4-amino-2-hydroxybenzoic acid

• ChemBase ID: 118
• Molecular Formular: C7H7NO3
• Molecular Mass: 153.13538
• Monoisotopic Mass: 153.04259309
• SMILES: Oc1c(ccc(N)c1)C(=O)O
• Canonical SMILES: Nc1ccc(c(c1)O)C(=O)O
• InChI: InChI=1S/C7H7NO3/c8-4-1-2-5(7(10)11)6(9)3-4/h1-3,9H,8H2,(H,10,11)
• InChIKey: WUBBRNOQWQTFEX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-amino-2-hydroxybenzoic acid
• IUPAC Traditional name: aminosalicylic acid
• Brand Name: Aminopar; Aminox; Apacil; Deapasil; Entepas; Ferrosan; Gabbropas; Hellipidyl; Kyselina P-Aminosalicylova; Neopasalate; Osacyl; PAS-C; Pamacyl; Pamisyl; Para-Pas; Paramycin; Parasal; Parasalicil; Parasalindon; Pasa; Pasalon; Pasara; Pascorbic; Pasdium; Pasem; Paser; Pasmed; Pasnodia; Pasolac; Propasa; Rezipas; Sanipirol-4; Sanipriol-4
• Synonyms: 4-Amino-2-hydroxy-benzoic Acid; 3-Hydroxy-4-carboxyaniline; 4-Carboxy-3-hydroxyaniline; Apacil; Deapasil; Entepas; Gabbropas; Monopass; NSC 2083; NSC 211698; Paramycin; Parasal; Parasalicil; Parasalindon; Pasa; Pasalon; Pasara; Pasem; Paser; Pasmed; Pasnodia; Pasolac; Propasa; Rezipas; Sanipirol-4; 4-Aminosalicylic acid; 4-Aminosalicylic acid; Aminosalicylate Sodium; P-Aminosalicylic Acid; Para-Amino Salicylic Acid; PAS; Para-aminosalicylic acid; 4-aminosalicylic acid; 4-ASA; Amino-PAS; APAS; PASK; Aminosalicylic Acid; 4-Amino-2-hydroxybenzoic acid; 4-Amino-2-hydroxybenzoic acid; p-AMINOSALICYLIC ACID; 4-氨基-2-羟基苯甲酸; 4-氨基水杨酸

Database IDs

• CAS Number: 65-49-6
• EC Number: 200-613-5
• MDL Number: MFCD00007789
• Beilstein Number: 473071
• Merck Index: 14477
• PubChem SID: 24891299; 160963581; 46505572
• PubChem CID: 4649
• CHEBI ID: 27565
• ATC CODE: J04AA01
• CHEMBL: 1169
• Chemspider ID: 4488
• DrugBank ID: DB00233
• KEGG ID: D00162
• Unique Ingredient Identifier: 5B2658E0N2
• Wikipedia Title: 4-Aminosalicylic_acid

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.6753502
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -0.8583485
• LogD (pH = 7.4): -2.2309935
• Log P: 0.8250751
• Molar Refractivity: 39.9955 cm^3
• Polarizability: 14.463896 Å^3
• Polar Surface Area: 83.55 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.62
• LOG S: -1.11
• Solubility (Water): 1.18e+01 g/l

PROPERTIES

Physical Property

• Solubility: 1690 mg/L; DMSO; Methanol
• Apperance: Beige Solid
• Melting Point: 135-138°C; 135-145 °C(lit.); 150°C; 150°C (dec.); 150.5°C (302.9°F); ca 135-145°C dec.
• Hydrophobicity(logP): 1.6

Safety Information

• Storage Condition: Refrigerator; Room Temperature (15-30°C), Protect from light
• Storage Warning: IRRITANT; Irritant/Store under Argon/Light Sensitive
• RTECS: VO1225000
• European Hazard Symbols: Irritant (Xi); Harmful (Xn)
• German water hazard class: 2
• Risk Statements: 22-36; 36/37/38; R:36
• Safety Statements: 26; 26-37; S:26; S:36
• TSCA Listed: false; 是
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335; H319
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A; P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Pharmacology Properties

• Admin Routes: Oral
• Excretion: Renal
• Metabolism: Hepatic
• Protein Bound: 50–60%
• Legal Status: POM (UK)
• Pregnancy Category: C
• Gene Information: human ... PTPN1(5770)

Product Information

• Purity: 95+%; 98%; 98+%; 99%
• Linear Formula: H2NC6H3-2-(OH)CO2H

DETAILS

MP Biomedicals - 02102573

Free Acid
Crystalline
Purity: 99%

MP Biomedicals - 05213154

MP Biomedicals Rare Chemical collection

DrugBank - DB00233

• Drug Groups: approved
• Description: An antitubercular agent often administered in association with isoniazid. The sodium salt of the drug is better tolerated than the free acid. [PubChem]
• Indication: For the treatment of tuberculosis
• Pharmacology: Aminosalicylic acid is an anti-mycobacterial agent used with other anti-tuberculosis drugs (most often isoniazid) for the treatment of all forms of active tuberculosis due to susceptible strains of tubercle bacilli. The two major considerations in the clinical pharmacology of aminosalicylic acid are the prompt production of a toxic inactive metabolite under acid conditions and the short serum half life of one hour for the free drug. Aminosalicylic acid is bacteriostatic against Mycobacterium tuberculosis (prevents the multiplying of bacteria without destroying them). It also inhibits the onset of bacterial resistance to streptomycin and isoniazid.
• Toxicity: LD₅₀=4 gm/kg (orally in mice); LD₅₀=3650 mg/kg (orally in rabbits)
• Affected Organisms: Mycobacteria
• Biotransformation: Hepatic.
• Protein Binding: 50-60%
• External Links: Wikipedia; RxList; Drugs.com

Sigma Aldrich - A79604

Packaging
5, 100, 500 g in glass bottle
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. A79604.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Toronto Research Chemicals - A629220

An antibiotic used to treat tuberculosis.

REFERENCES

• Horita, Y., et al.: Bioorg. Med. Chem. Lett., 19, 6313 (2009)
• Martins, M., et al.: J. Biol. Chem., 284, 18726 (2009)
• Fourches, D., et al.: Chem. Res. Toxicol., 23, 171 (2009)