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Chemistry

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Also known as: Methanoic acid, 64-18-6, Formylic acid, Aminic acid, Bilorin, Hydrogen carboxylic acid
Molecular Formula
CH2O2
Molecular Weight
46.025  g/mol
InChI Key
BDAGIHXWWSANSR-UHFFFAOYSA-N
FDA UNII
0YIW783RG1

Formic Acid
Formic Acid is a reagent comprised of the organic chemical formic acid that cleaves proteins into peptides at the C- or N-terminal side of an aspartate residue.
1 2D Structure

Formic Acid

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
formic acid
2.1.2 InChI
InChI=1S/CH2O2/c2-1-3/h1H,(H,2,3)
2.1.3 InChI Key
BDAGIHXWWSANSR-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C(=O)O
2.2 Other Identifiers
2.2.1 UNII
0YIW783RG1
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Aluminum Formate

2. Ammonium Formate

3. Ammonium Tetraformate

4. Calcium Formate

5. Chromic Formate

6. Cobalt(ii) Formate Dihydrate

7. Cobaltous Formate

8. Cupric Formate

9. Formate

10. Formic Acid, 14c-labeled

11. Formic Acid, Aluminum Salt

12. Formic Acid, Ammonium (2:1) Salt

13. Formic Acid, Ammonium (4:1) Salt

14. Formic Acid, Ammonium Salt

15. Formic Acid, Cadmium Salt

16. Formic Acid, Calcium Salt

17. Formic Acid, Cesium Salt

18. Formic Acid, Cobalt (+2) Salt

19. Formic Acid, Copper (+2) Salt

20. Formic Acid, Copper Salt

21. Formic Acid, Copper, Ammonium Salt

22. Formic Acid, Copper, Nickel Salt

23. Formic Acid, Cromium (+3) Salt

24. Formic Acid, Cromium (+3), Sodium (4:1:1) Salt

25. Formic Acid, Lead (+2) Salt

26. Formic Acid, Lead Salt

27. Formic Acid, Lithium Salt

28. Formic Acid, Magnesium Salt

29. Formic Acid, Nickel (+2) Salt

30. Formic Acid, Nickel Salt

31. Formic Acid, Potassium Salt

32. Formic Acid, Rubidium Salt

33. Formic Acid, Sodium Salt

34. Formic Acid, Sodium Salt, 13c-labeled

35. Formic Acid, Sodium Salt, 14c-labeled

36. Formic Acid, Strontium Salt

37. Formic Acid, Thallium (+1) Salt

38. Formic Acid, Zinc Salt

39. Lead Formate

40. Lithium Formate

41. Magnesium Formate

42. Methanoic Acid

43. Nickel Formate

44. Nickel Formate Dihydrate

45. Potassium Formate

46. Sodium Formate

47. Strontium Formate

48. Zinc Formate

2.3.2 Depositor-Supplied Synonyms

1. Methanoic Acid

2. 64-18-6

3. Formylic Acid

4. Aminic Acid

5. Bilorin

6. Hydrogen Carboxylic Acid

7. Formisoton

8. Myrmicyl

9. Formira

10. Collo-bueglatt

11. Collo-didax

12. Acide Formique

13. Add-f

14. Ameisensaeure

15. C1 Acid

16. Rcra Waste Number U123

17. Spirit Of Formic Acid

18. Formic Acid (natural)

19. Mierenzuur [dutch]

20. Mierenzuur

21. Formicum Acidum

22. Kwas Metaniowy

23. Acido Formico

24. Ameisensaeure [german]

25. Kyselina Mravenci

26. Acide Formique [french]

27. Acido Formico [italian]

28. Fema No. 2487

29. Kwas Metaniowy [polish]

30. Kyselina Mravenci [czech]

31. Hcooh

32. Ameisensaure

33. Ccris 6039

34. Sybest

35. Epa Pesticide Chemical Code 214900

36. Ai3-24237

37. Rcra Waste No. U123

38. Un1779

39. Formic Acid, Dimer

40. Methanoic Acid Monomer

41. Hco2h

42. Mfcd00003297

43. Wonderbond Hardener M 600l

44. 0yiw783rg1

45. Chebi:30751

46. Aminate

47. Formylate

48. Methanoate

49. Formic Acid [un1779] [corrosive]

50. Formic Acid, 88%

51. 0.1% Fa In Water

52. Hydrogen Carboxylate

53. 0.1% Fa In Water,

54. 0.1% Fa In Acn

55. 0.1% Fa In Acn,

56. 0.1% Formic Acid In Water (v/v)

