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Record Information
Version3.6
Creation Date2012-09-06 15:16:50 UTC
Update Date2016-02-11 01:30:45 UTC
HMDB IDHMDB14956
Secondary Accession NumbersNone
Metabolite Identification
Common NamePropofol
DescriptionPropofol is an intravenous anaesthetic agent used for induction and maintenance of general anaesthesia. IV administration of propfol is used to induce unconsciousness after which anaesthesia may be maintained using a combination of medications. Recovery from propofol-induced anaesthesia is generally rapid and associated with less frequent side effects (e.g. drowsiness, nausea, vomiting) than with thiopental, methohexital, and etomidate. Propofol may be used prior to diagnostic procedures requiring anaesthesia, in the management of refractory status epilepticus, and for induction and/or maintenance of anaesthesia prior to and during surgeries.
Structure
Thumb
Synonyms
ValueSource
2,6-Bis(1-methylethyl)phenolChEBI
2,6-DiisopropylphenolChEBI
DiprivanChEBI
DisoprivanChEBI
DisoprofolChEBI
PropofolumChEBI
RapinovetChEBI
DiisopropylphenolHMDB
Chemical FormulaC12H18O
Average Molecular Weight178.2707
Monoisotopic Molecular Weight178.135765198
IUPAC Name2,6-bis(propan-2-yl)phenol
Traditional Namepropofol
CAS Registry Number2078-54-8
SMILES
CC(C)C1=CC=CC(C(C)C)=C1O
InChI Identifier
InChI=1S/C12H18O/c1-8(2)10-6-5-7-11(9(3)4)12(10)13/h5-9,13H,1-4H3
InChI KeyInChIKey=OLBCVFGFOZPWHH-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as cumenes. These are aromatic compounds containing a prop-2-ylbenzene moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassCumenes
Direct ParentCumenes
Alternative Parents
Substituents
  • Phenylpropane
  • Cumene
  • Phenol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Drug
  • Drug metabolite
Biofunction
  • Anesthetics, Intravenous
  • Anticonvulsants
  • Antiemetics
  • Free Radical Scavengers
  • Hypnotics and Sedatives
  • Waste products
Application
  • Pharmaceutical
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point18 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.58e-01 g/LNot Available
LogP4Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.16 mg/mLALOGPS
logP3.81ALOGPS
logP4.16ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)10.98ChemAxon
pKa (Strongest Basic)-5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity56.42 m3·mol-1ChemAxon
Polarizability21.61 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
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
MSMass Spectrum (Electron Ionization)splash10-03di-2900000000-52d81dde2dccf378a450View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00818
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00818
  • Not Applicable
details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiofluidValueOriginal ageOriginal sexOriginal conditionComments
Blood0-6 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0-3 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00818
DrugBank Metabolite IDDBMET00625
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4774
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPropofol
NuGOwiki LinkHMDB14956
Metagene LinkHMDB14956
METLIN IDNot Available
PubChem Compound4943
PDB IDPFL
ChEBI ID44915
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Vasile B, Rasulo F, Candiani A, Latronico N: The pathophysiology of propofol infusion syndrome: a simple name for a complex syndrome. Intensive Care Med. 2003 Sep;29(9):1417-25. Epub 2003 Aug 6. [12904852 ]
  2. Hong JY, Kang YS, Kil HK: Anaesthesia for day case excisional breast biopsy: propofol-remifentanil compared with sevoflurane-nitrous oxide. Eur J Anaesthesiol. 2008 Jun;25(6):460-7. doi: 10.1017/S026502150800375X. Epub 2008 Feb 26. [18298873 ]
  3. Ke JJ, Zhan J, Feng XB, Wu Y, Rao Y, Wang YL: A comparison of the effect of total intravenous anaesthesia with propofol and remifentanil and inhalational anaesthesia with isoflurane on the release of pro- and anti-inflammatory cytokines in patients undergoing open cholecystectomy. Anaesth Intensive Care. 2008 Jan;36(1):74-8. [18326136 ]
  4. Takahashi O, Hiraga K: 4-tert-butyl-2,6-diisopropylphenol: Another phenol inducing hemorrhage in rats. Toxicol Lett. 1980 Feb;5(2):147-50. [7466839 ]