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Sumatriptan succinate

Sumatriptan succinate structure

CAS No:
103628-48-4
Formula:
C14H21N3O2S.C4H6O4
Chemical Name:
Sumatriptan succinate
Synonyms:
Butanedioic acid,compd. with 3-[2-(dimethylamino)ethyl]-N-methyl-1H-indole-5-methanesulfonamide (1:1);1H-Indole-5-methanesulfonamide,3-[2-(dimethylamino)ethyl]-N-methyl-,butanedioate (1:1);Sumatriptan succinate;GR 43175C;Imigran;Imitrex;Imigrane;Sumitrex;Migragesin;Megrelan;Imiject;Treximet;Sumagraine;Suminat;1-[3-[2-(Dimethylamino)ethyl]-1H-indol-5-yl]-N-methylmethanesulfonamide butanedioic acid
Categories:
Active Pharmaceutical Ingredients > Circulatory System Drugs

Description

White Crystalline PowderChEBI: 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.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

Sumatriptan succinate is 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 treatment of migraine with or without aura in adults. It has a role as a serotonergic agonist and a vasoconstrictor agent. It contains a sumatriptan(1+).|Sumatriptan Succinate is the succinate salt form of sumatriptan, a member of the triptan class of compounds with anti-migraine property. Sumatriptan succinate selectively binds to and activates serotonin 5-HT1 receptors. This results in constriction of meningeal, dural, cerebral or pial blood vessels via stimulation of the 5-HT1B receptors, thereby reducing the vascular pulsation and may provide relief in migraine headaches. Furthermore, agonistic action of this agent through presynaptic stimulation of 5-HT1D and/or 5-HT1F receptors prevents release of vasoactive and pro-inflammatory neuropeptide (calcitonin gene-related peptide), thereby may also relieve migraine headaches. In addition, central inhibition of pain transmission via the inhibition of trigeminal neurons in the brain stems and upper spinal cord mediated by 5-HT1B, 5-HT1D or 5-HT 1F receptors also aides in the alleviation of migraine pain.|A serotonin agonist that acts selectively at 5HT1 receptors. It is used in the treatment of MIGRAINE DISORDERS.

Sumatriptan succinate Basic Attributes

Molecular Weight：

413.49

Exact Mass：

341.140930

EC Number：

1308068-626-2

UNII：

J8BDZ68989

NSC Number：

760362

DSSTox ID：

DTXSID60145966

NCI Thesaurus Code：

C29470

HScode：

29350090

Characteristics

PSA：

148

XLogP3：

2.72870

Appearance：

white to off-white

Density：

1.2±0.1 g/cm3

Melting Point：

165-166 °C

Boiling Point：

647.2°C at 760 mmHg

Flash Point：

254.8ºC

Refractive Index：

1.552

Water Solubility：

H2O: >20mg/mL

Storage Conditions：

Store at +4°C

Vapor Pressure：

7.05X10-9 mm Hg at 25 deg C (est)

Safety Information

Packing level：

Ⅲ

Transport codes：

3077

wgk germany：

hazard class code：

36/37/38-41

safety instructions：

26-36-39

RTECS Number：

EJ9940000

Marks：

Precautionary statement(s)：

P280-P305 + P351 + P338 + P310

Hazard Statements：

H318

GHS Classification：

|Danger|H318 (78.85%): Causes serious eye damage [Danger Serious eye damage/eye irritation]|P201, P202, P273, P280, P281, P305+P351+P338, P308+P313, P310, P405, and P501|Aggregated GHS information provided by 52 companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Drug Information

MeSH：

Endogenous compounds and drugs that specifically stimulate SEROTONIN 5-HT1 RECEPTORS. Included under this heading are agonists for one or more of the specific 5-HT1 receptor subtypes. (See all compounds classified as Serotonin 5-HT1 Receptor Agonists.)|Drugs used to cause constriction of the blood vessels. (See all compounds classified as Vasoconstrictor Agents.)

MeSH Entry Terms：

3-(2-(Dimethylamino)ethyl)-N-methyl-1H-indole-5-methanesulfonamide

Sumatriptan succinate Use and Manufacturing

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.

Use Classification：

Human drugs -> Sumatriptan Galpharm -> EMA Drug Category|Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients

Computed Properties

Molecular Weight:413.5
Hydrogen Bond Donor Count:4
Hydrogen Bond Acceptor Count:8
Rotatable Bond Count:9
Exact Mass:413.16205676
Monoisotopic Mass:413.16205676
Topological Polar Surface Area:148
Heavy Atom Count:28
Complexity:498
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes

Drug Function and Efficacy

Sumatriptan is a selective agonist of vascular 5-HT1D receptors, acting on the human basilar artery and cerebrospinal dural vascular system, causing vasoconstriction, which may be related to its migraine relief effect.

