Basic information
- CAS
103628-48-4- Standard SMILES
CNS(=O)(=O)Cc1ccc2[nH]cc(CCN(C)C)c2c1.O=C(O)CCC(=O)O- InChIKey
PORMUFZNYQJOEI-UHFFFAOYSA-N- Molecular formula
- C18H27N3O6S
- Average molar mass
- 413.5 g/mol
- Monoisotopic mass
- 413.16205676
Names & identifiers
- Preferred name
- Sumatriptan Succinate
- IUPAC
- butanedioic acid;1-[3-[2-(dimethylamino)ethyl]-1H-indol-5-yl]-N-methylmethanesulfonamide
- English name
- Sumatriptan succinate
- Molecular formula
- C18H27N3O6S
- Molecular weight
- 413.48848
Names & synonyms
Show more names
Database identifiers
- CAS
103628-48-4- PubChem CID
- 59772
- DTXSID
DTXSID60145966- ChEMBL
CHEMBL1201150- ChEBI
CHEBI:64359- UNII
- J8BDZ68989
- EC Number
- 600-463-4
Properties
Computed structural properties
- Topological polar surface area
- 148 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 8
- Rotatable bonds
- 9
- Heavy atoms
- 28
- Formal charge
- 0
- Complexity
- 498
Physicochemical properties
- Melting point
- 165 · 165-166°C
- storage temp.
- -20 °C · -20°C
- solubility
- 2 O: · H2O: >20mg/mL
- form
- solid
- color
- white to off-white
- Merck
- 14 · 14,8997
- BCS Class
- 3 · 3
- Major Application
- pharmaceutical (small molecule)
- InChI
- 1S/C14H21N3O2S.C4H6O4/c1-15-20(18,19)10-11-4-5-14-13(8-11)12(9-16-14)6-7-17(2)3;5-3(6)1-2-4(7)8/h4-5,8-9,15-16H,6-7,10H2,1-3H3;1-2H2,(H,5,6)(H,7,8)
- InChIKey
- PORMUFZNYQJOEI-UHFFFAOYSA-N
- SMILES
- OC(=O)CCC(O)=O.CNS(=O)(=O)Cc1ccc2[nH]cc(CCN(C)C)c2c1
- CAS DataBase Reference
- 103628 · 103628-48-4(CAS DataBase Reference)
- FDA UNII
- 8 BDZ68989 · J8BDZ68989
- NCI Drug Dictionary
- sumatriptan succinate
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 8 · GHS08
- Signal word
- Warning
- Hazard statements
- 361 d-H412 · H361d-H412
- Precautionary statements
- 202 · P202-P273-P280-P308+P313-P405-P501
- Hazard Codes
- Xi
- Risk Statements
- 36 · 36/37/38-41
- Safety Statements
- 26 · 26-36-39
- RIDADR
- 3077 · 3077
- WGK Germany
- 3 · 3
- RTECS
- 9940000 · EJ9940000
- HS Code
- 29350090 · 29350090
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 3 Repr · Aquatic Chronic 3Repr. 2
Safety & regulation
GHS classification
GHS Classification
Danger
H318 (79.6%): Causes serious eye damage [Danger Serious eye damage/eye irritation];H361 (13%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity];H412 (16.7%): Harmful to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]
P203, P264+P265, P273, P280, P305+P354+P338, P317, P318, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 54 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.
Hazard information
Toxicology
Toxicity Summary
The 5-HT<sub>1B</sub> and 5-HT<sub>1D</sub> receptors function as autoreceptors, which inhibit the firing of serotonin neurons and a reduction in the synthesis and release of serotonin upon activation. After sumatriptan binds to these receptors, adenylate cyclase activity is inhibited via regulatory G proteins, incrases intracellular calcium, and affects other intracellular events. This results in vasoconstriction and inhibtion of sensory nociceptive (trigeminal) nerve firing and vasoactive neuropeptide release. Sumatriptan stimulates 5-HT receptors of the 1D subtype, most likely presynaptic receptors, resulting in selective vasoconstriction of inflamed and dilated cranial blood vessels in the carotid circulation. Sumatriptan also blocks the release of vasoactive neuropeptides from perivascular trigeminal axons in the dura mater during migraine and may inhibit the release of inflammatory mediators from the trigeminal nerve.
