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Fomepizole
Also known as: 4-methylpyrazole, 4-methyl-1h-pyrazole, 7554-65-6, Antizol, 1h-pyrazole, 4-methyl-, 4-methylpyrazol
Molecular Formula
C4H6N2
Molecular Weight
82.10  g/mol
InChI Key
RIKMMFOAQPJVMX-UHFFFAOYSA-N
FDA UNII
83LCM6L2BY

A pyrazole and competitive inhibitor of ALCOHOL DEHYDROGENASE that is used for the treatment of poisoning by ETHYLENE GLYCOL or METHANOL.
Fomepizole is an Antidote.
1 2D Structure

Fomepizole

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
4-methyl-1H-pyrazole
2.1.2 InChI
InChI=1S/C4H6N2/c1-4-2-5-6-3-4/h2-3H,1H3,(H,5,6)
2.1.3 InChI Key
RIKMMFOAQPJVMX-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CC1=CNN=C1
2.2 Other Identifiers
2.2.1 UNII
83LCM6L2BY
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 4 Methylpyrazole

2. 4 Methylpyrazole Monohydrochloride

3. 4-methylpyrazole

4. 4-methylpyrazole Monohydrochloride

5. Antizol

2.3.2 Depositor-Supplied Synonyms

1. 4-methylpyrazole

2. 4-methyl-1h-pyrazole

3. 7554-65-6

4. Antizol

5. 1h-pyrazole, 4-methyl-

6. 4-methylpyrazol

7. Fomepizol

8. Fomepizolum

9. Fomepizol [inn-spanish]

10. Fomepizolum [inn-latin]

11. Antizol-vet

12. 4-mp

13. 4-methyl Pyrazole

14. Pyrazole, 4-methyl-

15. Chebi:5141

16. Mfcd00005245

17. Nsc-760365

18. 83lcm6l2by

19. Fomepizole [usan:inn]

20. Antizol (tn)

21. Einecs 231-445-0

22. Unii-83lcm6l2by

23. Brn 0105204

24. Fomepizole [usan:inn:ban]

25. 4-methyl-pyrazole

26. Fomepizole, 99%

27. Fomepizole (antizol)

28. 4-methyl-1h_pyrazole

29. Fomepizole [mi]

30. Fomepizole [inn]

31. Fomepizole [jan]

32. Fomepizole [usan]

33. Lopac-m-1387

34. M0774

35. Fomepizole [vandf]

36. Ec 231-445-0

37. Fomepizole [mart.]

38. Chembl1308

39. Fomepizole [who-dd]

40. Lopac0_000723

41. 5-23-05-00031 (beilstein Handbook Reference)

42. Mls001335923

43. Fomepizole (jan/usan/inn)

44. Fomepizole [green Book]

45. Dtxsid3040649

46. Fomepizole [orange Book]

47. Gtpl11705

48. Hms3713h14

49. Hms3868m13

50. Pharmakon1600-01506159

51. Zinc897288

52. Act05848

53. Act08853

54. Albb-016317

55. Hy-b0876

56. Bdbm50226186

57. Cl3422

58. Nsc760365

59. S1717

60. Stk256626

61. Akos000265586

62. Ab00390

63. Ac-4833

64. Ccg-204808

65. Db01213

66. Nsc 760365

67. Sdccgsbi-0050701.p003

68. Ncgc00015646-01

69. Ncgc00015646-02

70. Ncgc00015646-03

71. Ncgc00015646-04

72. Ncgc00015646-10

73. Ncgc00162231-01

74. 615557-09-0

75. Smr000059088

76. Sy006499

77. 4-methyl-1h-pyrazole;4-methylpyrazole

78. Sbi-0050701.p002

79. Db-022514

80. Db-094915

81. A9615

82. Am20100737

83. Bb 0257933

84. Ft-0626518

85. En300-50246

86. C07837

87. D00707

88. Ab00918526_06

89. Ab00918526_07

90. 554m656

91. A855125

92. Q416410

93. Q-101886

94. Z969563038

95. 4pz

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 82.10 g/mol
Molecular Formula C4H6N2
XLogP31.4
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count1
Rotatable Bond Count0
Exact Mass82.053098200 g/mol
Monoisotopic Mass82.053098200 g/mol
Topological Polar Surface Area28.7 Ų
Heavy Atom Count6
Formal Charge0
Complexity44.8
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 4  
Drug NameAntizol
PubMed HealthFomepizole (Injection)
Drug ClassesToxicology-Antidote Agent
Drug LabelAntizol (fomepizole) Injection is a competitive inhibitor of alcohol dehydrogenase.The chemical name of fomepizole is 4-methylpyrazole. It has the molecular formula C4H6N2 and a molecular weight of 82.1. The structural formula is:It is a clear to y...
Active IngredientFomepizole
Dosage FormInjectable
RouteInjection
Strength1.5gm/1.5ml (1gm/ml)
Market StatusPrescription
CompanyPaladin Labs

