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Compound Detail

CHEMBL1237044

TRAMADOL
💊 Approved Drug
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💊 Approved Drug
COc1cccc(C2(O)CCCCC2CN(C)C)c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1237044
Name TRAMADOL
Phase Approved
Structure Type MOL
InChI Key TVYLLZQTGLZFBW-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Amanda CG-315E E-265 E265 ETS-6103 ETS6103 Tramadol U-26255A Ultracet
7
Targets
15
Activities
3
Assay Types
16
PK Parameters
20
Publications
9
Known Names
20
Indications

Molecular Properties

263.4
MW (Da)
2.63
ALogP
3
HBA
1
HBD
32.7
PSA (Ų)
0.91
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1995
Availability Prescription
Chirality Racemic

Routes of Administration

Oral

Flags

Black Box Warning Natural Product
USAN Stem -adol
USAN Year 1969

Extended Properties

Molecular Formula C16H25NO2
MW 263.38
Aromatic Rings 1
Heavy Atoms 19
NP-Likeness 0.43

Indications

Pain Abdominal Pain Chronic Pain Diabetic Neuropathies Fibromyalgia Low Back Pain Neuralgia Opioid-Related Disorders Osteoarthritis, Knee Breast Neoplasms Carcinoma, Squamous Cell Depressive Disorder, Major Hip Fractures Neoplasms Osteoarthritis Rotator Cuff Injuries Substance Withdrawal Syndrome Wounds and Injuries Uveal Melanoma Pancreatitis

ATC Classification

N02AX02
tramadol
Level 1: NERVOUS SYSTEM
Level 2: ANALGESICS

Activity Summary

IC50 8 meas. best 6.43
Ki 6 meas. best 8.03
EC50 1 meas. best 5.89

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Delta-type opioid receptor
CHEMBL236
 Ki 8.03 8.03 9.4 1
Kappa-type opioid receptor
CHEMBL237
 Ki 7.85 7.85 14.0 1
Sodium-dependent serotonin transporter
CHEMBL228
 Ki 6.7 6.7 198.0 1
Sodium-dependent serotonin transporter
CHEMBL228
 IC50 6.43 5.8767 372.0 3
Sodium-dependent noradrenaline transporter
CHEMBL222
 IC50 6.1 5.755 790.0 2
Mu-type opioid receptor
CHEMBL233
 EC50 5.89 5.89 1300.0 1
Mu-type opioid receptor
CHEMBL233
 Ki 5.8 5.75 1600.0 2
Mu-type opioid receptor
CHEMBL270
 Ki 5.62 5.62 2400.0 1
Mu-type opioid receptor
CHEMBL233
 IC50 5.12 5.12 7600.0 2
Solute carrier family 22 member 1
CHEMBL5685
 IC50 4.28 4.28 52500.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 6.5 mL.min-1.kg-1 Homo sapiens
CL 5.5 mL.min-1.kg-1 Homo sapiens
CL 6.5 mL.min-1.kg-1 Homo sapiens
CL 6.5 mL.min-1.kg-1 Homo sapiens
F 79.0 % Homo sapiens
F 75.0 % Homo sapiens
F 36.0 % Rattus norvegicus
Fu 0.8 - Homo sapiens
Fu 0.8 - Homo sapiens
Fu 0.85 - Rattus norvegicus
Fu 0.53 - Rattus norvegicus
MRT 7.2 hr Homo sapiens
T1/2 12.35 hr Homo sapiens
T1/2 16.13 hr Homo sapiens
T1/2 5.8 hr Homo sapiens
Vd 4.2 L.kg-1 Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Delta-type opioid receptor Ki = 9.4 nM 8.03 Displacement of [3H]Naltrindole form human delta opioid receptor expressed in CH... 19027293
Kappa-type opioid receptor Ki = 14.0 nM 7.85 Displacement of [3H]U69593 form human kappa opioid receptor expressed in CHO cel... 19027293
Sodium-dependent serotonin transporter Ki = 198.0 nM 6.7 DRUGMATRIX: Transporter, Serotonin (5-Hydroxytryptamine) (SERT) radioligand bind... -
Sodium-dependent serotonin transporter IC50 = 372.0 nM 6.43 DRUGMATRIX: Transporter, Serotonin (5-Hydroxytryptamine) (SERT) radioligand bind... -
Sodium-dependent noradrenaline transporter IC50 = 790.0 nM 6.1 Inhibition of reuptake of Norepinephrine 16257206
Mu-type opioid receptor EC50 = 1300.0 nM 5.89 Agonist activity at human mu opioid receptor expressed in CHO cells assessed as ... 24900459
Sodium-dependent serotonin transporter IC50 = 1493.0 nM 5.83 Inhibition of SERT mediated 5-hydroxytryptamine uptake 18242987
Mu-type opioid receptor Ki = 1600.0 nM 5.8 Displacement of [3H]DAMGO form human mu opioid receptor expressed in CHO cells 19027293
Mu-type opioid receptor Ki = 2000.0 nM 5.7 Opioid receptor mu 1 agonist activity with monoamine (NE, 5-HT) uptake-blocking ... 10229619
Mu-type opioid receptor Ki = 2400.0 nM 5.62 Displacement of [3H]-dihydromorphine from mu opioid receptor in rat cerebral cor... 21864951
Sodium-dependent noradrenaline transporter IC50 = 3861.0 nM 5.41 Inhibition of NET mediated norepinephrine uptake 18242987
Sodium-dependent serotonin transporter IC50 = 4300.0 nM 5.37 Inhibition of reuptake of 5HT 16257206
Mu-type opioid receptor IC50 = 7600.0 nM 5.12 Inhibition of mu opioid receptor 16257206
Mu-type opioid receptor IC50 = 7600.0 nM 5.12 Binding affinity to mu opioid receptor 18242987
Solute carrier family 22 member 1 IC50 = 52500.0 nM 4.28 Inhibition of 4-(4-(dimethylamino)styryl)-N-methylpyridinium uptake at human OCT... 18788725

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 408
16472241 10.2174/1570163043334794 Hepatotoxicity 18
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
20070106 10.1021/jm901371v Homo sapiens 8
19764786 10.1021/jm901036q Plasma 4
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 4
18426954 10.1124/dmd.108.020479 ADMET 4
37468498 10.1038/s41467-023-40064-9 Alpha-2A adrenergic receptor 3
37468498 10.1038/s41467-023-40064-9 Cannabinoid receptor 1 3
18242987 10.1016/j.bmcl.2008.01.051 Rattus norvegicus 3
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M2 3
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2A 3
20014752 10.1021/tx900326k Hepatotoxicity 3
21149540 10.1124/dmd.110.035998 Brain 3
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2B 3
18027916 10.1021/jm070524a No relevant target 2
19764786 10.1021/jm901036q ADMET 2
10891117 10.1021/jm0000564 ADMET 2

Data from ChEMBL 36 via Core Engine