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NCGC00024443-02

NCGC00024443-02

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Also known as: 2609-46-3, Amipramidin, Midamor, Guanamprazine, Amipramizid, Amipramizide

Molecular Formula

C₆H₈ClN₇O

Molecular Weight

229.63 g/mol

InChI Key

XSDQTOBWRPYKKA-UHFFFAOYSA-N

FDA UNII

7DZO8EB0Z3

A pyrazine compound inhibiting SODIUM reabsorption through SODIUM CHANNELS in renal EPITHELIAL CELLS. This inhibition creates a negative potential in the luminal membranes of principal cells, located in the distal convoluted tubule and collecting duct. Negative potential reduces secretion of potassium and hydrogen ions. Amiloride is used in conjunction with DIURETICS to spare POTASSIUM loss. (From Gilman et al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 9th ed, p705)

Amiloride is a Potassium-sparing Diuretic. The physiologic effect of amiloride is by means of Decreased Renal K+ Excretion, and Increased Diuresis.

1 2D Structure

NCGC00024443-02

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

3,5-diamino-6-chloro-N-(diaminomethylidene)pyrazine-2-carboxamide

2.1.2 InChI

InChI=1S/C6H8ClN7O/c7-2-4(9)13-3(8)1(12-2)5(15)14-6(10)11/h(H4,8,9,13)(H4,10,11,14,15)

2.1.3 InChI Key

XSDQTOBWRPYKKA-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C1(=C(N=C(C(=N1)Cl)N)N)C(=O)N=C(N)N

