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65-49-6 molecular structure
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4-amino-2-hydroxybenzoic acid

ChemBase ID: 118
Molecular Formular: C7H7NO3
Molecular Mass: 153.13538
Monoisotopic Mass: 153.04259309
SMILES and InChIs

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

Cite this record

CBID:118 http://www.chembase.cn/molecule-118.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
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
p-AMINOSALICYLIC ACID
4-Aminosalicylic acid
4-Aminosalicylic acid
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
4-Amino-2-hydroxybenzoic acid
Sanipirol-4
4-氨基-2-羟基苯甲酸
4-氨基水杨酸
CAS Number
65-49-6
EC Number
200-613-5
MDL Number
MFCD00007789
Beilstein Number
473071
Merck Index
14477
PubChem SID
24891299
46505572
160963581
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

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 3.6753502  H Acceptors
H Donor LogD (pH = 5.5) -0.8583485 
LogD (pH = 7.4) -2.2309935  Log P 0.8250751 
Molar Refractivity 39.9955 cm3 Polarizability 14.463896 Å3
Polar Surface Area 83.55 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 0.62  LOG S -1.11 
Solubility (Water) 1.18e+01 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
1690 mg/L expand Show data source
DMSO expand Show data source
Methanol expand Show data source
Apperance
Beige Solid expand Show data source
Melting Point
135-138°C expand Show data source
135-145 °C(lit.) expand Show data source
150°C expand Show data source
150°C (dec.) expand Show data source
150.5°C (302.9°F) expand Show data source
ca 135-145°C dec. expand Show data source
Hydrophobicity(logP)
1.6 expand Show data source
Storage Condition
Refrigerator expand Show data source
Room Temperature (15-30°C), Protect from light expand Show data source
Storage Warning
IRRITANT expand Show data source
Irritant/Store under Argon/Light Sensitive expand Show data source
RTECS
VO1225000 expand Show data source
European Hazard Symbols
Irritant Irritant (Xi) expand Show data source
Harmful Harmful (Xn) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
2 expand Show data source
Risk Statements
22-36 expand Show data source
36/37/38 expand Show data source
R:36 expand Show data source
Safety Statements
26 expand Show data source
26-37 expand Show data source
S:26 expand Show data source
S:36 expand Show data source
TSCA Listed
false expand Show data source
expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H315-H319-H335 expand Show data source
H319 expand Show data source
GHS Precautionary statements
P261-P305+P351+P338-P302+P352-P321-P405-P501A expand Show data source
P305 + P351 + P338 expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves expand Show data source
Admin Routes
Oral expand Show data source
Excretion
Renal expand Show data source
Metabolism
Hepatic expand Show data source
Protein Bound
50–60% expand Show data source
Legal Status
POM (UK) expand Show data source
Pregnancy Category
C expand Show data source
Gene Information
human ... PTPN1(5770) expand Show data source
Purity
95+% expand Show data source
98% expand Show data source
98+% expand Show data source
99% expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
Download expand Show data source
Linear Formula
H2NC6H3-2-(OH)CO2H expand Show data source

DETAILS

DETAILS

DrugBank DrugBank MP Biomedicals MP Biomedicals Sigma Aldrich Sigma Aldrich TRC TRC Wikipedia Wikipedia
DrugBank - DB00233 external link
Item Information
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
MP Biomedicals - 05213154 external link
MP Biomedicals Rare Chemical collection
MP Biomedicals - 02102573 external link
Free Acid
Crystalline
Purity: 99%
Sigma Aldrich - A79604 external link
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 external link
An antibiotic used to treat tuberculosis.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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)
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PATENTS

PATENTS

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INTERNET

INTERNET

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