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Chemistry

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Also known as: 665-66-7, 1-adamantanamine hydrochloride, Amantadine hcl, Symmetrel, 1-aminoadamantane hydrochloride, Adamantan-1-amine hydrochloride
Molecular Formula
C10H18ClN
Molecular Weight
187.71  g/mol
InChI Key
WOLHOYHSEKDWQH-UHFFFAOYSA-N
FDA UNII
M6Q1EO9TD0

Amantadine Hydrochloride
An antiviral that is used in the prophylactic or symptomatic treatment of influenza A. It is also used as an antiparkinsonian agent, to treat extrapyramidal reactions, and for postherpetic neuralgia. The mechanisms of its effects in movement disorders are not well understood but probably reflect an increase in synthesis and release of dopamine, with perhaps some inhibition of dopamine uptake.
1 2D Structure

Amantadine Hydrochloride

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
adamantan-1-amine;hydrochloride
2.1.2 InChI
InChI=1S/C10H17N.ClH/c11-10-4-7-1-8(5-10)3-9(2-7)6-10;/h7-9H,1-6,11H2;1H
2.1.3 InChI Key
WOLHOYHSEKDWQH-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C1C2CC3CC1CC(C2)(C3)N.Cl
2.2 Other Identifiers
2.2.1 UNII
M6Q1EO9TD0
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 1 Aminoadamantane

2. 1-aminoadamantane

3. Adamantylamine

4. Adekin

5. Al, Amantadin

6. Aman

7. Amanta

8. Amanta Hci Azu

9. Amanta-hci-azu

10. Amantadin Al

11. Amantadin Azu

12. Amantadin Neuraxpharm

13. Amantadin Ratiopharm

14. Amantadin Stada

15. Amantadin-neuraxpharm

16. Amantadin-ratiopharm

17. Amantadina Juventus

18. Amantadina Llorente

19. Amantadine

20. Amantadinneuraxpharm

21. Amantadinratiopharm

22. Amantahciazu

23. Amixx

24. Azu, Amantadin

25. Cerebramed

26. Endantadine

27. Gen Amantadine

28. Gen-amantadine

29. Genamantadine

30. Hydrochloride, Amantadine

31. Infecto Flu

32. Infecto-flu

33. Infectoflu

34. Infex

35. Juventus, Amantadina

36. Llorente, Amantadina

37. Mantadix

38. Midantan

39. Pms Amantadine

40. Pms-amantadine

41. Pmsamantadine

42. Stada, Amantadin

43. Symadine

44. Symmetrel

45. Tregor

46. Viregyt

47. Wiregyt

2.3.2 Depositor-Supplied Synonyms

1. 665-66-7

2. 1-adamantanamine Hydrochloride

3. Amantadine Hcl

4. Symmetrel

5. 1-aminoadamantane Hydrochloride

6. Adamantan-1-amine Hydrochloride

7. 1-adamantylamine Hydrochloride

8. Adamantanamine Hydrochloride

9. Amazolon

10. Midantan

11. Midantane

12. Mydantane

13. Virofral

14. Symadine

15. Influenol

16. Mantadix

17. Trivaline

18. Amantan

19. Virasol

20. Viregyt

21. Virosol

22. Amantadine (hydrochloride)

23. 1-adamantanamine, Hydrochloride

24. Adamantylamine Hydrochloride

25. Aminoadamantane Hydrochloride

26. Adamantine Hydrochloride

27. Exp-105-1

28. 1-adamantanamine Hcl

29. Exp 105-1

30. Nsc 83653

31. Osmolex

32. Mfcd00074723

33. Nsc-83653

34. Adamantan-1-amine;hydrochloride

35. Mls000028731

36. Gp 38026

37. Tricyclo[3.3.1.13,7]decan-1-amine, Hydrochloride

38. M6q1eo9td0

39. Ads-5102

40. Amantadine Hydrochloride (symmetrel)

41. Tricyclo(3.3.1.1(sup 3,7))decan-1-amine, Hydrochloride

42. Smr000059204

43. 665-66-7 (hcl)

44. Tricyclo(3.3.1.13,7)decan-1-amine, Hydrochloride

45. Adamantan-1-aminium Chloride

46. Chebi:2619

47. 1-adamantanamine Hydrochloride;1-adamantylamine Hydrochloride;1-aminoadamantane Hydrochloride

