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Tramadol

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Also known as AmandaCG-315EE-265E265ETS-6103ETS6103U-26255AUltracetrel-tramadol

Summary

Tramadol (CHEMBL1237044) is an approved small molecule (ATC N02AX02) targeting OPRD1, OPRK1, and OPRM1; indicated across 20 conditions including opiate dependence and fibromyalgia.

At a glance

  • Status: Approved (max clinical phase 4)
  • Modality: Small molecule
  • ATC class: N02AX02
  • Targets: 3 (OPRD1, OPRK1, OPRM1)
  • Indications: 20 conditions
  • Clinical trials: 226
  • Chemistry: 263.37 Da · C16H25NO2

Identifiers

Drug identity and classification

FieldValue
ChEMBL IDCHEMBL1237044
NameTramadol
TypeSmall molecule
Max phase4
FDA approvedno
PubChem CID5523
ChEBICHEBI:75722
ATCN02AX02
Molecular formulaC16H25NO2
Molecular weight263.37
InChIKeyTVYLLZQTGLZFBW-UHFFFAOYSA-N

SMILES: CN(C)CC1CCCCC1(C2=CC(=CC=C2)OC)O

IUPAC name: 2-[(dimethylamino)methyl]-1-(3-methoxyphenyl)cyclohexan-1-ol

ChEBI definition: A tertiary alcohol that is cyclohexanol substituted at positions 1 and 2 by 3-methoxyphenyl and dimethylaminomethyl groups respectively.

Also known as: Amanda, CG-315E, E-265, E265, ETS-6103, ETS6103, Tramadol, U-26255A, Ultracet, tramadol, rel-tramadol, rel-Tramadol

Parent form; salt/anhydrous children: CHEMBL1237065

Patent coverage: 138 distinct patent families (422 SureChEMBL compound mentions), from 1 matched compound structure(s). Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Primary targets (GtoPdb curated mechanism): the Cancer dependency column is the DepMap CRISPR fitness signal (% of screened cell lines dependent on the target).

GeneTargetActionpAffinityCancer dependencyUniProt
OPRD1δ receptorAgonist8.030.2%P41143
OPRK1κ receptorAgonist7.850%P41145
OPRM1μ receptorAgonist5.80%P35372

Broader ChEMBL bioactivity targets: 9 (assay-derived). Sample: Muscarinic acetylcholine receptor M2, Muscarinic acetylcholine receptor M1, Sodium-dependent noradrenaline transporter, Sodium-dependent serotonin transporter, Mu-type opioid receptor, Delta-type opioid receptor, Kappa-type opioid receptor, Mu-type opioid receptor, Solute carrier family 22 member 1.

Bioactivity

ChEMBL activities: 16 potent at pChembl ≥ 5 of 18 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

TargetpChemblTypeValueUnitActivity ID
OPRD18.03Ki9.4nMCHEMBL_ACT_2263708
OPRK17.85Ki14nMCHEMBL_ACT_2263707
SLC6A46.7Ki198nMCHEMBL_ACT_7798089
SLC6A46.43IC50372nMCHEMBL_ACT_7798088
SLC6A26.1IC50790nMCHEMBL_ACT_1679566
OPRM15.89EC501300nMCHEMBL_ACT_10940234
SLC6A45.83IC501493nMCHEMBL_ACT_2103939
CHRM25.83AC501471nMCHEMBL_ACT_25195421
OPRM15.8Ki1600nMCHEMBL_ACT_2263709
SLC6A45.7AC502000nMCHEMBL_ACT_25150981
OPRM15.7Ki2000nMCHEMBL_ACT_252397
P335355.62Ki2400nMCHEMBL_ACT_6357151
SLC6A25.41IC503861nMCHEMBL_ACT_2103940
SLC6A45.37IC504300nMCHEMBL_ACT_1679565
OPRM15.12IC507600nMCHEMBL_ACT_1679564
OPRM15.12IC507600nMCHEMBL_ACT_2103938

Target pathways

Aggregated over 3 target gene(s): OPRD1, OPRK1, OPRM1.

