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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2022-07-12 15:36:35 UTC
HMDB IDHMDB0015344
Secondary Accession Numbers
  • HMDB15344
Metabolite Identification
Common NameFomepizole
DescriptionFomepizole, also known as 4-methylpyrazole or antizol, belongs to the class of organic compounds known as pyrazoles. Pyrazoles are compounds containing a pyrazole ring, which is a five-member aromatic ring with two nitrogen atoms (at positions 1 and 2) and three carbon atoms. Fomepizole is a moderately basic compound (based on its pKa). It is a medication used to treat methanol and ethylene glycol poisoning. It is given by injection into a vein. Fomepizole was approved for medical use in the United States in 1997. It is on the World Health Organization's List of Essential Medicines. Fomepizole is a competitive inhibitor of the enzyme alcohol dehydrogenase, found in the liver. This enzyme plays a key role in the metabolism of ethylene glycol, and of methanol. By competitively inhibiting alcohol dehydrogenase, in the metabolism of ethylene glycol and methanol, fomepizole slows the production of the toxic metabolites. The slower rate of metabolite production allows the liver to process and excrete the metabolites as they are produced, limiting the accumulation in tissues such as the kidney and eye. As a result, much of the organ damage is avoided.
Structure
Data?1582753286
Synonyms
ValueSource
4-MethylpyrazolChEBI
4-MethylpyrazoleChEBI
AntizolChEBI
FomepizolChEBI
FomepizolumChEBI
4-Methylpyrazole monohydrochlorideHMDB
4 MethylpyrazoleHMDB
4 Methylpyrazole monohydrochlorideHMDB
Chemical FormulaC4H6N2
Average Molecular Weight82.1038
Monoisotopic Molecular Weight82.053098202
IUPAC Name4-methyl-1H-pyrazole
Traditional Namefomepizole
CAS Registry Number7554-65-6
SMILES
CC1=CNN=C1
InChI Identifier
InChI=1S/C4H6N2/c1-4-2-5-6-3-4/h2-3H,1H3,(H,5,6)
InChI KeyRIKMMFOAQPJVMX-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pyrazoles. Pyrazoles are compounds containing a pyrazole ring, which is a five-member aromatic ring with two nitrogen atoms (at positions 1 and 2) and three carbon atoms.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassAzoles
Sub ClassPyrazoles
Direct ParentPyrazoles
Alternative Parents
Substituents
  • Heteroaromatic compound
  • Pyrazole
  • Azacycle
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point25 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility559 g/LNot Available
LogP0.9Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility559 g/LALOGPS
logP0.41ALOGPS
logP0.79ChemAxon
logS0.83ALOGPS
pKa (Strongest Acidic)15.82ChemAxon
pKa (Strongest Basic)2.13ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area28.68 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity24.79 m³·mol⁻¹ChemAxon
Polarizability8.58 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+113.72531661259
DarkChem[M-H]-109.57431661259
DeepCCS[M+H]+118.68130932474
DeepCCS[M-H]-116.60630932474
DeepCCS[M-2H]-152.34130932474
DeepCCS[M+Na]+126.90430932474
AllCCS[M+H]+115.732859911
AllCCS[M+H-H2O]+110.532859911
AllCCS[M+NH4]+120.632859911
AllCCS[M+Na]+122.132859911
AllCCS[M-H]-116.632859911
AllCCS[M+Na-2H]-120.432859911
AllCCS[M+HCOO]-124.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
FomepizoleCC1=CNN=C11817.1Standard polar33892256
FomepizoleCC1=CNN=C1892.6Standard non polar33892256
FomepizoleCC1=CNN=C1979.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Fomepizole,1TMS,isomer #1CC1=CN([Si](C)(C)C)N=C11058.7Semi standard non polar33892256
Fomepizole,1TMS,isomer #1CC1=CN([Si](C)(C)C)N=C11051.1Standard non polar33892256
Fomepizole,1TMS,isomer #1CC1=CN([Si](C)(C)C)N=C11349.3Standard polar33892256
Fomepizole,1TBDMS,isomer #1CC1=CN([Si](C)(C)C(C)(C)C)N=C11285.0Semi standard non polar33892256
Fomepizole,1TBDMS,isomer #1CC1=CN([Si](C)(C)C(C)(C)C)N=C11238.8Standard non polar33892256
