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ChemicalBook > CAS DataBase List > Sumatriptan succinate

Sumatriptan succinate

Description References
Product Name
Sumatriptan succinate
CAS No.
103628-48-4
Chemical Name
Sumatriptan succinate
Synonyms
SuMitrex;gr43175c;Sumatriptan succinat;Sumatriptan succinate;methanesulfonamide(1:1);SumatriptanSuccinate>Penehyclidine Impurity 9;SUMATRIPTANSUCCINATE(1:1);SuMatriptan Succinate, EP;Sumatriptan succinate CRS
CBNumber
CB1135040
Molecular Formula
C18H27N3O6S
Formula Weight
413.48848
MOL File
103628-48-4.mol
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Sumatriptan succinate Property

Melting point:
165-166°C
storage temp. 
-20°C
solubility 
H2O: >20mg/mL
form 
solid
color 
white to off-white
Merck 
14,8997
BCS Class
3
InChIKey
PORMUFZNYQJOEI-UHFFFAOYSA-N
CAS DataBase Reference
103628-48-4(CAS DataBase Reference)
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Safety

Hazard Codes 
Xi
Risk Statements 
36/37/38-41
Safety Statements 
26-36-39
RIDADR 
3077
WGK Germany 
3
RTECS 
EJ9940000
HS Code 
29350090
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H412Harmful to aquatic life with long lasting effects

Precautionary statements

P202Do not handle until all safety precautions have been read and understood.

P273Avoid release to the environment.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P308+P313IF exposed or concerned: Get medical advice/attention.

P405Store locked up.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
S1198
Product name
Sumatriptan succinate
Purity
≥98% (HPLC), solid
Packaging
10mg
Price
$117
Updated
2024/03/01
Sigma-Aldrich
Product number
PHR2580
Product name
Sumatriptan Succinate
Purity
pharmaceutical secondary standard, certified reference material
Packaging
500MG
Price
$302
Updated
2024/03/01
Sigma-Aldrich
Product number
1642201
Product name
Sumatriptan succinate
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
200mg
Price
$581
Updated
2024/03/01
TCI Chemical
Product number
S0851
Product name
Sumatriptan Succinate
Purity
>98.0%(HPLC)(T)
Packaging
100mg
Price
$131
Updated
2024/03/01
TCI Chemical
Product number
S0851
Product name
Sumatriptan Succinate
Purity
>98.0%(HPLC)(T)
Packaging
1g
Price
$636
Updated
2024/03/01
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Sumatriptan succinate Chemical Properties,Usage,Production

Description

Sumatriptan succinate is a synthetic drug belonging to a class of medications known as 5-hydroxytryptamine agonists (also called "triptans"), which is commonly used to treat cluster and migraine headaches with or without aura (warning signs occurring prior to the onset of a migraine). It is effective to relieve or eliminate the intensity of migraine and cluster headaches and accompanying symptoms including sensitivity to light or sound, nausea, and vomiting. However, it cannot help prevent future migraines/headaches or decrease the frequency of getting migraine and it is not recommended for other types of headache or for headache prevention.
It is believed that the pain of migraine headaches is induced by dilated blood vessels inside the head. Sumatriptan succinate relieves migraine headaches by affecting the serotonin in the brain, which results in constriction of blood vessels. Subcutaneous injection of this drug is more effective than other formulations.

References

https://en.wikipedia.org/wiki/Sumatriptan
http://www.medicinenet.com/sumatriptan_succinate-injection/article.htm
http://bodyandhealth.canada.com/drug/getdrug/teva-sumatriptan-df
http://www.webmd.com/drugs/2/drug-7741/sumatriptan-oral/details

Description

Sumatriptan succinate is a highly selective 5HT1-like receptor agonist introduced as a new treatment for migraine. It is indicated for the acute relief of migraine and cluster headache. Oral administration is reported to be free of substantial side effects. The compound appears to be a significant advance over the use of ergotamine and other agents in the treatment of migraine.

