Updating {{drugbox}} (changes to verified fields - updated 'ChEBI_Ref') per Chem/Drugbox validation (report errors or bugs) |
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{{Short description|Pharmaceutical drug}} |
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{{more citations needed|date=January 2021}} |
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{{Drugbox |
{{Drugbox |
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| Verifiedfields = changed |
| Verifiedfields = changed |
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| verifiedrevid = |
| verifiedrevid = 462265233 |
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⚫ | |||
| IUPAC_name = 5-[(2''Z'')-2-(3-carboxy-4-oxocyclohexa-2,5-dien-1-ylidene)hydrazino]-2-hydroxybenzoic acid |
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⚫ | |||
<!--Clinical data--> |
<!--Clinical data--> |
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| tradename = Dipentum |
| tradename = Dipentum |
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| Drugs.com = {{drugs.com|monograph| |
| Drugs.com = {{drugs.com|monograph|olsalazine-sodium}} |
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| MedlinePlus = a601088 |
| MedlinePlus = a601088 |
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| DailyMedID = Olsalazine |
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
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| pregnancy_AU = C |
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| pregnancy_US = C<!-- A / B / C / D / X --> |
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| pregnancy_AU_comment = <ref name="Drugs.com pregnancy">{{cite web | title=Olsalazine (Dipentum) Use During Pregnancy | website=Drugs.com | date=6 September 2019 | url=https://www.drugs.com/pregnancy/olsalazine.html | access-date=9 October 2020}}</ref> |
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⚫ | |||
| pregnancy_US = C |
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| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 --> |
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| pregnancy_US_comment = <ref name="Drugs.com pregnancy" /> |
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⚫ | |||
| legal_AU = S4 |
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| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII --> |
| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII --> |
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| legal_UK = |
| legal_UK = POM |
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| legal_US = Rx-only |
| legal_US = Rx-only |
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| legal_status = |
| legal_status = |
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| routes_of_administration = |
| routes_of_administration = [[Oral administration|By mouth]] |
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| ATC_prefix = A07 |
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⚫ | |||
<!--Pharmacokinetic data--> |
<!--Pharmacokinetic data--> |
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| bioavailability = |
| bioavailability = |
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| protein_bound = 99% |
| protein_bound = 99% |
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| metabolism = |
| metabolism = |
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| elimination_half-life = 0.9 hours |
| elimination_half-life = 0.9 hours |
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| excretion = |
| excretion = |
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<!--Identifiers--> |
<!--Identifiers--> |
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| index2_label = as salt |
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| |
| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number = 15722-48-2 |
| CAS_number = 15722-48-2 |
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| |
| PubChem = 22419 |
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⚫ | |||
| PubChem = 6003770 |
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⚫ | |||
| DrugBank = DB01250 |
| DrugBank = DB01250 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| UNII = ULS5I8J03O |
| UNII = ULS5I8J03O |
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| KEGG_Ref = {{keggcite|changed|kegg}} |
| KEGG_Ref = {{keggcite|changed|kegg}} |
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| KEGG = |
| KEGG = D08295 |
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| KEGG2_Ref = {{keggcite|changed|kegg}} |
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| KEGG2 = D00727 |
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| ChEBI_Ref = |
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| ChEBI = |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL = |
| ChEMBL = 425 |
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| NIAID_ChemDB = |
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| PDB_ligand = |
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| synonyms = |
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<!--Chemical data--> |
<!--Chemical data--> |
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⚫ | |||
| chemical_formula = |
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⚫ | |||
| molecular_weight = 302.239g/mol |
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| smiles = O=C(O)c1cc(ccc1O)/N=N/c2cc(C(O)=O)c(O)cc2 |
| smiles = O=C(O)c1cc(ccc1O)/N=N/c2cc(C(O)=O)c(O)cc2 |
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| InChI = 1/C14H10N2O6/c17-11-3-1-7(5-9(11)13(19)20)15-16-8-2-4-12(18)10(6-8)14(21)22/h1-6,17-18H,(H,19,20)(H,21,22)/b16-15+ |
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| InChIKey = QQBDLJCYGRGAKP-FOCLMDBBBJ |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C14H10N2O6/c17-11-3-1-7(5-9(11)13(19)20)15-16-8-2-4-12(18)10(6-8)14(21)22/h1-6,17-18H,(H,19,20)(H,21,22)/b16-15+ |
| StdInChI = 1S/C14H10N2O6/c17-11-3-1-7(5-9(11)13(19)20)15-16-8-2-4-12(18)10(6-8)14(21)22/h1-6,17-18H,(H,19,20)(H,21,22)/b16-15+ |
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}} |
}} |
