U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C14H10N2O6
Molecular Weight 302.239
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of OLSALAZINE

SMILES

OC(=O)C1=CC(=CC=C1O)\N=N\C2=CC(C(O)=O)=C(O)C=C2

InChI

InChIKey=QQBDLJCYGRGAKP-FOCLMDBBSA-N
InChI=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+

HIDE SMILES / InChI

Molecular Formula C14H10N2O6
Molecular Weight 302.239
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Description

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

Originator

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
DIPENTUM
Primary
DIPENTUM
PubMed

PubMed

TitleDatePubMed
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
Drug-associated acute pancreatitis: twenty-one years of spontaneous reporting in The Netherlands.
1999 Sep
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

In Vivo Use Guide
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
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
Substance Class Chemical
Created
by admin
on Tue Oct 22 00:22:49 UTC 2019
Edited
by admin
on Tue Oct 22 00:22:49 UTC 2019
Record UNII
ULS5I8J03O
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
OLSALAZINE
INN   MI   VANDF   WHO-DD  
INN  
Official Name English
OLSALAZINE [MI]
Common Name English
OLSALAZINE [VANDF]
Common Name English
C. I. MORDANT YELLOW 5
Common Name English
BENZOIC ACID, 3,3'-AZOBIS(6-HYDROXY-
Common Name English
OLSALAZINE [INN]
Common Name English
OLSALAZINE [WHO-DD]
Common Name English
5,5'-AZODISALICYLIC ACID
Systematic Name English
Classification Tree Code System Code
WHO-ATC A07EC03
Created by admin on Tue Oct 22 00:22:49 UTC 2019 , Edited by admin on Tue Oct 22 00:22:49 UTC 2019
NCI_THESAURUS C257
Created by admin on Tue Oct 22 00:22:49 UTC 2019 , Edited by admin on Tue Oct 22 00:22:49 UTC 2019
NDF-RT N0000005760
Created by admin on Tue Oct 22 00:22:49 UTC 2019 , Edited by admin on Tue Oct 22 00:22:49 UTC 2019
NDF-RT N0000005760
Created by admin on Tue Oct 22 00:22:49 UTC 2019 , Edited by admin on Tue Oct 22 00:22:49 UTC 2019
NDF-RT N0000005760
Created by admin on Tue Oct 22 00:22:49 UTC 2019 , Edited by admin on Tue Oct 22 00:22:49 UTC 2019
WHO-VATC QA07EC03
Created by admin on Tue Oct 22 00:22:49 UTC 2019 , Edited by admin on Tue Oct 22 00:22:49 UTC 2019
NDF-RT N0000175781
Created by admin on Tue Oct 22 00:22:49 UTC 2019 , Edited by admin on Tue Oct 22 00:22:49 UTC 2019
NDF-RT N0000005760
Created by admin on Tue Oct 22 00:22:49 UTC 2019 , Edited by admin on Tue Oct 22 00:22:49 UTC 2019
LIVERTOX 707
Created by admin on Tue Oct 22 00:22:49 UTC 2019 , Edited by admin on Tue Oct 22 00:22:49 UTC 2019
Code System Code Type Description
LactMed
15722-48-2
Created by admin on Tue Oct 22 00:22:49 UTC 2019 , Edited by admin on Tue Oct 22 00:22:49 UTC 2019
PRIMARY
ChEMBL
CHEMBL425
Created by admin on Tue Oct 22 00:22:49 UTC 2019 , Edited by admin on Tue Oct 22 00:22:49 UTC 2019
PRIMARY
CAS
15722-48-2
Created by admin on Tue Oct 22 00:22:49 UTC 2019 , Edited by admin on Tue Oct 22 00:22:49 UTC 2019
PRIMARY
MERCK INDEX
M8205
Created by admin on Tue Oct 22 00:22:49 UTC 2019 , Edited by admin on Tue Oct 22 00:22:49 UTC 2019
PRIMARY Merck Index
MESH
C032587
Created by admin on Tue Oct 22 00:22:49 UTC 2019 , Edited by admin on Tue Oct 22 00:22:49 UTC 2019
PRIMARY
WIKIPEDIA
OLSALAZINE
Created by admin on Tue Oct 22 00:22:49 UTC 2019 , Edited by admin on Tue Oct 22 00:22:49 UTC 2019
PRIMARY
EPA CompTox
15722-48-2
Created by admin on Tue Oct 22 00:22:49 UTC 2019 , Edited by admin on Tue Oct 22 00:22:49 UTC 2019
PRIMARY
DRUG BANK
DB01250
Created by admin on Tue Oct 22 00:22:49 UTC 2019 , Edited by admin on Tue Oct 22 00:22:49 UTC 2019
PRIMARY
RXCUI
32385
Created by admin on Tue Oct 22 00:22:49 UTC 2019 , Edited by admin on Tue Oct 22 00:22:49 UTC 2019
PRIMARY RxNorm
NCI_THESAURUS
C1176
Created by admin on Tue Oct 22 00:22:49 UTC 2019 , Edited by admin on Tue Oct 22 00:22:49 UTC 2019
PRIMARY
INN
5607
Created by admin on Tue Oct 22 00:22:49 UTC 2019 , Edited by admin on Tue Oct 22 00:22:49 UTC 2019
PRIMARY
EVMPD
SUB09436MIG
Created by admin on Tue Oct 22 00:22:49 UTC 2019 , Edited by admin on Tue Oct 22 00:22:49 UTC 2019
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
BINDER->LIGAND
BINDING
Related Record Type Details
METABOLITE ACTIVE -> PRODRUG
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC