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=C(C(O)=O)C(O)=C1
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 |
||
Primary | PASER Approved UseUnknown Launch Date1994 |
|||
Primary | Unknown Approved UseUnknown |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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 |
|
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 |
|
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 |
|
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 |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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 |
|
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 |
|
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: |
unhealthy, 45.5 |
Disc. AE: Dyspepsia, Lipase increased... AEs leading to discontinuation/dose reduction: Dyspepsia (severe, 4.3%) Sources: Lipase 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 Health Status: unhealthy Sex: M+F 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: |
unhealthy, 45.5 |
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: |
unhealthy, 45.5 |
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: |
unhealthy, 45.5 |
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 Health Status: unhealthy Sex: M+F Sources: |
PubMed
Title | Date | PubMed |
---|---|---|
Tuberculostatic derivatives of rho-aminobenzoic acid; esters and amides of 4-aminosalicylic acid. | 1948 |
|
A procedure for the determination of 4-aminosalicylic acid (p-aminosalicylic acid) in blood and in urine. | 1949 Feb |
|
Treatment of left-sided ulcerative colitis with 4-aminosalicylic acid enemas. A double-blind, placebo-controlled trial. | 1988 Feb |
|
[Inhibition of intestinal leukotriene formation as a possible mechanism of action of sulfasalazine, 5-aminosalicylic acid and 4-aminosalicylic acid]. | 1988 Nov 15 |
|
Double blind, controlled trial of 4-aminosalicylic acid and prednisolone enemas in distal ulcerative colitis. | 1992 Jul |
|
Tolerance of 4-aminosalicylic acid enemas in patients with inflammatory bowel disease and 5-aminosalicylic-induced acute pancreatitis. | 2004 May |
|
Colon-specific prodrugs of 4-aminosalicylic acid for inflammatory bowel disease. | 2014 Apr 7 |
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
Mon Mar 31 17:46:36 GMT 2025
by
admin
on
Mon Mar 31 17:46:36 GMT 2025
|
Record UNII |
5B2658E0N2
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Systematic Name | English | ||
|
Preferred Name | English | ||
|
Systematic Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English |
Classification Tree | Code System | Code | ||
---|---|---|---|---|
|
EU-Orphan Drug |
EU/3/10/826
Created by
admin on Mon Mar 31 17:46:36 GMT 2025 , Edited by admin on Mon Mar 31 17:46:36 GMT 2025
|
||
|
WHO-ATC |
J04AA01
Created by
admin on Mon Mar 31 17:46:36 GMT 2025 , Edited by admin on Mon Mar 31 17:46:36 GMT 2025
|
||
|
FDA ORPHAN DRUG |
65792
Created by
admin on Mon Mar 31 17:46:36 GMT 2025 , Edited by admin on Mon Mar 31 17:46:36 GMT 2025
|
||
|
LIVERTOX |
42
Created by
admin on Mon Mar 31 17:46:36 GMT 2025 , Edited by admin on Mon Mar 31 17:46:36 GMT 2025
|
||
|
WHO-ATC |
J04AA02
Created by
admin on Mon Mar 31 17:46:36 GMT 2025 , Edited by admin on Mon Mar 31 17:46:36 GMT 2025
|
||
|
FDA ORPHAN DRUG |
220506
Created by
admin on Mon Mar 31 17:46:36 GMT 2025 , Edited by admin on Mon Mar 31 17:46:36 GMT 2025
|
||
|
WHO-ESSENTIAL MEDICINES LIST |
6.2.4
Created by
admin on Mon Mar 31 17:46:36 GMT 2025 , Edited by admin on Mon Mar 31 17:46:36 GMT 2025
|
||
|
WHO-VATC |
QJ04AA01
Created by
admin on Mon Mar 31 17:46:36 GMT 2025 , Edited by admin on Mon Mar 31 17:46:36 GMT 2025
|
||
|
WHO-ATC |
J04AA03
