ZOXAZOLAMINE HYDROCHLORIDE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C7H5ClN2O.ClH
Molecular Weight	205.041
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

Cl.NC1=NC2=CC(Cl)=CC=C2O1

InChI

InChIKey=SFCBKXSIKZQDKX-UHFFFAOYSA-N

InChI=1S/C7H5ClN2O.ClH/c8-4-1-2-6-5(3-4)10-7(9)11-6;/h1-3H,(H2,9,10);1H

HIDE SMILES / InChI

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

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

Molecular Formula	C7H5ClN2O
Molecular Weight	168.58
Charge	0
Count

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6467036 | https://www.ncbi.nlm.nih.gov/pubmed/10712246 | https://pdfs.semanticscholar.org/f719/c3d1867bf65a6e38e7dc5647447ebee506c7.pdf | https://www.ncbi.nlm.nih.gov/pubmed/14492563

Zoxazolamine is a centrally acting muscle relaxant. It decreased striatal dopamine metabolism without affecting striatal dopamine concentrations. More specifically, Zoxazolamine was shown to decrease striatal dopamine turnover without directly affecting dopamine synthesis, catabolism, reuptake, or release. It is the IK(Ca) channel opener. It was approved for the relief of muscle spasm in conditions such as musculoskeletal disorders and neurological diseases. Later, it was submitted for the drug's use as a uricosuric agent to treat gout. It was withdrawn from the market due to hepatotoxicity.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
dopamine metabolic process 5 Target ID: GO:0042417 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6467036	Inhibitor 8297
Intermediate conductance calcium-activated potassium channel protein 4 10 Target ID: CHEMBL4305 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10712246	Opener 34

Conditions

Condition	Modality	Targets	Highest Phase	Product
Gout 28 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14462935 https://www.ncbi.nlm.nih.gov/pubmed/14492563 https://www.ncbi.nlm.nih.gov/pubmed/14038637	Primary		Withdrawn	Flexin Approved Use Zoxazolamine was indicated as a uricosuric agent to treat gout. Launch Date 1956
Muscle spasm 40 Sources: https://www.ncbi.nlm.nih.gov/pubmed/13286127 https://www.ncbi.nlm.nih.gov/pubmed/13371252 https://www.ncbi.nlm.nih.gov/pubmed/13403149 https://www.ncbi.nlm.nih.gov/pubmed/13462734	Primary		Withdrawn	Flexin Approved Use Zoxazolamine was indicated for the relief of muscle spasm in conditions such as musculoskeletal disorders and neurological diseases Launch Date 1956

C_max

Value	Dose	Co-administered	Analyte	Population
7.5 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/13571254/	1 g single, oral dose: 1 g route of administration: Oral experiment type: SINGLE co-administered:		ZOXAZOLAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
250 mg 4 times / day multiple, oral (starting) Dose: 250 mg, 4 times / day Route: oral Route: multiple Dose: 250 mg, 4 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/13726185	unhealthy, 40 years n = 1 Health Status: unhealthy Condition: chronic polyartieular gout Age Group: 40 years Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/13726185	Disc. AE: Hepatitis... AEs leading to discontinuation/dose reduction: Hepatitis (acute, 1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/13726185

AEs

AE	Significance	Dose	Population
Hepatitis	acute, 1 patient Disc. AE	250 mg 4 times / day multiple, oral (starting) Dose: 250 mg, 4 times / day Route: oral Route: multiple Dose: 250 mg, 4 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/13726185	unhealthy, 40 years n = 1 Health Status: unhealthy Condition: chronic polyartieular gout Age Group: 40 years Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/13726185

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP1A1 349

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP1A1 349	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/8651703/	yes

