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  • Product Name: Mesalamine
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89-57-6

89-57-6 structure
89-57-6 structure

Name mesalamine
Synonyms 5-Aminosalicylic Acid
Mesalamine
5-AMINOSALICILIC ACID
5-AMINO SALICYLIC ACID
Mesalamine (Lialda)
Bactylan
Pasalon-rakeet
5-amino-2-hydroxybenzoic acid
Tubersan
Salvis
Paracipan
EINECS 201-919-1
4-Amino-2-hydroxybenzoic acid
MFCD00007877
Sanipirol
Lepasen
PASA
2-Cyanobenzoic acid
Pasmicina
Benzoic acid, 4-amino-2-hydroxy-
Rezipas
ZR CQ DVQ
Passodico
5-AMINO-2-HYDROXYBENZOIC ACID FOR SYNTHESIS
5-Aminosalicylicacid
5-AMINOSALICYLIC ACID (MESALAZINE)
5-Aminosalicglic acid
Mesalazine
Aminosalicylic Acid
5-AMINOSALICYLIC ACID , CRM STANDARD
Aminacyl
Paser
Description 5-Aminosalicylic acid acts as a specific PPARγ agonist and also inhibits p21-activated kinase 1 (PAK1) and NF-κB.
Related Catalog
Target

PPARγ

PAK1

p65

In Vitro 5-Aminosalicylic acid (5-ASA) is a specific agonist for PPARγ, and only PPARγ but not PPARα or PPARδ induces p65 degradation. 5-Aminosalicylic acid induces degradation of p65 protein indicative of PPARγ's E3 ubiquitin ligase activity. 5-Aminosalicylic acid also inhibits PAK1 at the mRNA level which is suggestive of an additional mechanism independent of PPARγ ligand activation. 5-Aminosalicylic acid blocks NF-κB in intestinal epithelial cells (IECs) through inhibition of PAK1[1]. Pretreatment with 5-Aminosalicylic acid (5-ASA) or Nimesulide at different concentration (10-1000 μmol/L) for 12-96 h, inhibits the growth of HT-29 colon carcinoma cells in a dose and time-dependent manner. However, the suppression of 5-Aminosalicylic acid or Nimesulide has no statistical significance. The growth of HT-29 colon carcinoma cells is inhibited dose-dependently when pretreated with different doses of combined 5-Aminosalicylic acid and Nimesulide. Combined 5-Aminosalicylic acid (final concentration 100 μM) and Nimesulide (final concentration 10-1000 μM) inhibits the proliferation of HT-29 colon carcinoma cells in a dose-dependent manner, being more potent than corresponding dose of Nimesulide. Similarly, combined Nimesulide (final concentration 100 μM) and 5-Aminosalicylic acid (final concentration 10-1000 μM) also inhibits the proliferation of these cells dose-dependently, being more potent than corresponding dose of 5-Aminosalicylic acid[2].
In Vivo 5-Aminosalicylic acid (5-ASA) has an antineoplastic effect in a xenograft tumor model. To evaluate the in vivo antineoplasic effect of 5-Aminosalicylic acid, SCID mice engrafted with HT-29 colon cancer cells are treated daily for 21 consecutive days with 5-Aminosalicylic acid at 50 mM. At the end of the treatment, a reduction of 80-86% of tumor weight and volume is observed in SCID mice receiving 5-Aminosalicylic acid compared with control mice or mice treated with GW9662 alone. The antineoplastic effect of 5-Aminosalicylic acid is already detectable after 10 days of 5-Aminosalicylic acid treatment. Similar results are obtained with mice treated with 5-Aminosalicylic acid at 5 mM. Antitumorigenic effect of 5-Aminosalicylic acid is completely abolished at 21 days by simultaneous intraperitoneal administration of GW9662. Thus, the observed antineoplastic effect of 5-Aminosalicylic acid is at least partially dependent on PPARγ[3].
Cell Assay Cytostatic effects are measured by MTT assay. HT-29 colon carcinoma cells are detached with a 0.25% trypsin solution for 5 min. Subsequently, the cells are seeded onto 96-well plates (1×106 cells/well), supplemented with 10% FCS and allowed to attach for 24 h before the addition of test compounds (5-Aminosalicylic acid 10, 50, 100, 500, and 1000 μM; Nimesulide; and their combination). Test compounds are diluted in serum-free culture medium. Then the cells are incubated in a medium or at different concentrations of drugs for 48 h, 20 μL of MTT solution (5 g/L) in PBS is added. Four hours later, the medium in each well is removed, and 120 μL of 0.04 mM muriatic isopropanol is added, slightly concussed for 10 min. Dye uptake is measured at 490 nm with an ELISA reader. Five wells are used for each concentration or as a control group. On the other hand, the cells are seeded onto 96-well plates (1×106 cells/well) and allowed to attach for 24 h, then treated with test compounds (5-Aminosalicylic acid, Nimesulide, and their combination). The final concentration is 100 μM. The same medium is added into the control group and dye uptake is then measured. Five wells are used for each test compound or control group[2].
Animal Admin Mice[3] Six to seven weeks old pathogen-free BALB/c SCID mice are used. Human colon cancer cells (107 HT-29 cells) pretreated or not with GW9662 for 24 h are implanted subcutaneously in the flank of animals. Two days after cell inoculation, mice are treated with 5-Aminosalicylic acid (5 or 50 mM) administered daily by peritumoral injection for 10 or 21 days. The effect of PPARγ during 5-Aminosalicylic acid treatment is evaluated by daily intraperitoneal injection of GW9662 (1 mg/kg/day). The control group receives saline instead of 5-Aminosalicylic acid. Mice are checked three times a week for tumor development. After killing at 10 or 21 days, tumor size and volume are calculated. Tumors are weighted before paraffin embedding for histological examination.
References