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'''Olsalazine''' is an anti-inflammatory medication used in the treatment of [[ulcerative colitis]].<ref name="pmid2131213">{{cite journal | vauthors = | title = Olsalazine--a further choice in ulcerative colitis | journal = Drug and Therapeutics Bulletin | volume = 28 | issue = 15 | pages = 57–8 | date = July 1990 | pmid = 2131213 | doi = 10.1136/dtb.28.15.57 | s2cid = 7178709 }}</ref><ref name="pmid1711964">{{cite journal | vauthors = Wadworth AN, Fitton A | title = Olsalazine. A review of its pharmacodynamic and pharmacokinetic properties, and therapeutic potential in inflammatory bowel disease | journal = Drugs | volume = 41 | issue = 4 | pages = 647–64 | date = April 1991 | pmid = 1711964 | doi = 10.2165/00003495-199141040-00009 | s2cid = 243654426 }}</ref> It is sold under the brand name '''Dipentum'''.<ref name=Med1>{{cite web |title=Olsalazine Sodium 250 mg Capsules - Summary of Product Characteristics (SmPC) - (emc) |url=https://www.medicines.org.uk/emc/product/3708/smpc#gref |website=www.medicines.org.uk |access-date=9 January 2021}}</ref> |
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'''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. |
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Olsalazine itself is a pro-drug of [[mesalazine]] (5-aminosalicyclic acid or 5-ASA) and is not absorbed in the small intestine. Instead it continues through to the colon where it is cleaved into two molecules of 5-ASA by [[azoreductases]] produced by colonic bacteria. Olsalazine thus exerts its anti-inflammatory effect by its colonic breakdown into 5-ASA which inhibits cyclooxygenase and lipoxygenase thereby reducing prostaglandin and leukotriene production.<ref name=Med1/> |
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The chemical name is 3,3' -azobis (6-hydroxybenzoate)salicylic acid. It is sold as the disodium salt. |
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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. |
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==History== |
==History== |
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The drug is supplied by [[UCB (company)|UCB Pharma]]. |
The drug is supplied by [[UCB (company)|UCB Pharma]]. |
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==Research== |
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==Other indications== |
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In 2006 the Australian biotech company [[Giaconda (pharmaceutical company)|Giaconda]] received a European patent for a combination therapy for treating constipation-predominant [[irritable bowel syndrome]] that uses olsalazine and the anti-[[gout]] drug [[colchicine]], for trials the following year.<ref>{{cite news |title=Giaconda gets European patent for drug |url=https://www.smh.com.au/business/giaconda-gets-european-patent-for-drug-20061228-gdp4vv.html |access-date=16 January 2021 |work=The Sydney Morning Herald |date=28 December 2006 |language=en}}</ref> |
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== |
== References == |
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{{reflist}} |
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*[http://www.olsalazine.com/ Olsalazine official site] |
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*[http://www.medicinenet.com/olsalazine/article.htm Medicine Net] |
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{{Antidiarrheals, intestinal anti-inflammatory/anti-infective agents}} |
{{Antidiarrheals, intestinal anti-inflammatory/anti-infective agents}} |
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{{Portal bar | Medicine}} |
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[[Category:Gastroenterology]] |
[[Category:Gastroenterology]] |
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[[Category: |
[[Category:Hydrazones]] |
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[[Category:Salicylic acids]] |
[[Category:Salicylic acids]] |
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{{gastrointestinal-drug-stub}} |
Latest revision as of 15:41, 12 April 2024
Clinical data | |
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Trade names | Dipentum |
AHFS/Drugs.com | Monograph |
MedlinePlus | a601088 |
License data |
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Pregnancy category |
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Routes of administration | By mouth |
ATC code | |
Legal status | |
Legal status | |
Pharmacokinetic data | |
Protein binding | 99% |
Elimination half-life | 0.9 hours |
Identifiers | |
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 | 302.242 g·mol−1 |
3D model (JSmol) | |
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(what is this?) (verify) |
Olsalazine is an anti-inflammatory medication used in the treatment of ulcerative colitis.[2][3] It is sold under the brand name Dipentum.[4]
Olsalazine itself is a pro-drug of mesalazine (5-aminosalicyclic acid or 5-ASA) and is not absorbed in the small intestine. Instead it continues through to the colon where it is cleaved into two molecules of 5-ASA by azoreductases produced by colonic bacteria. Olsalazine thus exerts its anti-inflammatory effect by its colonic breakdown into 5-ASA which inhibits cyclooxygenase and lipoxygenase thereby reducing prostaglandin and leukotriene production.[4]
History
Olsalazine gained Food and Drug Administration (FDA) approval in 1990.
Supply
The drug is supplied by UCB Pharma.
Research
In 2006 the Australian biotech company Giaconda received a European patent for a combination therapy for treating constipation-predominant irritable bowel syndrome that uses olsalazine and the anti-gout drug colchicine, for trials the following year.[5]
References
- ^ a b "Olsalazine (Dipentum) Use During Pregnancy". Drugs.com. 6 September 2019. Retrieved 9 October 2020.
- ^ "Olsalazine--a further choice in ulcerative colitis". Drug and Therapeutics Bulletin. 28 (15): 57–8. July 1990. doi:10.1136/dtb.28.15.57. PMID 2131213. S2CID 7178709.
- ^ Wadworth AN, Fitton A (April 1991). "Olsalazine. A review of its pharmacodynamic and pharmacokinetic properties, and therapeutic potential in inflammatory bowel disease". Drugs. 41 (4): 647–64. doi:10.2165/00003495-199141040-00009. PMID 1711964. S2CID 243654426.
- ^ a b "Olsalazine Sodium 250 mg Capsules - Summary of Product Characteristics (SmPC) - (emc)". www.medicines.org.uk. Retrieved 9 January 2021.
- ^ "Giaconda gets European patent for drug". The Sydney Morning Herald. 28 December 2006. Retrieved 16 January 2021.