Sumatriptan

Names

[ Name ]:
Sumatriptan

[Synonym ]:
3-[2-(Dimethylamino)ethyl]-N-methyl-1H-indole-5-methanesulfonamide
1H-Indole-5-methanesulfonamide, 3-[2-(dimethylamino)ethyl]-N-methyl-
Sumatriptan
SUMATRIPTAN BASE
MFCD00902856
1H-Indole-5-methanesulfonamide, 3-(2-(dimethylamino)ethyl)-N-methyl-
GR 43175C
1-{3-[2-(Dimethylamino)ethyl]-1H-indol-5-yl}-N-methylmethanesulfonamide
IMITREX
IMIGRAN

Biological Activity

[Description]:

Sumatriptan (GR 43175 free base) is an orally active 5-HT1 receptor agonist with Kis of 17 nM, 27 nM and 100 nM for 5-HT1D, 5-HT1B and 5-HT1A receptors, respectively. Sumatriptan can be used for migraine headache research[1][2].

[Related Catalog]:

Research Areas >> Neurological Disease

Signaling Pathways >> GPCR/G Protein >> 5-HT Receptor

Signaling Pathways >> Neuronal Signaling >> 5-HT Receptor

[Target]

5-HT1A Receptor:100 nM (Ki)

5-HT1B Receptor:27 nM (Ki)

5-HT1D Receptor:17 nM (Ki)

[References]

[1]. S J Peroutka, et al. Sumatriptan (GR 43175) interacts selectively with 5-HT1B and 5-HT1D binding sites. Eur J Pharmacol. 1989 Apr 12;163(1):133-6.

[2]. K L Dechant, et al. Sumatriptan. A review of its pharmacodynamic and pharmacokinetic properties, and therapeutic efficacy in the acute treatment of migraine and cluster headache. Drugs. 1992 May;43(5):776-98.

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
497.7±55.0 °C at 760 mmHg

[ Melting Point ]:
169-171°C

[ Molecular Formula ]:
C₁₄H₂₁N₃O₂S

[ Molecular Weight ]:
295.400

[ Flash Point ]:
254.8±31.5 °C

[ Exact Mass ]:
295.135437

[ PSA ]:
73.58000

[ LogP ]:
0.67

[ Vapour Pressure ]:
0.0±1.3 mmHg at 25°C

[ Index of Refraction ]:
1.610

[ Storage condition ]:
2-8°C

[ Water Solubility ]:
21.4 mg/mL

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: NL9482200

CHEMICAL NAME :: 1H-Indole-5-methanesulfonamide, 3-(2-(dimethylamino)ethyl)-N-methyl-

CAS REGISTRY NUMBER :: 103628-46-2

LAST UPDATED :: 199612

DATA ITEMS CITED :: 11

MOLECULAR FORMULA :: C14-H21-N3-O2-S

MOLECULAR WEIGHT :: 295.44

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Human - man

DOSE/DURATION :: 86 mg/kg

TOXIC EFFECTS :: Cardiac - arrhythmias (including changes in conduction) Cardiac - EKG changes not diagnostic of specified effects

REFERENCE :: BMJOAE British Medical Journal. (British Medical Assoc., BMA House, Tavistock Sq., London WC1H 9JR, UK) V.1- 1857- Volume(issue)/page/year: 304,1415,1992

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Human - man

DOSE/DURATION :: 429 ug/kg/2W-I

TOXIC EFFECTS :: Behavioral - muscle weakness

REFERENCE :: LANCAO Lancet. (7 Adam St., London WC2N 6AD, UK) V.1- 1823- Volume(issue)/page/year: 341,1091,1993

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 120 ug/kg

TOXIC EFFECTS :: Behavioral - muscle weakness

REFERENCE :: LANCAO Lancet. (7 Adam St., London WC2N 6AD, UK) V.1- 1823- Volume(issue)/page/year: 341,1091,1993