2.2 Other Identifiers

2.2.1 UNII

7DZO8EB0Z3

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Amidal

2. Amiduret Trom

3. Amiloberag

4. Amiloride Hydrochloride

5. Amiloride Hydrochloride, Anhydrous

6. Anhydrous Amiloride Hydrochloride

7. Hydrochloride, Amiloride

8. Hydrochloride, Anhydrous Amiloride

9. Kaluril

10. Midamor

11. Midoride

12. Modamide

13. Trom, Amiduret

2.3.2 Depositor-Supplied Synonyms

1. 2609-46-3

2. Amipramidin

3. Midamor

4. Guanamprazine

5. Amipramizid

6. Amipramizide

7. Guanamprazin

8. Amilorida

9. 3,5-diamino-n-carbamimidoyl-6-chloropyrazine-2-carboxamide

10. Amiloridum

11. Amyloride

12. Amiloridum [inn-latin]

13. Amilorida [inn-spanish]

14. Amiclaran

15. N-amidino-3,5-diamino-6-chloropyrazinecarboxamide

16. N-amidino-3,5-diamino-6-chlorpyrazincarboxamid

17. 3,5-diamino-6-chloro-n-(diaminomethylidene)pyrazine-2-carboxamide

18. Amiloride (inn)

19. Pyrazinecarboxamide, 3,5-diamino-n-(aminoiminomethyl)-6-chloro-

20. 3,5-diamino-n-(aminoiminomethyl)-6-chloropyrazinecarboxamide

21. Mk-870

22. Chembl945

23. 7dzo8eb0z3

24. Chebi:2639

25. 137053-86-2

26. Ncgc00015089-08

27. Amiloride [inn]

28. Amiloride [inn:ban]

29. Amipramidine

30. Dsstox_cid_23853

31. Dsstox_rid_80077

32. Dsstox_gsid_43853

33. Amiclaran (tn)

34. Cas-2609-46-3

35. Ccris 6545

36. Einecs 220-024-7

37. Unii-7dzo8eb0z3

38. Amiloridehcl

39. Amikal (hydrochloride Dihydrate)

40. Midamor (hydrochloride Dihydrate)

41. Mk-870 (hydrochloride Dihydrate)

42. Amipramidin, Midamor

43. N-amidino-3,5-diamino-6-chloro-2-pyrazinecarboxamide

44. Spectrum_000034

45. Tocris-0890

46. 1f5l

47. Amiloride [mi]

48. Prestwick0_000007

49. Prestwick1_000007

50. Prestwick2_000007

51. Prestwick3_000007

52. Spectrum2_000118

53. Spectrum3_000293

54. Spectrum4_000132

55. Spectrum5_000776

56. Amiloride [vandf]

57. Lopac-a-7410

58. Amiloride [who-dd]

59. Lopac0_000111

60. Schembl27562

61. Bspbio_000013

62. Bspbio_001572

63. Bspbio_001826

64. Kbiogr_000292

65. Kbiogr_000544

66. Kbioss_000292

67. Kbioss_000394

68. Mls001060798

69. Bidd:gt0466

70. Divk1c_000182

71. Spbio_000136

72. Spbio_001934

73. Bpbio1_000015

74. Gtpl2421

75. Dtxsid9043853

76. Bcbcmap01_000101

77. Bdbm16173

78. Kbio1_000182

79. Kbio2_000292

80. Kbio2_000394

81. Kbio2_002860

82. Kbio2_002962

83. Kbio2_005428

84. Kbio2_005530

85. Kbio3_000583

86. Kbio3_000584

87. Kbio3_001326

88. Ninds_000182

89. Bio1_000359

90. Bio1_000848

91. Bio1_001337

92. Bio2_000292

93. Bio2_000772

94. Hms1791o14

95. Hms1989o14

96. Hms2089h05

97. Hms2213e05

98. Hms3355k04

99. Act05635

100. Act05652

101. Bcp16815

102. Hy-b0285

103. Zinc4340269

104. Tox21_110080

105. 3,5-diamino-n-[amino(imino)methyl]-6-chloropyrazine-2-carboxamide

106. Bbl028157

107. Stl373007

108. Akos015961348

109. Tox21_110080_1

110. Ccg-204206

111. Db00594

112. Sb74937

113. Sdccgsbi-0050099.p005

114. Idi1_000182

115. Idi1_034042

116. Ncgc00015089-01

117. Ncgc00015089-02

118. Ncgc00015089-03

119. Ncgc00015089-04

120. Ncgc00015089-05

121. Ncgc00015089-06

122. Ncgc00015089-07

123. Ncgc00015089-09

124. Ncgc00015089-11

125. Ncgc00015089-12

126. Ncgc00015089-13

127. Ncgc00015089-14

128. Ncgc00015089-15

129. Ncgc00015089-16

130. Ncgc00015089-17

131. Ncgc00015089-24

132. Ncgc00024443-02

133. Ncgc00024443-05

134. Ncgc00024443-06

135. Ncgc00024443-07

136. Ncgc00024443-09

137. Ac-13631

138. Ls-13128

139. Smr000486264

140. (3,5-diamino-6-chloropyrazinoyl)guanidine

141. Sbi-0050099.p004

142. N-amidino-3,5-diamino-6-chloropyrazinamide

143. Ab00053415

144. Ft-0703177

145. C06821

146. D07447

147. Ab00053415-24

148. Ab00053415-25

149. Ab00053415_26

150. Ab00053415_27

151. Ab00053415_28

152. 609a463

153. Q419995

154. J-016249

155. Brd-k97181089-003-02-3

156. Brd-k97181089-310-03-0

157. N-amidino 3,5-diamino-6-chloro-2-pyrazinecarboxamide

158. F2173-0531

159. N-(3,5-diamino-6-chloro-pyrazine-2-carbonyl)-guanidine

160. 3,5-diamino-n-carbamimidoyl-6-chloro-pyrazine-2-carboxamide

161. 3,5-diamino-6-chloro-n-(diaminomethylene)pyrazinamide;hydrochloride

2.4 Create Date

2005-03-27

3 Chemical and Physical Properties

Molecular Formula	C₆H₈ClN₇O
Molecular Weight	229.63 g/mol
XLogP3	-0.7
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	1
Exact Mass	229.0478856 g/mol
Monoisotopic Mass	229.0478856 g/mol
Topological Polar Surface Area	159 Å²
Heavy Atom Count	15
Formal Charge	0
Complexity	279
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	1

