BALSALAZIDE DISODIUM ANHYDROUS

Details

Stereochemistry	ACHIRAL
Molecular Formula	C17H13N3O6.2Na
Molecular Weight	401.2812
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure of BALSALAZIDE DISODIUM ANHYDROUS

Structure Search

SMILES

[Na+].[Na+].OC1=CC=C(C=C1C([O-])=O)\N=N\C2=CC=C(C=C2)C(=O)NCCC([O-])=O

InChI

InChIKey=CKMOQBVBEGCJGW-LLIZZRELSA-L

InChI=1S/C17H15N3O6.2Na/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);;/q;2*+1/p-2/b20-19+;;

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	C17H13N3O6
Molecular Weight	355.3016
Charge	-2
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 828

Conditions

Condition	Modality	Targets	Highest Phase	Product
Ulcerative colitis 123 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/020610s014lbl.pdf	Primary		Approved 8429	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 1767	inhibitor 1852

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1524 CYP2C19 1478 CYP3A4/5 278 CYP2A6 707 CYP2E1 882 UGT1A6 108 UGT1A9 116 OATP1A2 35 OATP1B1 788 OATP1B3 706 OATP2B1 123 BSEP 402 MRP2 383 BCRP 699	OATP2B1 104 OATP1B1 406 OATP1B3 350

Drug as perpetrator

Target	Modality	Activity	Metabolite
CYP2A6 739	inhibitor 3277 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw1MjgyIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDEyMDEzNDYifX0%3D	no [IC50 >10 uM]
CYP2E1 970	inhibitor 3277 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw1MjgxIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDEyMDEzNDYifX0%3D	no [IC50 >10 uM]
BCRP 773	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/19421845/	no	5-ASA 3
CYP1A2 1692	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/020610s023lbl.pdf#page=11 Page: 11.0	no
CYP1A2 1692	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/020610s023lbl.pdf#page=11 Page: 11.0	no	5-ASA 3
CYP2C19 1553	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/020610s023lbl.pdf#page=11 Page: 11.0	no
CYP2C19 1553	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/020610s023lbl.pdf#page=11 Page: 11.0	no	5-ASA 3
CYP2C9 1819	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/020610s023lbl.pdf#page=11 Page: 11.0	no
CYP2C9 1819	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/020610s023lbl.pdf#page=11 Page: 11.0	no	5-ASA 3
CYP2D6 1891	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/020610s023lbl.pdf#page=11 Page: 11.0	no
CYP2D6 1891	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/020610s023lbl.pdf#page=11 Page: 11.0	no	5-ASA 3
CYP3A4/5 335	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/020610s023lbl.pdf#page=11 Page: 11.0	no
CYP3A4/5 335	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/020610s023lbl.pdf#page=11 Page: 11.0	no	5-ASA 3
MRP2 475	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/18457386/	no	5-ASA 3
OATP1A2 35	inhibitor 3277 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 126	inhibitor 3277 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 141	inhibitor 3277 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNzQzMzE2IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDcwNCJ9fQ%3D%3D	no	5-ASA 3
UGT1A9 121	inhibitor 3277 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNzQzMzE2IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDcwNCJ9fQ%3D%3D	no	5-ASA 3
BSEP 403	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/22961681/	weak [IC50 381.4 uM]	5-ASA 3
OATP1B1 803	inhibitor 3277 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 715	inhibitor 3277 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 104	substrate 3367 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 406	substrate 3367 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 350	substrate 3367 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 104	substrate 3367 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
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
[Effect of balsalazide on intestinal mucosal permeability of dextran sulfate sodium-induced colitis in mice].	2009 Mar	19296261
Safety, efficacy, and pharmacokinetics of balsalazide in pediatric patients with mild-to-moderate active ulcerative colitis: results of a randomized, double-blind study.	2009 Nov	19633577
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 `Fri Dec 15 17:48:15 UTC 2023` Edited by `admin` on `Fri Dec 15 17:48:15 UTC 2023`
Record UNII	15ASW03C9S
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BALSALAZIDE DISODIUM ANHYDROUS

Common Name

English

Balsalazide sodium [WHO-DD]

Common Name

English

BALSALAZIDE DISODIUM SALT ANHYDROUS [MI]

Common Name

English

BENZOIC ACID, 5-((1E)-2-(4-(((2-CARBOXYETHYL)AMINO)CARBONYL)PHENYL)DIAZENYL)-2-HYDROXY-, SODIUM SALT (1:2)

Common Name

English

Code System Code Type Description

CAS

213594-60-6

Created by admin on Fri Dec 15 17:48:15 UTC 2023 , Edited by admin on Fri Dec 15 17:48:15 UTC 2023

PRIMARY

MERCK INDEX

m2208

Created by admin on Fri Dec 15 17:48:16 UTC 2023 , Edited by admin on Fri Dec 15 17:48:16 UTC 2023

PRIMARY

SMS_ID

100000128355

Created by admin on Fri Dec 15 17:48:16 UTC 2023 , Edited by admin on Fri Dec 15 17:48:16 UTC 2023

PRIMARY

FDA UNII

15ASW03C9S

Created by admin on Fri Dec 15 17:48:16 UTC 2023 , Edited by admin on Fri Dec 15 17:48:16 UTC 2023

PRIMARY

CAS

82101-18-6

Created by admin on Fri Dec 15 17:48:16 UTC 2023 , Edited by admin on Fri Dec 15 17:48:16 UTC 2023

NON-SPECIFIC STEREOCHEMISTRY

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					P80AL8J7ZP

BALSALAZIDE

ACTIVE MOIETY

Details

SMILES

InChI

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

Originator

Approval Year

Targets

Conditions

Approved Use

Launch Date

Cmax

AUC

Doses

AEs

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Sourcing

PubMed

Patents

Sample Use Guides

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

C_max

Drug as perpetrator