nimesulide 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | PK/Tox | Related Drugs | BioActivity |

Stem definitionDrug idCAS RN
nicotinic acid or nicotinoyl alcohol derivatives 1935 51803-78-2

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • nimesulide
  • mesulide
  • mesulid
  • nimsulid
  • sulidene
  • sulide
  • sulidan
  • Molecular weight: 308.31
  • Formula: C13H12N2O5S
  • CLOGP: 2.91
  • LIPINSKI: 0
  • HAC: 7
  • HDO: 1
  • TPSA: 101.22
  • ALOGS: -4.23
  • ROTB: 4

Drug dosage:

DoseUnitRoute
0.20 g O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 2 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 0.01 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 2 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 9.27 µM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 60 %

Predicted pharmacokinetic/toxicological properties (PK-AZ):

PropertyDescriptionValueUnitConfidenceSimilarity
azlogd74 LogD at pH 7.4 1.431 High 1
caco2-efflux Caco-2 efflux ratio (BA/AB) 0.908 High 1
caco2-intrinsic-papp Caco-2 intrinsic apparent permeability 79.799 10^-6 cm/s High 1
dh-clint Dog hepatocyte intrinsic clearance 8.650 uL/min/10^6 cells High 1
dppb Dog plasma protein binding (% unbound) 1.460 % High 1
fcs-ppb Fetal calf serum protein binding (% unbound) 2.920 % High 1
herg hERG pIC50 4.570 pIC50 High 1
hh-clint Human hepatocyte intrinsic clearance 5.534 uL/min/10^6 cells High 1
hlm-clint Human liver microsomal intrinsic clearance 5.093 uL/min/mg protein High 1
hppb Human plasma protein binding (% unbound) 0.880 % High 1
kinase-safety-class ACVR2A,ACVR2B,AURKA,AXL,BRAF,BTK,CAMK2D,CDK5,CDK9,DDR1,DYRK1B,EGFR,EIF2AK3,ERBB2,GRK2,GSK3B,ITK,JAK2,JAK3,MAP2K6,MAP3K21,MAP3K7,MAPK10,MAPK7,MAPK8,MAPK9,MAPKAPK2,MAPKAPK5,MET,NTRK2,PDK1,PDK2,PDK4,PDPK1,PIK3CB,PIK3CD,PIK3CG,PIM2,PRKDC,SIK2,STK33,SYK,TEK,TTK,ZAP70 45
kinase-selectivity-class AXL,DYRK1B,GRK2,MAP2K6,MAPK7,MAPK8,STK33,TEK,TTK 9
mdck-mdr1-efflux MDCK-MDR1 efflux ratio 2.291 High 1
mh-clint Mouse hepatocyte intrinsic clearance 28.119 High 1
mppb Mouse plasma protein binding (% unbound) 2.430 High 1
nih-mdck-mdr1-efflux NIH MDCK-MDR1 efflux ratio 2.138 High 1
pfas-class PFAS structural alert (1 = True, 0 = False) 0
pppb Pig plasma protein binding (% unbound) 1.560 % High 1
rh-clint Rat hepatocyte intrinsic clearance 11.350 uL/min/10^6 cells High 1
rh-fuinc Rat hepatocyte fraction unbound in incubation 57.770 % High 1
rppb Rat plasma protein binding (% unbound) 0.820 % High 1
solubility-dd Solubility at pH 7.4 in DMSO 566.239 uM High 1

Approvals:

