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Chemistry

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Also known as: 79794-75-5, Claritin, Alavert, Loratidine, Clarityn, Lisino
Molecular Formula
C22H23ClN2O2
Molecular Weight
382.9  g/mol
InChI Key
JCCNYMKQOSZNPW-UHFFFAOYSA-N
FDA UNII
7AJO3BO7QN

Loratadine
A second-generation histamine H1 receptor antagonist used in the treatment of allergic rhinitis and urticaria. Unlike most classical antihistamines (HISTAMINE H1 ANTAGONISTS) it lacks central nervous system depressing effects such as drowsiness.
1 2D Structure

Loratadine

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
ethyl 4-(13-chloro-4-azatricyclo[9.4.0.03,8]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-ylidene)piperidine-1-carboxylate
2.1.2 InChI
InChI=1S/C22H23ClN2O2/c1-2-27-22(26)25-12-9-15(10-13-25)20-19-8-7-18(23)14-17(19)6-5-16-4-3-11-24-21(16)20/h3-4,7-8,11,14H,2,5-6,9-10,12-13H2,1H3
2.1.3 InChI Key
JCCNYMKQOSZNPW-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CCOC(=O)N1CCC(=C2C3=C(CCC4=C2N=CC=C4)C=C(C=C3)Cl)CC1
2.2 Other Identifiers
2.2.1 UNII
7AJO3BO7QN
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 4-(8-chloro-5,6-dihydro-11h-benzo(5,6)cyclohepta(1,2-b)pyridin-11-ylidene)-1-piperidinecarboxylic Acid Ethyl Ester

2. Alavert

3. Claritin

4. Clarium

5. Sch 29851

6. Sch-29851

7. Sch29851

2.3.2 Depositor-Supplied Synonyms

1. 79794-75-5

2. Claritin

3. Alavert

4. Loratidine

5. Clarityn

6. Lisino

7. Clarityne

8. Loracert

9. Loradex

10. Bonalerg

11. Claritine

12. Fristamin

13. Histaloran

14. Lertamine

15. Lorastine

16. Sch 29851

17. Civeran

18. Loranox

19. Versal

20. Anhissen

21. Sch-29851

22. Ethyl 4-(8-chloro-5,6-dihydro-11h-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)piperidine-1-carboxylate

23. Mfcd00672869

24. Loratyne

25. Ethyl 4-(8-chloro-5,6-dihydro-11h-benzo(5,6)cyclohepta(1,2-b)pyridin-11-ylidene)-1-piperidinecarboxylate

26. Allertidin

27. Claratyne

28. Polaratyne

29. Restamine

30. Aerotina

31. Alerpriv

32. Biloina

33. Lesidas

34. Loradif

35. Lorantis

36. Loraver

37. Lorfast

38. Loritine

39. Lowadina

40. Nularef

41. Optimin

42. Sanelor

43. Sensibit

44. Sohotin

45. Velodan

46. 7ajo3bo7qn

47. Lergy

48. Pylor

49. Tadine

50. Chembl998

51. Zeos

52. Nsc-758628

53. Sinhistan Dy

54. Bedix Loratadina

55. Talorat Dy

56. Claritin Reditabs

57. Clarinase Reperabs

58. Mls000069647

59. 1-piperidinecarboxylic Acid, 4-(8-chloro-5,6-dihydro-11h-benzo(5,6)cyclohepta(1,2-b)pyridin-11-ylidene)-, Ethyl Ester

60. Ethyl 4-{13-chloro-4-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-ylidene}piperidine-1-carboxylate

61. Loratadinum [latin]

62. Claritin Reditab

63. Loratadina [spanish]

64. Clarityne-d

65. Bay76-2211

66. 1-piperidinecarboxylic Acid, 4-(8-chloro-5,6-dihydro-11h-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)-, Ethyl Ester

67. 1398065-63-8

68. Ethyl 4-(13-chloro-4-azatricyclo[9.4.0.03,8]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-ylidene)piperidine-1-carboxylate

