Balsalazide
- Product Name
- Balsalazide
- CAS No.
- 80573-04-2
- Chemical Name
- Balsalazide
- Synonyms
- Giazo;CS-1360;balsalazido;BALSALAZIDE;Balsalazine;Balsalazidum;COLAZAL;GIAZO;Balsalazide D4;Balsalazide 98%;BALSALAZIDE SODIUM
- CBNumber
- CB9148828
- Molecular Formula
- C17H15N3O6
- Formula Weight
- 357.32
- MOL File
- 80573-04-2.mol
Balsalazide Property
- Melting point:
- 254-255?C
- Boiling point:
- 729.6±60.0 °C(Predicted)
- Density
- 1.44±0.1 g/cm3(Predicted)
- vapor pressure
- 0Pa at 20℃
- storage temp.
- -20°C Freezer
- solubility
- DMSO (Slightly), Methanol (Slightly)
- form
- Solid
- pka
- 2.97±0.10(Predicted)
- color
- Yellow to Beige
- InChI
- InChI=1S/C17H15N3O6/c21-14-6-5-12(9-13(14)17(25)26)20-19-11-3-1-10(2-4-11)16(24)18-8-7-15(22)23/h1-6,9,21H,7-8H2,(H,18,24)(H,22,23)(H,25,26)/b20-19+
- InChIKey
- IPOKCKJONYRRHP-FMQUCBEESA-N
- SMILES
- C(O)(=O)C1=CC(/N=N/C2=CC=C(C(NCCC(O)=O)=O)C=C2)=CC=C1O
- LogP
- 1 at 25℃ and pH7.5
- EPA Substance Registry System
- Benzoic acid, 5-[(1E)-2-[4-[[(2-carboxyethyl)amino]carbonyl]phenyl]diazenyl]-2-hydroxy- (80573-04-2)
N-Bromosuccinimide Price
- Product number
- 18680
- Product name
- Balsalazide
- Purity
- ≥98%
- Packaging
- 5mg
- Price
- $57
- Updated
- 2024/03/01
- Product number
- 18680
- Product name
- Balsalazide
- Purity
- ≥98%
- Packaging
- 10mg
- Price
- $107
- Updated
- 2024/03/01
- Product number
- 18680
- Product name
- Balsalazide
- Purity
- ≥98%
- Packaging
- 25mg
- Price
- $233
- Updated
- 2024/03/01
- Product number
- 28888
- Product name
- Balsalazide-d4
- Packaging
- 1mg
- Price
- $396
- Updated
- 2024/03/01
- Product number
- 18680
- Product name
- Balsalazide
- Purity
- ≥98%
- Packaging
- 50mg
- Price
- $437
- Updated
- 2024/03/01
Balsalazide Chemical Properties,Usage,Production
Description
Colazide was launched in the UK for mild to moderate acute attacks of ulcerative colitis. It can be prepared by diazotization of 3-(4-aminobenzoylamino) propionic acid followed by condensation with salicylic acid. Colazide, an analogue of sulfasalazine, was found to be non-toxic and non-mutagenic in the Ames test. Once ingested the molecule releases a non-toxic fragment, 4-aminobenzoyl-β-alanine (poorly absorbed - 75% excretion in stool), and the active component 5- aminosalicylic acid (Mesalazine). The exact mechanism of action is not clearly understood but it is cytoprotective and has antiinflammatory properties. Other biological effects have been observed and include the following: (a) granulocyte activation is blocked, (b) there is a reduction in myeloperoxidase activity, and (c) a reduction in the release of arachidonic acid with a concomitant decrease in prostaglandin and leucotriene (as indicated by the lack of production of LTB4) production. It can behave as a reactive oxygen species (ROS) scavenger, inhibit PAF formation, reduce IL-1 production, and antagonize TNF and NK cells. While comparable in efficacy to sulfasalazine, Colazide removes the possibility of sulfasalazine side-effects, such as, agranulocytosis, hepatotoxicity and male infertility.
Description
Balsalazide is a prodrug form of 5-aminosalicylic acid (5-ASA; ). It is cleaved by bacterial azoreductases in the intestinal lumen to release 5-ASA. Balsalazide (600 mg/kg per day) decreases IL-2 levels and increases IL-6 levels in the serum and colonic mucosa membrane, as well as decreases micro- and macroscopic colonic damage, in a rat model of colitis induced by 2,4-dinitrochlorobenzene (DNCB). Formulations containing balsalazide have been used in the treatment of ulcerative colitis.
Chemical Properties
Yellow Solid
Originator
Biorex (UK)
Uses
Balsalazide-d4 is an isotopically labelled analog of Balsalazide (B116300), which is an analogue of Sulfasalazine (S699084). A prodrug of 5-aminosalicylic acid where carrier molecule is 4-aminobenzoyl-β-alanine. Anti-inflammatory (gastrointestinal).
