Chlorphenesin carbamate

Chlorphenesin carbamate
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 ; chlorphenesin: 104-29-0 ;
PubChem CID	2724;
ChemSpider	2623;
UNII	57U5YI11WP; chlorphenesin: I670DAL4SZ ;
KEGG	D00770;
ChEBI	CHEBI:3642 ;
ChEMBL	ChEMBL607710 ;
CompTox Dashboard (EPA)	DTXSID0049028 ;
ECHA InfoCard	100.002.902
Chemical and physical data
Formula	C10H12ClNO4
Molar mass	245.66 g·mol−1
3D model (JSmol)	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 (February 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 (September 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 (May 1981). "Chlorphenesin sensitivity". Contact Dermatitis. 7 (3): 162. doi:10.1111/j.1600-0536.1981.tb04601.x. PMID 6456118. S2CID 37580364.
Burns DA (April 1986). "Allergic contact sensitivity to chlorphenesin". Contact Dermatitis. 14 (4): 246. doi:10.1111/j.1600-0536.1986.tb01234.x. PMID 2941223. S2CID 43810471.
"FDA Warns Consumers Against Using Mommy's Bliss Nipple Cream Product can be harmful to nursing infants". Food and Drug Administration.

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[1] Okuyama S, Aihara H (February 1987). "Antinociceptive effect of chlorphenesin carbamate in adjuvant arthritic rats". Research Communications in Chemical Pathology and Pharmacology. 55 (2): 147–60. PMID 3823606.

[2] Kurachi M, Aihara H (September 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.

[3] ATC code D01AE07

[4] Brown R (May 1981). "Chlorphenesin sensitivity". Contact Dermatitis. 7 (3): 162. doi:10.1111/j.1600-0536.1981.tb04601.x. PMID 6456118. S2CID 37580364.

[5] Burns DA (April 1986). "Allergic contact sensitivity to chlorphenesin". Contact Dermatitis. 14 (4): 246. doi:10.1111/j.1600-0536.1986.tb01234.x. PMID 2941223. S2CID 43810471.

[6] "FDA Warns Consumers Against Using Mommy's Bliss Nipple Cream Product can be harmful to nursing infants". Food and Drug Administration.