Chemical Properties

White Crystalline Powder

Originator

Glaxo (United Kingdom)

Uses

A serotonin 5HT1-receptor agonist

Uses

H1-antihistamine

Uses

A selective 5-HT1 receptor agonist

Uses

Sumatriptan (succinate) is a serotonin 5-hydroxytryptamine 1 (5-HT1) receptor agonist with selective affinity for 5-HT1B and 5-HT1D receptors with IC50 values of 9.3 and 7.3 nM, respectively. It also has affinity for the 5-HT1F receptor (IC50 = 17.8 nM). Sumatriptan (succinate) has been shown to induce vasoconstriction of human middle meningeal arteries (EC50 = 89.9 nM) and reduce vascular inflammation associated with migraines.

Uses

Sumatriptan Succinate is a selective 5-HT1B/1D-receptor agonist with anticonvulsant properties (1,2). Sumatriptan Succinate is used for migraine relief (2).

Definition

ChEBI: A succinate salt obtained by reaction of sumatriptan with one equivalent of succinic acid. Selective agonist for a vascular 5-HT1 receptor subtype (probably a member of the 5-HT1D family). Used for the acute treatm nt of migraine with or without aura in adults.

Manufacturing Process

A solution of (phenylthio)acetaldehyde (6.05 g) in absolute ethanol (180 ml) was added over 10 min to a solution of 4-hydrazino-Nmethylbenzenemethanesulphonamide hydrochloride (10 g) in water (180 ml) with cooling. After addition of the aldehyde was complete, the mixture was stirred at 5°C for a period of 14 h. The precipitated solid was filtered off, washed with water (200 ml), hexane (200 ml) and dried in vacuo to give the N-methyl-4-[2-[2-(phenylthio)ethylidene]hydrazino]benzenemethanesulphonamide (10.95 g), melting point 110°-112°C.
A solution of the N-methyl-4-[2-[2- (phenylthio)ethylidene]hydrazino]benzenemethane-sulphonamide in absolute ethanol (300 ml) was saturated with hydrogen chloride gas (ca. 30 min) whilst being cooled in an ice-water bath, allowed to stir at room temperature for 3 h and filtered. The filtrate was concentrated in vacuo and chromatographed to afford a foam, which solidified on trituration with ether to an amorphous powder (2.17 g). A sample was recrystallized from hexane-dichloromethane to give the N-methyl-3-(phenylthio)-1H-indole-5-methanesulphonamide, melting point 133°-134°C.
To a solution of N-methyl-3-(phenylthio)-1H-indole-5-methanesulphonamide (460 mg) in absolute ethanol (50 ml) was added Raney nickel [4.6 g, 50% slurry in water, washed to neutrality with deionized water (60 ml)] and the reaction mixture refluxed for 16 h under an atmosphere of nitrogen. On cooling to room temperature, the supernatant was removed and the Raney nickel extracted with ethanol (2x50 ml, which was brought to a gentle reflux for 15 min under an atmosphere of nitrogen). The combined extracts were filtered through a sand-celite pad and concentrated in vacuo. Chromatography of the residue, afforded an oil (87 mg) which crystallized from ether-hexane to give the N-methyl-1H-indole-5-methanesulphonamide (90 mg), melting point 127°-129°C.
To N,N-diethyl chloroacetamide (800 mg) at 0°C was added phosphorous oxychloride (250 μl) over a period of 30 sec. After the addition was complete, the mixture was allowed to stir at 0°C for 15 min and then at room temperature for 20 min. The N-methyl-1H-indole-5-methanesulphonamide (300 mg) was added at 0°C and the mixture warmed to 65°C, whereupon it dissolved. The mixture was stirred for 2 h at this temperature then poured onto ice (ca. 5 g) and chloroform (5 ml) and stirred vigorously for 1 h. A solid was filtered off, washed with water (50 ml), and hexane (100 ml) and dried in vacuo to give the 3-(chloroacetyl)-N-methyl-1H-indole-5- methanesulphonamide (192 mg).
A solution of the 3-(chloroacetyl)-N-methyl-1H-indole-5- methanesulphonamide (160 mg) in ethanolic dimethylamine (30 ml, 33% w/v solution in ethanol) was heated to reflux for 2 h. On cooling to room temperature the solvent was removed in vacuo and the residue was chromatographed to afford the 3-[(dimethylamino)acetyl]-N-methyl-1Hindole- 5-methanesulphonamide, melting point 230°C, dec.
To a suspension of the 3-[(dimethylamino)acetyl]-N-methyl-1H-indole-5- methanesulphonamide (46.5 mg) in 1-propanol (5 ml) was added sodium borohydride (62 mg). The reaction mixture was brought to reflux for a period of 3 h, then an additional quantity of borohydride (60 mg) was added. After refluxing for a further 1 h, the mixture was allowed to cool to room temperature and quenched with 2 N HCl (10 ml). The aqueous solution was washed with ethyl acetate (5 ml) then neutralized (NaHCO3 solution) and extracted with ethyl acetate (3 x 15 ml). The combined extracts were concentrated in vacuo and the residue chromatographed to give the 3-[2- (dimethylamino)ethyl]-N-methyl 1H-indole-5-methanesulphonamide as a gum (2 mg) which was shown by TLC.
Succinic acid in hot methanol was added to a hot solution of the the 3-[2- (dimethylamino)ethyl]-N-methyl-1H-indole-5-methanesulphonamide in absolute ethanol and the mixture was heated to reflux with stirring to give a solution. The solution was allowed to cool with stirring to room temperature, and the resultant suspension was farther cooled in an ice-bath for 2 h. The solid was filtered off, washed with ethanol, and dried in vacuo to give the 3- [2-(dimethylamino)ethyl]-N-methyl-1H-indole-5-methanesulphonamide, salt with succinic acid (1:1).

