CAS 97240-79-4|Topiramate

Introduction：Basic information about CAS 97240-79-4|Topiramate, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Topiramate BiologicalActivity
3. Chemical & Physical Properties
4. Toxicological Information
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
5. Safety Information
6. Articles54
7. Synonyms

Common Name	Topiramate
CAS Number	97240-79-4	Molecular Weight	339.362
Density	1.3±0.1 g/cm3	Boiling Point	438.7±55.0 °C at 760 mmHg
Molecular Formula	C₁₂H₂₁NO₈S	Melting Point	125ºC
MSDS	ChineseUSA	Flash Point	219.1±31.5 °C
Symbol	GHS02, GHS06, GHS08	Signal Word	Danger

Names

Name	topiramate
Synonym	More Synonyms

Topiramate BiologicalActivity

Description	Topiramate is an anticonvulsant that antagonizes GluR5 receptors and acts as a positive allosteric modulator of GABA receptor-mediated currents.Target: GluR5 receptor; GABA receptorTopiramate (Topamax) is a structurally novel broad-spectrum antiepileptic drug (AED) with established efficacy as monotherapy or adjunctive therapy in the treatment of adult and paediatric patients with generalised tonic-clonic seizures, partial seizures with or without generalised seizures, and seizures associated with Lennox-Gastaut syndrome [1]. topiramate has been believed to be a type of antiepileptic drug that blocks spread of seizures. Thus far, the mechanisms of its actions have been proven to include use-dependent inhibition of voltage-dependent Na+ channels in neurons, potentiation of GABA (gamma-amino-butyric acid)-induced Cl- influx, and inhibitory effects on inward currents by antagonizing kainate/alpha-amino-3-hydroxy-5-methylisoxazole-4-propionic acid (AMPA) receptors [2].Topiramate (median average dosage 5.1 mg/kg/day) was also found to be useful as adjunctive therapy in the management of Lennox-Gastaut syndrome and significantly reduced the mean frequency of drop attacks by 14.8% compared with an increase of 5.1% with placebo. Further gains in seizure control were made in a nonblind extension of this trial where the mean topiramate dosage was 10 mg/kg/day. Nine of 11 patients in 1 pilot trial of children with otherwise intractable West syndrome, and 5 of 10 in another, achieved a > or =50% reduction in seizure rate with topiramate (target dosage up to 24 mg/kg/day) [3].Clinical indications: Epilepsy; Lennox Gastaut syndrome; Migraine; Seizure disorder Toxicity:abdominal pain; agitation; blurred vision; convulsions; depression; dizziness; double vision; drowsiness; impaired coordination; impaired mental activity; low blood pressure; reduced consciousness; severe diarrhea; sluggishness and speech problems.
Related Catalog	Signaling Pathways >>GPCR/G Protein >>mGluRResearch Areas >>Neurological Disease
References	[1]. Lyseng-Williamson KA, et al. Topiramate: a review of its use in the treatment of epilepsy. Drugs. 2007;67(15):2231-56. [2]. Nakamura J, et al. Target pharmacology of topiramate, a new antiepileptic drug. Nihon Yakurigaku Zasshi. 2000 Jan;115(1):53-7. [3]. Ormrod D, et al. Topiramate: a review of its use in childhood epilepsy. Paediatr Drugs. 2001;3(4):293-319.

