CAS 89-57-6|mesalazine|5-Amino-2-hydroxybenzoic acid|5-amino-2-hydroxybenzoic acid|5-aminosalicylic acid|5-Amino-2-hydroxybenzoic acid 97%|5-氨基水杨酸|5-AS|5-氨基-2-羟基苯甲酸|5-Aminosalicylic acid|...

General Information

Structure

Molecular Formula

C₇H₇NO₃

Molecular Mass

153.13538

Exact Mass

153.04259309

Charge

0

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

Canonic Smiles

Nc1ccc(c(c1)C(=O)O)O

Isomeric Smiles

Oc1c(cc(N)cc1)C(=O)O

Calculated Properties

JChem

LogD (pH = 7.4)

-1.72

LogD (pH = 5.5)

-0.43

Log P

-0.29

Rotatable Bonds

1

H Donor

3

H Acceptors

4

Lipinski's Rule of Five

true

Acid pKa

2.02

Polar Surface Area

83.55

Polarizability

14.26

Molar Refractivity

40.00

LOG S

-0.92

Data Source

Academic Data

Data Source

Names and Identifiers

IUPAC Traditional name

mesalazine 5-amino-2-hydroxybenzoic acid

Synonyms

5-Amino-2-hydroxybenzoic acid5-aminosalicylic acid5-Amino-2-hydroxybenzoic acid 97%5-氨基水杨酸5-AS5-氨基-2-羟基苯甲酸5-Aminosalicylic acid氨水杨酸5-AMINOSALICYLIC ACIDMesalamine5-Amino-2-hydroxybenzoic acidAsacolP 5-aminosalicylic acidMesalazineMesalamineRowasaMesasalMesalazineMesalazineFisalamineAsacolitinClaversalAsalitSalofalk5-ASAPentasa5-aminosalicylate5-氨基水杨酸Mesalamine氨水杨酸Mesalazinemesalaminem-Aminosalicylic acid5-ASA5-Aminosalicylic acid3-carboxy-4-hydroxyanilinep-Aminosalicylsaeure

IUPAC name

5-amino-2-hydroxybenzoic acid

Brand Name

CanasaMesasalPentasaAsacolAsacolitinLixacolClaversalSalofalkRowasaFisalamineIialda

API Name

Mesalazine

International Nonproprietary Name (INN)

mesalazinemesalazinamesalazinum

Names and Identifiers

Registration numbers

PubChem SID

46509142160963592248907802489130124891065248463312484633249658687

PubChem CID

CAS Number

MDL Number

EC Number

Beilstein Number

Merck Index

DrugBank ID

SureChEMBL Database

SCHEMBL31297SCHEMBL18038934

PubMed Citation Links

22648999231466642230473510648473281662172313783823302220

BRENDA Database

1.11.1.71.14.14.182.3.1.51.13.11.861.1.1.1531.11.2.21.14.13.11.13.11.43.5.3.153.1.3.162.7.11.102.1.1.671.14.14.94

CompTox Database

DTXSID5024506

Drug Central Database

1,710

CHEBI ID

CHEBI:6775

MetaboLights Database

MTBLS2096MTBLS2406MTBLS4463MTBLS4012MTBLS1411

BKMS React Database

36968109764

BRENDA Ligand Database

ACToR Database

CHEMBL

NMRShiftDB Database

Reaxys Registry

BindingDB Database

MetaCyc Database

HMDB Database

LINCS Database

Wikipedia Title

KEGG DRUG Database

Registration numbers

Properties

Pharmacology Properties

Mechanism of Action

Cyclooxygenase inhibitor

Prostaglandin antagonist

Properties

Related Proteins

No Data Available

Click here to submit data

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

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]

MP Biomedicals

02154770

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

05215090

MP Biomedicals Rare Chemical collection

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。

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。

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.

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

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

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.

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.

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.

TRC

M258100

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

ChEBI

CHEBI:6775

A monohydroxybenzoic acid that is salicylic acid substituted by an amino group at the 5-position.

Molecule Details

References

PubChem Literature

From Data Sources

• 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)

• Georgieva, M., Anal. Chim. Acta, 1978, 101, 139

• 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)

• Myers, B. et al., Gut, 1987, 28, 196, (metab)

• Dobson, A.J. et al., Acta Cryst. C, 1998, 54, 1632-1634, (cryst struct)

• Lepri, L. et al., J. Chromatogr., 1974, 88, 331

• Dash, A.K. et al., Anal. Profiles Drug Subst., 1998, 25, 209-242, (rev, pharmacol)

• Drain, D.J. et al., J.C.S., 1949, 1498-1503, (N-Ac)

• Hoult, J.R.S., Drugs, 1986, 32, 18, (rev)

• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 8427

• Prakash, A. et al., Drugs, 1999, 57, 383-408, (rev)

• Clemett, D. et al., Drugs, 2000, 59, 929-956

• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 219B, (ir)

• Shavel, J. et al., J. Am. Pharm. Assoc., 1953, 42, 402; CA, 48, 9325

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, AMM500

References

Bioactivity

PubChem BioAssay

Bioactivity

Molecule

ID:129