Identification

Name
Propofol
Accession Number
DB00818
Description

Propofol 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.

Type
Small Molecule
Groups
Approved, Investigational, Vet approved
Structure
Thumb
Weight
Average: 178.2707
Monoisotopic: 178.135765198
Chemical Formula
C12H18O
Synonyms
  • 2,6-bis(1-methylethyl)phenol
  • 2,6-Diisopropylphenol
  • Propofol
  • Propofolum
External IDs
  • ICI 35-868
  • ICI 35,868
  • ICI 35868
  • ICI-35868
  • ICI35,868

Pharmacology

Indication

Used for induction and/or maintenance of anaesthesia and for management of refractory status epilepticus.

Associated Therapies
Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
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Pharmacodynamics

Propofol is a sedative-hypnotic agent for use in the induction and maintenance of anesthesia or sedation. Intravenous injection of a therapeutic dose of propofol produces hypnosis rapidly with minimal excitation, usually within 40 seconds from the start of an injection (the time for one arm-brain circulation).

Mechanism of action

The action of propofol involves a positive modulation of the inhibitory function of the neurotransmitter gama-aminobutyric acid (GABA) through GABA-A receptors.

TargetActionsOrganism
AGamma-aminobutyric acid receptor subunit beta-2
potentiator
Humans
AGamma-aminobutyric acid receptor subunit beta-3
potentiator
Humans
USodium channel protein type 4 subunit alpha
inhibitor
Humans
USodium channel protein type 2 subunit alpha
inhibitor
Humans
AGABA(A) Receptor
positive allosteric modulator
Humans
Absorption

Rapid - time to onset of unconsciousness is 15-30 seconds, due to rapid distribution from plasma to the CNS. Distribution is so rapid that peak plasma concentrations cannot be readily measured. Duration of action is 5-10 minutes.

Volume of distribution
  • 60 L/kg [healthy adults]
Protein binding

95 to 99%, primarily to serum albumin and hemoglobin

Metabolism

Hepatically metabolized mainly by glucuronidation at the C1-hydroxyl. Hydroxylation of the benzene ring to 4-hydroxypropofol may also occur via CYP2B6 and 2C9 with subsequent conjugation to sulfuric and/or glucuronic acid. Hydroxypropofol has approximately 1/3 of hypnotic activity of propofol.

Hover over products below to view reaction partners

Route of elimination

It is chiefly eliminated by hepatic conjugation to inactive metabolites which are excreted by the kidney.

Half-life

Initial distribution phase t1/2α=1.8-9.5 minutes. Second redistirubtion phase t1/2β=21-70 minutes. Terminal elimination phase t1/2γ=1.5-31 hours.

Clearance
  • 23 - 50 mL/kg/min
  • 1.6 - 3.4 L/min [70 Kg adults]
Adverse Effects
Learn about our commercial Adverse Effects data.
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Toxicity

Overdosage may increase pharmacologic and adverse effects or cause death.

IV LD50=53 mg/kg (mice), 42 mg/kg (rats). Oral LD50 (as a solution in soybean oil)=1230 mg/kg (mice), 600 mg/kg (rats)

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbacavirThe metabolism of Abacavir can be decreased when combined with Propofol.
AbametapirThe serum concentration of Propofol can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Propofol can be increased when combined with Abatacept.
AbemaciclibThe metabolism of Abemaciclib can be decreased when combined with Propofol.
AbirateroneThe metabolism of Propofol can be decreased when combined with Abiraterone.
AcalabrutinibThe metabolism of Acalabrutinib can be decreased when combined with Propofol.
AcebutololThe risk or severity of QTc prolongation can be increased when Propofol is combined with Acebutolol.
AceclofenacThe risk or severity of hypertension can be increased when Propofol is combined with Aceclofenac.
AcemetacinThe risk or severity of hypertension can be increased when Propofol is combined with Acemetacin.
AcenocoumarolThe serum concentration of Acenocoumarol can be increased when it is combined with Propofol.
Additional Data Available
  • Extended Description
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  • Severity
    Severity
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  • Evidence Level
    Evidence Level
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  • Action
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Food Interactions
No interactions found.

