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Chemistry

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Also known as: N-hydroxyacetamide, 546-88-3, Lithostat, Methylhydroxamic acid, Acetylhydroxamic acid, Acetic acid, oxime
Molecular Formula
C2H5NO2
Molecular Weight
75.07  g/mol
InChI Key
RRUDCFGSUDOHDG-UHFFFAOYSA-N
FDA UNII
4RZ82L2GY5

Acetohydroxamic Acid
acetohydroxamic acid is a natural product found in Chlamydomonas reinhardtii and Arabidopsis thaliana with data available.
Acetohydroxamic acid is an Urease Inhibitor. The mechanism of action of acetohydroxamic acid is as an Urease Inhibitor.
1 2D Structure

Acetohydroxamic Acid

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
N-hydroxyacetamide
2.1.2 InChI
InChI=1S/C2H5NO2/c1-2(4)3-5/h5H,1H3,(H,3,4)
2.1.3 InChI Key
RRUDCFGSUDOHDG-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CC(=O)NO
2.2 Other Identifiers
2.2.1 UNII
4RZ82L2GY5
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Lithostat

2. N-hydroxyacetamide

3. N-hydroxyacetamidine

4. Uronefrex

2.3.2 Depositor-Supplied Synonyms

1. N-hydroxyacetamide

2. 546-88-3

3. Lithostat

4. Methylhydroxamic Acid

5. Acetylhydroxamic Acid

6. Acetic Acid, Oxime

7. N-acetylhydroxylamine

8. Acetohydroximic Acid

9. Acetamide, N-hydroxy-

10. Acethydroxamsaeure

11. N-acetyl Hydroxyacetamide

12. Cetohyroxamic Acid

13. Acetohydroxamate

14. Acethydroxamsaure

15. Acethydroxamic Acid

16. Aha

17. Hydroxylamine, N-acetyl-

18. Acido Acetohidroxamico

19. Acide Acetohydroxamique

20. Acidum Acetohydroxamicum

21. N-hydroxy-acetamide

22. Nsc 176136

23. Mfcd00009994

24. Nsc-176136

25. 4rz82l2gy5

26. Acetamide, N-hydroxy- (9ci)

27. Chebi:27777

28. Ncgc00094576-01

29. Dsstox_cid_2546

30. Wln: Qmv1

31. Acetohydroxamicacid

32. Acetyl Hydroxyamino

33. Dsstox_rid_76622

34. Dsstox_gsid_22546

35. Acethydroxamsaeure [german]

36. Oxime

37. Acide Acetohydroxamique [french]

38. Acido Acetohidroxamico [spanish]

39. Acidum Acetohydroxamicum [latin]

40. Lithostat (tn)

41. Cas-546-88-3

42. Ccris 1730

43. Hsdb 3585

44. N-hydroxyacetimidic Acid

45. N-hydroxyethanimidic Acid

46. Einecs 208-913-8

47. Unii-4rz82l2gy5

48. Ai3-62232

49. Acetohydroxamsaure

50. Acetohydroxamic Acid (usp/inn)

51. Acetic Acid

52. Oxime

53. N-oxylatoacetamide

54. Acethydroximic Acid

55. Acetohyroxamic Acid

56. Acetyl Hydroxyamine

57. Prestwick_38

58. Acetohydroxamic-acid

59. N-oxidanylethanamide

60. Acetohydroxarnic Acid

61. Acetohydroxamic Acid [usan:usp:inn]

62. Methyl Hydroximic Acid

63. Spectrum_000020

64. Spectrum2_000109

65. Spectrum3_000285

66. Spectrum4_000138

67. Spectrum5_000812

68. Ch3c(o)nhoh

69. Chembl734

70. Acetohydroxamic Acid, 98%

71. Bspbio_001790

72. Kbiogr_000556

73. Kbioss_000360

74. Mls001076662

75. Divk1c_000821

76. Spectrum1500103

77. Spbio_000098

78. Dtxsid7022546

79. Chebi:49029

80. Hms502j03

81. Kbio1_000821

82. Kbio2_000360

83. Kbio2_002928

84. Kbio2_005496

85. Kbio3_001290

86. Acetohydroxamic Acid [mi]

87. Nsc5073

88. Ninds_000821

89. Acetohydroxamic Acid (aha)

90. Acetohydroxamic Acid [inn]

91. Hms1920a07

92. Hms2091g07

93. Hms2231m17

94. Pharmakon1600-01500103

95. Acetohydroxamic Acid [hsdb]

96. Acetohydroxamic Acid [usan]

97. Act05768

98. Hy-b1235

99. Nsc-5073

100. Str08084

101. Zinc4658603

102. Acetohydroxamic Acid [vandf]

103. Tox21_111301

104. Acetohydroxamic Acid [mart.]

105. Bdbm50099857

106. Ccg-38927

107. Geo-00010

108. Nsc176136

109. Nsc755855

110. S4602

111. Acetohydroxamic Acid [usp-rs]

112. Acetohydroxamic Acid [who-dd]

113. Akos000172340

114. Tox21_111301_1

115. Ab01014

116. Cs-4881

117. Db00551

118. Nsc-755855

119. Idi1_000821

120. Ncgc00094576-02

121. Ncgc00094576-03

122. Ncgc00094576-05

123. Acetohydroxamic Acid [orange Book]

124. Bp-13320

125. Smr000499570

126. Sbi-0051270.p003

127. Acetohydroxamic Acid [usp Monograph]

128. Db-052632

129. A0051

130. Am20100343

131. Ft-0621796

