide, N-ethyl-2-phenyl-n-(4-pyridylmethyl)-

45. Tropicamide [usan:usp:inn:ban:jan]

46. (+-)-n-ethyl-2-phenyl-n-(4-pyridylmethyl)hydracrylamide

47. Spectrum_000584

48. Tropicamide [mi]

49. Prestwick0_000228

50. Prestwick1_000228

51. Prestwick2_000228

52. Prestwick3_000228

53. Spectrum2_000936

54. Spectrum3_000655

55. Spectrum4_000377

56. Spectrum5_001585

57. Tropicamide [inn]

58. Tropicamide [jan]

59. Tropicamide [usan]

60. T 9778

61. Tropicamide [vandf]

62. Tropicamide [mart.]

63. Lopac0_001223

64. Schembl23975

65. Bspbio_000275

66. Bspbio_002289

67. Kbiogr_000873

68. Kbioss_001064

69. Tropicamide [usp-rs]

70. Tropicamide [who-dd]

71. Tropicamide [who-ip]

72. 5-22-09-00359 (beilstein Handbook Reference)

73. Mls001306442

74. Mls002154240

75. Divk1c_000448

76. Spectrum1500599

77. Spbio_000872

78. Spbio_002196

79. Bpbio1_000303

80. Chebi:9757

81. Gtpl7319

82. Tropicamide (jp17/usp/inn)

83. Chembl1200604

84. Dtxsid8045220

85. Bdbm82371

86. Hms501g10

87. Kbio1_000448

88. Kbio2_001064

89. Kbio2_003632

90. Kbio2_006200

91. Kbio3_001509

92. Tropicamide [orange Book]

93. Ninds_000448

94. Hms1568n17

95. Hms1921i09

96. Hms2089m05

97. Hms2092a18

98. Hms2095n17

99. Hms2235j15

100. Hms3259m18

101. Hms3263f08

102. Hms3267a13

103. Hms3373b07

104. Hms3411f14

105. Hms3651k04

106. Hms3675f14

107. Hms3712n17

108. Hms3742c05

109. Hms3884e16

110. Pharmakon1600-01500599

111. Tropicamide [ep Monograph]

112. Tropicamide For Peak Identification

113. Tropicamide [usp Monograph]

114. Bcp13504

115. Hy-b0321

116. Nsc_5593

117. Paremyd Component Tropicamide

118. Tropicamidum [who-ip Latin]

119. Tox21_110297

120. Tox21_501223

121. Ac-816

122. Bbl028074

123. Ccg-40076

124. Nsc757372

125. S1913

126. Stk934612

127. Akos005664076

128. Tox21_110297_1

129. Am84467

130. Db00809

131. Ks-5174

132. Lp01223

133. Nc00589

134. Nsc 757372

135. Sdccgsbi-0051190.p004

136. Tropicamide Component Of Paremyd

137. Benzeneacetamide, N-ethyl-alpha-(hydroxymethyl)-n-(4-pyridinylmethyl)-, (+-)-

138. Idi1_000448

139. Smp1_000304

140. Ncgc00016065-03

141. Ncgc00016065-04

142. Ncgc00016065-05

143. Ncgc00016065-06

144. Ncgc00016065-08

145. Ncgc00016065-09

146. Ncgc00016065-11

147. Ncgc00016065-22

148. Ncgc00024866-02

149. Ncgc00024866-03

150. Ncgc00024866-04

151. Ncgc00024866-05

152. Ncgc00024866-06

153. Ncgc00261908-01

154. Cas_1508-75-4

155. Sbi-0051190.p003

156. Ab00052120

157. Eu-0101223

158. Ft-0657590

159. Sw196691-3

160. T1470

161. C72868

162. D00397

163. Q29310

164. Ab00052120-10

165. Ab00052120_11

166. Ab00052120_12

167. 508t754

168. L001262

169. N-ethyl-2-phenyl-n-(4-pyridylmethyl Hydracrylamide

170. Q-201902

171. Sr-01000075351-1

172. Sr-01000075351-3

173. Sr-01000075351-5

174. Sr-01000075351-7

175. Brd-a79672927-001-05-8

176. Brd-a79672927-001-10-8

177. Tropicamide, European Pharmacopoeia (ep) Reference Standard

178. N-ethyl-3-hydroxy-2-phenyl-n-(4-pyridinylmethyl)propanamide #

179. (+/-)-n-ethyl-2-phenyl-n-(4-pyridylmethyl)hydracrylamide

180. Tropicamide, United States Pharmacopeia (usp) Reference Standard

181. Benzeneacetamide, N-ethyl-.alpha.-(hydroxymethyl)-n-(4-pyridinylmethyl)-, (+/-)-

