Details
Stereochemistry | ACHIRAL |
Molecular Formula | C14H8N2O6.2Na |
Molecular Weight | 346.2027 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 1 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[Na+].[Na+].OC1=C(C=C(C=C1)\N=N\C2=CC(C([O-])=O)=C(O)C=C2)C([O-])=O
InChI
InChIKey=ZJEFYLVGGFISGT-VRZXRVJBSA-L
InChI=1S/C14H10N2O6.2Na/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);;/q;2*+1/p-2/b16-15+;;
Olsalazine is an anti-inflammatory drug used in the treatment of inflammatory bowel disease such as ulcerative colitis. Orally administered olsalazine is converted to mesalamine which is thought to be the therapeutically active agent in the treatment of ulcerative colitis. The mechanism of action of mesalamine (and sulfasalazine) is unknown but appears to be topical rather than systemic. Mucosal production of arachidonic acid (AA) metabolites, both through the cyclooxygenase pathways, i.e., prostanoids, and through the lipoxygenase pathways, i.e., leukotrienes (LTs) and hydroxyelcosatetraenoic acids (HETEs) is increased in patients with chronic inflammatory bowel disease, and it is possible that mesalamine diminishes inflammation by blocking cyclooxygenase and inhibiting prostaglandin (PG) production in the colon. After oral administration, olsalazine has limited systemic bioavailability. Based on oral and intravenous dosing studies, approximately 2.4% of a single 1.0 g oral dose is absorbed. Less than 1% of olsalazine is recovered in the urine. The remaining 98 to 99% of an oral dose will reach the colon, where each molecule is rapidly converted into two molecules of 5¬ aminosalicylic acid (5-ASA) by colonic bacteria and the low prevailing redox potential found in this environment. The liberated 5-ASA is absorbed slowly resulting in very high local concentrations in the colon. Olsalazine has been evaluated in ulcerative colitis patients in remission, as well as those with acute disease. Both sulfasalazine-tolerant and intolerant patients have been studied in controlled clinical trials. Overall, 10.4% of patients discontinued olsalazine because of an adverse experience compared with 6.7% of placebo patients. The most commonly reported adverse reactions leading to treatment withdrawal were diarrhea or loose stools (olsalazine 5.9%; placebo 4.8%), abdominal pain, and rash or itching (slightly more than 1% of patients receiving olsalazine).
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2094253 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | DIPENTUM Approved UseOlsalazine is indicated for the maintenance of remission of ulcerative colitis in patients who are intolerant of sulfasalazine. Launch Date1990 |
|||
Primary | DIPENTUM Approved UseOlsalazine is indicated for the maintenance of remission of ulcerative colitis in patients who are intolerant of sulfasalazine. Launch Date1990 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
32 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3203708/ |
4 g single, oral dose: 4 g route of administration: Oral experiment type: SINGLE co-administered: |
OLSALAZINE serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
2.3 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3203708/ |
1 g single, oral dose: 1 g route of administration: Oral experiment type: SINGLE co-administered: |
OLSALAZINE serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
3.6 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3203708/ |
1 g single, oral dose: 1 g route of administration: Oral experiment type: SINGLE co-administered: |
OLSALAZINE serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
5.9 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3203708/ |
2 g single, oral dose: 2 g route of administration: Oral experiment type: SINGLE co-administered: |
OLSALAZINE serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
7.5 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3203708/ |
10 mg single, intravenous dose: 10 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
OLSALAZINE serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
117 μM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3203708/ |
4 g single, oral dose: 4 g route of administration: Oral experiment type: SINGLE co-administered: |