Description

Topiramate is an anticonvulsant that antagonizes GluR5 receptors and acts as a positive allosteric modulator of GABA receptor-mediated currents.Target: GluR5 receptor; GABA receptorTopiramate (Topamax) is a structurally novel broad-spectrum antiepileptic drug (AED) with established efficacy as monotherapy or adjunctive therapy in the treatment of adult and paediatric patients with generalised tonic-clonic seizures, partial seizures with or without generalised seizures, and seizures associated with Lennox-Gastaut syndrome [1]. topiramate has been believed to be a type of antiepileptic drug that blocks spread of seizures. Thus far, the mechanisms of its actions have been proven to include use-dependent inhibition of voltage-dependent Na+ channels in neurons, potentiation of GABA (gamma-amino-butyric acid)-induced Cl- influx, and inhibitory effects on inward currents by antagonizing kainate/alpha-amino-3-hydroxy-5-methylisoxazole-4-propionic acid (AMPA) receptors [2].Topiramate (median average dosage 5.1 mg/kg/day) was also found to be useful as adjunctive therapy in the management of Lennox-Gastaut syndrome and significantly reduced the mean frequency of drop attacks by 14.8% compared with an increase of 5.1% with placebo. Further gains in seizure control were made in a nonblind extension of this trial where the mean topiramate dosage was 10 mg/kg/day. Nine of 11 patients in 1 pilot trial of children with otherwise intractable West syndrome, and 5 of 10 in another, achieved a > or =50% reduction in seizure rate with topiramate (target dosage up to 24 mg/kg/day) [3].Clinical indications: Epilepsy; Lennox Gastaut syndrome; Migraine; Seizure disorder Toxicity:abdominal pain; agitation; blurred vision; convulsions; depression; dizziness; double vision; drowsiness; impaired coordination; impaired mental activity; low blood pressure; reduced consciousness; severe diarrhea; sluggishness and speech problems.

Related Catalog

Signaling Pathways >>GPCR/G Protein >>mGluRResearch Areas >>Neurological Disease

References

[1]. Lyseng-Williamson KA, et al. Topiramate: a review of its use in the treatment of epilepsy. Drugs. 2007;67(15):2231-56.

[2]. Nakamura J, et al. Target pharmacology of topiramate, a new antiepileptic drug. Nihon Yakurigaku Zasshi. 2000 Jan;115(1):53-7.

[3]. Ormrod D, et al. Topiramate: a review of its use in childhood epilepsy. Paediatr Drugs. 2001;3(4):293-319.

Chemical & Physical Properties

Density	1.3±0.1 g/cm3
Boiling Point	438.7±55.0 °C at 760 mmHg
Melting Point	125ºC
Molecular Formula	C₁₂H₂₁NO₈S
Molecular Weight	339.362
Flash Point	219.1±31.5 °C
Exact Mass	339.098785
PSA	123.92000
LogP	2.97
Vapour Pressure	0.0±1.1 mmHg at 25°C
Index of Refraction	1.497
InChIKey	KJADKKWYZYXHBB-XBWDGYHZSA-N
SMILES	CC1(C)OC2COC3(COS(N)(=O)=O)OC(C)(C)OC3C2O1

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: LS7083000

CAS REGISTRY NUMBER :: 97240-79-4

LAST UPDATED :: 199612

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C12-H21-N-O8-S

MOLECULAR WEIGHT :: 339.40

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >1500 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: DRFUD4 Drugs of the Future. (J.R. Prous, S.A., Apartado de Correos 540, 08080 Barcelona, Spain) V.1- 1975/76- Volume(issue)/page/year: 14,342,1989

Safety Information

Symbol	GHS02, GHS06, GHS08
Signal Word	Danger
Hazard Statements	H225-H301 + H311 + H331-H370
Precautionary Statements	P210-P260-P280-P301 + P310-P311
Personal Protective Equipment	dust mask type N95 (US);Eyeshields;Gloves
Hazard Codes	Xn: Harmful;
Risk Phrases	R36/37/38
Safety Phrases	26-36
RIDADR	UN1230 - class 3 - PG 2 - Methanol, solution
WGK Germany	3
RTECS	LS7083000

Articles54

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Synonyms

Topamax Sprinkle

2,3:4,5-Bis-O-(1-methylethylidene)-b-D-fructopyranose sulfamate

Topiramate

Topimax

Tipiramato [Spanish]

Epitomax

McN-4853

topiramatum [Latin]

topiramatum

Tipiramate [French]

[(3aS,5aR,8aR,8bS)-2,2,7,7-tetramethyl-5,5a,8a,8b-tetrahydrodi[1,3]dioxolo[4,5-a:5',3'-d]pyran-3a-yl]methyl sulfamate

Tipiramate

[(3aS,5aR,8aR,8bS)-2,2,7,7-Tetramethyltetrahydro-3aH-bis[1,3]dioxolo[4,5-b:4',5'-d]pyran-3a-yl]methyl sulfamate

RWJ 17021-000

Topamax

Topomax

Topiramato [INN-Spanish]

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