132. En300-36948

133. 46a883

134. C06808

135. D00220

136. Ab00051907_07

137. A830321

138. Q481822

139. Sr-01000763642

140. Sr-01000763642-2

141. W-105609

142. Acetohydroxamic Acid, United States Pharmacopeia (usp) Reference Standard

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 75.07 g/mol
Molecular Formula C2H5NO2
XLogP3-1.6
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count2
Rotatable Bond Count0
Exact Mass75.032028402 g/mol
Monoisotopic Mass75.032028402 g/mol
Topological Polar Surface Area49.3 Ų
Heavy Atom Count5
Formal Charge0
Complexity42.9
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 NameLithostat
PubMed HealthAcetohydroxamic Acid (By mouth)
Drug ClassesUrinary Stone Agent
Drug LabelAcetohydroxamic acid (AHA) is a stable, synthetic compound derived from hydroxylamine and ethyl acetate. Its molecular structure is similar to urea:AHA is weakly acidic, highly soluble in water, and chelates metals - notably iron. The molecular weigh...
Active IngredientAcetohydroxamic acid
Dosage FormTablet
RouteOral
Strength250mg
Market StatusPrescription
CompanyMission Pharma

2 of 2  
Drug NameLithostat
PubMed HealthAcetohydroxamic Acid (By mouth)
Drug ClassesUrinary Stone Agent
Drug LabelAcetohydroxamic acid (AHA) is a stable, synthetic compound derived from hydroxylamine and ethyl acetate. Its molecular structure is similar to urea:AHA is weakly acidic, highly soluble in water, and chelates metals - notably iron. The molecular weigh...
Active IngredientAcetohydroxamic acid
Dosage FormTablet
RouteOral
Strength250mg
Market StatusPrescription
CompanyMission Pharma

4.2 Therapeutic Uses

Enzyme Inhibitors

National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)


Acetohydroxamic acid is indicated in the prophylaxis of struvite calculi formation that is promoted by urease-producing bacteria such as Proteus. Its use may enhance effectiveness of urinary antibacterials, especially following surgical removal of existing stones. Use of acetohydroxamic acid also improves the possibility of reducing the frequency and rate of new stone formation. /Included in US product labeling/

USP Convention. USPDI - Drug Information for the Health Care Professional. 17th ed. Volume I. Rockville, MD: Convention, Inc., 1997. (Plus Updates)., p. 14


Acetohydroxamic acid is indicated as an adjunct in the treatment of chronic, urea-splitting urinary tract infections caused by urease-producing bacteria. Its inhibition of urease activity decreases the urinary ammonia and alkalinity produced from the enzyme hydrolysis of urea. /Included in US product labeling/

USP Convention. USPDI - Drug Information for the Health Care Professional. 17th ed. Volume I. Rockville, MD: Convention, Inc., 1997. (Plus Updates)., p. 14


4.3 Drug Warning

Acetohydroxamic acid is not indicated for dissolution of existing calculi, replacement of indicated surgical treatment, urinary tract infections controllable by culture-specific oral antibacterials, or urinary tract infections caused by nonurease producing organisms.

USP Convention. USPDI - Drug Information for the Health Care Professional. 17th ed. Volume I. Rockville, MD: Convention, Inc., 1997. (Plus Updates)., p. 14


Use of acetohydroxamic acid is contraindicated during pregnancy since studies in animals have shown it to cause leg deformities at doses of 750 mg/kg of body weight and above. At doses of 1500 mg/kg, exencephaly and encephalocele occurred. Also, cardiac, coccygeal, and abdominal-wall anomalies developed in pups of beagle dogs given 25 mg/kg a day during pregnancy.

USP Convention. USPDI - Drug Information for the Health Care Professional. 17th ed. Volume I. Rockville, MD: Convention, Inc., 1997. (Plus Updates)., p. 14


It is not known if acetohydroxamic acid is distributed into breast milk. Although problems in humans have not been documented, its use is not recommended in breast-feeding mothers because of the potential for serious adverse effects in the nursing infant.

