AMINOSALICYLATE SODIUM

First approved in 1948

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 Search

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

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 57 Target ID: CHEMBL6065 Sources: http://www.jbc.org/content/288/32/23447.full.pdf+html	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Tuberculosis 83 Sources: http://www.rxlist.com/paser-drug.htm	Primary	Approved 8429	PASER Approved Use Tuberculosis Launch Date 1994
Crohn's disease 42 Sources: https://clinicaltrials.gov/ct2/show/NCT00495521	Primary	Phase II 1132	PASER Approved Use Unknown Launch Date 1994
Ulcerative colitis 123 Sources: https://clinicaltrials.gov/ct2/show/record/NCT00004810	Primary	Phase II 1132	Unknown Approved Use Unknown

C_max

Value	Dose	Analyte	Population
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
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
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
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

AUC

Value	Dose	Analyte	Population
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
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
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 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: https://pubmed.ncbi.nlm.nih.gov/9052519 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: https://pubmed.ncbi.nlm.nih.gov/9052519 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: https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=6f2753dc-5f0c-4f49-9335-e519afb69ba6&type=display	unhealthy n = 7492 Health Status: unhealthy Condition: Tuberculosis Sex: M+F Population Size: 7492 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 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: https://pubmed.ncbi.nlm.nih.gov/9052519 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: https://pubmed.ncbi.nlm.nih.gov/9052519 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: https://pubmed.ncbi.nlm.nih.gov/9052519 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: https://pubmed.ncbi.nlm.nih.gov/9052519 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: https://pubmed.ncbi.nlm.nih.gov/9052519 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: https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=6f2753dc-5f0c-4f49-9335-e519afb69ba6&type=display	unhealthy n = 7492 Health Status: unhealthy Condition: Tuberculosis Sex: M+F Population Size: 7492 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 1461	P-gp 1537 MRP1 107 OATP1B1 406 OCT1 327 OCT2 355 OAT1 326 OAT3 339

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
P-gp 1650	inhibitor 3277 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4261121/	yes [IC50 1.94 uM]

Drug as victim

Target	Modality	Activity
MRP1 107	substrate 3367 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4261121/	yes
OAT1 326	substrate 3367 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5404585/	yes
OAT3 339	substrate 3367 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5404585/	yes
OATP1B1 406	substrate 3367 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5404585/	yes
OCT1 327	substrate 3367 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5404585/	yes
OCT2 355	substrate 3367 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5404585/	yes
P-gp 1537	substrate 3367 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
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
Aaron Chemicals	AR003LH5	http://www.aaronchem.com/65-49-6
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
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	200029-596	https://us.vwr.com/store/product/7513678/4-aminosalicylic-acid
Avantor Inc	101094-038	https://us.vwr.com/store/product/7889339/4-aminosalicylic-acid
BLD Pharm	BD94285	http://www.bldpharm.com/products/65-49-6.html
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
Boerchem	BC205364	http://www.boerchem.com/?product_34572.html
CSNpharm	CSN23620	https://www.csnpharm.com/products/4-aminosalicylic-acid.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
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
Chemenu	CM110205	http://www.chemenu.com/products/CM110205
Chemspace	CSSB00000185803	https://chem-space.com/CSSB00000185803
Clearsynth	CS-T-03461	https://www.clearsynth.com/en/CST03461.html
Debye Scientific	DB-054818	http://www.debyesci.com/cas_65-49-6.html
Enamine	Z90121065	https://www.enaminestore.com/catalog/Z90121065
Finetech	FT-0689453	http://www.finetechnology-ind.com/prod/detail/pub/133-15-3.html
Finetech	FT-0617609	http://www.finetechnology-ind.com/prod/detail/pub/65-49-6.html
Glentham Life Sciences	GM8827	http://www.glentham.com/products/product/GM8827/
Hairui	HR133954	http://www.hairuichem.com/en/product/65-49-6.html
LGC Standards	DRE-C10227010	https://www.lgcstandards.com/US/en/p/DRE-C10227010
Lab Network	LN00175003	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00175003
Matrix Scientific	75166	https://www.matrixscientific.com/075166.html
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	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	1026401_USP	https://www.sigmaaldrich.com/catalog/product/usp/1026401?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
abcr GmbH	AB131475	http://www.abcr.com/shop/en/AB131475
eNovation Chemicals	D379680	http://www.enovationchem.com/productDetails.asp?productID=D379680
eNovation Chemicals	D590479	https://enovationchem.com/ProductDetails.asp?ProductID=D590479
eNovation Chemicals	D401935	https://www.enovationchem.com/ProductDetails.asp?ProductID=D401935
eNovation Chemicals	D669867	https://www.enovationchem.com/ProductDetails.asp?ProductID=D669867
mcule	MCULE-4841633599	https://mcule.com/MCULE-4841633599/

PubMed

Title	Date	PubMed
Treatment of left-sided ulcerative colitis with 4-aminosalicylic acid enemas. A double-blind, placebo-controlled trial.	1988 Feb	3277506
A prospective randomized double blind trial comparing prednisolone and 4-aminosalicylic acid enemas in acute distal ulcerative colitis.	1992 Mar-Apr	1571500
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	7926910

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

AMINOSALICYLATE SODIUM

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

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

Common Name

English

PARA-AMINOSODIUM SALICYLATE

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