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) |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Preventing | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Differential proteomic analysis highlights metabolic strategies associated with balhimycin production in Amycolatopsis balhimycina chemostat cultivations. | 2010-11-26 |
|
| 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. | 2009-12-04 |
|
| Efficient biocatalytic production of D-4-hydroxyphenylglycine by whole cells of recombinant Ralstonia pickettii. | 2009-11 |
|
| Tracking radical migration in large hydrogen deficient peptides with covalent labels: facile movement does not equal indiscriminate fragmentation. | 2009-06 |
|
| Exploring the substrate specificity of OxyB, a phenol coupling P450 enzyme involved in vancomycin biosynthesis. | 2008-08-21 |
|
| Facile immobilization of evolved agrobacterium radiobacter carbamoylase with high thermal and oxidative stability. | 2008-08-13 |
|
| Role of glucose metabolism in the recovery of postischemic LV mechanical function: effects of insulin and other metabolic modulators. | 2008-06 |
|
| Metabolic response to an acute jump in cardiac workload: effects on malonyl-CoA, mechanical efficiency, and fatty acid oxidation. | 2008-02 |
|
| Oxidative phenol coupling reactions catalyzed by OxyB: a cytochrome P450 from the vancomycin producing organism. implications for vancomycin biosynthesis. | 2007-05-30 |
|
| Racemization in suzuki couplings: a quantitative study using 4-hydroxyphenylglycine and tyrosine derivatives as probe molecules. | 2007-02-02 |
|
| The enduracidin biosynthetic gene cluster from Streptomyces fungicidicus. | 2006-10 |
|
| Modification of myocardial substrate use as a therapy for heart failure. | 2006-09 |
|
| Sequential activation of caspases and synergistic beta-cell cytotoxicity by palmitate and anti-Fas antibodies. | 2006-08-22 |
|
| Dissociation between metabolic and efficiency effects of perhexiline in normoxic rat myocardium. | 2005-12 |
|
| Inhibition of carnitine-acyl transferase I by oxfenicine studied in vivo with [11C]-labeled fatty acids. | 2005-07 |
|
| Carnitine palmitoyl transferase-I inhibition prevents ventricular remodeling and delays decompensation in pacing-induced heart failure. | 2005-06-01 |
|
| Fatty acid oxidation inhibition with PPARalpha activation (FOXIB/PPARalpha) for normalizing gene expression in heart failure? | 2005-06-01 |
|
| Regulation of pyruvate dehydrogenase activity and citric acid cycle intermediates during high cardiac power generation. | 2005-01-15 |
|
| Engineering p-hydroxyphenylpyruvate dioxygenase to a p-hydroxymandelate synthase and evidence for the proposed benzene oxide intermediate in homogentisate formation. | 2004-01-27 |
|
| Role of the fuel utilized by tissues on coronary vessel response to physical stimuli in isolated rat hearts. | 2004 |
|
| Inhibitory effects in the side reactions occurring during the enzymic synthesis of amoxicillin: p-hydroxyphenylglycine methyl ester and amoxicillin hydrolysis. | 2003-08 |
|
| Incorporation of glucose analogs by GtfE and GtfD from the vancomycin biosynthetic pathway to generate variant glycopeptides. | 2002-12 |
|
| Fatty acids are important for the Frank-Starling mechanism and Gregg effect but not for catecholamine response in isolated rat hearts. | 2002-11 |
|
| The activation of metabotropic glutamate receptors differentially affects GABA and alpha-melanocyte stimulating hormone release from the hypothalamus and the posterior pituitary of male rats. | 2002-07-19 |
|
| Modeling and kinetic analysis of the reaction system using whole cells with separately and co-expressed D-hydantoinase and N-carbamoylase. | 2002-06-30 |
|
| Equilibrium modeling of extractive enzymatic hydrolysis of penicillin G with concomitant 6-aminopenicillanic acid crystallization. | 2002-05-20 |
|
| Palmitate-induced cardiac apoptosis is mediated through CPT-1 but not influenced by glucose and insulin. | 2002-02 |
|
| Characterisation of a hydroxymandelate oxidase involved in the biosynthesis of two unusual amino acids occurring in the vancomycin group of antibiotics. | 2001-09-21 |
|
| Facilitation and inhibition of retrieval in two aversive tasks in rats by intrahippocampal infusion of agonists of specific glutamate metabotropic receptor subtypes. | 2001-08 |
Patents
Sample Use Guides
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
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
Mon Mar 31 17:57:57 GMT 2025
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on
Mon Mar 31 17:57:57 GMT 2025
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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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CHEMBL1232077
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36143
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4810
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32462-30-9
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100000083059
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C91030
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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ACTIVE MOIETY |