This ingredient has been used in drugs with the following functions (note: it does not mean that the ingredient itself has the following health functions)

Related Drugs

Sumatriptan succinate capsules
Ingredients	Chemical name: 3-[2-(dimethylamino)ethyl]-N-methylindole-5-methanesulfonamide succinate. Chemical structure: Molecular formula: C14H21N3O2SC4H6O4 Molecular weight: 413.49
Indication	Drugs containing ergotamine may exacerbate vasospastic reactions. Theoretically, the simultaneous use of ergotamine-containing drugs or ergotamine-like drugs (such as dihydroergotamine or dihydroergonovine) within 24 hours can make this reaction worse, so it should be avoided. For patients taking monoamine oxidase inhibitors, taking the recommended dose of sumatriptan at the same time, the blood concentration can reach 7 times that of taking the same dose of sumatriptan alone. Therefore, the two are prohibited from being used in combination. There are reports that selective serotonin uptake inhibitors (SSRIS) (such as fluoxetine, FLUVOXAMINE, paroxetine, sertraline) occasionally cause weakness, hyperreflexia and ataxia when used in combination with sumatriptan. If it must be used in combination, it is recommended that the patient be properly observed. [Overdose] In a trial, 670 patients took a single dose of sumatriptan tablets ranging from 140 to 300 mg without obvious adverse reactions. In another trial, 174 volunteers took a single dose of sumatriptan tablets ranging from 140 to 400 mg, and no serious adverse reactions were found. If a patient takes an overdose of this product, he should be observed for at least 12 hours or until the symptoms disappear. It is not clear what effect hemodialysis or peritoneal dialysis has on the plasma concentration of sumatriptan.
Specifications	50mg (calculated as C14H21N3O2S)
Manufacturer	Hunan Jiudian Pharmaceutical Co., Ltd.

Sumatriptan succinate tablets
Ingredients	Chemical name: 3-[2-(dimethylamino)ethyl]-N-methylindole-5-methanesulfonamide succinate. Chemical structure: Molecular formula: C14H21N3O2SC4H6O4 Molecular weight: 413.49
Indication	Drugs containing ergotamine may exacerbate vasospastic reactions. Theoretically, the simultaneous use of ergotamine-containing drugs or ergotamine-like drugs (such as dihydroergotamine or dihydroergonovine) within 24 hours can make this reaction worse, so it should be avoided. For patients taking monoamine oxidase inhibitors, taking the recommended dose of sumatriptan at the same time, the blood concentration can reach 7 times that of taking the same dose of sumatriptan alone. Therefore, the two are prohibited from being used in combination. There are reports that selective serotonin uptake inhibitors (SSRIS) (such as fluoxetine, FLUVOXAMINE, paroxetine, sertraline) occasionally cause weakness, hyperreflexia and ataxia when used in combination with sumatriptan. If it must be used in combination, it is recommended that the patient be properly observed. [Overdose] In a trial, 670 patients took a single dose of sumatriptan tablets ranging from 140 to 300 mg without obvious adverse reactions. In another trial, 174 volunteers took a single dose of sumatriptan tablets ranging from 140 to 400 mg, and no serious adverse reactions were found. If a patient takes an overdose of this product, he should be observed for at least 12 hours or until the symptoms disappear. It is not clear what effect hemodialysis or peritoneal dialysis has on the plasma concentration of sumatriptan.
Specifications	25mg (calculated as C14H21N3O2S)
Manufacturer	Hainan Simcere Pharmaceutical Co., Ltd.

Sumatriptan succinate tablets
Ingredients	Chemical name: 3-[2-(dimethylamino)ethyl]-N-methylindole-5-methanesulfonamide succinate. Chemical structure: Molecular formula: C14H21N3O2SC4H6O4 Molecular weight: 413.49
Indication	Drugs containing ergotamine may exacerbate vasospastic reactions. Theoretically, the simultaneous use of ergotamine-containing drugs or ergotamine-like drugs (such as dihydroergotamine or dihydroergonovine) within 24 hours can make this reaction worse, so it should be avoided. For patients taking monoamine oxidase inhibitors, taking the recommended dose of sumatriptan at the same time, the blood concentration can reach 7 times that of taking the same dose of sumatriptan alone. Therefore, the two are prohibited from being used in combination. There are reports that selective serotonin uptake inhibitors (SSRIS) (such as fluoxetine, FLUVOXAMINE, paroxetine, sertraline) occasionally cause weakness, hyperreflexia and ataxia when used in combination with sumatriptan. If it must be used in combination, it is recommended that the patient be properly observed. [Overdose] In a trial, 670 patients took a single dose of sumatriptan tablets ranging from 140 to 300 mg without obvious adverse reactions. In another trial, 174 volunteers took a single dose of sumatriptan tablets ranging from 140 to 400 mg, and no serious adverse reactions were found. If a patient takes an overdose of this product, he should be observed for at least 12 hours or until the symptoms disappear. It is not clear what effect hemodialysis or peritoneal dialysis has on the plasma concentration of sumatriptan.
Specifications	100mg (as sumatriptan)
Manufacturer	Tianjin Huajin Pharmaceutcial Co., Ltd.

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