:Bromadoline

{{Short description|Opioid analgesic drug}}

{{Distinguish|Bromadol|Bromadiolone}}

{{Drugbox

| Watchedfields = changed

| verifiedrevid = 462780619

| IUPAC_name = 4-bromo-N-[(1R,2R)-2-(dimethylamino)cyclohexyl]benzamide

| image = U-47931E_structure.png

| chirality =

| tradename =

| pregnancy_category =

| legal_status =

| routes_of_administration =

| bioavailability =

| metabolism =

| elimination_half-life =

| excretion =

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

| CAS_number = 2418521-61-4

| CAS_supplemental = 67579-24-2 (mixture of trans isomers)

| ATC_prefix = none

| ATC_suffix =

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

| UNII = R8DWN01P1M

| synonyms = Bromadoline

| PubChem = 6328449

| ChEMBL =

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID =

| C=15 | H=21 | Br=1 | N=2 | O=1

| smiles = CN(C)[C@@H]1CCCC[C@H]1NC(=O)C2=CC=C(C=C2)Br

| StdInChI = 1S/C15H21BrN2O/c1-18(2)14-6-4-3-5-13(14)17-15(19)11-7-9-12(16)10-8-11/h7-10,13-14H,3-6H2,1-2H3,(H,17,19)/t13-,14-/m1/s1

| StdInChIKey = UFDJFJYMMIZKLG-ZIAGYGMSSA-N

}}

Bromadoline (U-47931E){{cite book | title = Unlisted Drugs | volume = 34–35 | page = 392 | date = 1982 | publisher = Pharmaceutical Section, Special Libraries Association | location = Chatham | isbn = 978-0-913210-13-0 }} is an opioid analgesic selective for the μ-opioid receptor{{cite journal | vauthors = Hayes AG, Skingle M, Tyers MB | title = Evaluation of the receptor selectivities of opioid drugs by investigating the block of their effect on urine output by beta-funaltrexamine | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 240 | issue = 3 | pages = 984–8 | date = March 1987 | doi = 10.1016/S0022-5347(25)00406-9 | pmid = 3559988 | url = http://jpet.aspetjournals.org/content/240/3/984.abstract | url-access = subscription }} developed by the Upjohn company in the 1970s.{{cite web | url=https://patents.google.com/patent/US4098904 | title=Patent US4098904 - Analgesic N-(2-aminocycloaliphatic)benzamides | date=4 July 1978 | author=Jacob Szmuszkovicz | publisher=The Upjohn Company}} The drug has a potency lying between that of codeine and morphine, being slightly stronger than pentazocine.{{cite journal | vauthors = Hayes AG, Sheehan MJ, Tyers MB | title = Differential sensitivity of models of antinociception in the rat, mouse and guinea-pig to mu- and kappa-opioid receptor agonists | journal = British Journal of Pharmacology | volume = 91 | issue = 4 | pages = 823–32 | date = August 1987 | pmid = 2822190 | pmc = 1853585 | doi = 10.1111/j.1476-5381.1987.tb11281.x }} Bromadoline is related to AH-7921 and U-47700.{{cite journal | vauthors = Cheney BV, Szmuszkovicz J, Lahti RA, Zichi DA | title = Factors affecting binding of trans-N-[2-(methylamino)cyclohexyl]benzamides at the primary morphine receptor | journal = Journal of Medicinal Chemistry | volume = 28 | issue = 12 | pages = 1853–64 | date = December 1985 | pmid = 2999404 | doi = 10.1021/jm00150a017 }}