Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C7H16NO3.C5H3N2O4 |
| Molecular Weight | 317.2952 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 2 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
C[N+](C)(C)CC(O)CC(O)=O.[O-]C(=O)C1=CC(=O)NC(=O)N1
InChI
InChIKey=MBULCFMSBDQQQT-UHFFFAOYSA-N
InChI=1S/C7H15NO3.C5H4N2O4/c1-8(2,3)5-6(9)4-7(10)11;8-3-1-2(4(9)10)6-5(11)7-3/h6,9H,4-5H2,1-3H3;1H,(H,9,10)(H2,6,7,8,11)
| Molecular Formula | C5H4N2O4 |
| Molecular Weight | 156.0963 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | C7H15NO3 |
| Molecular Weight | 161.1989 |
| Charge | 0 |
| Count |
|
| Stereochemistry | MIXED |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 2 |
| E/Z Centers | 0 |
| Optical Activity | ( + / - ) |
L-carnitine (L-beta-hydroxy-gamma-N,N,N-trimethylaminobutyric acid) is conditionally necessary for mitochondrial transport and metabolism of long-chain fatty acids, and thus for myocardial energetic metabolism. D-carnitine is not biologically active and might interfere with proper utilization of the L isomer, and so there are claims that the racemic mixture (DL-carnitine) should be avoided. The pharmacological effects of carnitine are stereospecific: L-carnitine was effective in various animal and clinical studies, while D- and DL-carnitine was found to be ineffective or even toxic to some cells and tissues, such as muscle cells and the myocardium. DL-carnitine caused symptoms of myasthenia and cardiac arrhythmias, which disappeared after L-carnitine administration.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Inflammatory and fibrotic processes are involved in the cardiotoxic effect of sunitinib: Protective role of L-carnitine. | 2016-01-22 |
|
| Inhibition of mitochondrial carnitine/acylcarnitine transporter by H(2)O(2): molecular mechanism and possible implication in pathophysiology. | 2013-04-25 |
|
| L-Carnitine rescues ketamine-induced attenuated heart rate and MAPK (ERK) activity in zebrafish embryos. | 2012-04 |
|
| Downregulation of oxidative and nitrosative apoptotic signaling by L-carnitine in Ifosfamide-induced Fanconi syndrome rat model. | 2012 |
|
| Inhibition of gene expression of organic cation/carnitine transporter and antioxidant enzymes in oxazaphosphorines-induced acute cardiomyopathic rat models. | 2012 |
|
| The protection role of heat shock protein 70 (HSP-70) in the testes of cadmium-exposed rats. | 2012 |
|
| Bezafibrate upregulates carnitine palmitoyltransferase II expression and promotes mitochondrial energy crisis dissipation in fibroblasts of patients with influenza-associated encephalopathy. | 2011-11 |
|
| The disruption of L-carnitine metabolism by aluminum toxicity and oxidative stress promotes dyslipidemia in human astrocytic and hepatic cells. | 2011-06-24 |
|
| Selective regulation of cardiac organic cation transporter novel type 2 (OCTN2) in dilated cardiomyopathy. | 2011-06 |
|
| L-carnitine protects against nickel-induced neurotoxicity by maintaining mitochondrial function in Neuro-2a cells. | 2011-05-15 |
|
| Transcellular movement of hydroxyurea is mediated by specific solute carrier transporters. | 2011-04 |
|
| Inhibition of gene expression of heart fatty acid binding protein and organic cation/carnitine transporter in doxorubicin cardiomyopathic rat model. | 2010-08-25 |
|
| The plasma carnitine concentration regulates renal OCTN2 expression and carnitine transport in rats. | 2010-06-10 |
|
| Valproate-induced hyperammonemic encephalopathy, rapidly improved by i.v. carnitine and glucose/thiamine. | 2010-06 |
|
| Integration of metabolomics and transcriptomics data to aid biomarker discovery in type 2 diabetes. | 2010-05 |
|
| Comparative effects of captopril and l-carnitine on blood pressure and antioxidant enzyme gene expression in the heart of spontaneously hypertensive rats. | 2010-04-25 |
|
| Vincristine-induced peripheral neuropathy in a neonate with congenital acute lymphoblastic leukemia. | 2010-04 |
|
| Inhibition of hepatic carnitine palmitoyl-transferase I (CPT IA) by valproyl-CoA as a possible mechanism of valproate-induced steatosis. | 2010-03-01 |
|
| Increased urinary losses of carnitine and decreased intramitochondrial coenzyme A in gentamicin-induced acute renal failure in rats. | 2010-01 |
|
| Identification of a novel organic anion transporter mediating carnitine transport in mouse liver and kidney. | 2010 |
|
| Organic cation/carnitine transporter OCTN3 is present in astrocytes and is up-regulated by peroxisome proliferators-activator receptor agonist. | 2009-12 |
|
