Propanidid

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Propanidid
Propanidid-2D-skeletal.png
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 YesY
UNII AO82L471NS YesY
KEGG D05626 YesY
Chemical data
Formula C18H27NO5
Molecular mass 337.411 g/mol
  • O=C(OCCC)Cc1cc(OC)c(OCC(=O)N(CC)CC)cc1
  • 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 YesY
  • Key:KEJXLQUPYHWCNM-UHFFFAOYSA-N YesY
 NYesY (what is this?)  (verify)

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 It was originally introduced by Bayer in 1963[1] but anaphylactic reactions caused it to be withdrawn shortly afterwards.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

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External links

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  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. ↑ Lua error in package.lua at line 80: module 'strict' not found.
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