[1]. Dammann K, et al. PAK1 modulates a PPARγ/NF-κB cascade in intestinal inflammation. Biochim Biophys Acta. 2015 Oct;1853(10 Pt A):2349-60.

[2]. Fang HM, et al. 5-aminosalicylic acid in combination with Nimesulide inhibits proliferation of colon carcinoma cells in vitro. World J Gastroenterol. 2007 May 28;13(20):2872-7.

[3]. Rousseaux C, et al. The 5-aminosalicylic acid antineoplastic effect in the intestine is mediated by PPARγ. Carcinogenesis. 2013 Nov;34(11):2580-6.

Density 1.5±0.1 g/cm3
Boiling Point 380.8±32.0 °C at 760 mmHg
Melting Point 275-280 °C (dec.)(lit.)
Molecular Formula C7H7NO3
Molecular Weight 153.135
Flash Point 184.1±25.1 °C
Exact Mass 153.042587
PSA 83.55000
LogP 1.14
Vapour Pressure 0.0±0.9 mmHg at 25°C
Index of Refraction 1.691
Water Solubility <0.1 g/100 mL at 21 ºC

CHEMICAL IDENTIFICATION

RTECS NUMBER :
VO1400000
CHEMICAL NAME :
Salicylic acid, 5-amino-
CAS REGISTRY NUMBER :
89-57-6
BEILSTEIN REFERENCE NO. :
2090421
LAST UPDATED :
199710
DATA ITEMS CITED :
14
MOLECULAR FORMULA :
C7-H7-N-O3
MOLECULAR WEIGHT :
153.15
WISWESSER LINE NOTATION :
ZR DQ CVQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
6857 mg/kg/17W-I
TOXIC EFFECTS :
Gastrointestinal - nausea or vomiting Liver - jaundice, cholestatic
REFERENCE :
JOHEEC Journal of Hepathology. (Elsevier Science, 655 Avenue of the Americas, New York, NY 10010) V.1- 1985- Volume(issue)/page/year: 26,425,1997
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
21800 mg/kg/39W-I
TOXIC EFFECTS :
Lungs, Thorax, or Respiration - fibrosis, focal (pneumoconiosis) Lungs, Thorax, or Respiration - respiratory depression Blood - eosinophilia
REFERENCE :
AJGAAR American Journal of Gastroenterology. (American College of Gastroenterology, Inc., 428 E. Preston St., Baltimore, MD 21202) V.21- 1954- Volume(issue)/page/year: 91,1039,1996
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
51 mg/kg/5D-I
TOXIC EFFECTS :
Gastrointestinal - hypermotility, diarrhea Skin and Appendages - dermatitis, other (after systemic exposure) Nutritional and Gross Metabolic - body temperature increase
REFERENCE :
LANCAO Lancet. (7 Adam St., London WC2N 6AD, UK) V.1- 1823- Volume(issue)/page/year: 1,917,1984
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
8 mg/kg
TOXIC EFFECTS :
Behavioral - headache Gastrointestinal - hypermotility, diarrhea Nutritional and Gross Metabolic - body temperature increase
REFERENCE :
LANCAO Lancet. (7 Adam St., London WC2N 6AD, UK) V.1- 1823- Volume(issue)/page/year: 1,917,1984
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
2057 mg/kg/17W-I
TOXIC EFFECTS :
Blood - agranulocytosis Nutritional and Gross Metabolic - body temperature increase
REFERENCE :
LANCAO Lancet. (7 Adam St., London WC2N 6AD, UK) V.1- 1823- Volume(issue)/page/year: 341,1476,1993
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