Top Reactome pathways

6 total, by targets touching each:

PathwayTargetsGenes
Peptide ligand-binding receptors3OPRD1, OPRK1, OPRM1
G alpha (i) signalling events3OPRD1, OPRK1, OPRM1
Interleukin-4 and Interleukin-13 signaling2OPRD1, OPRM1
MECP2 regulates neuronal receptors and channels2OPRK1, OPRM1
Opioid Signalling1OPRM1
G-protein activation1OPRM1

Dominant GO biological processes

GO termTargets
G protein-coupled receptor signaling pathway3
adenylate cyclase-inhibiting G protein-coupled receptor signaling pathway3
phospholipase C-activating G protein-coupled receptor signaling pathway3
neuropeptide signaling pathway3
G protein-coupled opioid receptor signaling pathway3
signal transduction3
immune response2
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messenger2
response to nicotine2
eating behavior2
response to ethanol2
sensory perception2
sensory perception of pain2
adult locomotory behavior1
negative regulation of gene expression1

Indications & clinical

Indications

20 indications (1 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).

IndicationTrial phaseMONDOEFO
opiate dependence3MONDO:0005530EFO:0005611
fibromyalgia3MONDO:0005546EFO:0005687
neuralgia3MONDO:0021667EFO:0005762
diabetic neuropathy3MONDO:0006626EFO:1000783
osteoarthritis, knee3MONDO:0005416EFO:0004616
injury2MONDO:0021178EFO:0000546
hip fracture2MONDO:0005327EFO:0003964
substance withdrawal syndrome2MONDO:0005567EFO:0005800
rotator cuff syndrome2MONDO:0007028EFO:1001250
major depressive disorder2MONDO:0002009MONDO:0002009
breast neoplasm2MONDO:0021100MONDO:0007254
head and neck squamous cell carcinoma2MONDO:0010150EFO:0000181
osteoarthritis2MONDO:0005178MONDO:0005178
neoplasm2MONDO:0005070MONDO:0004992
acute pancreatitis0MONDO:0006515EFO:1000652

5 further indication records had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.

Clinical trials

Total trials: 226.

Phase distribution

PhaseTrials
PHASE474
Not specified57
PHASE344
PHASE222
PHASE114
PHASE2/PHASE37
PHASE1/PHASE26
EARLY_PHASE12

