Chlorzoxazon

Bezeichnung:Chlorzoxazon

CAS-Nr95-25-0

Englisch Name:Chlorzoxazone

CBNumberCB0392987

SummenformelC7H4ClNO2

Molgewicht169.57

MOL-Datei95-25-0.mol

Synonyma

Chlorzoxazon

Chlorzoxazon physikalisch-chemischer Eigenschaften

Schmelzpunkt	191-192 °C (lit.)
Dichte	1.3771 (rough estimate)
Brechungsindex	1.5557 (estimate)
storage temp.	room temp
Löslichkeit	DMSO: soluble50mg/mL, clear
pka	pKa 8.3 (Uncertain)
Aggregatzustand	Powder
Farbe	white to off-white
Wasserlöslichkeit	0.1 g/100 mL
Merck	14,2194
LogP	1.816 (est)
CAS Datenbank	95-25-0(CAS DataBase Reference)
NIST chemische Informationen	Chlorzoxazone(95-25-0)
EPA chemische Informationen	Chlorzoxazone (95-25-0)

Sicherheit

Kennzeichnung gefährlicher	Xn,T,Xi
R-Sätze:	22-36/37/38-20/21/22
S-Sätze:	26-36-24/25-37/39
WGK Germany	3
RTECS-Nr.	DM5250000
Hazard Note	Toxic/Irritant
TSCA	Yes
HazardClass	IRRITANT
HS Code	29349990
Toxizität	LD50 in mice (mg/kg): 3650 orally, 380 i.p. (suspensions); 440 orally, 183 i.p. (solns of Na salt) (Hofrichter)

Gefahreninformationscode (GHS)

Chlorzoxazone Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R22:Gesundheitsschädlich beim Verschlucken.
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
R20/21/22:Gesundheitsschädlich beim Einatmen,Verschlucken und Berührung mit der Haut.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
S24/25:Berührung mit den Augen und der Haut vermeiden.
S37/39:Bei der Arbeit geeignete Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
Beschreibung
Chlorzoxazone is a muscle relaxant. It acts by blocking nerve impulses or pain sensations that are sent to brain. Typically, it is used together with rest and physical therapy to treat skeletal muscle conditions such as pain or injury. Chlorzoxazone, 5-chloro-2-benzoxazolione, is synthesized by a heterocyclization reaction of 2-amino-4-chlorophenol with phosgene. Skeletal muscle relaxants have conventionally been classified into one group; however, they are actually a heterogeneous group of medications commonly used to treat two different types of underlying conditions – spasticity from upper motor neuron syndromes and muscular pain or spasms from peripheral musculoskeletal conditions. Medications classified as skeletal muscle relaxants are baclofen, carisoprodol, chlorzoxazone, cyclobenzaprine, dantrolene, metaxalone, methocarbamol, orphenadrine, and tizanidine. These drugs may impair mental and/or physical abilities required for driving vehicles. As a class, skeletal muscle relaxants have central nervous system (CNS)-related side effects: drowsiness, dizziness, decreased alertness, blurred vision, and ataxia. Their use has been associated with a twofold increase in the risk for motor vehicle crashes. Muscle relaxants are included in the ‘Beers List’ of potentially inappropriate medications in older adults. Most muscle relaxants are poorly tolerated by elderly patients because they cause anticholinergic adverse effects, sedation, and weakness. Although extremely uncommon, this compound may yield to idiosyncratic and unpredictable type of liver toxicity. The concomitant use of alcohol or other CNS depressants may have an additive effect. Individuals on chlorzoxazone containing drugs should be monitored for abnormal liver enzymes (e.g., aspartate transaminase (AST), alanine transaminase (ALT), alkaline phosphatase, bilirubin, etc.).
Beschreibung
Chlorzoxazone is a centrally acting muscle relaxant and activator of small and intermediate conductance calcium-activated potassium channels (EC₅₀s = 87 and 98 μM for K_Ca2.2 and K_Ca3.1, respectively). In vivo, chlorzoxazone (10 mg/kg) decreases alcohol but not water intake in a dose-dependent manner and reduces the propensity for rapid initial alcohol intake in rats with intermittent, but not continuous, access to alcohol. Formulations containing chlorzoxazone have been used in the treatment of pain and stiffness caused by muscle spasm. This product is also available as an analytical reference standard .
Beschreibung
Chlorzoxazone (Item No. 25826) is an analytical reference standard categorized as a skeletal muscle relaxant. This product is intended for analytical forensic applications. This product is also available as a general research tool .
Chemische Eigenschaften
White to Off-White Solid
Originator
Paraflex ,McNeil, US ,1958
Verwenden
For the relief of discomfort associated with acute painful musculoskeletal conditions.
Verwenden
Muscle relaxant (skeletal)
Verwenden
Chlorzoxazone is a benzoxazolone derivative that causes skeletal muscle relaxation and blocks spasticity in clinical studies. Chlorzoxazone enhances small and intermediate conductance calcium-activated potassium channels (EC50s = 87 and 98 μM for KCa2.2 and KCa3.1, respectively). The cytochrome P450 isoform CYP2E1 converts chlorzoxazone to 6-hydroxy chlorzoxazone . The urinary excretion of this 6-hydroxy metabolite is often used as a probe of CYP2E1 activity in studies of hepatotoxicity.
Definition
ChEBI: A member of the class of 1,3-benzoxazoles that is 1,3-benzoxazol-2-ol in which the hydrogen atom at position 5 is substituted by chlorine. A centrally acting muscle relaxant with sedative properties, it is used for the symptomatic treatment of painful mus le spasm.
Manufacturing Process
A solution of 16.9 g (0.1 mol) of 2-amino-5-chlorobenzoxazole in 200 ml of 1 N HCl is refluxed until precipitation is complete. The resulting solid is collected
by filtration, dissolved in 200 ml of 1 N NaOH and the solution extracted with 50 ml of ether. Acidification of the alkaline solution gives a precipitate which is purified by crystallization from acetone to give 2-hydroxy-5-chlorobenzoxazole melting at 191° to 191.5°C.
Trademarks
Paraflex (Ortho-McNeil).
Therapeutic Function
Muscle relaxant
Allgemeine Beschreibung
Chlorzoxazone is a centrally active muscle relaxant used to treat painful muscle spasms linked to musculoskeletal disorders, such as fibrositis, bursitis, myositis, spondylitis, etc.
Pharmaceutical secondary standard for application in quality control. Provides pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards.
Biochem/physiol Actions
Chlorzoxazone is a skeletal muscle relaxant.
Synthese
Chlorzoxazone, 5-chloro-2-benzoxazolione (15.3.15), is synthesized by a hetercyclization reaction of 2-amino-4-chlorphenol with phosgene.
Environmental Fate
Chlorzoxazone ismetabolized by the CYP1A2 and CYP2E1 microsomal enzymes to a toxic metabolite 6-hydroxychlorzoxazone.
Toxicity evaluation
Chlorzoxazone is a white to off-white solid. It is soluble in organic solvents such as ethanol, methanol, and dimethyl sulfoxide (DMSO).

Chlorzoxazone Upstream-Materialien And Downstream Produkte

Chlorzoxazon Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

95-25-0, Chlorzoxazone Verwandte Suche:

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