48. 1-adamantanaminehydrochloride

49. 1-aminoadamantene Hydrochloride

50. Nsc83653

51. Einecs 211-560-2

52. Unii-m6q1eo9td0

53. Cerebramed

54. Adamine

55. Hofcomant

56. Lysovir

57. Mantadan

58. Mantadine

59. Nurelin

60. Adamin

61. Ai3-52211

62. Sr-01000075353

63. Symmetrel (tn)

64. Osmolex Er (tn)

65. Gocovri (tn)

66. Amantadinehydrochloride

67. Amantadine Hydrochloride [usan:usp:jan]

68. Opera_id_671

69. Adamantamine Hydrochloride

70. Ec 211-560-2

71. Adamantyl Amine Hydrochloride

72. 1-adamantanamin Hydrochlorid

73. C10h17n.hcl

74. Chembl1569

75. Schembl40713

76. Adamantan-1-aminehydrochloride

77. Mls002153257

78. Mls003899199

79. Spectrum1500110

80. Hy-b0402a

81. 1-aminoada- Mantane Hydrochloride

82. Amy3568

83. Dtxsid50874031

84. N04bb01

85. Hms1920a19

86. Pharmakon1600-01500110

87. Ads-5101

88. Bcp11857

89. Str01017

90. Tox21_500004

91. A3a501

92. Amantadine Hydrochloride [mi]

93. Ccg-38899

94. Nsc755860

95. S2451

96. Tricyclo[3.3.1.13, Hydrochloride

97. Amantadine Hydrochloride (jp17/usp)

98. Amantadine Hydrochloride [jan]

99. Akos015900347

100. Akos015951188

101. Ac-8689

102. Amantadine Hydrochloride [usan]

103. Lp00004

104. Nc00489

105. Nsc-755860

106. Amantadine Hydrochloride [mart.]

107. Amantadine Hydrochloride [vandf]

108. 1-adamantylammonium;1-adamantanamine Hcl

109. Amantadine Hydrochloride [usp-rs]

110. Amantadine Hydrochloride [who-dd]

111. Ncgc00093531-01

112. Ncgc00093531-02

113. Ncgc00093531-03

114. Ncgc00093531-04

115. Ncgc00260689-01

116. Ba166177

117. Smr001370746

118. A0588

119. Eu-0100004

120. Ft-0622248

121. Sw219892-1

122. (3r,5s,7s)-adamantan-1-amine Hydrochloride

123. Amantadine Hydrochloride [orange Book]

124. A 1260

125. Amantadine Hydrochloride [ep Monograph]

126. Amantadine Hydrochloride [usp Monograph]

127. C07939

128. D00777

129. F15409

130. Wln: L66 B6 A B- C 1b Itj Bz &gh

131. A835493

132. Amantadine Hydrochlorid 100 Microg/ml In Methanol

133. Amantadine Hydrochloride 1000 Microg/ml In Methanol

134. J-650095

135. J-650235

136. Q-200621

137. Sr-01000075353-1

138. Tricyclo[3.3.1.1 3,7]decan-1-amine Hydrochloride

139. Tricyclo[3.3.1.13,7]decan-1-amine Hydrochloride

140. Q27105739

141. F3111-1111

142. Tricyclo(3.3.1.13,7)decan-1-amine, Hydrochloride (1:1)

143. Amantadine Hydrochloride, European Pharmacopoeia (ep) Reference Standard

144. Amantadine Hydrochloride, Pharmaceutical Secondary Standard; Certified Reference Material

145. Amantadine Hydrochloride, United States Pharmacopeia (usp) Reference Standard

146. 1-aminoadamantane Hydrochloride; 1-adamantanamine Hydrochloride; 1-adamantylamine Hydrochloride

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 187.71 g/mol
Molecular Formula C10H18ClN
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count1
Rotatable Bond Count0
Exact Mass187.1127773 g/mol
Monoisotopic Mass187.1127773 g/mol
Topological Polar Surface Area26 Ų
Heavy Atom Count12
Formal Charge0
Complexity144
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count2
4 Drug and Medication Information
4.1 Drug Information
1 of 2  
Drug NameAmantadine hydrochloride
Drug LabelAmantadine hydrochloride, USP is designated generically as amantadine hydrochloride and chemically as 1-adamantanamine hydrochloride.Amantadine hydrochloride is a stable white or nearly white crystalline powder, freely soluble in water and soluble in...
Active IngredientAmantadine hydrochloride
Dosage FormTablet; Syrup; Capsule
RouteOral
Strength100mg; 50mg/5ml
Market StatusPrescription
CompanyWockhardt; Silarx; Hi Tech Pharma; Carolina Medcl; Pharm Assoc; Vintage; Usl Pharma; Banner Pharmacaps; Sandoz; Mikart

2 of 2  
Drug NameAmantadine hydrochloride
Drug LabelAmantadine hydrochloride, USP is designated generically as amantadine hydrochloride and chemically as 1-adamantanamine hydrochloride.Amantadine hydrochloride is a stable white or nearly white crystalline powder, freely soluble in water and soluble in...
Active IngredientAmantadine hydrochloride
Dosage FormTablet; Syrup; Capsule
RouteOral
Strength100mg; 50mg/5ml
Market StatusPrescription
CompanyWockhardt; Silarx; Hi Tech Pharma; Carolina Medcl; Pharm Assoc; Vintage; Usl Pharma; Banner Pharmacaps; Sandoz; Mikart

4.2 Drug Indication

Treatment of Parkinson's disease and parkinsonism


5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Antiparkinson Agents

Agents used in the treatment of Parkinson's disease. The most commonly used drugs act on the dopaminergic system in the striatum and basal ganglia or are centrally acting muscarinic antagonists. (See all compounds classified as Antiparkinson Agents.)


Antiviral Agents

Agents used in the prophylaxis or therapy of VIRUS DISEASES. Some of the ways they may act include preventing viral replication by inhibiting viral DNA polymerase; binding to specific cell-surface receptors and inhibiting viral penetration or uncoating; inhibiting viral protein synthesis; or blocking late stages of virus assembly. (See all compounds classified as Antiviral Agents.)


Analgesics, Non-Narcotic

A subclass of analgesic agents that typically do not bind to OPIOID RECEPTORS and are not addictive. Many non-narcotic analgesics are offered as NONPRESCRIPTION DRUGS. (See all compounds classified as Analgesics, Non-Narcotic.)


Dopamine Agents

Any drugs that are used for their effects on dopamine receptors, on the life cycle of dopamine, or on the survival of dopaminergic neurons. (See all compounds classified as Dopamine Agents.)


5.2 FDA Pharmacological Classification
5.2.1 Pharmacological Classes
M2 Protein Inhibitors [MoA]; Influenza A M2 Protein Inhibitor [EPC]