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Substance Name: Sumatriptan [USP:INN:BAN]
RN: 103628-46-2
UNII: 8R78F6L9VO
InChIKey: KQKPFRSPSRPDEB-UHFFFAOYSA-N

Note

  • A serotonin agonist that acts selectively at 5HT1 receptors. It is used in the treatment of MIGRAINE DISORDERS.

Molecular Formula

  • C14-H21-N3-O2-S

Molecular Weight

  • 295.4049
 

Classification Codes

  • Cardiovascular Agents
  • Drug / Therapeutic Agent
  • Human Data
  • Neurotransmitter Agents
  • Serotonin 5-HT1 Receptor Agonists
  • Serotonin Agents
  • Serotonin Receptor Agonists
  • Tumor Data
  • Vasoconstrictor Agents

Names and Synonyms

Name of Substance

  • Sumatriptan
  • Sumatriptan [USP:INN:BAN]

MeSH Heading

  • Sumatriptan

Synonyms

  • 3-(2-(Dimethylamino)ethyl)-N-methyl-1H-indole-5-methanesulfonamide
  • AVP 825
  • AVP-825
  • AVP825
  • BRN 6930870
  • GR 43175
  • GR 43175X
  • GR-43175
  • HSDB 7742
  • Imitrex
  • Onzetra Xsail
  • Sumatran
  • Sumatriptan
  • Sumatriptanum
  • Sumatriptanum [INN-Latin]
  • Sumax
  • UNII-8R78F6L9VO
  • Zecuity
  • Zembrace SymTouch

Systematic Name

  • 1H-Indole-5-methanesulfonamide, 3-(2-(dimethylamino)ethyl)-N-methyl-

Registry Numbers

CAS Registry Number

  • 103628-46-2

FDA UNII

  • 8R78F6L9VO

Related Registry Number

  • 103628-48-4 (succinate)

System Generated Number

  • 0103628462

Structure Descriptors

InChI

1S/C14H21N3O2S/c1-15-20(18,19)10-11-4-5-14-13(8-11)12(9-16-14)6-7-17(2)3/h4-5,8-9,15-16H,6-7,10H2,1-3H3

InChIKey

KQKPFRSPSRPDEB-UHFFFAOYSA-N

Smiles

CNS(=O)(=O)Cc1ccc2c(c1)c(c[nH]2)CCN(C)C

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
man TDLo subcutaneous 429ug/kg/2W-I (0.429mg/kg) BEHAVIORAL: MUSCLE WEAKNESS Lancet. Vol. 341, Pg. 1091, 1993.
man TDLo subcutaneous 86mg/kg (86mg/kg) CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION)

CARDIAC: EKG CHANGES NOT DIAGNOSTIC OF ABOVE
British Medical Journal. Vol. 304, Pg. 1415, 1992.
mouse LDLo oral > 500mg/kg (500mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"

BEHAVIORAL: ATAXIA

SENSE ORGANS AND SPECIAL SENSES: MYDRIASIS (PUPILLARY DILATION): EYE
Human & Experimental Toxicology. Vol. 14, Pg. 959, 1995.
mouse LDLo subcutaneous > 100mg/kg (100mg/kg) GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS

SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"

SENSE ORGANS AND SPECIAL SENSES: MYDRIASIS (PUPILLARY DILATION): EYE
Human & Experimental Toxicology. Vol. 14, Pg. 959, 1995.
rat LD intravenous > 20mg/kg (20mg/kg) SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE

SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION
Human & Experimental Toxicology. Vol. 14, Pg. 959, 1995.
rat LD subcutaneous > 1gm/kg (1000mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"

BEHAVIORAL: TREMOR

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Human & Experimental Toxicology. Vol. 14, Pg. 959, 1995.
rat LDLo oral > 2gm/kg (2000mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"

BEHAVIORAL: ATAXIA

SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE
Human & Experimental Toxicology. Vol. 14, Pg. 959, 1995.
women TDLo subcutaneous 120ug/kg (0.12mg/kg) BEHAVIORAL: MUSCLE WEAKNESS Lancet. Vol. 341, Pg. 1091, 1993.
women TDLo subcutaneous 120ug/kg (0.12mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING

CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP

CARDIAC: EKG CHANGES NOT DIAGNOSTIC OF ABOVE
Annals of Internal Medicine. Vol. 129, Pg. 874, 1998.
women TDLo subcutaneous 240ug/kg/1H-I (0.24mg/kg) PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE)

PERIPHERAL NERVE AND SENSATION: SENSORY CHANGE INVOLVING PERIPHERAL NERVE

BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"
Lancet. Vol. 343, Pg. 1105, 1994.

Physical Properties

Physical Property Value Units Temp (deg C) Source
log P (octanol-water) 0.93 (none)   EXP
Water Solubility 2.14E+04 mg/L 25 EST
Vapor Pressure 7.05E-09 mm Hg 25 EST
Henry's Law Constant 4.47E-14 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 2.89E-10 cm3/molecule-sec 25 EST

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