mesalazine Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
phenylazosalicylic acid derivatives antibacterial 1710 89-57-6

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • 5-ASA
  • mesalamine
  • 2-Hydroxy-5-aminobenzoic acid
  • 3-Carboxy-4-hydroxyaniline
  • 5-Amino-2-hydroxybenzoic acid
  • 5-Aminosalicylic acid
  • claversal
  • mesacol
  • mesalazine
  • mesalsal
  • mesasal
  • m-Aminosalicylic acid
  • mesalamine hydrochloride
  • mesalamine HCl
An anti-inflammatory agent, structurally related to the SALICYLATES, which is active in INFLAMMATORY BOWEL DISEASE. It is considered to be the active moiety of SULPHASALAZINE. (From Martindale, The Extra Pharmacopoeia, 30th ed)
  • Molecular weight: 153.14
  • Formula: C7H7NO3
  • CLOGP: 1.06
  • LIPINSKI: 0
  • HAC: 4
  • HDO: 3
  • TPSA: 83.55
  • ALOGS: -1.10
  • ROTB: 1

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
1.50 g O
1.50 g R

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 2 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 1 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 7 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 447.77 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
Vd (Volume of distribution) 0.33 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 9.30 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.39 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 0.61 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Dec. 24, 1987 FDA MEDA PHARMS

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
Colitis ulcerative 512.69 33.98 101 1369 2701 2353914
Product use issue 383.76 33.98 105 1365 12064 2344551
Crohn's disease 298.13 33.98 76 1394 6579 2350036
Product residue present 244.15 33.98 47 1423 1089 2355526
Condition aggravated 240.08 33.98 93 1377 31886 2324729
Drug ineffective 215.64 33.98 123 1347 101501 2255114
Off label use 182.62 33.98 99 1371 73499 2283116
Inappropriate schedule of product administration 176.90 33.98 58 1412 12146 2344469
Diarrhoea 162.83 33.98 96 1374 83468 2273147
Tubulointerstitial nephritis 149.92 33.98 36 1434 2402 2354213
Myocarditis 140.03 33.98 30 1440 1193 2355422
Haematochezia 126.64 33.98 37 1433 5258 2351357
Exposure during pregnancy 116.26 33.98 52 1418 25167 2331448
Diarrhoea haemorrhagic 114.62 33.98 26 1444 1347 2355268
Colitis 105.30 33.98 32 1438 5194 2351421
Pyrexia 104.80 33.98 62 1408 53646 2302969
Pancreatitis acute 101.31 33.98 29 1441 3824 2352791
Abdominal pain 100.91 33.98 52 1418 34322 2322293
Nausea 100.63 33.98 80 1390 112109 2244506
Arthralgia 93.82 33.98 58 1412 54227 2302388
Maternal exposure during pregnancy 92.66 33.98 38 1432 14825 2341790
Frequent bowel movements 90.50 33.98 23 1447 1931 2354684
Interstitial lung disease 84.95 33.98 30 1440 7782 2348833
Pancreatitis 80.20 33.98 29 1441 8050 2348565
No adverse event 79.14 33.98 30 1440 9498 2347117
Chromaturia 78.11 33.98 22 1448 2731 2353884
Product administered to patient of inappropriate age 77.18 33.98 17 1453 767 2355848
Drug hypersensitivity 75.84 33.98 48 1422 46595 2310020
Alopecia 72.36 33.98 36 1434 21965 2334650
Abdominal pain upper 72.21 33.98 36 1434 22064 2334551
Product quality issue 71.93 33.98 29 1441 10800 2345815
Organising pneumonia 70.00 33.98 16 1454 855 2355760
Anaemia 62.01 33.98 38 1432 34754 2321861
Acute kidney injury 61.33 33.98 35 1435 28087 2328528
Premature labour 60.50 33.98 17 1453 2089 2354526
Vomiting 57.35 33.98 48 1422 71554 2285061
Headache 56.62 33.98 50 1420 80129 2276486
Myalgia 56.17 33.98 31 1439 23302 2333313
Iron deficiency anaemia 56.03 33.98 16 1454 2083 2354532
Agranulocytosis 52.07 33.98 17 1453 3465 2353150
Acute febrile neutrophilic dermatosis 51.09 33.98 11 1459 445 2356170
Rectal haemorrhage 50.61 33.98 19 1451 5837 2350778
Weight decreased 47.99 33.98 30 1440 28341 2328274
Asthenia 47.18 33.98 36 1434 46890 2309725
Dehydration 46.56 33.98 27 1443 22268 2334347
Abdominal distension 46.30 33.98 21 1449 10390 2346225
Dysphagia 45.14 33.98 22 1448 12783 2343832
Fatigue 44.66 33.98 45 1425 84828 2271787
Abdominal discomfort 44.21 33.98 24 1446 17432 2339183
Pleural effusion 44.01 33.98 21 1449 11647 2344968
Flatulence 43.94 33.98 16 1454 4509 2352106
Gastrointestinal disorder 42.88 33.98 19 1451 8898 2347717
Appetite disorder 42.16 33.98 10 1460 627 2355988
Drug intolerance 40.79 33.98 21 1449 13696 2342919
Dizziness 40.13 33.98 36 1434 58629 2297986
Eosinophilic pneumonia 40.03 33.98 9 1461 445 2356170
Rash 39.67 33.98 36 1434 59522 2297093
Haemorrhagic diathesis 38.45 33.98 9 1461 533 2356082
Hypersensitivity 37.50 33.98 24 1446 23569 2333046
Sjogren's syndrome 37.48 33.98 10 1460 1011 2355604
Premature delivery 37.46 33.98 13 1457 3187 2353428
Mucous stools 36.86 33.98 8 1462 336 2356279
Abnormal loss of weight 36.35 33.98 9 1461 676 2355939
Oral administration complication 35.20 33.98 6 1464 67 2356548
Pericardial effusion 34.59 33.98 13 1457 3996 2352619
Constipation 34.36 33.98 22 1448 21607 2335008