OLSALAZINE serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
13 μM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3203708/ |
1 g single, oral dose: 1 g route of administration: Oral experiment type: SINGLE co-administered: |
OLSALAZINE serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
13 μM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3203708/ |
1 g single, oral dose: 1 g route of administration: Oral experiment type: SINGLE co-administered: |
OLSALAZINE serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
22 μM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3203708/ |
2 g single, oral dose: 2 g route of administration: Oral experiment type: SINGLE co-administered: |
OLSALAZINE serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
6.5 μM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3203708/ |
10 mg single, intravenous dose: 10 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
OLSALAZINE serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
56 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3203708/ |
10 mg single, intravenous dose: 10 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
OLSALAZINE serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
4 g 1 times / day single, oral Highest studied dose Dose: 4 g, 1 times / day Route: oral Route: single Dose: 4 g, 1 times / day Sources: |
healthy, 27-44 n = 5 Health Status: healthy Age Group: 27-44 Sex: M Population Size: 5 Sources: |
Other AEs: Diarrhea... |
10 mg 1 times / day single, intravenous Highest studied dose Dose: 10 mg, 1 times / day Route: intravenous Route: single Dose: 10 mg, 1 times / day Sources: |
healthy, 27-44 n = 7 Health Status: healthy Age Group: 27-44 Sex: M Population Size: 7 Sources: |
|
1 g 4 times / day multiple, oral Highest studied dose Dose: 1 g, 4 times / day Route: oral Route: multiple Dose: 1 g, 4 times / day Sources: |
unhealthy, 34 (19-66) n = 31 Health Status: unhealthy Condition: Ulcerative colitis Age Group: 34 (19-66) Sex: M+F Population Size: 31 Sources: |
Disc. AE: Loose stools, Loose stools... AEs leading to discontinuation/dose reduction: Loose stools Sources: Loose stools |
0.6 g 2 times / day multiple, oral (mean) Recommended Dose: 0.6 g, 2 times / day Route: oral Route: multiple Dose: 0.6 g, 2 times / day Sources: |
unhealthy, adult n = 804 Health Status: unhealthy Age Group: adult Sex: M+F Population Size: 804 Sources: |
Disc. AE: Diarrhoea, Nausea... AEs leading to discontinuation/dose reduction: Diarrhoea Sources: Nausea Headache Loose stools Abdominal pain Rash Alopecia Dizziness Light headedness |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Diarrhea | 4 g 1 times / day single, oral Highest studied dose Dose: 4 g, 1 times / day Route: oral Route: single Dose: 4 g, 1 times / day Sources: |
healthy, 27-44 n = 5 Health Status: healthy Age Group: 27-44 Sex: M Population Size: 5 Sources: |
|
Loose stools | Disc. AE | 1 g 4 times / day multiple, oral Highest studied dose Dose: 1 g, 4 times / day Route: oral Route: multiple Dose: 1 g, 4 times / day Sources: |
unhealthy, 34 (19-66) n = 31 Health Status: unhealthy Condition: Ulcerative colitis Age Group: 34 (19-66) Sex: M+F Population Size: 31 Sources: |
Loose stools | Disc. AE | 1 g 4 times / day multiple, oral Highest studied dose Dose: 1 g, 4 times / day Route: oral Route: multiple Dose: 1 g, 4 times / day Sources: |
unhealthy, 34 (19-66) n = 31 Health Status: unhealthy Condition: Ulcerative colitis Age Group: 34 (19-66) Sex: M+F Population Size: 31 Sources: |
Abdominal pain | Disc. AE | 0.6 g 2 times / day multiple, oral (mean) Recommended Dose: 0.6 g, 2 times / day Route: oral Route: multiple Dose: 0.6 g, 2 times / day Sources: |
unhealthy, adult n = 804 Health Status: unhealthy Age Group: adult Sex: M+F Population Size: 804 Sources: |
Alopecia | Disc. AE | 0.6 g 2 times / day multiple, oral (mean) Recommended Dose: 0.6 g, 2 times / day Route: oral Route: multiple Dose: 0.6 g, 2 times / day Sources: |
unhealthy, adult n = 804 Health Status: unhealthy Age Group: adult Sex: M+F Population Size: 804 Sources: |
Diarrhoea | Disc. AE | 0.6 g 2 times / day multiple, oral (mean) Recommended Dose: 0.6 g, 2 times / day Route: oral Route: multiple Dose: 0.6 g, 2 times / day Sources: |
