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

Details

Stereochemistry ACHIRAL
Molecular Formula C7H6NO3.Na.2H2O
Molecular Weight 211.1478
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AMINOSALICYLATE SODIUM

SMILES

O.O.[Na+].NC1=CC(O)=C(C=C1)C([O-])=O

InChI

InChIKey=GMUQJDAYXZXBOT-UHFFFAOYSA-M
InChI=1S/C7H7NO3.Na.2H2O/c8-4-1-2-5(7(10)11)6(9)3-4;;;/h1-3,9H,8H2,(H,10,11);;2*1H2/q;+1;;/p-1

HIDE SMILES / InChI

Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula Na
Molecular Weight 22.9898
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

1994
Primary
PASER

Approved Use

Unknown

Launch Date

1994
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
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
[Ethers of 4-aminosalicylic acid].
1953 May
A double-blind clinical trial to compare the effects of 4-aminosalicylic acid to 5-aminosalicylic acid in topical treatment of ulcerative colitis.
1984
4-Aminosalicylic acid retention enemas in treatment of distal colitis.
1987 Jul
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
Experience with topical administration of 4-aminosalicylic acid in ulcerative colitis.
1989 Feb
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
A prospective randomized double blind trial comparing prednisolone and 4-aminosalicylic acid enemas in acute distal ulcerative colitis.
1992 Mar-Apr
Oral 4-aminosalicylic acid versus 5-aminosalicylic acid slow release tablets. Double blind, controlled pilot study in the maintenance treatment of Crohn's ileocolitis.
1994 Aug
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

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 15:36:04 GMT 2023
Edited
by admin
on Fri Dec 15 15:36:04 GMT 2023
Record UNII
S38B9W6AXW
Record Status Validated (UNII)
Record Version
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Name Type Language
AMINOSALICYLATE SODIUM
ORANGE BOOK   USP   VANDF  
Systematic Name English
P-AMINOSALICYLIC ACID MONOSODIUM SALT
Common Name English
Monosodium 4-aminosalicylate dihydrate
Systematic Name English
PARAMISAN SODIUM
Brand Name English
BENZOIC ACID, 4-AMINO-2-HYDROXY-, MONOSODIUM SALT, DIHYDRATE
Common Name English
SODIUM 4-AMINOSALICYLATE DIHYDRATE
Systematic Name English
PARA-AMINOSODIUM SALICYLATE [VANDF]
Common Name English
AMINOSALICYLATE SODIUM [VANDF]
Common Name English
SODIUM AMINOSALICYLATE DIHYDRATE
EP   MART.   VANDF   WHO-DD  
Systematic Name English
PASALON
Brand Name English
SODIUM AMINOSALICYLATE
Systematic Name English
PARASAL SODIUM
Brand Name English
NEMASOL SODIUM
Brand Name English
SODIUM AMINOSALICYLATE DIHYDRATE [MART.]
Common Name English
TEEBACIN
Brand Name English
PAS-C
Common Name English
AMINOSALICYLATE SODIUM [ORANGE BOOK]
Common Name English
AMINACYL
Brand Name English
Sodium aminosalicylate dihydrate [WHO-DD]
Common Name English
P-AMINOSALICYLIC ACID SODIUM SALT DIHYDRATE [MI]
Common Name English
AMINOSALICYLATE SODIUM [USP IMPURITY]
Common Name English
P-AMINOSALICYLIC ACID SODIUM SALT DIHYDRATE
MI  
Common Name English
PARA-AMINOSODIUM SALICYLATE
VANDF  
Common Name English
NSC-755862
Code English
SODIUM AMINOSALICYLATE DIHYDRATE [EP MONOGRAPH]
Common Name English
AMINOSALICYLATE SODIUM COMPONENT OF NEOPASALATE
Common Name English
PAMISYL SODIUM
Brand Name English
NEOPASALATE COMPONENT AMINOSALICYLATE SODIUM
Common Name English
SODIUM AMINOSALICYLATE DIHYDRATE [VANDF]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C280
Created by admin on Fri Dec 15 15:36:04 GMT 2023 , Edited by admin on Fri Dec 15 15:36:04 GMT 2023
WHO-ATC J04AA02
Created by admin on Fri Dec 15 15:36:04 GMT 2023 , Edited by admin on Fri Dec 15 15:36:04 GMT 2023
FDA ORPHAN DRUG 68592
Created by admin on Fri Dec 15 15:36:04 GMT 2023 , Edited by admin on Fri Dec 15 15:36:04 GMT 2023
WHO-VATC QJ04AA02
Created by admin on Fri Dec 15 15:36:04 GMT 2023 , Edited by admin on Fri Dec 15 15:36:04 GMT 2023
Code System Code Type Description
CAS
6018-19-5
Created by admin on Fri Dec 15 15:36:04 GMT 2023 , Edited by admin on Fri Dec 15 15:36:04 GMT 2023
PRIMARY
MERCK INDEX
m1743
Created by admin on Fri Dec 15 15:36:04 GMT 2023 , Edited by admin on Fri Dec 15 15:36:04 GMT 2023
PRIMARY Merck Index
ChEMBL
CHEMBL1169
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PRIMARY
RXCUI
89753
Created by admin on Fri Dec 15 15:36:04 GMT 2023 , Edited by admin on Fri Dec 15 15:36:04 GMT 2023
PRIMARY RxNorm
FDA UNII
S38B9W6AXW
Created by admin on Fri Dec 15 15:36:04 GMT 2023 , Edited by admin on Fri Dec 15 15:36:04 GMT 2023
PRIMARY
EVMPD
SUB12861MIG
Created by admin on Fri Dec 15 15:36:04 GMT 2023 , Edited by admin on Fri Dec 15 15:36:04 GMT 2023
PRIMARY
EVMPD
SUB21180
Created by admin on Fri Dec 15 15:36:04 GMT 2023 , Edited by admin on Fri Dec 15 15:36:04 GMT 2023
PRIMARY
PUBCHEM
16211148
Created by admin on Fri Dec 15 15:36:04 GMT 2023 , Edited by admin on Fri Dec 15 15:36:04 GMT 2023
PRIMARY
NCI_THESAURUS
C47958
Created by admin on Fri Dec 15 15:36:04 GMT 2023 , Edited by admin on Fri Dec 15 15:36:04 GMT 2023
PRIMARY
NSC
755862
Created by admin on Fri Dec 15 15:36:04 GMT 2023 , Edited by admin on Fri Dec 15 15:36:04 GMT 2023
PRIMARY
EPA CompTox
DTXSID5036638
Created by admin on Fri Dec 15 15:36:04 GMT 2023 , Edited by admin on Fri Dec 15 15:36:04 GMT 2023
PRIMARY
DRUG BANK
DBSALT001938
Created by admin on Fri Dec 15 15:36:04 GMT 2023 , Edited by admin on Fri Dec 15 15:36:04 GMT 2023
PRIMARY
SMS_ID
100000088683
Created by admin on Fri Dec 15 15:36:04 GMT 2023 , Edited by admin on Fri Dec 15 15:36:04 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
ANHYDROUS->SOLVATE
Related Record Type Details
ACTIVE MOIETY