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Clonidine

Synopsis, Chemistry

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TABLET;ORAL - 0.1MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**, TABLET;ORAL - 0.2MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**, TABLET;ORAL - 0.3MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**, TABLET, EXTENDED RELEASE;ORAL - 0.1MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**, TABLET, EXTENDED RELEASE;ORAL - 0.2MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

TABLET;ORAL - 0.1MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**
TABLET;ORAL - 0.2MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**
TABLET;ORAL - 0.3MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**
TABLET, EXTENDED RELEASE;ORAL - 0.1MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**
TABLET, EXTENDED RELEASE;ORAL - 0.2MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

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Also known as: 4205-91-8, Clonidine hcl, 2-(2,6-dichloroanilino)-2-imidazoline hydrochloride, Kapvay, N-(2,6-dichlorophenyl)-4,5-dihydro-1h-imidazol-2-amine hydrochloride, St-155

Molecular Formula

C₉H₁₀Cl₃N₃

Molecular Weight

266.6 g/mol

InChI Key

ZNIFSRGNXRYGHF-UHFFFAOYSA-N

FDA UNII

W76I6XXF06

An imidazoline sympatholytic agent that stimulates ALPHA-2 ADRENERGIC RECEPTORS and central IMIDAZOLINE RECEPTORS. It is commonly used in the management of HYPERTENSION.

1 2D Structure

Clonidine

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

N-(2,6-dichlorophenyl)-4,5-dihydro-1H-imidazol-2-amine;hydrochloride

2.1.2 InChI

InChI=1S/C9H9Cl2N3.ClH/c10-6-2-1-3-7(11)8(6)14-9-12-4-5-13-9;/h1-3H,4-5H2,(H2,12,13,14);1H

2.1.3 InChI Key

ZNIFSRGNXRYGHF-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C1CN=C(N1)NC2=C(C=CC=C2Cl)Cl.Cl

2.2 Other Identifiers

2.2.1 UNII

W76I6XXF06

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Catapres

2. Catapresan

3. Catapressan

4. Chlophazolin

5. Clofelin

6. Clofenil

7. Clonidine

8. Clonidine Dihydrochloride

9. Clonidine Monohydrobromide

10. Clonidine Monohydrochloride

11. Clopheline

12. Dihydrochloride, Clonidine

13. Dixarit

14. Gemiton

15. Hemiton

16. Hydrochloride, Clonidine

17. Isoglaucon

18. Klofelin

19. Klofenil

20. M 5041t

21. M-5041t

22. M5041t

23. Monohydrobromide, Clonidine

24. Monohydrochloride, Clonidine

25. St 155

26. St-155

27. St155

2.3.2 Depositor-Supplied Synonyms

1. 4205-91-8

2. Clonidine Hcl

3. 2-(2,6-dichloroanilino)-2-imidazoline Hydrochloride

4. Kapvay

5. N-(2,6-dichlorophenyl)-4,5-dihydro-1h-imidazol-2-amine Hydrochloride

6. St-155

7. Catapresan

8. Jenloga

9. Clonidine (hydrochloride)

10. Nsc-756699

11. 2-(2,6-dichlorophenylamino)-2-imidazoline Hydrochloride

12. W76i6xxf06

13. Dichloranilino Imidazolin

14. 2-((2,6-dichlorophenyl)imino)imidazolidine Monohydrochloride

15. Benzenamine, 2,6-dichloro-n-2-imidazolidinylidene-, Monohydrochloride

16. Chlophazolin

17. Dispaclonidin

18. Normopresan

19. Atensina

20. Barclyd

21. Capresin

22. Caprysin

23. Catanidin

24. Clofelin

25. Clonilou

26. Clonisin

27. Clonistada

28. Dixarit

29. Edolglau

30. Glausine

31. Haemiton

32. Ipotensium

33. Isoglaucon

34. Katapresan

35. Klophelin

36. Iporel

37. 1h-imidazol-2-amine, N-(2,6-dichlorophenyl)-4,5-dihydro- [cas]

38. Apo-clonidine

39. Clonidil-riker

40. Novo-clonidine

41. Clonid-ophal

42. Nu-clonidine

43. N-(2,6-dichlorophenyl)-4,5-dihydro-1h-imidazol-2-amine Hcl

44. 1h-imidazol-2-amine, N-(2,6-dichlorophenyl)-4,5-dihydro-, Monohydrochloride (9ci)

45. 2-[(2,6-dichlorophenyl)amino-2-imidazoline Hydrochloride

46. Bapresan

47. Clonicel

48. Trialox

49. Clonidine Monohydrochloride

50. Smr000466276

51. 205c918

52. Sr-01000075246

53. Einecs 224-121-5

54. Cas-4205-91-8

55. Mfcd00036705

56. N-(2,6-dichlorophenyl)imidazolidin-2-imine;hydrochloride

57. Unii-w76i6xxf06

58. Clonidine-hcl

59. Sr-01000759380

60. Prestwick_73

61. Catapres (tn)

62. 4,5-dihydro-

63. 2-((2,6-dichlorophenyl)amino)-2-imidazoline Hydrochloride

64. 2-imidazoline, 2-(2,6-dichloroanilino)-, Monohydrochloride

65. 2-(2,6-dichlorophenylamino)-2-imidazolin Hydrochlorid [german]