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
Colitis ulcerative 386.79 37.25 85 1311 2449 1742936
Myocarditis 246.93 37.25 56 1340 1847 1743538
Drug ineffective 231.38 37.25 128 1268 63673 1681712
Crohn's disease 216.33 37.25 60 1336 4527 1740858
Product use issue 203.59 37.25 66 1330 8505 1736880
Product residue present 186.11 37.25 38 1358 748 1744637
Off label use 180.20 37.25 92 1304 38479 1706906
Diarrhoea 159.29 37.25 95 1301 53757 1691628
Tubulointerstitial nephritis 145.25 37.25 40 1356 2918 1742467
Pyrexia 139.92 37.25 83 1313 46317 1699068
Condition aggravated 132.98 37.25 62 1334 21088 1724297
Haematochezia 125.06 37.25 40 1356 4892 1740493
Pericarditis 119.73 37.25 30 1366 1508 1743877
Abdominal pain 116.72 37.25 57 1339 21433 1723952
Pancreatitis acute 107.08 37.25 34 1362 4053 1741332
Colitis 106.33 37.25 34 1362 4146 1741239
Eosinophilic pneumonia 102.11 37.25 22 1374 563 1744822
Inappropriate schedule of product administration 97.83 37.25 37 1359 7422 1737963
Weight decreased 96.21 37.25 51 1345 22702 1722683
Pancreatitis 95.52 37.25 36 1360 7151 1738234
No adverse event 95.26 37.25 33 1363 5149 1740236
Frequent bowel movements 91.43 37.25 24 1372 1450 1743935
Diarrhoea haemorrhagic 84.09 37.25 21 1375 1038 1744347
Anaemia 73.74 37.25 47 1349 29410 1715975
Agranulocytosis 66.54 37.25 23 1373 3553 1741832
Eosinophilia 59.15 37.25 21 1375 3506 1741879
Nephrotic syndrome 55.12 37.25 16 1380 1400 1743985
Colitis microscopic 54.01 37.25 12 1384 354 1745031
Interstitial lung disease 53.25 37.25 26 1370 9670 1735715
Hepatosplenic T-cell lymphoma 53.13 37.25 10 1386 125 1745260
Drug hypersensitivity 52.93 37.25 30 1366 15105 1730280
Periumbilical abscess 51.62 37.25 7 1389 5 1745380
Leukopenia 50.37 37.25 24 1372 8456 1736929
Organising pneumonia 47.96 37.25 13 1383 885 1744500
Nausea 46.76 37.25 45 1351 51151 1694234
Haemophagocytic lymphohistiocytosis 45.95 37.25 14 1382 1446 1743939
Pericardial effusion 45.01 37.25 17 1379 3373 1742012
Bone marrow failure 44.49 37.25 19 1377 5181 1740204
Small intestinal obstruction 42.86 37.25 14 1382 1813 1743572
Abdominal pain upper 41.68 37.25 23 1373 10978 1734407
Vomiting 41.35 37.25 37 1359 38278 1707107
Cytomegalovirus enteritis 40.84 37.25 7 1389 49 1745336
Epstein-Barr virus test positive 40.32 37.25 8 1388 134 1745251
Gastroenteritis clostridial 40.24 37.25 7 1389 54 1745331
Intestinal diaphragm disease 39.80 37.25 7 1389 58 1745327
Product administered to patient of inappropriate age 39.74 37.25 11 1385 809 1744576
Rash 39.07 37.25 36 1360 38657 1706728
Pancytopenia 38.29 37.25 22 1374 11335 1734050