| Peroxisome proliferator-activated receptor alpha plays a crucial role in L-carnitine anti-apoptosis effect in renal tubular cells. | 2009-10 |
|
| Interaction between pivaloylcarnitine and L-carnitine transport into L6 cells overexpressing hOCTN2. | 2009-08-14 |
|
| Inactivation by omeprazole of the carnitine transporter (OCTN2) reconstituted in liposomes. | 2009-05-15 |
|
| Pharmacological analysis demonstrates dramatic alteration of D1 dopamine receptor neuronal distribution in the rat analog of L-DOPA-induced dyskinesia. | 2009-04-15 |
|
| L-carnitine mediates protection against DNA damage in lymphocytes of aged rats. | 2009-04 |
|
| Progression of diethylnitrosamine-induced hepatic carcinogenesis in carnitine-depleted rats. | 2009-03-21 |
|
| The carnitine transporter SLC22A5 is not a general drug transporter, but it efficiently translocates mildronate. | 2009-02 |
|
| Carnitine deficiency: a possible risk factor in paracetamol hepatotoxicity. | 2009-02 |
|
| Carnitine deficiency aggravates carboplatin nephropathy through deterioration of energy status, oxidant/anti-oxidant balance, and inflammatory endocoids. | 2008-12-05 |
|
| High concentrations of stavudine impair fatty acid oxidation without depleting mitochondrial DNA in cultured rat hepatocytes. | 2008-06 |
|
| Role of Na+/L-carnitine transporter (OCTN2) in renal handling of pivaloylcarnitine and valproylcarnitine formed during pivalic acid-containing prodrugs and valproic acid treatment. | 2008 |
|
| Mechanism of the inhibitory effect of zwitterionic drugs (levofloxacin and grepafloxacin) on carnitine transporter (OCTN2) in Caco-2 cells. | 2006-11 |
|
| Acute renal failure due to phenazopyridine (Pyridium) overdose: case report and review of the literature. | 2006-11 |
|
| L-carnitine ameliorates doxorubicin-induced nephrotic syndrome in rats. | 2006-08 |
|
| Involvement of recognition and interaction of carnitine transporter in the decrease of L-carnitine concentration induced by pivalic acid and valproic acid. | 2006-08 |
|
| Positive regulation of hepatic carnitine palmitoyl transferase 1A (CPT1A) activities by soy isoflavones and L-carnitine. | 2006-03 |
|
| Effects of doxorubicin-containing chemotherapy and a combination with L-carnitine on oxidative metabolism in patients with non-Hodgkin lymphoma. | 2006-02 |
|
| Cardio-protective effects of carnitine in streptozotocin-induced diabetic rats. | 2006-01-19 |
|
| Pivotal role of Harakiri in the induction and prevention of gentamicin-induced hearing loss. | 2005-11-01 |
|
| Lethal cardiomyopathy in epidermolysis bullosa associated with amitriptyline. | 2005-08 |
|
| Effect of L-carnitine supplementation on acute valproate intoxication. | 1996-07 |
|
| Muscle carnitine deficiency associated with zidovudine-induced mitochondrial myopathy. | 1994-10 |
|
| Effect of L-carnitine on the zidovudine-induced destruction of human myotubes. Part I: L-carnitine prevents the myotoxicity of AZT in vitro. | 1994-07 |
|
| Zidovudine-induced mitochondrial myopathy is associated with muscle carnitine deficiency and lipid storage. | 1994-04 |
|
| Modulation of ethanol-mediated CYP2E1 induction by clofibrate and L-carnitine in rat liver. | 1993-12 |
|
| Echocardiographic assessment of anthracycline cardiotoxicity during different therapeutic regimens. | 1987 |
|
| Carnitine protection against adriamycin-induced cardiomyopathy in rats. | 1986-02-10 |
|
| Effect of administration of carnitine on the severity of myocardial infarction induced by isoproterenol in rats. | 1986-02 |
|
| Antagonism of doxorubicin cardiotoxicity by carnitine is specific of the L-diasteroisomer. | 1981-05 |
Patents
Sample Use Guides
in rat: supplemented with dl-carnitine (DLC) (1.2 mmol . kg-1. d-1)
Route of Administration:
Oral
Using rat phrenic nerve diaphragm preparations indirectly and directly stimulated with high rate pulses, D-carnitine (30 and 60 micro M), L-carnitine (60 micro M) and DL-carnitine (60 micro M) were shown to induce tetanic fade (D-carnitine = 19.7 +/- 3.1%, N = 6; L-carnitine = 16.6 +/- 2.4%, N = 6; DL-carnitine = 14.9 +/- 2.1%, N = 6) without any reduction of maximal tetanic tension. It was shown, that tetanic fade induced by L- and DL-carnitine was antagonized by choline (60 micro M).
| Substance Class |
Chemical
Created
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| Record UNII |
83EYV27FW2
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| Record Status |
Validated (UNII)
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| Record Version |
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