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Chemistry

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Also known as: 100643-71-8, Clarinex, Descarboethoxyloratadine, Desloratidine, Neoclarityn, Aerius
Molecular Formula
C19H19ClN2
Molecular Weight
310.8  g/mol
InChI Key
JAUOIFJMECXRGI-UHFFFAOYSA-N
FDA UNII
FVF865388R

Desloratadine
Desloratadine is a long-acting piperidine derivate with selective H1 antihistaminergic and non-sedating properties. Desloratadine diminishes the typical histaminergic effects on H1-receptors in bronchial smooth muscle, capillaries and gastrointestinal smooth muscle, including vasodilation, bronchoconstriction, increased vascular permeability, pain, itching and spasmodic contractions of gastrointestinal smooth muscle. Desloratadine is used to provide symptomatic relieve of allergic symptoms.
Desloratadine is a Histamine-1 Receptor Antagonist. The mechanism of action of desloratadine is as a Histamine H1 Receptor Antagonist.
1 2D Structure

Desloratadine

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
13-chloro-2-piperidin-4-ylidene-4-azatricyclo[9.4.0.03,8]pentadeca-1(11),3(8),4,6,12,14-hexaene
2.1.2 InChI
InChI=1S/C19H19ClN2/c20-16-5-6-17-15(12-16)4-3-14-2-1-9-22-19(14)18(17)13-7-10-21-11-8-13/h1-2,5-6,9,12,21H,3-4,7-8,10-11H2
2.1.3 InChI Key
JAUOIFJMECXRGI-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C1CC2=C(C=CC(=C2)Cl)C(=C3CCNCC3)C4=C1C=CC=N4
2.2 Other Identifiers
2.2.1 UNII
FVF865388R
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Aerius

2. Clarinex

3. Descarboethoxyloratadine

4. Descarboethoxyloratadine Acetate

5. Neoclarityn

6. Sch 34117

7. Sch-34117

2.3.2 Depositor-Supplied Synonyms

1. 100643-71-8

2. Clarinex

3. Descarboethoxyloratadine

4. Desloratidine

5. Neoclarityn

6. Aerius

7. Azomyr

8. Sch-34117

9. Denosin

10. Allex

11. Opulis

12. Sch 34117

13. 8-chloro-11-piperidin-4-ylidene-6,11-dihydro-5h-benzo[5,6]cyclohepta[1,2-b]pyridine

14. Descarboethoxyoratidine

15. Desloratadine Actavis

16. Dasselta

17. Desloratadine Teva

18. Mfcd00871949

19. 8-chloro-11-(piperidin-4-ylidene)-6,11-dihydro-5h-benzo[5,6]cyclohepta[1,2-b]pyridine

20. Nsc-759824

21. Chembl1172

22. Loratadine Related Compound A

23. 8-chloro-6,11-dihydro-11-(4-piperidinylidene)-5h-benzo(5,6)cyclohepta(1,2-b)pyridine

24. Mls000559042

25. Chebi:291342

26. Fvf865388r

27. Nsc675447

28. 5h-benzo[5,6]cyclohepta[1,2-b]pyridine, 8-chloro-6,11-dihydro-11-(4-piperidinylidene)-

29. 13-chloro-2-piperidin-4-ylidene-4-azatricyclo[9.4.0.03,8]pentadeca-1(11),3(8),4,6,12,14-hexaene

30. Ncgc00159325-02

31. Smr000149358

32. Desloratadine [usan]

33. Clarinex Reditabs

34. 8-chloro-6,11-dihydro-11-(4-piperidinylidene)-5h-benzo[5,6]cyclohepta[1,2-b]pyridine

35. Dsstox_cid_24196

36. Dsstox_rid_80112

37. Dsstox_gsid_44196

38. Desalex

39. 5h-benzo(5,6)cyclohepta(1,2-b)pyridine, 8-chloro-6,11-dihydro-11-(4-piperidinylidene)-

40. 8-chloro-11-piperidin-4-ylidene-5,6-dihydrobenzo[1,2]cyclohepta[2,4-b]pyridine

41. 8-chloro-6,11-dihydro-11-(4-piperdinylidene)- 5h-benzo[5,6]cyclohepta[1,2-b]pyridine

42. Clarinex (tn)

43. 13-chloro-2-(piperidin-4-ylidene)-4-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3(8),4,6,12,14-hexaene

44. 8-chloro-11-(piperidin-4-ylidene)-6,11-dihydro-5h-benzo[5,6]cyclohepta[1,2-b]pyridine (descarboethoxyloratadine; Desloratadine)