Products

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International/Other Brands
Anepol (Ha Na Pharm) / Anespro (Behrens) / Anesvan (Chi Sheng) / Critifol (Abbott) / Disoprivan (AstraZeneca) / Disoprofol / Dormofol (Actavis) / Fresofol (Boryung) / Gobbifol (Gobbi) / Hipnolam (AC Farma) / Hypro (Celon) / IV-Pro (Claris Lifesciences) / Lipuro (B. Braun Medical) / Oleo-Lax (Fada) / Plofed (Warsaw Pharmaceutical Works) / Profol (Biogalenic) / Profolen (Blausiegel) / Propofabb (Hospira) / Propofil (Alvia) / Propogen (Genepharm) / Propolipid (Fresenius) / Propovan (Bharat Serums) / Propoven (Fresenius) / Provive (AFT) / Rapinovet / Recofol (Bayer) / Safol (Novell) / Trivam (Hana Pharm) / Troypofol (Troikaa) / Unifol (Claris Lifesciences)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
DiprivanInjection, emulsion10 mg/1mLIntravenousFresenius Kabi USA, LLC2009-11-17Not applicableUS flag
DiprivanInjection, emulsion10 mg/1mLIntravenousGeneral Injectables & Vaccines2010-03-01Not applicableUS flag
DiprivanInjection, emulsion10 mg/1mLIntravenousFresenius Kabi USA, LLC2020-01-13Not applicableUS flag
DiprivanInjection, emulsion10 mg/1mLIntravenousAstra Zeneca Lp1996-06-242010-10-31US flag
Diprivan 1%EmulsionIntravenousAspen Pharmacare Canada Inc.1993-12-31Not applicableCanada flag
Fresenius Propoven 2%Emulsion20 mg/1mLIntravenousFresenius Kabi USA, LLC2020-06-05Not applicableUS flag
Fresenius Propoven 2%Emulsion20 mg/1mLIntravenousFresenius Kabi Austria GmbH2020-06-05Not applicableUS flag
PropofolEmulsion10 mgIntravenousBaxter Laboratories2018-04-24Not applicableCanada flag
PropofolInjection, emulsion10 mg/1mLIntravenousFresenius Kabi USA, LLC2009-10-232013-07-22US flag
Propofol InjectionEmulsionIntravenousPfizer Canada Ulc1998-02-052020-02-21Canada flag
Additional Data Available
  • Application Number
    Application Number
    Available for Purchase

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code
    Available for Purchase

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
PropofolInjection, emulsion10 mg/1mLIntravenousHikma Pharmaceuticals USA Inc.2020-05-01Not applicableUS flag
PropofolInjection, emulsion10 mg/1mLIntravenousTeva Parenteral Medicines, Inc.2007-06-212016-04-30US flag
PropofolInjection, emulsion10 mg/1mLIntravenousHospira, Inc.2006-04-03Not applicableUS flag
PropofolInjection, emulsion10 mg/1mLIntravenousHF Acquisition Co LLC, DBA HealthFirst2019-12-14Not applicableUS flag
PropofolInjection, emulsion10 mg/1mLIntravenousSagent Pharmaceuticals2014-07-01Not applicableUS flag
PropofolInjection, emulsion10 mg/1mLIntravenousPfizer Laboratories Div Pfizer Inc2020-10-05Not applicableUS flag
PropofolInjection, emulsion10 mg/1mLIntravenousActavis Pharma, Inc.2016-01-07Not applicableUS flag
PropofolInjection, emulsion10 mg/1mLIntravenousHikma Pharmaceuticals USA Inc.2020-05-01Not applicableUS flag
PropofolInjection, emulsion10 mg/1mLIntravenousTeva Parenteral Medicines, Inc.2007-06-212015-11-30US flag
PropofolInjection, emulsion10 mg/1mLIntravenousHF Acquisition Co LLC, DBA HealthFirst2019-12-15Not applicableUS flag
Additional Data Available
  • Application Number
    Application Number
    Available for Purchase

