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Details

Stereochemistry ACHIRAL
Molecular Formula C14H10N2O6
Molecular Weight 302.2395
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of OLSALAZINE

SMILES

c1cc(c(cc1/N=N/c2ccc(c(c2)C(=O)O)O)C(=O)O)O

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
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
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

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
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 Sat Jun 26 04:47:43 UTC 2021 , Edited by admin on Sat Jun 26 04:47:43 UTC 2021
NCI_THESAURUS C257
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NDF-RT N0000005760
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NDF-RT N0000005760
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NDF-RT N0000005760
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WHO-VATC QA07EC03
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NDF-RT N0000175781
Created by admin on Sat Jun 26 04:47:43 UTC 2021 , Edited by admin on Sat Jun 26 04:47:43 UTC 2021
NDF-RT N0000005760
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LIVERTOX 707
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Code System Code Type Description
ChEMBL
CHEMBL425
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PRIMARY
CAS
15722-48-2
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PRIMARY
DRUG CENTRAL
1988
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PRIMARY
MERCK INDEX
M8205
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PRIMARY Merck Index
MESH
C032587
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PRIMARY
WIKIPEDIA
OLSALAZINE
Created by admin on Sat Jun 26 04:47:43 UTC 2021 , Edited by admin on Sat Jun 26 04:47:43 UTC 2021
PRIMARY
EPA CompTox
15722-48-2
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PRIMARY
DRUG BANK
DB01250
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PRIMARY
RXCUI
32385
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PRIMARY RxNorm
NCI_THESAURUS
C1176
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PRIMARY
INN
5607
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PRIMARY
LACTMED
Olsalazine
Created by admin on Sat Jun 26 04:47:43 UTC 2021 , Edited by admin on Sat Jun 26 04:47:43 UTC 2021
PRIMARY
FDA UNII
ULS5I8J03O
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PRIMARY
EVMPD
SUB09436MIG
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PRIMARY