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 335.03 26.84 115 4919 26399 56260634
Cholestasis 329.46 26.84 114 4920 26799 56260234
Hepatic cytolysis 113.42 26.84 41 4993 10865 56276168
Acute kidney injury 108.67 26.84 120 4914 240643 56046390
Drug reaction with eosinophilia and systemic symptoms 98.69 26.84 50 4984 30254 56256779
Acute generalised exanthematous pustulosis 91.14 26.84 34 5000 9835 56277198
Thrombocytopenia 72.07 26.84 74 4960 136150 56150883
Coma 71.96 26.84 52 4982 59603 56227430
Foetal megacystis 70.43 26.84 10 5024 26 56287007
Pancreatitis acute 69.02 26.84 37 4997 25087 56261946
Drug dependence 67.04 26.84 35 4999 22498 56264535
Tonic clonic movements 63.31 26.84 16 5018 1254 56285779
Fatigue 58.50 26.84 3 5031 788549 55498484
Peripheral nerve injury 57.54 26.84 12 5022 398 56286635
Anticholinergic syndrome 56.64 26.84 16 5018 1918 56285115
Mixed liver injury 49.26 26.84 17 5017 3927 56283106
Shock haemorrhagic 48.27 26.84 21 5013 9012 56278021
Miosis 47.61 26.84 19 5015 6573 56280460
Spinal epidural haemorrhage 45.63 26.84 8 5026 102 56286931
Hyperkalaemia 41.06 26.84 35 4999 50830 56236203
Cell death 41.02 26.84 13 5021 2306 56284727
Encephalopathy 40.76 26.84 30 5004 35295 56251738
Epidural haemorrhage 38.04 26.84 7 5027 119 56286914
Eosinophilia 37.50 26.84 23 5011 20054 56266979
Metabolic acidosis 37.15 26.84 30 5004 40424 56246609
Urinary bladder rupture 36.91 26.84 7 5027 141 56286892
Hyperlactacidaemia 35.63 26.84 12 5022 2576 56284457
Granulomatous liver disease 35.24 26.84 9 5025 735 56286298
Cutaneous T-cell lymphoma 34.12 26.84 10 5024 1365 56285668
Pancreatic pseudoaneurysm 34.11 26.84 6 5028 78 56286955
Foetal heart rate abnormal 33.01 26.84 8 5026 527 56286506
Agranulocytosis 32.53 26.84 22 5012 22637 56264396
Stevens-Johnson syndrome 32.53 26.84 22 5012 22641 56264392
Drug ineffective 31.55 26.84 22 5012 918967 55368066
Naevus haemorrhage 31.54 26.84 6 5028 123 56286910
Poisoning deliberate 31.14 26.84 16 5018 9937 56277096
Blood phosphorus decreased 30.54 26.84 12 5022 3985 56283048
Prescription drug used without a prescription 30.53 26.84 10 5024 1970 56285063
Somnolence 30.04 26.84 53 4981 163360 56123673
Myoclonus 29.89 26.84 18 5016 15185 56271848
Porphyria 29.78 26.84 6 5028 167 56286866
Epidural analgesia 29.45 26.84 5 5029 52 56286981
Livedo reticularis 29.34 26.84 10 5024 2225 56284808
Autonomic nervous system imbalance 27.88 26.84 10 5024 2583 56284450

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 147.57 29.25 64 3604 21183 31672493
Hepatocellular injury 137.00 29.25 61 3607 21483 31672193
Rash maculo-papular 126.67 29.25 61 3607 25658 31668018
Cholestasis 119.04 29.25 58 3610 25017 31668659
Drug reaction with eosinophilia and systemic symptoms 117.73 29.25 61 3607 29957 31663719
Eosinophilia 84.69 29.25 45 3623 23208 31670468
Alveolar lung disease 84.23 29.25 17 3651 366 31693310
Pulmonary interstitial emphysema syndrome 80.61 29.25 17 3651 457 31693219
Confusional state 74.42 29.25 84 3584 133250 31560426
Hyperleukocytosis 63.23 29.25 18 3650 1711 31691965
Diffuse alveolar damage 59.62 29.25 18 3650 2101 31691575
Pancytopenia 55.54 29.25 59 3609 87257 31606419
Acute kidney injury 54.07 29.25 107 3561 279607 31414069
Urethral valves 53.03 29.25 11 3657 272 31693404
Mixed liver injury 49.59 29.25 16 3652 2321 31691355
Eosinophilic pneumonia 49.01 29.25 17 3651 3080 31690596
Hyperammonaemia 48.50 29.25 20 3648 5813 31687863
Oesophageal achalasia 44.81 29.25 10 3658 352 31693324
Haemolytic anaemia 41.49 29.25 21 3647 9775 31683901
Consciousness fluctuating 38.09 29.25 11 3657 1100 31692576
Toxic skin eruption 37.86 29.25 20 3648 10160 31683516
Generalised oedema 35.58 29.25 20 3648 11481 31682195
Hepatitis 34.66 29.25 25 3643 22041 31671635
Hepatic encephalopathy 32.37 29.25 20 3648 13651 31680025
Pancreatitis acute 31.35 29.25 25 3643 25575 31668101
Thrombocytopenia 30.34 29.25 57 3611 142690 31550986
Eczema 30.17 29.25 20 3648 15397 31678279

