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 327.78 25.85 114 4654 25833 50574523
Cholestasis 299.35 25.85 106 4662 25295 50575061
Acute kidney injury 107.18 25.85 119 4649 227939 50372417
Drug reaction with eosinophilia and systemic symptoms 99.26 25.85 50 4718 28374 50571982
Foetal megacystis 69.90 25.85 10 4758 26 50600330
Drug dependence 69.66 25.85 35 4733 19724 50580632
Coma 69.48 25.85 51 4717 56828 50543528
Tonic clonic movements 62.90 25.85 16 4752 1221 50599135
Pancreatitis acute 60.77 25.85 34 4734 23778 50576578
Acute generalised exanthematous pustulosis 60.67 25.85 25 4743 8913 50591443
Hepatic cytolysis 59.57 25.85 24 4744 8079 50592277
Peripheral nerve injury 57.15 25.85 12 4756 390 50599966
Anticholinergic syndrome 56.99 25.85 16 4752 1779 50598577
Thrombocytopenia 56.98 25.85 65 4703 127608 50472748
Fatigue 54.80 25.85 3 4765 707598 49892758
Shock haemorrhagic 48.82 25.85 21 4747 8323 50592033
Miosis 47.45 25.85 19 4749 6291 50594065
Mixed liver injury 46.69 25.85 16 4752 3435 50596921
Spinal epidural haemorrhage 45.21 25.85 8 4760 102 50600254
Hyperkalaemia 41.18 25.85 35 4733 48054 50552302
Encephalopathy 40.62 25.85 30 4738 33681 50566675
Eosinophilia 37.95 25.85 23 4745 18629 50581727
Epidural haemorrhage 37.67 25.85 7 4761 119 50600237
Urinary bladder rupture 36.99 25.85 7 4761 132 50600224
Hyperlactacidaemia 35.74 25.85 12 4756 2421 50597935
Granulomatous liver disease 34.79 25.85 9 4759 734 50599622
Metabolic acidosis 34.77 25.85 29 4739 38796 50561560
Cutaneous T-cell lymphoma 34.43 25.85 10 4758 1254 50599102
Poisoning deliberate 33.83 25.85 16 4752 7896 50592460
Pancreatic pseudoaneurysm 33.80 25.85 6 4762 78 50600278
Cell death 32.83 25.85 11 4757 2204 50598152
Foetal heart rate abnormal 32.73 25.85 8 4760 518 50599838
Stevens-Johnson syndrome 32.31 25.85 22 4746 21730 50578626
Prescription drug used without a prescription 31.51 25.85 10 4758 1690 50598666
Blood phosphorus decreased 30.55 25.85 12 4756 3777 50596579
Somnolence 30.08 25.85 53 4715 154932 50445424
Myoclonus 29.84 25.85 18 4750 14452 50585904
Porphyria 29.58 25.85 6 4762 164 50600192
Epidural analgesia 29.55 25.85 5 4763 48 50600308
Drug ineffective 29.19 25.85 21 4747 819312 49781044
Livedo reticularis 29.11 25.85 10 4758 2162 50598194
Autonomic nervous system imbalance 28.19 25.85 10 4758 2375 50597981
Porphyria acute 28.10 25.85 7 4761 490 50599866
Agranulocytosis 27.92 25.85 20 4748 21401 50578955
Hepatitis 27.14 25.85 23 4745 31430 50568926
Shock 26.27 25.85 19 4749 20631 50579725
Folate deficiency 26.19 25.85 9 4759 1946 50598410
Naevus haemorrhage 26.00 25.85 5 4763 103 50600253

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 150.96 28.76 64 3322 20276 29550865
Hepatocellular injury 138.49 28.76 61 3325 21182 29549959
Cholestasis 114.15 28.76 55 3331 23407 29547734
Rash maculo-papular 106.38 28.76 53 3333 24236 29546905
Drug reaction with eosinophilia and systemic symptoms 99.27 28.76 53 3333 27939 29543202
Eosinophilia 87.21 28.76 45 3341 22116 29549025
Alveolar lung disease 85.04 28.76 17 3369 352 29570789
Pulmonary interstitial emphysema syndrome 81.09 28.76 17 3369 449 29570692
Confusional state 76.35 28.76 83 3303 127794 29443347
Hyperleukocytosis 64.42 28.76 18 3368 1617 29569524
Diffuse alveolar damage 60.46 28.76 18 3368 2025 29569116
Pancytopenia 58.50 28.76 59 3327 83109 29488032
Urethral valves 53.15 28.76 11 3375 272 29570869
Acute kidney injury 52.71 28.76 102 3284 265165 29305976
Eosinophilic pneumonia 50.60 28.76 17 3369 2829 29568312
Hyperammonaemia 49.29 28.76 20 3366 5643 29565498
Oesophageal achalasia 45.78 28.76 10 3376 322 29570819
Haemolytic anaemia 42.49 28.76 21 3365 9398 29561743
Toxic skin eruption 38.87 28.76 20 3366 9737 29561404
Generalised oedema 36.33 28.76 20 3366 11145 29559996
Hepatitis 36.26 28.76 25 3361 20758 29550383
Hepatic encephalopathy 33.45 28.76 20 3366 13015 29558126
Pancreatitis acute 32.67 28.76 25 3361 24360 29546781
Eczema 32.36 28.76 20 3366 13806 29557335
Thrombocytopenia 31.85 28.76 56 3330 134767 29436374
Mixed liver injury 31.57 28.76 11 3375 2040 29569101
Neutropenia 31.49 28.76 55 3331 131656 29439485
Cholestatic liver injury 29.62 28.76 10 3376 1687 29569454

