Details
Stereochemistry | ACHIRAL |
Molecular Formula | C7H7NO3 |
Molecular Weight | 153.1354 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
NC1=CC(O)=C(C=C1)C(O)=O
InChI
InChIKey=WUBBRNOQWQTFEX-UHFFFAOYSA-N
InChI=1S/C7H7NO3/c8-4-1-2-5(7(10)11)6(9)3-4/h1-3,9H,8H2,(H,10,11)
Molecular Formula | C7H7NO3 |
Molecular Weight | 153.1354 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionSources: http://www.drugbank.ca/drugs/DB00233Curator's Comment: Description was created based on several sources, including http://www.rxlist.com/paser-drug.htm
Sources: http://www.drugbank.ca/drugs/DB00233
Curator's Comment: Description was created based on several sources, including http://www.rxlist.com/paser-drug.htm
4-AMINOSALICYLIC ACID (Paser) is an anti-tuberculosis drug used to treat tuberculosis in combination with other active agents. 4-AMINOSALICYLIC ACID (Paser) is most commonly used in patients with Multi-drug Resistant TB (MDR-TB) or when isoniazid and rifampin use is not possible due to a combination of resistance and/or intolerance. There are two mechanisms responsible for aminosalicylic acid's bacteriostatic action against Mycobacterium tuberculosis. Firstly, aminosalicylic acid inhibits folic acid synthesis (without potentiation with antifolic compounds). The binding of para-aminobenzoic acid to pteridine synthetase acts as the first step in the folic acid synthesis. Aminosalicylic acid binds pteridine synthetase with greater affinity than para-aminobenzoic acid, effectively inhibiting the synthesis of folic acid. As bacteria are unable to use external sources of folic acid, cell growth and multiplication slow. Secondly, the aminosalicylic acid may inhibit the synthesis of the cell wall component, mycobactin, thus reducing iron uptake by M. tuberculosis.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL6065 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Sources: http://www.rxlist.com/paser-drug.htm |
Primary | PASER Approved UseTuberculosis Launch Date1994 |
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Primary | PASER Approved UseUnknown Launch Date1994 |
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Primary | Unknown Approved UseUnknown |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
53.63 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31682027/ |
4 g 2 times / day multiple, oral dose: 4 g route of administration: Oral experiment type: MULTIPLE co-administered: |
AMINOSALICYLIC ACID plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
82.69 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31682027/ |
8 g 1 times / day multiple, oral dose: 8 g route of administration: Oral experiment type: MULTIPLE co-administered: |
AMINOSALICYLIC ACID plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
20 μg/mL |
4 g single, oral dose: 4 g route of administration: Oral experiment type: SINGLE co-administered: |
AMINOSALICYLIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
16.36 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31682027/ |
8 g 1 times / day multiple, oral dose: 8 g route of administration: Oral experiment type: MULTIPLE co-administered: |
4-ACETAMIDOSALICYLIC ACID plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
14.59 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31682027/ |
4 g 2 times / day multiple, oral dose: 4 g route of administration: Oral experiment type: MULTIPLE co-administered: |
4-ACETAMIDOSALICYLIC ACID plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
414.07 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31682027/ |
4 g 2 times / day multiple, oral dose: 4 g route of administration: Oral experiment type: MULTIPLE co-administered: |
AMINOSALICYLIC ACID plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
690.35 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31682027/ |
8 g 1 times / day multiple, oral dose: 8 g route of administration: Oral experiment type: MULTIPLE co-administered: |
AMINOSALICYLIC ACID plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
142.49 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31682027/ |
8 g 1 times / day multiple, oral dose: 8 g route of administration: Oral experiment type: MULTIPLE co-administered: |
4-ACETAMIDOSALICYLIC ACID plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
145.02 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31682027/ |
4 g 2 times / day multiple, oral dose: 4 g route of administration: Oral experiment type: MULTIPLE co-administered: |
4-ACETAMIDOSALICYLIC ACID plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1.62 h |
4 g single, oral dose: 4 g route of administration: Oral experiment type: SINGLE co-administered: |
AMINOSALICYLIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
45% |
4 g single, oral dose: 4 g route of administration: Oral experiment type: SINGLE co-administered: |
AMINOSALICYLIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
3 g 2 times / day multiple, oral Highest studied dose Dose: 3 g, 2 times / day Route: oral Route: multiple Dose: 3 g, 2 times / day Sources: Page: p.356 |
unhealthy, 45.5 n = 23 Health Status: unhealthy Condition: Ulcerative colitis Age Group: 45.5 Sex: M+F Population Size: 23 Sources: Page: p.356 |
Disc. AE: Dyspepsia, Lipase increased... AEs leading to discontinuation/dose reduction: Dyspepsia (severe, 4.3%) Sources: Page: p.356Lipase increased (4.3%) Aspartate aminotransferase abnormal (4.3%) |
4 g 3 times / day multiple, oral Recommended Dose: 4 g, 3 times / day Route: oral Route: multiple Dose: 4 g, 3 times / day Sources: |
unhealthy n = 7492 Health Status: unhealthy Condition: Tuberculosis Sex: M+F Population Size: 7492 Sources: |
Disc. AE: Drug-induced hepatitis... AEs leading to discontinuation/dose reduction: Drug-induced hepatitis (0.5%) Sources: |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Aspartate aminotransferase abnormal | 4.3% Disc. AE |
3 g 2 times / day multiple, oral Highest studied dose Dose: 3 g, 2 times / day Route: oral Route: multiple Dose: 3 g, 2 times / day Sources: Page: p.356 |
unhealthy, 45.5 n = 23 Health Status: unhealthy Condition: Ulcerative colitis Age Group: 45.5 Sex: M+F Population Size: 23 Sources: Page: p.356 |
Lipase increased | 4.3% Disc. AE |
3 g 2 times / day multiple, oral Highest studied dose Dose: 3 g, 2 times / day Route: oral Route: multiple Dose: 3 g, 2 times / day Sources: Page: p.356 |
unhealthy, 45.5 n = 23 Health Status: unhealthy Condition: Ulcerative colitis Age Group: 45.5 Sex: M+F Population Size: 23 Sources: Page: p.356 |
Dyspepsia | severe, 4.3% Disc. AE |
3 g 2 times / day multiple, oral Highest studied dose Dose: 3 g, 2 times / day Route: oral Route: multiple Dose: 3 g, 2 times / day Sources: Page: p.356 |
unhealthy, 45.5 n = 23 Health Status: unhealthy Condition: Ulcerative colitis Age Group: 45.5 Sex: M+F Population Size: 23 Sources: Page: p.356 |
Drug-induced hepatitis | 0.5% Disc. AE |
4 g 3 times / day multiple, oral Recommended Dose: 4 g, 3 times / day Route: oral Route: multiple Dose: 4 g, 3 times / day Sources: |
unhealthy n = 7492 Health Status: unhealthy Condition: Tuberculosis Sex: M+F Population Size: 7492 Sources: |
PubMed
Title | Date | PubMed |
---|---|---|
A procedure for the determination of 4-aminosalicylic acid (p-aminosalicylic acid) in blood and in urine. | 1949 Feb |
|
Experience with topical administration of 4-aminosalicylic acid in ulcerative colitis. | 1989 Feb |
|
Tolerance of 4-aminosalicylic acid enemas in patients with inflammatory bowel disease and 5-aminosalicylic-induced acute pancreatitis. | 2004 May |
Patents
Sample Use Guides
The adult dosage of four grams (one packet) three times per day or correspondingly smaller doses in children.
Route of Administration:
Oral
In Vitro Use Guide
Curator's Comment: The developed nanodelivery formulation based on para-aminosalicylic acid (PAS) and zinc layered hydroxide has a fourfold higher efficacy of PAS against mycobacterium tuberculosis with a minimum inhibitory concentration (MIC) found to be at 1.40 ug/mL compared to the free drug PAS with a MIC of 5.0 ug/mL.
5.0 ug/mL MIC against mycobacterium tuberculosis.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:06:21 GMT 2023
by
admin
on
Fri Dec 15 15:06:21 GMT 2023
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Record UNII |
5B2658E0N2
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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EU-Orphan Drug |
EU/3/10/826
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WHO-ATC |
J04AA01
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FDA ORPHAN DRUG |
65792
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LIVERTOX |
42
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WHO-ATC |
J04AA02
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FDA ORPHAN DRUG |
220506
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WHO-ESSENTIAL MEDICINES LIST |
6.2.4
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WHO-VATC |
QJ04AA01
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WHO-ATC |
J04AA03
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NCI_THESAURUS |
C280
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FDA ORPHAN DRUG |
37989
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Code System | Code | Type | Description | ||
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1026401
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PRIMARY | |||
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200-613-5
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2083
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2050
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5B2658E0N2
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PRIMARY | |||
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D010131
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PRIMARY | |||
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113374
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ALTERNATIVE | |||
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DB00233
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PRIMARY | |||
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m1743
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PRIMARY | Merck Index | ||
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3203
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PRIMARY | |||
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CHEMBL1169
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PRIMARY | |||
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27565
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PRIMARY | |||
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100000092424
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PRIMARY | |||
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Aminosalicylic Acid
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PRIMARY | |||
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4649
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PRIMARY | |||
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7833
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PRIMARY | |||
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SUB12862MIG
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PRIMARY | |||
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65-49-6
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4-AMINOSALICYLIC ACID
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DTXSID2022591
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C47394
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PRIMARY |
Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT |
Related Record | Type | Details | ||
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PARENT -> IMPURITY |
Correction factors: for the calculation of contents, multiply the peak areas by 1.3
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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Related Record | Type | Details | ||
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ACTIVE MOIETY |