Details
Stereochemistry | ACHIRAL |
Molecular Formula | C7H5ClN2O |
Molecular Weight | 168.58 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
NC1=NC2=CC(Cl)=CC=C2O1
InChI
InChIKey=YGCODSQDUUUKIV-UHFFFAOYSA-N
InChI=1S/C7H5ClN2O/c8-4-1-2-6-5(3-4)10-7(9)11-6/h1-3H,(H2,9,10)
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 |
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 It was withdrawn from the market due to hepatotoxicity.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 |
---|---|---|---|
Target ID: GO:0042417 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6467036 |
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Target ID: CHEMBL4305 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10712246 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Flexin Approved UseZoxazolamine was indicated as a uricosuric agent to treat gout. Launch Date1956 |
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Primary | Flexin Approved UseZoxazolamine was indicated for the relief of muscle spasm in conditions such as musculoskeletal disorders and neurological diseases Launch Date1956 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
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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: |
unhealthy, 40 years n = 1 Health Status: unhealthy Condition: chronic polyartieular gout Age Group: 40 years Sex: M Population Size: 1 Sources: |
Disc. AE: Hepatitis... AEs leading to discontinuation/dose reduction: Hepatitis (acute, 1 patient) Sources: |
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: |
unhealthy, 40 years n = 1 Health Status: unhealthy Condition: chronic polyartieular gout Age Group: 40 years Sex: M Population Size: 1 Sources: |
PubMed
Title | Date | PubMed |
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Effect of microsomal enzyme inducers on the biliary excretion of cardiac glycosides. | 1974 Nov |
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The murine aromatic hydrocarbon responsiveness locus: a comparison of receptor levels and several inducible enzyme activities among recombinant inbred lines. | 1986 Mar |
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Effect of benzopyrone derivatives on drug activity and metabolism. | 1986 Oct-Dec |
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In-vivo effects of itraconazole on hepatic mixed-function oxidase. | 1988 Feb |
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Aryl hydrocarbon receptor signaling plays a significant role in mediating benzo[a]pyrene- and cigarette smoke condensate-induced cytogenetic damage in vivo. | 2001 Jan |
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In vivo hepatoprotective activity of active fraction from ethanolic extract of Eclipta alba leaves. | 2001 Oct |
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Moricizine, an antiarrhythmic agent, as a potent inhibitor of hepatic microsomal CYP1A. | 2002 Dec |
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Unexpected down-regulation of the hIK1 Ca2+-activated K+ channel by its opener 1-ethyl-2-benzimidazolinone in HaCaT keratinocytes. Inverse effects on cell growth and proliferation. | 2003 Jan 31 |
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Effect of novel anti-inflammatory ethanolamine derivatives with antioxidant properties on drug metabolising enzymes. | 2003 Jan-Mar |
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Effect of p-amino-diphenyl ethers on hepatic microsomal cytochrome P450. | 2003 Sep |
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Characteristics and a functional implication of Ca(2+)-activated K(+) current in mouse aortic endothelial cells. | 2004 Jan |
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Inhibition of endothelium-dependent vasorelaxation by extracellular K(+): a novel controlling signal for vascular contractility. | 2004 Jan |
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Functional and molecular identification of intermediate-conductance Ca(2+)-activated K(+) channels in breast cancer cells: association with cell cycle progression. | 2004 Jul |
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Transcription coactivator peroxisome proliferator-activated receptor-binding protein/mediator 1 deficiency abrogates acetaminophen hepatotoxicity. | 2005 Aug 30 |
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Effect of some biologically interesting substituted tetrahydro-1,4-oxazines on drug metabolising enzymes and on inflammation. | 2005 Oct |
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Simple pharmacological test battery to assess efficacy and side effect profile of centrally acting muscle relaxant drugs. | 2005 Sep-Oct |
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Isolation, structure elucidation and in vivo hepatoprotective potential of trans-tetracos-15-enoic acid from Indigofera tinctoria Linn. | 2006 Oct |
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Gender-specific induction of cytochrome P450s in nonylphenol-treated FVB/NJ mice. | 2006 Oct 15 |
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Transcription coactivator PRIP, the peroxisome proliferator-activated receptor (PPAR)-interacting protein, is redundant for the function of nuclear receptors PParalpha and CAR, the constitutive androstane receptor, in mouse liver. | 2007 |
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Alterations in xenobiotic metabolism in the long-lived Little mice. | 2007 Aug |
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The environmental estrogen, nonylphenol, activates the constitutive androstane receptor. | 2007 Aug |
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Surgical correction of fixed kyphosis. | 2007 Jun |
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Neutral genetic drift can alter promiscuous protein functions, potentially aiding functional evolution. | 2007 Jun 28 |
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Hepatoprotective potential of Aloe barbadensis Mill. against carbon tetrachloride induced hepatotoxicity. | 2007 May 22 |
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Molecular and cellular basis of small--and intermediate-conductance, calcium-activated potassium channel function in the brain. | 2008 Oct |
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Restoration of chaperone-mediated autophagy in aging liver improves cellular maintenance and hepatic function. | 2008 Sep |
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Constitutive androstane receptor mediates the induction of drug metabolism in mouse models of type 1 diabetes. | 2009 Aug |
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Sexually dimorphic regulation and induction of P450s by the constitutive androstane receptor (CAR). | 2009 Feb 4 |
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Anti-clastogenic effect of magnolol-containing Hange-koboku-to, Dai-joki-to, Goshaku-san, and Magnoliae Cortex on benzo(a)pyrene-induced clastogenicity in mice. | 2009 Jul |
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Inhibitory effect of magnolol on Trp-P-2-induced DNA damage in various organs in mice. | 2009 Jul |
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9,9-Dimethyl-12-(4-nitro-phen-yl)-9,10-dihydro-12H-benzo[a]xanthen-11(8H)-one. | 2009 Nov 21 |
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9,9-Dimethyl-12-phenyl-8,9-dihydro-12H-benzo[a]xanthen-11(10H)-one. | 2009 Nov 7 |
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Bioenhancers: Revolutionary concept to market. | 2010 Apr |
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12-(4-Chloro-phen-yl)-9,9-dimethyl-9,10-dihydro-8H-benzo[a]xanthen-11(12H)-one. | 2010 Feb 6 |
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Halogen, hydrogen and electrostatic interactions in 2-amino-5-chloro-1,3-benzoxazol-3-ium nitrate and 2-amino-5-chloro-1,3-benzoxazol-3-ium perchlorate. | 2010 Sep |
|
Functional coupling of ATP-binding cassette transporter Abcb6 to cytochrome P450 expression and activity in liver. | 2015 Mar 20 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/14492563
0.5 gm daily dose
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/14648123
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
Edited
Fri Dec 15 15:03:44 GMT 2023
by
admin
on
Fri Dec 15 15:03:44 GMT 2023
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Record UNII |
9DOW362Q29
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Record Status |
Validated (UNII)
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Record Version |
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NCI_THESAURUS |
C921
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NCI_THESAURUS |
C29696
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m11669
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CHEMBL472566
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Zoxazolamine
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200-519-4
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ACTIVE MOIETY |