Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C8H9NO3 |
Molecular Weight | 167.162 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
N[C@H](C(O)=O)C1=CC=C(O)C=C1
InChI
InChIKey=LJCWONGJFPCTTL-ZETCQYMHSA-N
InChI=1S/C8H9NO3/c9-7(8(11)12)5-1-3-6(10)4-2-5/h1-4,7,10H,9H2,(H,11,12)/t7-/m0/s1
Molecular Formula | C8H9NO3 |
Molecular Weight | 167.162 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Oxfenicine is a CPT-1b-specific inhibitor. It must be transaminated to its active form, 4-hydroxyphenyl-glyoxylate, which is competitive with carnitine, preventing the formation of acylcarnitine. Because CPT-1b shows the highest sensitivity to 4-hydroxyphenyl-glyoxylate, inhibition of fatty acid oxidation by oxfenicine takes place selectively in those tissues that express this CPT isoform. It may be effective for treating noninsulin-dependent diabetes mellitus which is characterized by elevated fatty acid levels and obesity. In 1980 it was also tested in preclinical models of angina pectoris and ischemia.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: Q92523 Gene ID: 1375.0 Gene Symbol: CPT1B Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/27558315 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Preventing | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Facilitation and inhibition of retrieval in two aversive tasks in rats by intrahippocampal infusion of agonists of specific glutamate metabotropic receptor subtypes. | 2001 Aug |
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Modeling and kinetic analysis of the reaction system using whole cells with separately and co-expressed D-hydantoinase and N-carbamoylase. | 2002 Jun 30 |
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Fatty acids are important for the Frank-Starling mechanism and Gregg effect but not for catecholamine response in isolated rat hearts. | 2002 Nov |
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Dissociation between metabolic and efficiency effects of perhexiline in normoxic rat myocardium. | 2005 Dec |
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Inhibition of carnitine-acyl transferase I by oxfenicine studied in vivo with [11C]-labeled fatty acids. | 2005 Jul |
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Oxidative phenol coupling reactions catalyzed by OxyB: a cytochrome P450 from the vancomycin producing organism. implications for vancomycin biosynthesis. | 2007 May 30 |
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Efficient biocatalytic production of D-4-hydroxyphenylglycine by whole cells of recombinant Ralstonia pickettii. | 2009 Nov |
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Differential proteomic analysis highlights metabolic strategies associated with balhimycin production in Amycolatopsis balhimycina chemostat cultivations. | 2010 Nov 26 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27558315
In a preclinical study, rats were given a daily intraperitoneal injection of oxfenicine (150 mg/kg body wt) for 3 weeks.
Route of Administration:
Intraperitoneal
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27558315
Rat adipocytes were treated with various concentrations of oxfenicine (100 uM or 1 mM) for 2 h at 37 Degrees Celsius with gentle agitation. In cells treated with 1 mM oxfenicine, palmitate oxidation was significantly reduced by 50% compared with control cells. Isoproterenol-stimulated lipolysis was significantly decreased by 20% and 12% in epididymal adipocytes following treatment with 100 uM and 1 mM oxfenicine, respectively. Similarly, in subcutaneous inguinal adipocytes treatment with 100 uM and 1 mM of oxfenicine decreased stimulated lipolysis by 8% and 18%, respectively. Basal and insulin-stimulated glucose incorporation into lipids, the measure for lipogenesis, was reduced by 39% and 31%, respectively, in epididymal adipocytes following treatment with 1 mM oxfenicine. In adipocytes from the subcutaneous inguinal fat depot, the incorporation of glucose into lipids was also reduced by 41% under insulin-stimulated conditions, following 1 mM oxfenicine treatment
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:26:40 GMT 2023
by
admin
on
Fri Dec 15 15:26:40 GMT 2023
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Record UNII |
9YH0WH2Z02
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Record Status |
Validated (UNII)
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Record Version |
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NCI_THESAURUS |
C2079
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251-061-7
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CHEMBL1232077
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36143
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SUB09520MIG
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4810
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DB04291
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DTXSID3046403
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32462-30-9
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100000083059
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C91030
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9YH0WH2Z02
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