Propanidid

Propanidid

Systematic (IUPAC) name
propyl {4-[2-(diethylamino)-2-oxoethoxy]-3-methoxyphenyl}acetate
Clinical data
AHFS/Drugs.com	International Drug Names
Identifiers
CAS Number	1421-14-3 N
ATC code	N01AX04 (WHO)
PubChem	CID: 15004
ChemSpider	14283 Y
UNII	AO82L471NS Y
KEGG	D05626 Y
Chemical data
Formula	C18H27NO5
Molecular mass	337.411 g/mol
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 Y Key:KEJXLQUPYHWCNM-UHFFFAOYSA-N Y
NY (what is this?)  (verify)

Propanidid is an ultra short-acting phenylacetate general anesthetic. It was originally introduced by Bayer in 1963 but anaphylactic reactions caused it to be withdrawn shortly afterwards.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 or not 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. Several cases of negative reactions have been recorded for different drugs using Cremophor EL as solubilizer. This suggest that the negative reactions were mainly caused by Cremophor and not by the drug substances themselves.

Synthesis

Propanidid synthesis: R. Hiltmann et al., DE 1134981 ; U.S. Patent 3,086,978 (1962, 1963 both to Bayer).