DateAgencyCompanyOrphan
Jan. 1, 1985 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
Ductus arteriosus stenosis foetal 121.70 22.90 18 2925 219 90625285
Renal failure neonatal 115.94 22.90 17 2926 194 90625310
Drug abuse 108.40 22.90 53 2890 82294 90543210
Neonatal respiratory acidosis 96.50 22.90 15 2928 259 90625245
Cyanosis neonatal 82.38 22.90 14 2929 429 90625075
Bradycardia neonatal 75.77 22.90 15 2928 1078 90624426
Amniotic cavity disorder 73.49 22.90 10 2933 63 90625441
Specific gravity urine abnormal 71.40 22.90 10 2933 80 90625424
Neonatal respiratory distress syndrome 70.34 22.90 17 2926 3084 90622420
Ductus arteriosus premature closure 55.91 22.90 10 2933 414 90625090
Suicide attempt 52.85 22.90 32 2911 75367 90550137
Contraindication to medical treatment 47.87 22.90 10 2933 939 90624565
Oligohydramnios 47.69 22.90 15 2928 7186 90618318
Polyuria 46.66 22.90 16 2927 10024 90615480
Intentional self-injury 44.98 22.90 21 2922 29313 90596191
Premature baby 44.90 22.90 20 2923 25057 90600447
Gastritis erosive 40.31 22.90 13 2930 6742 90618762
Hepatocellular injury 39.11 22.90 19 2924 28939 90596565
Maximal voluntary ventilation abnormal 37.72 22.90 5 2938 25 90625479
Atrioventricular block complete 35.56 22.90 13 2930 9798 90615706
Emphysema 32.85 22.90 13 2930 12142 90613362
Intestinal haemorrhage 32.54 22.90 10 2933 4437 90621067
Tonsillar exudate 30.91 22.90 4 2939 16 90625488
Duplicate therapy error 30.79 22.90 5 2938 115 90625389
Intentional overdose 30.75 22.90 25 2918 93809 90531695
Abdominal pain upper 27.38 22.90 43 2900 332631 90292873
Ocular hypertension 27.04 22.90 7 2936 1673 90623831
Foetal exposure during pregnancy 26.94 22.90 17 2926 42958 90582546
Creatinine urine increased 26.82 22.90 5 2938 261 90625243
Diabetic metabolic decompensation 25.99 22.90 7 2936 1950 90623554
Jaundice 25.89 22.90 15 2928 32502 90593002
Complicated appendicitis 24.09 22.90 4 2939 106 90625398
Product dispensing issue 23.98 22.90 5 2938 465 90625039
Bladder disorder 23.90 22.90 10 2933 10762 90614742
Respiratory acidosis 23.05 22.90 9 2934 8110 90617394

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
Polyneuropathy in malignant disease 88.05 32.03 15 1760 361 42619199
Allodynia 66.29 32.03 14 1761 1080 42618480
Hyperaesthesia 59.47 32.03 18 1757 5934 42613626
Body mass index abnormal 55.10 32.03 9 1766 166 42619394
Quality of life decreased 52.60 32.03 16 1759 5360 42614200
Ligament calcification 52.22 32.03 9 1766 232 42619328
Rash maculovesicular 49.19 32.03 7 1768 48 42619512
Confabulation 48.65 32.03 8 1767 154 42619406
Metastases to lung 47.96 32.03 18 1757 11406 42608154
Dermatitis allergic 45.43 32.03 16 1759 8467 42611093
Face oedema 44.83 32.03 18 1757 13648 42605912
Drug abuse 44.62 32.03 36 1739 104735 42514825
Lip erythema 44.22 32.03 7 1768 105 42619455
Nasal mucosal disorder 42.55 32.03 7 1768 135 42619425
Negativism 40.83 32.03 8 1767 423 42619137
Chronic kidney disease 40.67 32.03 25 1750 47216 42572344
Ankylosing spondylitis 36.61 32.03 13 1762 7043 42612517
Palmoplantar pustulosis 33.83 32.03 7 1768 488 42619072
Metastases to bone 33.55 32.03 15 1760 14794 42604766
Sacroiliitis 33.33 32.03 9 1766 1973 42617587
Spinal pain 33.31 32.03 12 1763 6770 42612790
Polyneuropathy 33.24 32.03 16 1759 18645 42600915
Enanthema 32.09 32.03 7 1768 628 42618932

