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Substance Name: Sulindac [USAN:USP:INN:BAN:JAN]
RN: 38194-50-2
UNII: 184SNS8VUH
InChIKey: MLKXDPUZXIRXEP-MFOYZWKCSA-N

Note

  • A sulfinylindene derivative prodrug whose sulfinyl moiety is converted in vivo to an active NSAID analgesic. Specifically, the prodrug is converted by liver enzymes to a sulfide which is excreted in the bile and then reabsorbed from the intestine. This helps to maintain constant blood levels with reduced gastrointestinal side effects.

Molecular Formula

  • C20-H17-F-O3-S

Molecular Weight

  • 356.4153
 

Classification Codes

  • Analgesics
  • Analgesics, Non-Narcotic
  • Anti-Inflammatory
  • Anti-Inflammatory Agents
  • Anti-Inflammatory Agents, Non-Steroidal
  • Antineoplastic Agents
  • Antirheumatic Agents
  • Cyclooxygenase Inhibitors
  • Drug / Therapeutic Agent
  • Enzyme Inhibitors
  • Human Data
  • Peripheral Nervous System Agents
  • Reproductive Effect
  • Sensory System Agents

Names and Synonyms

Name of Substance

  • Sulindac
  • Sulindac [USAN:USP:INN:BAN:JAN]

MeSH Heading

  • Sulindac

Synonyms

  • (Z)-(1)-5-Fluoro-2-methyl-1-((4-(methylsulphinyl)phenyl)methylene)-1H-indene-3-acetic acid
  • (Z)-5-Fluoro-2-methyl-1-((p-(methylsulfinyl)phenyl)methylene)-1H-indene-3-acetic acid
  • 1H-Indene-3-acetic acid, 5-fluoro-2-methyl-1-((4-(methylsulfinyl)phenyl)methylene)-, (Z)-
  • Aflodac
  • Algocetil
  • Arthrocine
  • Artribid
  • BRN 2951842
  • CCRIS 3305
  • cis-5-Fluoro-2-methyl-1-((4-(methylsulfinyl)phenyl)methylene)-1H-indene-3-acetic acid
  • cis-5-Fluoro-2-methyl-1-((p-methylsulfinyl)benzylidene)indene-3-acetic acid
  • cis-5-Fluoro-2-methyl-1-((p-methylsulfinyl)benzylidenyl)indene-3-acetic acid
  • cis-Sulindac
  • Citireuma
  • Clinoril
  • Clisundac
  • EINECS 253-819-2
  • EINECS 256-402-3
  • Imbaral
  • MK 231
  • Mobilin
  • Reumofil
  • Sudac
  • Sulindac
  • Sulindac sulfoxide
  • Sulindaco
  • Sulindaco [INN-Spanish]
  • Sulindacum
  • Sulindacum [INN-Latin]
  • Sulinol
  • Sulreuma
  • UNII-184SNS8VUH

Systematic Names

  • 1H-Indene-3-acetic acid, 5-fluoro-2-methyl-1-((4-(methylsulfinyl)phenyl)methylene)-, (Z)-
  • Sulindac

Superlist Name

  • Sulindac

Registry Numbers

CAS Registry Number

  • 38194-50-2

FDA UNII

  • 184SNS8VUH

Other Registry Number

  • 49627-22-7

System Generated Number

  • 0038194502

Structure Descriptors

InChI

1S/C20H17FO3S/c1-12-17(9-13-3-6-15(7-4-13)25(2)24)16-8-5-14(21)10-19(16)18(12)11-20(22)23/h3-10H,11H2,1-2H3,(H,22,23)/b17-9-

InChIKey

MLKXDPUZXIRXEP-MFOYZWKCSA-N

Smiles

CC\1=C(c2cc(ccc2/C1=C\c3ccc(cc3)S(=O)C)F)CC(=O)O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
infant LDLo oral 12mg/kg/2D-I (12mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

BLOOD: HEMORRHAGE

GASTROINTESTINAL: ULCERATION OR BLEEDING FROM STOMACH
Acta Paediatrica. Vol. 85, Pg. 884, 1996.
man TDLo oral 34mg/kg/6D-I (34mg/kg)   Journal of Rheumatology. Vol. 13, Pg. 1084, 1986.
man TDLo oral 43mg/kg/10D-I (43mg/kg) BLOOD: LEUKOPENIA

LIVER: LIVER FUNCTION TESTS IMPAIRED

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
JAMA, Journal of the American Medical Association. Vol. 244, Pg. 269, 1980.
man TDLo oral 343mg/kg (343mg/kg) BLOOD: "CHANGES IN SERUM COMPOSITION (E.G., TP, BILIRUBIN, CHOLESTEROL)"

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION
Journal of Toxicology, Clinical Toxicology. Vol. 33, Pg. 173, 1995.
mouse LD50 intraperitoneal 305mg/kg (305mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 13, Pg. 637, 1982.
mouse LD50 oral 507mg/kg (507mg/kg)   Drugs in Japan Vol. 6, Pg. APP-6, 1982.
mouse LD50 subcutaneous 398mg/kg (398mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 13, Pg. 637, 1982.
rat LD50 intraperitoneal 289mg/kg (289mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 13, Pg. 637, 1982.
rat LD50 oral 264mg/kg (264mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 30, Pg. 1398, 1980.
rat LD50 subcutaneous 336mg/kg (336mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 13, Pg. 637, 1982.
women LDLo oral 112mg/kg/2W-I (112mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING

LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), DIFFUSE"
Journal of Rheumatology. Vol. 10, Pg. 512, 1983.
women TDLo oral 8mg/kg/10H-I (8mg/kg) BEHAVIORAL: ANOREXIA (HUMAN

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)
Journal of Clinical Gastroenterology. Vol. 8, Pg. 569, 1986.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 183 deg C   EXP
pKa Dissociation Constant 4.7 (none)   EXP
log P (octanol-water) 3.42 (none)   EXP
Water Solubility 3000 mg/L   EXP
Vapor Pressure 1.18E-10 mm Hg 25 EST
Henry's Law Constant 1.25E-15 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 3.50E-10 cm3/molecule-sec 25 EST

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