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Details

Stereochemistry ACHIRAL
Molecular Formula C12H18O
Molecular Weight 178.2707
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PROPOFOL

SMILES

CC(C)C1=CC=CC(C(C)C)=C1O

InChI

InChIKey=OLBCVFGFOZPWHH-UHFFFAOYSA-N
InChI=1S/C12H18O/c1-8(2)10-6-5-7-11(9(3)4)12(10)13/h5-9,13H,1-4H3

HIDE SMILES / InChI

Molecular Formula C12H18O
Molecular Weight 178.2707
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Propofol (2,6-diisopropylphenol) 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. It is extensively metabolized, with most of the administered dose appearing in the urine as glucuronide conjugates. Favorable operating conditions and rapid recovery are claimed as the main advantages in using propofol, whereas disadvantages include a relatively high incidence of apnea, and blood pressure reductions. The action of propofol involves a positive modulation of the inhibitory function of the neurotransmitter gama-aminobutyric acid (GABA) through GABA-A receptors. Due to its high lipid-solubility, propofol was initially formulated as a solution with the surfactant Cremophor EL, but the occurrence of pain on injection and anaphylactoid reactions prompted to search for alternative formulations. Results from using cyclodextrins, water-soluble prodrugs, and adopting Bodor's approach to the site-specific chemical delivery system (CDS), as well as the advantages provided by computer-controlled infusion systems, are examined in some detail.

