5-Aminosalicylic Acid

Modify Date: 2024-01-01 21:07:45

5-Aminosalicylic Acid structure	Common Name	5-Aminosalicylic Acid
	CAS Number	89-57-6	Molecular Weight	153.135
	Density	1.5±0.1 g/cm3	Boiling Point	380.8±32.0 °C at 760 mmHg
	Molecular Formula	C₇H₇NO₃	Melting Point	275-280 °C (dec.)(lit.)
	MSDS	Chinese USA	Flash Point	184.1±25.1 °C
	Symbol	GHS07	Signal Word	Warning

Use of 5-Aminosalicylic Acid

5-Aminosalicylic acid acts as a specific PPARγ agonist and also inhibits p21-activated kinase 1 (PAK1) and NF-κB.

Name	mesalamine
Synonym	More Synonyms

Description	5-Aminosalicylic acid acts as a specific PPARγ agonist and also inhibits p21-activated kinase 1 (PAK1) and NF-κB.
Related Catalog	Signaling Pathways >> Cell Cycle/DNA Damage >> PAK Signaling Pathways >> Cytoskeleton >> PAK Research Areas >> Inflammation/Immunology
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

5-Aminosalicylic Acid MSDS(Chinese)

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
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

Precursor 8
CAS#:124-38-9 Carbon dioxide CAS#:103-90-2 4-Acetamidophenol CAS#:96-97-9 Salicylic acid,... CAS#:123-30-8 4-Aminophenol
CAS#:121-92-6 3-Nitrobenzoic acid CAS#:3147-53-3 2-hydroxy-5-phe... CAS#:298-14-6 Potassium hydro... CAS#:51-78-5 \|p\|-Aminophenol...
DownStream 9
CAS#:42753-75-3 Methyl 5-amino-... CAS#:345-16-4 5-Fluoro-2-hydr... CAS#:490-79-9 Gentisic acid CAS#:3943-91-7 Ethyl 2,5-dihyd...
CAS#:51-59-2 N-Acetyl Mesalazine CAS#:123-31-9 Hydroquinone CAS#:24619-05-4 5,5'-dithiodisa... CAS#:96-97-9 Salicylic acid,...
CAS#:123-30-8 4-Aminophenol

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%

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