nefopam ๐Ÿถ Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
1891 13669-70-0

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • nefopam
  • fenazoxine
  • (+/-)-Nefopam
  • nefopam hydrochloride
  • nefopam HCl
Non-narcotic analgesic chemically similar to ORPHENADRINE. Its mechanism of action is unclear. It is used for the relief of acute and chronic pain. (From Martindale, The Extra Pharmacopoeia, 30th ed, p26)
  • Molecular weight: 253.35
  • Formula: C17H19NO
  • CLOGP: 2.91
  • LIPINSKI: 0
  • HAC: 2
  • HDO: 0
  • TPSA: 12.47
  • ALOGS: -3.50
  • ROTB: 1

Drug dosage:

None

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 34 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 3 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 1.04 ยตM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 36 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 5.60 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 12 mL/min/kg Lombardo F, Berellini G, Obach RS
t_half (Half-life) 5 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Jan. 1, 1978 YEAR INTRODUCED

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Hepatocellular injury 371.17 25.81 124 5339 27257 63456302
Cholestasis 335.19 25.81 117 5346 29317 63454242
Hepatic cytolysis 136.70 25.81 51 5412 15356 63468203
Acute kidney injury 135.18 25.81 138 5325 263277 63220282
Acute generalised exanthematous pustulosis 125.65 25.81 44 5419 11055 63472504
Drug reaction with eosinophilia and systemic symptoms 95.28 25.81 50 5413 33786 63449773
Thrombocytopenia 88.05 25.81 85 5378 151072 63332487
Coma 72.45 25.81 53 5410 64311 63419248
Foetal megacystis 70.81 25.81 10 5453 26 63483533
Drug dependence 65.56 25.81 35 5428 24448 63459111
Pancreatitis acute 64.88 25.81 36 5427 27130 63456429
Tonic clonic movements 61.98 25.81 16 5447 1419 63482140
Fatigue 58.25 25.81 5 5458 888023 62595536
Metabolic acidosis 57.34 25.81 40 5423 45029 63438530
Peripheral nerve injury 56.86 25.81 12 5451 439 63483120
Anticholinergic syndrome 53.95 25.81 16 5447 2366 63481193
Shock haemorrhagic 47.20 25.81 21 5442 9874 63473685
Mixed liver injury 46.86 25.81 17 5446 4718 63478841
Miosis 46.31 25.81 19 5444 7334 63476225
Spinal epidural haemorrhage 45.93 25.81 8 5455 102 63483457
Hyperkalaemia 40.29 25.81 35 5428 54168 63429391
Cell death 40.04 25.81 13 5450 2588 63480971
Encephalopathy 39.40 25.81 30 5433 38590 63444969
Epidural haemorrhage 38.25 25.81 7 5456 120 63483439
Myoclonus 37.80 25.81 21 5442 15847 63467712
Shock 37.48 25.81 24 5439 23439 63460120
Drug ineffective 37.36 25.81 22 5441 1044743 62438816
Urinary bladder rupture 36.91 25.81 7 5456 147 63483412
Somnolence 35.89 25.81 59 5404 178626 63304933
Hyponatraemia 35.69 25.81 46 5417 111854 63371705
Eosinophilia 35.66 25.81 23 5440 22733 63460826
Granulomatous liver disease 35.18 25.81 9 5454 769 63482790
Hyperlactacidaemia 34.95 25.81 12 5451 2837 63480722
Anaphylactic shock 34.87 25.81 23 5440 23610 63459949
Cutaneous T-cell lymphoma 34.46 25.81 10 5453 1370 63482189
Pancreatic pseudoaneurysm 34.34 25.81 6 5457 78 63483481
Foetal heart rate abnormal 31.93 25.81 8 5455 629 63482930
Naevus haemorrhage 31.68 25.81 6 5457 125 63483434
Stevens-Johnson syndrome 31.38 25.81 22 5441 24928 63458631
Agranulocytosis 31.23 25.81 22 5441 25112 63458447
Neutropenia 30.16 25.81 54 5409 174951 63308608
Epidural analgesia 30.01 25.81 5 5458 48 63483511
Porphyria 29.98 25.81 6 5457 168 63483391
Poisoning deliberate 29.91 25.81 16 5447 11202 63472357
Blood phosphorus decreased 29.73 25.81 12 5451 4441 63479118
Prescription drug used without a prescription 29.07 25.81 10 5453 2376 63481183
Livedo reticularis 28.89 25.81 10 5453 2422 63481137
Pain 28.74 25.81 14 5449 740614 62742945
Confusional state 28.73 25.81 63 5400 236317 63247242
Autonomic nervous system imbalance 27.45 25.81 10 5453 2808 63480751

