CHLORPHENESIN CARBAMATE

Details

Stereochemistry	RACEMIC
Molecular Formula	C10H12ClNO4
Molecular Weight	245.66
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NC(=O)OCC(O)COC1=CC=C(Cl)C=C1

InChI

InChIKey=SKPLBLUECSEIFO-UHFFFAOYSA-N

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)

HIDE SMILES / InChI

Description
Sources: doi:10.1001/jama.1966.03100220075024
Curator's Comment: description was created based on several sources, including: http://www.drugs.com/mtm/chlorphenesin.html http://www.drugbank.ca/drugs/DB00856 https://en.wikipedia.org/wiki/Chlorphenesin

Chlorphenesin carbamate (Maolate, Musil) is a centrally acting muscle relaxant used to treat muscle pain and spasms. Сhlorphenesin acts in the central nervous system (CNS) rather than directly on skeletal muscle. It also has antifungal and some antibacterial properties. The major adverse effects are drowsiness and dizziness.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
nerve impulses 3 Target ID: nerve impulses Sources: https://www.drugs.com/mtm/maolate.html	Blocker 555

Conditions

Condition	Modality	Targets	Highest Phase	Product
Muscle pain 7 Sources: DOI:10.1001/jama.1966.03100220075024	Primary		Approved 8583	MAOLATE Approved Use Unknown Launch Date 1965
Muscle spasm 41 Sources: https://www.drugs.com/imprints/maolate-2166.html	Curative		Approved 8583	MAOLATE Approved Use Unknown Launch Date 1965

C_max

Value	Dose	Co-administered	Analyte	Population
14.9 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/5133920/	2 g single, oral dose: 2 g route of administration: Oral experiment type: SINGLE co-administered: METHOCARBAMOL	METHOCARBAMOL	CHLORPHENESIN CARBAMATE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
84 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/5133920/	2 g single, oral dose: 2 g route of administration: Oral experiment type: SINGLE co-administered: METHOCARBAMOL	METHOCARBAMOL	CHLORPHENESIN CARBAMATE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
0.44 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/5133920/	2 g single, oral dose: 2 g route of administration: Oral experiment type: SINGLE co-administered: METHOCARBAMOL	METHOCARBAMOL	CHLORPHENESIN CARBAMATE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
MATE1 415 MATE2 267

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
MATE1 416	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/26507723/	weak [IC50 >691.9 uM]	CHLORPHENESIN 3
MATE2 267	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/26507723/	weak [IC50 >691.9 uM]	CHLORPHENESIN 3

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:3643	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:3643
ChemicalBook	CB6493622	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB6493622
eMolecules	734530	https://www.emolecules.com/cgi-bin/more?vid=734530
MolPort	MolPort-002-070-331	https://www.molport.com/shop/molecule-link/MolPort-002-070-331

PubMed

Title	Date	PubMed
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2.	2011-07-14	21599003
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.	2009-11	20110015
Stimulatory effects of chlorzoxazone, a centrally acting muscle relaxant, on large conductance calcium-activated potassium channels in pituitary GH3 cells.	2003-01-03	12480161

Patents

Sample Use Guides

In Vivo Use Guide

for adults is 1.6 to 2.4 gm given in divided doses

Route of Administration: Oral

In Vitro Use Guide

chlorphenesin carbamate (CPC) has an apparent depressing action on the spinal neuron. CPC caused marked hyperpolarizations and depressed spontaneous activities in both of the primary afferent terminals (PAT) and motoneurons (MN).

Name

Type

Language

MAOLATE

Preferred Name

English

CHLORPHENESIN CARBAMATE

Official Name

English

CHLORPHENESIN CARBAMATE [GREEN BOOK]

Common Name

English

CHLORPHENESIN CARBAMATE [JAN]

Common Name

English

CHLORPHENESIN CARBAMATE [ORANGE BOOK]

Common Name

English

CHLORPHENESIN CARBAMATE [USAN]

Common Name

English

Chlorphenesin carbamate [WHO-DD]

Common Name

English

U-19646

Code

English

1,2-PROPANEDIOL, 3-(4-CHLOROPHENOXY)-, 1-CARBAMATE

Common Name

English

CHLORPHENESIN CARBAMATE [HSDB]

Common Name

English

CHLORPHENESIN CARBAMATE [VANDF]

Common Name

English

NSC-82943

Code

English

3-(P-CHLOROPHENOXY)-1,2-PROPANEDIOL 1-CARBAMATE

Common Name

English

U-19,646

Code

English

CHLORPHENESIN CARBAMATE [MI]

Common Name

English

CHLORPHENESIN CARBAMATE [MART.]

Common Name

English

Classification Tree Code System Code

CFR

21 CFR 520.434