5-amino-2-hydroxybenzoic acid

• ChemBase ID: 129
• Molecular Formular: C7H7NO3
• Molecular Mass: 153.13538
• Monoisotopic Mass: 153.04259309
• SMILES: Oc1c(cc(N)cc1)C(=O)O
• Canonical SMILES: Nc1ccc(c(c1)C(=O)O)O
• InChI: InChI=1S/C7H7NO3/c8-4-1-2-6(9)5(3-4)7(10)11/h1-3,9H,8H2,(H,10,11)
• InChIKey: KBOPZPXVLCULAV-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-amino-2-hydroxybenzoic acid
• IUPAC Traditional name: 5-amino-2-hydroxybenzoic acid; mesalazine
• Brand Name: Asacol; Asacolitin; Canasa; Claversal; Fisalamine; Lixacol; Mesasal; Pentasa; Rowasa; Salofalk
• Synonyms: Fisalamine; Asacolitin; Claversal; Mesasal; Pentasa; 5-Amino-2-hydroxybenzoic acid 97%; 5-Amino-2-hydroxybenzoic acid; Mesalamine; Asalit; Rowasa; Salofalk; Mesalazine; 5-aminosalicylate; 5-aminosalicylic acid; 5-ASA; Mesalamine; Mesalazine; 5-aminosalicylic acid; Mesalazine; Asacol; P; Mesalamine; 5-AS; 5-Aminosalicylic acid; 5-Amino-2-hydroxybenzoic acid; 5-AMINOSALICYLIC ACID; 5-氨基水杨酸; 氨水杨酸; 5-氨基-2-羟基苯甲酸; 氨水杨酸; 5-氨基水杨酸

Database IDs

• CAS Number: 89-57-6
• EC Number: 201-919-1
• MDL Number: MFCD00007877
• Beilstein Number: 2090421
• Merck Index: 145904
• PubChem SID: 24891301; 46509142; 160963592; 24846332; 24891065; 24846331; 24890780
• PubChem CID: 4075

CALCULATED PROPERTIES

JChem

• Acid pKa: 2.0241883
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -0.43266416
• LogD (pH = 7.4): -1.7183259
• Log P: -0.2897824
• Molar Refractivity: 39.9955 cm^3
• Polarizability: 14.463507 Å^3
• Polar Surface Area: 83.55 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.75
• LOG S: -1.1
• Solubility (Water): 1.22e+01 g/l

PROPERTIES

Physical Property

• Solubility: 0.84 g/L at 20°C; DMSO
• Apperance: dark gray to brown powder; off-white to gray powder; Off-White to Pale Beige Solid; tablet; tablets
• Melting Point: >250°C (dec); 275-280 °C (dec.)(lit.); 280(dec.); 280(dec.)°C; ca 280°C dec.
• Hydrophobicity(logP): 1.2
• pH: 4.5-5.5 (25 °C, 1 tablet in 100 ml H2O)

Safety Information

• Storage Condition: -20°C; -20°C Freezer; 2-8°C
• Storage Warning: IRRITANT; Irritant
• RTECS: VO1400000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 2
• Risk Statements: 36/37/38
• Safety Statements: 26-36; 26-37
• TSCA Listed: false; 是
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335; H315-H319-H335-H303
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Pharmacology Properties

• Mechanism of Action: Cyclooxygenase inhibitor; Prostaglandin antagonist

Product Information

• Purity: ≥95% (NT); ≥97.0% (NT); ≥99%; 95%; 97%; 99%
• Concentration: ~100 mg/tablet (enzym.)
• Grade: purum; technical
• Salt Data: Free Base
• Application(s): Antiinflammatory agent; Antiseptic; Drug used for treatment of ulcerative colitis; Esters used as sunscreens; Low acute oral toxicity
• Pharmacopeia Traceability: traceable to PhEur Y0000297; traceable to USP 1392705
• Linear Formula: H2NC6H3-2-(OH)CO2H

DETAILS

MP Biomedicals - 02154770

(5-Amino-2-hydroxybenzoic acid) Purity: 99% Off-white to gray powder.

MP Biomedicals - 05215090

MP Biomedicals Rare Chemical collection

DrugBank - DB00244

• Drug Groups: approved
• Description: An anti-inflammatory agent, structurally related to the salicylates, which is active in inflammatory bowel disease. It is considered to be the active moiety of sulphasalazine. (From Martindale, The Extra Pharmacopoeia, 30th ed)
• Indication: For the treatment of active ulcerative proctitis.
• Pharmacology: Mesalazine (INN, BAN), also known as Mesalamine (USAN) or 5-aminosalicylic acid (5-ASA), is an anti-inflammatory drug used to treat inflammation of the digestive tract (Crohn's disease) and mild to moderate ulcerative colitis. Mesalazine is a bowel-specific aminosalicylate drug that is metabolized in the gut and has its predominant actions there, thereby having fewer systemic side effects. As a derivative of salicylic acid, 5-ASA is also an antioxidant that traps free radicals, which are potentially damaging by-products of metabolism.
• Toxicity: Oral, mouse: LD₅₀ = 3370 mg/kg; Oral, rat: LD₅₀ = 2800 mg/kg; Skin, rabbit: LD₅₀ = >5 gm/kg. There have been no documented reports of serious toxicity in man resulting from massive overdosing with mesalamine. Under ordinary circumstances, mesalazine absorption from the colon is limited.
• Affected Organisms: Humans and other mammals
• Biotransformation: Rapidly and extensively metabolized, mainly to N-acetyl-5-ASA (Ac-5-ASA) in the intestinal mucosal wall and the liver. Ac-5-ASA is further acetylated (deactivated) in at least 2 sites, the colonic epithelium and the liver.
• Absorption: 20 to 30% absorbed following oral administration. 10 to 35% absorbed from the colon (rectal suppository) - extent of absorption is determined by the length of time the drug is retained in the colon.
• Half Life: The mean elimination half-life was 5 hours for 5-ASA and six hours for N-acetyl-5-ASA following the initial dose. At steady state, the mean elimination half-life was seven hours for both 5-ASA and N-acetyl-5-ASA.
• Protein Binding: About 80% of N-Ac-5-ASA is bound to plasma proteins, whereas 40% of mesalamine is protein bound.
• Elimination: Approximately 28% of the mesalamine in Asacol tablets is absorbed after oral ingestion, leaving the remainder available for topical action and excretion in the feces.; It is excreted mainly by the kidney as N-acetyl-5-aminosalicylic acid.
• References: [Link]
• External Links: Wikipedia; RxList; PDRhealth