69. Ethyl 4-(8-chloro-5,6-dihydrobenzo[1,2]cyclohepta[2,4-b]pyridin-11-ylidene)piperidine-1-carboxylate

70. Children's Claritin

71. Ncgc00015619-09

72. Loratadinum

73. Loratadina

74. Smr000058255

75. Clarityne Dy Repetabs

76. Dsstox_cid_3224

77. Dsstox_rid_76931

78. Dsstox_gsid_23224

79. Loratadine Redidose

80. Ethyl 4-(8-chloro-5,6-dihydro-11h-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)-1-piperidinecarboxylate

81. Claritin Hives Relief

82. Bactimicina Allergy

83. Claritin (tn)

84. Claritin Hives Relief Reditab

85. Cas-79794-75-5

86. Hsdb 3578

87. Sr-01000075968

88. Unii-7ajo3bo7qn

89. Cronopen

90. Flonidan

91. Klaritin

92. Loratadine-form1

93. Topcare Childrens Allergy Relief

94. Loratadinei-p25

95. Loratadine,(s)

96. Loratadine [usan:usp:inn:ban]

97. Loratadine- Bio-x

98. Loratadine-form2-he

99. Spectrum_001496

100. Tocris-1944

101. Loratadine [mi]

102. Loratadine [inn]

103. Loratadine [jan]

104. Loratadinei-0deg(l13)

105. Opera_id_1868

106. Spectrum2_001584

107. Spectrum3_000740

108. Spectrum4_000177

109. Spectrum5_001650

110. Lopac-l-9664

111. Loratadine [hsdb]

112. Loratadine [usan]

113. Loratadine-d5(ethyl-d5)

114. Loratadinei-p80(l13)

115. Loratadine [vandf]

116. L 9664

117. Loratadine [mart.]

118. Loratadinei-m100(l13)

119. Loratadinei-m173(l13)

120. Schembl4596

121. Loratadine [usp-rs]

122. Loratadine [who-dd]

123. Lopac0_000680

124. Oprea1_027965

125. Regid_for_cid_3957

126. Bspbio_002300

127. Kbiogr_000693

128. Kbioss_001976

129. Loratadine (jan/usp/inn)

130. Mls000758260

131. Mls001148466

132. Mls001423984

133. Bidd:gt0198

134. Divk1c_000792

135. Spectrum1503712

136. Spbio_001548

137. Chebi:6538

138. Gtpl7216

139. Dtxsid2023224

140. Loratadine [ep Impurity]

141. Loratadine [orange Book]

142. Bdbm22876

143. Hms502h14

144. Kbio1_000792

145. Kbio2_001976

146. Kbio2_004544

147. Kbio2_007112

148. Kbio3_001520

149. Loratadine [ep Monograph]

150. Ninds_000792

151. Hms2051g11

152. Hms2090o18

153. Hms2093i15

154. Hms2235g23

155. Hms3262g21

156. Hms3268m16

157. Hms3371d13

158. Hms3393g11

159. Hms3412n06

160. Hms3654l17

161. Hms3676n06

162. Hms3714e09

163. Loratadine [usp Monograph]

164. Pharmakon1600-01503712

165. Zinc537931

166. Loratadine 0.1 Mg/ml In Methanol

167. Act04775

168. Amy15355

169. Bcp22338

170. Tox21_110185

171. Tox21_301532

172. Tox21_500680

173. Bbl010757

174. Ccg-39362

175. Dl-436

176. Nsc721075

177. Nsc758628

178. S1358

179. Stk574925

180. Akos005499513

181. Claritin-d Component Loratadine

182. Loratadine (desloratadine Impurity E)

183. Loratadine, >=98% (hplc), Powder

184. Tox21_110185_1

185. Ab06849

186. Ac-2086

187. Bcp9000858

188. Ccg-100786

189. Cs-0887

190. Db00455

191. Ks-1079

192. Lp00680

193. Nc00036

194. Nsc 721075

195. Nsc 758628

196. Nsc-721075

197. Sdccgsbi-0050659.p004

198. Idi1_000792

199. Ncgc00015619-01

200. Ncgc00015619-02

201. Ncgc00015619-03

202. Ncgc00015619-04

203. Ncgc00015619-05

204. Ncgc00015619-06

205. Ncgc00015619-07

206. Ncgc00015619-08

207. Ncgc00015619-10

208. Ncgc00015619-11

209. Ncgc00015619-12

210. Ncgc00015619-13

211. Ncgc00015619-26

212. Ncgc00023125-02

213. Ncgc00023125-04

214. Ncgc00023125-05

215. Ncgc00023125-06

216. Ncgc00023125-07

217. Ncgc00255171-01

218. Ncgc00261365-01

219. 4-(8-chloro-5,6-dihydro-11h-benzo[5,6]cycloheptal[1,2-b]pyridin-11-ylidene-1-piperidinecarboxylic Acid Ethyl Ester