USP Convention. USPDI - Drug Information for the Health Care Professional. 17th ed. Volume I. Rockville, MD: Convention, Inc., 1997. (Plus Updates)., p. 14


Headache, appearing during the first 48 hours of treatment, reportedly occurs in approximately 30% of patients receiving acetohydroxamic acid; however, several clinicians reported that mild, transient headache occurred in 70-75% of patients during initiation of therapy. Headache is generally mild, responsive to oral salicylate analgesics, and usually disappears spontaneously. Headache has not been associated with vertigo, tinnitus, or visual or auditory disturbances. Malaise occurs in about 20-25% of patients receiving the drug.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 97. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 1997 (Plus Supplements)., p. 1980


For more Drug Warnings (Complete) data for ACETOHYDROXAMIC ACID (12 total), please visit the HSDB record page.


4.4 Drug Indication

Used, in addition to antibiotics or medical procedures, to treat chronic urea-splitting urinary infections.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Acetohydroxamic Acid, a synthetic drug derived from hydroxylamine and ethyl acetate, is similar in structure to urea. In the urine, it acts as an antagonist of the bacterial enzyme urease. Acetohydroxamic Acid has no direct antimicrobial action and does not acidify urine directly.


5.2 MeSH Pharmacological Classification

Enzyme Inhibitors

Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. (See all compounds classified as Enzyme Inhibitors.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
ACETOHYDROXAMIC ACID
5.3.2 FDA UNII
4RZ82L2GY5
5.3.3 Pharmacological Classes
Urease Inhibitors [MoA]; Urease Inhibitor [EPC]
5.4 ATC Code

G - Genito urinary system and sex hormones

G04 - Urologicals

G04B - Urologicals

G04BX - Other urologicals

G04BX03 - Acetohydroxamic acid


5.5 Absorption, Distribution and Excretion

Absorption

Well absorbed from the GI tract following oral administration.


Well absorbed from gastrointestinal tract.

USP Convention. USPDI - Drug Information for the Health Care Professional. 17th ed. Volume I. Rockville, MD: Convention, Inc., 1997. (Plus Updates)., p. 14


Well distributed throughout body fluids.

USP Convention. USPDI - Drug Information for the Health Care Professional. 17th ed. Volume I. Rockville, MD: Convention, Inc., 1997. (Plus Updates)., p. 14


Elimination: Renal- Unchanged, 36 to 65%; as acetamide, 9 to 14%. Respiratory - As carbon dioxide, 20 to 40%.

USP Convention. USPDI - Drug Information for the Health Care Professional. 17th ed. Volume I. Rockville, MD: Convention, Inc., 1997. (Plus Updates)., p. 14


In rodents, about 55% of an intraperitoneal dose is excreted in urine as unchanged drug, 15% as acetamide, and 10% as acetate within 24 hours; approximately 7% of the dose is excreted by the lungs as carbon dioxide and less than 1% is excreted in feces within 24 hours.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 97. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 1997 (Plus Supplements)., p. 1979


In mice, highest concentrations of the drug occur in the liver and kidney, while the lowest concentrations occur in the brain.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 97. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 1997 (Plus Supplements)., p. 1978


5.6 Metabolism/Metabolites

35-65% of oral dose excreted unchanged in urine (which provides the drug's therapeutic effect).


...is metabolized to acetamide.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 97. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 1997 (Plus Supplements)., p. 1979


5.7 Biological Half-Life

5-10 hours in patients with normal renal function


...increases with increasing dose and reportedly ranges from about 3.5-10 hours in patients with normal renal function.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 97. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 1997 (Plus Supplements)., p. 1979


5.8 Mechanism of Action

Acetohydroxamic Acid reversibly inhibits the bacterial enzyme urease. This inhibits the hydrolysis of urea and production of ammonia in urine infected with urea-splitting organisms, leading to a decrease in pH and ammonia levels. As antimicrobial agents are more effective in such conditions, the effectiveness of these agents is amplified, resulting in a higher cure rate.


Inhibits the hydrolysis of urea and production of ammonia in urine infected with urea-splitting bacteria, by reversible inhibition of the bacterial enzyme urease, and by the chelation of nickel, an essential component of urease enzymes. Such enzyme inhibition results in reduction of both urine alkalinity and ammonia concentration. The effectiveness of antibacterial medication is then enhanced and the formation of urinary calculi reduced.

USP Convention. USPDI - Drug Information for the Health Care Professional. 17th ed. Volume I. Rockville, MD: Convention, Inc., 1997. (Plus Updates)., p. 14


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26-Apr-2021
10-Jul-2024
KGS
overview