R-4066 - Misplaced Pages

(Redirected from Spirodone) Chemical compound

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Pharmaceutical compound

R-4066
Clinical data

Other names	N-(3,3-diphenyl-4-oxohex-1-yl)-7,8-benzo-3-azaspiroundecane
Identifiers
IUPAC name 6-{3,4-dihydro-2H-spiro-1'-yl}-4,4-diphenylhexan-3-one
CAS Number	66194-36-3 oxalate: 101564-56-1
PubChem CID	380029
ChemSpider	336763
UNII	L4YPY81SBM oxalate: DL9M9L165Z
ChEMBL	ChEMBL2010535
CompTox Dashboard (EPA)	DTXSID101018281 DTXSID10906347, DTXSID101018281
Chemical and physical data
Formula	C₃₂H₃₇NO
Molar mass	451.654 g·mol
3D model (JSmol)	Interactive image
SMILES CCC(=O)C(CCN1CCC2(CCCC3=CC=CC=C32)CC1)(C4=CC=CC=C4)C5=CC=CC=C5
InChI InChI=1S/C32H37NO/c1-2-30(34)32(27-14-5-3-6-15-27,28-16-7-4-8-17-28)22-25-33-23-20-31(21-24-33)19-11-13-26-12-9-10-18-29(26)31/h3-10,12,14-18H,2,11,13,19-25H2,1H3 Key:ZVFXEHSJPKPKDW-UHFFFAOYSA-N
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R-4066 (Spirodone) is a drug which is an derivative of the opioid analgesic norpipanone, wherein the piperidine ring has been replaced by a tricyclic spiro heterocycle. Developed by Janssen Pharmaceutica, it is around 212× more potent than methadone as an analgesic in animal tests, with an effective oral dosage of 0.07 mg/kg, but is shorter acting, with a duration of action of around 3 hours. If the ketone function is reduced and acetylated, the racemate has a potency of 106× that of methadone and has an analgesic duration of 20.5 hours compared to 8 hours for methadone.

R-4066 has not been researched in humans, but would be expected to produce effects similar to those of fentanyl, including strong analgesia, sedation, euphoria, constipation, itching and respiratory depression which could be harmful or fatal.

References

U.S. patent 3,125,580
Frincke JM, Henderson GL (May 1978). "Synthesis and analgesic activity of some long-acting piperidinospiro derivatives of methadone". Journal of Medicinal Chemistry. 21 (5): 474–6. doi:10.1021/jm00203a014. PMID 660594.