U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of AMINOSALICYLIC ACID

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)

HIDE SMILES / InChI

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

Description
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.

CNS Activity

Curator's Comment: In humans CSF penetration occurs only if the meninges is inflamed. Shown to be CNS penetrant in mouse http://www.nature.com/aps/journal/vaop/ncurrent/pdf/aps2014103a.pdf

Originator

Curator's Comment: In 1943 Jorgen Lehmann, a Swedish physician, developed para-aminosalicylic acid (PASCAINE). Lehmann first tried PAS as an oral TB therapy late in 1944.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
PASER

Approved Use

Tuberculosis

Launch Date

7.729344E11
Primary
PASER

Approved Use

Unknown

Launch Date

7.7284803E11
Primary
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
53.63 mg/L
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
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
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
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

AUC

ValueDoseCo-administeredAnalytePopulation
414.07 mg × h/L
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
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
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
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

T1/2

ValueDoseCo-administeredAnalytePopulation
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

Funbound

ValueDoseCo-administeredAnalytePopulation
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

Doses

DosePopulationAdverse 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%)
Lipase increased (4.3%)
Aspartate aminotransferase abnormal (4.3%)
Sources: Page: p.356
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

AEs

AESignificanceDosePopulation
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:
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
[Inhibition of intestinal leukotriene formation as a possible mechanism of action of sulfasalazine, 5-aminosalicylic acid and 4-aminosalicylic acid].
1988 Nov 15
4-Aminosalicylic acid enemas for ulcerative colitis.
1989 Feb 25
Luminal concentrations of orally ingested 4-aminosalicylic acid as determined by in-vivo equilibrium dialysis.
1990 Dec
Double blind, controlled trial of 4-aminosalicylic acid and prednisolone enemas in distal ulcerative colitis.
1992 Jul
Colon-specific prodrugs of 4-aminosalicylic acid for inflammatory bowel disease.
2014 Apr 7
Patents