Fomepizole,1TBDMS,isomer #1CC1=CN([Si](C)(C)C(C)(C)C)N=C11475.9Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Fomepizole GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-9000000000-b35d3e8671e7a89229422017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Fomepizole GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Fomepizole LC-ESI-QQ , positive-QTOFsplash10-001i-9000000000-a316743b875614673db92017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fomepizole LC-ESI-QQ , positive-QTOFsplash10-001i-9000000000-42791f260f9285d6f7802017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fomepizole LC-ESI-QQ , positive-QTOFsplash10-001i-9000000000-569b1673c9ab233c40132017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fomepizole LC-ESI-QQ , positive-QTOFsplash10-015c-9000000000-5ae86e9abf74bac03fba2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fomepizole LC-ESI-QQ , positive-QTOFsplash10-014l-9000000000-41e338b06d239025c0e72017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fomepizole 10V, Positive-QTOFsplash10-001i-9000000000-1d562baa9f5c93b7e0a82016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fomepizole 20V, Positive-QTOFsplash10-0pb9-9000000000-c2f7f054abd0758694382016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fomepizole 40V, Positive-QTOFsplash10-0udi-9000000000-1a3a3e1f7403f01f7b492016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fomepizole 10V, Negative-QTOFsplash10-001i-9000000000-0397be4ae693384bf8832016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fomepizole 20V, Negative-QTOFsplash10-0udi-9000000000-a9d0bdbc2b563c58af902016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fomepizole 40V, Negative-QTOFsplash10-0ue9-9000000000-e58185108e313fdf109e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fomepizole 10V, Positive-QTOFsplash10-001i-9000000000-e915842469b9abe9d2af2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fomepizole 20V, Positive-QTOFsplash10-052r-9000000000-c6f49a9015cbb0de82862021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fomepizole 40V, Positive-QTOFsplash10-000i-9000000000-966f7a70f99f03945c2d2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fomepizole 10V, Negative-QTOFsplash10-001i-9000000000-5fba3d16c726bdbb206a2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fomepizole 20V, Negative-QTOFsplash10-001i-9000000000-20eaadb94506d03b550d2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fomepizole 40V, Negative-QTOFsplash10-0udi-9000000000-0073bd384ec724d496942021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01213 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01213 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01213
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID3289
KEGG Compound IDC07837
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkFomepizole
METLIN IDNot Available
PubChem Compound3406
PDB ID4PZ
ChEBI ID5141
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in zinc ion binding
Specific function:
Not Available
Gene Name:
ADH1B
Uniprot ID:
P00325
Molecular weight:
39835.17
References
  1. Yin SJ, Liao CS, Chen CM, Fan FT, Lee SC: Genetic polymorphism and activities of human lung alcohol and aldehyde dehydrogenases: implications for ethanol metabolism and cytotoxicity. Biochem Genet. 1992 Apr;30(3-4):203-15. [PubMed:1590750 ]
  2. Eriksson CJ, Fukunaga T, Sarkola T, Chen WJ, Chen CC, Ju JM, Cheng AT, Yamamoto H, Kohlenberg-Muller K, Kimura M, Murayama M, Matsushita S, Kashima H, Higuchi S, Carr L, Viljoen D, Brooke L, Stewart T, Foroud T, Su J, Li TK, Whitfield JB: Functional relevance of human adh polymorphism. Alcohol Clin Exp Res. 2001 May;25(5 Suppl ISBRA):157S-163S. [PubMed:11391066 ]
  3. Kassam JP, Tang BK, Kadar D, Kalow W: In vitro studies of human liver alcohol dehydrogenase variants using a variety of substrates. Drug Metab Dispos. 1989 Sep-Oct;17(5):567-72. [PubMed:2573502 ]
  4. Brent J: Fomepizole for ethylene glycol and methanol poisoning. N Engl J Med. 2009 May 21;360(21):2216-23. doi: 10.1056/NEJMct0806112. [PubMed:19458366 ]
  5. Calello DP, Osterhoudt KC, Henretig FM: New and novel antidotes in pediatrics. Pediatr Emerg Care. 2006 Jul;22(7):523-30. [PubMed:16871118 ]
  6. Betten DP, Vohra RB, Cook MD, Matteucci MJ, Clark RF: Antidote use in the critically ill poisoned patient. J Intensive Care Med. 2006 Sep-Oct;21(5):255-77. [PubMed:16946442 ]
