Sumatriptan

Modify Date: 2024-01-02 08:14:22

Sumatriptan Structure
Sumatriptan structure
Common Name Sumatriptan
CAS Number 103628-46-2 Molecular Weight 295.400
Density 1.2±0.1 g/cm3 Boiling Point 497.7±55.0 °C at 760 mmHg
Molecular Formula C14H21N3O2S Melting Point 169-171°C
MSDS N/A Flash Point 254.8±31.5 °C

 Use of Sumatriptan


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].

 Names

Name sumatriptan
Synonym More Synonyms

 Sumatriptan 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
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

 Customs

HS Code 29280090

 Articles1

More Articles
Temporal expression of transporters and receptors in a rat primary co-culture blood-brain barrier model.

Xenobiotica 44(10) , 941-51, (2014)

1. The more relevant primary co-cultures of brain microvessel endothelial cells and astrocytes (BMEC) are less utilized for screening of potential CNS uptake when compared to intestinal and renal cell...

 Synonyms

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
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