45. Cas-100643-71-8

46. Sr-01000668962

47. Unii-fvf865388r

48. Desloratadine [usan:inn:ban]

49. 4-(8-chloro-5,6-dihydro-11h-benzo[5,6]cyclohepta(1,2-b]pyridin-11-ylidene)-piperidine

50. 4-(8-chloro-5,6-dihydro-11h-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)piperidine

51. 4-{8-chloro-5,6-dihydro-11h-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene}-piperidine

52. 4-{8-chloro-5,6-dihydro-11h-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene}piperidine

53. Desloratadine-[d7]

54. Desloratadine- Bio-x

55. Mk-4117

56. Cpd000149358

57. Opera_id_1891

58. Desloratadine [mi]

59. Desloratadine [inn]

60. Desloratadine [jan]

61. Schembl4425

62. Desloratadine [vandf]

63. Mls000759406

64. Mls001201801

65. Mls001424247

66. Desloratadine [mart.]

67. Sch34117

68. Desloratadine Ratiopharm

69. Desloratadine [usp-rs]

70. Desloratadine [who-dd]

71. Desloratadine (jan/usp/inn)

72. Gtpl7157

73. Zinc1261

74. Desloratadine [ema Epar]

75. Dtxsid1044196

76. Loratadine Related Compound A Rs

77. Hms2052h05

78. Hms2090c06

79. Hms2093f19

80. Hms3394h05

81. Hms3652o15

82. Hms3715j15

83. Hms3885c18

84. Pharmakon1600-01505393

85. Desloratadine [orange Book]

86. Albb-027276

87. Bcp02340

88. Desloratadine For System Suitability

89. Hy-b0539

90. Desloratadine [ep Monograph]

91. Tox21_111574

92. Bbl010777

93. Bdbm50073179

94. Desloratadine [usp Monograph]

95. Nsc759824

96. S4012

97. Stk586537

98. Akos000280921

99. Tox21_111574_1

100. Ac-1279

101. Ccg-101162

102. Db00967

103. Ks-1048

104. Nc00412

105. Nsc 675447

106. Nsc 759824

107. Nsc-675447

108. Sb17503

109. Clarinex-d Component Desloratadine

110. Desloratadine 100 Microg/ml In Methanol

111. Desloratadine, Powder, >=98% (hplc)

112. Ncgc00159325-03

113. Ncgc00159325-04

114. Ncgc00159325-05

115. Bd164361

116. Loratadine Ep Impurity D (desloratadine)

117. Sbi-0206828.p001

118. Loratadine Impurity D [ep Impurity]

119. D3787

120. Desloratadine Component Of Clarinex-d

121. Ft-0602522

122. Ft-0666048

123. Sw197792-3

124. A19515

125. D03693

126. H11943

127. Loratadine Related Compound A [usp-rs]

128. Ab00456701-11

129. Ab00456701-13

130. Ab00456701_14

131. Ab00456701_15

132. 643d718

133. L001025

134. Q418060

135. Loratadine Related Compound A [usp Impurity]

136. Q-200936

137. Rupatadine Fumarate Impurity B [ep Impurity]

138. Sr-01000668962-4

139. Sr-01000668962-5

140. Sr-01000668962-8

141. Brd-k82357231-001-13-4

142. Desloratadine Teva (authorized: Rhinitis, Urticaria)

143. Desloratadine Actavis (authorized: Rhinitis, Urticaria)

144. Desloratadine, European Pharmacopoeia (ep) Reference Standard

145. Desloratadine Ratiopharm (authorized: Rhinitis, Urticaria)

146. Desloratadine, United States Pharmacopeia (usp) Reference Standard

147. 4-(8-chloro-5,6-dihydro-11 H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)piperidine

148. 4-(8-chloro-5,6-dihydro-11h-benzo-[5,6]cyclohepta(1,2-b]pyridin-11-ylidene)-piperidine

149. 4-(8-chloro-5,6-dihydro-11h-benzo[5,6]cyclohepta [1,2-b]pyridin-11-ylidene) Piperidine

150. 4-(8-chloro-5,6-dihydro-11h-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene) Piperidine

151. 8-chloro-11-(4-piperidinylidene)-6,11-dihydro-5h- Benzo[4,5]cyclohepta[2,1-b]pyridine

152. 8-chloro-11-(4-piperidyliden)-6,11-dihydro-5h-benzo[5,6]cyclohepta [1,2-b]pyridine

153. 8-chloro-11-(4-piperidyliden)-6,11-dihydro-5h-benzo[5,6]cyclohepta[1,2-b]pyridine

154. 8-chloro-11-(4-piperidylidene)-6,11-dihydro-5h-benzo[5.6]cyclohepta[1,2-b]pyridine