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code
    Available for Purchase

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Anesthesia S/I-40Propofol (10 mg/1mL) + Isopropyl alcohol (0.7 mL/1mL)Intravenous; TopicalRX PHARMA-PACK, INC.2017-08-24Not applicableUS flag
Anesthesia S/I-50Propofol (10 mg/1mL) + Isopropyl alcohol (0.7 mL/1mL)Intravenous; TopicalRX PHARMA-PACK, INC.2017-06-162018-12-14US flag
Anesthesia S/I-60Propofol (10 mg/1mL) + Isopropyl alcohol (0.7 mL/1mL)Intravenous; TopicalRX PHARMA-PACK, INC.2017-06-16Not applicableUS flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Fresenius Propoven 2%Propofol (20 mg/1mL)EmulsionIntravenousFresenius Kabi USA, LLC2020-06-05Not applicableUS flag
Fresenius Propoven 2%Propofol (20 mg/1mL)EmulsionIntravenousFresenius Kabi Austria GmbH2020-06-05Not applicableUS flag
PropovenPropofol (10 mg/1mL)InjectionIntravenousAPP Pharmaceuticals, LLC2012-07-012015-06-30US flag

Categories

ATC Codes
N01AX10 — Propofol
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as cumenes. These are aromatic compounds containing a prop-2-ylbenzene moiety.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Cumenes
Direct Parent
Cumenes
Alternative Parents
Phenylpropanes / 1-hydroxy-4-unsubstituted benzenoids / Organooxygen compounds / Hydrocarbon derivatives
Substituents
1-hydroxy-4-unsubstituted benzenoid / Aromatic homomonocyclic compound / Cumene / Hydrocarbon derivative / Organic oxygen compound / Organooxygen compound / Phenol / Phenylpropane
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
phenols (CHEBI:44915) / a small molecule (CPD-11437)

Chemical Identifiers

UNII
YI7VU623SF
CAS number
2078-54-8
InChI Key
OLBCVFGFOZPWHH-UHFFFAOYSA-N
InChI
InChI=1S/C12H18O/c1-8(2)10-6-5-7-11(9(3)4)12(10)13/h5-9,13H,1-4H3
IUPAC Name
2,6-bis(propan-2-yl)phenol
SMILES
CC(C)C1=CC=CC(C(C)C)=C1O

References

Synthesis Reference

John R. Carpenter, "Propofol-based anesthetic and method of making same." U.S. Patent US6150423, issued May, 1977.

US6150423
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. [PubMed:12904852]
  2. 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. [PubMed:18326136]
  3. 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. [PubMed:18298873]
Human Metabolome Database
HMDB0014956
KEGG Drug
D00549
KEGG Compound
C07523
PubChem Compound
4943
PubChem Substance
46504991
ChemSpider
4774
BindingDB
50058046
RxNav
8782
ChEBI
44915
ChEMBL
CHEMBL526
ZINC
ZINC000000968303
Therapeutic Targets Database
DAP000662
PharmGKB
PA451141
PDBe Ligand
PFL
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Propofol
AHFS Codes
  • 28:04.92 — Miscellaneous General Anesthetics
PDB Entries
1e7a / 3f33 / 3p50 / 5muo / 5mur / 5mvm / 5mvn / 5mzr / 6x3t
FDA label
Download (168 KB)
MSDS
Download (71.9 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Active Not RecruitingHealth Services ResearchCerebral Palsy (CP) / Developmental Delays / Epilepsies1
4Active Not RecruitingOtherHealthy Volunteers1
4Active Not RecruitingPreventionLong-Term Effects Secondary to Cancer Therapy in Adults1
4Active Not RecruitingTreatmentDriving Performance After Minor Ambulatory Surgery / Minor Surgical Procedures With Monitored Anesthesia Care1
4CompletedNot AvailableDigestive System Diseases / Disorientation1
4CompletedNot AvailableDisorders of Gallbladder, Biliary Tract and Pancrease1
4CompletedNot AvailableFailed Moderate Sedation During Procedure1
4CompletedNot AvailableIdiopathic Scoliosis / Neuromuscular Dystrophy / Spine Deformity1
4CompletedNot AvailableInflammatory Reaction1
4CompletedNot AvailableNon Cardiac Surgery1