182. Tropicamide For Peak Identification, European Pharmacopoeia (ep) Reference Standard

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₁₇H₂₀N₂O₂
Molecular Weight	284.35 g/mol
XLogP3	1.5
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	6
Exact Mass	284.152477885 g/mol
Monoisotopic Mass	284.152477885 g/mol
Topological Polar Surface Area	53.4 Å²
Heavy Atom Count	21
Formal Charge	0
Complexity	310
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	1
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 8
Drug Name	Mydriacyl
PubMed Health	Atropine, Homatropine, and Scopolamine (Ophthalmic route)
Drug Classes	Mydriatic-Cycloplegic
Drug Label	MYDRIACYL (tropicamide ophthalmic solution, USP) is an anticholinergic prepared as a sterile topical ophthalmic solution in two strengths. The active ingredient is represented by the chemical structure:Each mL contains: Active: tropicamide 0.5% or...
Active Ingredient	Tropicamide
Dosage Form	Solution/drops
Route	Ophthalmic
Strength	0.5%; 1%
Market Status	Prescription
Company	Alcon

2 of 8
Drug Name	Paremyd
PubMed Health	Tropicamide (Into the eye)
Active Ingredient	tropicamide; Hydroxyamphetamine hydrobromide
Dosage Form	Solution/drops
Route	Ophthalmic
Strength	1%; 0.25%
Market Status	Prescription
Company	Akorn

3 of 8
Drug Name	Tropicacyl
Drug Label	MYDRIACYL (tropicamide ophthalmic solution, USP) is an anticholinergic prepared as a sterile topical ophthalmic solution in two strengths. The active ingredient is represented by the chemical structure:Each mL contains: Active: tropicamide 0.5% or...
Active Ingredient	Tropicamide
Dosage Form	Solution/drops
Route	Ophthalmic
Strength	0.5%; 1%
Market Status	Prescription
Company	Akorn

4 of 8
Drug Name	Tropicamide
Active Ingredient	Tropicamide
Dosage Form	Solution/drops
Route	Ophthalmic
Strength	0.5%; 1%
Market Status	Prescription
Company	Bausch And Lomb

5 of 8
Drug Name	Mydriacyl
PubMed Health	Atropine, Homatropine, and Scopolamine (Ophthalmic route)
Drug Classes	Mydriatic-Cycloplegic
Drug Label	MYDRIACYL (tropicamide ophthalmic solution, USP) is an anticholinergic prepared as a sterile topical ophthalmic solution in two strengths. The active ingredient is represented by the chemical structure:Each mL contains: Active: tropicamide 0.5% or...
Active Ingredient	Tropicamide
Dosage Form	Solution/drops
Route	Ophthalmic
Strength	0.5%; 1%
Market Status	Prescription
Company	Alcon

6 of 8
Drug Name	Paremyd
PubMed Health	Tropicamide (Into the eye)
Active Ingredient	tropicamide; Hydroxyamphetamine hydrobromide
Dosage Form	Solution/drops
Route	Ophthalmic
Strength	1%; 0.25%
Market Status	Prescription
Company	Akorn

7 of 8
Drug Name	Tropicacyl
Drug Label	MYDRIACYL (tropicamide ophthalmic solution, USP) is an anticholinergic prepared as a sterile topical ophthalmic solution in two strengths. The active ingredient is represented by the chemical structure:Each mL contains: Active: tropicamide 0.5% or...
Active Ingredient	Tropicamide
Dosage Form	Solution/drops
Route	Ophthalmic
Strength	0.5%; 1%
Market Status	Prescription
Company	Akorn

8 of 8
Drug Name	Tropicamide
Active Ingredient	Tropicamide
Dosage Form	Solution/drops
Route	Ophthalmic
Strength	0.5%; 1%
Market Status	Prescription
Company	Bausch And Lomb

