ANTHRANILIC ACID

Details

Stereochemistry	ACHIRAL
Molecular Formula	C7H7NO2
Molecular Weight	137.136
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NC1=CC=CC=C1C(O)=O

InChI

InChIKey=RWZYAGGXGHYGMB-UHFFFAOYSA-N

InChI=1S/C7H7NO2/c8-6-4-2-1-3-5(6)7(9)10/h1-4H,8H2,(H,9,10)

HIDE SMILES / InChI

Description
Sources: http://www.dailyhealthmagazine.com/vitamin-l1/https://www.drugs.com/inactive/aminobenzoate-sodium-185.html
Curator's Comment: description was created based on several sources, including: DOI: 10.2174/157017906777934926 | https://www.ncbi.nlm.nih.gov/pubmed/12844171

Sodium anthranilate is an excipient (pharmacologically inactive substance). Sodium anthranilate (Aminobenzoate sodium ,C7H6NNaO2), also known as sodium 2-aminobenzoate, is an organic amine. Aminobenzoate sodium exists as a yellow powder for use in pharmaceutical processing.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Anthranilate hydroxylase 4 Target ID: Anthranilate hydroxylase Sources: http://www.genome.jp/dbget-bin/www_bget?ec:1.14.16.3	Substrate 661

Conditions

Condition	Modality	Highest Phase	Product
Obesity 206 Sources: https://www.drugs.com/imprints/ov-12-6970.html	Inactive ingredient	Approved 8583	Desoxyn Approved Use Desoxyn is used in the treatment of adhd; obesity and belongs to the drug classes anorexiants, CNS stimulants. Launch Date 1943
Intractable epilepsy 4 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25022821	Diagnostic	Natural Metabolite	Unknown Approved Use Unknown
Schizophrenia 305 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27042691	Diagnostic	Natural Metabolite	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Production and analysis of organic acids in hairy-root cultures of Isatis indigotica Fort. (indigo woad).	2004-02	12962543
Probing cathepsin K activity with a selective substrate spanning its active site.	2003-10-15	12837132
Waste-free and facile solid-state protection of diamines, anthranilic acid, diols, and polyols with phenylboronic acid.	2003-09-05	12953200
A concise total synthesis of (+/-)-alantrypinone by a novel hetero-Diels-Alder reaction.	2003-09-04	12943388
Subsite specificity (S3, S2, S1', S2' and S3') of oligopeptidase B from Trypanosoma cruzi and Trypanosoma brucei using fluorescent quenched peptides: comparative study and identification of specific carboxypeptidase activity.	2003-08-01	12737623
S3 to S3' subsite specificity of recombinant human cathepsin K and development of selective internally quenched fluorescent substrates.	2003-08-01	12733990
Gene cluster of Arthrobacter ilicis Ru61a involved in the degradation of quinaldine to anthranilate: characterization and functional expression of the quinaldine 4-oxidase qoxLMS genes.	2003-07-25	12730200
Human recombinant endopeptidase PHEX has a strict S1' specificity for acidic residues and cleaves peptides derived from fibroblast growth factor-23 and matrix extracellular phosphoglycoprotein.	2003-07-01	12678920
A quasi-tetrahedral Cu4 cluster and a helical-chain copper (II) complex with single syn-anti carboxylate bridges: crystal structure and magnetic properties.	2003-06-30	12817958
A novel vascular endothelial growth factor-directed therapy that selectively activates cytotoxic prodrugs.	2003-05-19	12771932
Specificity of S'1 and S'2 subsites of human tissue kallikrein using the reactive-centre loop of kallistatin: the importance of P'1 and P'2 positions in design of inhibitors.	2003-05-01	12578561
Complexity of coordinative bonding in thallium(I) anthranilates and salicylates.	2003-03-26	12643725
Conjugate additions of o-iodoanilines and methyl anthranilates to acetylenic sulfones. A new route to quinolones including first syntheses of two alkaloids from the medicinal herb Ruta chalepensis.	2003-03-21	12636385
Anthranilic acid derivatives: a new class of non-peptide CCK1 receptor antagonists.	2003-03-06	12538004
Separation of saccharides derivatized with 2-aminobenzoic acid by capillary electrophoresis and their structural consideration by nuclear magnetic resonance.	2003-03-01	12633611
Construction and complementation of the first auxotrophic mutant in the spirochaete Leptospira meyeri.	2003-03	12634337
Glucose conjugation of anthranilate by the Arabidopsis UGT74F2 glucosyltransferase is required for tryptophan mutant blue fluorescence.	2003-02-21	12475971
Structure-activity relationships of substituted benzothiophene-anthranilamide factor Xa inhibitors.	2003-02-10	12565961
High-performance liquid chromatography assay for 1-deoxy-D-xylulose 5-phosphate synthase activity using fluorescence detection.	2003-02-07	12597635
Complete nucleotide sequence of carbazole/dioxin-degrading plasmid pCAR1 in Pseudomonas resinovorans strain CA10 indicates its mosaicity and the presence of large catabolic transposon Tn4676.	2003-02-07	12547188
Avenanthramides in oats (Avena sativa L.) and structure-antioxidant activity relationships.	2003-01-29	12537428
Total synthesis of (-)-fumiquinazolines A, B, C, E, H, and I. Approaches to the synthesis of fiscalin A.	2003-01-24	12530882
Kynurenines and the respiratory parameters on rat heart mitochondria.	2003-01-24	12505541
Peptides to peptidomimetics: towards the design and synthesis of bioavailable inhibitors of oligosaccharyl transferase.	2003-01-07	12929394
Allergic contact dermatitis from etofenamate without cross-sensitization to other anthranilic acid derivatives.	2003	12771478
Lateral gene transfer and ancient paralogy of operons containing redundant copies of tryptophan-pathway genes in Xylella species and in heterocystous cyanobacteria.	2003	12620124
Anthranilic acid amides: a novel class of antiangiogenic VEGF receptor kinase inhibitors.	2002-12-19	12477352
Ortho-aminobenzoic acid-labeled bradykinins in interaction with lipid vesicles: fluorescence study.	2002-12-05	12389213
Location of abasic sites in oligodeoxynucleotides by tandem mass spectrometry and by a chemical cleavage initiated by an unusual reaction of the ODN with MALDI matrix.	2002-12	12484461
Yeast D-amino acid oxidase: structural basis of its catalytic properties.	2002-11-29	12445787
Cathepsin B carboxydipeptidase specificity analysis using internally quenched fluorescent peptides.	2002-11-15	12201820
Synthesis, analgesic, anti-inflammatory and antibacterial activities of some novel 2-phenyl-3-substituted quinazolin-4(3H) ones.	2002-11	12419954
An improved synthesis of 5,6-dimethylxanthenone-4-acetic acid (DMXAA).	2002-10	12446040
Temperature and salts effects on the peptidase activities of the recombinant metallooligopeptidases neurolysin and thimet oligopeptidase.	2002-09	12199711
Dynamic diversity of the tryptophan pathway in chlamydiae: reductive evolution and a novel operon for tryptophan recapture.	2002-08-29	12225590
Newer N-substituted anthranilic acid derivatives as potent anti-inflammatory agents.	2002-08	12161066
The crystal structure of anthranilate phosphoribosyltransferase from the enterobacterium Pectobacterium carotovorum.	2002-07-17	12123839
Modification of carbon nanofibres for the immobilization of metal complexes: a case study with rhodium and anthranilic acid.	2002-07-02	12489215
Role of rhizobial biosynthetic pathways of amino acids, nucleotide bases and vitamins in symbiosis.	2002-07	12597544
Characterization of Trp(+) reversions in Escherichia coli strain WP2uvrA.	2002-07	12110627
Biosynthesis of nodulisporic acid A: precursor studies.	2002-06-19	12059229
Tranilast prevents activation of transforming growth factor-beta system, leukocyte accumulation, and neointimal growth in porcine coronary arteries after stenting.	2002-06-01	12067902
[Structural variation of o-amino-benzoic acid induced by free electron laser].	2002-06	12938310
Effects of fatty liver induced by niacin-free diet with orotic acid on the metabolism of tryptophan to niacin in rats.	2002-06	12162538
Toxicology and carcinogenesis studies of o-nitrotoluene sulfone (CAS no. 88-72-2) in F344/N rats and B6C3F(1) mice (feed studies).	2002-05	12087420
Photocyclization of N,N-phthaloylanthranilic amides coupled to omega-amino acids with increasing chain lengths.	2002-04	12661962
Tranilast slows the progression of advanced diabetic nephropathy.	2002	12372957
Update on sensitivity to nonsteroidal antiinflammatory drugs.	2001-11	12477289
Accumulation of toxic products degradation of kynurenine in hemodialyzed patients.	2001	12092667
Research on tryptophan metabolites "via kynurenine" in epidermis of man and mouse.	1975	1244085

