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

Stem definitionDrug idCAS RN
anti-inflammatory agents, ibufenac derivatives 2534 38194-50-2

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • MK231
  • MK-231
  • MK 231
  • clinoril
  • sulindac
A sulfinylindene derivative prodrug whose sulfinyl moiety is converted in vivo to an active NSAID analgesic. Specifically, the prodrug is converted by liver enzymes to a sulfide which is excreted in the bile and then reabsorbed from the intestine. This helps to maintain constant blood levels with reduced gastrointestinal side effects.
  • Molecular weight: 356.41
  • Formula: C20H17FO3S
  • CLOGP: 3.16
  • LIPINSKI: 0
  • HAC: 3
  • HDO: 1
  • TPSA: 54.37
  • ALOGS: -4.15
  • ROTB: 4
  • Status: OFP
    • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
0.40 g O
0.40 g P
0.40 g R

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 2 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 0.00 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 1 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 16.03 µM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 88 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H

Predicted pharmacokinetic/toxicological properties (PK-AZ):

PropertyDescriptionValueUnitConfidenceSimilarity
azlogd74 LogD at pH 7.4 0.356 Moderate 0.72
caco2-efflux Caco-2 efflux ratio (BA/AB) 6.966 Moderate 0.72
caco2-intrinsic-papp Caco-2 intrinsic apparent permeability 7.464 10^-6 cm/s Moderate 0.72
dh-clint Dog hepatocyte intrinsic clearance 4.603 uL/min/10^6 cells Moderate 0.72
dppb Dog plasma protein binding (% unbound) 1.680 % Moderate 0.72
fcs-ppb Fetal calf serum protein binding (% unbound) 5.020 % Moderate 0.72
herg hERG pIC50 4.448 pIC50 Moderate 0.72
hh-clint Human hepatocyte intrinsic clearance 3.006 uL/min/10^6 cells Moderate 0.72
hlm-clint Human liver microsomal intrinsic clearance 3.327 uL/min/mg protein Moderate 0.72
hppb Human plasma protein binding (% unbound) 1.400 % Moderate 0.72
kinase-safety-class ACVR2B,AURKA,AXL,BRAF,BTK,CAMK2D,CDK5,CDK9,DYRK1B,EGFR,EIF2AK3,ERBB2,GRK2,ITK,MAP2K6,MAPK10,MAPK7,PDK1,PDK2,PDK4,PIK3CA,PIK3CB,PIK3CD,PIK3CG,PRKDC,TEK,TGFBR1 27
kinase-selectivity-class ACVR2B,AXL,BRAF,CDK9,EIF2AK3,GRK2,MAP2K6,MAPK7,PRKDC,STK33,TEK,TGFBR1,TTK,ZAP70 14
mdck-mdr1-efflux MDCK-MDR1 efflux ratio 4.055 Moderate 0.72
mh-clint Mouse hepatocyte intrinsic clearance 7.311 Moderate 0.72
mppb Mouse plasma protein binding (% unbound) 2.330 Moderate 0.72
nih-mdck-mdr1-efflux NIH MDCK-MDR1 efflux ratio 3.342 Moderate 0.72
pfas-class PFAS structural alert (1 = True, 0 = False) 0
pld-class Phospholipidosis risk class (1 = positive, 0 = negative) 0 High 1
pppb Pig plasma protein binding (% unbound) 2.940 % Moderate 0.72
rh-clint Rat hepatocyte intrinsic clearance 4.808 uL/min/10^6 cells Moderate 0.72
rh-fuinc Rat hepatocyte fraction unbound in incubation 67.480 % Moderate 0.72
rppb Rat plasma protein binding (% unbound) 0.790 % Moderate 0.72
solubility-dd Solubility at pH 7.4 in DMSO 901.571 uM Moderate 0.72

Approvals:

DateAgencyCompanyOrphan
Sept. 27, 1978 FDA MERCK

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
Drug hypersensitivity 102.06 19.50 95 2644 463514 90162194
Hangover 66.46 19.50 15 2724 2174 90623534
Musculoskeletal discomfort 46.29 19.50 19 2720 20972 90604736
Musculoskeletal chest pain 37.57 19.50 17 2722 23733 90601975
Skin disorder 33.32 19.50 18 2721 36688 90589020
Accidental exposure to product 28.29 19.50 17 2722 42349 90583359
Neck pain 28.08 19.50 25 2714 113938 90511770
Inflammatory pain 25.47 19.50 6 2733 1047 90624661
Crystal nephropathy 24.94 19.50 6 2733 1145 90624563
Psoriasis 20.90 19.50 24 2715 147730 90477978

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
Gastric haemorrhage 31.22 22.64 11 976 10504 42609844

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 hypersensitivity 74.60 18.94 77 3042 454013 110132167
Hangover 65.50 18.94 15 3104 2487 110583693
Musculoskeletal discomfort 45.45 18.94 19 3100 23519 110562661
Musculoskeletal chest pain 32.51 18.94 16 3103 28831 110557349
Skin disorder 29.17 18.94 17 3102 42896 110543284
Accidental exposure to product 26.77 18.94 17 3102 49991 110536189
Gastric haemorrhage 24.66 18.94 11 3108 15904 110570276
Neck pain 24.02 18.94 23 3096 123107 110463073
Inflammatory pain 23.57 18.94 6 3113 1547 110584633
Crystal nephropathy 22.51 18.94 6 3113 1850 110584330
Pain in extremity 19.94 18.94 43 3076 487075 110099105
Psoriasis 19.79 18.94 22 3097 139971 110446209

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC M01AB02 MUSCULO-SKELETAL SYSTEM
ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS
ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS, NON-STEROIDS
Acetic acid derivatives and related substances
FDA CS M0001335 Anti-Inflammatory Agents, Non-Steroidal
FDA MoA N0000000160 Cyclooxygenase Inhibitors
MeSH PA D000700 Analgesics
MeSH PA D000893 Anti-Inflammatory Agents
MeSH PA D000894 Anti-Inflammatory Agents, Non-Steroidal
MeSH PA D000970 Antineoplastic Agents
MeSH PA D004791 Enzyme Inhibitors
MeSH PA D016861 Cyclooxygenase Inhibitors
MeSH PA D018501 Antirheumatic Agents
MeSH PA D018689 Sensory System Agents
MeSH PA D018712 Analgesics, Non-Narcotic
FDA EPC N0000175722 Nonsteroidal Anti-inflammatory Drug
CHEBI has role CHEBI:35475 non-steroidal anti-inflammatory drug
CHEBI has role CHEBI:35480 analgesic
CHEBI has role CHEBI:35481 non-narcotic analgesic
CHEBI has role CHEBI:35493 antipyretic
CHEBI has role CHEBI:35544 EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor
CHEBI has role CHEBI:35610 antineoplastic agent
CHEBI has role CHEBI:50266 prodrug
CHEBI has role CHEBI:66993 tocolytic agent
CHEBI has role CHEBI:68495 apoptosis inducer

Related Drugs by ATC class:

M01AB Acetic acid derivatives and related substances 16 drugs
aceclofenacacemetacinalclofenacbufexamacbumadizonediclofenacdifenpiramideetodolacfentiazacindomethacinketorolaclonazolac show all 16 →

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

DiseaseRelationSNOMED_IDDOID
Ankylosing spondylitis indication 9631008 DOID:7147
Tendinitis indication 34840004 DOID:971
Articular gout indication 48440001 DOID:13189
Rheumatoid arthritis indication 69896004 DOID:7148
Bursitis indication 84017003 DOID:2965
Osteoarthritis indication 396275006
Alcoholism contraindication 7200002
Peptic ulcer contraindication 13200003 DOID:750
Asthenia contraindication 13791008
Myocardial infarction contraindication 22298006 DOID:5844
Hypertensive disorder contraindication 38341003 DOID:10763
Gastrointestinal ulcer contraindication 40845000
Chronic heart failure contraindication 48447003
Disorder of cardiovascular system contraindication 49601007 DOID:1287
Gastrointestinal perforation contraindication 51875005
Systemic lupus erythematosus contraindication 55464009 DOID:9074
Blood coagulation disorder contraindication 64779008 DOID:1247
Gastrointestinal hemorrhage contraindication 74474003
Kidney disease contraindication 90708001 DOID:557
Kidney stone contraindication 95570007
Disorder of connective tissue contraindication 105969002 DOID:65
Coronary artery bypass graft contraindication 232717009
Disease of liver contraindication 235856003 DOID:409
Edema contraindication 267038008
Anemia contraindication 271737000 DOID:2355
Pregnancy, function contraindication 289908002
Cardiovascular event risk contraindication 395112001
Breastfeeding (mother) contraindication 413712001
Smokes tobacco daily contraindication 449868002




🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 4.33 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 INHIBITOR IC50 4.25 WOMBAT-PK CHEMBL
Prostaglandin G/H synthase 1 Enzyme INHIBITOR IC50 5.92 IUPHAR
Glycine receptor subunit alpha-1 Ion channel EC50 6.42 CHEMBL
Aldose reductase Enzyme IC50 6.43 CHEMBL
Peroxisome proliferator-activated receptor gamma Nuclear hormone receptor EC50 4.64 CHEMBL
Retinoic acid receptor RXR-alpha Nuclear hormone receptor IC50 4.08 CHEMBL
72 kDa type IV collagenase Enzyme WOMBAT-PK
Lactoylglutathione lyase Enzyme Ki 4.11 CHEMBL
Aldo-keto reductase family 1 member B10 Enzyme IC50 6.46 CHEMBL
Prostaglandin E synthase Enzyme IC50 4.10 CHEMBL
Complement C5 Secreted Kd 6.24 CHEMBL
Aldose reductase Enzyme IC50 6.36 DRUG MATRIX
Prostaglandin G/H synthase 1 Enzyme IC50 4.80 CHEMBL
Bile salt export pump Transporter IC50 4.06 CHEMBL

External reference:

