Ciramadol

Ciramadol
Clinical data
Other names	Ciramadol, WY-15705
Routes of; administration	Oral
ATC code	none;
Identifiers
	IUPAC name 3-{(R)-Dimethylamino-[(1R,2R)-2-hydroxycyclohexyl]}methyl]phenol;
CAS Number	63269-31-8 ;
PubChem CID	44463;
ChemSpider	40461 ;
UNII	9NQ109OW0G;
KEGG	D03523 ;
ChEMBL	ChEMBL2104132;
CompTox Dashboard (EPA)	DTXSID601018412 ;
Chemical and physical data
Formula	C15H23NO2
Molar mass	249.349 g/mol g·mol−1
3D model (JSmol)	Interactive image;
	SMILES OC1=CC=CC([C@@H]([C@H]2CCCC[C@H]2O)N(C)C)=C1;
	InChI InChI=1S/C15H23NO2/c1-16(2)15(11-6-5-7-12(17)10-11)13-8-3-4-9-14(13)18/h5-7,10,13-15,17-18H,3-4,8-9H2,1-2H3/t13-,14+,15-/m0/s1 ; Key:UVTLONZTPXCUPU-ZNMIVQPWSA-N ;
	(verify)

Ciramadol (WY-15,705) is an opioid analgesic that was developed in the late 1970s^[1] and is related to phencyclidine, tramadol, tapentadol and venlafaxine.^[2] It is a mixed agonist-antagonist for the μ-opioid receptor with relatively low abuse potential^[3] and a ceiling on respiratory depression^[4] which makes it a relatively safe drug. It has a slightly higher potency and effectiveness as an analgesic than codeine,^[5] but is weaker than morphine.^[6] Other side effects include sedation and nausea but these are generally less severe than with other similar drugs.^[7]

References

^ US Patent 3928626 - Benzylamine Analgesics
^ Cochrane AD, Bell R, Sullivan JR, Shaw J. Ciramadol. A new analgesic. Medical Journal of Australia. 1979 Nov 3;2(9):501-2.
^ Preston KL, Bigelow GE, Liebson IA. Comparative evaluation of morphine, pentazocine and ciramadol in postaddicts. Journal of Pharmacology and Experimental Therapeutics. 1987 Mar;240(3):900-10.
^ Romagnoli A, Keats AS. Low ceiling respiratory depression by ciramadol. International Journal of Clinical Pharmacology Research. 1986;6(6):451-5.
^ Downing JW, Brock-Utne JG, Holloway AM. Ciramadol - a new synthetic analgesic. A double-blind comparison with oral codeine for postoperative pain relief. South African Medical Journal. 1983 Dec 10;64(25):978-82.
^ Powell WF. A double-blind comparison of multiple intramuscular doses of ciramadol, morphine, and placebo for the treatment of postoperative pain. Anesthesia and Analgesia. 1985 Nov;64(11):1101-7.
^ Stambaugh JE Jr, McAdams J. Comparison of the analgesic efficacy and safety oral ciramadol, codeine, and placebo in patients with chronic cancer pain. Journal of Clinical Pharmacology. 1987 Feb;27(2):162-6.

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