BALSALAZIDE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C17H15N3O6
Molecular Weight	357.3175
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=IPOKCKJONYRRHP-FMQUCBEESA-N

InChI=1S/C17H15N3O6/c21-14-6-5-12(9-13(14)17(25)26)20-19-11-3-1-10(2-4-11)16(24)18-8-7-15(22)23/h1-6,9,21H,7-8H2,(H,18,24)(H,22,23)(H,25,26)/b20-19+

HIDE SMILES / InChI

Molecular Formula	C17H15N3O6
Molecular Weight	357.3175
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	1
Optical Activity	NONE

Description
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/020610s014lbl.pdf
Curator's Comment: description was created based on several sources, including: https://www.drugs.com/pro/balsalazide.html

Balsalazide, a prodrug that is enzymatically cleaved by bacterial azoreduction to release equimolar quantities of mesalamine (5-aminosalicylic acid or 5-ASA) in the colon, an anti-inflammatory drug. The mechanism of action of 5-ASA is unknown, but appears to be local to the colonic mucosa rather than systemic. Balsalazide is indicated for the treatment of mildly to moderately active ulcerative colitis. Most frequently reported adverse events are: headache, abdominal pain, diarrhea, nausea, vomiting, respiratory infection, and arthralgia. The use of orally administered antibiotics could, theoretically, interfere with the release of mesalamine in the colon.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
arachidonic acid metabolic process 3 Target ID: GO:0019369 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/020610s014lbl.pdf	Modulator 817

Conditions

Condition	Modality	Targets	Highest Phase	Product
Ulcerative colitis 122 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/020610s014lbl.pdf	Primary		Approved 8307	COLAZAL Approved Use COLAZAL is indicated for the treatment of mildly to moderately active ulcerative colitis in patients 5 years of age and older. Safety and effectiveness of COLAZAL beyond 8 weeks in children (ages 5-17 years) and 12 weeks in adults have not been established. •COLAZAL is a locally acting aminosalicylate indicated for the treatment of mildly to moderately active ulcerative colitis in patients 5 years of age and older. (1) •Safety and effectiveness of COLAZAL beyond 8 weeks in children (ages 5-17 years) and 12 weeks in adults have not been established. (1) Launch Date 9.6387839E11

C_max

Value	Dose	Co-administered	Analyte	Population
344 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/19633577	6.25 mg 1 times / day multiple, oral dose: 6.25 mg route of administration: Oral experiment type: MULTIPLE co-administered:		MESALAMINE plasma	Homo sapiens population: HEALTHY age: ADOLESCENT sex: FEMALE / MALE food status: UNKNOWN
452 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/19633577	6.75 mg 1 times / day multiple, oral dose: 6.75 mg route of administration: Oral experiment type: MULTIPLE co-administered:		BALSALAZIDE plasma	Homo sapiens population: HEALTHY age: ADOLESCENT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
1931 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/19633577	6.25 mg 1 times / day multiple, oral dose: 6.25 mg route of administration: Oral experiment type: MULTIPLE co-administered:		MESALAMINE plasma	Homo sapiens population: HEALTHY age: ADOLESCENT sex: FEMALE / MALE food status: UNKNOWN
2031 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/19633577	6.75 mg 1 times / day multiple, oral dose: 6.75 mg route of administration: Oral experiment type: MULTIPLE co-administered:		BALSALAZIDE plasma	Homo sapiens population: HEALTHY age: ADOLESCENT sex: FEMALE / MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
6.75 g 1 times / day multiple, oral Dose: 6.75 g, 1 times / day Route: oral Route: multiple Dose: 6.75 g, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/19633577	unhealthy, 12.8 years (range: 5-17 years) n = 33 Health Status: unhealthy Age Group: 12.8 years (range: 5-17 years) Sex: M+F Population Size: 33 Sources: https://pubmed.ncbi.nlm.nih.gov/19633577	Disc. AE: Abdominal pain, Urticaria... AEs leading to discontinuation/dose reduction: Abdominal pain (1 patient) Urticaria (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/19633577
6.6 g 1 times / day multiple, oral Recommended Dose: 6.6 g, 1 times / day Route: oral Route: multiple Dose: 6.6 g, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/022205Orig1s000MedR.pdf Page: p. 61	unhealthy, adult n = 210 Health Status: unhealthy Age Group: adult Population Size: 210 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/022205Orig1s000MedR.pdf Page: p. 61	Disc. AE: Colitis ulcerative, Nausea... AEs leading to discontinuation/dose reduction: Colitis ulcerative (2.4%) Nausea (2%) Vomiting (1%) Erythema nodosum (1%) Frequent bowel movements (1%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/022205Orig1s000MedR.pdf Page: p. 61

AEs

AE	Significance	Dose	Population
Abdominal pain	1 patient Disc. AE	6.75 g 1 times / day multiple, oral Dose: 6.75 g, 1 times / day Route: oral Route: multiple Dose: 6.75 g, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/19633577	unhealthy, 12.8 years (range: 5-17 years) n = 33 Health Status: unhealthy Age Group: 12.8 years (range: 5-17 years) Sex: M+F Population Size: 33 Sources: https://pubmed.ncbi.nlm.nih.gov/19633577
Urticaria	1 patient Disc. AE	6.75 g 1 times / day multiple, oral Dose: 6.75 g, 1 times / day Route: oral Route: multiple Dose: 6.75 g, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/19633577	unhealthy, 12.8 years (range: 5-17 years) n = 33 Health Status: unhealthy Age Group: 12.8 years (range: 5-17 years) Sex: M+F Population Size: 33 Sources: https://pubmed.ncbi.nlm.nih.gov/19633577
Erythema nodosum	1% Disc. AE	6.6 g 1 times / day multiple, oral Recommended Dose: 6.6 g, 1 times / day Route: oral Route: multiple Dose: 6.6 g, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/022205Orig1s000MedR.pdf Page: p. 61	unhealthy, adult n = 210 Health Status: unhealthy Age Group: adult Population Size: 210 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/022205Orig1s000MedR.pdf Page: p. 61
Frequent bowel movements	1% Disc. AE	6.6 g 1 times / day multiple, oral Recommended Dose: 6.6 g, 1 times / day Route: oral Route: multiple Dose: 6.6 g, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/022205Orig1s000MedR.pdf Page: p. 61	unhealthy, adult n = 210 Health Status: unhealthy Age Group: adult Population Size: 210 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/022205Orig1s000MedR.pdf Page: p. 61
Vomiting	1% Disc. AE	6.6 g 1 times / day multiple, oral Recommended Dose: 6.6 g, 1 times / day Route: oral Route: multiple Dose: 6.6 g, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/022205Orig1s000MedR.pdf Page: p. 61	unhealthy, adult n = 210 Health Status: unhealthy Age Group: adult Population Size: 210 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/022205Orig1s000MedR.pdf Page: p. 61
Nausea	2% Disc. AE	6.6 g 1 times / day multiple, oral Recommended Dose: 6.6 g, 1 times / day Route: oral Route: multiple Dose: 6.6 g, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/022205Orig1s000MedR.pdf Page: p. 61	unhealthy, adult n = 210 Health Status: unhealthy Age Group: adult Population Size: 210 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/022205Orig1s000MedR.pdf Page: p. 61
Colitis ulcerative	2.4% Disc. AE	6.6 g 1 times / day multiple, oral Recommended Dose: 6.6 g, 1 times / day Route: oral Route: multiple Dose: 6.6 g, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/022205Orig1s000MedR.pdf Page: p. 61	unhealthy, adult n = 210 Health Status: unhealthy Age Group: adult Population Size: 210 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/022205Orig1s000MedR.pdf Page: p. 61

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
	inhibitor 1695	inhibitor 1789

