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 |
---|---|---|---|
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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Incorporation of glucose analogs by GtfE and GtfD from the vancomycin biosynthetic pathway to generate variant glycopeptides. | 2002 Dec |
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Inhibitory effects in the side reactions occurring during the enzymic synthesis of amoxicillin: p-hydroxyphenylglycine methyl ester and amoxicillin hydrolysis. | 2003 Aug |
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Role of the fuel utilized by tissues on coronary vessel response to physical stimuli in isolated rat hearts. | 2004 |
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Engineering p-hydroxyphenylpyruvate dioxygenase to a p-hydroxymandelate synthase and evidence for the proposed benzene oxide intermediate in homogentisate formation. | 2004 Jan 27 |
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Regulation of pyruvate dehydrogenase activity and citric acid cycle intermediates during high cardiac power generation. | 2005 Jan 15 |
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The enduracidin biosynthetic gene cluster from Streptomyces fungicidicus. | 2006 Oct |
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Modification of myocardial substrate use as a therapy for heart failure. | 2006 Sep |
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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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Facile immobilization of evolved agrobacterium radiobacter carbamoylase with high thermal and oxidative stability. | 2008 Aug 13 |
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Metabolic response to an acute jump in cardiac workload: effects on malonyl-CoA, mechanical efficiency, and fatty acid oxidation. | 2008 Feb |
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Use of the SPhos ligand to suppress racemization in arylpinacolboronate ester Suzuki couplings involving alpha-amino acids. Synthesis of biaryl derivatives of 4-hydroxyphenylglycine, tyrosine, and tryptophan. | 2009 Dec 4 |
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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 UTC 2023
by
admin
on
Fri Dec 15 15:26:40 UTC 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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C91030
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9YH0WH2Z02
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PARENT -> IMPURITY |
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EP
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ACTIVE MOIETY |