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
ATC code	N01AX04 (WHO)
PubChem	CID 15004
ChemSpider	14283
UNII	AO82L471NS
KEGG	D05626
Chemical data
Formula	C18H27NO5
Molar 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 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 It was originally introduced by Bayer in 1963^[1] but anaphylactic reactions caused it to be withdrawn shortly afterwards.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. Clarke, R. S.; Dundee, J. W.; Carson, I. W. (1973). "A New Steroid Anaesthetic - Althesin" (pdf). Proceedings of the Royal Society of Medicine 66 (10): 1027–1030. PMC 1645602. PMID 4148526.

External links

• Klockgether-Radke A, Kersten J, Schröder T, Stafforst D, Kettler D, Hellige G (1995). "Anesthesia with propanidid in a liposomal preparation. An experimental study in swine". Anaesthesist 44 (8): 573–80. doi:10.1007/s001010050191. PMID 7573906.
• Habazettl H, Vollmar B, Röhrich F, Conzen P, Doenicke A, Baethmann A (1992). "Anesthesiologic efficacy of propanidid as a liposome dispersion. An experimental study with rats". Anaesthesist 41 (8): 448–56. PMID 1524155.
• Zawisza P, Przyborowski L (1992). "Propanidid and etomidate identification from the blood by thin-layer chromatography". Acta Pol Pharm 49 (5–6): 15–7. PMID 16092193.
• Theis JG, et al. (1995). "Anaphylactoid reactions in children receiving high-dose intravenous cyclosporine for reversal of tumor resistance: the causative role of improper dissolution of Cremophor EL". Journal of Clinical Oncology 13 (10): 2508–2516. PMID 7595701.
• Ebo DG, et al. (2001). "IgE-mediated anaphylaxis after first intravenous infusion of cyclosporine". Annals of Allergy, Asthma & Immunology 87 (3): 243–245. doi:10.1016/S1081-1206(10)62234-X. PMID 11570623.