220. Bl164637

221. Hy-17043

222. Loratadine Component Of Claritin-d

223. Nci60_041473

224. Sy052751

225. Bcp0726000007

226. Sbi-0050659.p003

227. Eu-0100680

228. Ft-0627976

229. L0223

230. Sw197416-3

231. D00364

232. Ab00053224-15

233. Ab00053224-16

234. Ab00053224_17

235. Ab00053224_18

236. 794l755

237. L000667

238. Q424049

239. Q-100833

240. Sr-01000075968-1

241. Sr-01000075968-3

242. Sr-01000075968-4

243. Sr-01000075968-6

244. Brd-k82795137-001-02-3

245. Brd-k82795137-001-10-6

246. Z1741979837

247. Loratadine, British Pharmacopoeia (bp) Reference Standard

248. Loratadine, European Pharmacopoeia (ep) Reference Standard

249. Loratadine, United States Pharmacopeia (usp) Reference Standard

250. Loratadine, Pharmaceutical Secondary Standard; Certified Reference Material

251. Loratadine For System Suitability, European Pharmacopoeia (ep) Reference Standard

252. 1-piperidenecarboxylic Acid,6-duhydro-11h-benzo [5,6]cyclohepta[1,2-b]-pyridin-11-ylidene)-, Ethyl Ester

253. 1-piperidinecarboxylic Acid,4-(8-chloro-5,6-dihydro-11h-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)-, Ethyl Ester

254. 11-[n-(ethoxycarbonyl)-4-piperidylidene]-8-chloro-6,11-dihydro-5h-benzo-[5,6]cyclohepta[1,2-b]pyridine

255. 4-(8-chloro-5,6-dihydro-11h-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)-1-piperidinecarboxylic Acid Ethyl Ester

256. 4-(8-chloro-5,6-dihydro-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)-piperidine-1-carboxylic Acid Ethyl Ester

257. 4-(8-chloro-5,6-dihydrobenzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)piperidine-1-carboxylic Acid Ethyl Ester

258. 8-chloro-11-(1-ethoxycarbonyl-4-piperidylidene)-6,11-dihydro-5h-benzo[5,6]cyclohepta[1,2-b]pyridine

259. 8-chloro-6,11-dihydro-11-(1- Ethoxycarbonyl-4-piperidylidene)-5h-benzo[5,6]cyclohepta[1,2-b]pyridine

260. 8-chloro-6,11-dihydro-11-(1-ethoxycarbonyl-4-piperidylidene)-5h-benzo[5,6]cyclohepta[1,2-b]pyridine

261. Ethyl 4-(8-chloro-5,6-dihydro-11h-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidine)-1-piperidinecarboxylate

262. Loratadine Impurity C;4-(4,8-dichloro-5,6-dihydro-11h-benzo(5,6)cyclohepta(1,2-b)pyridin-11-ylidene)-1-piperidinecarboxylic Acid Ethyl Ester

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 382.9 g/mol
Molecular Formula C22H23ClN2O2
XLogP35.2
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count3
Rotatable Bond Count2
Exact Mass382.1448057 g/mol
Monoisotopic Mass382.1448057 g/mol
Topological Polar Surface Area42.4 Ų
Heavy Atom Count27
Formal Charge0
Complexity569
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 18  
Drug NameAlavert
PubMed HealthLoratadine (By mouth)
Drug ClassesRespiratory Agent
Active IngredientLoratadine
Dosage FormTablet, orally disintegrating
RouteOral
Strength10mg
Market StatusOver the Counter
CompanyPfizer

2 of 18  
Drug NameChildren's claritin
PubMed HealthLoratadine (By mouth)
Drug ClassesRespiratory Agent
Active IngredientLoratadine
Dosage FormTablet, chewable
RouteOral
Strength5mg
Market StatusOver the Counter
CompanySchering Plough

3 of 18  
Drug NameClaritin
PubMed HealthLoratadine/Pseudoephedrine (By mouth)
Drug ClassesAntihistamine, Less-Sedating/Decongestant Combination, Antihistamine/Decongestant Combination
Active IngredientLoratadine
Dosage FormTablet; Syrup; Capsule
RouteOral
Strength1mg/ml; 10mg
Market StatusOver the Counter
CompanySchering Plough