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 433.63 22.33 176 8668 45915 70873685
Cholestasis 406.87 22.33 170 8674 47702 70871898
Drug reaction with eosinophilia and systemic symptoms 199.96 22.33 111 8733 57902 70861698
Agranulocytosis 157.96 22.33 84 8760 40214 70879386
Acute kidney injury 137.60 22.33 226 8618 474398 70445202
Rash maculo-papular 122.31 22.33 77 8767 50468 70869132
Hepatic cytolysis 119.96 22.33 55 8789 19137 70900463
Eosinophilia 114.37 22.33 68 8776 40251 70879349
Acute generalised exanthematous pustulosis 98.97 22.33 45 8799 15352 70904248
Pancreatitis acute 92.46 22.33 62 8782 45162 70874438
Mixed liver injury 91.46 22.33 33 8811 6216 70913384
Thrombocytopenia 90.34 22.33 129 8715 238981 70680619
Confusional state 80.15 22.33 134 8710 284264 70635336
Pulmonary interstitial emphysema syndrome 79.47 22.33 17 8827 453 70919147
Alveolar lung disease 76.62 22.33 17 8827 539 70919061
Fatigue 74.87 22.33 8 8836 824311 70095289
Coma 73.89 22.33 73 8771 91771 70827829
Tonic clonic movements 63.35 22.33 19 8825 2008 70917592
Drug dependence 59.59 22.33 44 8800 37277 70882323
Hyperleukocytosis 57.59 22.33 18 8826 2183 70917417
Toxic skin eruption 57.12 22.33 34 8810 20128 70899472
Hepatitis 56.32 22.33 48 8796 49932 70869668
Encephalopathy 53.29 22.33 51 8793 61610 70857990
Pancytopenia 50.43 22.33 77 8767 151030 70768570
Diffuse alveolar damage 50.11 22.33 18 8826 3345 70916255
Peripheral nerve injury 47.65 22.33 12 8832 661 70918939
Haemolytic anaemia 46.74 22.33 28 8816 16766 70902834
Anticholinergic syndrome 44.59 22.33 16 8828 2964 70916636
Febrile bone marrow aplasia 44.14 22.33 24 8820 11967 70907633
Miosis 43.15 22.33 25 8819 14076 70905524
Drug ineffective 42.77 22.33 33 8811 939719 69979881
Neutropenia 40.47 22.33 95 8749 257061 70662539
Eosinophilic pneumonia 40.15 22.33 17 8827 4888 70914712
Hyperammonaemia 39 22.33 21 8823 10272 70909328
Oesophageal achalasia 37.21 22.33 10 8834 711 70918889
Hyperthermia 36.82 22.33 24 8820 16647 70902953
Anaphylactic shock 36.18 22.33 31 8813 32459 70887141
Foetal heart rate abnormal 35.86 22.33 8 8836 260 70919340
Cell death 35.86 22.33 15 8829 4185 70915415
Hyperbilirubinaemia 34.66 22.33 26 8818 22542 70897058
Spinal epidural haemorrhage 34.31 22.33 7 8837 147 70919453
Poisoning deliberate 33.91 22.33 23 8821 17037 70902563
Gamma-glutamyltransferase increased 33.00 22.33 36 8808 50649 70868951
Consciousness fluctuating 32.19 22.33 11 8833 1765 70917835
Pancreatic pseudoaneurysm 32.12 22.33 6 8838 78 70919522
Epidural haemorrhage 31.76 22.33 7 8837 215 70919385
Prothrombin time ratio decreased 31.73 22.33 9 8835 782 70918818
Myoclonus 31.09 22.33 26 8818 26329 70893271
Pneumonia 30.99 22.33 18 8826 596214 70323386
Hepatic encephalopathy 30.71 22.33 24 8820 22094 70897506
Shock haemorrhagic 30.37 22.33 22 8822 18084 70901516
Urinary retention 30.26 22.33 35 8809 52485 70867115
Hyperlactacidaemia 30.00 22.33 14 8830 5058 70914542
Transaminases increased 29.93 22.33 33 8811 46985 70872615
Naevus haemorrhage 29.55 22.33 6 8838 123 70919477
Generalised oedema 28.94 22.33 23 8821 21685 70897915
Metabolic acidosis 27.81 22.33 40 8804 74306 70845294
Epidural analgesia 27.62 22.33 5 8839 54 70919546
Hallucination 27.03 22.33 40 8804 76220 70843380
Hallucinations, mixed 26.99 22.33 14 8830 6348 70913252
Porphyria 26.58 22.33 6 8838 206 70919394
Hallucination, visual 24.83 22.33 24 8820 29313 70890287
Cutaneous T-cell lymphoma 24.80 22.33 10 8834 2543 70917057
Blood phosphorus decreased 24.73 22.33 13 8831 6056 70913544
Granulomatous liver disease 23.78 22.33 8 8836 1224 70918376
Symmetrical drug-related intertriginous and flexural exanthema 23.70 22.33 7 8837 701 70918899
Target skin lesion 23.56 22.33 5 8839 128 70919472
Hepatitis acute 23.49 22.33 17 8827 13945 70905655
Prescription drug used without a prescription 23.25 22.33 10 8834 2987 70916613
Respiratory gas exchange disorder 23.14 22.33 7 8837 761 70918839
Dizziness 22.73 22.33 15 8829 464126 70455474
Renal failure 22.59 22.33 63 8781 189007 70730593
Stevens-Johnson syndrome 22.50 22.33 25 8819 35882 70883718

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