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'''Balsalazide''' is an anti-inflammatory drug used in the treatment of [[inflammatory bowel disease]]. It is sold under the brand names '''Giazo''', '''Colazal''' in the US and '''Colazide''' in the UK. It is also sold in generic form in the US by several generic manufacturers. |
'''Balsalazide''' is an anti-inflammatory drug used in the treatment of [[inflammatory bowel disease]]. It is sold under the brand names '''Giazo''', '''Colazal''' in the US and '''Colazide''' in the UK. It is also sold in generic form in the US by several generic manufacturers. |
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It is usually administered as the disodium salt. Balsalazide releases [[mesalazine]], also known as 5-aminosalicylic acid, or 5-ASA,<ref>{{Cite journal | pmid = 11709512 | year = 2001 | last1 = Kruis | first1 = W. | last2 = Schreiber | last3 = Theuer | first3 = D. | last4 = Brandes | first4 = J. W. | last5 = Schütz | first5 = E. | last6 = Howaldt | first6 = S. | last7 = Krakamp | first7 = B. | last8 = Hämling | first8 = J. | last9 = Mönnikes | first9 = H. | last10 = Koop | first10 = I. | last11 = Stolte | first11 = M. | last12 = Pallant | first12 = D. | last13 = Ewald | first13 = U. | title = Low dose balsalazide (1.5 |
It is usually administered as the disodium salt. Balsalazide releases [[mesalazine]], also known as 5-aminosalicylic acid, or 5-ASA,<ref>{{Cite journal | pmid = 11709512 | year = 2001 | last1 = Kruis | first1 = W. | last2 = Schreiber | last3 = Theuer | first3 = D. | last4 = Brandes | first4 = J. W. | last5 = Schütz | first5 = E. | last6 = Howaldt | first6 = S. | last7 = Krakamp | first7 = B. | last8 = Hämling | first8 = J. | last9 = Mönnikes | first9 = H. | last10 = Koop | first10 = I. | last11 = Stolte | first11 = M. | last12 = Pallant | first12 = D. | last13 = Ewald | first13 = U. | title = Low dose balsalazide (1.5 g twice daily) and mesalazine (0.5 g three times daily) maintained remission of ulcerative colitis but high dose balsalazide (3.0 g twice daily) was superior in preventing relapses | volume = 49 | issue = 6 | pages = 783–789 | journal = Gut | doi = 10.1136/gut.49.6.783| pmc = 1728533 | first2 = I.}}</ref> in the large intestine. Its advantage over that drug in the treatment of [[ulcerative colitis]] is believed to be the delivery of the active agent past the small intestine to the large intestine, the active site of ulcerative colitis. |
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==Synthesis== |
==Synthesis== |
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[[File:Balsalazide synthesis.png|thumb|center|600px|Balsalazide synthesis: Biorex Laboratories, {{Cite patent|GB|2080796}} (1986).]] |
[[File:Balsalazide synthesis.png|thumb|center|600px|Balsalazide synthesis: Biorex Laboratories, {{Cite patent|GB|2080796}} (1986).]] |
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#That product is then treated with [[nitrous acid]] to give the [[diazonium salt]]. |
#That product is then treated with [[nitrous acid]] to give the [[diazonium salt]]. |
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#Reaction of this species with [[salicylic acid]] proceeds at the position para to the phenol to give balsalazide. |
#Reaction of this species with [[salicylic acid]] proceeds at the position para to the phenol to give balsalazide. |
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==References== |
==References== |
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{{reflist}} |
{{reflist}} |
Revision as of 04:02, 17 August 2015
Clinical data | |
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Trade names | Colazal, Giazo |
AHFS/Drugs.com | Monograph |
MedlinePlus | a699052 |
ATC code | |
Legal status | |
Legal status |
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Pharmacokinetic data | |
Bioavailability | <1% |
Protein binding | ≥99% |
Elimination half-life | 12hr |
Identifiers | |
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CAS Number | |
PubChem CID | |
DrugBank | |
ChemSpider | |
UNII | |
ChEBI | |
ChEMBL | |
CompTox Dashboard (EPA) | |
ECHA InfoCard | 100.117.186 |
Chemical and physical data | |
Formula | C17H15N3O6 |
Molar mass | 357.318 g/mol g·mol−1 |
3D model (JSmol) | |
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(what is this?) (verify) |
Balsalazide is an anti-inflammatory drug used in the treatment of inflammatory bowel disease. It is sold under the brand names Giazo, Colazal in the US and Colazide in the UK. It is also sold in generic form in the US by several generic manufacturers.
It is usually administered as the disodium salt. Balsalazide releases mesalazine, also known as 5-aminosalicylic acid, or 5-ASA,[1] in the large intestine. Its advantage over that drug in the treatment of ulcerative colitis is believed to be the delivery of the active agent past the small intestine to the large intestine, the active site of ulcerative colitis.
Synthesis
- Starting material is 4-aminohippuric acid, obtained by coupling para-aminobenzoic acid and glycine.
- That product is then treated with nitrous acid to give the diazonium salt.
- Reaction of this species with salicylic acid proceeds at the position para to the phenol to give balsalazide.
References
- ^ Kruis, W.; Schreiber, I.; Theuer, D.; Brandes, J. W.; Schütz, E.; Howaldt, S.; Krakamp, B.; Hämling, J.; Mönnikes, H.; Koop, I.; Stolte, M.; Pallant, D.; Ewald, U. (2001). "Low dose balsalazide (1.5 g twice daily) and mesalazine (0.5 g three times daily) maintained remission of ulcerative colitis but high dose balsalazide (3.0 g twice daily) was superior in preventing relapses". Gut. 49 (6): 783–789. doi:10.1136/gut.49.6.783. PMC 1728533. PMID 11709512.