MESALAMINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C7H7NO3
Molecular Weight	153.1354
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NC1=CC(C(O)=O)=C(O)C=C1

InChI

InChIKey=KBOPZPXVLCULAV-UHFFFAOYSA-N

InChI=1S/C7H7NO3/c8-4-1-2-6(9)5(3-4)7(10)11/h1-3,9H,8H2,(H,10,11)

HIDE SMILES / InChI

Molecular Formula	C7H7NO3
Molecular Weight	153.1354
Charge	0
Count

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

Description
Sources: http://www.drugbank.ca/drugs/DB00244
Curator's Comment: Description was created based on several sources, including https://www.drugs.com/mtm/mesalamine.html

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
Cyclooxygenase-2 196 Target ID: CHEMBL230 Sources: http://www.drugbank.ca/drugs/DB00244	Inhibitor 8297
Intermediate conductance calcium-activated potassium channel protein 4 10 Target ID: O89109 Gene ID: 16534.0 Gene Symbol: Kcnn4 Target Organism: Mus musculus (Mouse) Sources: https://www.ncbi.nlm.nih.gov/pubmed/23516517	Inhibitor 8297	26.0 µM [EC50]
Nitric oxide synthase, inducible 50 Target ID: CHEMBL4481 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10493988	Inhibitor 8297
reactive oxygen species biosynthetic process 37 Target ID: GO:1903409 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9893931	Inhibitor 8297	0.69 µM [IC50]
apoptotic process 48 Target ID: GO:0006915 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9352850	Inhibitor 8297	16.0 µM [IC50]
macrophage chemotaxis 3 Target ID: GO:0048246 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2908754	Inhibitor 8297	0.24 mM [IC50]
Cyclooxygenase-1 127 Target ID: CHEMBL221 Sources: http://www.drugbank.ca/drugs/DB00244	Inhibitor 8297
Arachidonate 5-lipoxygenase 49 Target ID: CHEMBL215 Sources: http://www.drugbank.ca/drugs/DB00244	Inhibitor 8297
Peroxisome proliferator-activated receptor gamma 111 Target ID: CHEMBL235 Sources: http://www.drugbank.ca/drugs/DB00244	Agonist 2678

Conditions

Condition	Modality	Targets	Highest Phase	Product
Ulcerative colitis 123 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020049s027lbl.pdf	Primary		Approved 8429	PENTASA Approved Use PENTASA is indicated for the induction of remission and for the treatment of patients with mildly to moderately active ulcerative colitis. Launch Date 1993

C_max

Value	Dose	Analyte	Population
150 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/204412s006lbl.pdf	800 mg single, oral dose: 800 mg route of administration: Oral experiment type: SINGLE co-administered:	MESALAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED
1595 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/022000lbl.pdf	2.4 g single, oral dose: 2.4 g route of administration: Oral experiment type: SINGLE co-administered:	MESALAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED
2154 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/022000lbl.pdf	4.8 g single, oral dose: 4.8 g route of administration: Oral experiment type: SINGLE co-administered:	MESALAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED
857 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/022000lbl.pdf	1.2 g single, oral dose: 1.2 g route of administration: Oral experiment type: SINGLE co-administered:	MESALAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED

AUC

Value	Dose	Analyte	Population
909 ng × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/204412s006lbl.pdf	800 mg single, oral dose: 800 mg route of administration: Oral experiment type: SINGLE co-administered:	MESALAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED
21084 ng × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/022000lbl.pdf	2.4 g single, oral dose: 2.4 g route of administration: Oral experiment type: SINGLE co-administered:	MESALAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED
44775 ng × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/022000lbl.pdf	4.8 g single, oral dose: 4.8 g route of administration: Oral experiment type: SINGLE co-administered:	MESALAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED
9578 ng × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/022000lbl.pdf	1.2 g single, oral dose: 1.2 g route of administration: Oral experiment type: SINGLE co-administered:	MESALAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED

T_1/2

Value	Dose	Analyte	Population
25 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/204412s006lbl.pdf	800 mg single, oral dose: 800 mg route of administration: Oral experiment type: SINGLE co-administered:	MESALAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED
7.05 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/022000lbl.pdf	2.4 g single, oral dose: 2.4 g route of administration: Oral experiment type: SINGLE co-administered:	MESALAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED
7.25 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/022000lbl.pdf	4.8 g single, oral dose: 4.8 g route of administration: Oral experiment type: SINGLE co-administered:	MESALAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED
8.56 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/022000lbl.pdf	1.2 g single, oral dose: 1.2 g route of administration: Oral experiment type: SINGLE co-administered:	MESALAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED

F_unbound

Value	Dose	Co-administered	Analyte	Population
57% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/022000lbl.pdf	1.2 g single, oral dose: 1.2 g route of administration: Oral experiment type: SINGLE co-administered:		MESALAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED

Doses

Dose	Population	Adverse events
14.5 g single, oral\|rectal (complex) Overdose Dose: 14.5 g Route: oral\|rectal Route: single Dose: 14.5 g Sources: https://pubmed.ncbi.nlm.nih.gov/20670990/	unhealthy, 20 - years n = 1 Health Status: unhealthy Condition: ulcerative colitis Age Group: 20 - years Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/20670990/	Disc. AE: Intoxication... AEs leading to discontinuation/dose reduction: Intoxication (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/20670990/
4.8 g 1 times / day steady, oral Recommended Dose: 4.8 g, 1 times / day Route: oral Route: steady Dose: 4.8 g, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/30431332/	unhealthy, 28 - 41 years n = 10 Health Status: unhealthy Condition: Inflammatory bowel disease, breastfeeding mothers Age Group: 28 - 41 years Sex: F Population Size: 10 Sources: https://pubmed.ncbi.nlm.nih.gov/30431332/	Sources: https://pubmed.ncbi.nlm.nih.gov/30431332/
15.7 mg/kg 1 times / day steady, oral (mother), breasteeding (infant) (mean) Dose: 15.7 mg/kg, 1 times / day Route: oral (mother), breasteeding (infant) Route: steady Dose: 15.7 mg/kg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/30431332/	healthy, 35–251 days n = 10 Health Status: healthy Age Group: 35–251 days Sex: M+F Population Size: 10 Sources: https://pubmed.ncbi.nlm.nih.gov/30431332/	Sources: https://pubmed.ncbi.nlm.nih.gov/30431332/
3.2 g 1 times / day steady, oral Recommended Dose: 3.2 g, 1 times / day Route: oral Route: steady Dose: 3.2 g, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/20441247/	unhealthy, 42 years n = 1 Health Status: unhealthy Condition: ulcerative colitis Age Group: 42 years Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/20441247/	Disc. AE: Hypersensitivity... AEs leading to discontinuation/dose reduction: Hypersensitivity (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/20441247/
1.6 g 1 times / day steady, oral (median) Recommended Dose: 1.6 g, 1 times / day Route: oral Route: steady Dose: 1.6 g, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/019651s023lbl.pdf	unhealthy, adult n = 155 Health Status: unhealthy Condition: ulcerative colitis Age Group: adult Sex: unknown Population Size: 155 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/019651s023lbl.pdf	Disc. AE: Anxiety, Headache... AEs leading to discontinuation/dose reduction: Anxiety (1 patient) Headache (1 patient) Pruritus (1 patient) Libido decreased (1 patient) Rheumatoid arthritis (1 patient) Asthenia (1 patient) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/019651s023lbl.pdf
4.8 g 1 times / day steady, oral Recommended Dose: 4.8 g, 1 times / day Route: oral Route: steady Dose: 4.8 g, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/019651s023lbl.pdf	unhealthy, adult n = 155 Health Status: unhealthy Condition: ulcerative colitis Age Group: adult Sex: unknown Population Size: 155 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/019651s023lbl.pdf	Disc. AE: Diarrhea, Colitis... AEs leading to discontinuation/dose reduction: Diarrhea (1 patient) Colitis (1 patient) Dizziness (1 patient) Nausea (1 patient) Joint pain (1 patient) Headache (2 patients) Rash (1 patient) Lethargy (1 patient) Constipation (1 patient) Dry mouth (1 patient) Malaise (1 patient) Back discomfort (1 patient) Disorientation (1 patient) Indigestion (1 patient) Nausea (1 patient) Generalised aching (1 patient) Vomiting (1 patient) Muscle cramps (1 patient) Nasal congestion (1 patient) Eustachian tube obstruction (1 patient) Fever (1 patient) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/019651s023lbl.pdf

