Sumatriptan succinate

Names

[ Name ]:
Sumatriptan succinate

[Synonym ]:
Sumatriptan succinate
1-{3-[2-(dimethylamino)ethyl]-1H-indol-5-yl}-N-methylmethanesulfonamide butanedioate (1:1)
3-[2-(Dimethylamino)ethyl]-N-methyl-1H-indole-5-methanesulfonamide,butanedioate(1:1)
1-(3-(2-(Dimethylamino)ethyl)-1H-indol-5-yl)-N-methylmethanesulfonamide succinate
1H-Indole-5-methanesulfonamide, 3-[2-(dimethylamino)ethyl]-N-methyl-, butanedioate (1:1)
1-{3-[2-(Dimethylamino)ethyl]-1H-indol-5-yl}-N-methylmethanesulfonamide succinate
3-[2-(Dimethylamino)ethyl]-1H-indol-5-yl-N-methylmethanesulfonamide Succinate
acide butanedioïque - 1-{3-[2-(diméthylamino)éthyl]-1H-indol-5-yl}-N-méthylméthanesulfonamide (1:1)
Benzamide, 4-(aminosulfonyl)-N-[(1-ethyl-2-pyrrolidinyl)methyl]-2-methoxy-
MFCD00866222
N-[(1-Ethyl-2-pyrrolidinyl)methyl]-2-methoxy-4-sulfamoylbenzamide
1-{3-[2-(dimethylamino)ethyl]-1H-indol-5-yl}-N-methylmethanesulfonamide butanedioate
Butandisäure--1-{3-[2-(dimethylamino)ethyl]-1H-indol-5-yl}-N-methylmethansulfonamid(1:1)
Succinic acid - 1-{3-[2-(dimethylamino)ethyl]-1H-indol-5-yl}-N-methylmethanesulfonamide (1:1)
1-{3-[2-(Dimethylamino)ethyl]-1H-indol-5-yl}-N-methylmethanesulfonamide succinate (1:1)

Biological Activity

[Description]:

Sumatriptan succinate (GR 43175) is a serotonin1 (5-HT1) receptor agonist, which is effective in the acute treatment of migraine headache.Target: 5-HT 1d receptor agonistSumatriptan succinate is a serotonin1 (5-HT1) receptor agonist, which is effective in the acute treatment of migraine headache. Its antimigraine activity is believed to derive from selective vasoconstriction of cranial blood vessels which are dilated and distended during migraine headache and/or from inhibition of neurogenically mediated inflammation in the dura mater [1].For sumatriptan succinate 50 mg versus placebo the NNTs were 6.1, 7.5, and 4.0 for pain-free at two hours and headache relief at one and two hours, respectively. NNTs for sustained pain-free and sustained headache relief during the 24 hours postdose were 9.5 and 6.0, respectively [2]. Difference in time-weighted (0-2.5 h) mean arterial pressure MAP (90% confidence interval) was 1.2 mmHg (-0.2, 2.7) between telcagepant and placebo, 4.0 mmHg (2.5, 5.5) between sumatriptan succinate and placebo, and 1.5 mmHg (0.0, 3.0) between telcagepant with sumatriptan succinate vs sumatriptan succinate alone. When coadministered with telcagepant, the AUC0-6h and C(max) of sumatriptan succinate were increased by 23% and 24%, respectively. The small MAP increases observed after coadministration could possibly be associated with the slight elevations in sumatriptan succinate levels [3].Clinical indications: Cluster headache; MigraineToxicity: Symptoms of overdose include convulsions, tremor, paralysis, inactivity, ptosis, erythema of the extremities, abnormal respiration, cyanosis, ataxia, mydriasis, salivation, and lacrimation

[Related Catalog]:

Research Areas >> Neurological Disease

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

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

[References]

[1]. Dechant KL, et al. Sumatriptan. A review of its pharmacodynamic and pharmacokinetic properties, and therapeutic efficacy in the acute treatment of migraine and cluster headache.

[2]. Derry CJ, et al. Sumatriptan (oral route of administration) for acute migraine attacks in adults. Cochrane Database Syst Rev. 2012 Feb 15;2:CD008615.

[3]. Depré M, et al. Lack of hemodynamic interaction between CGRP-receptor antagonist telcagepant (MK-0974) and sumatriptan: results from a randomized study in patients with migraine. Cephalalgia. 2013 Dec;33(16):1292-301.