4.2 Drug Indication

Tropicamide is indicated to induce mydriasis (dilation of the pupil) and cycloplegia (paralysis of the ciliary muscle of the eye) in diagnostic procedures. It is used in combination with [hydroxyamphetamine] for the same indication.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Tropicamide is an anticholinergic drug and that works by nonselectively blocking muscarinic receptors to cause mydriasis and cycloplegia. It relaxes the pupillary sphincter to dilate the pupil. The onset of tropicamideinduced mydriasis is about 10 to 15 minutes, with optimal effect occurring 25 to 30 minutes post-administration. Mydriasis caused by tropicamide wears off within four to eight hours, but it was seen up to 24 hours in some individuals. Tropicamide causes accommodation by causing contraction of the ciliary muscle. The cycloplegic effect occurs within 20 to minutes following administration, with a duration of action of four to 10 hours. Tropicamide can elevate intraocular pressure. The ophthalmic use of tropicamide is not typically associated with serious systemic adverse events. One randomized pilot study showed that oral tropicamide alleviated perceived symptoms of sialorrhea in patients with Parkinson's Disease: anticholinergics are believed to restore the dopaminergic to cholinergic activity imbalance in neurodegenerative diseases. Similarly in one case report, tropicamide administered via ophthalmic solution relieved clozapine-induced sialorrhea. Interestingly, in rodent models, tropicamide suppressed drug-induced tremulous jaw movements which are often used as a model of parkinsonian tremor: the significance of this finding requires further investigations.

5.2 MeSH Pharmacological Classification

Muscarinic Antagonists

Drugs that bind to but do not activate MUSCARINIC RECEPTORS, thereby blocking the actions of endogenous ACETYLCHOLINE or exogenous agonists. Muscarinic antagonists have widespread effects including actions on the iris and ciliary muscle of the eye, the heart and blood vessels, secretions of the respiratory tract, GI system, and salivary glands, GI motility, urinary bladder tone, and the central nervous system. (See all compounds classified as Muscarinic Antagonists.)

Mydriatics

Agents that dilate the pupil. They may be either sympathomimetics or parasympatholytics. (See all compounds classified as Mydriatics.)

5.3 FDA Pharmacological Classification

5.3.1 Active Moiety

TROPICAMIDE

5.3.2 FDA UNII

N0A3Z5XTC6

5.3.3 Pharmacological Classes

Cholinergic Antagonists [MoA]; Anticholinergic [EPC]

5.4 ATC Code

S01FA06

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

S - Sensory organs

S01 - Ophthalmologicals

S01F - Mydriatics and cycloplegics

S01FA - Anticholinergics

S01FA06 - Tropicamide

5.5 Absorption, Distribution and Excretion

Absorption

Following ocular administration of 40 L drops of 0.5% tropicamide in female subjects, tropicamide reached its mean peak concentration in plasma of 2.8 1.7 ng/mL (mean SD) at five minutes.

Route of Elimination

No information can be found.

Volume of Distribution

No information can be found.

Clearance

No information can be found.

5.6 Metabolism/Metabolites

No information can be found.

5.7 Biological Half-Life

Tropicamide has a plasma half-life of 30minutes.

5.8 Mechanism of Action

Muscarinic acetylcholine receptors are involved in numerous ocular functions. The M₃ subtype is predominantly expressed by smooth muscle cells of the sphincter pupillae, which is a circular muscle of the iris, and ciliary muscles. In response to light or binding of acetylcholine, M₃ receptor signalling leads to contraction of the sphincter pupillae and pupil constriction. Contraction of the ciliary muscle via M₃ receptor signalling also leads to accommodation, adjusting the lens for near vision. The eye is also innervated by parasympathetic nerves: ciliary ganglion neurons project to the ciliary body and the sphincter pupillae muscle of the iris to control ocular accommodation and pupil constriction. Tropicamide is a non-selective muscarinic antagonist that binds to all subtypes of muscarinic receptors. By binding to muscarinic receptors, tropicamide relaxes the pupillary sphincter muscle and causes pupil dilation. By blocking the muscarinic receptors of the ciliary body, tropicamide also prevents accommodation. Like other muscarinic antagonists, tropicamide inhibits the parasympathetic drive, allowing the sympathetic nervous system responses to dominate. Tropicamide is thought to ameliorate sialorrhea by blocking M₄ receptors expressed on salivary glands and reducing hypersalivation.

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