ContaminantDB: Propofol

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (24)XML

Record Information

Version

1.0

Creation Date

2009-07-21 20:27:43 UTC

Update Date

2026-05-14 16:49:47 UTC

Accession Number

CHEM002280

Identification

Common Name

Propofol

Class

Small Molecule

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.

Contaminant Sources

HMDB Contaminants - Urine
HPV EPA Chemicals
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Anesthetic, Intravenous
Anticonvulsant
Antiemetic
Drug
Free Radical Scavenger
Human Neurotoxin
Hypnotic and Sedative
Metabolite
Organic Compound
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2,6-Bis(1-methylethyl)phenol	ChEBI
2,6-Diisopropylphenol	ChEBI
Diprivan	ChEBI
Disoprivan	ChEBI
Disoprofol	ChEBI
Propofolum	ChEBI
Rapinovet	ChEBI
Diisopropylphenol	HMDB
AstraZeneca brand OF propofol	HMDB
Propofol abbott	HMDB
Recofol	HMDB
2,6 Diisopropylphenol	HMDB
Juste brand OF propofol	HMDB
Pisa brand OF propofol	HMDB
Propofol-lipuro	HMDB
Schering brand OF propofol	HMDB
Alpha Brand OF propofol	HMDB
Fresofol	HMDB
Parnell brand OF propofol	HMDB
Propofol rovi	HMDB
Zeneca brand OF propofol	HMDB
Abbott brand OF propofol	HMDB
Aquafol	HMDB
Astra brand OF propofol	HMDB
Braun brand OF propofol	HMDB
Curamed brand OF propofol	HMDB
Fresenius brand OF propofol	HMDB
Fresenius kabi brand OF propofol	HMDB
Ivofol	HMDB
Propofol fresenius	HMDB
Propofol MCT	HMDB
Rovi brand OF propofol	HMDB

Chemical Formula

C₁₂H₁₈O

Average Molecular Mass

178.271 g/mol

Monoisotopic Mass

178.136 g/mol

CAS Registry Number

2078-54-8

IUPAC Name

2,6-bis(propan-2-yl)phenol

Traditional Name

propofol

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 Key

OLBCVFGFOZPWHH-UHFFFAOYSA-N

Chemical Taxonomy

Description

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

Substituents

Phenylpropane
Cumene
1-hydroxy-4-unsubstituted benzenoid
Phenol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

phenols (CHEBI:44915 )
a small molecule (CPD-11437 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Extracellular
Membrane

Biofluid Locations

Not Available

Tissue Locations

Kidney
Liver

Pathways

Not Available

Applications

Biological Roles

Not Available

Chemical Roles

radical scavenger

Physical Properties

State

Liquid

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	18°C
Boiling Point	256°C
Solubility	124 mg/L

Predicted Properties

Property	Value	Source
Water Solubility	0.16 g/L	ALOGPS
logP	3.81	ALOGPS
logP	4.16	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	10.98	ChemAxon
pKa (Strongest Basic)	-5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	56.42 m³·mol⁻¹	ChemAxon
Polarizability	21.61 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-01t9-4900000000-9238ef924bbbfe181bdc	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0079-8590000000-6ada855df5d0fd97f0b7	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 9V, negative	splash10-004i-0900000000-bf525942be4ead264ece	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 12V, negative	splash10-03di-0900000000-3ab0d6afaf938a81d3dd	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 12V, negative	splash10-001i-0900000000-9e57c7a18ce111c12c63	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0900000000-40f0918750264d7e34e2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-3900000000-fa9d883374aeb7d58af5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01ox-9500000000-08cc06244cce31efd090	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0900000000-d85c9325119ea81302f8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-0900000000-d81a7f98827c18689c1d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-1900000000-40cc01d9032f866dffc1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-3900000000-e19ef26e49a6f11e7a9c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-1900000000-41fb115d031fb4201636	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-002f-9300000000-b212a8d5755ad08fa845	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0900000000-1c420c1b8167732abdd0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-0900000000-585908487fc3aed582c4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-02ta-8900000000-f5810de472ff4197dc17	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-03di-2900000000-52d81dde2dccf378a450	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

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. Parenteral (intravenous injection) (9); inhalation (9) ; dermal (9)

Mechanism of Toxicity

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

Metabolism

Propofol is rapidly distributed into peripheral tissues after absorption. It is highly protein bound in vivo and is metabolised by conjugation in the liver. Propofol is metabolized mainly by glucuronidation by uridine diphosphate-glucuronosyltransferases (UGTs) and by hydroxylation by CYP2B6 and CYP2C enzymes. The enzymes SULT1A1 and NQO1 participate in later steps in propofol metabolism. An unidentified route of extrahepatic metabolism may also exist, suggested by the fact that propofol clearance exceeds estimated hepatic blood flow. (9, 2, 1). Propofol is 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. Route of Elimination: It is chiefly eliminated by hepatic conjugation to inactive metabolites which are excreted by the kidney. Half Life: Initial distribution phase t_1/2α=1.8-9.5 minutes. Second redistirubtion phase t_1/2β=21-70 minutes. Terminal elimination phase t_1/2γ=1.5-31 hours.

Toxicity Values

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)

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Its widespread use as an anesthetic induction agent has largely replaced that of sodium pentothal. It is also commonly used in veterinary medicine. (9). Used for induction and/or maintenance of anaesthesia and for management of refractory status epilepticus.

Minimum Risk Level

Not Available

Health Effects

Mild myoclonic movements are common, as with other intravenous hypnotic agents. Another recently described rare, but serious, side effect is propofol infusion syndrome. This potentially lethal metabolic derangement has been reported in critically-ill patients after a prolonged infusion of high-dose propofol in combination with catecholamines and/or corticosteroids. Overdose of these agents is likely to cause cardiorespiratory depression. (9, 11) They cause slurred speech, disorientation and "drunken" behavior. They are physically and psychologically addictive. May cause a potentially dangerous rash that may develop into Stevens Johnson syndrome, an extremely rare but potentially fatal skin disease.

Symptoms

Aside from the hypotension (mainly through vasodilatation) and transient apnea following induction doses, one of propofol's most frequent side effects is pain on injection, especially in smaller veins. A more serious but rare side effect is dystonia.

Treatment

If overdosage occurs, Propofol administration should be discontinued immediately. Overdosage is likely to cause cardiorespiratory depression. Respiratory depression should be treated by artificial ventilation with oxygen. Cardiovascular depression may require repositioning of the patient by raising the patient's legs, increasing the flow rate of intravenous fluids, and administering pressor agents and/or anticholinergic agents. (13)

Concentrations

Not Available

External Links

DrugBank ID

DB00818

HMDB ID

HMDB0014956

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID