Chlorphenesin

Chlorphenesin
Clinical data

AHFS/Drugs.com	Micromedex Detailed Consumer Information
ATC code	D01AE07 (WHO)
Pharmacokinetic data
Excretion	urine
Identifiers
IUPAC name (3-(4-chlorophenoxy)-2-hydroxypropyl)carbamate
CAS Number	886-74-8
PubChem (CID)	2724
ChemSpider	2623
UNII	I670DAL4SZ^Y
KEGG	D00770
ChEBI	CHEBI:3642^Y
ChEMBL	CHEMBL607710^Y
ECHA InfoCard	100.002.902
Chemical and physical data
Formula	C₁₀H₁₂ClNO₄
Molar mass	245.660 g/mol
3D model (Jmol)	Interactive image
Melting point	86 to 92 °C (187 to 198 °F)
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

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.
↑ "FDA Warns Consumers Against Using Mommy's Bliss Nipple Cream Product can be harmful to nursing infants".

Antifungals (D01 and J02)

Wall/
membrane

Ergosterol
inhibitors

Azoles
(lanosterol 14
alpha-demethylase inhibitors)

Imidazoles	Topical: bifonazole^‡ butoconazole chlormidazole^‡ clotrimazole^# croconazole^‡ econazole fenticonazole^‡ flutrimazole isoconazole^‡ ketoconazole luliconazole miconazole^# neticonazole^‡ omoconazole^‡ oxiconazole sertaconazole sulconazole tioconazole Systemic: ketoconazole

Triazoles	Topical: efinaconazole fluconazole^# fosfluconazole terconazole Systemic: fluconazole^# hexaconazole^‡ isavuconazole itraconazole posaconazole voriconazole Unknown: albaconazole^‡ ravuconazole^†

Thiazoles	Topical: abafungin^‡

Polyene antimycotics
(ergosterol binding)

Topical: hamycin^‡
natamycin
nystatin^#
Systemic: amphotericin B^#, hamycin^‡

Squalene monooxygenase
inhibitors

Allylamines	Topical: naftifine terbinafine Systemic: terbinafine

Benzylamines	Topical: butenafine

Others

Topical: amorolfine

β-glucan synthase
inhibitors

Intracellular

Pyrimidine analogues/ thymidylate synthase inhibitors	flucytosine^#

Mitotic inhibitors	griseofulvin^#

Aminoacyl tRNA synthetase inhibitors	tavaborole

Others

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

Skeletal muscle relaxants (M03)

Peripherally acting
(primarily antinicotinic,
NMJ block)

Non-depolarizing

Curare alkaloids	Alcuronium Dimethyltubocurarine Tubocurarine

4° ammonium agents	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)

Depolarizing

Choline derivatives: Suxamethonium (Succinylcholine)

Polyalkylene derivatives: Hexamethonium

ACh release inhibitors

Botulinum toxin

Centrally acting

Carbamic acid esters	Carisoprodol Cyclarbamate Difebarbamate Febarbamate Meprobamate Phenprobamate Styramate Tybamate

Benzodiazepines	Bromazepam Diazepam Clonazepam Flunitrazepam Lorazepam Nitrazepam Temazepam Tetrazepam

Nonbenzodiazepines	Eszopiclone

Thienodiazepines	Etizolam

Quinazolines	Methaqualone

Anticholinergics (Antimuscarinics)	Cyclobenzaprine Orphenadrine

Other	Arbaclofen placarbil Baclofen Chlormezanone Chlorphenesin Chlorzoxazone Donepezil Eperisone Fenyramidol Flopropione Gabapentin GHB Inaperisone Lanperisone Mephenesin Mephenoxalone Metaxalone Methocarbamol Phenibut Pregabalin Pridinol Promoxolane Quinine Silperisone Thiocolchicoside Tizanidine Tolperisone Zoxazolamine

Directly acting

Dantrolene

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