Patents

Sample Use Guides

In Vivo Use Guide

15,000 or 30,000 ppm for the rats, and either 25,000 or 50,000 ppm for the mice, 5 days per week for 78 weeks

Route of Administration: Oral

In Vitro Use Guide

The DNA damage effects of tryptophan metabolites were analyzed using plasmid relaxation assay performed with anthranilic acid at various concentrations between 50 uM and 400 uM in the presence of plasmid DNA pSP-72. Anthranilic acid did not show any plasmid relaxation activity.

Name

Type

Language

O-AMINOBENZOIC ACID

Preferred Name

English

ANTHRANILIC ACID

Systematic Name

English

NSC-40929

Code

English

Anthranilic acid [WHO-DD]

Common Name

English

NSC-144

Code

English

VITAMIN L1

Common Name

English

NCI-C01730

Code

English

ANTHRANILIC ACID [HSDB]

Common Name

English

BENZOIC ACID, 2-AMINO-

Common Name

English

2-AMINOBENZOIC ACID

Systematic Name

English

O-CARBOXYANILINE

Common Name

English

BENZOIC ACID, O-AMINO-

Common Name

English

ANTHRANILIC ACID [IARC]

Common Name

English

O-ANTHRANILIC ACID

Common Name

English

O-AMINOBENZOIC ACID [MI]

Common Name

English

1-AMINO-2-CARBOXYBENZENE

Systematic Name

English

2-CARBOXYANILINE

Systematic Name

English

Classification Tree Code System Code

DEA NO.

8530