Pharmacoeconomics

Manufacturers
  • App pharmaceuticals llc
  • Bedford laboratories div ben venue laboratories inc
  • Hospira inc
  • Teva parenteral medicines inc
Packagers
  • APP Pharmaceuticals
  • AstraZeneca Inc.
  • Baxter International Inc.
  • Cardinal Health
  • Hospira Inc.
  • Pfizer Inc.
  • Sicor Pharmaceuticals
  • Teva Pharmaceutical Industries Ltd.
Dosage Forms
FormRouteStrength
Injection, emulsionIntravenous120 mg/12mL
EmulsionIntravenous; Parenteral10 MG/ML
InjectionIntravenous1 %
InjectionIntravenous2 %
EmulsionIntravenous20 mg/1mL
Injection, emulsionIntravenous1 g/50mL
Injection, emulsionIntravenous400 mg/20mL
Injection, emulsionIntravenous500 mg/50mL
EmulsionIntravenous0.5 g
EmulsionIntravenous1 g
EmulsionIntravenous200 mg/20ml
Injection, solutionIntravenous500 mg/50mL
Injection, emulsionIntravenous10 mg/1mL
Injection, emulsionIntravenous200 mg/20mL
Injection, emulsionIntravenous1 %
Injection, solutionIntravenous1 %
Injection, emulsionIntravenous2 %
Injection, solutionIntravenous2 %
EmulsionIntravenous1 %
EmulsionIntravenous2 %
EmulsionIntravenous10 mg
EmulsionParenteral1 %
EmulsionParenteral2 %
EmulsionParenteral5 MG/ML
Injection, emulsionParenteral1 %
Injection, emulsionParenteral2 %
Injection, emulsionIntravenous1 % w/v
InjectionIntravenous1000 mg/100ml
InjectionIntravenous200 mg/20ml
InjectionIntravenous500 mg/50ml
EmulsionIntravenous
Injection, solutionIntravenous1 g/100mL
InjectionIntravenous10 mg/ml
Injection, emulsionIntravenous10 mg/ml
Injection, emulsionIntravenous20 mg/ml
Injection, emulsionIntravenous5 mg/ml
Injection, emulsionIntravenous100 g/10mL
InjectionIntravenous10 mg/1mL
InjectionIntravenous1 % w/v
EmulsionIntravenous200 mg
EmulsionParenteral10 MG/ML
EmulsionParenteral20 MG/ML
Prices
Unit descriptionCostUnit
Diprivan 10 mg/ml vial0.93USD ml
Propoven 1000 mg/100 ml vial0.19USD ml
Propoven 200 mg/20 ml ampul0.19USD ml
Propoven 500 mg/50 ml vial0.19USD ml
Propofol 10 mg/ml vial0.13USD ml
Propofol 1% emulsion vial0.1USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
CA2212794No2000-09-122015-03-17Canada flag
US8476010Yes2013-07-022025-06-01US flag
US5908869Yes1999-06-012015-09-22US flag
US5731356Yes1998-03-242015-09-22US flag
US5731355Yes1998-03-242015-09-22US flag
US5714520Yes1998-02-032015-09-22US flag
Additional Data Available
  • Filed On
    Filed On
    Available for Purchase

    The date on which a patent was filed with the relevant government.