Created by
admin on Mon Mar 31 17:46:36 GMT 2025 , Edited by admin on Mon Mar 31 17:46:36 GMT 2025
|
||
|
NCI_THESAURUS |
C280
Created by
admin on Mon Mar 31 17:46:36 GMT 2025 , Edited by admin on Mon Mar 31 17:46:36 GMT 2025
|
||
|
FDA ORPHAN DRUG |
37989
Created by
admin on Mon Mar 31 17:46:36 GMT 2025 , Edited by admin on Mon Mar 31 17:46:36 GMT 2025
|
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
1026401
Created by
admin on Mon Mar 31 17:46:36 GMT 2025 , Edited by admin on Mon Mar 31 17:46:36 GMT 2025
|
PRIMARY | |||
|
200-613-5
Created by
admin on Mon Mar 31 17:46:36 GMT 2025 , Edited by admin on Mon Mar 31 17:46:36 GMT 2025
|
PRIMARY | |||
|
2083
Created by
admin on Mon Mar 31 17:46:36 GMT 2025 , Edited by admin on Mon Mar 31 17:46:36 GMT 2025
|
PRIMARY | |||
|
2050
Created by
admin on Mon Mar 31 17:46:36 GMT 2025 , Edited by admin on Mon Mar 31 17:46:36 GMT 2025
|
PRIMARY | |||
|
5B2658E0N2
Created by
admin on Mon Mar 31 17:46:36 GMT 2025 , Edited by admin on Mon Mar 31 17:46:36 GMT 2025
|
PRIMARY | |||
|
D010131
Created by
admin on Mon Mar 31 17:46:36 GMT 2025 , Edited by admin on Mon Mar 31 17:46:36 GMT 2025
|
PRIMARY | |||
|
113374
Created by
admin on Mon Mar 31 17:46:36 GMT 2025 , Edited by admin on Mon Mar 31 17:46:36 GMT 2025
|
ALTERNATIVE | |||
|
DB00233
Created by
admin on Mon Mar 31 17:46:36 GMT 2025 , Edited by admin on Mon Mar 31 17:46:36 GMT 2025
|
PRIMARY | |||
|
m1743
Created by
admin on Mon Mar 31 17:46:36 GMT 2025 , Edited by admin on Mon Mar 31 17:46:36 GMT 2025
|
PRIMARY | Merck Index | ||
|
3203
Created by
admin on Mon Mar 31 17:46:36 GMT 2025 , Edited by admin on Mon Mar 31 17:46:36 GMT 2025
|
PRIMARY | |||
|
CHEMBL1169
Created by
admin on Mon Mar 31 17:46:36 GMT 2025 , Edited by admin on Mon Mar 31 17:46:36 GMT 2025
|
PRIMARY | |||
|
27565
Created by
admin on Mon Mar 31 17:46:36 GMT 2025 , Edited by admin on Mon Mar 31 17:46:36 GMT 2025
|
PRIMARY | |||
|
100000092424
Created by
admin on Mon Mar 31 17:46:36 GMT 2025 , Edited by admin on Mon Mar 31 17:46:36 GMT 2025
|
PRIMARY | |||
|
Aminosalicylic Acid
Created by
admin on Mon Mar 31 17:46:36 GMT 2025 , Edited by admin on Mon Mar 31 17:46:36 GMT 2025
|
PRIMARY | |||
|
4649
Created by
admin on Mon Mar 31 17:46:36 GMT 2025 , Edited by admin on Mon Mar 31 17:46:36 GMT 2025
|
PRIMARY | |||
|
7833
Created by
admin on Mon Mar 31 17:46:36 GMT 2025 , Edited by admin on Mon Mar 31 17:46:36 GMT 2025
|
PRIMARY | |||
|
SUB12862MIG
Created by
admin on Mon Mar 31 17:46:36 GMT 2025 , Edited by admin on Mon Mar 31 17:46:36 GMT 2025
|
PRIMARY | |||
|
65-49-6
Created by
admin on Mon Mar 31 17:46:36 GMT 2025 , Edited by admin on Mon Mar 31 17:46:36 GMT 2025
|
PRIMARY | |||
|
4-AMINOSALICYLIC ACID
Created by
admin on Mon Mar 31 17:46:36 GMT 2025 , Edited by admin on Mon Mar 31 17:46:36 GMT 2025
|
PRIMARY | |||
|
DTXSID2022591
Created by
admin on Mon Mar 31 17:46:36 GMT 2025 , Edited by admin on Mon Mar 31 17:46:36 GMT 2025
|
PRIMARY | |||
|
C47394
Created by
admin on Mon Mar 31 17:46:36 GMT 2025 , Edited by admin on Mon Mar 31 17:46:36 GMT 2025
|
PRIMARY |
Related Record | Type | Details | ||
---|---|---|---|---|
|
SALT/SOLVATE -> PARENT |
|
||
|
SALT/SOLVATE -> PARENT |
|
||
|
SALT/SOLVATE -> PARENT |
|
||
|
SALT/SOLVATE -> PARENT |
|
||
|
SALT/SOLVATE -> PARENT |
|
||
|
SALT/SOLVATE -> PARENT |
|
||
|
SALT/SOLVATE -> PARENT |
|
||
|
SALT/SOLVATE -> PARENT |
|
||
|
SALT/SOLVATE -> PARENT |
|
Related Record | Type | Details | ||
---|---|---|---|---|
|
PARENT -> IMPURITY |
Correction factors: for the calculation of contents, multiply the peak areas by 1.3
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
Related Record | Type | Details | ||
---|---|---|---|---|
|
ACTIVE MOIETY |
|