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mesalazine 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definition	Drug id	CAS RN
phenylazosalicylic acid derivatives antibacterial	1710	89-57-6

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: 5-ASA mesalamine 2-Hydroxy-5-aminobenzoic acid 3-Carboxy-4-hydroxyaniline 5-Amino-2-hydroxybenzoic acid 5-Aminosalicylic acid claversal mesacol mesalazine mesalsal mesasal m-Aminosalicylic acid mesalamine hydrochloride mesalamine HCl	An anti-inflammatory agent, structurally related to the SALICYLATES, which is active in INFLAMMATORY BOWEL DISEASE. It is considered to be the active moiety of SULPHASALAZINE. (From Martindale, The Extra Pharmacopoeia, 30th ed) Molecular weight: 153.14 Formula: C7H7NO3 CLOGP: 1.06 LIPINSKI: 0 HAC: 4 HDO: 3 TPSA: 83.55 ALOGS: -1.10 ROTB: 1 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

5-ASA
mesalamine
2-Hydroxy-5-aminobenzoic acid
3-Carboxy-4-hydroxyaniline
5-Amino-2-hydroxybenzoic acid
5-Aminosalicylic acid
claversal
mesacol
mesalazine
mesalsal
mesasal
m-Aminosalicylic acid
mesalamine hydrochloride
mesalamine HCl

An anti-inflammatory agent, structurally related to the SALICYLATES, which is active in INFLAMMATORY BOWEL DISEASE. It is considered to be the active moiety of SULPHASALAZINE. (From Martindale, The Extra Pharmacopoeia, 30th ed)

Molecular weight: 153.14
Formula: C7H7NO3
CLOGP: 1.06
LIPINSKI: 0
HAC: 4
HDO: 3
TPSA: 83.55
ALOGS: -1.10
ROTB: 1

Status: OFP

Legend:
OFP - off patent
OFM - off market
ONP - on patent

Drug dosage:

Dose	Unit	Route
1.50	g	O
1.50	g	R

ADMET properties:

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Property	Value	Reference
CL (Clearance)	9.30 mL/min/kg	Lombardo F, Berellini G, Obach RS
EoM (Fraction excreted unchanged in urine)	7 %	Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose)	447.77 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BDDCS (Biopharmaceutical Drug Disposition Classification System)	2	Benet LZ, Broccatelli F, Oprea TI
S (Water solubility)	0.84 mg/mL	Bocci G, Oprea TI, Benet LZ
t_half (Half-life)	0.61 hours	Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma)	0.39 %	Lombardo F, Berellini G, Obach RS
Vd (Volume of distribution)	0.33 L/kg	Lombardo F, Berellini G, Obach RS

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Approvals:

Date	Agency	Company	Orphan
Dec. 24, 1987	FDA	MEDA PHARMS

FDA Adverse Event Reporting System (Female)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Colitis ulcerative	2650.88	10.71	1041	74686	25050	63388245
Haematochezia	1157.05	10.71	747	74980	52797	63360498
Frequent bowel movements	927.87	10.71	482	75245	22540	63390755
Off label use	918.53	10.71	2284	73443	672178	62741117
Condition aggravated	504.56	10.71	1324	74403	400893	63012402
Rectal haemorrhage	459.51	10.71	416	75311	48614	63364681
Macular degeneration	446.18	10.71	307	75420	24069	63389226
Inappropriate schedule of product administration	415.60	10.71	564	75163	103401	63309894
Faecal calprotectin increased	375.34	10.71	142	75585	3061	63410234
Abdominal pain	369.25	10.71	968	74759	292488	63120807

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FDA Adverse Event Reporting System (Male)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Colitis ulcerative	2432.52	12.46	918	51394	15602	34889017
Off label use	986.15	12.46	2019	50293	417505	34487114
Frequent bowel movements	944.65	12.46	435	51877	12352	34892267
Haematochezia	919.97	12.46	670	51642	45864	34858755
Condition aggravated	647.98	12.46	1084	51228	191112	34713507
Inappropriate schedule of product administration	546.58	12.46	564	51748	61732	34842887
Intentional product use issue	440.91	12.46	494	51818	59322	34845297
Colitis	440.57	12.46	400	51912	37350	34867269
Blood pressure fluctuation	293.37	12.46	267	52045	24982	34879637
Product use issue	291.25	12.46	413	51899	62803	34841816

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FDA Adverse Event Reporting System (Geriatric)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Colitis ulcerative	4168.22	10.70	1618	106130	33124	79603516
Off label use	2012.43	10.70	4016	103732	903199	78733441
Haematochezia	1775.36	10.70	1231	106517	86414	79550226
Frequent bowel movements	1460.04	10.70	739	107009	28800	79607840
Condition aggravated	1081.64	10.70	2201	105547	498923	79137717
Inappropriate schedule of product administration	964.98	10.70	1040	106708	132588	79504052
Intentional product use issue	727.88	10.70	960	106788	151152	79485488
Faecal calprotectin increased	575.75	10.70	233	107515	5308	79631332
Rectal haemorrhage	503.67	10.70	567	107181	75733	79560907
Abdominal pain	440.64	10.70	1339	106409	388230	79248410

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FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

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Source	Code	Description
ATC	A07EC02	ALIMENTARY TRACT AND METABOLISM ANTIDIARRHEALS, INTESTINAL ANTIINFLAMMATORY/ANTIINFECTIVE AGENTS INTESTINAL ANTIINFLAMMATORY AGENTS Aminosalicylic acid and similar agents
CHEBI has role	CHEBI:35475	non-steroidal anti-inflammatory agent
FDA CS	M0000971	Aminosalicylic Acids
FDA EPC	N0000175781	Aminosalicylate
MeSH PA	D000700	Analgesics
MeSH PA	D018712	Analgesics, Non-Narcotic
MeSH PA	D000893	Anti-Inflammatory Agents
MeSH PA	D000894	Anti-Inflammatory Agents, Non-Steroidal
MeSH PA	D018501	Antirheumatic Agents
MeSH PA	D018373	Peripheral Nervous System Agents

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Drug Use | Suggest Off label Use Form| |View source of the data|

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Disease	Relation	SNOMED_ID	DOID
Chronic ulcerative proctitis	indication	52231000
Chronic ulcerative rectosigmoiditis	indication	52506002
Ulcerative colitis	indication	64766004	DOID:8577
Ulcerative colitis in remission	indication	697969008
Crohn's disease	off-label use	34000006
Interstitial nephritis	contraindication	28689008	DOID:1063
Minimal change disease	contraindication	44785005	DOID:10966
Kidney disease	contraindication	90708001	DOID:557
Disease of liver	contraindication	235856003	DOID:409
Pyloric obstruction	contraindication	244815007

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🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	2.74	acidic
pKa2	13.47	acidic
pKa3	5.86	Basic

Orange Book patent data (new drug applications)

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Formulation strength	Trade name	Applicant	Application number	Approval date	Type	Dose form	Route	Patent number	Patent expiration date	Patent use
375MG	APRISO	VALEANT PHARMS INTL	N022301	Oct. 31, 2008	RX	CAPSULE, EXTENDED RELEASE	ORAL	8865688	May 1, 2030	FOR THE MAINTENANCE OF REMISSION OF ULCERATIVE COLITIS

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Orange Book exclusivity data (new drug applications)

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Formulation strength	Trade name	Applicant	Application number	Approval date	Type	Dose form	Route	Exclusivity date	Description
1.2GM	LIALDA	TAKEDA PHARMS USA	N022000	Jan. 16, 2007	RX	TABLET, DELAYED RELEASE	ORAL	June 26, 2023	NEW PATIENT POPULATION

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Bioactivity Summary:

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Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Bioact source	MoA source
Prostaglandin G/H synthase 2	Enzyme	P35354	PGH2_HUMAN	INHIBITOR	IC50	5.12	CHEMBL	CHEMBL
Prostaglandin G/H synthase 1	Enzyme	P23219	PGH1_HUMAN	INHIBITOR			WOMBAT-PK	CHEMBL
Arachidonate 5-lipoxygenase	Enzyme	P09917	LOX5_HUMAN	INHIBITOR			CHEMBL	CHEMBL
Peroxisome proliferator-activated receptor gamma	Nuclear hormone receptor	P37231	PPARG_HUMAN	AGONIST			UNKNOWN	IUPHAR
Tumor necrosis factor	Cytokine	P01375	TNFA_HUMAN		IC50	4.70	CHEMBL
Prostaglandin G/H synthase 1	Enzyme		PGH1_SHEEP		IC50	5.11	CHEMBL
Hydroxyacid oxidase 1	Enzyme		HAOX1_MOUSE		IC50	5.11	CHEMBL

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External reference:

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ID	Source
001600	NDDF
2700	IUPHAR_LIGAND_ID
37855	MMSL
37856	MMSL
387501005	SNOMEDCT_US
4019494	VUID
4019494	VANDF
4075	PUBCHEM_CID
4Q81I59GXC	UNII
5056	MMSL

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Pharmaceutical products:

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Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
Asacol HD	HUMAN PRESCRIPTION DRUG LABEL	1	0023-5901	TABLET, DELAYED RELEASE	800 mg	ORAL	NDA	31 sections
Asacol HD	HUMAN PRESCRIPTION DRUG LABEL	1	0023-5901	TABLET, DELAYED RELEASE	800 mg	ORAL	NDA	31 sections
Asacol HD	HUMAN PRESCRIPTION DRUG LABEL	1	0023-5901	TABLET, DELAYED RELEASE	800 mg	ORAL	NDA	31 sections
Delzicol	HUMAN PRESCRIPTION DRUG LABEL	1	0023-5853	CAPSULE, DELAYED RELEASE	400 mg	ORAL	NDA	31 sections
Delzicol	HUMAN PRESCRIPTION DRUG LABEL	1	0023-5853	CAPSULE, DELAYED RELEASE	400 mg	ORAL	NDA	31 sections
Mesalamine	HUMAN PRESCRIPTION DRUG LABEL	1	0093-5907	CAPSULE, DELAYED RELEASE	400 mg	ORAL	ANDA	26 sections
Mesalamine	HUMAN PRESCRIPTION DRUG LABEL	1	0093-5907	CAPSULE, DELAYED RELEASE	400 mg	ORAL	ANDA	26 sections
Mesalamine	HUMAN PRESCRIPTION DRUG LABEL	1	0093-5907	CAPSULE, DELAYED RELEASE	400 mg	ORAL	ANDA	26 sections
mesalamine	HUMAN PRESCRIPTION DRUG LABEL	1	0093-9224	CAPSULE, EXTENDED RELEASE	375 mg	ORAL	NDA authorized generic	26 sections
mesalamine	HUMAN PRESCRIPTION DRUG LABEL	1	0093-9224	CAPSULE, EXTENDED RELEASE	375 mg	ORAL	NDA authorized generic	26 sections

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