80.42.29.84 (talk) synthesis schematic + patents. |
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Dimer of [[mesalamine]], [[q.v.]], originally used as a [[mordant]] dye. |
Dimer of [[mesalamine]], [[q.v.]], originally used as a [[mordant]] dye. |
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[[File:Olsalazine synthesis.svg|thumb|center|500px|Olsalazine synthesis:<ref>{{Cite patent|DE|278613}}; C. Mettler, {{US patent|1157169}} (1914, 1915 both to J. R. Geigy).</ref> Improved prepn:<ref>K. H. Agback, A. S. Nygren, {{Cite patent|EP|36636}}; eidem, {{US patent|4528367}} (1981, 1985 both to Pharmacia AB).</ref>]] |
[[File:Olsalazine synthesis.svg|thumb|center|500px|Olsalazine synthesis:<ref>{{Cite patent|DE|278613}}; C. Mettler, {{US patent|1157169}} (1914, 1915 both to J. R. Geigy).</ref> Improved prepn:<ref>K. H. Agback, A. S. Nygren, {{Cite patent|EP|36636}}; eidem, {{US patent|4528367}} (1981, 1985 both to Pharmacia AB).</ref>]] |
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[[5-aminosalicylic acid]] ('''1''') is treated with [[nitrous acid]] leading to the [[diazonium salt]] ('''2'''). Reaction of that with [[methyl salicylate]] gives the diazonium coupling product '''3'''. [[Saponification]] then yields olsalzaline ('''4'''). |
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==References== |
==References== |
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{{Reflist|2}} |
{{Reflist|2}} |
Revision as of 10:42, 6 September 2015
Clinical data | |
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Trade names | Dipentum |
AHFS/Drugs.com | Monograph |
MedlinePlus | a601088 |
ATC code | |
Legal status | |
Legal status |
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Pharmacokinetic data | |
Protein binding | 99% |
Elimination half-life | 0.9 hours |
Identifiers | |
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CAS Number | |
PubChem CID | |
DrugBank | |
ChemSpider | |
UNII | |
KEGG | |
ChEMBL | |
CompTox Dashboard (EPA) | |
ECHA InfoCard | 100.116.494 |
Chemical and physical data | |
Formula | C14H10N2O6 |
Molar mass | 302.239g/mol g·mol−1 |
3D model (JSmol) | |
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(what is this?) (verify) |
Olsalazine is an anti-inflammatory drug used in the treatment of inflammatory bowel disease such as ulcerative colitis. It is sold under the name Dipentum.
The chemical name is 3,3' -azobis (6-hydroxybenzoate)salicylic acid. It is sold as the disodium salt.
Like balsalazide, olsalazine is believed to deliver mesalazine, or 5-aminosalicylic acid (5-ASA), past the small intestine, directly to the large intestine, which is the active site of disease in ulcerative colitis.
History
Olsalazine gained Food and Drug Administration (FDA) approval in 1990.
Supply
The drug is supplied by UCB Pharma.
Other indications
The Australian biotech company Giaconda has developed a combination therapy for treating constipation-predominant irritable bowel syndrome that uses olsalazine and the anti-gout drug colchicine.
Synthesis
Dimer of mesalamine, q.v., originally used as a mordant dye.
5-aminosalicylic acid (1) is treated with nitrous acid leading to the diazonium salt (2). Reaction of that with methyl salicylate gives the diazonium coupling product 3. Saponification then yields olsalzaline (4).
References
- ^ DE 278613; C. Mettler, U.S. patent 1,157,169 (1914, 1915 both to J. R. Geigy).
- ^ K. H. Agback, A. S. Nygren, EP 36636; eidem, U.S. patent 4,528,367 (1981, 1985 both to Pharmacia AB).
External links