66. Benzenamine, 2,6-dichloro-n-2-imidazolidinylidene-, Hydrochloride

67. Clonidine Hydrochloride [usan:usp:ban:jan]

68. 1h-imidazol-2-amine, N-(2,6-dichlorophenyl)-4,5-dihydro-, Monohydrochloride

69. Clonidinehydrochloride

70. N-(2,6-dichlorophenyl)-

71. Chembl1705

72. Clonidine Hydrochloride,(s)

73. Dsstox_cid_24670

74. Dsstox_rid_80388

75. Dsstox_gsid_44670

76. Schembl40751

77. Mls000758256

78. Mls001424222

79. Clonidine Hydrochloride, Solid

80. 2-(2,6-dichlorophenylamino)-2-imidazolin Hydrochlorid

81. Chebi:3758

82. Dtxsid8044670

83. Hy-b0409a

84. Clonidine Hydrochloride (catapres)

85. Hms1568b18

86. Hms3414h03

87. Hms3678h03

88. Pharmakon1600-01500198

89. Bcp14375

90. Clonidine Hydrochloride [mi]

91. Tox21_301552

92. Tox21_500268

93. Bdbm50020341

94. Ccg-40087

95. Clonidine Hydrochloride (jp17/usp)

96. Clonidine Hydrochloride [jan]

97. N-(2,6-dichlorophenyl)-4,5-dihydro-1h-imidazol-2-amine;hydrochloride

98. Nsc756699

99. S2458

100. Clonidine Hydrochloride [usan]

101. Akos005267207

102. Akos024458609

103. Akos028114993

104. Ccg-101051

105. Ccg-212540

106. Ccg-229466

107. Clonidine Hydrochloride [mart.]

108. Clonidine Hydrochloride [vandf]

109. Ks-1253

110. Lp00268

111. Nc00301

112. Nsc 756699

113. Clonidine Hydrochloride [usp-rs]

114. Clonidine Hydrochloride [who-dd]

115. Ncgc00093726-01

116. Ncgc00093726-02

117. Ncgc00180902-01

118. Ncgc00256172-01

119. Ncgc00260953-01

120. Ac-10306

121. Ac-29742

122. Clonidine Hydrochloride, >=98.0% (tlc)

123. Clonidine Hydrochloride [ep Impurity]

124. Clonidine Hydrochloride [orange Book]

125. D1353

126. Eu-0100268

127. Ft-0601096

128. Ft-0665123

129. Sw197681-3

130. Clonidine Hydrochloride [ep Monograph]

131. C 7897

132. Clonidine Hydrochloride [usp Monograph]

133. D00604

134. D81843

135. Clorpres Component Clonidine Hydrochloride

136. A825736

137. Clonidine Hydrochloride 100 Microg/ml In Methanol

138. Combipres Component Clonidine Hydrochloride

139. Clonidine Hydrochloride Component Of Clorpres

140. Q-200880

141. Sr-01000075246-1

142. Sr-01000075246-3

143. Sr-01000759380-5

144. Clonidine Hydrochloride (catapres) [largely Precursor]

145. Clonidine Hydrochloride Component Of Combipres

146. Q27292429

147. 2-[(2,6-dichlorophenyl)imino]imidazolidine Hydrochloride

148. Clonidine Hydrochloride 1.0 Mg/ml In Methanol (as Free Base)

149. Clonidine Hydrochloride, British Pharmacopoeia (bp) Reference Standard

150. Clonidine Hydrochloride, European Pharmacopoeia (ep) Reference Standard

151. Clonidine Hydrochloride, United States Pharmacopeia (usp) Reference Standard

152. 1h-imidazol-2-amine, N-(2,6-dichlorophenyl)-4,5-dihydro-, Hydrochloride (1:1)

153. N-[2,6-bis(chloranyl)phenyl]-4,5-dihydro-1h-imidazol-2-amine Hydrochloride

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₉H₁₀Cl₃N₃
Molecular Weight	266.6 g/mol
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	1
Rotatable Bond Count	2
Exact Mass	264.994030 g/mol
Monoisotopic Mass	264.994030 g/mol
Topological Polar Surface Area	36.4 Å²
Heavy Atom Count	15
Formal Charge	0
Complexity	222
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