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
Drug abuse 118.91 21.05 85 5273 177326 110406615
Ductus arteriosus stenosis foetal 110.10 21.05 16 5342 109 110583832
Renal failure neonatal 99.06 21.05 14 5344 76 110583865
Neonatal respiratory acidosis 93.57 21.05 13 5345 61 110583880
Bradycardia neonatal 90.60 21.05 13 5345 80 110583861
Cyanosis neonatal 85.09 21.05 12 5346 64 110583877
Polyneuropathy in malignant disease 81.44 21.05 15 5343 486 110583455
Neonatal respiratory distress syndrome 71.91 21.05 13 5345 379 110583562
Amaurosis fugax 63.00 21.05 16 5342 2374 110581567
Amniotic cavity disorder 55.92 21.05 8 5350 48 110583893
Allodynia 55.17 21.05 14 5344 2069 110581872
Specific gravity urine abnormal 51.87 21.05 8 5350 85 110583856
Ligament calcification 50.81 21.05 9 5349 233 110583708
Intentional self-injury 50.51 21.05 28 5330 37401 110546540
Gastritis erosive 47.86 21.05 19 5339 11981 110571960
Rash maculovesicular 47.75 21.05 7 5351 51 110583890
Premature baby 47.59 21.05 15 5343 4840 110579101
Ocular discomfort 42.93 21.05 16 5342 8517 110575424
Oligohydramnios 41.91 21.05 13 5345 3981 110579960
Urinary tract disorder 40.91 21.05 14 5344 5830 110578111
Hyperaesthesia 40.84 21.05 18 5340 14709 110569232
Intentional overdose 39.71 21.05 40 5318 132461 110451480
Face oedema 39.66 21.05 23 5335 33446 110550495
Body mass index abnormal 38.75 21.05 9 5349 919 110583022
Confabulation 38.10 21.05 8 5350 513 110583428
Altered state of consciousness 37.11 21.05 27 5331 57599 110526342
Generalised oedema 36.12 21.05 21 5337 30683 110553258
Metastases to lung 35.98 21.05 19 5339 23044 110560897
Haemorrhagic stroke 35.51 21.05 16 5342 13773 110570168
Contraindication to medical treatment 35.31 21.05 9 5349 1354 110582587
Polyneuropathy 35.31 21.05 21 5337 31991 110551950
Quality of life decreased 35.09 21.05 16 5342 14153 110569788
Maximal voluntary ventilation abnormal 34.81 21.05 5 5353 31 110583910
Abdominal pain upper 34.34 21.05 61 5297 349050 110234891
Suicide attempt 34.29 21.05 33 5325 103361 110480580
Negativism 33.49 21.05 8 5350 921 110583020
Lip erythema 32.37 21.05 7 5351 517 110583424
Dermatitis allergic 31.37 21.05 17 5341 21707 110562234
Sacroiliitis 31.27 21.05 11 5347 4967 110578974
Drug interaction 30.85 21.05 72 5286 500111 110083830
Erosive duodenitis 30.68 21.05 9 5349 2282 110581659
Intestinal haemorrhage 30.59 21.05 12 5346 7329 110576612
Haematemesis 29.93 21.05 24 5334 59084 110524857
Low birth weight baby 28.96 21.05 7 5351 848 110583093
Palmoplantar pustulosis 27.96 21.05 7 5351 979 110582962
Mixed liver injury 27.91 21.05 13 5345 12066 110571875
Head discomfort 27.80 21.05 15 5343 18985 110564956
Tonsillar exudate 27.68 21.05 4 5354 26 110583915
Enanthema 26.99 21.05 7 5351 1127 110582814
Foetal exposure during pregnancy 26.88 21.05 11 5347 7494 110576447
Hepatocellular injury 26.57 21.05 21 5337 50621 110533320
Chronic kidney disease 26.53 21.05 25 5333 76266 110507675
Polyuria 25.94 21.05 14 5344 17724 110566217
Oral mucosa erosion 25.82 21.05 8 5350 2440 110581501
Metastases to bone 25.59 21.05 17 5341 31355 110552586
Spinal pain 25.38 21.05 14 5344 18501 110565440
Drug dependence 24.66 21.05 20 5338 50000 110533941
Photophobia 23.56 21.05 15 5343 25756 110558185
Nasal mucosal disorder 23.48 21.05 7 5351 1876 110582065
Genital ulceration 23.15 21.05 7 5351 1968 110581973
Melaena 22.89 21.05 22 5336 68735 110515206
Eye pain 22.55 21.05 19 5339 50080 110533861
Duplicate therapy error 22.32 21.05 5 5353 434 110583507
Atrioventricular block complete 21.69 21.05 13 5345 20069 110563872
Creatinine urine increased 21.42 21.05 5 5353 521 110583420
Blindness 21.08 21.05 16 5342 36343 110547598
Speech disorder 21.07 21.05 20 5338 61549 110522392

