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a salt (or ester) of carbamic acid

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/10/30 23:49:41」(JST)

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Chlorphenesin carbamate (Maolate, Musil) is a centrally acting muscle relaxant used to treat muscle pain and spasms.^[1]^[2] Chlorphenesin is no longer used for this purpose in most developed nations due to the availability of much safer spasmolytics such as benzodiazepines.

Other central effects include sedation, anxiolysis, and dizziness. It also has antifungal and some antibacterial properties and is thus classified as an antifungal for topical use by the WHO.^[3]

Safety

The major adverse effect from this preservative on skin is allergic contact sensitivity.^[4]^[5] Systemic intoxication from transdermal use has not been observed, although the FDA discourages its use as an ingredient in nipple cream for nursing mothers.^[6]

References

^ Okuyama, S; Aihara, H (1987). "Antinociceptive effect of chlorphenesin carbamate in adjuvant arthritic rats". Research communications in chemical pathology and pharmacology 55 (2): 147–60. PMID 3823606.
^ Kurachi, M; Aihara, H (1984). "Effect of a muscle relaxant, chlorphenesin carbamate, on the spinal neurons of rats". Japanese journal of pharmacology 36 (1): 7–13. doi:10.1254/jjp.36.7. PMID 6503049.
^ ATC code D01AE07
^ Brown R (1981). "Chlorphenesin sensitivity". Contact Dermatitis 7 (3): 162. doi:10.1111/j.1600-0536.1981.tb04601.x. PMID 6456118.
^ Burns DA (1986). "Allergic contact sensitivity to chlorphenesin". Contact Dermatitis 14 (33): 246. doi:10.1111/j.1600-0536.1986.tb01234.x. PMID 2941223.
^ http://www.fda.gov/NewsEvents/Newsroom/PressAnnouncements/2008/ucm116900.htm. Missing or empty |title= (help)

UpToDate Contents

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1. 有機リン剤およびカルバメート中毒 organophosphate and carbamate poisoning
2. 神経筋接合部に作用する毒素の概要 overview of neuromuscular junction toxins
3. 筋力低下を呈する小児の病因および評価 etiology and evaluation of the child with muscle weakness
4. アレルギー性接触皮膚炎の一般的なアレルゲン common allergens in allergic contact dermatitis
5. 思春期におけるオピオイド離脱 opioid withdrawal in adolescents

English Journal

Synthesis of enantiomerically enriched drug precursors and an insect pheromone via reduction of ketones using commercially available carbonyl reductase screening kit "Chiralscreen® OH".

Nagai T1, Sakurai S1, Natori N1, Hataoka M2, Kinoshita T3, Inoue H4, Hanaya K1, Shoji M1, Sugai T5.
Bioorganic & medicinal chemistry.Bioorg Med Chem.2017 Apr 1. pii: S0968-0896(17)30084-6. doi: 10.1016/j.bmc.2017.03.067. [Epub ahead of print]
PMID 28506583

High-throughput and simultaneous analysis of eight central-acting muscle relaxants in human plasma by ultra-performance liquid chromatography-tandem mass spectrometry in the positive and negative ionization modes.

Ogawa T1, Hattori H, Kaneko R, Ito K, Iwai M, Mizutani Y, Arinobu T, Ishii A, Seno H.
Analytical and bioanalytical chemistry.Anal Bioanal Chem.2011 Jun;400(7):1959-65. doi: 10.1007/s00216-011-4860-3. Epub 2011 Mar 12.
PMID 21394449

Relative bioavailability of generic and branded 250-mg and 500-mg oral chlorphenesin carbamate tablets in healthy Korean volunteers: a single-dose, randomized-sequence, open-label, two-period crossover trial.

Yu JY1, Song HH, Kim BG, Park HJ, Choi KS, Kwon YE.
Clinical therapeutics.Clin Ther.2009 Nov;31(11):2735-43. doi: 10.1016/j.clinthera.2009.11.036.
PMID 20110015

Japanese Journal

Kinetics and Mechanism of Degradation of Chlorphenesin Carbamate in Strongly Acidic Aqueous Solutions

Chemical & pharmaceutical bulletin 34(8), 3481-3484, 1986-08-25
NAID 110003626567

Studies on the Kinetics and Mechanism of Drug Degradation. I. : Kinetics and Mechanism of Degradation of Chlorphenesin Carbamate in Strongly Alkaline Aqueous Solutions

Chemical & pharmaceutical bulletin 34(4), 1764-1769, 1986-04-25
NAID 110003626300

Kinetics and mechanism of degradation of chlorphenesin carbamate in strongly acidic aqueous solutions.

Chemical and Pharmaceutical Bulletin 34(8), 3481-3484, 1986
NAID 130003770842

「クロルフェネシン」

Chlorphenesin
Systematic (IUPAC) name
	(3-(4-chlorophenoxy)-2-hydroxypropyl)carbamate
Clinical data
AHFS/Drugs.com	Micromedex Detailed Consumer Information
Pharmacokinetic data
Excretion	urine
Identifiers
CAS Registry Number	886-74-8
ATC code	D01AE07
PubChem	CID: 2724
ChemSpider	2623
UNII	I670DAL4SZ
KEGG	D00770
ChEBI	CHEBI:3642
ChEMBL	CHEMBL607710
Chemical data
Formula	C10H12ClNO4
Molecular mass	245.660 g/mol
	SMILES c1cc(ccc1OCC(COC(=O)N)O)Cl ;
	InChI InChI=1S/C10H12ClNO4/c11-7-1-3-9(4-2-7)15-5-8(13)6-16-10(12)14/h1-4,8,13H,5-6H2,(H2,12,14) ; Key:SKPLBLUECSEIFO-UHFFFAOYSA-N ;
Physical data
Melting point	86 to 92 °C (187 to 198 °F)