Top trials by phase / activity

NCTPhaseStatusTitle
NCT03781544PHASE4RECRUITINGEffects of Opioids and NSAIDs on Sympathetic Nervous System and Vascular Function
NCT05488847PHASE4ACTIVE_NOT_RECRUITINGOpioid-Free Pain Protocol After Shoulder Arthroplasty
NCT06269770PHASE4RECRUITINGTapentadol vs Tramadol in Total Knee Arthroplasty
NCT06373978PHASE4RECRUITINGNonNarcotic Pain Control in Percutaneous Needle Tenotomy of Elbow
NCT06612996PHASE4NOT_YET_RECRUITINGIntravenous Tramadol and Magnesium Sulphate for Prevention of Shivering
NCT06742554PHASE4ACTIVE_NOT_RECRUITINGComparative Efficacy of Buprenorphine Transdermal Patch Versus Tramadol in Postoperative Analgesia for Shoulder Arthroscopy
NCT07064993PHASE4NOT_YET_RECRUITINGEffects of Intraarticular Tramadol and Tramadol-Dexamethasone on Postoperative Pain After Knee Arthroscopy
NCT07066111PHASE4NOT_YET_RECRUITINGThe Effect of Bupivacaine Liposome Preemptive Analgesia on Postoperative Pain and Delirium in Elderly Patients Undergoing Hip Fracture Surgery
NCT07153003PHASE4ENROLLING_BY_INVITATIONEfficacy And Safety Of Tramadol And Oxycodone Versus Oxycodone Monotherapy For Pain Control After Primary Total Knee And Total Hip Arthroplasty
NCT00210561PHASE4TERMINATEDA Study of the Effectiveness and Safety of Tramadol HCl/Acetaminophen Compared to Placebo in Treating Acute Low Back Pain
NCT00236483PHASE4COMPLETEDA Comparison of the Effectiveness and Safety of ULTRACET® (Tramadol Hydrochloride/Acetaminophen) Versus ULTRAM® (Tramadol Hydrochloride) Versus Placebo in Patients With Pain After Oral Surgery
NCT00246168PHASE4COMPLETEDULTRACET (Tramadol Hydrochloride and Acetaminophen) for the Treatment of Rheumatoid Arthritis Pain.
NCT00290901PHASE4COMPLETEDCelebrex vs Tramadol in the Treatment of Chronic Lower Back Pain.
NCT00426647PHASE4COMPLETEDNorspan® Patches Versus Tramadol in Subjects With Chronic, Moderate to Severe Osteoarthritis Pain in the Hip Knee and/or Lumbar Spine
NCT00560443PHASE4COMPLETEDRCT on Ketorolac and Tramadol in Bone Fractures Pain of Child
NCT00635349PHASE4COMPLETEDA Comparative Study of Tramadol Hydrochloride Plus Acetaminophen Tablets Maintenance Versus Non-Steroidal Anti-Inflammatory Drugs (NSAIDs) Maintenance in Participants With Knee Osteoarthritis
NCT00647517PHASE4COMPLETEDTramadol/Acetaminophen(Ultracet) AS add-on Therapy in the Treatment of Patients With Ankylosing Spondylitis
NCT00692263PHASE4COMPLETEDThe Effect of Escitalopram on the Pharmacokinetics and Pharmacodynamics of Tramadol in Healthy Subjects
NCT00733421PHASE4COMPLETEDThe Effect of Anti-inflammatory Analgesics on Pain Following Hallux Valgus Surgery
NCT00766402PHASE4TERMINATEDAn Efficacy and Safety Study of Tramadol/Acetaminophen Versus Diclofenac in the Treatment of Pain in Participants With Ankylosing Spondylitis Receiving Stable Treatment of Disease Modifying Anti-rheumatic Drugs (DMARDs)
NCT00785603PHASE4UNKNOWNParoxetines Effect on Tramadols Metabolism and Pharmakodynamics: a Dose Response Study
NCT00942565PHASE4COMPLETEDAdjuvant Analgesic Effects of Low Dose Tramadol/Acetaminophen Combination After Open Gynaecological Surgery
NCT01063842PHASE4COMPLETEDA Study of the Tolerability of Titrated Dose Tramadol/Acetaminophen Combination Tablet in Korean Patients With Osteoarthritis
NCT01116531PHASE4WITHDRAWNEfficacy, Safety, Tolerability and Pharmacokinetics of Concomitant Administration of Tramadol With Duloxetine or Pregabalin
NCT01267136PHASE4COMPLETEDA Comparison of Postoperative Tramadol Versus Acetaminophen With Codeine in Children Undergoing Tonsillectomy
NCT01416116PHASE4COMPLETEDMethod of Pre-treatment for Application of QUTENZA Capsaicin 8% Patch
NCT01517711PHASE4COMPLETEDTramadol Extended-Release (ER) for Posttraumatic Stress Disorder (PTSD)
NCT01526525PHASE4COMPLETEDPerioperative Electroacupuncture on Postoperative Analgesia in Prostatectomy
NCT01728246PHASE4COMPLETEDAn Efficacy, Safety and Effects on Quality of Life of Tramadol/Paracetamol as Add-on Therapy in Chronic Osteoarthritis
NCT01843660PHASE4COMPLETEDAn Efficacy and Safety Study of Tramadol Hydrochloride-Paracetamol in Treatment of Moderate to Severe Acute Neck-Shoulder Pain and Low Back Pain
NCT01887951PHASE4COMPLETEDPenthrox Versus Tramadol for SCDF
NCT01943760PHASE4COMPLETEDTamadol Wound Infiltration in Children Under Inguinal Hernioplasty
NCT01983111PHASE4COMPLETEDCompare the Efficacy and Safety of Norspan to Tramadol/Acetaminophen With Prolonged Postoperative Pain (PASSION)
NCT02076893PHASE4TERMINATEDPostoperative Tramadol/Gabapentin/Ibuprofen Versus Tramadol/Placebo/Ibuprofen
NCT02246712PHASE4COMPLETEDInfluence of Diabetes on Tramadol Pharmacokinetics
NCT02248493PHASE4COMPLETEDIntravenous Paracetamol for Postoperative Pain
NCT02291705PHASE4COMPLETEDUltrasound-guided Rectus Sheath Block In Children
NCT02327923PHASE4COMPLETEDIntraoperative Lidocaine Infusion vs. Esmolol Infusion for Postoperative Analgesia in Laparoscopic Cholecystectomy
NCT02412930PHASE4COMPLETEDComparative Study of Ultrasound-guided Paravertebral Block Versus Intravenous Tramadol in Percutaneous Nephrolithotomy
NCT02416804PHASE4COMPLETEDPostoperative Analgesia With Buprenorphine for Postoperative Pain Control and Quality of Life After Spinal Surgery

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

No PharmGKB pharmacogenomic data curated for this drug.

