Chlorphenesin carbamate

Short description: Muscle relaxant drug

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 Y
* chlorphenesin: 104-29-0 Y

PubChem CID|

* 2724

ChemSpider|

* 2623

UNII|

* 57U5YI11WP
* chlorphenesin: I670DAL4SZ Y

KEGG|

* D00770

ChEBI|

* CHEBI:3642 Y

ChEMBL|

* ChEMBL607710 Y

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 carbamate 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.

## Chlorphenesin

A related chemical, chlorphenesin (C9H11ClO3) without the carbamate group, is used as a preservative in products such as cosmetics. It has antifungal and some antibacterial properties, and is classified as an antifungal for topical use by the WHO.[3]

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]

## See also

* Methocarbamol

## References

1. ↑ "Antinociceptive effect of chlorphenesin carbamate in adjuvant arthritic rats". Research Communications in Chemical Pathology and Pharmacology 55 (2): 147–60. February 1987. PMID 3823606.
2. ↑ "Effect of a muscle relaxant, chlorphenesin carbamate, on the spinal neurons of rats". Japanese Journal of Pharmacology 36 (1): 7–13. September 1984. doi:10.1254/jjp.36.7. PMID 6503049.
3. ↑ ATC code D01AE07
4. ↑ "Chlorphenesin sensitivity". Contact Dermatitis 7 (3): 162. May 1981. doi:10.1111/j.1600-0536.1981.tb04601.x. PMID 6456118.
5. ↑ "Allergic contact sensitivity to chlorphenesin". Contact Dermatitis 14 (4): 246. April 1986. 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". https://www.fda.gov/NewsEvents/Newsroom/PressAnnouncements/2008/ucm116900.htm.

* v
* t
* e

Antifungals (D01 and J02)

Wall/
membrane|

| Ergosterol
inhibitors|

| Azoles (lanosterol 14α-
demethylase inhibitors)|

| Imidazoles|

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

* Systemic: ketoconazole

|

Triazoles|

* Topical: efinaconazole
* fluconazole#
* terconazole

* Systemic: fluconazole#
* hexaconazole‡
* fosfluconazole
* 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|

* Systemic: echinocandins (anidulafungin
* biafungin
* caspofungin
* cilofungin
* micafungin)

Intracellular|

| Pyrimidine analogues/
thymidylate synthase inhibitors|

* Systemic: flucytosine#

|

Mitotic inhibitors|

* Systemic: griseofulvin#

Aminoacyl tRNA synthetase inhibitors|

* Topical: tavaborole

Others|

* bromochlorosalicylanilide
* chlorophetanol
* chlorphenesin
* ciclopirox
* crystal violet
* dimazole
* ethylparaben
* haloprogin‡
* polynoxylin
* potassium iodide#
* salicylic acid
* selenium disulfide#
* sodium thiosulfate#
* sulbentine
* taurolidine
* ticlatone
* tolciclate
* tolnaftate
* tribromometacresol
* undecylenic acid
* Whitfield's ointment#

* citronella oil
* lemon grass
* lemon myrtle
* orange oil
* patchouli
* tea tree oil
* PCP: atovaquone
* dapsone
* pentamidine

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

* v
* t
* e

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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