57. Cal-ex™ Ii Fixative/decalcifier

58. 14523-98-9

59. 0.1% Formic Acid In Acetonitrile (v/v)

60. Hsdb 1646

61. Einecs 200-579-1

62. Unii-0yiw783rg1

63. Amasil

64. Forrnic Acid

65. Methoic Acid

66. Icosatrienoic Acids

67. Eicosatrienoic Acids

68. Fatty Acid 20:3

69. Fatty Acid 26:0

70. Formic Acid, Natural

71. H-cooh

72. Formic Acid, Acs Grade

73. Formic Acid [mi]

74. Bmse000203

75. Formic Acid [fcc]

76. Ec 200-579-1

77. Formic Acid, 95-97%

78. Formic Acid [fhfi]

79. Formic Acid [hsdb]

80. Formic Acid [inci]

81. Formic Acid, Lc/ms Grade

82. Formic Acid [vandf]

83. Formic Acid [mart.]

84. Formic Acid, P.a., 85%

85. Formic Acid [usp-rs]

86. Formic Acid [who-dd]

87. Formic Acid (fragrance Grade)

88. Formic Acid, Ar, >=90%

89. Formic Acid, Ar, >=98%

90. Formic Acid, Lr, >=85%

91. Formic Acid, Lr, >=98%

92. Formicum Acidum [hpus]

93. Chembl116736

94. Formic Acid, Purum, >=85%

95. Formic Acid (industrial Grade)

96. Dtxsid2024115

97. Chebi:36036

98. Chebi:191874

99. Formic Acid [ep Monograph]

100. Amy11055

101. Bcp23013

102. Formic Acid Ampoules (lcms Grade)

103. Formic Acid, >=95%, Fcc, Fg

104. Formic Acid, Technical Grade, 85%

105. Formic Acid 88% Reagent Grade Acs

106. Formic Acid, Acs Reagent, >=96%

107. Stl264243

108. Formic Acid, Reagent Grade, >=95%

109. Varromed Component Formic Acid

110. Akos000269044

111. Formic Acid Solution, 1.0m In Water

112. Formic Acid, Acs Reagent, 88-91%

113. Water With 0.1% Formic Acid (v/v)

114. Ccg-266004

115. Db01942

116. Un 1779

117. Formic Acid, Acs Reagent, >=96.0%

118. Formic Acid Component Of Varromed

119. Ncgc00248718-01

120. Bp-21436

121. E236

122. Formic Acid [ema Epar Veterinary]

123. Db-029851

124. C20:3

125. F0513

126. F0654

127. Formic Acid 1000 Microg/ml In Acetonitrile

128. Formic Acid, Jis Special Grade, >=98.0%

129. Formic Acid, Vetec(tm) Reagent Grade, 95%

130. Ft-0626533

131. Ft-0626535

132. Ft-0626537

133. Ft-0668804

134. C00058

135. Formic Acid, Saj First Grade, 88.0-89.5%

136. Formic Acid Solution, Bioultra, 1.0 M In H2o

137. A834666

138. Q161233

139. Formic Acid, P.a., Acs Reagent, 98.0-100.0%

140. J-521387

141. Q27110013

142. F1908-0082

143. Formate Standard For Ic, 1.000 G/l In H2o, Analytical Standard

144. Formic Acid, Puriss. P.a., Acs Reagent, Reag. Ph. Eur., >=98%

145. Formic Acid, United States Pharmacopeia (usp) Reference Standard

146. Formic Acid, Puriss., Meets Analytical Specifications Of Dac, Fcc, 98.0-100%

147. 82069-14-5

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 46.025 g/mol
Molecular Formula CH2O2
XLogP3-0.2
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count2
Rotatable Bond Count0
Exact Mass46.005479302 g/mol
Monoisotopic Mass46.005479302 g/mol
Topological Polar Surface Area37.3 Ų
Heavy Atom Count3
Formal Charge0
Complexity10.3
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 Therapeutic Uses

Medication (vet): appears to prevent candida growth in partridges exposed to candida after receiving treated feed (20 mL of 6% solution/100 g feed for 1 week and then 2% soln). Similarly, a 15% solution can be used to control an outbreak of candida albicans.