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 1587 substrate 1737 inducer 781	inhibitor 1767 inducer 389	inhibitor 1852 substrate 1217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1524 CYP2C19 1478		CYP2B6 547 CYP1A2 701

Drug as perpetrator

Target	Modality	Activity
CYP1A2 1692	inducer 1573 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4556210/	no
CYP2C9 1819	inducer 1573 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4556210/	no
CYP1A2 1692	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/022301lbl.pdf#page=5 Page: 5.0	unlikely
CYP2C19 1553	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/022301lbl.pdf#page=5 Page: 5.0	unlikely
CYP2C9 1819	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/022301lbl.pdf#page=5 Page: 5.0	unlikely
CYP2D6 1891	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/022301lbl.pdf#page=5 Page: 5.0	unlikely
CYP3A4 1925	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/022301lbl.pdf#page=5 Page: 5.0	unlikely
CYP2B6 1001	inducer 1573 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4556210/	yes
CYP3A4 1925	inducer 1573 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4556210/	yes

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP2D6 1217	substrate 3367 Sources: https://ideas.repec.org/a/aad/iseicj/v7y2019i0p753-759.html	yes
CYP3A4 1737	substrate 3367 Sources: https://ideas.repec.org/a/aad/iseicj/v7y2019i0p753-759.html	yes

Sourcing

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
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
ZINC	ZINC000000001688	http://zinc15.docking.org/substances/ZINC000000001688
eMolecules	477209	https://www.emolecules.com/cgi-bin/more?vid=477209

PubMed

Title	Date	PubMed
A 10-year survey of inflammatory bowel diseases-drug therapy, costs and adverse reactions.	2001 Apr	11284775
Intestinal luminal pH in inflammatory bowel disease: possible determinants and implications for therapy with aminosalicylates and other drugs.	2001 Apr	11247905
[Hepatotoxicity of medications].	2001 Apr 14	11360729
[The new experimental ulcerative colitis model in rats induced by subserosal injection of acetic acid].	2001 Aug	11530682
Sulphasalazine inhibits macrophage activation: inhibitory effects on inducible nitric oxide synthase expression, interleukin-12 production and major histocompatibility complex II expression.	2001 Aug	11529938
Mesalazine 4 g daily given as prolonged-release granules twice daily and four times daily is at least as effective as prolonged-release tablets four times daily in patients with ulcerative colitis.	2001 Aug	11515850
Measurement of colonic mucosal concentrations of 5-aminosalicylic acid is useful for estimating its therapeutic efficacy in distal ulcerative colitis: comparison of orally administered mesalamine and sulfasalazine.	2001 Aug	11515848
Inflammatory pseudotumor of the liver as the first manifestation of Crohn's disease.	2001 Aug	11513216
[Metastatic Crohn's disease in childhood].	2001 Aug	11472671
Glucocorticoids and IL-10, but not 6-MP, 5-ASA or sulfasalazine block endothelial expression of MAdCAM-1: implications for inflammatory bowel disease therapy.	2001 Aug	11472325
Renal tubular injury is present in acute inflammatory bowel disease prior to the introduction of drug therapy.	2001 Aug	11472315
Novel azo derivatives as prodrugs of 5-aminosalicylic acid and amino derivatives with potent platelet activating factor antagonist activity.	2001 Aug 30	11520209
Inflammatory bowel disease.	2001 Feb	11272216
Mesalamine maintenance therapy for Crohn's disease.	2001 Feb	11271451
[Ulcerative esophagitis and colitis as rare manifestations of Adamantiades-Behcet disease].	2001 Feb	11253508
Look out for toxic effects of mesalamines!	2001 Feb	11205663
[Hypersensitivity to mesalazine after severe allergic reaction to sulfasalazine].	2001 Jan	11300109
Can postoperative relapse of Crohn's disease be prevented?	2001 Jan	11197264
On using the standard gamble to determine utilities for uncertain health states.	2001 Jan-Feb	11206955
Oral balsalazide (Colazal) for ulcerative colitis.	2001 Jul 23	11468602
Diversion colitis in children with colovaginoplasty.	2001 Jun	11412227
5-Aminosalicylates in inflammatory bowel disease: choosing the right dose.	2001 Jun-Jul	11529648
Treatment responses in collagenous colitis.	2001 Mar	11280557
Minimal renal dysfunction in inflammatory bowel disease is related to disease activity but not to 5-ASA use.	2001 Mar	11207511
From the Food and Drug Administration.	2001 Mar 7	11231734
What can nephrologists learn from epidemiology?	2001 Mar-Apr	11411019
Conventional treatment of Crohn's disease: objectives and outcomes.	2001 May	11380039
Salvage external beam radiotherapy for clinical failure after cryosurgery for prostate cancer.	2001 Nov 1	11597801
Review article: balsalazide therapy in ulcerative colitis.	2001 Oct	11563993
Olsalazine is not superior to placebo in maintaining remission of inactive Crohn's colitis and ileocolitis: a double blind, parallel, randomised, multicentre study.	2001 Oct	11559654
[Collagenous colitis. A study of 11 cases].	2001 Sep	11593141
[Conservative therapy of severe ulcerative colitis. More effective than internists believe!].	2001 Sep 13	11599291
Guided self-management and patient-directed follow-up of ulcerative colitis: a randomised trial.	2001 Sep 22	11583752