General function:
Involved in zinc ion binding
Specific function:
Not Available
Gene Name:
ADH1A
Uniprot ID:
P07327
Molecular weight:
39858.37
References
  1. Nagata H, Sekizuka E, Morishita T, Tatemichi M, Kurokawa T, Mizuki A, Ishii H: Adenosine A2-receptor mediates ethanol-induced arteriolar dilation in rat stomach. Am J Physiol. 1996 Dec;271(6 Pt 1):G1028-33. [PubMed:8997246 ]
  2. Mukherjee PK, Mohamed S, Chandra J, Kuhn D, Liu S, Antar OS, Munyon R, Mitchell AP, Andes D, Chance MR, Rouabhia M, Ghannoum MA: Alcohol dehydrogenase restricts the ability of the pathogen Candida albicans to form a biofilm on catheter surfaces through an ethanol-based mechanism. Infect Immun. 2006 Jul;74(7):3804-16. [PubMed:16790752 ]
  3. Nussrallah BA, Dam R, Wagner FW: Characterization of Coturnix quail liver alcohol dehydrogenase enzymes. Biochemistry. 1989 Jul 25;28(15):6245-51. [PubMed:2789998 ]
  4. Brent J: Fomepizole for ethylene glycol and methanol poisoning. N Engl J Med. 2009 May 21;360(21):2216-23. doi: 10.1056/NEJMct0806112. [PubMed:19458366 ]
  5. Calello DP, Osterhoudt KC, Henretig FM: New and novel antidotes in pediatrics. Pediatr Emerg Care. 2006 Jul;22(7):523-30. [PubMed:16871118 ]
  6. Betten DP, Vohra RB, Cook MD, Matteucci MJ, Clark RF: Antidote use in the critically ill poisoned patient. J Intensive Care Med. 2006 Sep-Oct;21(5):255-77. [PubMed:16946442 ]
General function:
Involved in zinc ion binding
Specific function:
Not Available
Gene Name:
ADH1C
Uniprot ID:
P00326
Molecular weight:
39867.27
References
  1. Eriksson CJ, Fukunaga T, Sarkola T, Chen WJ, Chen CC, Ju JM, Cheng AT, Yamamoto H, Kohlenberg-Muller K, Kimura M, Murayama M, Matsushita S, Kashima H, Higuchi S, Carr L, Viljoen D, Brooke L, Stewart T, Foroud T, Su J, Li TK, Whitfield JB: Functional relevance of human adh polymorphism. Alcohol Clin Exp Res. 2001 May;25(5 Suppl ISBRA):157S-163S. [PubMed:11391066 ]
  2. Brent J: Fomepizole for ethylene glycol and methanol poisoning. N Engl J Med. 2009 May 21;360(21):2216-23. doi: 10.1056/NEJMct0806112. [PubMed:19458366 ]
  3. Calello DP, Osterhoudt KC, Henretig FM: New and novel antidotes in pediatrics. Pediatr Emerg Care. 2006 Jul;22(7):523-30. [PubMed:16871118 ]
  4. Betten DP, Vohra RB, Cook MD, Matteucci MJ, Clark RF: Antidote use in the critically ill poisoned patient. J Intensive Care Med. 2006 Sep-Oct;21(5):255-77. [PubMed:16946442 ]
General function:
Involved in monooxygenase activity
Specific function:
Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic or carcinogenic forms.
Gene Name:
CYP2E1
Uniprot ID:
P05181
Molecular weight:
56848.42
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase activity
Specific function:
Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Constitutes the major nicotine C-oxidase. Acts as a 1,4-cineole 2-exo-monooxygenase. Possesses low phenacetin O-deethylation activity.
Gene Name:
CYP2A6
Uniprot ID:
P11509
Molecular weight:
56517.005
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in catalase activity
Specific function:
Occurs in almost all aerobically respiring organisms and serves to protect cells from the toxic effects of hydrogen peroxide. Promotes growth of cells including T-cells, B-cells, myeloid leukemia cells, melanoma cells, mastocytoma cells and normal and transformed fibroblast cells.
Gene Name:
CAT
Uniprot ID:
P04040
Molecular weight:
59755.82
References
  1. Thurman RG, McKenna WR, Brentzel HJ Jr, Hesse S: Significant pathways of hepatic ethanol metabolism. Fed Proc. 1975 Oct;34(11):2075-81. [PubMed:240743 ]
  2. Handler JA, Thurman RG: Catalase-dependent ethanol oxidation in perfused rat liver. Requirement for fatty-acid-stimulated H2O2 production by peroxisomes. Eur J Biochem. 1988 Sep 15;176(2):477-84. [PubMed:3416882 ]
  3. Bradford BU, Forman DT, Thurman RG: 4-Methylpyrazole inhibits fatty acyl coenzyme synthetase and diminishes catalase-dependent alcohol metabolism: has the contribution of alcohol dehydrogenase to alcohol metabolism been previously overestimated? Mol Pharmacol. 1993 Jan;43(1):115-9. [PubMed:8423764 ]