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 240 ug/kg/1H-I

TOXIC EFFECTS :: Peripheral Nerve and Sensation - sensory change involving peripheral nerve Peripheral Nerve and Sensation - flaccid paralysis without anesthesia (usually neuromuscular blockage) Behavioral - hallucinations, distorted perceptions

REFERENCE :: LANCAO Lancet. (7 Adam St., London WC2N 6AD, UK) V.1- 1823- Volume(issue)/page/year: 343,1105,1994

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >2 gm/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - lacrimation Behavioral - ataxia Skin and Appendages - dermatitis, other (after systemic exposure)

REFERENCE :: HETOEA Human & Experimental Toxicology. (Macmillan Press Ltd., Brunel Road, Houndmills, Basingstoke, Hampshire, RG21 2XS, UK) V.9- 1990- Volume(issue)/page/year: 14,959,1995

TYPE OF TEST :: LD - Lethal dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >1 gm/kg

TOXIC EFFECTS :: Behavioral - tremor Lungs, Thorax, or Respiration - respiratory depression Skin and Appendages - dermatitis, other (after systemic exposure)

REFERENCE :: HETOEA Human & Experimental Toxicology. (Macmillan Press Ltd., Brunel Road, Houndmills, Basingstoke, Hampshire, RG21 2XS, UK) V.9- 1990- Volume(issue)/page/year: 14,959,1995

TYPE OF TEST :: LD - Lethal dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >20 mg/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - effect, not otherwise specified Lungs, Thorax, or Respiration - respiratory stimulation Skin and Appendages - dermatitis, other (after systemic exposure)

REFERENCE :: HETOEA Human & Experimental Toxicology. (Macmillan Press Ltd., Brunel Road, Houndmills, Basingstoke, Hampshire, RG21 2XS, UK) V.9- 1990- Volume(issue)/page/year: 14,959,1995

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >500 mg/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - mydriasis (pupillary dilation) Behavioral - ataxia Skin and Appendages - dermatitis, other (after systemic exposure)

REFERENCE :: HETOEA Human & Experimental Toxicology. (Macmillan Press Ltd., Brunel Road, Houndmills, Basingstoke, Hampshire, RG21 2XS, UK) V.9- 1990- Volume(issue)/page/year: 14,959,1995

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >100 mg/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - mydriasis (pupillary dilation) Gastrointestinal - changes in structure or function of salivary glands Skin and Appendages - dermatitis, other (after systemic exposure)

REFERENCE :: HETOEA Human & Experimental Toxicology. (Macmillan Press Ltd., Brunel Road, Houndmills, Basingstoke, Hampshire, RG21 2XS, UK) V.9- 1990- Volume(issue)/page/year: 14,959,1995 ** OTHER MULTIPLE DOSE TOXICITY DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 11648 mg/kg/26W-I

TOXIC EFFECTS :: Skin and Appendages - dermatitis, other (after systemic exposure)

REFERENCE :: HETOEA Human & Experimental Toxicology. (Macmillan Press Ltd., Brunel Road, Houndmills, Basingstoke, Hampshire, RG21 2XS, UK) V.9- 1990- Volume(issue)/page/year: 14,959,1995 ** TUMORIGENIC DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 146 gm/kg/2Y-I

TOXIC EFFECTS :: Tumorigenic - Carcinogenic by RTECS criteria Endocrine - tumors Reproductive - Tumorigenic effects - testicular tumors

REFERENCE :: HETOEA Human & Experimental Toxicology. (Macmillan Press Ltd., Brunel Road, Houndmills, Basingstoke, Hampshire, RG21 2XS, UK) V.9- 1990- Volume(issue)/page/year: 14,959,1995

Safety Information

[ Hazard Codes ]:
Xi

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
S26-S36/37/39-S45-S28A

[ RIDADR ]:
UN 3261 8/PG 2

[ WGK Germany ]:
3

[ RTECS ]:
NL9482200

[ HS Code ]:
29280090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 29280090

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