unhealthy, adult n = 804 Health Status: unhealthy Age Group: adult Sex: M+F Population Size: 804 Sources: |
Dizziness | Disc. AE | 0.6 g 2 times / day multiple, oral (mean) Recommended Dose: 0.6 g, 2 times / day Route: oral Route: multiple Dose: 0.6 g, 2 times / day Sources: |
unhealthy, adult n = 804 Health Status: unhealthy Age Group: adult Sex: M+F Population Size: 804 Sources: |
Headache | Disc. AE | 0.6 g 2 times / day multiple, oral (mean) Recommended Dose: 0.6 g, 2 times / day Route: oral Route: multiple Dose: 0.6 g, 2 times / day Sources: |
unhealthy, adult n = 804 Health Status: unhealthy Age Group: adult Sex: M+F Population Size: 804 Sources: |
Light headedness | Disc. AE | 0.6 g 2 times / day multiple, oral (mean) Recommended Dose: 0.6 g, 2 times / day Route: oral Route: multiple Dose: 0.6 g, 2 times / day Sources: |
unhealthy, adult n = 804 Health Status: unhealthy Age Group: adult Sex: M+F Population Size: 804 Sources: |
Loose stools | Disc. AE | 0.6 g 2 times / day multiple, oral (mean) Recommended Dose: 0.6 g, 2 times / day Route: oral Route: multiple Dose: 0.6 g, 2 times / day Sources: |
unhealthy, adult n = 804 Health Status: unhealthy Age Group: adult Sex: M+F Population Size: 804 Sources: |
Nausea | Disc. AE | 0.6 g 2 times / day multiple, oral (mean) Recommended Dose: 0.6 g, 2 times / day Route: oral Route: multiple Dose: 0.6 g, 2 times / day Sources: |
unhealthy, adult n = 804 Health Status: unhealthy Age Group: adult Sex: M+F Population Size: 804 Sources: |
Rash | Disc. AE | 0.6 g 2 times / day multiple, oral (mean) Recommended Dose: 0.6 g, 2 times / day Route: oral Route: multiple Dose: 0.6 g, 2 times / day Sources: |
unhealthy, adult n = 804 Health Status: unhealthy Age Group: adult Sex: M+F Population Size: 804 Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
yes | ||||
yes |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 2.0 |
no | |||
Page: 2.0 |
yes |
PubMed
Title | Date | PubMed |
---|---|---|
Effect of anti-inflammatory drugs on xanthine oxidase and xanthine oxidase induced depolymerization of hyaluronic acid. | 1985 Jul |
|
Mesalazine-associated tubulo-interstitial nephritis in inflammatory bowel disease. | 1998 Apr |
|
Renal dysfunction and the treatment of inflammatory bowel disease (IBD): a case for monitoring. | 1998 Jun |
|
Glomerular and tubular renal functions after long-term medication of sulphasalazine, olsalazine, and mesalazine in patients with ulcerative colitis. | 2000 Nov |
|
Prediction of genotoxicity of chemical compounds by statistical learning methods. | 2005 Jun |
Patents
Sample Use Guides
The usual dosage in adults for maintenance of remission is 1.0 g/day in two divided doses.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7729283
Male Sprague-Dawley rats fed ad libitum and weighing 400-500 g, were anesthetized using ketamine and xylazine. An ileal segment 15 cm proximal to ileocecal valve was stripped away from the mesentery and everted. Segments, about 3 cm long and apparently free of Peyer's patches, were cut from the long everted ileal segment. A suture was tightly placed near one end of each of these segments. After stretching with a 5-g weight attached to the unsutured end, a loose tie was made 2.5 cm from the first suture. Sacs were weighed with the sutures. Using a 16 G angiocath, 0.25 ml of 100mkM [3H]Tc (taurocholate) was injected into the lumen and the second suture tightened. Sacs were reweighed and incubated in oxygenated KRB solution at 37°C in a shaking water bath for 10 min. OLZ (Olsalazine) was added to the flask to a final concentration of 5 mM, incubated for 30 min, and [3H]Tc (final concentration 100 mkM) added to each flask. Ten minutes after addition of Tc, the sacs were removed and weighed. The lumen of each sac was aspirated and 100 mk1 of the aspirate was placed in a scintillation vial for determination of Tc concentration. Each sac was cut, weighed, and placed over 25-mm nitrocellutose filters (Gelman, Ann Arbor, Michigan) in a Millipore multiwall manifold. Tissues were washed with 30 ml of ice cold saline
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NCI_THESAURUS |
C257
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ACTIVE MOIETY
SUBSTANCE RECORD