Molecules sharing ≥1 of this drug’s curated primary targets, merged from two biobtree sources and ranked by shared-target count, then clinical phase: ChEMBL clinical-stage candidates (development phase ≥2) and PubChem drug-class bioactivity (approved / known drugs acting on the target). Deduplicated by drug name; the drug’s own salt forms are excluded. Note: for a drug with few primary targets a shared-target match can reflect off-target / promiscuous binding rather than the same therapeutic mechanism — the phase ordering surfaces bona-fide therapeutics first.

612 molecules share ≥1 primary target. Top 60 by shared-target count:

MoleculeSourceStatusShared targets
DihydroergotamineChEMBL + PubChemPhase 4 (approved)OPRD1, OPRK1, OPRM1
PROPOXYPHENEChEMBL + PubChemPhase 4 (approved)OPRD1, OPRK1, OPRM1
TAFAMIDISChEMBL + PubChemPhase 4 (approved)OPRD1, OPRK1, OPRM1
ALVIMOPANChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
AMIODARONEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
AMLODIPINEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
AMOXAPINEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
ASTEMIZOLEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
BENZTROPINEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
BUPRENORPHINEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
BUTORPHANOLChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
CANDESARTAN CILEXETILChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
CANNABIDIOLChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
CHLORPROMAZINEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
CINNARIZINEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
CLOTRIMAZOLEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
CODEINEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
DIETHYLSTILBESTROLChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
ECONAZOLEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
FENTANYLChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
FLUPHENAZINEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
FLUSPIRILENEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
HYDROCODONEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
HYDROMORPHONEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
LANSOPRAZOLEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
LEVORPHANOLChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
LOPERAMIDEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
LOXAPINEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
MEPERIDINEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
METHADONEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
METHYLNALTREXONEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
MICONAZOLEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
MORPHINEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
NAFTOPIDILChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
NALBUPHINEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
NALFURAFINEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
NALMEFENEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
NALOXONEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
NALTREXONEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
NELFINAVIRChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
OLICERIDINEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
OXYCODONEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
OXYMORPHONEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
PAROXETINEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
PASIREOTIDEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
PENTAZOCINEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
PIMOZIDEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
RALOXIFENEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
RITONAVIRChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
SAMIDORPHANChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
SAQUINAVIRChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
SUNITINIBChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
TAMOXIFENChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
ASIMADOLINEChEMBLPhase 3OPRD1, OPRK1, OPRM1
ATICAPRANTChEMBLPhase 3OPRD1, OPRK1, OPRM1
CEBRANOPADOLChEMBLPhase 3OPRD1, OPRK1, OPRM1
NAVACAPRANTChEMBLPhase 3OPRD1, OPRK1, OPRM1
TRIMEBUTINEChEMBLPhase 3OPRD1, OPRK1, OPRM1
BREMAZOCINEChEMBLPhase 2OPRD1, OPRK1, OPRM1
CARFENTANILChEMBLPhase 2OPRD1, OPRK1, OPRM1

About this page

Generated deterministically by Sugi Atlas from primary biomedical databases via BioBTree. Every record on this page traces to a primary source.

Generated
Atlas version
v1.1.2
BioBTree
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Sources 30

This page pulls from 30 datasets indexed by BioBTree:

chebichembl_activitychembl_moleculechembl_targetcivic_evidenceclingen_dosageclinical_trialsdepmapefoensemblentrezgogoparentgtopdbgtopdb_interactiongtopdb_ligandhgncmeshmondomsigdbpatent_compoundpharmgkbpharmgkb_guidelinepubchempubchem_activityreactomereactomeparentrefseqtranscriptuniprot