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Properties

State
Liquid
Experimental Properties
PropertyValueSource
melting point (°C)18 °CPhysProp
boiling point (°C)256 °CPhysProp
water solubility124 mg/LNot Available
logP3.79HANSCH,C ET AL. (1995)
pKa11.1 (at 20 °C)SERJEANT,EP & DEMPSEY,B (1979)
Predicted Properties
PropertyValueSource
Water Solubility0.158 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 RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9955
Blood Brain Barrier+0.9381
Caco-2 permeable+0.9153
P-glycoprotein substrateNon-substrate0.722
P-glycoprotein inhibitor INon-inhibitor0.9343
P-glycoprotein inhibitor IINon-inhibitor0.9883
Renal organic cation transporterNon-inhibitor0.9036
CYP450 2C9 substrateNon-substrate0.7352
CYP450 2D6 substrateSubstrate0.7838
CYP450 3A4 substrateNon-substrate0.5667
CYP450 1A2 substrateInhibitor0.9107
CYP450 2C9 inhibitorNon-inhibitor0.907
CYP450 2D6 inhibitorNon-inhibitor0.9368
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorNon-inhibitor0.9196
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7429
Ames testNon AMES toxic0.9282
CarcinogenicityNon-carcinogens0.7195
BiodegradationNot ready biodegradable0.7808
Rat acute toxicity2.2996 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8987
hERG inhibition (predictor II)Non-inhibitor0.9087
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (7.9 KB)
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Mass Spectrum (Electron Ionization)MSsplash10-03di-2900000000-52d81dde2dccf378a450
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Potentiator
General Function
Inhibitory extracellular ligand-gated ion channel activity
Specific Function
Component of the heteropentameric receptor for GABA, the major inhibitory neurotransmitter in the vertebrate brain. Functions also as histamine receptor and mediates cellular responses to histamine...
Gene Name
GABRB2
Uniprot ID
P47870
Uniprot Name
Gamma-aminobutyric acid receptor subunit beta-2
Molecular Weight
59149.895 Da
References
  1. Franks NP: Molecular targets underlying general anaesthesia. Br J Pharmacol. 2006 Jan;147 Suppl 1:S72-81. [PubMed:16402123]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Potentiator
General Function
Gaba-gated chloride ion channel activity
Specific Function
Component of the heteropentameric receptor for GABA, the major inhibitory neurotransmitter in the vertebrate brain. Functions also as histamine receptor and mediates cellular responses to histamine...
Gene Name
GABRB3
Uniprot ID
P28472
Uniprot Name
Gamma-aminobutyric acid receptor subunit beta-3
Molecular Weight
54115.04 Da
References
  1. Franks NP: Molecular targets underlying general anaesthesia. Br J Pharmacol. 2006 Jan;147 Suppl 1:S72-81. [PubMed:16402123]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Voltage-gated sodium channel activity
Specific Function
This protein mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the pr...
Gene Name
SCN4A
Uniprot ID
P35499
Uniprot Name
Sodium channel protein type 4 subunit alpha
Molecular Weight
208059.175 Da
References
  1. Haeseler G, Karst M, Foadi N, Gudehus S, Roeder A, Hecker H, Dengler R, Leuwer M: High-affinity blockade of voltage-operated skeletal muscle and neuronal sodium channels by halogenated propofol analogues. Br J Pharmacol. 2008 Sep;155(2):265-75. doi: 10.1038/bjp.2008.255. Epub 2008 Jun 23. [PubMed:18574460]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Voltage-gated sodium channel activity
Specific Function
Mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a...