CNS Activity

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
DIPRIVAN
PubMed

PubMed

TitleDatePubMed
[Preliminary report: the effect of flumazenil on the hypnotic dose of propofol in ddY mice].
2001 Feb
A randomized prospective comparative study of general versus epidural anesthesia for transcervical hysteroscopic endometrial resection.
2001 Feb
Propofol in subanesthetic doses terminates status epilepticus in a rodent model.
2001 Feb
Timing of pre-emptive tenoxicam is important for postoperative analgesia.
2001 Feb
High concentrations of isoflurane do not block the sympathetic nervous system activation from desflurane.
2001 Feb
Evaluation of the effective drugs for the prevention of nausea and vomiting induced by morphine used for postoperative pain: a quantitative systematic review.
2001 Feb
Relation between initial blood distribution volume and propofol induction dose requirement.
2001 Feb
Effect of dexmedetomidine on propofol requirements in healthy subjects.
2001 Feb
Effect of midazolam pretreatment on induction dose requirements of propofol in combination with fentanyl in younger and older adults.
2001 Feb
Reversal of rocuronium with edrophonium during propofol versus sevoflurane anesthesia.
2001 Feb
Effects of different preparations of propofol, diazepam, and etomidate on human neutrophils in vitro.
2001 Feb
Propofol anesthesia induces phase synchronization changes in EEG.
2001 Feb
Evidence for significant differences in microsomal drug glucuronidation by canine and human liver and kidney.
2001 Feb
The differential effect of propofol on contractility of isolated myocardial trabeculae of rat and guinea-pig.
2001 Feb
Propofol depressed neutrophil hydrogen peroxide production more than midazolam, whereas adhesion molecule expression was minimally affected by both anesthetics in rats with abdominal sepsis.
2001 Feb
The use of esmolol as an alternative to remifentanil during desflurane anesthesia for fast-track outpatient gynecologic laparoscopic surgery.
2001 Feb
Hyperintense signal abnormality in subarachnoid spaces and basal cisterns on MR images of children anesthetized with propofol: new fluid-attenuated inversion recovery finding.
2001 Feb
Propofol action in both spinal cord and brain blunts electroencephalographic responses to noxious stimulation in goats.
2001 Feb 1
The effects of propofol on NMDA- or nitric oxide-mediated neurotoxicity in vitro.
2001 Feb 12
Chronic mu-opioid receptor stimulation in humans decreases muscle sympathetic nerve activity.
2001 Feb 13
[Hemodynamic effects of propofol induction administered with target controlled infusion pump in patients scheduled for open heart surgery].
2001 Feb 18
[Epileptoform EEG activity: occurrence under sevoflurane and not during propofol application].
2001 Jan
High concentration sevoflurane induction of anesthesia accelerates onset of vecuronium neuromuscular blockade.
2001 Jan
Remifentanil and controlled hypotension; comparison with nitroprusside or esmolol during tympanoplasty.
2001 Jan
Dystonic reaction after anesthesia.
2001 Jan
[The Baxter AS 50 syringe pump: a comparison with propofol-specific syringe pumps].
2001 Jan
[Marked bradycardia during anesthetic induction treated with temporary cardiac pacing in a patient with latent sick sinus syndrome].
2001 Jan
[The influence of age on hemodynamics and the dose requirements of propofol and buprenorphine in total intravenous anesthesia].
2001 Jan
[A case of hyperperfusion syndrome treated successfully by propofol].
2001 Jan
Propofol versus midazolam regarding their antioxidant activities.
2001 Jan
Does the use of propofol require a specialist anesthetist?
2001 Jan
Differential roles of iNOS and nNOS at rostral ventrolateral medulla during experimental endotoxemia in the rat.
2001 Jan
Spectral changes in systemic arterial pressure signals during acute mevinphos intoxication in the rat.
2001 Jan
Target-controlled infusion in sleep endoscopy.
2001 Jan
Prevention of postoperative nausea and vomiting with antiemetics in patients undergoing middle ear surgery: comparison of a small dose of propofol with droperidol or metoclopramide.
2001 Jan
Effect of dexmedetomidine, an alpha2-adrenoceptor agonist, on human pupillary reflexes during general anaesthesia.
2001 Jan
The immunomodulatory effects of prolonged intravenous infusion of propofol versus midazolam in critically ill surgical patients.
2001 Jan
Digitally assisted acromioplasty: the effect of interscalene block on this new surgical technique.
2001 Jan
Cerebrospinal fluid signal intensity increase on FLAIR MR images in patients under general anesthesia: the role of supplemental O2.
2001 Jan
Myopexy (Faden) results in more postoperative vomiting after strabismus surgery in children.
2001 Jan
Extracranial radiosurgery: immobilizing liver motion in dogs using high-frequency jet ventilation and total intravenous anesthesia.
2001 Jan 1
Long-term propofol infusion and cardiac failure in adult head-injured patients.
2001 Jan 13
Small doses of propofol, droperidol, and metoclopramide for the prevention of postoperative nausea and vomiting after thyroidectomy.
2001 Mar
Use of the Bispectral Index monitor to aid titration of propofol during a drug-assisted interview.
2001 Mar
Anaesthetic technique for transoesophageal echocardiography in children.
2001 Mar
Propofol is not effective for hyperventilation syndrome.
2001 Mar
The effect of the preemptive use of the NMDA receptor antagonist dextromethorphan on postoperative analgesic requirements.
2001 Mar
The determinants of propofol induction of anesthesia dose.
2001 Mar
Recovery profile and side effects of remifentanil-based anaesthesia with desflurane or propofol for laparoscopic cholecystectomy.
2001 Mar
Reduced isoflurane consumption with bispectral index monitoring.
2001 Mar
Patents

