Editing Propofol (section)

{{Short description|Intravenous medication used in anesthesia}}
{{Distinguish|Propanol}}
{{Use dmy dates|date=December 2024}}
{{cs1 config |name-list-style=vanc |display-authors=6}}
{{Infobox drug
| Watchedfields = changed
| verifiedrevid = 456484691
| image = Propofol.svg
| image_class = skin-invert-image
| alt = 
| image2 = Propofol ball-and-stick model from xtal 2014.png
| alt2 = Ball-and-stick model of propofol
| caption = <!-- Clinical data -->
| pronounce = 
| tradename = Diprivan, others<ref>{{Cite web |title=Propofol |url=https://www.drugs.com/international/propofol.html |access-date=2 January 2019 |website=Drugs.com}}</ref>
| Drugs.com = {{drugs.com|monograph|Propofol}}
| MedlinePlus = 
| DailyMedID = Propofol
| pregnancy_AU = C
| pregnancy_AU_comment = 
| pregnancy_category = 
| addiction_liability = Moderate<ref name="What the ΔFosB?">{{cite journal | vauthors = Ruffle JK | title = Molecular neurobiology of addiction: what's all the (Δ)FosB about? | journal = The American Journal of Drug and Alcohol Abuse | volume = 40 | issue = 6 | pages = 428–437 | date = November 2014 | pmid = 25083822 | doi = 10.3109/00952990.2014.933840 | quote = Propofol is a general anesthetic, however its abuse for recreational purpose has been documented (120). Using control drugs implicated in both ΔFosB induction and addiction (ethanol and nicotine), similar ΔFosB expression was apparent when propofol was given to rats. Moreover, this cascade was shown to act via the dopamine D1 receptor in the NAc, suggesting that propofol has abuse potential (119) }}</ref>
| dependency_liability = [[Physical dependence|Physical]]: Very high <!-- {{cite journal | vauthors = Cawley MJ, Guse TM, Laroia A, Haith LR, Ackerman BH | title = Propofol withdrawal syndrome in an adult patient with thermal injury | journal = Pharmacotherapy | volume = 23 | issue = 7 | pages = 933–939 | date = July 2003 | pmid = 12885106 | doi = 10.1592/phco.23.7.933.32728 }} --><br />[[Psychological dependence|Psychological]]:  no data
| routes_of_administration = [[Intravenous therapy|Intravenous]]
| class = [[GABA receptor agonist|GABA<sub>A</sub> receptor agonist]];<br>[[sedative]];<br>[[general anesthetic]]
| ATC_prefix = N01
| ATC_suffix = AX10
| ATC_supplemental = <!-- Legal status -->
| legal_AU = S4
| legal_AU_comment = 
| legal_BR = C1
| legal_BR_comment = <ref>{{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=31 March 2023 |title=RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |url-status=live |archive-url=https://web.archive.org/web/20230803143925/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |archive-date=3 August 2023 |access-date=16 August 2023 |publisher=[[Diário Oficial da União]] |language=pt-BR |publication-date=4 April 2023}}</ref>
| legal_CA = Rx-only
| legal_CA_comment = 
| legal_DE = <!-- Anlage I, II, III or Unscheduled -->
| legal_DE_comment = 
| legal_NZ = <!-- Class A, B, C -->
| legal_NZ_comment = 
| legal_UK = POM
| legal_UK_comment = 
| legal_US = Rx-only
| legal_US_comment = <ref name="Diprivan FDA label">{{Cite web |title=Diprivan- propofol injection, emulsion |url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=5cec3b97-5183-4a9d-accd-21e76c99d3dd |access-date=17 April 2021 |website=DailyMed}}</ref>
| legal_EU = 
| legal_EU_comment = 
| legal_UN = <!-- N I, II, III, IV / P I, II, III, IV -->
| legal_UN_comment = 
| legal_status = Rx-only

<!-- Pharmacokinetic data -->| bioavailability = NA
| protein_bound = 95–99%
| metabolism = [[Liver]] [[glucuronidation]]
| metabolites = 
| onset = 15–30 seconds<ref name="AHFS2016">{{Cite web |title=Propofol |url=https://www.drugs.com/monograph/Propofol.html |url-status=live |archive-url=https://web.archive.org/web/20161009184353/https://www.drugs.com/monograph/propofol.html |archive-date=9 October 2016 |access-date=21 January 2017 |publisher=The American Society of Health-System Pharmacists}}</ref>
| elimination_half-life = 1.5–31 hours<ref name=AHFS2016/>
| duration_of_action = ~5–10 minutes<ref name=AHFS2016/>
| excretion = [[Liver]]

