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)C(=C1)C(O)=O

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

Description
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/020610s014lbl.pdfhttp://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
arachidonic acid metabolic process 6 Target ID: GO:0019369 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/020610s014lbl.pdf	Modulator 846
Cyclooxygenase-2 201 Target ID: CHEMBL230 Sources: http://www.drugbank.ca/drugs/DB00244	Inhibitor 8504
Intermediate conductance calcium-activated potassium channel protein 4 13 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 8504	26.0 µM [EC50]
Nitric oxide synthase, inducible 55 Target ID: CHEMBL4481 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10493988	Inhibitor 8504
reactive oxygen species biosynthetic process 41 Target ID: GO:1903409 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9893931	Inhibitor 8504	0.69 µM [IC50]
apoptotic process 51 Target ID: GO:0006915 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9352850	Inhibitor 8504	16.0 µM [IC50]
macrophage chemotaxis 6 Target ID: GO:0048246 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2908754	Inhibitor 8504	0.24 mM [IC50]
Cyclooxygenase-1 131 Target ID: CHEMBL221 Sources: http://www.drugbank.ca/drugs/DB00244	Inhibitor 8504
Arachidonate 5-lipoxygenase 52 Target ID: CHEMBL215 Sources: http://www.drugbank.ca/drugs/DB00244	Inhibitor 8504
Peroxisome proliferator-activated receptor gamma 118 Target ID: CHEMBL235 Sources: http://www.drugbank.ca/drugs/DB00244	Agonist 2752

Conditions

Condition	Modality	Targets	Highest Phase	Product
Ulcerative colitis 125 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/020610s014lbl.pdf	Primary		Approved 8583	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 2000
Ulcerative colitis 125 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020049s027lbl.pdf	Primary		Approved 8583	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
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
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
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
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
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

AUC

Value	Dose	Analyte	Population
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
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
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
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
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

T_1/2

Value	Dose	Analyte	Population
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
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
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

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
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) Health Status: unhealthy Age Group: 12.8 years (range: 5-17 years) Sex: M+F 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	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/022205Orig1s000MedR.pdf	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

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) Health Status: unhealthy Age Group: 12.8 years (range: 5-17 years) Sex: M+F 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) Health Status: unhealthy Age Group: 12.8 years (range: 5-17 years) Sex: M+F 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	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/022205Orig1s000MedR.pdf
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	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/022205Orig1s000MedR.pdf
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	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/022205Orig1s000MedR.pdf
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	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/022205Orig1s000MedR.pdf
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	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/022205Orig1s000MedR.pdf

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252 substrate 1946 inducer 1087	inhibitor 2438 inducer 440	inhibitor 2507 substrate 1388

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 2153 CYP2C19 2057 CYP3A4/5 296 CYP2A6 879 CYP2E1 1060 UGT1A6 136 UGT1A9 148 OATP1A2 43 OATP1B1 1079 OATP1B3 961 OATP2B1 157 BSEP 550 MRP2 499 BCRP 910	OATP2B1 122 OATP1B1 503 OATP1B3 435	CYP2B6 669 CYP1A2 832

Drug as perpetrator

Target	Modality	Activity	Metabolite
CYP2A6 911	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw1MjgyIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDEyMDEzNDYifX0%3D	no [IC50 >10 uM]
CYP2E1 1146	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw1MjgxIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDEyMDEzNDYifX0%3D	no [IC50 >10 uM]
BCRP 985	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/19421845/	no	5-ASA 6
CYP1A2 2333	inducer 1966 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4556210/	no
CYP1A2 2333	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/020610s023lbl.pdf#page=11 Page: 11.0	no
CYP1A2 2333	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/020610s023lbl.pdf#page=11 Page: 11.0	no	5-ASA 6
CYP2C19 2141	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/020610s023lbl.pdf#page=11 Page: 11.0	no
CYP2C19 2141	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/020610s023lbl.pdf#page=11 Page: 11.0	no	5-ASA 6
CYP2C9 2497	inducer 1966 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4556210/	no
CYP2C9 2497	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/020610s023lbl.pdf#page=11 Page: 11.0	no
CYP2C9 2497	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/020610s023lbl.pdf#page=11 Page: 11.0	no	5-ASA 6
CYP2D6 2546	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/020610s023lbl.pdf#page=11 Page: 11.0	no
CYP2D6 2546	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/020610s023lbl.pdf#page=11 Page: 11.0	no	5-ASA 6
CYP3A4/5 357	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/020610s023lbl.pdf#page=11 Page: 11.0	no
CYP3A4/5 357	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/020610s023lbl.pdf#page=11 Page: 11.0	no	5-ASA 6
MRP2 625	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/18457386/	no	5-ASA 6
OATP1A2 43	inhibitor 4027 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 6
OATP2B1 162	inhibitor 4027 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 6
UGT1A6 171	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNzQzMzE2IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDcwNCJ9fQ%3D%3D	no	5-ASA 6
UGT1A9 155	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNzQzMzE2IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDcwNCJ9fQ%3D%3D	no	5-ASA 6
CYP1A2 2333	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/022301lbl.pdf#page=5 Page: 5.0	unlikely
CYP2C19 2141	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/022301lbl.pdf#page=5 Page: 5.0	unlikely
CYP2C9 2497	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/022301lbl.pdf#page=5 Page: 5.0	unlikely
CYP2D6 2546	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/022301lbl.pdf#page=5 Page: 5.0	unlikely
CYP3A4 2633	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/022301lbl.pdf#page=5 Page: 5.0	unlikely
BSEP 554	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/22961681/	weak [IC50 381.4 uM]	5-ASA 6
CYP2B6 1160	inducer 1966 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4556210/	yes
CYP3A4 2633	inducer 1966 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4556210/	yes
OATP1B1 1095	inhibitor 4027 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 6
OATP1B3 970	inhibitor 4027 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 6

Drug as victim

Target	Modality	Activity	Metabolite
OATP2B1 122	substrate 4014 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 6
OATP1B1 503	substrate 4014 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 6
OATP1B3 435	substrate 4014 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 6
CYP2D6 1388	substrate 4014 Sources: https://ideas.repec.org/a/aad/iseicj/v7y2019i0p753-759.html	yes
CYP3A4 1946	substrate 4014 Sources: https://ideas.repec.org/a/aad/iseicj/v7y2019i0p753-759.html	yes
OATP2B1 122	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/32189541/	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
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
ZINC	ZINC000000001688	http://zinc15.docking.org/substances/ZINC000000001688
ChEBI	CHEBI:267413	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:267413
ChemicalBook	CB9148828	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB9148828
eMolecules	18597217	https://www.emolecules.com/cgi-bin/more?vid=18597217
MolPort	MolPort-005-934-178	https://www.molport.com/shop/molecule-link/MolPort-005-934-178
ZINC	ZINC000003952881	http://zinc15.docking.org/substances/ZINC000003952881

PubMed

Title	Date	PubMed
Mesalazine activation of eosinophil.	1997 Oct 11	10213581
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
Interstitial nephritis in children with Crohn's disease.	2000 Apr	10791141
Effects of sulfasalazine and its metabolites on steady state messenger RNA concentrations for inflammatory cytokines, matrix metalloproteinases, and tissue inhibitors of metalloproteinase in rheumatoid synovial fibroblasts.	2000 Mar	10743803
Mesalamine-induced chest pain: a case report.	2000 May	10833545
Glomerular and tubular renal functions after long-term medication of sulphasalazine, olsalazine, and mesalazine in patients with ulcerative colitis.	2000 Nov	11149559
[Early renal failure caused by mesalazine].	2000 Oct	11344635
Pyelonephritis caused by mesalazine.	2000 Oct	11015014
Tolerability of aminosalicylates in inflammatory bowel disease.	2001	11437696
[Hepatotoxicity of medications].	2001 Apr 14	11360729
Sulphasalazine inhibits macrophage activation: inhibitory effects on inducible nitric oxide synthase expression, interleukin-12 production and major histocompatibility complex II expression.	2001 Aug	11529938
Oral versus combination mesalazine therapy in active ulcerative colitis: a double-blind, double-dummy, randomized multicentre study.	2001 Feb	11148445
A novel pH- and time-based multi-unit potential colonic drug delivery system. II. Optimization of multiple response variables.	2001 Feb 1	11165097
A novel pH- and time-based multi-unit potential colonic drug delivery system. I. Development.	2001 Feb 1	11165096
5-Aminosalicylic acid protection against oxidative damage to synaptosomal membranes by alkoxyl radicals in vitro.	2001 Jan	11358278
[Therapy of active Crohn disease with Boswellia serrata extract H 15].	2001 Jan	11215357
Can postoperative relapse of Crohn's disease be prevented?	2001 Jan	11197264
Once versus divided daily dosing with delayed-release mesalazine: a study of tissue drug concentrations and standard pharmacokinetic parameters.	2001 Jan	11136278
Clinical onset of the Crohn's disease after eradication therapy of Helicobacter pylori infection. Does Helicobacter pylori infection interact with natural history of inflammatory bowel diseases?	2001 Jan-Feb	11208510
Recurrent atypical myxoid fibroepithelial polyp associated with vulvar Crohn's disease.	2001 Jul	11444204
[A case of successful mesalazine enema for rectal cavitating ulcer of Crohn's disease].	2001 Jun	11436282
Lacrimal gland inflammation as the presenting sign of Crohn's disease.	2001 Jun	11428531
Probiotics (Br J Surg 2001; 88: 161-2).	2001 Jun	11412272
5-Aminosalicylates in inflammatory bowel disease: choosing the right dose.	2001 Jun-Jul	11529648
T-large granular lymphocyte leukemia accompanied by an increase of natural killer cells (CD3-) and associated with ulcerative colitis and autoimmune hepatitis.	2001 Mar	11342376
Lymph folliculitis in ulcerative colitis.	2001 Mar	11305524
Anti-tumor necrosis factor monoclonal antibody therapy for gastrointestinal Behçet's disease: a case report.	2001 Mar	11231954
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
Inflammatory bowel disease and pregnancy.	2001 May	11383588
Familial microscopic colitis.	2001 May	11381303
Conventional treatment of Crohn's disease: objectives and outcomes.	2001 May	11380039
A new 5-aminosalicylic acid multi-unit dosage form for the therapy of ulcerative colitis.	2001 May	11343881
Determination of 5-aminosalicylic acid related impurities by micellar electrokinetic chromatography with an ion-pair reagent.	2001 May 4	11382289
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
Sulfasalazine, a potent suppressor of lymphoma growth by inhibition of the x(c)- cystine transporter: a new action for an old drug.	2001 Oct	11587223
[Conservative therapy of severe ulcerative colitis. More effective than internists believe!].	2001 Sep 13	11599291
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

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.

Name

Type

Language

MESALAZINE

Preferred Name

English

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

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