U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of OXFENICINE

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

HIDE SMILES / InChI

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

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Q92523
Gene ID: 1375.0
Gene Symbol: CPT1B
Target Organism: Homo sapiens (Human)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Facilitation and inhibition of retrieval in two aversive tasks in rats by intrahippocampal infusion of agonists of specific glutamate metabotropic receptor subtypes.
2001 Aug
Characterisation of a hydroxymandelate oxidase involved in the biosynthesis of two unusual amino acids occurring in the vancomycin group of antibiotics.
2001 Sep 21
Incorporation of glucose analogs by GtfE and GtfD from the vancomycin biosynthetic pathway to generate variant glycopeptides.
2002 Dec
Palmitate-induced cardiac apoptosis is mediated through CPT-1 but not influenced by glucose and insulin.
2002 Feb
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 Jul 19
Modeling and kinetic analysis of the reaction system using whole cells with separately and co-expressed D-hydantoinase and N-carbamoylase.
2002 Jun 30
Equilibrium modeling of extractive enzymatic hydrolysis of penicillin G with concomitant 6-aminopenicillanic acid crystallization.
2002 May 20
Fatty acids are important for the Frank-Starling mechanism and Gregg effect but not for catecholamine response in isolated rat hearts.
2002 Nov
Inhibitory effects in the side reactions occurring during the enzymic synthesis of amoxicillin: p-hydroxyphenylglycine methyl ester and amoxicillin hydrolysis.
2003 Aug
Engineering p-hydroxyphenylpyruvate dioxygenase to a p-hydroxymandelate synthase and evidence for the proposed benzene oxide intermediate in homogentisate formation.
2004 Jan 27
Dissociation between metabolic and efficiency effects of perhexiline in normoxic rat myocardium.
2005 Dec
Inhibition of carnitine-acyl transferase I by oxfenicine studied in vivo with [11C]-labeled fatty acids.
2005 Jul
Carnitine palmitoyl transferase-I inhibition prevents ventricular remodeling and delays decompensation in pacing-induced heart failure.
2005 Jun 1
Fatty acid oxidation inhibition with PPARalpha activation (FOXIB/PPARalpha) for normalizing gene expression in heart failure?
2005 Jun 1
The enduracidin biosynthetic gene cluster from Streptomyces fungicidicus.
2006 Oct
Racemization in suzuki couplings: a quantitative study using 4-hydroxyphenylglycine and tyrosine derivatives as probe molecules.
2007 Feb 2
Oxidative phenol coupling reactions catalyzed by OxyB: a cytochrome P450 from the vancomycin producing organism. implications for vancomycin biosynthesis.
2007 May 30
Exploring the substrate specificity of OxyB, a phenol coupling P450 enzyme involved in vancomycin biosynthesis.
2008 Aug 21
Metabolic response to an acute jump in cardiac workload: effects on malonyl-CoA, mechanical efficiency, and fatty acid oxidation.
2008 Feb
Role of glucose metabolism in the recovery of postischemic LV mechanical function: effects of insulin and other metabolic modulators.
2008 Jun
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
Efficient biocatalytic production of D-4-hydroxyphenylglycine by whole cells of recombinant Ralstonia pickettii.
2009 Nov
Differential proteomic analysis highlights metabolic strategies associated with balhimycin production in Amycolatopsis balhimycina chemostat cultivations.
2010 Nov 26
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 Fri Dec 15 15:26:40 GMT 2023
Edited
by admin
on Fri Dec 15 15:26:40 GMT 2023
Record UNII
9YH0WH2Z02
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
OXFENICINE
INN   USAN  
USAN   INN  
Official Name English
(S)-(4-HYDROXYPHENYL)GLYCINE
Common Name English
UK-25,842
Code English
OXFENICINE [USAN]
Common Name English
(2R)-2-AMINO-2-(4-HYDROXYPHENYL)ACETIC ACID
Systematic Name English
BENZENEACETIC ACID, .ALPHA.-AMINO-4-HYDROXY-, (S)-
Common Name English
AMOXICILLIN SODIUM IMPURITY I [EP IMPURITY]
Common Name English
UK-25842
Code English
oxfenicine [INN]
Common Name English
L-2-(P-HYDROXYPHENYL)GLYCINE
Common Name English
4-HYDROXYPHENYLGLYCINE, (S)-
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C2079
Created by admin on Fri Dec 15 15:26:40 GMT 2023 , Edited by admin on Fri Dec 15 15:26:40 GMT 2023
Code System Code Type Description
ECHA (EC/EINECS)
251-061-7
Created by admin on Fri Dec 15 15:26:40 GMT 2023 , Edited by admin on Fri Dec 15 15:26:40 GMT 2023
PRIMARY
ChEMBL
CHEMBL1232077
Created by admin on Fri Dec 15 15:26:40 GMT 2023 , Edited by admin on Fri Dec 15 15:26:40 GMT 2023
PRIMARY
PUBCHEM
36143
Created by admin on Fri Dec 15 15:26:40 GMT 2023 , Edited by admin on Fri Dec 15 15:26:40 GMT 2023
PRIMARY
EVMPD
SUB09520MIG
Created by admin on Fri Dec 15 15:26:40 GMT 2023 , Edited by admin on Fri Dec 15 15:26:40 GMT 2023
PRIMARY
INN
4810
Created by admin on Fri Dec 15 15:26:40 GMT 2023 , Edited by admin on Fri Dec 15 15:26:40 GMT 2023
PRIMARY
DRUG BANK
DB04291
Created by admin on Fri Dec 15 15:26:40 GMT 2023 , Edited by admin on Fri Dec 15 15:26:40 GMT 2023
PRIMARY
EPA CompTox
DTXSID3046403
Created by admin on Fri Dec 15 15:26:40 GMT 2023 , Edited by admin on Fri Dec 15 15:26:40 GMT 2023
PRIMARY
CAS
32462-30-9
Created by admin on Fri Dec 15 15:26:40 GMT 2023 , Edited by admin on Fri Dec 15 15:26:40 GMT 2023
PRIMARY
SMS_ID
100000083059
Created by admin on Fri Dec 15 15:26:40 GMT 2023 , Edited by admin on Fri Dec 15 15:26:40 GMT 2023
PRIMARY
NCI_THESAURUS
C91030
Created by admin on Fri Dec 15 15:26:40 GMT 2023 , Edited by admin on Fri Dec 15 15:26:40 GMT 2023
PRIMARY
FDA UNII
9YH0WH2Z02
Created by admin on Fri Dec 15 15:26:40 GMT 2023 , Edited by admin on Fri Dec 15 15:26:40 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
PARENT -> IMPURITY
Related Record Type Details
ACTIVE MOIETY