Rossoff, I.S. Handbook of Veterinary Drugs. New York: Springer Publishing Company, 1974., p. 228


THERAPEUTIC CATEGORY: Caustic

O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 2006., p. 727


5 Pharmacology and Biochemistry
5.1 Absorption, Distribution and Excretion

Absorption

Formic acid is readily metabolized and eliminated by the body.


Formic acid is absorbed from the gastrointestinal tract, via the lungs and the intact skin. The absorbed substance is degraded to carbon dioxide (CO2) and water and is partially excreted unchanged in the urine.

EPA/Office of Pollution Prevention and Toxics; High Production Volume (HPV) Challenge Program's Robust Summaries and Test Plans. Formates (December 2001). Available from, as of July 12, 2005: https://www.epa.gov/hpv/pubs/hpvrstp.htm


The dose-dependent elimination of formate was investigated in the rat using both in vitro and in vivo systems. The in situ perfused liver was used to define the kinetics of hepatic metabolism and obtain initial in vitro estimates of the hepatic metabolism parameters. Formate was eliminated from the perfused rat liver following the Michaelis-Menten kinetics. Estimates of the Michaelis-Menten parameters obtained from the perfused liver studies were used in a two-compartment pharmacokinetic model of the dose-dependent elimination of formate in vivo. A good fit of the model to the observed in vivo data was obtained. Initial estimates of the Michaelis-Menten parameters, Vmax and Km, obtained from the perfused liver model, were within 40% of the final fitted values of these parameters in the in vivo model.

EPA/Office of Pollution Prevention and Toxics; High Production Volume (HPV) Challenge Program's Robust Summaries and Test Plans. Formates (December 2001). Available from, as of July 12, 2005: https://www.epa.gov/hpv/pubs/hpvrstp.htm


Some formic acid may be excreted unchanged, the amt depending on the species, dose, and route of admin.

Clayton, G. D. and F. E. Clayton (eds.). Patty's Industrial Hygiene and Toxicology: Volume 2A, 2B, 2C: Toxicology. 3rd ed. New York: John Wiley Sons, 1981-1982., p. 4908


During hemodialysis in a methanol poisoned patient, formate elimination followed first order kinetics with a plasma half-life of 165 min. The mean dialyzer (1.6 at 59 mL) clearance of formate was 148 mL/min at a blood flow of 215 mL/min. Distribution volume was 0.5 L/kg. Formate is more effectively removed by hemodialysis than methanol. /Formate/

PMID:6660049 Jacobsen D et al; Acta Med Scand 214 (5): 409-12 (1983)


For more Absorption, Distribution and Excretion (Complete) data for FORMIC ACID (7 total), please visit the HSDB record page.


5.2 Metabolism/Metabolites

Formate is a normal constituent of intermediary metabolism ... /of formic acid/. Formate is metabolized in the rat primarily via the one carbon pool, but in some circumstances the catalase-peroxidative pathway may serve as an alternative route of oxidation. Oxidation occurs in a variety of organs and tissues, including liver, lung, and erythrocytes, the end products being carbon dioxide and water.

Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. V5 p.697


Enzyme pathways involved in detoxification of hydrogen peroxide, formaldehyde, and formic acid, which are produced as a consequence of oxidative demethylation by the cytochrome P-450 system, were examined in isolated hepatocytes from phenobarbital pretreated rats. The formaldehyde produced during oxidative demethylation in isolated hepatocytes is rapidly oxidized to formic acid. Depletion of cellular reduced glutathione by pretreatment of rats with diethylmaleate decreases the rate of formic acid production, and therefore, it appears that formaldehyde produced by oxidative demethylation is oxidized by formaldehyde dehydrogenase, an enzyme which requires but does not consume reduced glutathione. Because of the rapid nonenzymatic reaction of formaldehyde with reduced glutathione, this enzyme system may be viewed as essential to prevent the loss of reduced glutathione due to S-hydroxymethylglutathione formation. Reduced glutathione concentration in isolated hepatocytes decreased rapidly following addition of substrates undergoing oxidative demethylation. Addition of other cytochrome P-450 substrates which do not undergo demethylation did not result in such a dramatic oxidation of reduced glutathione. Formic acid, produced during oxidative demethylation acts as a substrate for the peroxidatic mode of catalase, but also binds to catalase as an anionic ligand. This binding decreases the catalase concentration detectable by cyanide titration and therefore appears to inhibit the catalytic reaction mode.