4 of 18  
Drug NameClaritin hives relief
PubMed HealthLoratadine/Pseudoephedrine (By mouth)
Drug ClassesAntihistamine, Less-Sedating/Decongestant Combination, Antihistamine/Decongestant Combination
Active IngredientLoratadine
Dosage FormTablet
RouteOral
Strength10mg
Market StatusOver the Counter
CompanySchering Plough

5 of 18  
Drug NameClaritin hives relief reditab
PubMed HealthLoratadine (By mouth)
Drug ClassesRespiratory Agent
Active IngredientLoratadine
Dosage FormTablet, orally disintegrating
RouteOral
Strength10mg
Market StatusOver the Counter
CompanySchering Plough

6 of 18  
Drug NameClaritin reditabs
Active IngredientLoratadine
Dosage FormTablet, orally disintegrating
RouteOral
Strength5mg; 10mg
Market StatusOver the Counter
CompanySchering Plough

7 of 18  
Drug NameClaritin-d
Active IngredientLoratadine; pseudoephedrine sulfate
Dosage FormTablet, extended release
RouteOral
Strength5mg; 120mg
Market StatusOver the Counter
CompanySchering Plough

8 of 18  
Drug NameLoratadine
Active IngredientLoratadine
Dosage FormTablet; Syrup; Suspension; Tablet, orally disintegrating
Routeoral; Oral
Strength1mg/ml; 10mg; 5mg/5ml
Market StatusOver the Counter
CompanyRanbaxy; Wockhardt; Silarx; Actavis Labs Fl; Teva; Apotex; Taro; Sandoz; Pfizer; Perrigo; Mylan; Impax Labs

9 of 18  
Drug NameLoratadine redidose
Active IngredientLoratadine
Dosage FormTablet, orally disintegrating
RouteOral
Strength10mg
Market StatusOver the Counter
CompanyRanbaxy

10 of 18  
Drug NameAlavert
PubMed HealthLoratadine (By mouth)
Drug ClassesRespiratory Agent
Active IngredientLoratadine
Dosage FormTablet, orally disintegrating
RouteOral
Strength10mg
Market StatusOver the Counter
CompanyPfizer

11 of 18  
Drug NameChildren's claritin
PubMed HealthLoratadine (By mouth)
Drug ClassesRespiratory Agent
Active IngredientLoratadine
Dosage FormTablet, chewable
RouteOral
Strength5mg
Market StatusOver the Counter
CompanySchering Plough

12 of 18  
Drug NameClaritin
PubMed HealthLoratadine/Pseudoephedrine (By mouth)
Drug ClassesAntihistamine, Less-Sedating/Decongestant Combination, Antihistamine/Decongestant Combination
Active IngredientLoratadine
Dosage FormTablet; Syrup; Capsule
RouteOral
Strength1mg/ml; 10mg
Market StatusOver the Counter
CompanySchering Plough

13 of 18  
Drug NameClaritin hives relief
PubMed HealthLoratadine/Pseudoephedrine (By mouth)
Drug ClassesAntihistamine, Less-Sedating/Decongestant Combination, Antihistamine/Decongestant Combination
Active IngredientLoratadine
Dosage FormTablet
RouteOral
Strength10mg
Market StatusOver the Counter
CompanySchering Plough

14 of 18  
Drug NameClaritin hives relief reditab
PubMed HealthLoratadine (By mouth)
Drug ClassesRespiratory Agent
Active IngredientLoratadine
Dosage FormTablet, orally disintegrating
RouteOral
Strength10mg
Market StatusOver the Counter
CompanySchering Plough

15 of 18  
Drug NameClaritin reditabs
Active IngredientLoratadine
Dosage FormTablet, orally disintegrating
RouteOral
Strength5mg; 10mg
Market StatusOver the Counter
CompanySchering Plough

16 of 18  
Drug NameClaritin-d
Active IngredientLoratadine; pseudoephedrine sulfate
Dosage FormTablet, extended release
RouteOral
Strength5mg; 120mg
Market StatusOver the Counter
CompanySchering Plough

17 of 18  
Drug NameLoratadine
Active IngredientLoratadine
Dosage FormTablet; Syrup; Suspension; Tablet, orally disintegrating
Routeoral; Oral
Strength1mg/ml; 10mg; 5mg/5ml
Market StatusOver the Counter
CompanyRanbaxy; Wockhardt; Silarx; Actavis Labs Fl; Teva; Apotex; Taro; Sandoz; Pfizer; Perrigo; Mylan; Impax Labs

