CHLORZOXAZONE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C7H4ClNO2
Molecular Weight	169.565
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

ClC1=CC=C2OC(=O)NC2=C1

InChI

InChIKey=TZFWDZFKRBELIQ-UHFFFAOYSA-N

InChI=1S/C7H4ClNO2/c8-4-1-2-6-5(3-4)9-7(10)11-6/h1-3H,(H,9,10)

HIDE SMILES / InChI

Molecular Formula	C7H4ClNO2
Molecular Weight	169.565
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description

Chlorzoxazone is a centrally acting central muscle relaxant with sedative properties. It is claimed to inhibit muscle spasm by exerting an effect primarily at the level of the spinal cord and subcortical areas of the brain where it inhibits multisynaptic reflex arcs involved in producing and maintaining skeletal muscle spasm of varied etiology. The clinical result is a reduction of the skeletal muscle spasm with relief of pain and increased mobility of the involved muscles. Chlorzoxazone is indicated as an adjunct to rest, physical therapy, and other measures for the relief of discomfort associated with acute, painful musculoskeletal conditions. The mode of action of this drug has not been clearly identified, but may be related to its sedative properties. Chlorzoxazone does not directly relax tense skeletal muscles in man.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Intermediate conductance calcium-activated potassium channel protein 4 10	Activator 1,430

Conditions

Condition	Modality	Targets	Highest Phase	Product
Muscle spasm 40	Primary		Approved 8,429	CHLORZOXAZONE

C_max

Value	Dose	Co-administered	Analyte	Population
36.3 μg/mL	750 mg single, oral	ACETAMINOPHEN	CHLORZOXAZONE plasma	Homo sapiens
5.1 μg/mL	250 mg single, oral	QUERCETIN	CHLORZOXAZONE plasma	Homo sapiens
3.45 μg/mL	250 mg single, oral		CHLORZOXAZONE plasma	Homo sapiens
15 μg/mL	500 mg single, oral		CHLORZOXAZONE serum	Homo sapiens
5.2 μg/mL	500 mg single, oral		CHLORZOXAZONE serum	Homo sapiens
12.2 μg/mL	500 mg single, oral		CHLORZOXAZONE serum	Homo sapiens
0.14 μg/mL	250 mg single, oral	QUERCETIN	6-HYDROXYCHLORZOXAZONE plasma	Homo sapiens
0.2 μg/mL	250 mg single, oral		6-HYDROXYCHLORZOXAZONE plasma	Homo sapiens

AUC

Value	Dose	Co-administered	Analyte	Population
4084 μg × h/mL	750 mg single, oral	ACETAMINOPHEN	CHLORZOXAZONE plasma	Homo sapiens
16.69 μg × h/mL	250 mg single, oral	QUERCETIN	CHLORZOXAZONE plasma	Homo sapiens
9.86 μg × h/mL	250 mg single, oral		CHLORZOXAZONE plasma	Homo sapiens
43.5 mg × h/L	500 mg single, oral		CHLORZOXAZONE serum	Homo sapiens
15.7 μg × h/mL	500 mg single, oral		CHLORZOXAZONE serum	Homo sapiens
32.8 μg × h/mL	500 mg single, oral		CHLORZOXAZONE serum	Homo sapiens
0.64 μg × h/mL	250 mg single, oral	QUERCETIN	6-HYDROXYCHLORZOXAZONE plasma	Homo sapiens
0.95 μg × h/mL	250 mg single, oral		6-HYDROXYCHLORZOXAZONE plasma	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
1.12 h	750 mg single, oral	ACETAMINOPHEN	CHLORZOXAZONE plasma	Homo sapiens
1.65 h	250 mg single, oral	QUERCETIN	CHLORZOXAZONE plasma	Homo sapiens
1.21 h	250 mg single, oral		CHLORZOXAZONE plasma	Homo sapiens
1.1 h	500 mg single, oral		CHLORZOXAZONE serum	Homo sapiens
1.4 h	500 mg single, oral		CHLORZOXAZONE serum	Homo sapiens
1.2 h	500 mg single, oral		CHLORZOXAZONE serum	Homo sapiens

F_unbound

Value	Dose	Analyte	Population
3.9%	500 mg single, oral	CHLORZOXAZONE serum	Homo sapiens
3.2%	500 mg single, oral	CHLORZOXAZONE serum	Homo sapiens
4%	500 mg single, oral	CHLORZOXAZONE serum	Homo sapiens

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1,737

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP2E1 667 CYP1A2 1,054 CYP1A1 349

Drug as victim

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Target	Modality	Activity
CYP2E1 667	substrate 3,367	major
CYP1A1 349	substrate 3,367	minor
CYP1A2 1,054	substrate 3,367	minor
CYP3A4 1,737	substrate 3,367	minor

