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    Amiloride Hydrochloride

    ACTIVE PHARMA INGREDIENTS

    INTERMEDIATES

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    2D Structure
    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

    2D Structure

    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

    2.3.3 Other Synonyms

    1. Amilorid Hydrochlorid-2-wasser

    2. Amiloride Hydrochloride Dihydrate

    2.4 Create Date
    2005-03-27
    3 Chemical and Physical Properties
    Molecular Weight 229.63 g/mol
    Molecular Formula C6H8ClN7O
    XLogP3-0.7
    Hydrogen Bond Donor Count4
    Hydrogen Bond Acceptor Count5
    Rotatable Bond Count1
    Exact Mass229.0478856 g/mol
    Monoisotopic Mass229.0478856 g/mol
    Topological Polar Surface Area159 Ų
    Heavy Atom Count15
    Formal Charge0
    Complexity279
    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 2  
    Drug NameMidamor
    PubMed HealthAmiloride (By mouth)
    Drug ClassesCardiovascular Agent
    Drug LabelAmiloride 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 IngredientAmiloride hydrochloride
    Dosage FormTablet
    RouteOral
    Strength5mg
    Market StatusPrescription
    CompanyPaddock

    2 of 2  
    Drug NameMidamor
    PubMed HealthAmiloride (By mouth)
    Drug ClassesCardiovascular Agent
    Drug LabelAmiloride 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 IngredientAmiloride hydrochloride
    Dosage FormTablet
    RouteOral
    Strength5mg
    Market StatusPrescription
    CompanyPaddock

    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.