IDSource
4017957 VUID
N0000146307 NUI
D00120 KEGG_DRUG
4017957 VANDF
C0038792 UMLSCUI
CHEBI:9352 CHEBI
SUZ PDB_CHEM_ID
CHEMBL15770 ChEMBL_ID
DB00605 DRUGBANK_ID
D013467 MESH_DESCRIPTOR_UI
1548887 PUBCHEM_CID
5425 IUPHAR_LIGAND_ID
3791 INN_ID
184SNS8VUH UNII
10237 RXNORM
2100 MMSL
285 MMSL
5535 MMSL
d00033 MMSL
002386 NDDF
387513000 SNOMEDCT_US
89505005 SNOMEDCT_US
184SNS8VUH INXIGHT DRUGS

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Sulindac HUMAN PRESCRIPTION DRUG LABEL 1 0591-5660 TABLET 200 mg ORAL ANDA 25 sections
Sulindac HUMAN PRESCRIPTION DRUG LABEL 1 0591-5661 TABLET 150 mg ORAL ANDA 25 sections
SULINDAC HUMAN PRESCRIPTION DRUG LABEL 1 0904-7334 TABLET 150 mg ORAL ANDA 28 sections
SULINDAC HUMAN PRESCRIPTION DRUG LABEL 1 0904-7335 TABLET 200 mg ORAL ANDA 28 sections
Sulindac HUMAN PRESCRIPTION DRUG LABEL 1 16590-211 TABLET 200 mg ORAL ANDA 19 sections
SULINDAC HUMAN PRESCRIPTION DRUG LABEL 1 24658-770 TABLET 150 mg ORAL ANDA 25 sections
SULINDAC HUMAN PRESCRIPTION DRUG LABEL 1 24658-771 TABLET 200 mg ORAL ANDA 25 sections
Sulindac HUMAN PRESCRIPTION DRUG LABEL 1 33261-100 TABLET 200 mg ORAL ANDA 19 sections
SULINDAC HUMAN PRESCRIPTION DRUG LABEL 1 42806-011 TABLET 200 mg ORAL ANDA 24 sections
SULINDAC HUMAN PRESCRIPTION DRUG LABEL 1 42806-018 TABLET 150 mg ORAL ANDA 24 sections
SULINDAC HUMAN PRESCRIPTION DRUG LABEL 1 50090-0529 TABLET 200 mg ORAL ANDA 24 sections
SULINDAC HUMAN PRESCRIPTION DRUG LABEL 1 50090-2093 TABLET 200 mg ORAL ANDA 27 sections
Sulindac HUMAN PRESCRIPTION DRUG LABEL 1 50090-4976 TABLET 200 mg ORAL ANDA 24 sections
Sulindac HUMAN PRESCRIPTION DRUG LABEL 1 52959-195 TABLET 200 mg ORAL ANDA 24 sections
SULINDAC HUMAN PRESCRIPTION DRUG LABEL 1 53489-478 TABLET 150 mg ORAL ANDA 28 sections
SULINDAC HUMAN PRESCRIPTION DRUG LABEL 1 53489-479 TABLET 200 mg ORAL ANDA 28 sections
SULINDAC HUMAN PRESCRIPTION DRUG LABEL 1 53808-0302 TABLET 200 mg ORAL ANDA 27 sections
Sulindac HUMAN PRESCRIPTION DRUG LABEL 1 53808-0303 TABLET 200 mg ORAL ANDA 22 sections
Sulindac HUMAN PRESCRIPTION DRUG LABEL 1 53808-0799 TABLET 150 mg ORAL ANDA 21 sections
Sulindac HUMAN PRESCRIPTION DRUG LABEL 1 53808-0814 TABLET 200 mg ORAL ANDA 19 sections
Sulindac HUMAN PRESCRIPTION DRUG LABEL 1 54738-902 TABLET 150 mg ORAL ANDA 28 sections
Sulindac HUMAN PRESCRIPTION DRUG LABEL 1 54738-903 TABLET 200 mg ORAL ANDA 28 sections
Sulindac HUMAN PRESCRIPTION DRUG LABEL 1 54868-0879 TABLET 150 mg ORAL ANDA 25 sections
Sulindac HUMAN PRESCRIPTION DRUG LABEL 1 54868-1118 TABLET 200 mg ORAL ANDA 25 sections
Sulindac HUMAN PRESCRIPTION DRUG LABEL 1 55289-930 TABLET 200 mg ORAL ANDA 25 sections
Sulindac HUMAN PRESCRIPTION DRUG LABEL 1 68151-2871 TABLET 200 mg ORAL ANDA 24 sections
Sulindac HUMAN PRESCRIPTION DRUG LABEL 1 68151-2872 TABLET 200 mg ORAL ANDA 24 sections
SULINDAC HUMAN PRESCRIPTION DRUG LABEL 1 71205-648 TABLET 200 mg ORAL ANDA 25 sections
SULINDAC HUMAN PRESCRIPTION DRUG LABEL 1 71335-0413 TABLET 200 mg ORAL ANDA 27 sections
SULINDAC HUMAN PRESCRIPTION DRUG LABEL 1 72789-373 TABLET 150 mg ORAL ANDA 28 sections