Gene Name
SCN2A
Uniprot ID
Q99250
Uniprot Name
Sodium channel protein type 2 subunit alpha
Molecular Weight
227972.64 Da
References
  1. Haeseler G, Karst M, Foadi N, Gudehus S, Roeder A, Hecker H, Dengler R, Leuwer M: High-affinity blockade of voltage-operated skeletal muscle and neuronal sodium channels by halogenated propofol analogues. Br J Pharmacol. 2008 Sep;155(2):265-75. doi: 10.1038/bjp.2008.255. Epub 2008 Jun 23. [PubMed:18574460]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. Mikstacki A, Zakerska-Banaszak O, Skrzypczak-Zielinska M, Tamowicz B, Prendecki M, Dorszewska J, Molinska-Glura M, Waszak M, Slomski R: The effect of UGT1A9, CYP2B6 and CYP2C9 genes polymorphism on individual differences in propofol pharmacokinetics among Polish patients undergoing general anaesthesia. J Appl Genet. 2017 May;58(2):213-220. doi: 10.1007/s13353-016-0373-2. Epub 2016 Nov 8. [PubMed:27826892]
  2. Ouchi K, Sugiyama K: Required propofol dose for anesthesia and time to emerge are affected by the use of antiepileptics: prospective cohort study. BMC Anesthesiol. 2015 Mar 15;15:34. doi: 10.1186/s12871-015-0006-z. eCollection 2015. [PubMed:25788855]
  3. Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [PubMed:11996015]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2B6
Uniprot ID
P20813
Uniprot Name
Cytochrome P450 2B6
Molecular Weight
56277.81 Da
References
  1. Mourao AL, de Abreu FG, Fiegenbaum M: Impact of the Cytochrome P450 2B6 (CYP2B6) Gene Polymorphism c.516G>T (rs3745274) on Propofol Dose Variability. Eur J Drug Metab Pharmacokinet. 2016 Oct;41(5):511-5. doi: 10.1007/s13318-015-0289-y. [PubMed:26141406]
  2. Eugene AR: CYP2B6 Genotype Guided Dosing of Propofol Anesthesia in the Elderly based on Nonparametric Population Pharmacokinetic Modeling and Simulations. Int J Clin Pharmacol Toxicol. 2017;6(1):242-249. Epub 2017 Jan 3. [PubMed:28154789]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid binding
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Isoform 2 lacks transferase activity but acts as a negative reg...
Gene Name
UGT1A8
Uniprot ID
Q9HAW9
Uniprot Name
UDP-glucuronosyltransferase 1-8
Molecular Weight
59741.035 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Retinoic acid binding
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols. Isoform 2 lacks trans...
Gene Name
UGT1A9
Uniprot ID
O60656
Uniprot Name
UDP-glucuronosyltransferase 1-9
Molecular Weight
59940.495 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
  2. Takahashi H, Maruo Y, Mori A, Iwai M, Sato H, Takeuchi Y: Effect of D256N and Y483D on propofol glucuronidation by human uridine 5'-diphosphate glucuronosyltransferase (UGT1A9). Basic Clin Pharmacol Toxicol. 2008 Aug;103(2):131-6. doi: 10.1111/j.1742-7843.2008.00247.x. [PubMed:18816295]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Steroid binding
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the...
Gene Name
UGT1A1
Uniprot ID
P22309
Uniprot Name
UDP-glucuronosyltransferase 1-1
Molecular Weight
59590.91 Da
References
  1. Mano Y, Usui T, Kamimura H: Substrate-dependent modulation of UDP-glucuronosyltransferase 1A1 (UGT1A1) by propofol in recombinant human UGT1A1 and human liver microsomes. Basic Clin Pharmacol Toxicol. 2007 Sep;101(3):211-4. [PubMed:17697043]
  2. Williams JA, Hyland R, Jones BC, Smith DA, Hurst S, Goosen TC, Peterkin V, Koup JR, Ball SE: Drug-drug interactions for UDP-glucuronosyltransferase substrates: a pharmacokinetic explanation for typically observed low exposure (AUCi/AUC) ratios. Drug Metab Dispos. 2004 Nov;32(11):1201-8. doi: 10.1124/dmd.104.000794. Epub 2004 Aug 10. [PubMed:15304429]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Fatty acid amide hydrolase activity
