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Propanidid

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Propanidid

Propanidid
Systematic (IUPAC) name
propyl {4-[2-(diethylamino)-2-oxoethoxy]-3-methoxyphenyl}acetate
Clinical data
AHFS/Drugs.com
Identifiers
CAS Registry Number  N
ATC code N01
PubChem CID:
ChemSpider  YesY
UNII  YesY
KEGG  YesY
Chemical data
Formula C18H27NO5
Molecular mass 337.411 g/mol
 N   

Propanidid is an ultra short-acting phenylacetate general anesthetic. It was originally introduced by Bayer in 1963[1] but anaphylactic reactions caused it to be withdrawn shortly afterwards.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.[2] 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).

References

  1. ^ 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 
  2. ^

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