155. 8-chloro-6,11-dihydro-11-(4-piperidylidene)-5h-benzo[5,6]cyclohepta[1,2-b]pyridine

156. Desloratadine For System Suitability, European Pharmacopoeia (ep) Reference Standard

157. Desloratidine, Pharmaceutical Secondary Standard; Certified Reference Material

158. Loratadine Related Compound A, United States Pharmacopeia (usp) Reference Standard

159. 13-chloro-2-(piperidin-4-ylidene)-4-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3,5,7,12,14-hexaene

160. 8-chloro-11-(4-piperidylidene)-6,11-dihydro-5h-benzo[5,6]cyclohepta[1,2-b]pyridine

161. 8-chloro-6,11-dihydro-11(4-piperidylidene)-5h-benzo(5,6)cyclohepta(1,2-b) Pyridine

162. 8-chloro-6,11-dihydro-11-(4-piperidinylidene)-5h-benzo(5,6)cyclohepta(1,2-bpyridine

163. 8-chloro-6,11-dihydro-11-(4-piperidinylidene)-5h-benzo(5,6)cyclohepta(1,2b)pyridine

2.4 Create Date
2005-03-26
3 Chemical and Physical Properties
Molecular Weight 310.8 g/mol
Molecular Formula C19H19ClN2
XLogP34.5
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count2
Rotatable Bond Count0
Exact Mass310.1236763 g/mol
Monoisotopic Mass310.1236763 g/mol
Topological Polar Surface Area24.9 Ų
Heavy Atom Count22
Formal Charge0
Complexity425
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 4  
Drug NameClarinex
PubMed HealthDesloratadine (By mouth)
Drug ClassesRespiratory Agent
Drug LabelCLARINEX (desloratadine) Tablets are light blue, round, film-coated tablets containing 5 mg desloratadine, an antihistamine, to be administered orally. CLARINEX Tablets also contain the following excipients: dibasic calcium phosphate dihydrate USP, m...
Active IngredientDesloratadine
Dosage FormTablet, orally disintegrating; Tablet; Syrup; Solution
Routeoral; Oral
Strength2.5mg; 5mg; 0.5mg/ml
Market StatusPrescription
CompanyMerck Sharp Dohme; Schering

2 of 4  
Drug NameDesloratadine
PubMed HealthDesloratadine (By mouth)
Drug ClassesRespiratory Agent
Drug LabelDesloratadine tablets are blue, round, film-coated tablets debossed with logo L5 on one side containing 5 mg desloratadine, an antihistamine, to be administered orally. Desloratadine tablets also contain the following excipients: carnauba wax,...
Active IngredientDesloratadine
Dosage FormTablet, orally disintegrating; Tablet
Routeoral; Oral
Strength2.5mg; 5mg
Market StatusTentative Approval; Prescription
CompanyPerrigo R And D; Mylan Pharms; Glenmark Generics; Belcher Pharms; Lupin Pharms; Sun Pharm Inds; Reddys; Zydus Pharms Usa; Dr Reddys Labs; Sandoz; Orchid Hlthcare

3 of 4  
Drug NameClarinex
PubMed HealthDesloratadine (By mouth)
Drug ClassesRespiratory Agent
Drug LabelCLARINEX (desloratadine) Tablets are light blue, round, film-coated tablets containing 5 mg desloratadine, an antihistamine, to be administered orally. CLARINEX Tablets also contain the following excipients: dibasic calcium phosphate dihydrate USP, m...
Active IngredientDesloratadine
Dosage FormTablet, orally disintegrating; Tablet; Syrup; Solution
Routeoral; Oral
Strength2.5mg; 5mg; 0.5mg/ml
Market StatusPrescription
CompanyMerck Sharp Dohme; Schering

4 of 4  
Drug NameDesloratadine
PubMed HealthDesloratadine (By mouth)
Drug ClassesRespiratory Agent
Drug LabelDesloratadine tablets are blue, round, film-coated tablets debossed with logo L5 on one side containing 5 mg desloratadine, an antihistamine, to be administered orally. Desloratadine tablets also contain the following excipients: carnauba wax,...
Active IngredientDesloratadine
Dosage FormTablet, orally disintegrating; Tablet
Routeoral; Oral
Strength2.5mg; 5mg
Market StatusTentative Approval; Prescription
CompanyPerrigo R And D; Mylan Pharms; Glenmark Generics; Belcher Pharms; Lupin Pharms; Sun Pharm Inds; Reddys; Zydus Pharms Usa; Dr Reddys Labs; Sandoz; Orchid Hlthcare

4.2 Drug Indication

For the relief of symptoms of seasonal allergic rhinitis, perennial (non-seasonal) allergic rhinitis. Desloratidine is also used for the sympomatic treatment of pruritus and urticaria (hives) associated with chronic idiopathic urticaria.


FDA Label


Azomyr is indicated for the relief of symptoms associated with:

- allergic rhinitis (see section 5. 1)

- urticaria (see section 5. 1)


Aerius is indicated for the relief of symptoms associated with:

- allergic rhinitis;

- urticaria.


Neoclarityn is indicated for the relief of symptoms associated with:

- allergic rhinitis

- urticaria


Treatment of allergic rhinitis and urticaria.


Desloratadine Teva is indicated for the relief of symptoms associated with:

- allergic rhinitis;

- urticaria.


Dasselta is indicated for the relief of symptoms associated with:

- allergic rhinitis;

- urticaria.


Desloratadine ratiopharm is indicated in adults for the relief of symptoms associated with:

- allergic rhinitis

- chronic idiopathic urticaria as initially diagnosed by a physician


Aerius is indicated for the relief of symptoms associated with:

- allergic rhinitis (see section 5. 1)

- urticaria (see section 5. 1)


Opulis is indicated for the relief of symptoms associated with:

- allergic rhinitis (see section 5. 1)

- urticaria (see section 5. 1)


5 Pharmacology and Biochemistry
5.1 Pharmacology

Desloratadine is a long-acting second-generation H1-receptor antagonist which has a selective and peripheral H1-antagonist action. Histamine is a chemical that causes many of the signs that are part of allergic reactions, such as the swelling of tissues. Histamine is released from histamine-storing cells (mast cells) and attaches to other cells that have receptors for histamine. The attachment of the histamine to the receptors causes the cell to be "activated," releasing other chemicals which produce the effects that we associate with allergies. Desloratadine blocks one type of receptor for histamine (the H1 receptor) and thus prevents activation of cells by histamine. Unlike most other antihistamines, Desloratadine does not enter the brain from the blood and, therefore, does not cause drowsiness.


5.2 MeSH Pharmacological Classification

Cholinergic Antagonists

Drugs that bind to but do not activate CHOLINERGIC RECEPTORS, thereby blocking the actions of ACETYLCHOLINE or cholinergic agonists. (See all compounds classified as Cholinergic Antagonists.)


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 Active Moiety
DESLORATADINE
5.3.2 FDA UNII
FVF865388R
5.3.3 Pharmacological Classes
Histamine-1 Receptor Antagonist [EPC]; Histamine H1 Receptor Antagonists [MoA]
5.4 ATC Code

R06AX27


R06AX27


R06AX27


R06AX27


R06AX27


R06AX27


R06AX27


R06AX27


R06AX27


R06AX27

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

R06AX27 - Desloratadine


5.5 Absorption, Distribution and Excretion

Absorption

Desloratadine administered orally for ten days to healthy volunteers as a 5 mg tablet once daily resulted in a mean Tmax of approximately 3 hours, a mean steady-state Cmax of 4 ng/ml, and a mean steady-state AUC of 56.9 ng\*hr/ml. A similar profile was observed using 10 ml of an oral solution containing 5 mg of desloratadine. Food was found not to affect desloratadine absorption.


Route of Elimination

Approximately 87% of a 14C-desloratadine dose was equally recovered in urine and feces as metabolic products.


5.6 Metabolism/Metabolites

Desloratadine is metabolized to the active metabolite 3-hydroxydesloratadine, which is subsequently glucuronidated.


Desloratadine is a known human metabolite of Rupatadine and loratadine.

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


5.7 Biological Half-Life

Desloratadine has a mean plasma elimination half-life of approximately 27 hours.


5.8 Mechanism of Action

Like other H1-blockers, Desloratadine competes with free histamine for binding at H1-receptors in the GI tract, uterus, large blood vessels, and bronchial smooth muscle. This blocks the action of endogenous histamine, which subsequently leads to temporary relief of the negative symptoms (eg. nasal congestion, watery eyes) brought on by histamine.


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02-Jan-2021
27-Aug-2024
KGS
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DOSAGE - TABLET;ORAL - 5MG

USFDA APPLICATION NUMBER - 21165

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DOSAGE - SOLUTION;ORAL - 0.5MG/ML **Federal R...DOSAGE - SOLUTION;ORAL - 0.5MG/ML **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

USFDA APPLICATION NUMBER - 21300

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DOSAGE - TABLET, EXTENDED RELEASE;ORAL - 2.5M...DOSAGE - TABLET, EXTENDED RELEASE;ORAL - 2.5MG;120MG

USFDA APPLICATION NUMBER - 21313

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