ciramadol

{{Short description|Opioid analgesic drug}}

{{Distinguish|Cimaterol}}

{{Drugbox

| Watchedfields = changed

| verifiedrevid = 451180085

| IUPAC_name = 3-{(R)-Dimethylamino-[(1R,2R)-2-hydroxycyclohexyl]}methyl]phenol

| image = Ciramadol.svg

| image_class = skin-invert-image

| tradename =

| pregnancy_category =

| legal_status =

| routes_of_administration = Oral

| bioavailability =

| protein_bound =

| metabolism =

| elimination_half-life =

| excretion =

| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 63269-31-8

| ATC_prefix = none

| ATC_suffix =

| PubChem = 44463

| ChEMBL = 2104132

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank =

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 40461

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 9NQ109OW0G

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D03523

| C=15 | H=23 | N=1 | O=2

| smiles = OC1=CC=CC([C@@H]([C@H]2CCCC[C@H]2O)N(C)C)=C1

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = UVTLONZTPXCUPU-ZNMIVQPWSA-N

| synonyms = Ciramadol, WY-15705

}}

Ciramadol (WY-15,705) is an opioid analgesic that was developed in the late 1970s{{cite patent | country = US | number = 3928626 | title = Benzylamine Analgesics }} and is related to phencyclidine, tramadol, tapentadol and venlafaxine.{{cite journal | vauthors = Cochrane AD, Bell R, Sullivan JR, Shaw J | title = Ciramadol. A new analgesic | journal = The Medical Journal of Australia | volume = 2 | issue = 9 | pages = 501–2 | date = November 1979 | pmid = 522808 | doi = 10.5694/j.1326-5377.1979.tb125803.x}} It is a mixed agonist-antagonist for the μ-opioid receptor with relatively low abuse potential{{cite journal | vauthors = Preston KL, Bigelow GE, Liebson IA | title = Comparative evaluation of morphine, pentazocine and ciramadol in postaddicts | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 240 | issue = 3 | pages = 900–10 | date = March 1987 | doi = 10.1016/S0022-5347(25)00400-8 | pmid = 3559982 }} and a ceiling on respiratory depression{{cite journal | vauthors = Romagnoli A, Keats AS | title = Low ceiling respiratory depression by ciramadol | journal = International Journal of Clinical Pharmacology Research | volume = 6 | issue = 6 | pages = 451–5 | date = 1986 | pmid = 3100462 }} which makes it a relatively safe drug. It has a slightly higher potency and effectiveness as an analgesic than codeine,{{cite journal | vauthors = Downing JW, Brock-Utne JG, Holloway AM | title = Ciramadol--a new synthetic analgesic. A double-blind comparison with oral codeine for postoperative pain relief | journal = South African Medical Journal = Suid-Afrikaanse Tydskrif vir Geneeskunde | volume = 64 | issue = 25 | pages = 978–82 | date = December 1983 | pmid = 6359486 }} but is weaker than morphine.{{cite journal | vauthors = Powell WF | title = A double-blind comparison of multiple intramuscular doses of ciramadol, morphine, and placebo for the treatment of postoperative pain. | journal = Anesthesia and Analgesia | date = November 1985 | volume = 64 | issue = 11 | pages = 1101–7 | doi = 10.1213/00000539-198511000-00012 | pmid = 3901821 | url = https://dx.doi.org/10.1213%2F00000539-198511000-00012 }} Other side effects include sedation and nausea but these are generally less severe than with other similar drugs.{{cite journal | vauthors = Stambaugh JE, McAdams J | title = Comparison of the analgesic efficacy and safety oral ciramadol, codeine, and placebo in patients with chronic cancer pain | journal = Journal of Clinical Pharmacology | volume = 27 | issue = 2 | pages = 162–6 | date = February 1987 | pmid = 3680568 | doi = 10.1002/j.1552-4604.1987.tb02178.x | s2cid = 21229861 }}