sulindac Indications/Contra | FAERs-F | FAERs-M | Orange Bk | 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 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 88 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H

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 90.75 18.74 95 2988 243730 46439249
Hangover 28.40 18.74 8 3075 1287 46681692
Crystal nephropathy 22.27 18.74 6 3077 819 46682160

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 31.28 20.76 12 1054 9455 29941957

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
FDA EPC N0000175722 Nonsteroidal Anti-inflammatory Drug
MeSH PA D000700 Analgesics
MeSH PA D018712 Analgesics, Non-Narcotic
MeSH PA D000893 Anti-Inflammatory Agents
MeSH PA D000894 Anti-Inflammatory Agents, Non-Steroidal
MeSH PA D000970 Antineoplastic Agents
MeSH PA D018501 Antirheumatic Agents
MeSH PA D016861 Cyclooxygenase Inhibitors
MeSH PA D004791 Enzyme Inhibitors
MeSH PA D018373 Peripheral Nervous System Agents
MeSH PA D018689 Sensory System Agents
CHEBI has role CHEBI:35475 non-steroidal anti-inflammatory drugs
CHEBI has role CHEBI:35493 anti-pyretic
CHEBI has role CHEBI:35544 cyclooxygenase inhibitors
CHEBI has role CHEBI:35610 cytostatic
CHEBI has role CHEBI:50266 prodrugs
CHEBI has role CHEBI:66993 anti-contraction drug
CHEBI has role CHEBI:68495 type i programmed cell-death inducer

Drug Use (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

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
72 kDa type IV collagenase Enzyme WOMBAT-PK
Retinoic acid receptor RXR-alpha Nuclear hormone receptor IC50 4.08 CHEMBL
Prostaglandin E synthase Enzyme IC50 4.10 CHEMBL
Lactoylglutathione lyase Enzyme Ki 4.11 CHEMBL
Aldose reductase Enzyme IC50 6.43 CHEMBL
Glycine receptor subunit alpha-1 Ion channel EC50 6.42 CHEMBL
Aldose reductase Enzyme IC50 6.36 DRUG MATRIX
Bile salt export pump Unclassified IC50 4.06 CHEMBL

External reference:

IDSource
4017957 VUID
N0000146307 NUI
D00120 KEGG_DRUG
4017957 VANDF
C0591267 UMLSCUI
CHEBI:9352 CHEBI
SUZ PDB_CHEM_ID
CHEMBL15770 ChEMBL_ID
D013467 MESH_DESCRIPTOR_UI
1548887 PUBCHEM_CID
3791 INN_ID
DB00605 DRUGBANK_ID
184SNS8VUH UNII
5425 IUPHAR_LIGAND_ID
10237 RXNORM
2100 MMSL
285 MMSL
5535 MMSL
d00033 MMSL
002386 NDDF
387513000 SNOMEDCT_US
89505005 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Sulindac HUMAN PRESCRIPTION DRUG LABEL 1 0378-0427 TABLET 150 mg ORAL ANDA 26 sections
Sulindac HUMAN PRESCRIPTION DRUG LABEL 1 0378-0531 TABLET 200 mg ORAL ANDA 26 sections
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 0904-6216 TABLET 150 mg ORAL ANDA 24 sections
Sulindac HUMAN PRESCRIPTION DRUG LABEL 1 0904-6217 TABLET 200 mg ORAL ANDA 24 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 25 sections
SULINDAC HUMAN PRESCRIPTION DRUG LABEL 1 42806-018 TABLET 150 mg ORAL ANDA 25 sections
SULINDAC HUMAN PRESCRIPTION DRUG LABEL 1 50090-0529 TABLET 200 mg ORAL ANDA 25 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 55700-682 TABLET 200 mg ORAL ANDA 25 sections
SUNLINDAC HUMAN PRESCRIPTION DRUG LABEL 1 61919-211 TABLET 200 mg ORAL ANDA 9 sections
Sulindac HUMAN PRESCRIPTION DRUG LABEL 1 63629-3208 TABLET 200 mg ORAL ANDA 25 sections
Sulindac HUMAN PRESCRIPTION DRUG LABEL 1 68151-2871 TABLET 200 mg ORAL ANDA 24 sections