18 of 18  
Drug NameLoratadine redidose
Active IngredientLoratadine
Dosage FormTablet, orally disintegrating
RouteOral
Strength10mg
Market StatusOver the Counter
CompanyRanbaxy

4.2 Therapeutic Uses

Anti-Allergic Agents; Antipruritics; Histamine H1 Antagonists

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


Antihistamines are indicated in the prophylactic and symptomatic treatment of perennial and seasonal allergic rhinitis, vasomotor rhinitis, and allergic conjunctivitis due to inhalant allergens and foods. /Antihistamines; Included in US product labeling/

USP Convention. USPDI - Drug Information for the Health Care Professional. 16th ed. Volume I. Rockville, MD: U.S. Pharmaceutical Convention, Inc. 1996 (Plus updates)., p. 324


Antihistamines are indicated for the symptomatic treatment of pruritus associated with allergic reactions and of mild, uncomplicated allergic skin manifestations of urticaria and angioedema, in dermatographism, and in urticaria associated with transfusions. /Antihistamines; Included in US product labeling/

USP Convention. USPDI - Drug Information for the Health Care Professional. 16th ed. Volume I. Rockville, MD: U.S. Pharmaceutical Convention, Inc. 1996 (Plus updates)., p. 324


Antihistamines are also use in the treatment of pruritus associated with pityriasis rosea. /Antihistamines; NOT included in US or Canadian product labeling/

USP Convention. USPDI - Drug Information for the Health Care Professional. 16th ed. Volume I. Rockville, MD: U.S. Pharmaceutical Convention, Inc. 1996 (Plus updates)., p. 324


For more Therapeutic Uses (Complete) data for LORATADINE (19 total), please visit the HSDB record page.


4.3 Drug Warning

Small amounts of antihistamines are distributed into breast milk; use is not recommended in nursing mothers because of the risk of adverse effects, such as unusual excitement or irritability, in infants. /Antihistamines/

USP Convention. USPDI - Drug Information for the Health Care Professional. 16th ed. Volume I. Rockville, MD: U.S. Pharmaceutical Convention, Inc. 1996 (Plus updates)., p. 327


Use is not recommended in newborn or premature infants because this age group has an increased susceptibility to anticholinergic side effects, such as central nervous system (CNS) excitation, and an increased tendency toward convulsions. /Antihistamines/

USP Convention. USPDI - Drug Information for the Health Care Professional. 16th ed. Volume I. Rockville, MD: U.S. Pharmaceutical Convention, Inc. 1996 (Plus updates)., p. 327


A paradoxical reaction characterized by hyperexcitability may occur in children taking antihistamines. /Antihistamines/

USP Convention. USPDI - Drug Information for the Health Care Professional. 16th ed. Volume I. Rockville, MD: U.S. Pharmaceutical Convention, Inc. 1996 (Plus updates)., p. 327


Dizziness, sedation, confusion, and hypotension may be more likely to occur in geriatric patients taking antihistamines. A paradoxical reaction characterized by hyperexcitability may occur in geriatric patients taking antihistamines. Geriatric patients are especially susceptible to the anticholinergic side effects, such as dryness of mouth and urinary retention (especially in males), of the antihistamines. If these side effects occur and continue or are severe, medication should probably be discontinued. /Antihistamines/

USP Convention. USPDI - Drug Information for the Health Care Professional. 16th ed. Volume I. Rockville, MD: U.S. Pharmaceutical Convention, Inc. 1996 (Plus updates)., p. 327


For more Drug Warnings (Complete) data for LORATADINE (9 total), please visit the HSDB record page.


4.4 Drug Indication

Loratadine is a 2nd generation antihistamine and is used to manage symptoms of allergic rhinitis, wheal formation, urticaria, and other allergic dermatologic conditions.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Like other 2nd generation antihistamines, loratadine is selective for peripheral H1 receptors. Loratadine does not penetrate effectively into the central nervous system and has poor affinity for CNS H1-receptors. These qualities result in a lack of CNS depressant effects such as drowsiness, sedation, and impaired psychomotor function.


5.2 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.)


Antipruritics

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


Histamine H1 Antagonists, Non-Sedating

A class of non-sedating drugs that bind to but do not activate histamine receptors (DRUG INVERSE AGONISM), thereby blocking the actions of histamine or histamine agonists. These antihistamines represent a heterogenous group of compounds with differing chemical structures, adverse effects, distribution, and metabolism. Compared to the early (first generation) antihistamines, these non-sedating antihistamines have greater receptor specificity, lower penetration of BLOOD-BRAIN BARRIER, and are less likely to cause drowsiness or psychomotor impairment. (See all compounds classified as Histamine H1 Antagonists, Non-Sedating.)