Pharmacologic Action:

SourceCodeDescription
ATC A07EC02 ALIMENTARY TRACT AND METABOLISM
ANTIDIARRHEALS, INTESTINAL ANTIINFLAMMATORY/ANTIINFECTIVE AGENTS
INTESTINAL ANTIINFLAMMATORY AGENTS
Aminosalicylic acid and similar agents
CHEBI has role CHEBI:35475 non-steroidal anti-inflammatory drug
FDA EPC N0000175781 Aminosalicylate
FDA CS M0000971 Aminosalicylic Acids
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 D018501 Antirheumatic Agents
MeSH PA D018373 Peripheral Nervous System Agents
MeSH PA D018689 Sensory System Agents

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Chronic ulcerative proctitis indication 52231000
Chronic ulcerative rectosigmoiditis indication 52506002
Ulcerative colitis indication 64766004 DOID:8577
Ulcerative colitis in remission indication 697969008
Crohn's disease off-label use 34000006
Interstitial nephritis contraindication 28689008 DOID:1063
Minimal change disease contraindication 44785005 DOID:10966
Kidney disease contraindication 90708001 DOID:557
Disease of liver contraindication 235856003 DOID:409
Pyloric obstruction contraindication 244815007
Anemia contraindication 271737000 DOID:2355
Neutropenic disorder contraindication 303011007 DOID:1227

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 2.74 acidic
pKa2 13.47 acidic
pKa3 5.86 Basic

Orange Book patent data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent use
800MG ASACOL HD APIL N021830 May 29, 2008 RX TABLET, DELAYED RELEASE ORAL 6893662 Nov. 15, 2021 TREATMENT OF ULCERATIVE COLITIS
375MG APRISO VALEANT PHARMS INTL N022301 Oct. 31, 2008 RX CAPSULE, EXTENDED RELEASE ORAL 8865688 May 1, 2030 FOR THE MAINTENANCE OF REMISSION OF ULCERATIVE COLITIS

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Arachidonate 5-lipoxygenase Enzyme INHIBITOR CHEMBL CHEMBL
Prostaglandin G/H synthase 2 Enzyme INHIBITOR DRUGBANK CHEMBL
Prostaglandin G/H synthase 1 Enzyme INHIBITOR WOMBAT-PK CHEMBL
Peroxisome proliferator-activated receptor gamma Nuclear hormone receptor AGONIST UNKNOWN IUPHAR

External reference:

