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

SMILES

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

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	MOL RATIO 1 MOL RATIO (average)

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

Description

Mesalamine, also known as Mesalazine or 5-aminosalicylic acid (5-ASA), is an anti-inflammatory drug used to treat inflammation of the digestive tract (Crohn's disease) and mild to moderate ulcerative colitis. Mesalazine is a bowel-specific aminosalicylate drug that is metabolized in the gut and has its predominant actions there, thereby having fewer systemic side effects. As a derivative of salicylic acid, 5-ASA is also an antioxidant that traps free radicals, which are potentially damaging by-products of metabolism. Although the mechanism of action of mesalazine is not fully understood, it appears to be topical rather than systemic. Mucosal production of arachidonic acid metabolites, both through the cyclooxygenase pathways, i.e., prostanoids, and through the lipoxygenase pathways, i.e., leukotrienes and hydroxyeicosatetraenoic acids, is increased in patients with chronic inflammatory bowel disease, and it is possible that mesalazine diminishes inflammation by blocking cyclooxygenase and inhibiting prostaglandin production in the colon. Mesalazine is used for the treatment of active ulcerative proctitis.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
arachidonic acid metabolic process 6	Modulator 846
Cyclooxygenase-2 201	Inhibitor 8,504
Intermediate conductance calcium-activated potassium channel protein 4 13	Inhibitor 8,504	26.0 µM [EC50]
Nitric oxide synthase, inducible 55	Inhibitor 8,504
reactive oxygen species biosynthetic process 41	Inhibitor 8,504	0.69 µM [IC50]
apoptotic process 51	Inhibitor 8,504	16.0 µM [IC50]
macrophage chemotaxis 6	Inhibitor 8,504	0.24 mM [IC50]
Cyclooxygenase-1 131	Inhibitor 8,504
Arachidonate 5-lipoxygenase 52	Inhibitor 8,504
Peroxisome proliferator-activated receptor gamma 118	Agonist 2,752

Conditions

Condition	Modality	Targets	Highest Phase	Product
Ulcerative colitis 125	Primary		Approved 8,583	COLAZAL
Ulcerative colitis 125	Primary		Approved 8,583	PENTASA

C_max

Value	Dose	Analyte	Population
857 ng/mL	1.2 g single, oral	MESALAMINE plasma	Homo sapiens
1595 ng/mL	2.4 g single, oral	MESALAMINE plasma	Homo sapiens
2154 ng/mL	4.8 g single, oral	MESALAMINE plasma	Homo sapiens
150 ng/mL	800 mg single, oral	MESALAMINE plasma	Homo sapiens
452 ng/mL	6.75 mg 1 times / day multiple, oral	BALSALAZIDE plasma	Homo sapiens
344 ng/mL	6.25 mg 1 times / day multiple, oral	MESALAMINE plasma	Homo sapiens

AUC

Value	Dose	Analyte	Population
9578 ng × h/mL	1.2 g single, oral	MESALAMINE plasma	Homo sapiens
21084 ng × h/mL	2.4 g single, oral	MESALAMINE plasma	Homo sapiens
44775 ng × h/mL	4.8 g single, oral	MESALAMINE plasma	Homo sapiens
909 ng × h/mL	800 mg single, oral	MESALAMINE plasma	Homo sapiens
2031 ng × h/mL	6.75 mg 1 times / day multiple, oral	BALSALAZIDE plasma	Homo sapiens
1931 ng × h/mL	6.25 mg 1 times / day multiple, oral	MESALAMINE plasma	Homo sapiens

T_1/2

Value	Dose	Analyte	Population
8.56 h	1.2 g single, oral	MESALAMINE plasma	Homo sapiens
7.05 h	2.4 g single, oral	MESALAMINE plasma	Homo sapiens
7.25 h	4.8 g single, oral	MESALAMINE plasma	Homo sapiens
25 h	800 mg single, oral	MESALAMINE plasma	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
57%	1.2 g single, oral		MESALAMINE plasma	Homo sapiens

Doses

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Dose	Population	Adverse events
6.75 g 1 times / day multiple, oral	unhealthy, 12.8 years (range: 5-17 years)	Disc. AE: Abdominal pain, Urticaria...
6.6 g 1 times / day multiple, oral Recommended	unhealthy, adult	Disc. AE: Colitis ulcerative, Nausea...

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AEs

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AE	Significance	Dose	Population
Abdominal pain	1 patient Disc. AE	6.75 g 1 times / day multiple, oral	unhealthy, 12.8 years (range: 5-17 years)
Urticaria	1 patient Disc. AE	6.75 g 1 times / day multiple, oral	unhealthy, 12.8 years (range: 5-17 years)
Erythema nodosum	1% Disc. AE	6.6 g 1 times / day multiple, oral Recommended	unhealthy, adult
Frequent bowel movements	1% Disc. AE	6.6 g 1 times / day multiple, oral Recommended	unhealthy, adult
Vomiting	1% Disc. AE	6.6 g 1 times / day multiple, oral Recommended	unhealthy, adult

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2,252 substrate 1,946 inducer 1,087	inhibitor 2,438 inducer 440	inhibitor 2,507 substrate 1,388

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 2,153 CYP2C19 2,057 CYP3A4/5 296 CYP2A6 879 CYP2E1 1,060 UGT1A6 136 UGT1A9 148 OATP1A2 43 OATP1B1 1,079 OATP1B3 961 OATP2B1 157 BSEP 550 MRP2 499 BCRP 910	OATP2B1 122 OATP1B1 503 OATP1B3 435	CYP2B6 669 CYP1A2 832

Drug as perpetrator

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Target	Modality	Activity	Metabolite
CYP2A6 911	inhibitor 4,027	no [IC50 >10 uM]
CYP2E1 1,146	inhibitor 4,027	no [IC50 >10 uM]
BCRP 985	inhibitor 4,027	no	5-ASA 6
CYP1A2 2,333	inducer 1,966	no
CYP1A2 2,333	inhibitor 4,027	no

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Drug as victim

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Target	Modality	Activity	Metabolite
OATP2B1 122	substrate 4,014	yes [Km 188.9 uM]	5-ASA 6
OATP1B1 503	substrate 4,014	yes [Km 55.1 uM]	5-ASA 6
OATP1B3 435	substrate 4,014	yes [Km 77.4 uM]	5-ASA 6
CYP2D6 1,388	substrate 4,014	yes
CYP3A4 1,946	substrate 4,014	yes

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
ChEBI	CHEBI:6775	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:6775
ChemicalBook	CB1480481	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB1480481
eMolecules	477209	https://www.emolecules.com/cgi-bin/more?vid=477209
MolPort	MolPort-001-641-024	https://www.molport.com/shop/molecule-link/MolPort-001-641-024
Selleck Chemicals	Mesalamine(Lialda)	http://www.selleckchem.com/products/Mesalamine(Lialda).html

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PubMed

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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
Is it Crohn's disease? A severe systemic granulomatous reaction to sulfasalazine in patient with rheumatoid arthritis.	2001	11570976
TNF-alpha induced endothelial MAdCAM-1 expression is regulated by exogenous, not endogenous nitric oxide.	2001	11481030
Tolerability of aminosalicylates in inflammatory bowel disease.	2001	11437696
[The new experimental ulcerative colitis model in rats induced by subserosal injection of acetic acid].	2001 Aug	11530682

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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.