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Agranulocytosis 203.25 29.28 83 3958 23738 34929152
Drug reaction with eosinophilia and systemic symptoms 155.82 29.28 76 3965 32936 34919954
Cholestasis 154.66 29.28 71 3970 26877 34926013
Rash maculo-papular 150.98 29.28 71 3970 28380 34924510
Hepatocellular injury 135.24 29.28 61 3980 22150 34930740
Eosinophilia 131.63 29.28 63 3978 26159 34926731
Confusional state 91.33 29.28 97 3944 144063 34808827
Alveolar lung disease 84.11 29.28 17 4024 369 34952521
Pulmonary interstitial emphysema syndrome 78.93 29.28 17 4024 507 34952383
Toxic skin eruption 65.21 29.28 30 4011 11355 34941535
Pancytopenia 63.63 29.28 66 3975 95091 34857799
Hyperleukocytosis 60.64 29.28 18 4023 1984 34950906
Diffuse alveolar damage 58.07 29.28 18 4023 2296 34950594
Urethral valves 52.93 29.28 11 4030 275 34952615
Acute kidney injury 52.28 29.28 111 3930 304877 34648013
Mixed liver injury 50.27 29.28 17 4024 2856 34950034
Eosinophilic pneumonia 46.98 29.28 17 4024 3484 34949406
Hyperammonaemia 46.83 29.28 20 4021 6347 34946543
Anaphylactic shock 44.73 29.28 26 4015 15915 34936975
Oesophageal achalasia 43.87 29.28 10 4031 388 34952502
Consciousness fluctuating 41.81 29.28 12 4029 1175 34951715
Haemolytic anaemia 40.17 29.28 21 4020 10458 34942432
Hallucination, visual 34.64 29.28 23 4018 17768 34935122
Generalised oedema 34.18 29.28 20 4021 12388 34940502
Hepatic encephalopathy 33.57 29.28 21 4020 14664 34938226
Hepatitis 32.89 29.28 25 4016 23879 34929011
Amnesia 32.68 29.28 26 4015 26537 34926353
Pancreatitis acute 29.29 29.28 25 4016 28116 34924774

FDA Adverse Event Reporting System (Geriatric)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Hepatocellular injury 465.37 22.55 185 9408 47408 79687387
Cholestasis 452.54 22.55 186 9407 51923 79682872
Drug reaction with eosinophilia and systemic symptoms 231.38 22.55 125 9468 64119 79670676
Agranulocytosis 206.27 22.55 103 9490 44927 79689868
Acute kidney injury 158.18 22.55 248 9345 519156 79215639
Eosinophilia 156.97 22.55 86 9507 45259 79689536
Hepatic cytolysis 148.04 22.55 70 9523 27081 79707714
Rash maculo-papular 142.54 22.55 87 9506 55991 79678804
Acute generalised exanthematous pustulosis 130.75 22.55 56 9537 17198 79717597
Thrombocytopenia 102.54 22.55 142 9451 265117 79469678
Confusional state 96.64 22.55 152 9441 317845 79416950
Mixed liver injury 90.01 22.55 34 9559 7544 79727251
Pancreatitis acute 89.26 22.55 62 9531 49542 79685253
Toxic skin eruption 84.68 22.55 45 9548 22248 79712547
Pulmonary interstitial emphysema syndrome 78.26 22.55 17 9576 506 79734289
Alveolar lung disease 76.60 22.55 17 9576 560 79734235
Fatigue 75.87 22.55 11 9582 929716 78805079
Coma 74.09 22.55 75 9518 100574 79634221
Anaphylactic shock 69.50 22.55 47 9546 35949 79698846
Drug dependence 61.96 22.55 46 9547 40723 79694072
Tonic clonic movements 61.95 22.55 19 9574 2245 79732550
Pancytopenia 58.41 22.55 85 9508 165660 79569135
Encephalopathy 56.61 22.55 54 9539 67343 79667452
Hyperleukocytosis 55.21 22.55 18 9575 2592 79732203
Hepatitis 53.28 22.55 48 9545 55679 79679116
Drug ineffective 50.91 22.55 34 9559 1080879 78653916
Diffuse alveolar damage 49.52 22.55 18 9575 3586 79731209
Miosis 49.27 22.55 28 9565 15761 79719034
Cell death 48.37 22.55 19 9574 4680 79730115
Peripheral nerve injury 47.37 22.55 12 9581 702 79734093
Neutropenia 46.40 22.55 105 9488 287605 79447190
Haemolytic anaemia 46.13 22.55 28 9565 17792 79717003
Febrile bone marrow aplasia 43.10 22.55 24 9569 12996 79721799
Anticholinergic syndrome 42.15 22.55 16 9577 3595 79731200
Metabolic acidosis 40.85 22.55 50 9543 82479 79652316
Gamma-glutamyltransferase increased 40.66 22.55 41 9552 54639 79680156
Shock haemorrhagic 40.65 22.55 27 9566 20033 79714762
Eosinophilic pneumonia 39.44 22.55 17 9576 5293 79729502
Hyperammonaemia 38.23 22.55 21 9572 11072 79723723
Oesophageal achalasia 36.61 22.55 10 9583 784 79734011
Urinary retention 35.91 22.55 39 9554 56591 79678204
Hyperthermia 35.88 22.55 24 9569 18013 79716782
Consciousness fluctuating 35.35 22.55 12 9581 1957 79732838
Spinal epidural haemorrhage 34.56 22.55 7 9586 147 79734648
Hyperbilirubinaemia 33.57 22.55 26 9567 24492 79710303
Pneumonia 33.44 22.55 19 9574 660227 79074568
Foetal heart rate abnormal 33.28 22.55 8 9585 376 79734419
Pain 33.22 22.55 22 9571 703780 79031015
Myoclonus 32.89 22.55 27 9566 27633 79707162
Poisoning deliberate 32.60 22.55 23 9570 18805 79715990
Pancreatic pseudoaneurysm 32.33 22.55 6 9587 78 79734717
Epidural haemorrhage 31.89 22.55 7 9586 219 79734576
Hepatic encephalopathy 31.73 22.55 25 9568 24141 79710654
Hallucination, visual 30.90 22.55 28 9565 32701 79702094
Prothrombin time ratio decreased 30.65 22.55 9 9584 916 79733879
Naevus haemorrhage 29.67 22.55 6 9587 125 79734670
Hyperlactacidaemia 29.17 22.55 14 9579 5581 79729214
Hallucination 28.76 22.55 43 9550 85702 79649093
Transaminases increased 28.31 22.55 33 9560 51710 79683085
Epidural analgesia 28.15 22.55 5 9588 50 79734745
Generalised oedema 27.88 22.55 23 9570 23686 79711109
Headache 27.53 22.55 23 9570 653749 79081046
Porphyria 26.91 22.55 6 9587 202 79734593
Status epilepticus 26.79 22.55 23 9570 25018 79709777
Renal failure 26.60 22.55 68 9525 200900 79533895
Hallucinations, mixed 26.40 22.55 14 9579 6885 79727910
Dizziness 25.43 22.55 16 9577 526425 79208370
Bicytopenia 25.31 22.55 12 9581 4658 79730137
Cutaneous T-cell lymphoma 24.59 22.55 10 9583 2693 79732102
Blood phosphorus decreased 24.02 22.55 13 9580 6655 79728140
Somnolence 23.88 22.55 73 9520 238908 79495887
Granulomatous liver disease 23.44 22.55 8 9585 1325 79733470
Target skin lesion 23.14 22.55 5 9588 145 79734650
Respiratory gas exchange disorder 22.68 22.55 7 9586 844 79733951