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1463 CYP2C19 1410 CYP3A4/5 261 CYP2A6 670 CYP2E1 846 UGT1A6 107 UGT1A9 115 OATP1A2 34 OATP1B1 770 OATP1B3 691 OATP2B1 121 BSEP 392 MRP2 363 BCRP 678	OATP2B1 103 OATP1B1 389 OATP1B3 333

Drug as perpetrator

Target	Modality	Activity	Metabolite
CYP2A6 702	inhibitor 3185 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw1MjgyIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDEyMDEzNDYifX0%3D	no [IC50 >10 uM]
CYP2E1 929	inhibitor 3185 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw1MjgxIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDEyMDEzNDYifX0%3D	no [IC50 >10 uM]
BCRP 751	inhibitor 3185 Sources: https://pubmed.ncbi.nlm.nih.gov/19421845/	no	5-ASA 3
CYP1A2 1620	inhibitor 3185 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/020610s023lbl.pdf#page=11 Page: 11.0	no
CYP1A2 1620	inhibitor 3185 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/020610s023lbl.pdf#page=11 Page: 11.0	no	5-ASA 3
CYP2C19 1484	inhibitor 3185 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/020610s023lbl.pdf#page=11 Page: 11.0	no
CYP2C19 1484	inhibitor 3185 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/020610s023lbl.pdf#page=11 Page: 11.0	no	5-ASA 3
CYP2C9 1747	inhibitor 3185 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/020610s023lbl.pdf#page=11 Page: 11.0	no
CYP2C9 1747	inhibitor 3185 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/020610s023lbl.pdf#page=11 Page: 11.0	no	5-ASA 3
CYP2D6 1826	inhibitor 3185 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/020610s023lbl.pdf#page=11 Page: 11.0	no
CYP2D6 1826	inhibitor 3185 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/020610s023lbl.pdf#page=11 Page: 11.0	no	5-ASA 3
CYP3A4/5 314	inhibitor 3185 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/020610s023lbl.pdf#page=11 Page: 11.0	no
CYP3A4/5 314	inhibitor 3185 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/020610s023lbl.pdf#page=11 Page: 11.0	no	5-ASA 3
MRP2 452	inhibitor 3185 Sources: https://pubmed.ncbi.nlm.nih.gov/18457386/	no	5-ASA 3
OATP1A2 34	inhibitor 3185 Sources: https://scholar.google.com/scholar?hl=ja&as_sdt=0%2C33&q=Role+of+Organic+Anion-Transporting+Polypeptides+for+Cellular+Mesalazine+%285-Aminosalicylic+Acid%29+Uptake&btnG=	no	5-ASA 3
OATP2B1 124	inhibitor 3185 Sources: https://scholar.google.com/scholar?hl=ja&as_sdt=0%2C33&q=Role+of+Organic+Anion-Transporting+Polypeptides+for+Cellular+Mesalazine+%285-Aminosalicylic+Acid%29+Uptake&btnG=	no	5-ASA 3
UGT1A6 139	inhibitor 3185 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNzQzMzE2IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDcwNCJ9fQ%3D%3D	no	5-ASA 3
UGT1A9 120	inhibitor 3185 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNzQzMzE2IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDcwNCJ9fQ%3D%3D	no	5-ASA 3
BSEP 393	inhibitor 3185 Sources: https://pubmed.ncbi.nlm.nih.gov/22961681/	weak [IC50 381.4 uM]	5-ASA 3
OATP1B1 785	inhibitor 3185 Sources: https://scholar.google.com/scholar?hl=ja&as_sdt=0%2C33&q=Role+of+Organic+Anion-Transporting+Polypeptides+for+Cellular+Mesalazine+%285-Aminosalicylic+Acid%29+Uptake&btnG=	yes	5-ASA 3
OATP1B3 700	inhibitor 3185 Sources: https://scholar.google.com/scholar?hl=ja&as_sdt=0%2C33&q=Role+of+Organic+Anion-Transporting+Polypeptides+for+Cellular+Mesalazine+%285-Aminosalicylic+Acid%29+Uptake&btnG=	yes	5-ASA 3

