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

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
Structure of OLSALAZINE SODIUM

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+;;

HIDE SMILES / InChI

Molecular Formula Na
Molecular Weight 22.9898
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C14H8N2O6
Molecular Weight 300.2231
Charge -2
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

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).

Originator

Sources: Atti X° congr. intern. chim. Volume 3, Pages 46-57, Journal, 1939

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
DIPENTUM

Approved Use

Olsalazine is indicated for the maintenance of remission of ulcerative colitis in patients who are intolerant of sulfasalazine.

Launch Date

6.493824E11
Primary
DIPENTUM

Approved Use

Olsalazine is indicated for the maintenance of remission of ulcerative colitis in patients who are intolerant of sulfasalazine.

Launch Date

6.493824E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
32 μM
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
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
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
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
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

AUC

ValueDoseCo-administeredAnalytePopulation
117 μM × h
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
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
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
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
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

T1/2

ValueDoseCo-administeredAnalytePopulation
56 min
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

Doses

DosePopulationAdverse 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...
Other AEs:
Diarrhea
Sources:
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
Loose stools
Sources:
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
Nausea
Headache
Loose stools
Abdominal pain
Rash
Alopecia
Dizziness
Light headedness
Sources:
AEs

AEs

AESignificanceDosePopulation
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

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer




Drug as perpetrator​Drug as victim
PubMed

PubMed

TitleDatePubMed
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
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
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 Wed Jul 05 23:54:11 UTC 2023
Edited
by admin
on Wed Jul 05 23:54:11 UTC 2023
Record UNII
Y7JEW0XG7I
Record Status Validated (UNII)
Record Version
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Name Type Language
OLSALAZINE SODIUM
EP   MART.   ORANGE BOOK   USAN   VANDF   WHO-DD  
USAN  
Official Name English
CJ 91B
Code English
OLSALAZINE SODIUM [EP IMPURITY]
Common Name English
OLSALAZINE SODIUM [EP MONOGRAPH]
Common Name English
BENZOIC ACID, 3,3'-AZOBIS(6-HYDROXY-, DISODIUM SALT
Common Name English
DIPENTUM
Brand Name English
CJ-91B
Code English
OLSALAZINE DISODIUM SALT
MI  
Common Name English
SODIUM OLSALAZINE
Common Name English
Olsalazine sodium [WHO-DD]
Common Name English
OLSALAZINE SODIUM [MART.]
Common Name English
C. I. Mordant Yellow 5, disodium salt
Common Name English
OLSALAZINE SODIUM [VANDF]
Common Name English
AZODISAL SODIUM
Common Name English
OLSALAZINE SODIUM [ORANGE BOOK]
Common Name English
DISODIUM 5,5'-AZODISALICYLATE
Systematic Name English
OLSALAZINE SODIUM [USAN]
Common Name English
OLSALAZINE DISODIUM SALT [MI]
Common Name English
DISODIUM AZODISALICYLATE
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C257
Created by admin on Wed Jul 05 23:54:11 UTC 2023 , Edited by admin on Wed Jul 05 23:54:11 UTC 2023
Code System Code Type Description
SMS_ID
100000091274
Created by admin on Wed Jul 05 23:54:11 UTC 2023 , Edited by admin on Wed Jul 05 23:54:11 UTC 2023
PRIMARY
NCI_THESAURUS
C66254
Created by admin on Wed Jul 05 23:54:11 UTC 2023 , Edited by admin on Wed Jul 05 23:54:11 UTC 2023
PRIMARY
EVMPD
SUB03510MIG
Created by admin on Wed Jul 05 23:54:11 UTC 2023 , Edited by admin on Wed Jul 05 23:54:11 UTC 2023
PRIMARY
USAN
Z-16
Created by admin on Wed Jul 05 23:54:11 UTC 2023 , Edited by admin on Wed Jul 05 23:54:11 UTC 2023
PRIMARY
ChEMBL
CHEMBL425
Created by admin on Wed Jul 05 23:54:11 UTC 2023 , Edited by admin on Wed Jul 05 23:54:11 UTC 2023
PRIMARY
CAS
6054-98-4
Created by admin on Wed Jul 05 23:54:11 UTC 2023 , Edited by admin on Wed Jul 05 23:54:11 UTC 2023
PRIMARY
ECHA (EC/EINECS)
227-975-7
Created by admin on Wed Jul 05 23:54:11 UTC 2023 , Edited by admin on Wed Jul 05 23:54:11 UTC 2023
PRIMARY
DRUG BANK
DBSALT000191
Created by admin on Wed Jul 05 23:54:11 UTC 2023 , Edited by admin on Wed Jul 05 23:54:11 UTC 2023
PRIMARY
MERCK INDEX
M8205
Created by admin on Wed Jul 05 23:54:11 UTC 2023 , Edited by admin on Wed Jul 05 23:54:11 UTC 2023
PRIMARY Merck Index
FDA UNII
Y7JEW0XG7I
Created by admin on Wed Jul 05 23:54:11 UTC 2023 , Edited by admin on Wed Jul 05 23:54:11 UTC 2023
PRIMARY
EPA CompTox
DTXSID3046796
Created by admin on Wed Jul 05 23:54:11 UTC 2023 , Edited by admin on Wed Jul 05 23:54:11 UTC 2023
PRIMARY
CHEBI
63614
Created by admin on Wed Jul 05 23:54:11 UTC 2023 , Edited by admin on Wed Jul 05 23:54:11 UTC 2023
PRIMARY
RXCUI
104123
Created by admin on Wed Jul 05 23:54:11 UTC 2023 , Edited by admin on Wed Jul 05 23:54:11 UTC 2023
PRIMARY RxNorm
DAILYMED
Y7JEW0XG7I
Created by admin on Wed Jul 05 23:54:11 UTC 2023 , Edited by admin on Wed Jul 05 23:54:11 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY