MESALAMINE HYDROCHLORIDE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C7H7NO3.ClH
Molecular Weight	189.596
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=KKRSNTURHSOKTM-UHFFFAOYSA-N

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

HIDE SMILES / InChI

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

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

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: 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
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
A 10-year survey of inflammatory bowel diseases-drug therapy, costs and adverse reactions.	2001 Apr	11284775
[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
The expression of IL-12 p40 and its homologue, Epstein-Barr virus-induced gene 3, in inflammatory bowel disease.	2001 Aug	11515847
Inflammatory pseudotumor of the liver as the first manifestation of Crohn's disease.	2001 Aug	11513216
Adult fibrosing colonopathy associated with mesalazine treatment.	2001 Aug	11513205
[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
Effects of chondroitin sulfate on colitis induced by dextran sulfate sodium in rats.	2001 Feb	11286397
[Hypersensitivity to mesalazine after severe allergic reaction to sulfasalazine].	2001 Jan	11300109
Acute renal failure in a 53-year-old woman with Crohn's disease treated with 5-aminosalicylic acid.	2001 Jul	11431204
Comparison of 5-amino salicylic acid plus glucocorticosteroid with metronidazole and ciprofloxacin in patients with active ulcerative colitis.	2001 Jul	11418802
Oral balsalazide (Colazal) for ulcerative colitis.	2001 Jul 23	11468602
Ulcerative colitis associated with interferon treatment for chronic hepatitis C.	2001 Jun	11451187
Azo-containing urethane analogues for colonic drug delivery: synthesis, characterization and in-vitro evaluation.	2001 Jun	11428667
Diversion colitis in children with colovaginoplasty.	2001 Jun	11412227
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
What can nephrologists learn from epidemiology?	2001 Mar-Apr	11411019
Impact of different therapeutic regimens on the outcome of patients with Crohn's disease of the upper gastrointestinal tract.	2001 May	11383598
Inflammatory bowel disease and pregnancy.	2001 May	11383588
Crohn's disease of the esophagus: clinical features and outcomes.	2001 May	11383583
Conventional treatment of Crohn's disease: objectives and outcomes.	2001 May	11380039
[Interstitial nephritis after treatment with mesalazine in the patient with ulcerative colitis].	2001 May 10	11460356
Review article: balsalazide therapy in ulcerative colitis.	2001 Oct	11563993
Recent advances in the treatment of the seronegative spondyloarthropathies.	2001 Oct	11564371
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
Mesalamine induces manganese superoxide dismutase in rat intestinal epithelial cell lines and in vivo.	2001 Oct	11557525
Acute pericarditis associated with 5-aminosalicylic acid (5-ASA) treatment for severe active ulcerative colitis.	2001 Sep	11579953
[Generalized pustulous psoriasis: A novel extraintestinal manifestation of Crohn's disease?].	2001 Sep	11558073
Review article: current therapeutic options for radiation proctopathy.	2001 Sep	11552895
NO-mesalamine protects colonic epithelial cells against apoptotic damage induced by proinflammatory cytokines.	2001 Sep	11518677
Drug points: Hypersensitivity reaction to balsalazide.	2001 Sep 1	11532843
[Conservative therapy of severe ulcerative colitis. More effective than internists believe!].	2001 Sep 13	11599291
5-Aminosalicylate stimulates phospholipase D activity in macrophages.	2001 Sep 28	11566448
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
Balsalazide: a novel 5-aminosalicylate prodrug for the treatment of active ulcerative colitis.	2009 Oct	19743890
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 `Mon Mar 31 19:54:04 GMT 2025` Edited by `admin` on `Mon Mar 31 19:54:04 GMT 2025`
Record UNII	LQ7CF8AVM8
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NSC-4978

Preferred Name

English

MESALAMINE HYDROCHLORIDE

Common Name

English

BENZOIC ACID, 5-AMINO-2-HYDROXY-, HYDROCHLORIDE

Systematic Name

English

5-AMINOSALICYLIC ACID HYDROCHLORIDE

Systematic Name

English

Code System Code Type Description

CAS

6291-36-7