2 of 4  
Drug NameFomepizole
Drug LabelFomepizole Injection is a competitive inhibitor of alcohol dehydrogenase. The chemical name of fomepizole is 4-methylpyrazole. It has the molecular formula C4H6N2 and a molecular weight of 82.1. The structural formula is:It is a clear to yellow liqui...
Active IngredientFomepizole
Dosage FormInjectable
RouteInjection
Strength1.5gm/1.5ml (1gm/ml)
Market StatusPrescription
CompanyNavinta; Mylan Institutional; Luitpold

3 of 4  
Drug NameAntizol
PubMed HealthFomepizole (Injection)
Drug ClassesToxicology-Antidote Agent
Drug LabelAntizol (fomepizole) Injection is a competitive inhibitor of alcohol dehydrogenase.The chemical name of fomepizole is 4-methylpyrazole. It has the molecular formula C4H6N2 and a molecular weight of 82.1. The structural formula is:It is a clear to y...
Active IngredientFomepizole
Dosage FormInjectable
RouteInjection
Strength1.5gm/1.5ml (1gm/ml)
Market StatusPrescription
CompanyPaladin Labs

4 of 4  
Drug NameFomepizole
Drug LabelFomepizole Injection is a competitive inhibitor of alcohol dehydrogenase. The chemical name of fomepizole is 4-methylpyrazole. It has the molecular formula C4H6N2 and a molecular weight of 82.1. The structural formula is:It is a clear to yellow liqui...
Active IngredientFomepizole
Dosage FormInjectable
RouteInjection
Strength1.5gm/1.5ml (1gm/ml)
Market StatusPrescription
CompanyNavinta; Mylan Institutional; Luitpold

4.2 Drug Indication

Antizol is indicated as an antidote for ethylene glycol (such as antifreeze) or methanol poisoning, or for use in suspected ethylene glycol or methanol ingestion, either alone or in combination with hemodialysis


5 Pharmacology and Biochemistry
5.1 Pharmacology

Fomepizole is a competitive inhibitor of alcohol dehydrogenase, the enzyme that catalyzes the initial steps in the metabolism of ethylene glycol and methanol to their toxic metabolites. Ethylene glycol is first metabolized to glycoaldehyde which then undergoes further oxidation to glycolate, glyoxylate, and oxalate. Glycolate and oxalate are primarily responsible for metabolic acidosis and renal damage seen in ethylene glycol toxicity. {01}{03} Methanol is first metabolized to formaldehyde and then undergoes subsequent oxidation via formaldehyde dehydrogenase to become formic acid. It is formic acid that is primarily responsible for the metabolic acidosis and visual disturbances that are associated with methanol poisoning.


5.2 MeSH Pharmacological Classification

Antidotes

Agents counteracting or neutralizing the action of POISONS. (See all compounds classified as Antidotes.)


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
FOMEPIZOLE
5.3.2 FDA UNII
83LCM6L2BY
5.3.3 Pharmacological Classes
Antidote [EPC]
5.4 ATC Code

V - Various

V03 - All other therapeutic products

V03A - All other therapeutic products

V03AB - Antidotes

V03AB34 - Fomepizole


5.5 Absorption, Distribution and Excretion

Absorption

Rapid and complete


Route of Elimination

In healthy volunteers, only 1-3.5% of the administered dose of Antizol (7-20 mg/kg oral and IV) was excreted unchanged in the urine, indicating that metabolism is the major route of elimination. In humans, the primary metabolite of Antizol is 4-carboxypyrazole (approximately 80-85% of administered dose), which is excreted in the urine. The metabolites of Antizol are excreted renally.


Volume of Distribution

0.6 to 1.02 L/kg


5.6 Metabolism/Metabolites

Primarily hepatic. the primary metabolite is 4-carboxypyrazole (approximately 80 to 85% of an administered dose). Minor metabolites include 4-hydroxymethylpyrazole and the N -glucuronide conjugates of 4-carboxypyrazole and 4-hydroxymethylpyrazole.


5.7 Biological Half-Life

The plasma half-life of Antizol varies with dose, even in patients with normal renal function, and has not been calculated.


5.8 Mechanism of Action

Antizol (fomepizole) is a competitive inhibitor of alcohol dehydrogenase. Alcohol dehydrogenase catalyzes the oxidation of ethanol to acetaldehyde. Alcohol dehydrogenase also catalyzes the initial steps in the metabolism of ethylene glycol and methanol to their toxic metabolites.


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