<!-- Identifiers -->| CAS_number_Ref = {{cascite|correct|CAS}}
| CAS_number = 2078-54-8
| CAS_supplemental = 
| PubChem = 4943
| IUPHAR_ligand = 5464
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB00818
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 4774
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = YI7VU623SF
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D00549
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 44915
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 526
| NIAID_ChemDB = 
| PDB_ligand = 
| synonyms = <!-- Chemical and physical data -->
| IUPAC_name = 2,6-Diisopropylphenol <br /> 2,6-bis(propan-2-yl)phenol
| C = 12
| H = 18
| O = 1
| SMILES = CC(C)c1cccc(c1O)C(C)C
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C12H18O/c1-8(2)10-6-5-7-11(9(3)4)12(10)13/h5-9,13H,1-4H3
| StdInChI_comment = 
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = OLBCVFGFOZPWHH-UHFFFAOYSA-N
| density = 
| density_notes = 
| melting_point = 
| melting_high = 
| melting_notes = 
| boiling_point = 
| boiling_notes = 
| solubility = ΔG<sub>solv</sub><sup>H<sub>2</sub>O</sup> = -4.39
| sol_units = [[kcal/mol]]<ref name="Arcario Mayne Tajkhorshid pp. 12075–12086">{{cite journal | vauthors = Arcario MJ, Mayne CG, Tajkhorshid E | title = Atomistic models of general anesthetics for use in in silico biological studies | journal = The Journal of Physical Chemistry B | volume = 118 | issue = 42 | pages = 12075–12086 | date = October 2014 | pmid = 25303275 | pmc = 4207551 | doi = 10.1021/jp502716m | publisher = American Chemical Society (ACS) }}</ref>
| specific_rotation = 
}}

<!-- Definition and medical uses -->
'''Propofol'''<ref>{{Cite web | work = PubChem |title=Propofol |url=https://pubchem.ncbi.nlm.nih.gov/compound/4943 |access-date=25 October 2023 | publisher = U.S. National Library of Medicine }}</ref> is the active component of an intravenous [[anesthetic]] formulation used for induction and maintenance of [[general anesthesia]]. It is chemically termed 2,6-diisopropylphenol.  The formulation was approved under the brand name '''Diprivan.''' Numerous generic versions have since been released. [[Intravenous therapy|Intravenous]] administration is used to induce [[unconsciousness]] after which anesthesia may be maintained using a combination of medications. It is manufactured as part of a sterile injectable [[emulsion]] formulation using soybean oil and [[lecithin]], giving it a white milky coloration.<ref>{{Cite web |title=Making Stable, Sterile Propofol |url=https://www.microfluidics-mpt.com/blog/making-stable-sterile-propofol |access-date=25 October 2023 |website=www.microfluidics-mpt.com }}</ref>

Recovery from propofol-induced anesthesia is generally rapid and associated with less frequent side effects<ref>{{Cite web |title=Propofol |url=https://go.drugbank.com/drugs/DB00818 |access-date=25 October 2023 |website=go.drugbank.com }}</ref><ref>{{cite journal | vauthors = Glen JB | title = The Discovery and Development of Propofol Anesthesia: The 2018 Lasker-DeBakey Clinical Medical Research Award | journal = JAMA | volume = 320 | issue = 12 | pages = 1235–1236 | date = September 2018 | pmid = 30208399 | doi = 10.1001/jama.2018.12756 }}</ref> (e.g., drowsiness, nausea, vomiting) compared to other anesthetic agents. Propofol may be used prior to [[diagnostic procedures]] requiring anesthesia, in the management of refractory [[status epilepticus]], and for induction or maintenance of anesthesia prior to and during [[surgeries]]. It may be administered as a [[Bolus (medicine)|bolus]] or an [[Infusion therapy|infusion]], or some combination of the two.

First synthesized in 1973, by [[John B. Glen]], a British veterinary [[anesthesiologist]] working for [[Imperial Chemical Industries]] (ICI, later [[AstraZeneca]]),<ref>{{cite journal | vauthors = Glen JB |title=Try, try, and try again: personal reflections on the development of propofol |journal=British Journal of Anaesthesia |date=July 2019 |volume=123 |issue=1 |pages=3–9 |doi=10.1016/j.bja.2019.02.031 |pmid=30982566 |doi-access=free }}</ref> in 1986 propofol was introduced for therapeutic use as a lipid emulsion in the United Kingdom and New Zealand. Propofol (Diprivan) received [[FDA approval]] in October 1989. It is on the [[WHO Model List of Essential Medicines|World Health Organization's List of Essential Medicines]].<ref name="WHO22nd">{{Cite book |title=World Health Organization model list of essential medicines: 22nd list (2021) |vauthors=((World Health Organization)) |publisher=World Health Organization |year=2021 |location=Geneva |hdl=10665/345533 |id=WHO/MHP/HPS/EML/2021.02 |author-link=World Health Organization |hdl-access=free}}</ref>