クロルゾキサゾン
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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/07/24 11:07:10」(JST)
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Chlorzoxazone
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| Systematic (IUPAC) name |
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5-chloro-3H-benzooxazol-2-one
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| Clinical data |
| Trade names |
Parafonforte |
| AHFS/Drugs.com |
monograph |
| MedlinePlus |
a682577 |
Routes of
administration |
oral |
| Pharmacokinetic data |
| Bioavailability |
well absorbed |
| Protein binding |
13–18% |
| Metabolism |
hepatic |
| Biological half-life |
1.1 hr |
| Excretion |
urine (<1%) |
| Identifiers |
| CAS Registry Number |
95-25-0 Y |
| ATC code |
M03BB03 |
| PubChem |
CID: 2733 |
| IUPHAR/BPS |
2322 |
| DrugBank |
DB00356 Y |
| ChemSpider |
2632 Y |
| UNII |
H0DE420U8G Y |
| KEGG |
D00771 Y |
| ChEBI |
CHEBI:3655 Y |
| ChEMBL |
CHEMBL1371 Y |
| Chemical data |
| Formula |
C7H4ClNO2 |
| Molecular mass |
169.565 g/mol |
|
|
InChI
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InChI=1S/C7H4ClNO2/c8-4-1-2-6-5(3-4)9-7(10)11-6/h1-3H,(H,9,10) Y
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Key:TZFWDZFKRBELIQ-UHFFFAOYSA-N Y
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| Y (what is this?) (verify) |
Chlorzoxazone (Paraflex) is a centrally acting muscle relaxant used to treat muscle spasm and the resulting pain or discomfort. It acts on the spinal cord by depressing reflexes. It is sold as Muscol or Parafon Forte, a combination of chlorzoxazone and acetaminophen (Paracetamol). Possible side effects include dizziness, lightheadedness, malaise, nausea, vomiting, and liver dysfunction. Used with acetaminophen it has added risk of hepatoxicity,[medical citation needed] which is why the combination is not recommended. It can also be administered for acute pain in general and for tension headache (muscle contraction headache).
Synthesis
Chlorzoxazone synthesis: Mcneilab Inc, David F Marsh.
U.S. Patent 2,895,877
Chlorzoxazone, 5-chloro-2-benzoxazolione, is synthesized by a hetercyclization reaction of 2-amino-4-chlorophenol with phosgene.
References
- D.F. Marsh, U.S. Patent 2,895,877 (1959).
- Dong DL, Luan Y, Feng TM, Fan CL, Yue P, Sun ZJ, Gu RM, Yang BF. (2006). "Chlorzoxazone inhibit contraction of rat thoracic aorta". Eur J Pharmacol 545 (2–3): 161–6. doi:10.1016/j.ejphar.2006.06.063. PMID 16859676.
- Park J, Kim K, Park P, Ha J (2006). "Effect of high-dose aspirin on CYP2E1 activity in healthy subjects measured using chlorzoxazone as a probe". J Clin Pharmacol 46 (1): 109–14. doi:10.1177/0091270005282635. PMID 16397290.
- Wan J, Ernstgård L, Song B, Shoaf S (2006). "Chlorzoxazone metabolism is increased in fasted Sprague-Dawley rats". J Pharm Pharmacol 58 (1): 51–61. doi:10.1211/jpp.58.1.0007. PMC 1388188. PMID 16393464.
- PARAFON DSC (chlorzoxazone) tablet, Daily Med, U.S. National Library of Medicine
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Skeletal muscle relaxants (M03)
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Peripherally acting
(primarily antinicotinic,
NMJ block) |
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Non-depolarizing
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Curare alkaloids
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- Alcuronium
- Dimethyltubocurarine
- Tubocurarine
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|
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4° ammonium agents
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- ultra-short duration: Gantacurium
- short duration: Mivacurium
- Chandonium
- intermediate duration: Atracurium
- Cisatracurium
- Fazadinium
- Rocuronium
- Vecuronium
- long duration: Doxacurium
- Dimethyltubocurarine
- Pancuronium
- Pipecuronium
- Laudexium
- Gallamine
- unsorted: Hexafluronium (Hexafluorenium)
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Depolarizing
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- Choline derivatives: Suxamethonium (Succinylcholine)
- Polyalkylene derivatives: Hexamethonium
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ACh release inhibitors
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|
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| Centrally acting |
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Carbamic acid esters
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- Carisoprodol
- Cyclarbamate
- Difebarbamate
- Febarbamate
- Meprobamate
- Methocarbamol
- Phenprobamate
- Styramate
- Tybamate
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|
|
Benzodiazepines
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- Bromazepam
- Diazepam
- Clonazepam
- Flunitrazepam
- Lorazepam
- Nitrazepam
- Temazepam
- Tetrazepam
|
|
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Nonbenzodiazepines
|
|
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Thienodiazepines
|
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Quinazolines
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Anticholinergics
(Antimuscarinics)
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- Cyclobenzaprine
- Orphenadrine
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|
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Other
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- Arbaclofen placarbil
- Baclofen
- Chlormezanone
- Chlorphenesin
- Chlorzoxazone
- Donepezil
- Eperisone
- Fenyramidol
- Flopropione
- Gabapentin
- GHB
- Mephenesin
- Mephenoxalone
- Metaxalone
- Phenibut
- Pregabalin
- Pridinol
- Promoxolane
- Quinine
- Thiocolchicoside
- Tizanidine
- Tolperisone
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| Directly acting |
|
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Index of muscle
|
|
| Description |
- Anatomy
- head
- neck
- arms
- chest and back
- diaphragm
- abdomen
- genital area
- legs
- Muscle tissue
- Physiology
|
|
| Disease |
- Myopathy
- Soft tissue
- Connective tissue
- Congenital
- abdomen
- muscular dystrophy
- Neoplasms and cancer
- Injury
- Symptoms and signs
|
|
| Treatment |
- Procedures
- Drugs
- anti-inflammatory
- muscle relaxants
|
|
|
UpToDate Contents
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- 1. 急性腰痛の治療 treatment of acute low back pain
- 2. 律動眼振 jerk nystagmus
English Journal
- Stability-Indicating TLC-Densitometric Method for Simultaneous Determination of Paracetamol and Chlorzoxazone and their Toxic Impurities.