Drug Induced Liver Injury
Drug Induced Liver Injury Rank (DILIrank 2.0)
Sumatriptan succinate
Ambiguous-DILI-concern
3
Adverse reactions
DOI:10.1016/j.drudis.2016.02.015
Effects During Pregnancy and Lactation
◉ Summary of Use during Lactation;Because of the low levels of sumatriptan in breastmilk, amounts ingested by the infant are small. It also has poor oral bioavailability, further decreasing infant exposure to the drug. Some authors have suggested that withholding breastfeeding for 8 hours after a single subcutaneous injection would virtually eliminate infant exposure to the drug. The manufacturer recommends withholding breastfeeding for 12 hours after a dose. Withholding breastfeeding might be helpful in extreme cases, such as in the mother of a preterm infant, but sumatriptan would not be expected to cause any adverse effects in most breastfed infants and has been recommended as a triptan of choice in breastfeeding. Painful, burning nipples and breast pain have been reported after doses of sumatriptan and other triptans. This has occasionally been accompanied by a decrease in milk production.;◉ Effects in Breastfed Infants;One author reported correspondence with the drug's manufacturer stating that of 3 women known to the manufacturer who used sumatriptan (dose and route unspecified) during breastfeeding none reported adverse effects on the infants.;◉ Effects on Lactation and Breastmilk;One author reported correspondence with the drug's manufacturer stating that 1 woman who used a single injection of sumatriptan (dose unspecified) during breastfeeding had a cessation of lactation.;A review of four European adverse reaction databases found 26 reported cases of painful, burning nipples, painful breasts, breast engorgement and/or painful milk ejection in women who took a triptan while nursing. Pain was sometimes intense and occasionally led to decreased milk production. Pain generally subsided with time as the drug was eliminated. The authors proposed that triptans may cause vasoconstriction of the arteries in the breast, nipples, and the arteries surrounding the alveoli and milk ducts, causing a painful sensation and a painful milk ejection reflex.
Regulatory information
Safety data
- wgk
- 3
- rtecs
- EJ9940000
- ridadr
- 3077
- hs_code
- 29350090
- risk_code
- 36/37/38-41
- Signal word
- Warning
- Symbol(GHS)
- GHS08
- hazard_code
- Xi
- safety_code
- 26-36-39
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H361d-H412
- Hazard Classifications
- Aquatic Chronic 3Repr. 2
- Precautionary statements
- P202-P273-P280-P308+P313-P405-P501
Chemistry & industry
Pharmacology
Metabolism/Metabolites
Hepatic. In vitro studies with human microsomes suggest that sumatriptan is metabolized by monoamine oxidase (MAO), predominantly the A isoenzyme. Route of Elimination: Only 3% of the dose is excreted in the urine as unchanged sumatriptan; 42% of the dose is excreted as the major metabolite, the indole acetic acid analogue of sumatriptan. Half Life: 2.5 hours
FDA Pharmacological Classification
SUMATRIPTAN SUCCINATE
Serotonin 1d Receptor Agonists [MoA]; Serotonin-1b and Serotonin-1d Receptor Agonist [EPC]; Serotonin 1b Receptor Agonists [MoA]
MeSH Pharmacological Classification
Drugs used to cause constriction of the blood vessels.
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.
Uses & manufacturing
Applications
DescriptionSumatriptan 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.
DescriptionSumatriptan 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.
UsesA serotonin 5HT1-receptor agonist
UsesH1-antihistamine
UsesA selective 5-HT1 receptor agonist
UsesSumatriptan (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.
UsesSumatriptan Succinate is a selective 5-HT1B/1D-receptor agonist with anticonvulsant properties (1,2). Sumatriptan Succinate is used for migraine relief (2).
Preparation methods
PreparationMethod 1: Using 4-hydrazino-N-methylbenzylsulfonamide hydrochloride and 4,4-dimethoxy-N,N-dimethyl-butylamine as starting materials, polyphosphoric acid and sodium dihydrogen phosphate were used as catalysts. The post-treatment employed isopropyl ether and acetone as recrystallization solvents. Sumatriptan succinate was synthesized through a four-step reaction involving condensation, rearrangement, cyclization, and salt formation, with an overall yield of 12.7%. Method 2: 1. Sodium 4-chlorobutane-1,1-disulfonate was prepared by reacting 4-chlorobutanal with an aqueous solution of sodium metabisulfite, followed by filtration and drying. 2. 4-hydrazino-N-methylbenzylsulfonamide hydrochloride and sodium 4-chlorobutane-1,1-disulfonate were reacted under heating in the presence of an inorganic or organic acid catalyst. The reaction solution was adjusted to neutral with an alkaline solution, and the mixture was extracted with an organic solvent to obtain 3-(2-chloroethyl)-N-methyl-1H-indole-5-methanesulfonamide. 3,3-(2-chloroethyl)-N-methyl-1H-indole-5-methanesulfonamide was used as a phase transfer catalyst to react with dimethylamine. After the reaction was completed, the product was extracted, decolorized and purified to obtain a high-quality sumatriptan. The product was then dissolved in a solvent by heating, and succinic acid was added to form a salt. After crystallization, a white final product, sumatriptan succinate, was obtained.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers100 total
Additional notes
DefinitionChEBI: 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.
Related reactions
Compound notes
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