4 Drug and Medication Information

4.1 Drug Information

1 of 4
Drug Name	Clonidine hydrochloride
PubMed Health	Clonidine
Drug Classes	Analgesic, Anesthetic Adjunct, Antihypertensive, Antimigraine, Cardiovascular Agent, Central Nervous System Agent, Diagnostic Agent, Pheochromocytoma
Drug Label	Clonidine hydrochloride, USP is a centrally acting alpha-agonist hypotensive agent available as tablets for oral administration in three dosage strengths: 0.1 mg, 0.2 mg, and 0.3 mg. The 0.1 mg tablet is equivalent to 0.087 mg of the free base.The fo...
Active Ingredient	Clonidine hydrochloride
Dosage Form	Tablet, extended release; Injectable; Tablet
Route	Injection; Oral
Strength	0.2mg; 1mg/10ml (0.1mg/ml); 0.3mg; 5mg/10ml (0.5mg/ml); 0.1mg
Market Status	Prescription
Company	Exela Pharma Scs; Anchen Pharms; Actavis Elizabeth; Fresenius Kabi Usa; Unichem; Mutual Pharm; Vintage; Alembic Pharms; Hikma Farmaceutica; Luitpold; Sun Pharm Inds; Zydus Pharms Usa; Carlsbad; Mylan; Impax Labs; Dava Pharms

2 of 4
Drug Name	Kapvay
Drug Label	KAPVAY (clonidine hydrochloride) extended-release is a centrally acting alpha2-adrenergic agonist available as 0.1 mg or 0.2 mg extended-release tablets for oral administration. Each 0.1 mg and 0.2 mg tablet is equivalent to 0.087 mg and 0.174 mg, re...
Active Ingredient	Clonidine hydrochloride
Dosage Form	Tablet, extended release
Route	Oral
Strength	0.1mg; 0.2mg
Market Status	Prescription
Company	Concordia Pharms

3 of 4
Drug Name	Clonidine hydrochloride
PubMed Health	Clonidine
Drug Classes	Analgesic, Anesthetic Adjunct, Antihypertensive, Antimigraine, Cardiovascular Agent, Central Nervous System Agent, Diagnostic Agent, Pheochromocytoma
Drug Label	Clonidine hydrochloride, USP is a centrally acting alpha-agonist hypotensive agent available as tablets for oral administration in three dosage strengths: 0.1 mg, 0.2 mg, and 0.3 mg. The 0.1 mg tablet is equivalent to 0.087 mg of the free base.The fo...
Active Ingredient	Clonidine hydrochloride
Dosage Form	Tablet, extended release; Injectable; Tablet
Route	Injection; Oral
Strength	0.2mg; 1mg/10ml (0.1mg/ml); 0.3mg; 5mg/10ml (0.5mg/ml); 0.1mg
Market Status	Prescription
Company	Exela Pharma Scs; Anchen Pharms; Actavis Elizabeth; Fresenius Kabi Usa; Unichem; Mutual Pharm; Vintage; Alembic Pharms; Hikma Farmaceutica; Luitpold; Sun Pharm Inds; Zydus Pharms Usa; Carlsbad; Mylan; Impax Labs; Dava Pharms

4 of 4
Drug Name	Kapvay
Drug Label	KAPVAY (clonidine hydrochloride) extended-release is a centrally acting alpha2-adrenergic agonist available as 0.1 mg or 0.2 mg extended-release tablets for oral administration. Each 0.1 mg and 0.2 mg tablet is equivalent to 0.087 mg and 0.174 mg, re...
Active Ingredient	Clonidine hydrochloride
Dosage Form	Tablet, extended release
Route	Oral
Strength	0.1mg; 0.2mg
Market Status	Prescription
Company	Concordia Pharms

4.2 Drug Indication

Sedation

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Adrenergic alpha-2 Receptor Agonists

Compounds that bind to and activate ADRENERGIC ALPHA-2 RECEPTORS. (See all compounds classified as Adrenergic alpha-2 Receptor Agonists.)

Analgesics

Compounds capable of relieving pain without the loss of CONSCIOUSNESS. (See all compounds classified as Analgesics.)

Antihypertensive Agents

Drugs used in the treatment of acute or chronic vascular HYPERTENSION regardless of pharmacological mechanism. Among the antihypertensive agents are DIURETICS; (especially DIURETICS, THIAZIDE); ADRENERGIC BETA-ANTAGONISTS; ADRENERGIC ALPHA-ANTAGONISTS; ANGIOTENSIN-CONVERTING ENZYME INHIBITORS; CALCIUM CHANNEL BLOCKERS; GANGLIONIC BLOCKERS; and VASODILATOR AGENTS. (See all compounds classified as Antihypertensive Agents.)

Sympatholytics

Drugs that inhibit the actions of the sympathetic nervous system by any mechanism. The most common of these are the ADRENERGIC ANTAGONISTS and drugs that deplete norepinephrine or reduce the release of transmitters from adrenergic postganglionic terminals (see ADRENERGIC AGENTS). Drugs that act in the central nervous system to reduce sympathetic activity (e.g., centrally acting alpha-2 adrenergic agonists, see ADRENERGIC ALPHA-AGONISTS) are included here. (See all compounds classified as Sympatholytics.)

5.2 FDA Pharmacological Classification

5.2.1 Pharmacological Classes

Central alpha-2 Adrenergic Agonist [EPC]; Adrenergic alpha2-Agonists [MoA]