brand name

Imitrex (GlaxoSmithKline);Imigran.

Therapeutic Function

Serotoninergic

World Health Organization (WHO)

Suprofen, a nonsteroidal anti-inflammatory agent, was introduced in 1983 for use as an analgesic for the symptomatic relief of mild to moderate pain and for primary dysmenorrhoea. By 1986 it had become evident that its use was occasionally associated with flank pain sometimes accompanied by evidence of decreased renal function. The Arthritis Advisory Committee of the United States Food and Drug Administration met in December 1986 to review the situation and decided against withdrawing suprofen from the market. However, in May 1987 the Committee for Proprietary Medicinal Products of the European Community recommended that all marketing authorizations should be suspended. The manufacturer subsequently decided to suspend sale worldwide on the grounds that sales had diminished to the point where the product was no longer economically viable.

Biological Activity

Selective 5-HT 1 receptor agonist (K i values are 17, 27 and 100 nM at 5-HT 1D , 5-HT 1B and 5-HT 1A receptors respectively). Antimigraine agent.

Biochem/physiol Actions

Sumatriptan succinate is a 5-HT1 serotonin receptor agonist.

storage

+4°C

Sumatriptan succinate Preparation Products And Raw materials

Raw materials

Preparation Products

Sumatriptan
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View Lastest Price from Sumatriptan succinate manufacturers

WUHAN FORTUNA CHEMICAL CO., LTD
Product
Sumatriptan succinate 103628-48-4
Price
US $0.00/g
Min. Order
1g
Purity
99%
Supply Ability
1kg/month
Release date
2021-06-18
Hebei Weibang Biotechnology Co., Ltd
Product
Sumatriptan succinate 103628-48-4
Price
US $10.00/KG
Min. Order
100KG
Purity
99%
Supply Ability
100 mt
Release date
2021-09-26
Hebei Mojin Biotechnology Co., Ltd
Product
Sumatriptan succinate 103628-48-4
Price
US $0.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
50000KG/month
Release date
2023-08-17

103628-48-4, Sumatriptan succinateRelated Search:

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  • Sumatriptan SuccinateQ: What is Sumatriptan Succinate Q: What is the CAS Number of Sumatriptan Succinate Q: What is the storage condition of Sumatriptan Succinate Q: What are the applications of Sumatriptan Succinate
  • Sumatriptan Succinate (1642201)
  • R = CH3: N-methyl(2-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-6-yl)methanesulfonamide
  • [3-[2-(Dimethyl amino) ethyl]-1H-indol-5-yl]-N-methyl methane sulphonamide (Sumatriptan Base)
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  • C14H21N3O2SC4H6O4
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