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89-57-6 molecular structure
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5-amino-2-hydroxybenzoic acid

ChemBase ID: 129
Molecular Formular: C7H7NO3
Molecular Mass: 153.13538
Monoisotopic Mass: 153.04259309
SMILES and InChIs

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

Cite this record

CBID:129 http://www.chembase.cn/molecule-129.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
5-amino-2-hydroxybenzoic acid
IUPAC Traditional name
mesalazine
5-amino-2-hydroxybenzoic acid
Brand Name
Asacol
Asacolitin
Canasa
Claversal
Fisalamine
Lixacol
Mesasal
Pentasa
Rowasa
Salofalk
Synonyms
5-aminosalicylate
5-aminosalicylic acid
5-ASA
Mesalamine
5-Amino-2-hydroxybenzoic acid
5-aminosalicylic acid
Mesalazine
Asacol
P
Mesalamine
5-Amino-2-hydroxybenzoic acid 97%
5-Amino-2-hydroxybenzoic acid
5-AS
5-Aminosalicylic acid
5-AMINOSALICYLIC ACID
Mesalamine
Fisalamine
Asacolitin
Claversal
Mesalazine
Asalit
Rowasa
Salofalk
Mesalazine
Mesasal
Pentasa
5-氨基-2-羟基苯甲酸
氨水杨酸
5-氨基水杨酸
氨水杨酸
5-氨基水杨酸
CAS Number
89-57-6
EC Number
201-919-1
MDL Number
MFCD00007877
Beilstein Number
2090421
Merck Index
145904
PubChem SID
24891301
24846332
160963592
46509142
24891065
24846331
24890780
PubChem CID
4075

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 2.0241883  H Acceptors
H Donor LogD (pH = 5.5) -0.43266416 
LogD (pH = 7.4) -1.7183259  Log P -0.2897824 
Molar Refractivity 39.9955 cm3 Polarizability 14.463507 Å3
Polar Surface Area 83.55 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 0.75  LOG S -1.1 
Solubility (Water) 1.22e+01 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
0.84 g/L at 20°C expand Show data source
DMSO expand Show data source
Apperance
dark gray to brown powder expand Show data source
off-white to gray powder expand Show data source
Off-White to Pale Beige Solid expand Show data source
tablet expand Show data source
tablets expand Show data source
Melting Point
>250°C (dec) expand Show data source
275-280 °C (dec.)(lit.) expand Show data source
280(dec.) expand Show data source
280(dec.)°C expand Show data source
ca 280°C dec. expand Show data source
Hydrophobicity(logP)
1.2 expand Show data source
pH
4.5-5.5 (25 °C, 1 tablet in 100 ml H2O) expand Show data source
Storage Condition
-20°C expand Show data source
-20°C Freezer expand Show data source
2-8°C expand Show data source
Storage Warning
IRRITANT expand Show data source
Irritant expand Show data source
RTECS
VO1400000 expand Show data source
European Hazard Symbols
Irritant Irritant (Xi) 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
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
36/37/38 expand Show data source
Safety Statements
26-36 expand Show data source
26-37 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
H315-H319-H335-H303 expand Show data source
GHS Precautionary statements
P261-P305 + P351 + P338 expand Show data source
P261-P305+P351+P338-P302+P352-P321-P405-P501A expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves expand Show data source
Storage Temperature
2-8°C expand Show data source
Mechanism of Action
Cyclooxygenase inhibitor expand Show data source
Prostaglandin antagonist expand Show data source
Purity
≥95% (NT) expand Show data source
≥97.0% (NT) expand Show data source
≥99% expand Show data source
95% expand Show data source
97% expand Show data source
99% expand Show data source
Concentration
~100 mg/tablet (enzym.) expand Show data source
Grade
purum expand Show data source
technical expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
Download expand Show data source
Application(s)
Antiinflammatory agent expand Show data source
Antiseptic expand Show data source
Drug used for treatment of ulcerative colitis expand Show data source
Esters used as sunscreens expand Show data source
Low acute oral toxicity expand Show data source
Pharmacopeia Traceability
traceable to PhEur Y0000297 expand Show data source
traceable to USP 1392705 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 Selleck Chemicals Selleck Chemicals
DrugBank - DB00244 external link
Item Information
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
MP Biomedicals - 05215090 external link
MP Biomedicals Rare Chemical collection
MP Biomedicals - 02154770 external link
(5-Amino-2-hydroxybenzoic acid) Purity: 99% Off-white to gray powder.
Sigma Aldrich - A3021 external link
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 external link
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 - 09410 external link
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 external link
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 - A6178 external link
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 - 09407 external link
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
Sigma Aldrich - A79809 external link
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 - 73530 external link
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.
Toronto Research Chemicals - M258100 external link
The active metabolite of Sulfasalazine (S699084). Anti-inflammatory (gastrointestinal).
Selleck Chemicals - S1681 external link
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]

REFERENCES

REFERENCES

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