Axomadol

Chemical compound

None

Legal statusLegal status

US: ?

Identifiers

IUPAC name

(1R,3R,6R)-6-[(dimethylamino)methyl]-1-(3-methoxyphenyl)-1,3-cyclohexanediol

CAS Number

187219-95-0
187219-99-4

PubChem CID

10221318

ChemSpider

8396810

UNII

B77S5W28H9

CompTox Dashboard (EPA)

DTXSID10171992

Chemical and physical dataFormulaC₁₆H₂₅NO₃Molar mass279.380 g·mol⁻¹3D model (JSmol)

Interactive image

SMILES

O[C@]2(c1cc(OC)ccc1)C[C@H](O)CC[C@@H]2CN(C)C

InChI

InChI=1S/C16H25NO3/c1-17(2)11-13-7-8-14(18)10-16(13,19)12-5-4-6-15(9-12)20-3/h4-6,9,13-14,18-19H,7-8,10-11H2,1-3H3/t13-,14-,16+/m1/s1
Key:LQJLLAOISDVBJM-FMKPAKJESA-N

Axomadol (INN, USAN) (code name EN3324) is a synthetic, centrally-acting opioid analgesic related to tramadol which was under investigation by Endo Pharmaceuticals in collaboration with Grünenthal GmbH for the treatment of chronic, moderate to severe lower back pain and arthrosis.^[1]^[2] Development was halted after phase II clinical trials as it did not meet the pre-determined clinical endpoints.^[3]

References

^ Ford C (2011-06-30). "Endo Announces Topline Results From Phase 2 Study of Axomadol in Chronic Low Back Pain" (Press release). Endo Pharmaceuticals. Retrieved 2012-05-11.
^ US Abandoned 20100331424, Schiene K, Bloms-Funke P, Bothmer J, Lefeber C, "Use of Axomadol for Treatment of Arthrosis Pain", published 2010-12-30, assigned to Grünenthal GmbH
^ Ford C (2011-08-17). "Endo Pharmaceuticals Announces Termination of Collaboration with Grunenthal for the Development of Axomadol" (Press release). Endo Pharmaceuticals. Retrieved 2012-05-11.

Analgesics (N02A, N02B)

Opioids

Opiates/opium	Codeine^# +aspirin +paracetamol Morphine^# (+naltrexone) Opium Laudanum Paregoric
Semisynthetic	Acetyldihydrocodeine Benzylmorphine Buprenorphine (+naloxone) Butorphanol Desomorphine Diamorphine (heroin) Dihydrocodeine (+paracetamol) Dihydromorphine Etorphine Ethylmorphine Hydrocodone (+paracetamol, +ibuprofen, +aspirin) Hydromorphinol Hydromorphone Levorphanol Metopon Nalbuphine Nicocodeine Nicodicodine Nicomorphine Oxycodone (+paracetamol, +aspirin, +ibuprofen, +naloxone, +naltrexone) Oxymorphone Papaveretum Thebacon
Synthetic	Alfentanil Alphaprodine Anileridine Bezitramide Carfentanil Dextromoramide Dextropropoxyphene Dezocine Dimenoxadol Dipipanone Ethoheptazine Fentanyl^# (+fluanisone) Ketobemidone Lofentanil Meptazinol Methadone^# NFEPP Norpipanone Oliceridine Pentazocine Pethidine (meperidine) Phenadoxone Phenazocine Phenoperidine Piminodine Piritramide Proheptazine Propiram Remifentanil Sufentanil Tapentadol Tilidine Tramadol (+celecoxib, +paracetamol) Viminol

Paracetamol-type

NSAIDs

Propionates	Benoxaprofen ^‡ Fenoprofen Flurbiprofen Ibuprofen^# (Dexibuprofen) (+paracetamol) Ketoprofen (Dexketoprofen) Loxoprofen Naproxen Oxaprozin Suprofen Tiaprofenic acid Zaltoprofen
Oxicams	Isoxicam Lornoxicam Meloxicam Piroxicam Tenoxicam
Acetates	Acemetacin Bromfenac Diclofenac Etodolac Indometacin (Indometacin farnesil) Ketorolac Sulindac Tolmetin Zomepirac ^‡
COX-2 inhibitors	Celecoxib (+tramadol) Etoricoxib Lumiracoxib ^‡ Parecoxib Rofecoxib ^‡ Valdecoxib ^‡
Fenamates	Flufenamic acid Meclofenamic acid Mefenamic acid Tolfenamic acid
Salicylates	Aspirin (acetylsalicylic acid)^# (+paracetamol/caffeine) Aloxiprin Benorylate Carbasalate calcium Choline salicylate Diflunisal Dipyrocetyl Ethenzamide Guacetisal Imidazole salicylate Magnesium salicylate Morpholine salicylate Potassium salicylate Salicin Salicylamide Salsalate Sodium salicylate Wintergreen (methyl salicylate)
Pyrazolones	Aminophenazone^‡ Ampyrone Metamizole (dipyrone) Nifenazone Phenazone Propyphenazone (+paracetamol/caffeine)
Others	Benzydamine Floctafenine Glafenine Nabumetone Nimesulide Proquazone

Cannabinoids

Ion channel
modulators

Calcium blockers	Alcohol (ethanol) Gabapentin Gabapentin enacarbil Leconotide Mirogabalin Pregabalin Ziconotide
Sodium blockers	Carbamazepine Lacosamide Local anesthetics (e.g., cocaine, lidocaine) Mexiletine Nefopam Tricyclic antidepressants (e.g., amitriptyline^#) Na_v1.7/1.8-selective: DSP-2230^§ Funapide^§ PF-05089771^§
Potassium openers	Flupirtine^‡