- Abdelaleem EA, Abdelwahab NS.SourcePharmaceutical Analytical Chemistry Department, Faculty of Pharmacy, Bani-Sueif University, Alshaheed Shehata Ahmad Hegazy St., 62514, Beni-Suef, Egypt.
- Journal of chromatographic science.J Chromatogr Sci.2012 Jul 26. [Epub ahead of print]
- A highly sensitive, selective and accurate thin-layer chromatographic (TLC)-densitometric method has been developed and validated for the simultaneous determination of paracetamol (PAR) and chlorzoxazone (CZ) and their toxic impurities, 4-amino phenol (4AP) and 2-amino-4-chlorophenol (2ACP), respect
- PMID 22843763
- Enzyme kinetic and molecular docking studies on the metabolic interactions of 1-hydroxy-2,3,5-trimethoxy-xanthone, isolated from Halenia elliptica D. Don, with model probe substrates of human cytochrome P450 enzymes.
- Feng R, Zhou X, Or PM, Ma JY, Tan XS, Fu J, Ma C, Shi JG, Che CT, Wang Y, Yeung JH.SourceState Key Laboratory of Bioactive Substances and Functions of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences, Beijing 100050, China.
- Phytomedicine : international journal of phytotherapy and phytopharmacology.Phytomedicine.2012 Jul 19. [Epub ahead of print]
- Halenia elliptica D. Don is a Tibetan herb and medicinal preparations containing Halenia elliptica have been commonly used for the treatment of hepatitis B virus infection in China. The metabolism of 1-hydroxy-2,3,5-trimethoxy-xanthone (HM-1) to its metabolites is mediated through cytochrome P450 en
- PMID 22819301
Japanese Journal
- Regulation of Cytochrome b5 Expression by miR-223 in Human Liver: Effects on Cytochrome P450 Activities
- Takahashi Kei,Oda Yuki,Toyoda Yasuyuki,Fukami Tatsuki,Yokoi Tsuyoshi,Nakajima Miki
- Pharmaceutical Research 31(3), 780-794, 2014-03
- … Moreover, the overexpression of miR-223 significantly reduced CYP3A4-catalyzed testosterone 6β-hydroxylation activity and CYP2E1-catalyzed chlorzoxazone 6-hydroxylase activity but not CYP1A2-catalyzed 7-ethoxyresorufin O-deethylase activity. …
- NAID 120005596360
- Cytochrome P450 Metabolic Activities in the Small Intestine of Cynomolgus Macaques Bred in Cambodia, China, and Indonesia
- , , , , , , , , , , ,
- Drug Metabolism and Pharmacokinetics 28(6), 510-513, 2013
- … In the present study, P450 metabolic activity was investigated in the small intestine of MacfaCAM and MacfaCHN, and cynomolgus macaques bred in Indonesia (MacfaIDN) using P450 substrates, including 7-ethoxyresorufin, coumarin, bupropion, paclitaxel, diclofenac, S-mephenytoin, bufuralol, chlorzoxazone, and testosterone. …
- NAID 130004463329
- Inhibitory effects of kale ingestion on metabolism by cytochrome P450 enzymes in rats
- , , , , ,
- Biomedical Research 33(4), 235-242, 2012
- … We investigated the effects of kale intake on cytochrome P450 (CYP) metabolism by using cocktail probe drugs, including midazolam (for CYP3A4), caffeine (for CYP1A2), dextromethorphan (for CYP2D6), tolbutamide (for CYP2C9), omeprazole (for CYP2C19), and chlorzoxazone (for CYP2E1). …
- NAID 130004470826
Related Links
- Chlorzoxazone may cause side effects. Your urine may turn purple or red; this effect is not harmful. Tell your doctor if any of these symptoms are severe or do not go away: upset stomach drowsiness dizziness
- Easy to read patient leaflet for chlorzoxazone. Includes indications, proper use, special instructions, precautions, and possible side effects. ... If OVERDOSE is suspected: Contact 1-800-222-1222 (the American Association of ...
Related Pictures
★リンクテーブル★
[★]
- 英
- chlorzoxazone
- ラ
- chlorzoxazonum
- 商
- スラックシン、Par flex, Parafon Forte
- 関
- 脊髄反射、骨格筋弛緩剤
中枢性筋弛緩薬