Rizatriptan benzoate

Bezeichnung:Rizatriptan benzoate

CAS-Nr145202-66-0

Englisch Name:Rizatriptan benzoate

CBNumberCB4100441

SummenformelC22H25N5O2

Molgewicht391.48

MOL-Datei145202-66-0.mol

Rizatriptan benzoate physikalisch-chemischer Eigenschaften

Schmelzpunkt	178-180°C
storage temp.	2-8°C
Löslichkeit	H2O: ≥5mg/mL
Aggregatzustand	powder
Farbe	white to beige
Wasserlöslichkeit	H2O: ≥5mg/mL
Merck	14,8241
InChI	InChI=1S/C15H19N5.C7H6O2/c1-19(2)6-5-13-8-17-15-4-3-12(7-14(13)15)9-20-11-16-10-18-20;8-7(9)6-4-2-1-3-5-6/h3-4,7-8,10-11,17H,5-6,9H2,1-2H3;1-5H,(H,8,9)
InChIKey	JPRXYLQNJJVCMZ-UHFFFAOYSA-N
SMILES	C(C1C=CC=CC=1)(=O)O.C(C1=CNC2C=CC(CN3N=CN=C3)=CC1=2)CN(C)C
CAS Datenbank	145202-66-0(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	T
R-Sätze:	61
WGK Germany	3
HS Code	2933995500
Speicherklasse	6.1C - Combustible acute toxic Cat.3 toxic compounds or compounds which causing chronic effects
Hazard Classifications	Repr. 1B

Gefahreninformationscode (GHS)

Rizatriptan benzoate Chemische Eigenschaften,Einsatz,Produktion Methoden

Beschreibung
Rizatriptan was launched for the first time as Maxalt in Mexico for the acute treatment of migraine headaches with or without aura in adults. It is the third in a new generation of triptan migraine drugs to challenge the firstgeneration product Sumatriptan from Glaxo Wellcome, after Zolmitriptan (Zeneca) and Naratriptan (Glaxo Wellcome).
It can be synthetically obtained by two related routes having respectively 3 and 4 steps, both starting from 1 -(4-aminobenzyl)-l,2,4-triazole. Rizatriptan is a full 5-HT1D/1B receptor agonist retaining a significant affinity at 5-HT1A sites (pIC50 = 6.4), with a low affinity for nond-HT sites. It shows craniovascufar selectivity for human isolated middle meningeal over coronary arteries ; its effect on coronary artery constriction is significantly less than that for Sumatriptan. Rizatriptan inhibits the release of neuropeptides that cause swelling of cranial blood vessels. Rizatriptan has a good oral bioavailability (64% and 47% in rats and dogs respectively). and a rapid onset of action : the headache relief in human occurs within 30 to 45 minutes of taking 20 mg. It also relieved nausea and hypersensitivity to noise (phonophobia) and light (photophobia) that are often symptoms accompanying a migraine attack. Among at least 6 metabolites identified in humans after a single oral dose (60 mg), the major urinary metabolite was the corresponding indole-3-acetic acid. Maxalt is available as a novel oral formulation of rapidly dissolving tablets or wafers that does not require liquid for ingestion.
Chemische Eigenschaften
Off-White Solid
Originator
Merck & Co (US)
Verwenden
Rizatriptan Benzoate(Maxalt) is a 5-HT1 agonist triptan drug for the treatment of migraine headaches. It is believed to work by narrowing the blood vessels around the brain. Rizatriptan also reduces the substances in the body, which can also reduce headac
Verwenden
A selective serotonin 5-HTID receptor agonist. Structurally derived from tryptamine
Verwenden
Rizatriptan Benzoate is a selective serotonin 5-HTID receptor agonist and used to treat migraine (1,2,3). It is structurally derived from tryptamine.
Definition
ChEBI: Rizatriptan benzoate is a member of tryptamines.
Trademarks
Maxalt (Merck).
Allgemeine Beschreibung
Pharmaceutical secondary standards for application in quality control provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards
Biochem/physiol Actions
Rizatriptan is a serotonin 5HT-1B/1D-receptor agonist used to treat migraine.
Synthese
A method for the preparation of rizatriptan benzoate, characterized in that it is carried out in the following steps: using 4-chlorobutanal as a raw material, and reacting with sodium metabisulfite in an addition reaction to obtain sodium 4-chlorobutane-1,1-disulfonate; reacting sodium 4-chlorobutane-1,1-disulfonate with 1-(4-hydrazinylphenyl)methyl-1,2,4-triazole hydrochloride in a mixed solution of alcohol-water in the presence of a catalyst After that, 3-(2-chloroethyl)-5-(1H-1,2,4-triazol-1-ylmethyl)-1H-indole was obtained by alkali neutralization and concentration by solvent extraction; (iii) 3-(2-chloroethyl)-5-(1H-1,2,4-triazol-1-ylmethyl)-1H-indole was reacted with dimethylamine, and rizatriptan was obtained by the action of a phase-transferring catalyst; (iv) Rizatriptan and benzoic acid were salted in a solvent to form a salt of rizatriptan benzoate, and then refined with ethanol to obtain rizatriptan benzoate boutique.

Rizatriptan benzoate Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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