Ketobemidone

Ketobemidone
Clinical data
Trade names	Ketogan
Other names	Ketobemidone, Cliradon, Cymidon, Ketogan, Ketorax
AHFS/Drugs.com	International Drug Names
Routes of; administration	By mouth, rectal, intravenous
ATC code	N02AB01 (WHO) ;
Legal status
Legal status	AU: S9 (Prohibited substance); BR: Class F1 (Prohibited narcotics); CA: Schedule I; DE: Anlage II (Authorized trade only, not prescriptible); US: Schedule I; EU: Rx-only;
Pharmacokinetic data
Bioavailability	34~40% (oral), 44% (rectal)
Elimination half-life	2–4 hours
Duration of action	3–5 hours
Identifiers
	IUPAC name 1-[4-(3-Hydroxyphenyl)-1-methyl-4-piperidyl]propan-1-one;
CAS Number	469-79-4 ;
PubChem CID	10101;
DrugBank	DB06738 ;
ChemSpider	9697 ;
UNII	PQS1L514CF;
KEGG	D08100 ;
ChEMBL	ChEMBL47072 ;
CompTox Dashboard (EPA)	DTXSID00196977 ;
ECHA InfoCard	100.006.748
Chemical and physical data
Formula	C15H21NO2
Molar mass	247.338 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C(CC)C1(CCN(C)CC1)c2cc(O)ccc2;
	InChI InChI=1S/C15H21NO2/c1-3-14(18)15(7-9-16(2)10-8-15)12-5-4-6-13(17)11-12/h4-6,11,17H,3,7-10H2,1-2H3 ; Key:ALFGKMXHOUSVAD-UHFFFAOYSA-N ;
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Ketobemidone, sold under the brand name Ketogan among others, is a powerful synthetic opioid painkiller. Its effectiveness against pain is in the same range as morphine, and it also has some NMDA-antagonist properties imparted, in part, by its metabolite norketobemidone.^[2] This may make it useful for some types of pain that do not respond well to other opioids.^[2] It is marketed in Denmark, Iceland, Norway. Until 2024 it was availble in, but is now withdrawn in Sweden. It is used for severe pain.^[3]

^ https://www.ema.europa.eu/documents/psusa/ketobemidone-list-nationally-authorised-medicinal-products-psusa/0001807/202005_en.pdf ^{[bare URL PDF]}
^ ^a ^b Ebert B, Thorkildsen C, Andersen S, Christrup LL, Hjeds H (September 1998). "Opioid analgesics as noncompetitive N-methyl-D-aspartate (NMDA) antagonists". Biochemical Pharmacology. 56 (5): 553–9. doi:10.1016/S0006-2952(98)00088-4. PMID 9783723.
^ Brayfield A, ed. (9 January 2017). "Ketobemidone Hydrochloride: Martindale: The Complete Drug Reference". MedicinesComplete. London, UK: Pharmaceutical Press. Retrieved 6 September 2017.

[1] ttps://www.ema.europa.eu/documents/psusa/ketobemidone-list-nationally-authorised-medicinal-products-psusa/0001807/202005_en.pdf ^{[bare URL PDF]}

[NMDA98-2] Ebert B, Thorkildsen C, Andersen S, Christrup LL, Hjeds H (September 1998). "Opioid analgesics as noncompetitive N-methyl-D-aspartate (NMDA) antagonists". Biochemical Pharmacology. 56 (5): 553–9. doi:10.1016/S0006-2952(98)00088-4. PMID 9783723.

[3] Brayfield A, ed. (9 January 2017). "Ketobemidone Hydrochloride: Martindale: The Complete Drug Reference". MedicinesComplete. London, UK: Pharmaceutical Press. Retrieved 6 September 2017.

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