aminosalicylic acid Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
2050 65-49-6

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • aminosalicylic acid resin complex
  • potassium aminosalicylate
  • p-aminosalicylic acid
  • aminosalicylic acid
  • 4-Aminosalicylic acid
  • 4-Carboxy-3-hydroxyaniline
  • apacil
  • calcium aminosalicylate
  • sodium aminosalicylate
  • para-aminosalicylic acid
  • aminosalicylate potassium
  • aminosalicylate sodium
  • teebacin
An antitubercular agent often administered in association with ISONIAZID. The sodium salt of the drug is better tolerated than the free acid.
  • Molecular weight: 153.14
  • Formula: C7H7NO3
  • CLOGP: 1.06
  • LIPINSKI: 0
  • HAC: 4
  • HDO: 3
  • TPSA: 83.55
  • ALOGS: -1.11
  • ROTB: 1

  • Status: OFP

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

Drug dosage:

DoseUnitRoute
12 g O
14 g O
14 g P
15 g O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 142.85 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) 1306.01 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD

Approvals:

DateAgencyCompanyOrphan
March 8, 1950 FDA CONSOLIDATED MIDLAND

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 386.24 29.28 108 2791 20953 53325214
Off label use 137.85 29.28 147 2752 472065 52874102
Frequent bowel movements 130.33 29.28 43 2856 14369 53331798
Drug resistance 112.94 29.28 42 2857 19920 53326247
Electrocardiogram QT prolonged 93.05 29.28 50 2849 56353 53289814
Mucous stools 62.07 29.28 17 2882 3009 53343158
Diarrhoea haemorrhagic 60.13 29.28 21 2878 8299 53337868
Pancreatitis 57.32 29.28 34 2865 46108 53300059
Lipase increased 53.97 29.28 20 2879 9358 53336809
Anaemia 51.67 29.28 69 2830 276649 53069518
Rectal haemorrhage 50.04 29.28 30 2869 41451 53304716
Haematochezia 49.46 29.28 30 2869 42328 53303839
Therapeutic reaction time decreased 49.29 29.28 12 2887 1335 53344832
Polyneuropathy 43.99 29.28 19 2880 13214 53332953
Neuropathy peripheral 42.44 29.28 39 2860 103148 53243019
Myelosuppression 41.27 29.28 18 2881 12810 53333357
Herbal toxicity 34.24 29.28 5 2894 31 53346136
Tuberculosis 33.88 29.28 15 2884 11056 53335111

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 252.56 30.34 81 2515 16970 32493960
Electrocardiogram QT prolonged 229.54 30.34 94 2502 39547 32471383
Off label use 190.26 30.34 171 2425 306149 32204781
Tuberculosis 160.54 30.34 49 2547 8680 32502250
Hepatotoxicity 125.88 30.34 50 2546 19287 32491643
Drug resistance 101.21 30.34 45 2551 22920 32488010
Intentional product use issue 75.33 30.34 45 2551 42166 32468764
Neuropathy peripheral 65.59 30.34 52 2544 76930 32434000
Frequent bowel movements 63.38 30.34 25 2571 9427 32501503
Myelosuppression 58.27 30.34 25 2571 11651 32499279
Blood pressure fluctuation 42.58 30.34 24 2572 20111 32490819
Faecal calprotectin increased 39.52 30.34 11 2585 1401 32509529
Polyneuropathy 37.04 30.34 19 2577 13196 32497734
Gastrointestinal inflammation 34.53 30.34 12 2584 3172 32507758

Pharmacologic Action:

SourceCodeDescription
ATC J04AA01 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIMYCOBACTERIALS
DRUGS FOR TREATMENT OF TUBERCULOSIS
Aminosalicylic acid and derivatives
ATC J04AA02 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIMYCOBACTERIALS
DRUGS FOR TREATMENT OF TUBERCULOSIS
Aminosalicylic acid and derivatives
ATC J04AA03 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIMYCOBACTERIALS
DRUGS FOR TREATMENT OF TUBERCULOSIS
Aminosalicylic acid and derivatives
MeSH PA D000900 Anti-Bacterial Agents
MeSH PA D000890 Anti-Infective Agents
MeSH PA D000995 Antitubercular Agents
CHEBI has role CHEBI:33231 antitubercular

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Acute tuberculosis indication 25629007
Pulmonary tuberculosis indication 154283005 DOID:2957
Crohn's disease off-label use 34000006
Ulcerative colitis off-label use 64766004 DOID:8577
Goiter contraindication 3716002 DOID:12176
Peptic ulcer contraindication 13200003 DOID:750
Hypokalemia contraindication 43339004
Crystalluria contraindication 46784006
Chronic heart failure contraindication 48447003
Acidosis contraindication 51387008
Duodenal ulcer disease contraindication 51868009 DOID:1724
Kidney disease contraindication 90708001 DOID:557
Anemia due to enzyme deficiency contraindication 111577008
Deficiency of glucose-6-phosphate dehydrogenase contraindication 124134002 DOID:2862
Cobalamin deficiency contraindication 190634004
Disease of liver contraindication 235856003 DOID:409
Gastric ulcer contraindication 397825006 DOID:10808

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 3.71 acidic
pKa2 12.94 acidic
pKa3 2.33 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
Cyclooxygenase Enzyme INHIBITOR CHEMBL CHEMBL
Tyrosine-protein phosphatase non-receptor type 1 Enzyme Kd 2.92 CHEMBL
2-amino-4-hydroxy-6-hydroxymethyldihydropteridine pyrophosphokinase Kinase WOMBAT-PK

External reference:

IDSource
4018852 VUID
N0000180192 NUI
D00162 KEGG_DRUG
133-09-5 SECONDARY_CAS_RN
4018852 VANDF
4018919 VANDF
C0030125 UMLSCUI
CHEBI:27565 CHEBI
BHA PDB_CHEM_ID
CHEMBL1169 ChEMBL_ID
CHEMBL1200584 ChEMBL_ID
CHEMBL2105983 ChEMBL_ID
CHEMBL2096646 ChEMBL_ID
CHEMBL1200966 ChEMBL_ID
D010131 MESH_DESCRIPTOR_UI
DB00233 DRUGBANK_ID
5B2658E0N2 UNII
4649 PUBCHEM_CID
7833 RXNORM
10002 MMSL
4176 MMSL
d01099 MMSL
d04226 MMSL
002845 NDDF
002846 NDDF
002847 NDDF
20231007 SNOMEDCT_US
255666002 SNOMEDCT_US
417238004 SNOMEDCT_US
65222005 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Paser HUMAN PRESCRIPTION DRUG LABEL 1 49938-107 GRANULE, DELAYED RELEASE 4 g ORAL ANDA 21 sections