Sample Use Guides

In Vivo Use Guide
Adult Patients: Most adult patients under 55 years of age and classified as ASA-PS I or II require 2 to 2.5 mg/kg of DIPRIVAN ((propofol) Injectable Emulsion ) for induction when unpremedicated or when premedicated with oral benzodiazepines or intramuscular opioids. Elderly, Debilitated, or ASA-PS III or IV Patients: most of these patients require approximately 1 to 1.5 mg/kg (approximately 20 mg every 10 seconds) of DIPRIVAN Injectable Emulsion for induction of anesthesia according to their condition and responses. Pediatric Patients: Most patients aged 3 years through 16 years and classified ASA-PS I or II require 2.5 to 3.5 mg/kg of DIPRIVAN Injectable Emulsion for induction when unpremedicated or when lightly premedicated with oral benzodiazepines or intramuscular opioids
Route of Administration: Intravenous
In Vitro Use Guide
Propofol-induced cell (25, 50, and 100 µmol/L concentration of propofol) migration and invasion suppression are partially mediated by down-regulating H19 in MDA-MB-231 cells in vitro
Substance Class Chemical
Created
by admin
on Tue Oct 22 00:23:27 UTC 2019
Edited
by admin
on Tue Oct 22 00:23:27 UTC 2019
Record UNII
YI7VU623SF
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PROPOFOL
EP   GREEN BOOK   HSDB   INN   JAN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
INN   USAN  
Official Name English
PROPOFOL [USP-RS]
Common Name English
PROPOFOL [WHO-DD]
Common Name English
FRESOFOL
Brand Name English
PROPOFOL [HSDB]
Common Name English
DIPRIVAN
Brand Name English
ICI 35-868
Code English
PROPOFOL [MART.]
Common Name English
ICI35,868
Code English
NSC-5105
Code English
KETAFOL COMPONENT PROPOFOL
Brand Name English
ICI 35,868
Code English
PROPOFOL [ORANGE BOOK]
Common Name English
PROPOFOL [USP]
Common Name English
LIPURO
Brand Name English
PHENOL, 2,6-BIS(1-METHYLETHYL)
Common Name English
2,6-DIPROPAN-2-YLPHENOL
Systematic Name English
ICI-35868
Code English
PROPOFOL [EP]
Common Name English
PROPOFOL [MI]
Common Name English
PROPOFOL [JAN]
Common Name English
2,6-DIISOPROPYLPHENOL
Systematic Name English
PROPOFOL [INN]
Common Name English
PROPOFOL [VANDF]
Common Name English
PROPOFOL [USAN]
Common Name English
PROPOFOL [GREEN BOOK]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29756
Created by admin on Tue Oct 22 00:23:27 UTC 2019 , Edited by admin on Tue Oct 22 00:23:27 UTC 2019
CFR 21 CFR 522.2005
Created by admin on Tue Oct 22 00:23:27 UTC 2019 , Edited by admin on Tue Oct 22 00:23:27 UTC 2019
WHO-ATC N01AX10
Created by admin on Tue Oct 22 00:23:27 UTC 2019 , Edited by admin on Tue Oct 22 00:23:27 UTC 2019
NDF-RT N0000175681
Created by admin on Tue Oct 22 00:23:27 UTC 2019 , Edited by admin on Tue Oct 22 00:23:27 UTC 2019
NDF-RT N0000175975
Created by admin on Tue Oct 22 00:23:27 UTC 2019 , Edited by admin on Tue Oct 22 00:23:27 UTC 2019
WHO-VATC QN01AX10
Created by admin on Tue Oct 22 00:23:27 UTC 2019 , Edited by admin on Tue Oct 22 00:23:27 UTC 2019
LIVERTOX 808
Created by admin on Tue Oct 22 00:23:27 UTC 2019 , Edited by admin on Tue Oct 22 00:23:27 UTC 2019
WHO-ESSENTIAL MEDICINES LIST 1.1.2
Created by admin on Tue Oct 22 00:23:27 UTC 2019 , Edited by admin on Tue Oct 22 00:23:27 UTC 2019
Code System Code Type Description
MERCK INDEX
M9217
Created by admin on Tue Oct 22 00:23:27 UTC 2019 , Edited by admin on Tue Oct 22 00:23:27 UTC 2019
PRIMARY Merck Index
LactMed
2078-54-8