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 Fri Dec 15 15:06:21 UTC 2023
Edited
by admin
on Fri Dec 15 15:06:21 UTC 2023
Record UNII
5B2658E0N2
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
AMINOSALICYLIC ACID
HSDB   MART.   ORANGE BOOK   USP   USP-RS   VANDF   WHO-DD  
Systematic Name English
PARA-AMINOSALICYLIC ACID
Systematic Name English
4-AMINO-2-HYDROXYBENZOIC ACID
Systematic Name English
AMINOSALICYLIC ACID [USP MONOGRAPH]
Common Name English
Aminosalicylic acid [WHO-DD]
Common Name English
P-AMINOSALICYLIC ACID [MI]
Common Name English
BENZOIC ACID, 4-AMINO-2-HYDROXY-
Common Name English
AMINOSALICYLIC ACID [ORANGE BOOK]
Common Name English
AMINOSALICYLATE
Systematic Name English
NEOPASALATE COMPONENT AMINOSALICYLIC ACID
Common Name English
AMINOSALICYLIC ACID COMPONENT OF NEOPASALATE
Common Name English
P-AMINOSALICYLIC ACID
MI  
Common Name English
AMINOSALICYLIC ACID [MART.]
Common Name English
4-Aminosalicylic acid
Systematic Name English
AMINOSALICYLIC ACID [HSDB]
Common Name English
PASER
Brand Name English
MESALAZINE IMPURITY E [EP IMPURITY]
Common Name English
PARASAL
Brand Name English
PAS
Common Name English
AMINOSALICYLIC ACID [VANDF]
Common Name English
NSC-2083
Code English
AMINOSALICYLIC ACID [USP-RS]
Common Name English
Classification Tree Code System Code
EU-Orphan Drug EU/3/10/826
Created by admin on Fri Dec 15 15:06:21 UTC 2023 , Edited by admin on Fri Dec 15 15:06:21 UTC 2023
WHO-ATC J04AA01
Created by admin on Fri Dec 15 15:06:21 UTC 2023 , Edited by admin on Fri Dec 15 15:06:21 UTC 2023
FDA ORPHAN DRUG 65792
Created by admin on Fri Dec 15 15:06:21 UTC 2023 , Edited by admin on Fri Dec 15 15:06:21 UTC 2023
LIVERTOX 42
Created by admin on Fri Dec 15 15:06:21 UTC 2023 , Edited by admin on Fri Dec 15 15:06:21 UTC 2023
WHO-ATC J04AA02
Created by admin on Fri Dec 15 15:06:21 UTC 2023 , Edited by admin on Fri Dec 15 15:06:21 UTC 2023
FDA ORPHAN DRUG 220506
Created by admin on Fri Dec 15 15:06:21 UTC 2023 , Edited by admin on Fri Dec 15 15:06:21 UTC 2023
WHO-ESSENTIAL MEDICINES LIST 6.2.4
Created by admin on Fri Dec 15 15:06:21 UTC 2023 , Edited by admin on Fri Dec 15 15:06:21 UTC 2023
WHO-VATC QJ04AA01
Created by admin on Fri Dec 15 15:06:21 UTC 2023 , Edited by admin on Fri Dec 15 15:06:21 UTC 2023
WHO-ATC J04AA03
Created by admin on Fri Dec 15 15:06:21 UTC 2023 , Edited by admin on Fri Dec 15 15:06:21 UTC 2023
NCI_THESAURUS C280
Created by admin on Fri Dec 15 15:06:21 UTC 2023 , Edited by admin on Fri Dec 15 15:06:21 UTC 2023
FDA ORPHAN DRUG 37989
Created by admin on Fri Dec 15 15:06:21 UTC 2023 , Edited by admin on Fri Dec 15 15:06:21 UTC 2023
Code System Code Type Description
RS_ITEM_NUM
1026401
Created by admin on Fri Dec 15 15:06:21 UTC 2023 , Edited by admin on Fri Dec 15 15:06:21 UTC 2023
PRIMARY
ECHA (EC/EINECS)
200-613-5
Created by admin on Fri Dec 15 15:06:21 UTC 2023 , Edited by admin on Fri Dec 15 15:06:21 UTC 2023
PRIMARY
NSC
2083
Created by admin on Fri Dec 15 15:06:21 UTC 2023 , Edited by admin on Fri Dec 15 15:06:21 UTC 2023
PRIMARY
DRUG CENTRAL
2050
Created by admin on Fri Dec 15 15:06:21 UTC 2023 , Edited by admin on Fri Dec 15 15:06:21 UTC 2023
PRIMARY
FDA UNII
5B2658E0N2
Created by admin on Fri Dec 15 15:06:21 UTC 2023 , Edited by admin on Fri Dec 15 15:06:21 UTC 2023
PRIMARY
MESH
D010131
Created by admin on Fri Dec 15 15:06:21 UTC 2023 , Edited by admin on Fri Dec 15 15:06:21 UTC 2023
PRIMARY
RXCUI
113374
Created by admin on Fri Dec 15 15:06:21 UTC 2023 , Edited by admin on Fri Dec 15 15:06:21 UTC 2023
ALTERNATIVE
DRUG BANK
DB00233
Created by admin on Fri Dec 15 15:06:21 UTC 2023 , Edited by admin on Fri Dec 15 15:06:21 UTC 2023
PRIMARY
MERCK INDEX
m1743
Created by admin on Fri Dec 15 15:06:21 UTC 2023 , Edited by admin on Fri Dec 15 15:06:21 UTC 2023
PRIMARY Merck Index
HSDB
3203
Created by admin on Fri Dec 15 15:06:21 UTC 2023 , Edited by admin on Fri Dec 15 15:06:21 UTC 2023
PRIMARY
ChEMBL
CHEMBL1169
Created by admin on Fri Dec 15 15:06:21 UTC 2023 , Edited by admin on Fri Dec 15 15:06:21 UTC 2023
PRIMARY
CHEBI
27565
Created by admin on Fri Dec 15 15:06:21 UTC 2023 , Edited by admin on Fri Dec 15 15:06:21 UTC 2023
PRIMARY
SMS_ID
100000092424
Created by admin on Fri Dec 15 15:06:21 UTC 2023 , Edited by admin on Fri Dec 15 15:06:21 UTC 2023
PRIMARY
LACTMED
Aminosalicylic Acid
Created by admin on Fri Dec 15 15:06:21 UTC 2023 , Edited by admin on Fri Dec 15 15:06:21 UTC 2023
PRIMARY
PUBCHEM
4649
Created by admin on Fri Dec 15 15:06:21 UTC 2023 , Edited by admin on Fri Dec 15 15:06:21 UTC 2023
PRIMARY
RXCUI
7833
Created by admin on Fri Dec 15 15:06:21 UTC 2023 , Edited by admin on Fri Dec 15 15:06:21 UTC 2023
PRIMARY
EVMPD
SUB12862MIG
Created by admin on Fri Dec 15 15:06:21 UTC 2023 , Edited by admin on Fri Dec 15 15:06:21 UTC 2023
PRIMARY
CAS
65-49-6
Created by admin on Fri Dec 15 15:06:21 UTC 2023 , Edited by admin on Fri Dec 15 15:06:21 UTC 2023
PRIMARY
WIKIPEDIA
4-AMINOSALICYLIC ACID
Created by admin on Fri Dec 15 15:06:21 UTC 2023 , Edited by admin on Fri Dec 15 15:06:21 UTC 2023
PRIMARY
EPA CompTox
DTXSID2022591
Created by admin on Fri Dec 15 15:06:21 UTC 2023 , Edited by admin on Fri Dec 15 15:06:21 UTC 2023
PRIMARY
NCI_THESAURUS
C47394
Created by admin on Fri Dec 15 15:06:21 UTC 2023 , Edited by admin on Fri Dec 15 15:06:21 UTC 2023
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