Specific Function
Degrades bioactive fatty acid amides like oleamide, the endogenous cannabinoid, anandamide and myristic amide to their corresponding acids, thereby serving to terminate the signaling functions of t...
Gene Name
FAAH
Uniprot ID
O00519
Uniprot Name
Fatty-acid amide hydrolase 1
Molecular Weight
63065.28 Da
References
  1. Zhu F, Han B, Kumar P, Liu X, Ma X, Wei X, Huang L, Guo Y, Han L, Zheng C, Chen Y: Update of TTD: Therapeutic Target Database. Nucleic Acids Res. 2010 Jan;38(Database issue):D787-91. doi: 10.1093/nar/gkp1014. Epub 2009 Nov 20. [PubMed:19933260]
  2. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid hydroxylase 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 ...
Gene Name
CYP2E1
Uniprot ID
P05181
Uniprot Name
Cytochrome P450 2E1
Molecular Weight
56848.42 Da
References
  1. Chen TL, Ueng TH, Chen SH, Lee PH, Fan SZ, Liu CC: Human cytochrome P450 mono-oxygenase system is suppressed by propofol. Br J Anaesth. 1995 May;74(5):558-62. [PubMed:7772432]
  2. Lejus C, Fautrel A, Malledant Y, Guillouzo A: Inhibition of cytochrome P450 2E1 by propofol in human and porcine liver microsomes. Biochem Pharmacol. 2002 Oct 1;64(7):1151-6. doi: 10.1016/s0006-2952(02)01226-1. [PubMed:12234619]
  3. Yang LQ, Yu WF, Cao YF, Gong B, Chang Q, Yang GS: Potential inhibition of cytochrome P450 3A4 by propofol in human primary hepatocytes. World J Gastroenterol. 2003 Sep;9(9):1959-62. doi: 10.3748/wjg.v9.i9.1959. [PubMed:12970884]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Oxygen binding
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1B1
Uniprot ID
Q16678
Uniprot Name
Cytochrome P450 1B1
Molecular Weight
60845.33 Da
References
  1. Chen TL, Ueng TH, Chen SH, Lee PH, Fan SZ, Liu CC: Human cytochrome P450 mono-oxygenase system is suppressed by propofol. Br J Anaesth. 1995 May;74(5):558-62. [PubMed:7772432]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Vitamin d 24-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1A1
Uniprot ID
P04798
Uniprot Name
Cytochrome P450 1A1
Molecular Weight
58164.815 Da
References
  1. Chen TL, Ueng TH, Chen SH, Lee PH, Fan SZ, Liu CC: Human cytochrome P450 mono-oxygenase system is suppressed by propofol. Br J Anaesth. 1995 May;74(5):558-62. [PubMed:7772432]
  2. Campos SP, de Lurdes Pinto M, Gomes G, de Pinho PG, Monteiro JA, Felix LM, Branco PS, Ferreira LM, Antunes LM: Expression of CYP1A1 and CYP1A2 in the liver and kidney of rabbits after prolonged infusion of propofol. Exp Toxicol Pathol. 2016 Oct;68(9):521-531. doi: 10.1016/j.etp.2016.07.006. Epub 2016 Aug 13. [PubMed:27531257]
  3. Yang LQ, Yu WF, Cao YF, Gong B, Chang Q, Yang GS: Potential inhibition of cytochrome P450 3A4 by propofol in human primary hepatocytes. World J Gastroenterol. 2003 Sep;9(9):1959-62. doi: 10.3748/wjg.v9.i9.1959. [PubMed:12970884]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
Curator comments
Current data available supporting this enzyme action are in vitro studies.
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
Molecular Weight
58293.76 Da
References
  1. McKillop D, Wild MJ, Butters CJ, Simcock C: Effects of propofol on human hepatic microsomal cytochrome P450 activities. Xenobiotica. 1998 Sep;28(9):845-53. doi: 10.1080/004982598239092 . [PubMed:9764927]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C18
Uniprot ID
P33260
Uniprot Name