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
497.7ºC at 760 mmHg

[ Melting Point ]:
165-166°C

[ Molecular Formula ]:
C₁₈H₂₇N₃O₆S

[ Molecular Weight ]:
341.426

[ Flash Point ]:
254.8ºC

[ Exact Mass ]:
341.140930

[ PSA ]:
148.18000

[ LogP ]:
0.34

[ Vapour Pressure ]:
1.24E-17mmHg at 25°C

[ Index of Refraction ]:
1.552

[ Storage condition ]:
Store at +4°C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: EJ9940000

CAS REGISTRY NUMBER :: 103628-48-4

LAST UPDATED :: 199606

DATA ITEMS CITED :: 9

MOLECULAR FORMULA :: C14-H21-N3-O2-S.C4-H6-O4

MOLECULAR WEIGHT :: 413.54

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >2939 mg/kg

TOXIC EFFECTS :: Behavioral - tremor Lungs, Thorax, or Respiration - respiratory depression Gastrointestinal - changes in structure or function of salivary glands

REFERENCE :: YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 21,2059,1993

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1680 mg/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - cyanosis Lungs, Thorax, or Respiration - respiratory depression

REFERENCE :: YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 21,2059,1993

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 43112 ug/kg

TOXIC EFFECTS :: Lungs, Thorax, or Respiration - respiratory depression Liver - other changes

REFERENCE :: YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 21,2059,1993

TYPE OF TEST :: LD - Lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: >700 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Behavioral - ataxia Gastrointestinal - changes in structure or function of salivary glands

REFERENCE :: YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 21,2065,1993

TYPE OF TEST :: LD - Lethal dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: >140 mg/kg

TOXIC EFFECTS :: Behavioral - tremor Gastrointestinal - changes in structure or function of salivary glands

REFERENCE :: YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 21,2065,1993 ** REPRODUCTIVE DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 5250 mg/kg

SEX/DURATION :: male 10 week(s) pre-mating female 2 week(s) pre-mating - 3 week(s) after conception

TOXIC EFFECTS :: Reproductive - Maternal Effects - ovaries, fallopian tubes Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea) Reproductive - Fertility - litter size (e.g. # fetuses per litter; measured before birth)

REFERENCE :: YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 22,3817,1994

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 2600 mg/kg

SEX/DURATION :: female 18-21 day(s) after conception lactating female 22 day(s) post-birth

TOXIC EFFECTS :: Reproductive - Maternal Effects - other effects Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain)

REFERENCE :: YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 22,3849,1994

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 26 gm/kg

SEX/DURATION :: female 18-21 day(s) after conception lactating female 22 day(s) post-birth

TOXIC EFFECTS :: Reproductive - Effects on Newborn - live birth index (measured after birth) Reproductive - Effects on Newborn - viability index (e.g., # alive at day 4 per # born alive) Reproductive - Effects on Newborn - other postnatal measures or effects

REFERENCE :: YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 22,3849,1994

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 3500 mg/kg

SEX/DURATION :: male 10 week(s) pre-mating

TOXIC EFFECTS :: Reproductive - Paternal Effects - prostate, seminal vesicle, Cowper's gland, accessory glands

REFERENCE :: YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 22,3817,1994

Safety Information

[ Symbol ]:

GHS05

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H318

[ Precautionary Statements ]:
P280-P305 + P351 + P338 + P310

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xi: Irritant;

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
S16-S26-S36-S61-S60

[ RIDADR ]:
UN 1648 3/PG 2

[ HS Code ]:
2935009090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2935009090

[ Summary ]:
2935009090 other sulphonamides VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:6.5% General tariff:35.0%

Articles

Multidrug toxicity involving sumatriptan.

J. Anal. Toxicol. 39(1) , 75-9, (2015)

A multidrug fatality involving sumatriptan is reported. Sumatriptan is a tryptamine derivative that acts at 5-HT(1B/1D) receptors and is used for the treatment of migraines. The decedent was a 21-year...

Thermal and 31P-NMR studies to elucidate sumatriptan succinate entrapment behavior in phosphatidylcholine/cholesterol liposomes. Comparative 31P-NMR analysis on negatively and positively-charged liposomes.

Colloids Surf. B Biointerfaces 105 , 14-23, (2013)

In this paper, two techniques, differential scanning calorimetry (DSC) and phosphorus nuclear magnetic resonance ((31)P-NMR), have been used to characterize sumatriptan succinate-loaded charged liposo...

Identification of active ingredients in Wuzhuyu decoction improving migraine in mice by spectral efficiency association.

Mol. Med. Report. 12 , 1524-34, (2015)

Wuzhuyu decoction is a traditional Chinese medicine used for the effective treatment of migraines, termed 'Jueyin headache', in China. However, there have been few investigations to clarify the compos...