95-25-0O=c1[nH]c2cc(Cl)ccc2o1TZFWDZFKRBELIQ-UHFFFAOYSA-NChlorzoxazone is 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 muscle spasm. It has a role as a sedative and a muscle relaxant. It is an organochlorine compound, a member of 1,3-benzoxazoles and a heteroaryl hydroxy compound.
95-25-0DTXSID9022813CHEMBL13711.6
2.11
2.96e+00 g/L
>25.4 [ug/mL] (The mean of the results at pH 7.4)
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Pharmaceuticals
191-191.5
191.5 °C
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Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 54 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
There have been no adequate prospective studies demonstrating the rates ofALT or AST elevations on chlorzoxazone therapy. Rare instances of clinicalapparent liver disease due to chlorzoxazone have appeared, including fatalcases. While case reports have been few, in many instances chlorzoxazone wasclearly implicated; furthermore, a related muscle relaxant with similarstructure (zoxazolamine) was withdrawn from use in 1961, largely because ofhepatotoxicity. The usual latency period to onset of liver injury is 1 to 4weeks, and the pattern of disease is typically hepatocellular with markedelevations in ALT levels and jaundice, but minimal increases in alkalinephosphatase. Cholestatic enzyme elevations after exposure to chlorzoxazonehave also been described. Allergic manifestations (rash and fever) arecommon, particularly in cases with a short latency (Case 1); autoantibodiesare rare. Recovery is rapid once chlorzoxazone is stopped, but fatal caseshave been reported, with disease progression despite early discontinuationof the agent (Case 2). There is rapid recurrence of injury with reexposure,often accompanied by fever.
M - Musculo-skeletal system
QM - Musculo-skeletal system
Chlorzoxazone is a centrally-acting agent for painful musculoskeletal conditions. Data available from animal experiments as well as human study indicate that chlorzoxazone acts primarily at the level of the spinal cord and subcortical areas of the brain where it inhibits multisynaptic reflex a.c. involved in producing and maintaining skeletal muscle spasm of varied etiology. The clinical result is a reduction of the skeletal muscle spasm with relief of pain and increased mobility of the involved muscles.
Chlorzoxazone inhibits degranulation of mast cells, subsequently preventing the release of histamine and slow-reacting substance of anaphylaxis (SRS-A), mediators of type I allergic reactions. Chlorzoxazone also may reduce the release of inflammatory leukotrienes. Chlorzoxazone may act by inhibiting calcium and potassium influx which would lead to neuronal inhibition and muscle relaxation. Data available from animal experiments as well as human study indicate that chlorzoxazone acts primarily at the level of the spinal cord and subcortical areas of the brain where it inhibits multisynaptic reflex arcs involved in producing and maintaining skeletal muscle spasm
Chlorzoxazone is rapidly metabolized in the liver and is excreted in the urine, primarily in a conjugated form as the glucuronide.
Chlorzoxazone has known human metabolites that include 6-Hydroxychlorzoxazone.
H0DE420U8G
CHLORZOXAZONE
Physiologic Effects [PE] - Centrally-mediated Muscle Relaxation
Established Pharmacologic Class [EPC] - Muscle Relaxant
Chlorzoxazone is a Muscle Relaxant. The physiologic effect of chlorzoxazone is by means of Centrally-mediated Muscle Relaxation.
CHLORZOXAZONE
불러오는 중…
CHEBI:3655White to Off-White Solid
Drug Induced Liver Injury Rank (DILIrank 2.0)
Chlorzoxazone
vMost-DILI-concern
8
Warnings & precautions
DOI:10.1016/j.drudis.2016.02.015
A heterogeneous group of drugs used to produce muscle relaxation, excepting the neuromuscular blocking agents. They have their primary clinical and therapeutic uses in the treatment of muscle spasm and immobility associated with strains, sprains, and injuries of the back and, to a lesser degree, injuries to the neck. They have been used also for the treatment of a variety of clinical conditions that have in common only the presence of skeletal muscle hyperactivity, for example, the muscle spasms that can occur in MULTIPLE SCLEROSIS. (From Smith and Reynard, Textbook of Pharmacology, 1991, p358)
개요Chlorzoxazone 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.).
용도Chlorzoxazone 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.
일반 설명Chlorzoxazone 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.
정의ChEBI: 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.