AMINOSALICYLIC ACID

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)

HIDE SMILES / InChI

Molecular Formula	C7H7NO3
Molecular Weight	153.1354
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description

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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Dihydrofolate reductase 57	Inhibitor 8,297

Conditions

Condition	Modality	Highest Phase	Product
Tuberculosis 83	Primary	Approved 8,429	PASER
Crohn's disease 42	Primary	Phase II 1,132	PASER
Ulcerative colitis 123	Primary	Phase II 1,132	Unknown

C_max

Value	Dose	Analyte	Population
82.69 mg/L	8 g 1 times / day multiple, oral	AMINOSALICYLIC ACID plasma	Homo sapiens
53.63 mg/L	4 g 2 times / day multiple, oral	AMINOSALICYLIC ACID plasma	Homo sapiens
16.36 mg/L	8 g 1 times / day multiple, oral	4-ACETAMIDOSALICYLIC ACID plasma	Homo sapiens
14.59 mg/L	4 g 2 times / day multiple, oral	4-ACETAMIDOSALICYLIC ACID plasma	Homo sapiens
20 μg/mL	4 g single, oral	AMINOSALICYLIC ACID plasma	Homo sapiens

AUC

Value	Dose	Analyte	Population
690.35 mg × h/L	8 g 1 times / day multiple, oral	AMINOSALICYLIC ACID plasma	Homo sapiens
414.07 mg × h/L	4 g 2 times / day multiple, oral	AMINOSALICYLIC ACID plasma	Homo sapiens
142.49 mg × h/L	8 g 1 times / day multiple, oral	4-ACETAMIDOSALICYLIC ACID plasma	Homo sapiens
145.02 mg × h/L	4 g 2 times / day multiple, oral	4-ACETAMIDOSALICYLIC ACID plasma	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
1.62 h	4 g single, oral		AMINOSALICYLIC ACID plasma	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
45%	4 g single, oral		AMINOSALICYLIC ACID plasma	Homo sapiens

Doses

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Dose	Population	Adverse events
3 g 2 times / day multiple, oral Highest studied dose	unhealthy, 45.5	Disc. AE: Dyspepsia, Lipase increased...
4 g 3 times / day multiple, oral Recommended	unhealthy	Disc. AE: Drug-induced hepatitis...

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AEs

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AE	Significance	Dose	Population
Aspartate aminotransferase abnormal	4.3% Disc. AE	3 g 2 times / day multiple, oral Highest studied dose	unhealthy, 45.5
Lipase increased	4.3% Disc. AE	3 g 2 times / day multiple, oral Highest studied dose	unhealthy, 45.5
Dyspepsia	severe, 4.3% Disc. AE	3 g 2 times / day multiple, oral Highest studied dose	unhealthy, 45.5
Drug-induced hepatitis	0.5% Disc. AE	4 g 3 times / day multiple, oral Recommended	unhealthy

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
P-gp 1,461	P-gp 1,537 MRP1 107 OATP1B1 406 OCT1 327 OCT2 355 OAT1 326 OAT3 339

Drug as perpetrator

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Target	Modality	Activity	Metabolite	Clinical evidence
P-gp 1,650	inhibitor 3,277	yes [IC50 1.94 uM]

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Drug as victim

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Target	Modality	Activity
MRP1 107	substrate 3,367	yes
OAT1 326	substrate 3,367	yes
OAT3 339	substrate 3,367	yes
OATP1B1 406	substrate 3,367	yes
OCT1 327	substrate 3,367	yes

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
001 Chemical	NO22593	https://www.001chemical.com/chem/65-49-6
3B Scientific (Wuhan) Corp	3B3-030325	http://www.3bsc.com/index/pro_info.php?id=51589
AA Blocks	AA003KPD	https://www.aablocks.com/goods/Goods/detail?id=AA003KPD
Aaron Chemicals	AR003LH5	http://www.aaronchem.com/65-49-6
abcr GmbH	AB131475	http://www.abcr.com/shop/en/AB131475

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PubMed

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Title	Date	PubMed
[Inhibition of intestinal leukotriene formation as a possible mechanism of action of sulfasalazine, 5-aminosalicylic acid and 4-aminosalicylic acid].	1988 Nov 15	2907066

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