CAS 103628-48-4|Sumatriptan succinate

Introduction：Basic information about CAS 103628-48-4|Sumatriptan succinate, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Sumatriptan succinate BiologicalActivity
3. Chemical & Physical Properties
4. Toxicological Information
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
5. Safety Information
6. Customs
7. Articles33
8. Synonyms

Common Name	Sumatriptan succinate
CAS Number	103628-48-4	Molecular Weight	341.426
Density	1.2±0.1 g/cm3	Boiling Point	497.7ºC at 760 mmHg
Molecular Formula	C₁₈H₂₇N₃O₆S	Melting Point	165-166°C
MSDS	USA	Flash Point	254.8ºC
Symbol	GHS05	Signal Word	Danger

Names

Name	sumatriptan succinate
Synonym	More Synonyms

Sumatriptan succinate BiologicalActivity

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 DiseaseSignaling Pathways >>GPCR/G Protein >>5-HT ReceptorSignaling 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.

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 DiseaseSignaling Pathways >>GPCR/G Protein >>5-HT ReceptorSignaling 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
InChIKey	PORMUFZNYQJOEI-UHFFFAOYSA-N
SMILES	CNS(=O)(=O)Cc1ccc2[nH]cc(CCN(C)C)c2c1.O=C(O)CCC(=O)O
Storage condition	Store at +4°C

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

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%

Articles33

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...

Synonyms

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)

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