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Propanidid

From Wikipedia, the free encyclopedia
(Redirected from C18H27NO5)

Propanidid
Clinical data
Trade namesEpontol
AHFS/Drugs.comInternational Drug Names
ATC code
Legal status
Legal status
Identifiers
  • Propyl {4-[2-(diethylamino)-2-oxoethoxy]-3-methoxyphenyl}acetate
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.014.384 Edit this at Wikidata
Chemical and physical data
FormulaC18H27NO5
Molar mass337.416 g·mol−1
3D model (JSmol)
  • 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 checkY
  • Key:KEJXLQUPYHWCNM-UHFFFAOYSA-N checkY
 X markNcheckY (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 It was originally introduced by Bayer in 1963 but anaphylactic reactions caused it to be withdrawn shortly afterwards.[2][3]

The cause of the anaphylaxis has not been determined. Similar to Althesin, Cremophor EL was used as part of the formulation for propanidid.[4] Cremephor EL has been shown to cause anaphylactic reactions in humans in several cases (both when given intravenously and orally), and several negative reactions have been recorded for drugs using Cremephor EL.[5] However, some have argued that the anaphylaxis was a reaction to propanidid itself.[6][7]

References

[edit]
  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. Fisher MM, Baldo BA (1993-01-01). "The incidence and clinical features of anaphylactic reactions during anesthesia in Australia". Annales Francaises d'Anesthesie et de Reanimation. Actualités en Allergo-Anesthésie New Trends in Anaphylactoid Risk in Anaesthesia. 12 (2): 97–104. doi:10.1016/S0750-7658(05)81016-0. PMID 8368592.
  4. MacPherson RD (2001). "Pharmaceutics for the anaesthetist". Anaesthesia. 56 (10): 965–979. doi:10.1111/j.1365-2044.2001.02216.x. ISSN 0003-2409. PMID 11576099.
  5. Irizarry LD, Luu TH, McKoy JM, Samaras AT, Fisher MJ, Carias EE, et al. (March 2009). "Cremophor EL-containing paclitaxel-induced anaphylaxis: a call to action". Community Oncology. 6 (3): 132–134. doi:10.1016/S1548-5315(11)70224-8. PMC 9838553. PMID 36643961.
  6. 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.
  7. Christmas D (May 1984). "Immune reaction to propanidid". Anaesthesia. 39 (5): 470–473. doi:10.1111/j.1365-2044.1984.tb07318.x. PMID 6731777.