Selleck Chemicals - S1681

Research Area: Inflammation
Biological Activity:
Mesalamine (Lialda, Apriso) is an anti-inflammatory compound used to treat inflammation of the digestive tract ulcerative colitis and mild-to-moderate Crohn’s disease. Mesalamine (Lialda, Apriso) is a bowel-specific aminosalicylate drug that acts locally in the gut and has its predominant actions there, thereby having few systemic side effects. As a derivative of salicylic acid, 5-ASA is also thought to be an antioxidant that traps free radicals, which are potentially damaging byproducts of metabolism. [1]

Sigma Aldrich - A6178

Application
5-氨基水杨酸是一种适用于 ELISA 分析的过氧化物酶底物。该底物生成棕色的可溶性终产物，该产物可通过分光光度法在 450nm 处读取。加入 3N NaOH 可终止反应，然后在 550nm 处进行读取。
Quantity
Contains 100 mg substrate per tablet.

Sigma Aldrich - A3021

Application
5-氨基水杨酸是一种适用于 ELISA 分析的过氧化物酶底物。该底物生成棕色的可溶性终产物，该产物可通过分光光度法在 450nm 处读取。加入 3N NaOH 可终止反应，然后在 550nm 处进行读取。

Sigma Aldrich - A3537

Application
5-氨基水杨酸是一种适用于 ELISA 分析的过氧化物酶底物。该底物生成棕色的可溶性终产物，该产物可通过分光光度法在 450nm 处读取。加入 3N NaOH 可终止反应，然后在 550nm 处进行读取。

Sigma Aldrich - A79809

Application
5-Aminosalicylic acid is a peroxidase substrate suitable for use in ELISA procedures. This substrate produces a soluble end product that is brown in color and can be read spectrophotometrically at 450 nm. The reaction may be stopped with 3 N NaOH and read at 550 nm.
Packaging
100 g in poly bottle
5 g in glass bottle

Sigma Aldrich - 09410

Application
5-Aminosalicylic acid is a peroxidase substrate suitable for use in ELISA procedures. This substrate produces a soluble end product that is brown in color and can be read spectrophotometrically at 450 nm. The reaction may be stopped with 3 N NaOH and read at 550 nm.

Sigma Aldrich - 73530

Application
5-Aminosalicylic acid is a peroxidase substrate suitable for use in ELISA procedures. This substrate produces a soluble end product that is brown in color and can be read spectrophotometrically at 450 nm. The reaction may be stopped with 3 N NaOH and read at 550 nm.

Sigma Aldrich - 09409

Application
5-Aminosalicylic acid is a peroxidase substrate suitable for use in ELISA procedures. This substrate produces a soluble end product that is brown in color and can be read spectrophotometrically at 450 nm. The reaction may be stopped with 3 N NaOH and read at 550 nm.

Sigma Aldrich - 09407

Application
5-Aminosalicylic acid is a peroxidase substrate suitable for use in ELISA procedures. This substrate produces a soluble end product that is brown in color and can be read spectrophotometrically at 450 nm. The reaction may be stopped with 3 N NaOH and read at 550 nm.
Other Notes
Peroxidase substrate suitable for use in ELISA procedures1

Toronto Research Chemicals - M258100

The active metabolite of Sulfasalazine (S699084). Anti-inflammatory (gastrointestinal).

REFERENCES

• Link
• http://en.wikipedia.org/wiki/Mesalazine
• Friedman, G., et al.: Am. J. Gastroenterol., 81, 141 (1986)
• Tursi A., Expert Opin. Pharmacother., 6, 69 (2005)
• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 219B, (ir)
• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 2, 1121C, (nmr)
• CRC Atlas of Spectral Data and Physical Constants, b848, (ir, uv)
• Weil, H. et al., Ber., 1922, 55, 2664, (synth)
• Drain, D.J. et al., J.C.S., 1949, 1498-1503, (N-Ac)
• Shavel, J. et al., J. Am. Pharm. Assoc., 1953, 42, 402; CA, 48, 9325
• Lepri, L. et al., J. Chromatogr., 1974, 88, 331
• Georgieva, M., Anal. Chim. Acta, 1978, 101, 139
• Hoult, J.R.S., Drugs, 1986, 32, 18, (rev)
• Myers, B. et al., Gut, 1987, 28, 196, (metab)
• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 8427
• Dobson, A.J. et al., Acta Cryst. C, 1998, 54, 1632-1634, (cryst struct)
• Dash, A.K. et al., Anal. Profiles Drug Subst., 1998, 25, 209-242, (rev, pharmacol)
• Prakash, A. et al., Drugs, 1999, 57, 383-408, (rev)
• Clemett, D. et al., Drugs, 2000, 59, 929-956
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, AMM500