Cytochrome P450 2C18
Molecular Weight
55710.075 Da
References
  1. Dinis-Oliveira RJ: Metabolic Profiles of Propofol and Fospropofol: Clinical and Forensic Interpretative Aspects. Biomed Res Int. 2018 May 24;2018:6852857. doi: 10.1155/2018/6852857. eCollection 2018. [PubMed:29992157]
  2. Guitton J, Buronfosse T, Desage M, Flinois JP, Perdrix JP, Brazier JL, Beaune P: Possible involvement of multiple human cytochrome P450 isoforms in the liver metabolism of propofol. Br J Anaesth. 1998 Jun;80(6):788-95. doi: 10.1093/bja/80.6.788. [PubMed:9771309]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55930.545 Da
References
  1. Guitton J, Buronfosse T, Desage M, Flinois JP, Perdrix JP, Brazier JL, Beaune P: Possible involvement of multiple human cytochrome P450 isoforms in the liver metabolism of propofol. Br J Anaesth. 1998 Jun;80(6):788-95. doi: 10.1093/bja/80.6.788. [PubMed:9771309]
  2. Ouchi K, Sugiyama K: Required propofol dose for anesthesia and time to emerge are affected by the use of antiepileptics: prospective cohort study. BMC Anesthesiol. 2015 Mar 15;15:34. doi: 10.1186/s12871-015-0006-z. eCollection 2015. [PubMed:25788855]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C8
Uniprot ID
P10632
Uniprot Name
Cytochrome P450 2C8
Molecular Weight
55824.275 Da
References
  1. Guitton J, Buronfosse T, Desage M, Flinois JP, Perdrix JP, Brazier JL, Beaune P: Possible involvement of multiple human cytochrome P450 isoforms in the liver metabolism of propofol. Br J Anaesth. 1998 Jun;80(6):788-95. doi: 10.1093/bja/80.6.788. [PubMed:9771309]
  2. Cancer.gov CTEP document [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Protein homodimerization activity
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols. Isoform 3 lacks trans...
Gene Name
UGT1A6
Uniprot ID
P19224
Uniprot Name
UDP-glucuronosyltransferase 1-6
Molecular Weight
60750.215 Da
References
  1. Gu J, Lu K, Xia P, Tang M, Dai Q, Ma D, Tao G: Pharmacokinetics of propofol and extrahepatic UGT1A6 gene expression in anhepatic rats. Pharmacology. 2009;84(4):219-26. doi: 10.1159/000236523. Epub 2009 Sep 10. [PubMed:19752585]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
No
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. Bright DP, Adham SD, Lemaire LC, Benavides R, Gruss M, Taylor GW, Smith EH, Franks NP: Identification of anesthetic binding sites on human serum albumin using a novel etomidate photolabel. J Biol Chem. 2007 Apr 20;282(16):12038-47. Epub 2007 Feb 20. [PubMed:17311911]
  2. Liu R, Eckenhoff RG: Weak polar interactions confer albumin binding site selectivity for haloether anesthetics. Anesthesiology. 2005 Apr;102(4):799-805. [PubMed:15791110]
  3. Sawas AH, Pentyala SN, Rebecchi MJ: Binding of volatile anesthetics to serum albumin: measurements of enthalpy and solvent contributions. Biochemistry. 2004 Oct 5;43(39):12675-85. [PubMed:15449957]
  4. Schywalsky M, Ihmsen H, Knoll R, Schwilden H: Binding of propofol to human serum albumin. Arzneimittelforschung. 2005;55(6):303-6. [PubMed:16032968]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inducer
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Regev R, Katzir H, Yeheskely-Hayon D, Eytan GD: Modulation of P-glycoprotein-mediated multidrug resistance by acceleration of passive drug permeation across the plasma membrane. FEBS J. 2007 Dec;274(23):6204-14. doi: 10.1111/j.1742-4658.2007.06140.x. Epub 2007 Nov 6. [PubMed:17986257]

Drug created on June 13, 2005 07:24 / Updated on November 25, 2020 15:47

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