Patents

Sample Use Guides

In Vivo Use Guide

Usual Adult Dose for Ulcerative Colitis - Active ORAL: 250 and 500 mg capsules: 1 g orally 4 times a day Duration of therapy: Up to 8 weeks 400 mg tablets: 800 mg orally 3 times a day Duration of therapy: 6 weeks 400 mg delayed release capsules: 800 mg orally 3 times a day Duration of therapy: 6 weeks 800 mg delayed release tablets: 1600 mg orally 3 times a day Duration of therapy: 6 weeks 1200 mg tablets: 2.4 to 4.8 g orally once a day with food

Route of Administration: Oral

In Vitro Use Guide

Treatment of both HT-29 wild-type, dominant-negative PPARg and empty vector cells HT-29 cells with Mesalamine (30 mM) for 48 h increased the activity of PPARg

Substance Class	Chemical Created by `admin` on `Sat Dec 16 17:31:32 GMT 2023` Edited by `admin` on `Sat Dec 16 17:31:32 GMT 2023`
Record UNII	4Q81I59GXC
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

MESALAMINE

Official Name

English

MESALAMINE [VANDF]

Common Name

English

MESALAMINE [HSDB]

Common Name

English

MESALAZINE [EP MONOGRAPH]

Common Name

English

mesalazine [INN]

Common Name

English

MESALAMINE [USP MONOGRAPH]

Common Name

English

FISALAMINE

Common Name

English

ASACOL

Brand Name

English

MESALAZINE [JAN]

Common Name

English

ROWASA

Brand Name

English

MESALAMINE [MI]

Common Name

English

Mesalazine [WHO-DD]

Common Name

English

5-Aminosalicylic acid

Systematic Name

English

APRISO

Brand Name

English

NSC-38877

Code

English

5-AMINO-2-HYDROXYBENZOIC ACID

Systematic Name

English

BENZOIC ACID, 5-AMINO-2-HYDROXY-

Common Name

English

MESALAZINE [EP IMPURITY]

Common Name

English

PENTASA

Brand Name

English

MESALAZINE [MART.]

Common Name

English

SFROWASA

Brand Name

English

MESALAMINE [USAN]

Common Name

English

LIALDA

Brand Name

English

MAX-002

Code

English

MESALAZINE

Official Name

English

MESALAMINE [ORANGE BOOK]

Common Name

English

MESALAMINE [USP-RS]

Common Name

English

CANASA

Brand Name

English

IIALDA

Brand Name

English

M-AMINOSALICYLIC ACID

Systematic Name

English

Classification Tree Code System Code

WHO-VATC

QA07EC02