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Details

Stereochemistry ACHIRAL
Molecular Formula 2C7H5NO3.2Ca.7H2O
Molecular Weight 508.502
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CALCIUM PARAAMINOSALICYLATE HEMIHEPTAHYDRATE

SMILES

O.O.O.O.O.O.O.[Ca++].[Ca++].NC1=CC([O-])=C(C=C1)C([O-])=O.NC2=CC([O-])=C(C=C2)C([O-])=O

InChI

InChIKey=TVYXYAYUKBKYKY-UHFFFAOYSA-J
InChI=1S/2C7H7NO3.2Ca.7H2O/c2*8-4-1-2-5(7(10)11)6(9)3-4;;;;;;;;;/h2*1-3,9H,8H2,(H,10,11);;;7*1H2/q;;2*+2;;;;;;;/p-4

HIDE SMILES / InChI

Molecular Formula Ca
Molecular Weight 40.078
Charge 2
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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 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
Treatment of left-sided ulcerative colitis with 4-aminosalicylic acid enemas. A double-blind, placebo-controlled trial.
1988 Feb
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
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 Sat Dec 16 05:35:26 GMT 2023
Edited
by admin
on Sat Dec 16 05:35:26 GMT 2023
Record UNII
EWZ8PD068X
Record Status Validated (UNII)
Record Version
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Name Type Language
CALCIUM PARAAMINOSALICYLATE HEMIHEPTAHYDRATE
Common Name English
CALCIUM PARAAMINOSALICYLATE HYDRATE [JAN]
Common Name English
MONOCALCIUM 4-AMINO-2-OXIDOBENZOATE HEMIHEPTAHYDRATE
Common Name English
BENZOIC ACID, 4-AMINO-2-HYDROXY-, CALCIUM SALT, HYDRATE (2:2:7)
Common Name English
Code System Code Type Description
CAS
1374221-08-5
Created by admin on Sat Dec 16 05:35:26 GMT 2023 , Edited by admin on Sat Dec 16 05:35:26 GMT 2023
PRIMARY
EPA CompTox
DTXSID80160176
Created by admin on Sat Dec 16 05:35:26 GMT 2023 , Edited by admin on Sat Dec 16 05:35:26 GMT 2023
PRIMARY
PUBCHEM
11954342
Created by admin on Sat Dec 16 05:35:26 GMT 2023 , Edited by admin on Sat Dec 16 05:35:26 GMT 2023
PRIMARY
FDA UNII
EWZ8PD068X
Created by admin on Sat Dec 16 05:35:26 GMT 2023 , Edited by admin on Sat Dec 16 05:35:26 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
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ACTIVE MOIETY