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC M01AX17 MUSCULO-SKELETAL SYSTEM
ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS
ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS, NON-STEROIDS
Other antiinflammatory and antirheumatic agents, non-steroids
ATC M02AA26 MUSCULO-SKELETAL SYSTEM
TOPICAL PRODUCTS FOR JOINT AND MUSCULAR PAIN
TOPICAL PRODUCTS FOR JOINT AND MUSCULAR PAIN
Antiinflammatory preparations, non-steroids for topical use
MeSH PA D000700 Analgesics
MeSH PA D000893 Anti-Inflammatory Agents
MeSH PA D000894 Anti-Inflammatory Agents, Non-Steroidal
MeSH PA D004791 Enzyme Inhibitors
MeSH PA D016861 Cyclooxygenase Inhibitors
MeSH PA D018373 Peripheral Nervous System Agents
MeSH PA D018501 Antirheumatic Agents
MeSH PA D018689 Sensory System Agents
MeSH PA D018712 Analgesics, Non-Narcotic
CHEBI has role CHEBI:35475 non-steroidal anti-inflammatory drug
CHEBI has role CHEBI:35480 analgesic
CHEBI has role CHEBI:35610 antineoplastic agent
CHEBI has role CHEBI:50629 cyclooxygenase 2 inhibitor

Related Drugs by ATC class:

M01AX Other antiinflammatory and antirheumatic agents, non-steroids 13 drugs
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M02AA Antiinflammatory preparations, non-steroids for topical use 28 drugs
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Drug Use | Suggest Off label Use Form| |View source of the data|

None




🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 6.03 acidic

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
Prostaglandin G/H synthase 2 Enzyme IC50 5.91 WOMBAT-PK
Prostaglandin G/H synthase 1 Enzyme IC50 5.42 CHEMBL
Sodium-dependent dopamine transporter Transporter Ki 4.93 DRUG MATRIX
Aromatase Enzyme IC50 4.57 WOMBAT-PK
cAMP-specific 3',5'-cyclic phosphodiesterase 4A Enzyme IC50 5.70 WOMBAT-PK
Myeloperoxidase Enzyme IC50 5.68 CHEMBL
Interstitial collagenase Enzyme IC50 4.63 DRUG MATRIX
Prostaglandin G/H synthase 1 Enzyme IC50 5.21 CHEMBL
Prostaglandin G/H synthase 2 Enzyme IC50 6.40 CHEMBL
Sodium-dependent neutral amino acid transporter B(0)AT1 Transporter INHIBITOR IC50 4.64 IUPHAR
Dipeptidyl peptidase 3 Enzyme Ki 4.16 CHEMBL

External reference:

IDSource
D01049 KEGG_DRUG
C0132515 UMLSCUI
CHEBI:44445 CHEBI
NIM PDB_CHEM_ID
CHEMBL56367 ChEMBL_ID
DB04743 DRUGBANK_ID
C012655 MESH_SUPPLEMENTAL_RECORD_UI
4495 PUBCHEM_CID
7401 IUPHAR_LIGAND_ID
4885 INN_ID
V4TKW1454M UNII
53694 RXNORM
004182 NDDF
703479000 SNOMEDCT_US
703480002 SNOMEDCT_US
V4TKW1454M INXIGHT DRUGS

Pharmaceutical products:

None