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 428.86 23.55 175 8090 45060 64445407
Cholestasis 376.01 23.55 159 8106 44713 64445754
Drug reaction with eosinophilia and systemic symptoms 182.23 23.55 103 8162 54114 64436353
Agranulocytosis 154.31 23.55 82 8183 38147 64452320
Acute kidney injury 134.14 23.55 220 8045 449020 64041447
Eosinophilia 116.27 23.55 68 8197 38008 64452459
Rash maculo-papular 105.49 23.55 69 8196 46957 64443510
Pancreatitis acute 86.75 23.55 59 8206 42796 64447671
Thrombocytopenia 79.51 23.55 119 8146 223682 64266785
Pulmonary interstitial emphysema syndrome 79.26 23.55 17 8248 446 64490021
Confusional state 77.73 23.55 128 8137 261016 64229451
Alveolar lung disease 76.75 23.55 17 8248 520 64489947
Coma 73.25 23.55 72 8193 87543 64402924
Mixed liver injury 72.27 23.55 27 8238 5454 64485013
Fatigue 68.54 23.55 8 8257 748722 63741745
Tonic clonic movements 63.19 23.55 19 8246 1970 64488497
Drug dependence 63.01 23.55 44 8221 33268 64457199
Hepatic cytolysis 61.95 23.55 32 8233 14017 64476450
Hepatitis 59.05 23.55 48 8217 45534 64444933
Hyperleukocytosis 58.46 23.55 18 8247 2022 64488445
Acute generalised exanthematous pustulosis 56.23 23.55 30 8235 14028 64476439
Encephalopathy 54.16 23.55 51 8214 58768 64431699
Toxic skin eruption 52.48 23.55 32 8233 19252 64471215
Pancytopenia 51.95 23.55 77 8188 143232 64347235
Diffuse alveolar damage 50.31 23.55 18 8247 3217 64487250
Peripheral nerve injury 48.00 23.55 12 8253 624 64489843
Haemolytic anaemia 47.20 23.55 28 8237 16025 64474442
Anticholinergic syndrome 45.89 23.55 16 8249 2653 64487814
Febrile bone marrow aplasia 42.16 23.55 23 8242 11232 64479235
Eosinophilic pneumonia 40.84 23.55 17 8248 4560 64485907
Hyperammonaemia 39.22 23.55 21 8244 9883 64480584
Neutropenia 38.79 23.55 91 8174 239533 64250934
Oesophageal achalasia 37.38 23.55 10 8255 680 64489787
Drug ineffective 37.19 23.55 32 8233 840215 63650252
Foetal heart rate abnormal 36.01 23.55 8 8257 248 64490219
Hyperbilirubinaemia 35.47 23.55 26 8239 21179 64469288
Hyperthermia 35.28 23.55 23 8242 15527 64474940
Anaphylactic shock 35.24 23.55 30 8235 30298 64460169
Spinal epidural haemorrhage 34.12 23.55 7 8258 147 64490320
Epidural haemorrhage 33.03 23.55 7 8258 173 64490294
Pancreatic pseudoaneurysm 31.95 23.55 6 8259 78 64490389
Gamma-glutamyltransferase increased 31.75 23.55 35 8230 48475 64441992
Prothrombin time ratio decreased 31.69 23.55 9 8256 764 64489703
Urinary retention 31.35 23.55 35 8230 49166 64441301
Shock haemorrhagic 31.32 23.55 22 8243 16769 64473698
Hepatic encephalopathy 31.17 23.55 24 8241 21042 64469425
Transaminases increased 30.63 23.55 33 8232 44561 64445906
Hyperlactacidaemia 30.26 23.55 14 8251 4830 64485637
Cell death 29.39 23.55 13 8252 4041 64486426
Generalised oedema 29.21 23.55 23 8242 20830 64469637
Pneumonia 29.00 23.55 18 8247 559558 63930909
Miosis 28.58 23.55 19 8246 13247 64477220
Poisoning deliberate 28.33 23.55 19 8246 13439 64477028
Epidural analgesia 27.83 23.55 5 8260 50 64490417
Myoclonus 27.46 23.55 24 8241 25094 64465373
Porphyria 26.62 23.55 6 8259 199 64490268
Metabolic acidosis 25.49 23.55 38 8227 70920 64419547
Cutaneous T-cell lymphoma 25.33 23.55 10 8255 2342 64488125
Blood phosphorus decreased 25.16 23.55 13 8252 5692 64484775
Pain 24.52 23.55 21 8244 553490 63936977
Naevus haemorrhage 24.46 23.55 5 8260 103 64490364
Hallucinations, mixed 24.43 23.55 13 8252 6039 64484428
Symmetrical drug-related intertriginous and flexural exanthema 24.42 23.55 7 8258 614 64489853
Prescription drug used without a prescription 24.36 23.55 10 8255 2590 64487877
Hepatitis acute 23.72 23.55 17 8248 13372 64477095
Granulomatous liver disease 23.63 23.55 8 8257 1214 64489253
Headache 23.56 23.55 20 8245 529447 63961020

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

Pharmaceutical products:

None