2800 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Behavioral - food intake (animal) Gastrointestinal - other changes
REFERENCE :
NTIS** National Technical Information Service. (Springfield, VA 22161) Formerly U.S. Clearinghouse for Scientific & Technical Information. Volume(issue)/page/year: OTS0570511
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
1 gm/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold Kidney, Ureter, Bladder - other changes in urine composition Skin and Appendages - hair
REFERENCE :
OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 47,505,1994
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
5 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
ZENBAX Zeitschrift fuer Naturforschung, Teil B: Anorganische Chemie, Organische Chemie, Biochemie, Biophysik, Biologie. (Tuebingen, Fed. Rep. Ger.) V.2B-27B, 1947-1972. For publisher information, see ZNCBDA. Volume(issue)/page/year: 6B,183,1951
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
681 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
PHTOEH Pharmacology and Toxicology (Copenhagen). (Munksgaard International Pub., POB 2148, DK-1016 Copenhagen K, Denmark) V.60- 1987- Volume(issue)/page/year: 64,247,1989
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Primate - monkey
DOSE/DURATION :
3 gm/kg
TOXIC EFFECTS :
Sense Organs and Special Senses (Eye) - ptosis Behavioral - somnolence (general depressed activity) Kidney, Ureter, Bladder - hematuria
REFERENCE :
OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 47,509,1994
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Administration onto the skin
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
>5 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NTIS** National Technical Information Service. (Springfield, VA 22161) Formerly U.S. Clearinghouse for Scientific & Technical Information. Volume(issue)/page/year: OTS0570511 ** OTHER MULTIPLE DOSE TOXICITY DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
36400 mg/kg/13W-I
TOXIC EFFECTS :
Kidney, Ureter, Bladder - urine volume increased Kidney, Ureter, Bladder - changes in bladder weight Blood - normocytic anemia
REFERENCE :
OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 48,277,1994
Symbol GHS07
GHS07
Signal Word Warning
Hazard Statements H315-H319-H335
Precautionary Statements P261-P305 + P351 + P338
Personal Protective Equipment dust mask type N95 (US);Eyeshields;Gloves
Hazard Codes Xi
Risk Phrases 36/37/38
Safety Phrases S26-S36-S24/25
RIDADR NONH for all modes of transport
WGK Germany 2
RTECS VO1400000
HS Code 29225000
HS Code 2922509090
Summary 2922509090. other amino-alcohol-phenols, amino-acid-phenols and other amino-compounds with oxygen function. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%