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC N02BG06 NERVOUS SYSTEM
ANALGESICS
OTHER ANALGESICS AND ANTIPYRETICS
Other analgesics and antipyretics
MeSH PA D000700 Analgesics
MeSH PA D018712 Analgesics, Non-Narcotic
MeSH PA D002491 Central Nervous System Agents
MeSH PA D018373 Peripheral Nervous System Agents
MeSH PA D018689 Sensory System Agents
CHEBI has role CHEBI:35640 adrenergic uptake inhibitors
CHEBI has role CHEBI:50949 SSRI
CHEBI has role CHEBI:51039 dopamine reuptake inhibitor

Drug Use | Suggest Off label Use Form| |View source of the data|

None




๐Ÿถ Veterinary Drug Use

None

๐Ÿถ Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 7.85 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Sodium channel protein type 5 subunit alpha Ion channel WOMBAT-PK
Sodium-dependent serotonin transporter Transporter Ki 7.54 PDSP
Sodium-dependent noradrenaline transporter Transporter Ki 7.48 PDSP
5-hydroxytryptamine receptor 2A GPCR Ki 5.77 PDSP
5-hydroxytryptamine receptor 2B GPCR Ki 6.48 PDSP
5-hydroxytryptamine receptor 2C GPCR Ki 7.25 PDSP
Sodium-dependent dopamine transporter Transporter Ki 6.28 PDSP

External reference:

IDSource
N0000167217 NUI
D05133 KEGG_DRUG
C0027556 UMLSCUI
CHEBI:88316 CHEBI
CHEMBL465026 ChEMBL_ID
DB12293 DRUGBANK_ID
D009340 MESH_DESCRIPTOR_UI
4450 PUBCHEM_CID
3018 INN_ID
23327-57-3 SECONDARY_CAS_RN
4UP8060B7J UNII
4324 RXNORM
001582 NDDF
004636 NDDF
322300008 SNOMEDCT_US
350324006 SNOMEDCT_US
419768004 SNOMEDCT_US
CHEMBL1407915 ChEMBL_ID

Pharmaceutical products:

None