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Ciramadol


Ciramadol
Systematic (IUPAC) name
3-[(R)-dimethylamino-[(1R,2R)-2-hydroxycyclohexyl]methyl]phenol
Identifiers
CAS number	63269-31-8
ATC code	?
PubChem	44463
Chemical data
Formula	C₁₅H₂₃N O₂
Mol. mass	249.349 g/mol
Synonyms	Ciramadol, WY-15705
Pharmacokinetic data
Bioavailability	?
Metabolism	?
Half life	?
Excretion	?
Therapeutic considerations
Pregnancy cat.	?
Legal status
Routes	?

Ciramadol (WY-15705) is an opioid analgesic that was developed in the late 1970s.^[1]

Additional recommended knowledge

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Daily Sensitivity Test

Ciramadol is a mixed agonist-antagonist for mu opioid receptors with relatively low abuse potential^[2] and a ceiling on respiratory depression^[3] which makes it a relatively safe drug. It has a slightly higher potency and effectiveness as an analgesic than codeine,^[4] but is weaker than morphine.^[5] Other side effects include sedation and nausea but these are generally less severe than with other similar drugs.^[6]

References

^ 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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Opioids

Opiate derivatives

6-Methyldihydromorphine • 6-Methylenedihydrodesoxymorphine • 14-Methoxymetopon • Acetylcodeine • Acetyldihydrocodeine • Acetyldihydrocodeinone • Acetylmorphone • Benzylmorphine • β-4-morpholinylethylmorphine • Codeine • Codeine-N-Oxide • Codeinone • Codoxime • Desomorphine • Diacetyldihydromorphine • Dihydrocodeine • Dihydrocodeinone enol acetate • Dihydrohydroxycodeinone • Dihydrodesoxymorphine • Dihydroheroin • Dihydroisocodeine • Dihydromorphine • Dipropanoylmorphine • Ethylmorphine • Heroin (Diamorphine) • Heterocodeine • Hydrocodone • Hydromorphinol • Hydromorphone • Laudanum • Methyldesorphine • Methyldihydromorphine • Methylnaltrexone • Metopon • Monoacetylmorphine • Morphine-N-Oxide • Morphine • Morphinone • Morphine-6-glucuronide • Myrophine • Nalbuphine • Nalmefene • Nalorphine • Naloxone • Naltrexone • Naltrindole • Nicocodeine • Nicodicodeine • Nicomorphine • Norcodeine • Normorphine • Omnopon • Opium • Oripavine • Oxycodone • Oxymorphone • Pantopon • Papaveretum • Paregoric • Pholcodeine • Pseudomorphine • Poppy Straw • Poppy Tea • Semorphone • Tetrapon • Thebacon • Thebaine

Morphinans

Butorphanol • Cyclorphan • Dextro-3-hydroxy-N-allylmorphinan • Dextrorphan • Drotebanol • Levargorphan • Levallorphan • Levorphanol • Levorphan • Levophenacylmorphan • Levomethorphan • Norlevorphanol • Oxilorphan • Phenomorphan • Racemethorphan • Racemorphan

Benzomorphans

Bremazocine • Cyclazocine • Dezocine • Ethylketocyclazocine • Ketazocine • Metazocine • Pentazocine • Phenazocine

4-Phenylpiperidines

Pethidines (Meperidines)	Anileridine • Benzethidine • Carperidine • Difenoxin • Diphenoxylate • Etoxeridine (Carbetidine) • Furethidine • Hydroxypethidine (Bemidone) • Morpheridine • Oxpheneridine (Carbamethidine) • Pethidine (Meperidine) • Pethidine Intermediate A • Pethidine Intermediate B (Norpethidine) • Pethidine Intermediate C (Pethidinic Acid) • Pheneridine • Phenoperidine • Piminodine • Properidine (Ipropethidine) • Sameridine • WIN-7681
Prodines	Allylprodine • α-meprodine • α-prodine • β-meprodine • β-prodine • Meprodine • MPPP • PEPAP • Prodine • Prosidol • Trimeperidine
Ketobemidones	Acetoxyketobemidone • Ketobemidone • Methylketobemidone • Propylketobemidone
Others	Alvimopan • Loperamide • Picenadol

Open Chain Opioids

Amidones	Dextromethadone • Dipipanone • Isomethadone • Levomethadone • Methadone • Methadone Intermediate • Norpipanone • Phenadoxone (Heptazone) • Pipidone
Methadols	Acetylmethadol • α-methadol • α-acetylmethadol • β-methadol • β-acetylmethadol • Dimepheptanol • Levo-α-acetylmethadol • Noracymethadol
Moramides	Dextromoramide • Levomoramide • Moramide Intermediate • Racemoramide
Thiambutenes	Diethylthiambutene • Dimethylthiambutene • Ethylmethylthiambutene
Phenalkoxams	Dextropropoxyphene • Dimenoxadol • Dioxaphetyl Butyrate • Levopropoxyphene • Propoxyphene
Ampromides	Diampromide • Phenampromide • Propiram
Others	Lefetamine