Drug as victim

Target	Modality	Activity	Metabolite
OATP2B1 103	substrate 3264 Sources: https://scholar.google.com/scholar?hl=ja&as_sdt=0%2C33&q=Role+of+Organic+Anion-Transporting+Polypeptides+for+Cellular+Mesalazine+%285-Aminosalicylic+Acid%29+Uptake&btnG=	yes [Km 188.9 uM]	5-ASA 3
OATP1B1 389	substrate 3264 Sources: https://scholar.google.com/scholar?hl=ja&as_sdt=0%2C33&q=Role+of+Organic+Anion-Transporting+Polypeptides+for+Cellular+Mesalazine+%285-Aminosalicylic+Acid%29+Uptake&btnG=	yes [Km 55.1 uM]	5-ASA 3
OATP1B3 333	substrate 3264 Sources: https://scholar.google.com/scholar?hl=ja&as_sdt=0%2C33&q=Role+of+Organic+Anion-Transporting+Polypeptides+for+Cellular+Mesalazine+%285-Aminosalicylic+Acid%29+Uptake&btnG=	yes [Km 77.4 uM]	5-ASA 3
OATP2B1 103	substrate 3264 Sources: https://pubmed.ncbi.nlm.nih.gov/32189541/	yes

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:267413	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:267413
ChemicalBook	CB9148828	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB9148828
MolPort	MolPort-005-934-178	https://www.molport.com/shop/molecule-link/MolPort-005-934-178
ZINC	ZINC000003952881	http://zinc15.docking.org/substances/ZINC000003952881
eMolecules	18597217	https://www.emolecules.com/cgi-bin/more?vid=18597217

PubMed

Title	Date	PubMed
Maintenance of remission of ulcerative colitis: a comparison between balsalazide 3 g daily and mesalazine 1.2 g daily over 12 months. ABACUS Investigator group.	1998 Dec	9882028
Review article: balsalazide therapy in ulcerative colitis.	2001 Oct	11563993
Prediction of genotoxicity of chemical compounds by statistical learning methods.	2005 Jun	15962942
Balsalazide and/or high-potency probiotic mixture (VSL#3) in maintaining remission after attack of acute, uncomplicated diverticulitis of the colon.	2007 Sep	17390144
Balsalazide-induced myocarditis.	2008 Nov 28	17889383
Unilateral balsalazide-induced eosinophilic pneumonia in an ulcerative colitis patient.	2010 Sep	21127763

Patents

Sample Use Guides

In Vivo Use Guide

Three 750 mg COLAZAL capsules to be taken three times a day for a total daily dose of 6.75 grams for a duration of 8 weeks. Some patients in the clinical trials required treatment for up to 12 weeks.

Route of Administration: Oral

In Vitro Use Guide

Mean equivalent doses (0.1 to 10 mM) of balsalazide (range, 6.3 +/- 1.5 to 16.7 +/- 1.3 microA/cm2) significantly stimulated (P < 0.001) secretion in rabbit distal ileum. The value for the effective dose that is half the maximal dose for secretion induced by 0.9 mM.

Substance Class	Chemical Created by `admin` on `Sun Dec 18 17:49:50 UTC 2022` Edited by `admin` on `Sun Dec 18 17:49:50 UTC 2022`
Record UNII	P80AL8J7ZP
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

BALSALAZIDE

Official Name

English

balsalazide [INN]

Common Name

English

BALSALAZIDE [VANDF]

Common Name

English

5-((4-((2-CARBOXYETHYL)CARBAMOYL)PHENYL)DIAZENYL)-2-HYDROXYBENZOIC ACID

Systematic Name

English

BALSALAZIDE [MI]

Common Name

English

Balsalazide [WHO-DD]

Common Name

English

BENZOIC ACID, 5-((4-(((2-CARBOXYETHYL)AMINO)CARBONYL)PHENYL)AZO)-2-HYDROXY-

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C257