5.3 FDA Pharmacological Classification
5.3.1 Pharmacological Classes
Histamine-2 Receptor Antagonist [EPC]; Histamine H2 Receptor Antagonists [MoA]
5.4 ATC Code

R06AX13

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


R - Respiratory system

R06 - Antihistamines for systemic use

R06A - Antihistamines for systemic use

R06AX - Other antihistamines for systemic use

R06AX13 - Loratadine


5.5 Absorption, Distribution and Excretion

Absorption

Loratadine is rapidly absorbed and achieves peak plasma concentration in 1-2 hours, while it's main metabolite achieves peak plasma concentration in 3-4 hours. In the rapid dissolve formulation, the pharmacokinetic parameters of loratadine are as follows: Cmax = 2.56 ng/ml, Tmax = 1.14 hrs, AUC = 6.14 ng x hr/ml. In the rapid dissolve formulation, the pharmacokinetic parameters of descarboethoxyloratadine are as follows: Cmax = 3.72 ng/ml, Tmax = 1.97 hr, AUC = 49.1 ng x hr/ml. In the conventional formulation, the pharmacokinetic parameters of loratadine are as follows: Cmax = 2.11 ng/ml, Tmax = 1.00 hr, AUC = 4.64 ng x hr/ml In the conventional formulation, the pharmacokinetic parameters of descarboethoxyloratadine are as follows: Cmax = 3.66 ng/ml, Tmax = 1.97 hr, AUC = 48.4 ng x hr/ml


Route of Elimination

Over a 10 day period, 40% of loratadine is excreted in the urine, and 42% is eliminated in the faeces.


Volume of Distribution

The volume of distribution of loratadine is 120 L/Kg.


Clearance

The clearance of loratadine after single oral doses of 20 mg and 40 mg are 12 L/h/kg and 9 L/h/kg respectively. P-glycoprotein is involved in the clearance of many 2nd generation antihistamines, including loratadine, from the central nervous system. 1st generation antihistamines are not cleared by P-glycoprotein, which may help explain why they have a different central nervous system adverse effect profile compared to their 2nd generation counterparts. It appears that an antihistamine with higher affinity for p-glycoprotein will have a lower incidence of CNS adverse effects.


H1 antagonists are eliminated more rapidly by children than by adults and more slowly in those with severe liver disease. /H1 Receptor Antagonists/

Hardman, J.G., L.E. Limbird, P.B. Molinoff, R.W. Ruddon, A.G. Goodman (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 9th ed. New York, NY: McGraw-Hill, 1996., p. 590


The H1 antagonists are well absorbed from the gastrointestinal tract. Following oral administration, peak plasma concentrations are achieved in 2 to 3 hours ... . /H1 Receptor Antagonists/

Hardman, J.G., L.E. Limbird, P.B. Molinoff, R.W. Ruddon, A.G. Goodman (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 9th ed. New York, NY: McGraw-Hill, 1996., p. 588


Approximately 80% of the total dose administered can be found equally distributed between urine and feces in the form of metabolic products after 10 days.

PDR; Physicians' Desk Reference. 50th Ed. Montvale, NJ: Medical Economics Co. p.2349 (1996)


Whole body autoradiographic studies in rats and monkeys, radiolabeled tissue distribution studies in mice and rats, and in vivo radioligand studies in mice have shown that neither loratadine nor its metabolites readily cross the blood-brain barrier. Radioligand binding studies with guinea pig pulmonary and brain H1-receptors indicate that there was preferential binding to peripheral versus central nervous system H1-receptors.

PDR; Physicians' Desk Reference. 50th Ed. Montvale, NJ: Medical Economics Co. p.2349 (1996)


Unlike other currently available antihistamines, second generation antihistamines such as ... loratadine appear to distribute poorly or not appreciably into the CNS at usual dosages.

McEvoy G.K. (ed.). American Hospital Formulary Service-Drug Information 96. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 1996 (Plus Supplements)., p. 3


5.6 Metabolism/Metabolites

Loratadine undergoes extensive first pass metabolism in the liver and is primarily metabolized by CYP3A4, CYP2D6, CYP1A1 and CYP2C19. Less involved CYP enzymes include CYP1A2, CYP2B6, CYP2C8, CYP2C9 and CYP3A5. CYP3A4 and CYP2D6 are mainly responsible for metabolizing loratadine to descarboethoxyloratadine. This primary metabolite is 4 times more pharmacologically active than loratadine. In addition, a study demonstrates that descarboethoxyloratadine is first glucuronidated by UGT2B10, then hydroxylated by CYP2C8 to form 3-hydroxydesloratadine. Further glucuronidation of 3-hydroxydesloratadine facilitates excretion.


The second generation H1 antagonists astemizole, loratadine,and terfenadine are rapidly absorbed from the gastrointestinal tract and metabolized in the liver to active metabolites by the hepatic microsomal p450 system.

Hardman, J.G., L.E. Limbird, P.B. Molinoff, R.W. Ruddon, A.G. Goodman (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 9th ed. New York, NY: McGraw-Hill, 1996., p. 590


Pharmacokinetic studies following single and multiple oral doses of loratadine in 115 volunteers showed that loratadine is rapidly absorbed and extensively metabolized to an active metabolite (descarboethoxyloratadine).

PDR; Physicians' Desk Reference. 50th Ed. Montvale, NJ: Medical Economics Co. p.2349 (1996)


In vitro studies with human liver microsomes indicate that loratadine is metabolized to descarboethoxyloratadine predominately by p450 CYP3A4 and, to a lesser extent, by p450 CYP2D6.

PDR; Physicians' Desk Reference. 50th Ed. Montvale, NJ: Medical Economics Co. p.2349 (1996)


H1 receptor antagonists are among the many drugs that induce hepatic microsomal enzymes, and they may facilitate their own metabolism. /H1 Receptor Antagonists/

Hardman, J.G., L.E. Limbird, P.B. Molinoff, R.W. Ruddon, A.G. Goodman (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 9th ed. New York, NY: McGraw-Hill, 1996., p. 590


The non-sedating anti-histamine, loratadine ... was admin orally in the diet to mature male rats at dosages of 4, 10 and 25 mg/kg/day for 2 wk. The effects of these treatments on liver microsomal cytochrome P450 were evaluated by immunochemical and biochemical techniques, and were compared with the effects of treating rats with three different inducers of cytochrome P450, namely phenobarbital, 3-methylcholanthrene and dexamethasone. Treatment of rats with loratadine caused a dose dependent incr in the levels of P450 2Bl and 2B2, the major phenobarbital inducible P450 enzymes, as determined by Western immunoblotting. At the highest dosage tested, loratadine was less effective than phenobarbital as an inducer of 2Bl and 2B2, although the induction of these proteins could be detected immunochemically even at the lowest dosage of loratadine tested. Consistent with these observations, treatment of rats with loratadine caused a dose dependent incr in the rate of two reactions that are catalyzed predominantly by 2Bl/2, namely testosterone 16 beta-hydroxylation and 7-pentoxyresorufin O-dealkylation. At the highest dosage tested, loratadine caused a 7.3- and 8.5-fold incr in the rate of testosterone 16 beta-hydroxylation and 7-pentoxyresorufin O-dealkylation, respectively, compared with a and 45-fold incr caused by phenobarbital treatment. Treatment of rats with loratadine caused a 1.4 to 2.0-fold incr in the 2 beta-, 6 beta- and 15 beta-hydroxylation of testosterone, which was associated with a similar incr in the levels of immunoreactive P450 3Al and/or 3A2. As an inducer of P450 3Al/2, loratadine was slightly less effective than phenobarbital, and was considerably less effective than dexamethasone, which caused a 10- to 33-fold increase in testosterone 2 beta-, 6 beta- and 15 beta-hydroxylase activity. At the dosages tested, loratadine did not increase the levels of P450 lAl, the major 3-methylcholanthrene inducible P450 enzyme, as determined by Western immunoblotting. The rate of 7-ethoxyresorufin O-dealkylation, which is catalyzed predominantly by P450 lAl, incr 1.9-fold after loratidine treatment, but this incr was less than that caused by phenobarbital treatment (2.2-fold), and was considerably less than that caused by 3-methylcholanthrene treatment (33-fold). The effects of treating mature male mice with loratadine on liver microsomal cytochrome P450 resembled the effects observed in rats. These results indicate that loratadine is a phenobarbital type inducer of liver microsomal cytochrome P450 in rats and mice.

