Propanidid

Propanidid
Clinical data
Trade names	Epontol
AHFS/Drugs.com	International Drug Names
ATC code	N01AX04 (WHO) ;
Legal status
Legal status	BR: Class C1 (Other controlled substances);
Identifiers
	IUPAC name Propyl {4-[2-(diethylamino)-2-oxoethoxy]-3-methoxyphenyl}acetate;
CAS Number	1421-14-3 ;
PubChem CID	15004;
DrugBank	DB13234 ;
ChemSpider	14283 ;
UNII	AO82L471NS;
KEGG	D05626 ;
ChEBI	CHEBI:135432;
ChEMBL	ChEMBL2105345;
CompTox Dashboard (EPA)	DTXSID7048825 ;
ECHA InfoCard	100.014.384
Chemical and physical data
Formula	C18H27NO5
Molar mass	337.416 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C(OCCC)Cc1cc(OC)c(OCC(=O)N(CC)CC)cc1;
	InChI InChI=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 ; Key:KEJXLQUPYHWCNM-UHFFFAOYSA-N ;
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Propanidid is an ultra short-acting phenylacetate general anesthetic. It was originally introduced by Bayer in 1963^[2] but anaphylactic reactions caused it to be withdrawn shortly afterwards.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.^[3] 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.

^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
^ US patent 3086978, Hiltmann R, Wollweber H, Hoffmeister F, Wirth W, "3-Methoxy-4-Carbamidomethoxy-Phenylacetic Acid Esters", issued 1963-04-23, assigned to Bayer
^ Clarke RS, Dundee JW, Carson IW (October 1973). "Proceedings: A new steroid anaesthetic-althesin". Proceedings of the Royal Society of Medicine. 66 (10): 1027–1030. doi:10.1177/003591577306601023. PMC 1645602. PMID 4148526.

[1] Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.

[2] US patent 3086978, Hiltmann R, Wollweber H, Hoffmeister F, Wirth W, "3-Methoxy-4-Carbamidomethoxy-Phenylacetic Acid Esters", issued 1963-04-23, assigned to Bayer

[3] Clarke RS, Dundee JW, Carson IW (October 1973). "Proceedings: A new steroid anaesthetic-althesin". Proceedings of the Royal Society of Medicine. 66 (10): 1027–1030. doi:10.1177/003591577306601023. PMC 1645602. PMID 4148526.

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