Created by admin on Tue Oct 22 00:23:27 UTC 2019 , Edited by admin on Tue Oct 22 00:23:27 UTC 2019
PRIMARY
INN
5073
Created by admin on Tue Oct 22 00:23:27 UTC 2019 , Edited by admin on Tue Oct 22 00:23:27 UTC 2019
PRIMARY
DRUG BANK
DB00818
Created by admin on Tue Oct 22 00:23:27 UTC 2019 , Edited by admin on Tue Oct 22 00:23:27 UTC 2019
PRIMARY
NCI_THESAURUS
C29384
Created by admin on Tue Oct 22 00:23:27 UTC 2019 , Edited by admin on Tue Oct 22 00:23:27 UTC 2019
PRIMARY
HSDB
2078-54-8
Created by admin on Tue Oct 22 00:23:27 UTC 2019 , Edited by admin on Tue Oct 22 00:23:27 UTC 2019
PRIMARY
EPA CompTox
2078-54-8
Created by admin on Tue Oct 22 00:23:27 UTC 2019 , Edited by admin on Tue Oct 22 00:23:27 UTC 2019
PRIMARY
PUBCHEM
4943
Created by admin on Tue Oct 22 00:23:27 UTC 2019 , Edited by admin on Tue Oct 22 00:23:27 UTC 2019
PRIMARY
MESH
D015742
Created by admin on Tue Oct 22 00:23:27 UTC 2019 , Edited by admin on Tue Oct 22 00:23:27 UTC 2019
PRIMARY
ChEMBL
CHEMBL526
Created by admin on Tue Oct 22 00:23:27 UTC 2019 , Edited by admin on Tue Oct 22 00:23:27 UTC 2019
PRIMARY
IUPHAR
5464
Created by admin on Tue Oct 22 00:23:27 UTC 2019 , Edited by admin on Tue Oct 22 00:23:27 UTC 2019
PRIMARY
CAS
2078-54-8
Created by admin on Tue Oct 22 00:23:27 UTC 2019 , Edited by admin on Tue Oct 22 00:23:27 UTC 2019
PRIMARY
EVMPD
SUB10116MIG
Created by admin on Tue Oct 22 00:23:27 UTC 2019 , Edited by admin on Tue Oct 22 00:23:27 UTC 2019
PRIMARY
RXCUI
8782
Created by admin on Tue Oct 22 00:23:27 UTC 2019 , Edited by admin on Tue Oct 22 00:23:27 UTC 2019
PRIMARY RxNorm
ECHA (EC/EINECS)
218-206-6
Created by admin on Tue Oct 22 00:23:27 UTC 2019 , Edited by admin on Tue Oct 22 00:23:27 UTC 2019
PRIMARY
WIKIPEDIA
PROPOFOL
Created by admin on Tue Oct 22 00:23:27 UTC 2019 , Edited by admin on Tue Oct 22 00:23:27 UTC 2019
PRIMARY
Related Record Type Details
METABOLIC ENZYME -> SUBSTRATE
BASIS OF STRENGTH->SUBSTANCE
ASSAY (HPLC)
EP
METABOLIC ENZYME -> SUBSTRATE
BASIS OF STRENGTH->SUBSTANCE
ASSAY (HPLC)
USP
Related Record Type Details
PRODRUG -> METABOLITE ACTIVE
Related Record Type Details
IMPURITY -> PARENT
For the calculation of contents, multiply the peak areas by 0.25
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
test 1
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (GC)
EP
IMPURITY -> PARENT
UNSPECIFIED
EP
IMPURITY -> PARENT
UNSPECIFIED
EP
IMPURITY -> PARENT
UNSPECIFIED
EP
IMPURITY -> PARENT
For the calculation of contents, multiply the peak areas by 5.0
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
test 2
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
UNSPECIFIED
EP
IMPURITY -> PARENT
Limit of propofol related compound A?[note?This test is to be performed in conjunction with Related compounds Test 1. ]
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
test 2
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
Limit of propofol related compound B
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
UNSPECIFIED
EP
IMPURITY -> PARENT
UNSPECIFIED
EP
IMPURITY -> PARENT
UNSPECIFIED
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (GC)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (GC)
EP
IMPURITY -> PARENT
UNSPECIFIED
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (GC)
EP
IMPURITY -> PARENT
UNSPECIFIED
EP
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life Elimination
PHARMACOKINETIC
Elimination
PHARMACOKINETIC
Elimination
PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC After a 10-day infusion
PHARMACOKINETIC