4 Drug and Medication Information

4.1 Drug Information

1 of 2
Drug Name	Midamor
PubMed Health	Amiloride (By mouth)
Drug Classes	Cardiovascular Agent
Drug Label	Amiloride HCl, an antikaliuretic-diuretic agent, is a pyrazine-carbonyl-guanidine that is unrelated chemically to other known antikaliuretic or diuretic agents. It is the salt of a moderately strong base (pKa 8.7). It is designated chemically as 3,5-...
Active Ingredient	Amiloride hydrochloride
Dosage Form	Tablet
Route	Oral
Strength	5mg
Market Status	Prescription
Company	Paddock

2 of 2
Drug Name	Midamor
PubMed Health	Amiloride (By mouth)
Drug Classes	Cardiovascular Agent
Drug Label	Amiloride HCl, an antikaliuretic-diuretic agent, is a pyrazine-carbonyl-guanidine that is unrelated chemically to other known antikaliuretic or diuretic agents. It is the salt of a moderately strong base (pKa 8.7). It is designated chemically as 3,5-...
Active Ingredient	Amiloride hydrochloride
Dosage Form	Tablet
Route	Oral
Strength	5mg
Market Status	Prescription
Company	Paddock

4.2 Drug Indication

For use as adjunctive treatment with thiazide diuretics or other kaliuretic-diuretic agents in congestive heart failure or hypertension.

FDA Label

5 Pharmacology and Biochemistry

5.1 Pharmacology

Amiloride, an antikaliuretic-diuretic agent, is a pyrazine-carbonyl-guanidine that is unrelated chemically to other known antikaliuretic or diuretic agents. It is an antihypertensive, potassium-sparing diuretic that was first approved for use in 1967 and helps to treat hypertension and congestive heart failure. The drug is often used in conjunction with thiazide or loop diuretics. Due to its potassium-sparing capacities, hyperkalemia (high blood potassium levels) are occasionally observed in patients taking amiloride. The risk is high in concurrent use of ACE inhibitors or spironolactone. Patients are also advised not to use potassium-containing salt replacements.

5.2 MeSH Pharmacological Classification

Acid Sensing Ion Channel Blockers

A subclass of sodium channel blockers that are specific for ACID-SENSING SODIUM CHANNELS. (See all compounds classified as Acid Sensing Ion Channel Blockers.)

Diuretics

Agents that promote the excretion of urine through their effects on kidney function. (See all compounds classified as Diuretics.)

Epithelial Sodium Channel Blockers

A subclass of sodium channel blockers that are specific for EPITHELIAL SODIUM CHANNELS. (See all compounds classified as Epithelial Sodium Channel Blockers.)

5.3 FDA Pharmacological Classification

5.3.1 Active Moiety

AMILORIDE

5.3.2 FDA UNII

7DZO8EB0Z3

5.3.3 Pharmacological Classes

Established Pharmacologic Class [EPC] - Potassium-sparing Diuretic

5.4 ATC Code

C - Cardiovascular system

C03 - Diuretics

C03D - Aldosterone antagonists and other potassium-sparing agents

C03DB - Other potassium-sparing agents

C03DB01 - Amiloride

5.5 Absorption, Distribution and Excretion

Absorption

Readily absorbed following oral administration.

Route of Elimination

Amiloride HCl is not metabolized by the liver but is excreted unchanged by the kidneys. About 50 percent of a 20 mg dose of amiloride HCl is excreted in the urine and 40 percent in the stool within 72 hours.

5.6 Metabolism/Metabolites

Amiloride is not metabolized by the liver but is excreted unchanged by the kidneys.

5.7 Biological Half-Life

Plasma half-life varies from 6 to 9 hours.

5.8 Mechanism of Action

Amiloride works by inhibiting sodium reabsorption in the distal convoluted tubules and collecting ducts in the kidneys by binding to the amiloride-sensitive sodium channels. This promotes the loss of sodium and water from the body, but without depleting potassium. Amiloride exerts its potassium sparing effect through the inhibition of sodium reabsorption at the distal convoluted tubule, cortical collecting tubule and collecting duct; this decreases the net negative potential of the tubular lumen and reduces both potassium and hydrogen secretion and their subsequent excretion. Amiloride is not an aldosterone antagonist and its effects are seen even in the absence of aldosterone.

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