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Record Information
Version3.6
Creation Date2012-09-06 15:16:50 UTC
Update Date2017-03-02 21:33:31 UTC
HMDB IDHMDB14871
Secondary Accession NumbersNone
Metabolite Identification
Common NamePralidoxime
DescriptionPralidoxime is an antidote to organophosphate pesticides and chemicals. Organophosphates bind to the esteratic site of acetylcholinesterase, which results initially in reversible inactivation of the enzyme. If given within 24 hours,after organophosphate exposure, pralidoxime reactivates the enzyme cholinesterase by cleaving the phosphate-ester bond formed between the organophosphate and acetylcholinesterase.
Structure
Thumb
Synonyms
ValueSource
PralidoximumChEBI
Pralidoxime chlorideHMDB
Chemical FormulaC7H9N2O
Average Molecular Weight137.1592
Monoisotopic Molecular Weight137.07148792
IUPAC Name2-[(1E)-(hydroxyimino)methyl]-1-methylpyridin-1-ium
Traditional Namepralidoximum
CAS Registry Number6735-59-7
SMILES
C[N+]1=C(\C=N\O)C=CC=C1
InChI Identifier
InChI=1S/C7H8N2O/c1-9-5-3-2-4-7(9)6-8-10/h2-6H,1H3/p+1
InChI KeyJBKPUQTUERUYQE-UHFFFAOYSA-O
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as n-methylpyridinium compounds. These are methylpyridines that carry a methyl group at the 1-position.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassPyridines and derivatives
Direct ParentN-methylpyridinium compounds
Alternative Parents
Substituents
  • N-methylpyridinium
  • Pyridinium
  • Heteroaromatic compound
  • Aldoxime
  • Azacycle
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organic cation
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Drug
Biofunction
  • Antidotes
  • Cholinesterase Reactivators
Application
  • Pharmaceutical
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point215 - 225 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.49e-01 g/LNot Available
LogP1.564Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.15 mg/mLALOGPS
logP-3ALOGPS
logP-3.3ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)5.78ChemAxon
pKa (Strongest Basic)-1.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area36.47 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity40.33 m3·mol-1ChemAxon
Polarizability14.44 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000i-0900000000-20fdfd5334ead907481eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00kr-1900000000-28213070bfa027f76396View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00kf-9600000000-e526d65f27b45380a401View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-9100000000-5b6d1f4a0b4b4f3b44d8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-014l-9000000000-dcac00013d3eaf2dd6d9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00ko-4900000000-030938e55f082376a8fcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00kf-9200000000-7ee2419716b3f943ce85View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00733
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00733
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00733
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5193737
KEGG Compound IDC07400
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPralidoxime
NuGOwiki LinkHMDB14871
Metagene LinkHMDB14871
METLIN IDNot Available
PubChem Compound6789253
PDB IDNot Available
ChEBI ID8354
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in carboxylesterase activity
Specific function:
Terminates signal transduction at the neuromuscular junction by rapid hydrolysis of the acetylcholine released into the synaptic cleft. Role in neuronal apoptosis.
Gene Name:
ACHE
Uniprot ID:
P22303
Molecular weight:
67795.525
References
  1. Jokanovic M, Prostran M: Pyridinium oximes as cholinesterase reactivators. Structure-activity relationship and efficacy in the treatment of poisoning with organophosphorus compounds. Curr Med Chem. 2009;16(17):2177-88. [PubMed:19519385 ]
  2. Kovacic P: Mechanism of organophosphates (nerve gases and pesticides) and antidotes: electron transfer and oxidative stress. Curr Med Chem. 2003 Dec;10(24):2705-9. [PubMed:14529460 ]
  3. Jokanovic M: Medical treatment of acute poisoning with organophosphorus and carbamate pesticides. Toxicol Lett. 2009 Oct 28;190(2):107-15. doi: 10.1016/j.toxlet.2009.07.025. Epub 2009 Aug 3. [PubMed:19651196 ]
  4. Wong L, Radic Z, Bruggemann RJ, Hosea N, Berman HA, Taylor P: Mechanism of oxime reactivation of acetylcholinesterase analyzed by chirality and mutagenesis. Biochemistry. 2000 May 16;39(19):5750-7. [PubMed:10801325 ]
General function:
Involved in carboxylesterase activity
Specific function:
Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters.
Gene Name:
BCHE
Uniprot ID:
P06276
Molecular weight:
68417.575
References
  1. Pohanka M, Jun D, Kuca K: In vitro reactivation of trichlorfon-inhibited butyrylcholinesterase using HI-6, obidoxime, pralidoxime and K048. J Enzyme Inhib Med Chem. 2009 Jun;24(3):680-3. doi: 10.1080/14756360802328315. [PubMed:18825528 ]
  2. Khan S, Hemalatha R, Jeyaseelan L, Oommen A, Zachariah A: Neuroparalysis and oxime efficacy in organophosphate poisoning: a study of butyrylcholinesterase. Hum Exp Toxicol. 2001 Apr;20(4):169-74. [PubMed:11393267 ]