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Substance Name: Mesalamine [USAN:USP]
RN: 89-57-6
UNII: 4Q81I59GXC
InChIKey: KBOPZPXVLCULAV-UHFFFAOYSA-N

Note

  • 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 Formula

  • C7-H7-N-O3

Molecular Weight

  • 153.1363
 

Classification Codes

  • Analgesics
  • Analgesics, Non-Narcotic
  • Anti-Inflammatory
  • Anti-Inflammatory Agents
  • Anti-Inflammatory Agents, Non-Steroidal
  • Antirheumatic Agents
  • Drug / Therapeutic Agent
  • Human Data
  • Peripheral Nervous System Agents
  • Sensory System Agents

Names and Synonyms

Name of Substance

  • Mesalamine
  • Mesalamine [USAN:USP]
  • Mesalazine [INN]

MeSH Heading

  • Mesalamine

Synonyms

  • 4-14-00-02058 (Beilstein Handbook Reference)
  • 5-Amino-2-hydroxybenzoic acid
  • 5-Aminosalicylic acid
  • 5-ASA
  • AI3-15564
  • Apriso
  • Asacol
  • Asacol HD
  • BRN 2090421
  • Canasa
  • CCRIS 7334
  • Claversal
  • Delzicol
  • EC 201-919-1
  • EINECS 201-919-1
  • HSDB 7512
  • Lialda
  • m-Aminosalicylic acid
  • Mesalamine
  • Mesalazina
  • Mesalazina [Spanish]
  • Mesalazine
  • Mesalazinum
  • Mesalazinum [Latin]
  • NSC 38877
  • p-Aminosalicylsaeure
  • p-Aminosalicylsaeure [German]
  • Pentacol
  • Pentasa
  • Rowasa
  • Salofalk
  • sfRowasa
  • SPD 476
  • UNII-4Q81I59GXC

Systematic Names

  • 5-Aminosalicylic acid
  • Benzoic acid, 5-amino-2-hydroxy-
  • Mesalazine
  • Salicylic acid, 5-amino-

Registry Numbers

CAS Registry Number

  • 89-57-6

FDA UNII

  • 4Q81I59GXC

Other Registry Number

  • 61513-32-4

Related Registry Numbers

  • 35589-28-7 (mono-hydrochloride salt)
  • 6291-36-7 (hydrochloride)

System Generated Number

  • 0000089576

Structure Descriptors

InChI

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

InChIKey

KBOPZPXVLCULAV-UHFFFAOYSA-N

Smiles

Nc1ccc(O)c(c1)C(=O)O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
man TDLo oral 51mg/kg/5D-I (51mg/kg)   Lancet. Vol. 1, Pg. 917, 1984.
man TDLo oral 51mg/kg/5D-I (51mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"		 Lancet. Vol. 1, Pg. 917, 1984.
man TDLo oral 321mg/kg/15D- (321mg/kg) SKIN AND APPENDAGES (SKIN): PHOTOSENSITIVITY: AFTER SYSTEMIC EXPOSURE American Journal of Gastroenterology. Vol. 94, Pg. 3386, 1999.
man TDLo oral 2057mg/kg/17W (2057mg/kg)   Lancet. Vol. 341, Pg. 1476, 1993.
man TDLo oral 2057mg/kg/17W (2057mg/kg) BLOOD: AGRANULOCYTOSIS Lancet. Vol. 341, Pg. 1476, 1993.
man TDLo oral 6857mg/kg/17W (6857mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING

LIVER: "JAUNDICE, CHOLESTATIC"		 Journal of Hepathology. Vol. 26, Pg. 425, 1997.
monkey LDLo oral 3gm/kg (3000mg/kg) KIDNEY, URETER, AND BLADDER: HEMATURIA

SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)		 Oyo Yakuri. Pharmacometrics. Vol. 47, Pg. 509, 1994.
mouse LD50 intraperitoneal 469mg/kg (469mg/kg)   Archiv der Pharmazie Vol. 332, Pg. 321, 1999.
mouse LD50 oral 3370mg/kg (3370mg/kg)   Archiv der Pharmazie Vol. 332, Pg. 321, 1999.
rabbit LD50 skin > 5gm/kg (5000mg/kg)   National Technical Information Service. Vol. OTS0570511,
rat LD50 intraperitoneal 1gm/kg (1000mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

KIDNEY, URETER, AND BLADDER: OTHER CHANGES IN URINE COMPOSITION

SKIN AND APPENDAGES (SKIN): HAIR: OTHER		 Oyo Yakuri. Pharmacometrics. Vol. 47, Pg. 505, 1994.
rat LD50 oral 2800mg/kg (2800mg/kg) GASTROINTESTINAL: OTHER CHANGES

BEHAVIORAL: FOOD INTAKE (ANIMAL)

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)		 National Technical Information Service. Vol. OTS0570511,
women TDLo oral 8mg/kg (8mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

BEHAVIORAL: HEADACHE		 Lancet. Vol. 1, Pg. 917, 1984.
women TDLo oral 80mg/kg/1D-I (80mg/kg) CARDIAC: PULSE RATE

VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION		 American Journal of Gastroenterology. Vol. 93, Pg. 470, 1998.
women TDLo oral 5400mg/kg/90D (5400mg/kg) GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF ENDOCRINE PANCREAS American Journal of Gastroenterology. Vol. 92, Pg. 2302, 1997.
women TDLo oral 8760mg/kg/1Y- (8760mg/kg) KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"

BEHAVIORAL: ANOREXIA (HUMAN

BEHAVIORAL: MUSCLE WEAKNESS		 Clinical Nephrology. Vol. 49, Pg. 265, 1998.
women TDLo oral 21800mg/kg/39 (21800mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

LUNGS, THORAX, OR RESPIRATION: "FIBROSIS, FOCAL (PNEUMOCONIOSIS)"

BLOOD: EOSINOPHILIA		 American Journal of Gastroenterology. Vol. 91, Pg. 1039, 1996.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 283 deg C   EXP
log P (octanol-water) 0.980 (none)   EST
Atmospheric OH Rate Constant 2.09E-11 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.