PMID:1534660 Parkinson A, et al; Biochem Pharmacol 43 (10): 2169-80 (1992)


Loratadine has known human metabolites that include Desloratadine.

S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560


5.7 Biological Half-Life

The elimination half life is approximately 10 hours for loratadine and 20 hours for descarboethoxyloratadine.


The mean elimination half-lives found in studies in normal adult subjects (n= 54) were 8.4 hours (range= 3 to 20 hours) for loratadine and 28 hours (range= 8.8 to 92 hours) for the major active metabolites (descarboethoxyloratadine).

PDR; Physicians' Desk Reference. 50th Ed. Montvale, NJ: Medical Economics Co. p.2349 (1996)


5.8 Mechanism of Action

Histamine release is a key mediator in allergic rhinitis and urticaria. As a result, loratadine exerts it's effect by targeting H1 histamine receptors. Loratadine binds to H1 histamine receptors found on the surface of epithelial cells, endothelial cells, eosinophils, neutrophils, airway cells, and vascular smooth muscle cells among others. H1 histamine receptors fall under the wider umbrella of G-protein coupled receptors, and exist in a state of equilibrium between the active and inactive forms. Histamine binding to the H1-receptor facilitates cross linking between transmembrane domains III and V, stabilizing the active form of the receptor. On the other hand, antihistamines bind to a different site on the H1 receptor favouring the inactive form. Hence, loratadine can more accurately be classified as an "inverse agonist" as opposed to a "histamine antagonist", and can prevent or reduce the severity of histamine mediated symptoms.


All of the available H1 receptor antagonists are reversible, competitive inhibitors of the interaction of histamine with H1 receptors. /H1 Receptor Antagonists/

Hardman, J.G., L.E. Limbird, P.B. Molinoff, R.W. Ruddon, A.G. Goodman (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 9th ed. New York, NY: McGraw-Hill, 1996., p. 587


H1 antagonists inhibit most responses of smooth muscle to histamine. /H1 Antagonists Receptors/

Hardman, J.G., L.E. Limbird, P.B. Molinoff, R.W. Ruddon, A.G. Goodman (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 9th ed. New York, NY: McGraw-Hill, 1996., p. 587


Within the vascular tree, the H1 antagonists inhibit both the vasoconstrictor effects of histamine and, to a degree, the more rapid vasodilator effects that are mediated by H1 receptors on endothelial cells. /H1 Receptor Antagonists/

Hardman, J.G., L.E. Limbird, P.B. Molinoff, R.W. Ruddon, A.G. Goodman (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 9th ed. New York, NY: McGraw-Hill, 1996., p. 588


H1 antagonists strongly block the action of histamine that results in increased capillary permeability and formation of edema and wheal. /H1 Receptor Antagonists/

Hardman, J.G., L.E. Limbird, P.B. Molinoff, R.W. Ruddon, A.G. Goodman (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 9th ed. New York, NY: McGraw-Hill, 1996., p. 588


For more Mechanism of Action (Complete) data for LORATADINE (6 total), please visit the HSDB record page.


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01-Jan-2021
31-Aug-2024
KGS
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Average Price (USD/KGS)

Number of Transactions

Total Quantity (KGS)

Total Value (USD)

Quantity (KGS) & Unit rate (USD/KGS) over time

API Imports and Exports

Importing Country Total Quantity
(KGS)
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(USD/KGS)
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DRUG PRODUCT COMPOSITIONS

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DOSAGE - TABLET;ORAL - 10MG

USFDA APPLICATION NUMBER - 19658

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DOSAGE - TABLET, EXTENDED RELEASE;ORAL - 5MG;...DOSAGE - TABLET, EXTENDED RELEASE;ORAL - 5MG;120MG

USFDA APPLICATION NUMBER - 19670

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DOSAGE - TABLET, EXTENDED RELEASE;ORAL - 10MG...DOSAGE - TABLET, EXTENDED RELEASE;ORAL - 10MG;240MG

USFDA APPLICATION NUMBER - 20470

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DOSAGE - SYRUP;ORAL - 1MG/ML

USFDA APPLICATION NUMBER - 20641

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DOSAGE - TABLET, ORALLY DISINTEGRATING;ORAL -...DOSAGE - TABLET, ORALLY DISINTEGRATING;ORAL - 10MG

USFDA APPLICATION NUMBER - 20704

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DOSAGE - CAPSULE;ORAL - 10MG

USFDA APPLICATION NUMBER - 21952

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