IDSource
4019494 VUID
N0000147614 NUI
C0127615 UMLSCUI
D00377 KEGG_DRUG
4Q81I59GXC UNII
5444 INN_ID
387501005 SNOMEDCT_US
86977007 SNOMEDCT_US
37855 MMSL
5056 MMSL
d01031 MMSL
4019494 VANDF
52582 RXNORM
001600 NDDF
37856 MMSL
4075 PUBCHEM_CID
CHEBI:6775 CHEBI
CHEMBL704 ChEMBL_ID
DB00244 DRUGBANK_ID
D019804 MESH_DESCRIPTOR_UI
2700 IUPHAR_LIGAND_ID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Delzicol HUMAN PRESCRIPTION DRUG LABEL 1 0023-5853 CAPSULE, DELAYED RELEASE 400 mg ORAL NDA 17 sections
Asacol HD HUMAN PRESCRIPTION DRUG LABEL 1 0023-5901 TABLET, DELAYED RELEASE 800 mg ORAL NDA 16 sections
sfRowasa HUMAN PRESCRIPTION DRUG LABEL 1 0037-0022 SUSPENSION 4 g RECTAL NDA 11 sections
Rowasa HUMAN PRESCRIPTION DRUG LABEL 1 0037-0066 SUSPENSION 4 g RECTAL NDA 12 sections
Mesalamine HUMAN PRESCRIPTION DRUG LABEL 1 0093-5907 CAPSULE, DELAYED RELEASE 400 mg ORAL ANDA 17 sections
Mesalamine HUMAN PRESCRIPTION DRUG LABEL 1 0378-1375 CAPSULE, EXTENDED RELEASE 0.38 g ORAL ANDA 17 sections
Mesalamine HUMAN PRESCRIPTION DRUG LABEL 1 0378-7401 TABLET, DELAYED RELEASE 1.20 g ORAL ANDA 16 sections
Mesalamine HUMAN PRESCRIPTION DRUG LABEL 1 0378-9230 SUPPOSITORY 1000 mg RECTAL ANDA 17 sections
Mesalamine HUMAN PRESCRIPTION DRUG LABEL 1 0591-2245 TABLET, DELAYED RELEASE 1.20 g ORAL ANDA 16 sections
Mesalamine HUMAN PRESCRIPTION DRUG LABEL 1 0781-7088 SUPPOSITORY 1000 mg RECTAL ANDA 17 sections
mesalamine HUMAN PRESCRIPTION DRUG LABEL 1 16714-830 TABLET, DELAYED RELEASE 1.20 g ORAL ANDA 17 sections
Mesalamine HUMAN PRESCRIPTION DRUG LABEL 1 31722-005 SUPPOSITORY 1000 mg RECTAL ANDA 17 sections
Mesalamine HUMAN PRESCRIPTION DRUG LABEL 1 42291-563 CAPSULE, DELAYED RELEASE 400 mg ORAL ANDA 17 sections
Mesalamine HUMAN PRESCRIPTION DRUG LABEL 1 42291-564 TABLET, DELAYED RELEASE 1.20 g ORAL ANDA 16 sections
APRISO HUMAN PRESCRIPTION DRUG LABEL 1 43353-884 CAPSULE, EXTENDED RELEASE 375 mg ORAL NDA 18 sections
Mesalamine HUMAN PRESCRIPTION DRUG LABEL 1 45802-098 ENEMA 4 g RECTAL ANDA 12 sections
Mesalamine HUMAN PRESCRIPTION DRUG LABEL 1 45802-923 KIT 4 g None ANDA 13 sections
Mesalamine HUMAN PRESCRIPTION DRUG LABEL 1 45802-929 KIT 4 g None ANDA 14 sections
Delzicol HUMAN PRESCRIPTION DRUG LABEL 1 50090-3002 CAPSULE, DELAYED RELEASE 400 mg ORAL NDA 17 sections
mesalamine HUMAN PRESCRIPTION DRUG LABEL 1 50090-3497 TABLET, DELAYED RELEASE 800 mg ORAL NDA authorized generic 17 sections
Asacol HUMAN PRESCRIPTION DRUG LABEL 1 53808-0205 TABLET, DELAYED RELEASE 400 mg ORAL NDA 12 sections
ASACOL HUMAN PRESCRIPTION DRUG LABEL 1 53808-0823 TABLET, DELAYED RELEASE 400 mg ORAL NDA 11 sections
Mesalamine HUMAN PRESCRIPTION DRUG LABEL 1 54092-100 TABLET, DELAYED RELEASE 1.20 g ORAL NDA authorized generic 17 sections
Pentasa HUMAN PRESCRIPTION DRUG LABEL 1 54092-189 CAPSULE 250 mg ORAL NDA 12 sections
Pentasa HUMAN PRESCRIPTION DRUG LABEL 1 54092-191 CAPSULE 500 mg ORAL NDA 12 sections
Lialda HUMAN PRESCRIPTION DRUG LABEL 1 54092-476 TABLET, DELAYED RELEASE 1.20 g ORAL NDA 16 sections
Canasa HUMAN PRESCRIPTION DRUG LABEL 1 54868-6147 SUPPOSITORY 1000 mg RECTAL NDA 12 sections
APRISO HUMAN PRESCRIPTION DRUG LABEL 1 54868-6150 CAPSULE, EXTENDED RELEASE 375 mg ORAL NDA 17 sections
Canasa HUMAN PRESCRIPTION DRUG LABEL 1 58914-501 SUPPOSITORY 1000 mg RECTAL NDA 17 sections
MESALAMINE HUMAN PRESCRIPTION DRUG LABEL 1 59762-0117 CAPSULE, DELAYED RELEASE 400 mg ORAL NDA AUTHORIZED GENERIC 17 sections