Chlorphenesin

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 Number	886-74-8
ATC code	D01AE07 (WHO)
PubChem	CID 2724
ChemSpider	2623
UNII	I670DAL4SZ
KEGG	D00770
ChEBI	CHEBI:3642
ChEMBL	CHEMBL607710
Chemical data
Formula	C10H12ClNO4
Molar 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)

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

1. 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.
2. 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.
3. ATC code D01AE07
4. Brown R (1981). "Chlorphenesin sensitivity". Contact Dermatitis 7 (3): 162. doi:10.1111/j.1600-0536.1981.tb04601.x. PMID 6456118.
5. Burns DA (1986). "Allergic contact sensitivity to chlorphenesin". Contact Dermatitis 14 (33): 246. doi:10.1111/j.1600-0536.1986.tb01234.x. PMID 2941223.
6. "FDA Warns Consumers Against Using Mommy's Bliss Nipple Cream Product can be harmful to nursing infants".