Aminosalicylic acid

First approved in 1948

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 Search

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)

HIDE SMILES / InChI

Description
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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Dihydrofolate reductase 61 Target ID: CHEMBL6065 Sources: http://www.jbc.org/content/288/32/23447.full.pdf+html	Inhibitor 8504

Conditions

Condition	Modality	Highest Phase	Product
Tuberculosis 83 Sources: http://www.rxlist.com/paser-drug.htm	Primary	Approved 8583	PASER Approved Use Tuberculosis Launch Date 1994
Crohn's disease 64 Sources: https://clinicaltrials.gov/ct2/show/NCT00495521	Primary	Phase II 1147	PASER Approved Use Unknown Launch Date 1994
Ulcerative colitis 125 Sources: https://clinicaltrials.gov/ct2/show/record/NCT00004810	Primary	Phase II 1147	Unknown Approved Use Unknown

C_max

Value	Dose	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 DRUG LABEL https://www.ema.europa.eu/en/documents/product-information/granupas-epar-product-information_en.pdf	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	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
1.62 h DRUG LABEL https://www.ema.europa.eu/en/documents/product-information/granupas-epar-product-information_en.pdf	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

F_unbound

Value	Dose	Co-administered	Analyte	Population
45% DRUG LABEL https://www.ema.europa.eu/en/documents/product-information/granupas-epar-product-information_en.pdf	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: https://pubmed.ncbi.nlm.nih.gov/9052519	unhealthy, 45.5 Health Status: unhealthy Age Group: 45.5 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/9052519	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: https://pubmed.ncbi.nlm.nih.gov/9052519
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: https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=6f2753dc-5f0c-4f49-9335-e519afb69ba6&type=display	unhealthy Health Status: unhealthy Sex: M+F Sources: https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=6f2753dc-5f0c-4f49-9335-e519afb69ba6&type=display	Disc. AE: Drug-induced hepatitis... AEs leading to discontinuation/dose reduction: Drug-induced hepatitis (0.5%) Sources: https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=6f2753dc-5f0c-4f49-9335-e519afb69ba6&type=display

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: https://pubmed.ncbi.nlm.nih.gov/9052519	unhealthy, 45.5 Health Status: unhealthy Age Group: 45.5 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/9052519
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: https://pubmed.ncbi.nlm.nih.gov/9052519	unhealthy, 45.5 Health Status: unhealthy Age Group: 45.5 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/9052519
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: https://pubmed.ncbi.nlm.nih.gov/9052519	unhealthy, 45.5 Health Status: unhealthy Age Group: 45.5 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/9052519
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: https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=6f2753dc-5f0c-4f49-9335-e519afb69ba6&type=display	unhealthy Health Status: unhealthy Sex: M+F Sources: https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=6f2753dc-5f0c-4f49-9335-e519afb69ba6&type=display

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
P-gp 1741	P-gp 2052 MRP1 113 OATP1B1 503 OCT1 393 OCT2 434 OAT1 395 OAT3 391

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
P-gp 1932	inhibitor 4027 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4261121/	yes [IC50 1.94 uM]

Drug as victim

Target	Modality	Activity
MRP1 113	substrate 4014 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4261121/	yes
OAT1 395	substrate 4014 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5404585/	yes
OAT3 391	substrate 4014 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5404585/	yes
OATP1B1 503	substrate 4014 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5404585/	yes
OCT1 393	substrate 4014 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5404585/	yes
OCT2 434	substrate 4014 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5404585/	yes
P-gp 2052	substrate 4014 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4261121/	yes