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY563103	https://www.001chemical.com/chem/61-80-3
3B Scientific (Wuhan) Corp	3B3-018650	http://www.3bsc.com/index/pro_info.php?id=41174
AA Blocks	AA003MLP	http://www.aablocks.com/goods/Goods/detail?id=AA003MLP
AHH Chemical co.,ltd	MT-33140	http://www.ahhchemical.com/product/MT-33140.html
AK Scientific, Inc. (AKSCI)	9267AB	http://www.aksci.com/item_detail.php?cat=9267AB
Aaron Chemicals	AR003NDH	http://www.aaronchem.com/61-80-3
AbMole Bioscience	M3142	http://www.abmole.com/products/zoxazolamine.html
Achemo Scientific Limited	AC-32519	http://www.achemo.com/product_view.asp?ID=36574
Achemtek	0104-010041	http://www.achemtek.com/61-80-3
Acros Organics	AC103380050	https://www.fishersci.com/shop/products/2-amino-5-chlorobenzoxazole-97-acros-organics-1/AC103380050
Acros Organics	AC103380250	https://www.fishersci.com/shop/products/2-amino-5-chlorobenzoxazole-97-acros-organics-1/AC103380250
Acros Organics	AC103380010	https://www.fishersci.com/shop/products/2-amino-5-chlorobenzoxazole-97-acros-organics/AC103380010
Alinda	ALBB-018399	http://alinda.ru/finechem_en_.html?i=ALBB-018399
Allbio Pharm Co., Ltd	AD03104	http://www.allbiopharm.com/product/n/AD03104
Ambinter	Amb1153987	http://www.ambinter.com/reference/1153987
Angene	AGN-PC-07Y50K	http://www.angenechemical.com/productshow/AGN-PC-07Y50K.html
Anward	ANW-58181	http://www.anward.com/pro_result/44632
ApexBio Technology	B1871	http://www.apexbt.com/zoxazolamine.html
AstaTech, Inc.	52984	http://www.astatechinc.com/CPSResult.php?CRNO=3492
Aurora Fine Chemicals LLC	A00.232.073	http://online.aurorafinechemicals.com/info?ID=A00.232.073
Aurum Pharmatech LLC	R1128	http://www.Aurumpharmatech.com/Product/ProductDetails/R1128
Avantor Inc	101181-818	https://us.vwr.com/store/catalog/product.jsp?catalog_number=101181-818
Avantor Inc	200040-814	https://us.vwr.com/store/product/7513627/2-amino-5-chlorobenzoxazole
Avantor Inc	200022-418	https://us.vwr.com/store/product/7513627/2-amino-5-chlorobenzoxazole-97
BLD Pharm	BD4370	http://www.bldpharm.com/products/61-80-3.html
BOC Sciences	61-80-3	https://buildingblock.bocsci.com/product/2-amino-5-chlorobenzoxazole-cas-61-80-3-323038.html
BioCrick	BCC4751	http://www.biocrick.com/Zoxazolamine-BCC4751.html
BioSynth	J-517385	https://www.biosynth.com/en/products/all-products/products/J-517385.html
CSNpharm	CSN16887	https://www.csnpharm.com/products/zoxazolamine.html
Capot Chemical	12473	http://www.capotchem.com/en/12473.htm
Capot Chemical	PubChem12473	http://www.capotchem.com/en/12473.htm
Chem Scene	CS-0013070	http://www.chemscene.com/61-80-3.html
ChemMol	49416527	http://www.chemmol.com/chemmol/49416527.html
ChemMol	99117832	http://www.chemmol.com/chemmol/99117832.html
Chemspace	CSSB00000198520	https://chem-space.com/CSSB00000198520
Clearsynth	CS-T-62858	https://www.clearsynth.com/en/CST62858.html
DC Chemicals	DC36143	http://www.dcchemicals.com//product_show-AI3-63120.html
Debye Scientific	DB-027769	http://www.debyesci.com/DB-027769.html
Hairui	HR102973	http://www.hairuichem.com/en/product/61-80-3.html
Heterocyclics Research Chemicals & Building blocks	JR-14592	http://www.heterocyclics.com/details.php?cat_id=JR-14592
LGC Standards	LGCFOR3325.00	https://www.lgcstandards.com/US/en/p/LGCFOR3325.00
Lab Network	LN00180136	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00180136
Matrix Scientific	81385	https://www.matrixscientific.com/081385.html
MedChem Express	HY-B1307	https://www.medchemexpress.com/Zoxazolamine.html
Molcore	MC563103	https://www.molcore.com/product/61-80-3
OChem	6751	http://www.ocheminc.com/index.php?act=psearch&pid=005A770
Oakwood	1002	http://www.oakwoodchemical.com/p-2-001002.aspx
Renno Tech	RL04341	http://www.rennotech.com/product_show.asp?id=4590
Sigma-Aldrich	A45807_ALDRICH	https://www.sigmaaldrich.com/catalog/product/aldrich/a45807?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Smolecule	S565567	https://www.smolecule.com/products/s565567
THE BioTek	bt-295297	https://www.thebiotek.com/product/others/bt-295297
Vitas-M Laboratory	BBL023547	http://www.request.vitasmlab.biz/index.php?option=com_search_stk&Itemid=22&stk=BBL023547&?utm_source=pubchem&utm_medium=p_search_link&utm_campaign=pubchem_search&utm_content=pubchem_slink
VladaChem	VL277549-1G	https://www.vladachem.com/product.php?products=61-80-3
abcr GmbH	AB146024	http://www.abcr.com/shop/en/AB146024
eNovation Chemicals	D651370	https://www.enovationchem.com/ProductDetails.asp?ProductID=D651370

PubMed

Title	Date	PubMed
Effect of microsomal enzyme inducers on the biliary excretion of cardiac glycosides.	1974 Nov	4418514
The murine aromatic hydrocarbon responsiveness locus: a comparison of receptor levels and several inducible enzyme activities among recombinant inbred lines.	1986 Mar	2856069
In-vivo effects of itraconazole on hepatic mixed-function oxidase.	1988 Feb	2452150
In vivo hepatoprotective activity of active fraction from ethanolic extract of Eclipta alba leaves.	2001 Oct	11883149
Moricizine, an antiarrhythmic agent, as a potent inhibitor of hepatic microsomal CYP1A.	2002 Dec	12393941
Inhibition of endothelium-dependent vasorelaxation by extracellular K(+): a novel controlling signal for vascular contractility.	2004 Jan	12969893
Transcription coactivator peroxisome proliferator-activated receptor-binding protein/mediator 1 deficiency abrogates acetaminophen hepatotoxicity.	2005 Aug 30	16109766
Effect of some biologically interesting substituted tetrahydro-1,4-oxazines on drug metabolising enzymes and on inflammation.	2005 Oct	16248839
Neutral genetic drift can alter promiscuous protein functions, potentially aiding functional evolution.	2007 Jun 28	17598905
Hepatoprotective potential of Aloe barbadensis Mill. against carbon tetrachloride induced hepatotoxicity.	2007 May 22	17291700
Molecular and cellular basis of small--and intermediate-conductance, calcium-activated potassium channel function in the brain.	2008 Oct	18597044
Restoration of chaperone-mediated autophagy in aging liver improves cellular maintenance and hepatic function.	2008 Sep	18690243
9,9-Dimethyl-12-(4-nitro-phen-yl)-9,10-dihydro-12H-benzo[a]xanthen-11(8H)-one.	2009 Nov 21	21578862
9,9-Dimethyl-12-phenyl-8,9-dihydro-12H-benzo[a]xanthen-11(10H)-one.	2009 Nov 7	21578757
Bioenhancers: Revolutionary concept to market.	2010 Apr	21836795

Patents

Sample Use Guides

In Vivo Use Guide

0.5 gm daily dose

Route of Administration: Oral

In Vitro Use Guide

Mouse aortic endothelial cells were loaded with 0.5 uM Ca2+ in the pipette and current measured at 50 and −50 mV during repetitive ramps and the corresponding I/V curves constructed. 100 uM of zoxazolamine activated the K(Ca) current.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 16:34:38 GMT 2023` Edited by `admin` on `Sat Dec 16 16:34:38 GMT 2023`
Record UNII	B9H77T8HTQ
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ZOXAZOLAMINE HYDROCHLORIDE

Common Name

English

ZOXAZOLAMINE HYDROCHLORIDE [MI]

Common Name

English

2-BENZOXAZOLAMINE, 5-CHLORO-, HYDROCHLORIDE (1:1)

Systematic Name

English

Code System Code Type Description

MERCK INDEX

m11669