Uses
An analogue of Sulfasalazine, A prodrug of 5-Aminosalicylic Acid
Definition
ChEBI: A monohydroxybenzoic acid consisting of 5-aminosalicylic acid (mesalazine) linked to 4-aminobenzoyl-beta-alanine via an azo bond.
Manufacturing Process
125 g finely powdered 4-nitrobenzoyl chloride were added portionwise, while
stirring, to a solution of 70 g β-alanine in 500 ml water containing 65 g
sodium hydroxide and cooled to 5°C. The reaction mixture was stirred for 3
hours and then added to a mixture of ice and hydrochloric acid. The
precipitate obtained was filtered off, washed with water and dried by suction.
After crystallisation of the dried product from hot acetone, there were
obtained 130 g 4-nitrobenzoyl-β-alanine, M.P. 164°-166°C.
A suspension of 15 g finely powdered 4-nitrobenzoyl-β-alanine in 200 ml
ethanol was stirred in an atmosphere of hydrogen in the presence of 1 g of
palladium-charcoal (5%), while cooling gently. When the absorption of
hydrogen had ceased, the reaction mixture was filtered and the filtrate
concentrated to a small volume. Upon adding diethyl ether and cooling 4-
aminobenzoyl-β-alanine was obtained. The yield was 11.5 g, M.P. 156°-158°C.
8.8 g 4-aminobenzoyl-β-alanine were triturated with 12 ml hydrochloric acid
and the paste obtained was dissolved in 100 ml water. The solution was
cooled to -5°C and a solution of 3 g sodium nitrite in 20 ml water, cooled to
0°C, was added dropwise, while stirring. The diazotised solution was left for 1
hour at 0°C and was then added dropwise at -5°C to a solution of 6 g salicylic
acid in 70 ml water containing 3.6 g sodium hydroxide and 7 g sodium
carbonate. The final reaction mixture was adjusted to a pH of about 8, stirred
for 2 to 3 hours and added to a mixture of dilute hydrochloric acid and ice.
The precipitate obtained was filtered off, washed with water and suction dried.
Crystallisation from hot ethanol gave 11.9 g 5-[(2-carboxy-ethylcarbamoyl)-
phenylazo]-2-hydroxy-benzoic acid, M.P. 254°-255°C.
10.7 g of the free acid were dissolved in 300 ml warm ethanol and treated
with a solution of 2.4 g sodium hydroxide in 25 ml ethanol. The precipitate
obtained was filtered off, washed with ethanol and diethyl ether and dried in a
vacuum at 50°C to give 11.5 g of the disodium salt of 5-[(2-carboxyethylcarbamoyl)-
phenylazo]-2-hydroxy-benzoic acid, M.P. >350°C.
brand name
Colazal (Salix).
Therapeutic Function
Antiinflammatory
Clinical Use
Treatment and maintenance of remission, in mild to moderate ulcerative colitis
Metabolism
Very little of an oral dose of balsalazide is absorbed via the upper gastrointestinal tract, and almost the entire dose reaches its site of action in the colon intact. It is broken down by the colonic bacterial flora into 5-aminosalicylic acid (mesalazine), which is active, and 4-aminobenzoylalanine, which is considered to be an inert carrier. Most of a dose is eliminated via the faeces, but about 25% of the released mesalazine is absorbed and acetylated. A small proportion of 4-aminobenzoylalanine is absorbed and acetylated by first-pass metabolism through the liver. The acetylated metabolites are excreted in the urine.
References
[1] TURSI A. Balsalazide in treating colonic diseases.[J]. Expert Opinion on Drug Metabolism & Toxicology, 2009, 5 12: 1555-1563. DOI: 10.1517/17425250903228842
[2] FELIPE MEIRA DE FARIA. Effects of Rhizophora mangle on Experimental Colitis Induced by TNBS in Rats.[J]. Evidence-based Complementary and Alternative Medicine, 2012: 753971. DOI: 10.1155/2012/753971
Balsalazide Preparation Products And Raw materials
Raw materials
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View Lastest Price from Balsalazide manufacturers
- Product
- Balsalazide 80573-04-2
- Price
- US $0.00-0.00/kg
- Min. Order
- 1kg
- Purity
- 99%
- Supply Ability
- 20tons
- Release date
- 2025-02-11
- Product
- Balsalazide 80573-04-2
- Price
- US $15.00-10.00/KG
- Min. Order
- 1KG
- Purity
- 99%+ HPLC
- Supply Ability
- Monthly supply of 1 ton
- Release date
- 2021-07-10
- Product
- Balsalazide 80573-04-2
- Price
- US $15.00-10.00/KG
- Min. Order
- 1KG
- Purity
- 99%+ HPLC
- Supply Ability
- Monthly supply of 1 ton
- Release date
- 2021-07-08