Sourcing

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
Acadechem	ACDS-017148	http://www.acadechemical.com/product/91847
Accela ChemBio Inc	SY001079	http://www.accelachem.com/cn/search.html?keyword=SY001079&attname=GoodsCode
Aceschem	ACS013053	https://www.aceschem.com/catalog/65-49-6.html
Achemica	ACMC-1BIVG	http://www.achemica.com/prodinfo/?id=54760
Achemo Scientific Limited	AC-22808	http://www.achemo.com/search/?Keyword= 65-49-6
Achemtek	0104-029388	http://www.achemtek.com/65-49-6
Acros Organics	AC104620050	https://www.fishersci.com/shop/products/4-aminosalicylic-acid-99-acros-organics/AC104620050
Acros Organics	AC104621000	https://www.fishersci.com/shop/products/4-aminosalicylic-acid-99-acros-organics/AC104621000
Acros Organics	AC104625000	https://www.fishersci.com/shop/products/4-aminosalicylic-acid-99-acros-organics/AC104625000
AHH Chemical co.,ltd	MT-01909	http://www.ahhchemical.com/product/MT-01909.html
AK Scientific, Inc. (AKSCI)	65768	http://www.aksci.com/item_detail.php?cat=65768
Alfa Aesar	B23289	https://www.alfa.com/en/catalog/B23289/
Alfa Chemistry	AP65496-A	https://reagents.alfa-chemistry.com/product/4-aminosalicylic-acid-cas-65-49-6-14694.html
Alfa Chemistry	AP65496-B	https://reagents.alfa-chemistry.com/product/aminosalicylic-acid-cas-65-49-6-14695.html
Ambinter	Amb1215242	http://www.ambinter.com/reference/1215242
Anward	ANW-35052	http://www.anward.com/pro_result/15246
Ark Pharm	AK-46320	http://www.arkpharminc.com/products/65-49-6.html
Aurora Fine Chemicals LLC	A00.158.421	http://online.aurorafinechemicals.com/info?ID=A00.158.421
Aurum Pharmatech LLC	H2354	http://www.Aurumpharmatech.com/Product/ProductDetails/H2354
Aurum Pharmatech LLC	M-5913	http://www.Aurumpharmatech.com/Product/ProductDetails/M_5913
Avantor Inc	101094-038	https://us.vwr.com/store/product/7889339/4-aminosalicylic-acid
Avantor Inc	200029-596	https://us.vwr.com/store/product/7513678/4-aminosalicylic-acid
BenchChem	B518644	https://www.benchchem.com/product/b518644
BioChemPartner	BCP18565	http://www.biochempartner.com/65-49-6-BCP18565
BioCrick	BCC8691	http://www.biocrick.com/4-Aminosalicylic-acid-BCC8691.html
BioSynth	Q-200437	https://www.biosynth.com/en/products/chemical-intermediates/basic-intermediates/products/Q-200437.html
BLD Pharm	BD94285	http://www.bldpharm.com/products/65-49-6.html
Boerchem	BC205364	http://www.boerchem.com/?product_34572.html
Capot Chemical	23542	http://www.capotchem.com/en/23542.htm
Capot Chemical	PubChem23542	http://www.capotchem.com/en/23542.htm
Chem Scene	CS-W023102	http://www.chemscene.com/65-49-6.html
Chemenu	CM110205	http://www.chemenu.com/products/CM110205
ChemFish Tokyo co.,ltd	4649	http://www.chemfish.co.jp/index.php?id=5063&project=product
ChemMol	30102576	http://www.chemmol.com/chemmol/30102576.html
ChemMol	44002107	http://www.chemmol.com/chemmol/44002107.html
ChemMol	99122203	http://www.chemmol.com/chemmol/99122203.html
Chemspace	CSSB00000185803	https://chem-space.com/CSSB00000185803
Clearsynth	CS-T-03461	https://www.clearsynth.com/en/CST03461.html
CSNpharm	CSN23620	https://www.csnpharm.com/products/4-aminosalicylic-acid.html
Debye Scientific	DB-054818	http://www.debyesci.com/cas_65-49-6.html
Enamine	Z90121065	https://www.enaminestore.com/catalog/Z90121065
eNovation Chemicals	D379680	http://www.enovationchem.com/productDetails.asp?productID=D379680
eNovation Chemicals	D401935	https://www.enovationchem.com/ProductDetails.asp?ProductID=D401935
eNovation Chemicals	D590479	https://enovationchem.com/ProductDetails.asp?ProductID=D590479
eNovation Chemicals	D669867	https://www.enovationchem.com/ProductDetails.asp?ProductID=D669867
Finetech	FT-0617609	http://www.finetechnology-ind.com/prod/detail/pub/65-49-6.html
Finetech	FT-0689453	http://www.finetechnology-ind.com/prod/detail/pub/133-15-3.html
Glentham Life Sciences	GM8827	http://www.glentham.com/products/product/GM8827/
Hairui	HR133954	http://www.hairuichem.com/en/product/65-49-6.html
Lab Network	LN00175003	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00175003
LGC Standards	DRE-C10227010	https://www.lgcstandards.com/US/en/p/DRE-C10227010
Matrix Scientific	75166	https://www.matrixscientific.com/075166.html
mcule	MCULE-4841633599	https://mcule.com/MCULE-4841633599/
MedChem Express	HY-I0447	https://www.medchemexpress.com/4-aminosalicylic-acid.html
Molcore	CS22593	https://www.molcore.com/product/65-49-6
Oakwood	78671	http://www.oakwoodchemical.com/ProductsList.aspx?CategoryID=-2&txtSearch=63845&ExtHyperLink=1
Otava	2829520	https://search.otavachemicals.com/#!/search?query=2829520&type=code&base=dbb
Parchem	2487	http://www.parchem.com/chemical-supplier-distributor/4-amino-Salicylic-acid-004064.aspx
Parchem	31862	http://www.parchem.com/chemical-supplier-distributor/Salicylic-Acid-USP-021862.aspx
Renno Tech	RP21704	http://www.rennotech.com/product_show.asp?id=27414
Sigma-Aldrich	1026401_USP	https://www.sigmaaldrich.com/catalog/product/usp/1026401?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	A79604_ALDRICH	https://www.sigmaaldrich.com/catalog/product/aldrich/a79604?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	PHR1746_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/phr1746?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	V900740_VETEC	https://www.sigmaaldrich.com/catalog/product/vetec/v900740?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sinfoo Biotech	S001491	http://www.sinfoobiotech.com/product/1004889
Smolecule	S518644	http://www.smolecule.com/products/s518644
TCI (Tokyo Chemical Industry)	A0420	http://www.tcichemicals.com/eshop/en/us/commodity/A0420/index.html
THE BioTek	bt-259572	https://www.thebiotek.com/product/inhibitors/bt-259572
Vitas-M Laboratory	BBL013175	http://www.request.vitasmlab.biz/index.php?option=com_search_stk&Itemid=22&stk=BBL013175&?utm_source=pubchem&utm_medium=p_search_link&utm_campaign=pubchem_search&utm_content=pubchem_slink
VladaChem	VL264995-100G	https://www.vladachem.com/product.php?products=65-49-6
Yuhao Chemical	XJ0046	http://www.chemyuhao.com/65-49-6.html

PubMed

Title	Date	PubMed
Tuberculostatic derivatives of rho-aminobenzoic acid; esters and amides of 4-aminosalicylic acid.	1948	18098531
A procedure for the determination of 4-aminosalicylic acid (p-aminosalicylic acid) in blood and in urine.	1949 Feb	18123816

Patents

Sample Use Guides

In Vivo Use Guide

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

5.0 ug/mL MIC against mycobacterium tuberculosis.

Name

Type

Language

Aminosalicylic acid

Systematic Name

English

P-AMINOSALICYLIC ACID

Preferred 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 [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