Propanidid

{{Short description|Chemical compound}}

{{Drugbox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 464216117

| IUPAC_name = Propyl {4-[2-(diethylamino)-2-oxoethoxy]-3-methoxyphenyl}acetate

| image = Propanidid.svg

| image_class = skin-invert-image

| width = 200

| tradename = Epontol

| Drugs.com = {{drugs.com|international|propanidid}}

| pregnancy_category =

| legal_AU =

| legal_BR = C1

| legal_BR_comment = {{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-03-31 |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=2023-08-03 |access-date=2023-08-16 |publisher=Diário Oficial da União |language=pt-BR |publication-date=2023-04-04}}

| legal_CA =

| legal_DE =

| legal_NZ =

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| routes_of_administration =

| bioavailability =

| metabolism =

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| CAS_number_Ref = {{cascite|correct|CAS}}

| CAS_number = 1421-14-3

| ATC_prefix = N01

| ATC_suffix = AX04

| PubChem = 15004

| DrugBank_Ref = {{drugbankcite|changed|drugbank}}

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 14283

| ChEMBL = 2105345

| ChEBI = 135432

| DrugBank = DB13234

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = AO82L471NS

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D05626

| C=18 | H=27 | N=1 | O=5

| smiles = O=C(OCCC)Cc1cc(OC)c(OCC(=O)N(CC)CC)cc1

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C18H27NO5/c1-5-10-23-18(21)12-14-8-9-15(16(11-14)22-4)24-13-17(20)19(6-2)7-3/h8-9,11H,5-7,10,12-13H2,1-4H3

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = KEJXLQUPYHWCNM-UHFFFAOYSA-N

}}

Propanidid is an ultra short-acting phenylacetate general anesthetic. It was originally introduced by Bayer in 1963{{ cite patent | country = US | status = patent | number = 3086978 | inventor = Hiltmann R, Wollweber H, Hoffmeister F, Wirth W | title = 3-Methoxy-4-Carbamidomethoxy-Phenylacetic Acid Esters | gdate = 1963-04-23 | assign1 = Bayer }} but anaphylactic reactions caused it to be withdrawn shortly afterwards.

Even though Cremophor EL has been shown to cause anaphylactic reactions in humans in several cases (both when given intravenously and orally), it is still debated whether propanidid itself may have contributed to the reactions.

It has been argued that the toxic effects or reactions to propanidid (and Althesin) were due to the drugs themselves.{{cite journal | vauthors = Clarke RS, Dundee JW, Carson IW | title = Proceedings: A new steroid anaesthetic-althesin | journal = Proceedings of the Royal Society of Medicine | volume = 66 | issue = 10 | pages = 1027–1030 | date = October 1973 | pmid = 4148526 | pmc = 1645602 | doi = 10.1177/003591577306601023 }} Several cases of negative reactions have been recorded for different drugs using Cremophor EL as solubilizer, suggesting that the negative reactions were mainly caused by Cremophor and not by the drug substances themselves.