PMID:567217 Jones DP et al; J Biol Chem 253 (17): 6031-7 (1978)


The major part of the absorbed formic acid is metabolized in the liver, but partially also in the intestinal mucosa, lungs, kidneys and spleen. Formic acid is oxidized in relation to folate and according to a catalase-peroxidative mechanism. Formic acid is metabolized into CO2 considerably more slowly in primates than in rats. The species sensitivity to methanol intoxication (metabolic acidosis caused by formic acid) is possibly dependent on the tetrahydrofolate concentration.

EPA/Office of Pollution Prevention and Toxics; High Production Volume (HPV) Challenge Program's Robust Summaries and Test Plans. Formates (December 2001). Available from, as of July 12, 2005: https://www.epa.gov/hpv/pubs/hpvrstp.htm


Formic acid was excreted in the urine of rabbits during inhalation of methyl alcohol ... .

Clayton, G. D. and F. E. Clayton (eds.). Patty's Industrial Hygiene and Toxicology: Volume 2A, 2B, 2C: Toxicology. 3rd ed. New York: John Wiley Sons, 1981-1982., p. 4535


For more Metabolism/Metabolites (Complete) data for FORMIC ACID (8 total), please visit the HSDB record page.


5.3 Biological Half-Life

... Mean half-life of serum formate was 2.6 hr, when methanol metabolism was assumed blocked by fomepizole and no folinic acid was given. ... /formate/

PMID:16035197 Hovda KE et al; Clin Toxicol (Phila). 43 (4): 221-7 (2005)


The biologic half-life /of formic acid/ is between 15 minutes and 1 hour.

EPA/Office of Pollution Prevention and Toxics; High Production Volume (HPV) Challenge Program's Robust Summaries and Test Plans. Formates (December 2001). Available from, as of July 12, 2005: https://www.epa.gov/hpv/pubs/hpvrstp.htm


5.4 Mechanism of Action

Formic acid is an inhibitor of the mitochondrial cytochrome oxidase causing histotoxic hypoxia. The most significant acid load results from the hypoxic metabolism. Urinary acidification is affected by formic acid.

Sheftel, V.O.; Indirect Food Additives and Polymers. Migration and Toxicology. Lewis Publishers, Boca Raton, FL. 2000., p. 914


Formic acid is a mitochondrial toxin, and exerts effects primarily in areas (such as the retina or basal ganglia) that poorly tolerate an interruption in the energy supplied by oxidative phosphorylation.

Goldfrank, L.R. (ed). Goldfrank's Toxicologic Emergencies. 7th Edition McGraw-Hill New York, New York 2002., p. 200


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API | Excipient name

Formic Acid

Synonyms

Methanoic acid, 64-18-6, Formylic acid, Aminic acid, Bilorin, Hydrogen carboxylic acid

Cas Number

64-18-6

Unique Ingredient Identifier (UNII)

0YIW783RG1

About Formic Acid

Formic Acid is a reagent comprised of the organic chemical formic acid that cleaves proteins into peptides at the C- or N-terminal side of an aspartate residue.

Amasil Manufacturers

A Amasil manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Amasil, including repackagers and relabelers. The FDA regulates Amasil manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Amasil API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

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A Amasil DMF (Drug Master File) is a document detailing the whole manufacturing process of Amasil active pharmaceutical ingredient (API) in detail. Different forms of Amasil DMFs exist exist since differing nations have different regulations, such as Amasil USDMF, ASMF (EDMF), JDMF, CDMF, etc.

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A Amasil CoA (Certificate of Analysis) is a formal document that attests to Amasil's compliance with Amasil specifications and serves as a tool for batch-level quality control.

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