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
ChEBI	CHEBI:3655	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:3655
ChemicalBook	CB0392987	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB0392987
MolPort	MolPort-001-759-947	https://www.molport.com/shop/molecule-link/MolPort-001-759-947
MolPort	MolPort-006-110-468	https://www.molport.com/shop/molecule-link/MolPort-006-110-468
Selleck Chemicals	chlorzoxazone	http://www.selleckchem.com/products/chlorzoxazone.html

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PubMed

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Title	Date	PubMed
[Rhabdomyolysis and cholestatic hepatitis under treatment with simvastatin and chlorzoxazone].	1999 Apr 3	10322565
CYP2E1-dependent benzene toxicity: the role of extrahepatic benzene metabolism.	1999 Jun-Jul	10463382
Pharmacological activation of cloned intermediate- and small-conductance Ca(2+)-activated K(+) channels.	2000 Mar	10712246
EBIO, an agent causing maintained epithelial chloride secretion by co-ordinate actions at both apical and basolateral membranes.	2001	11845318
Chlorzoxazone: a probe drug the metabolism of which can be used to monitor one-point blood sampling in the carbon tetrachloride-intoxicated rat.	2001 Aug	11727787

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Patents

Sample Use Guides

In Vivo Use Guide

One tablet three or four times daily. If adequate response is not obtained with this dose, it may be increased to one and one-half tablets (750 mg) three or four times daily. As improvement occurs dosage can usually be reduced.

Route of Administration: Oral

In Vitro Use Guide

Chlorzoxazone did not affect the tension of the rat thoracic artery rings at rest, but relaxed the precontraction induced by 1 uM noradrenaline in an endothelium independent manner. Preincubation with chlorzoxazone also antagonized the contraction induced by 1 uM noradrenaline or 25 mM KCl.

Substance Class	Chemical
Record UNII	H0DE420U8G
Record Status	`Validated (UNII)`
Record Version

Show entries

Name

Type

Language

CHLORZOXAZONE

Official Name

English

CHLORZOXAZONE [MART.]

Common Name

English

chlorzoxazone [INN]

Common Name

English

Chlorzoxazone [WHO-DD]

Common Name

English

CHLORZOXAZONE [USP-RS]

Common Name

English

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Classification Tree

Code System

Code

Muscle relaxant

LIVERTOX

NBK548137

Established Pharmacologic Class

NDF-RT

N0000175737

Oxazol, thiazine, and triazine derivatives

WHO-VATC

QM03BB53

Oxazol, thiazine, and triazine derivatives

WHO-ATC

M03BB03

Oxazol, thiazine, and triazine derivatives

WHO-VATC

QM03BB03

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Code System

Code

Type

Description

ECHA (EC/EINECS)

202-403-9

PRIMARY

EPA CompTox

DTXSID9022813

PRIMARY

MESH

D002753

PRIMARY

FDA UNII

H0DE420U8G

PRIMARY

DAILYMED

H0DE420U8G

PRIMARY

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Related Record

Type

Details


					6D53G0FD0Z

PLASMA PROTEIN FRACTION (HUMAN)

BINDER->LIGAND

Interaction Type:

BINDING

Amount:

[13 to 18] (average)


					03BYF220B6

CYTOCHROME P450 2E1

METABOLIC ENZYME -> SUBSTRATE

Amount:


					H0DE420U8G

CHLORZOXAZONE

EXCRETED UNCHANGED

Amount:

MOLE PERCENT OF AMOUNT ADMINISTERED [<1] (average)

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Related Record

Type

Details


					HCL8UQ2CG0

6-HYDROXYCHLORZOXAZONE GLUCURONIDE

METABOLITE INACTIVE -> PARENT

Interaction Type:

MAJOR

Qualification:

URINE

Amount:

MOLE PERCENT OF AMOUNT ADMINISTERED [>80] (limits)


					M5YLT4Y73F

6-HYDROXYCHLORZOXAZONE

METABOLITE -> PARENT

Comments:

further metabolized to glucoronide

Interaction Type:

MAJOR

Qualification:

PLASMA

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Related Record

Type

Details


					H0DE420U8G

CHLORZOXAZONE

ACTIVE MOIETY

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Name	Property Type	Amount	Parameters
Volume of Distribution	PHARMACOKINETIC	0.2 Liters/Kilogram (average)

Biological Half-life	PHARMACOKINETIC	60 minutes (average)

Cmax	PHARMACOKINETIC	36.3 microgram/mL [34 to 38.6] (average)	ROUTE OF ADMINISTRATION PHARMACOKINETIC ORAL DOSE PHARMACOKINETIC 750 mg (average) COADMINISTERED WITH 900 MG OF ACETAMINOPHEN

Tmax	PHARMACOKINETIC	38 minutes [34.7 to 41.3] (average)	ROUTE OF ADMINISTRATION PHARMACOKINETIC ORAL DOSE PHARMACOKINETIC 750 mg (average) COADMINISTERED WITH 900 MG OF ACETAMINOPHEN

SMILES

InChI

CNS Activity

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Funbound

Overview

OverviewOther

Drug as victim

Sourcing

PubMed

Patents

Sample Use Guides

C_max

T_1/2

F_unbound