Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C10H20NO4.Cl |
| Molecular Weight | 253.723 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[Cl-].CCC(=O)O[C@H](CC(O)=O)C[N+](C)(C)C
InChI
InChIKey=KTFMPDDJYRFWQE-DDWIOCJRSA-N
InChI=1S/C10H19NO4.ClH/c1-5-10(14)15-8(6-9(12)13)7-11(2,3)4;/h8H,5-7H2,1-4H3;1H/t8-;/m1./s1
| Molecular Formula | C10H19NO4 |
| Molecular Weight | 217.2622 |
| Charge | 0 |
| Count |
|
| Stereochemistry | EPIMERIC |
| Additional Stereochemistry | No |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
| Molecular Formula | ClH |
| Molecular Weight | 36.461 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
Levocarnitine propionate or Propionyl L-carnitine (PLC) is the propionyl ester of L-carnitine. Propionyl-L-carnitine stimulates energy production in ischaemic muscles by increasing citric acid cycle flux and stimulating pyruvate dehydrogenase activity. The free radical scavenging activity of the drug may also be beneficial. Propionyl-L-carnitine improves coagulative fibrinolytic homeostasis in vasal endothelium and positively affects blood viscosity. It exhibits a high affinity for the muscle enzyme, carnitine acyl transferase, and as such readily converts into propionyl-CoA and free carnitine. Most studies of the therapeutic use of PLC are focused on the prevention and treatment of ischemic heart disease, congestive heart failure, hypertrophic heart disease, and peripheral arterial disease. PLC is marketed under the trade name Dromos®. It is indicated for patients with peripheral arterial occlusive disorders and for exercise intolerance enhancement in patients with chronic congestive heart failure. Dromos is marketed in Italy.
Originator
Sources: www.ncbi.nlm.nih.gov/pubmed/16857830http://adisinsight.springer.com/drugs/800003253
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: P50416 Gene ID: 1374.0 Gene Symbol: CPT1A Target Organism: Homo sapiens (Human) |
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Target ID: P23786 Gene ID: 1376.0 Gene Symbol: CPT2 Target Organism: Homo sapiens (Human) |
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Target ID: P43155 Gene ID: 1384.0 Gene Symbol: CRAT Target Organism: Homo sapiens (Human) |
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Target ID: O43772 Gene ID: 788.0 Gene Symbol: SLC25A20 Target Organism: Homo sapiens (Human) |
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Target ID: WP408 Sources: DOI: 10.1201/b17092-12 |
|||
Target ID: CHEMBL2216739 |
|||
Target ID: WP623 Sources: DOI: 10.1201/b17092-12 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | CARNITOR Approved UseCARNITOR (levocarnitine) is indicated in the treatment of primary systemic carnitine
deficiency. Launch Date1985 |
|||
| Primary | Dromos Approved UseIt is indicated for patients with peripheral arterial occlusive disorders and for exercise intolerance enchancement in patients with chronic congestive heart failure. |
|||
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
79.2 nmol/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7658356 |
330 mg 2 times / day multiple, oral dose: 330 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
LEVOCARNITINE blood | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
80.3 nmol/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7658356 |
2 g 2 times / day multiple, oral dose: 2 g route of administration: Oral experiment type: MULTIPLE co-administered: |
LEVOCARNITINE blood | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
771.4 nmol × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7658356 |
330 mg 2 times / day multiple, oral dose: 330 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
LEVOCARNITINE blood | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
779.9 nmol × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7658356 |
2 g 2 times / day multiple, oral dose: 2 g route of administration: Oral experiment type: MULTIPLE co-administered: |
LEVOCARNITINE blood | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Antagonism of doxorubicin cardiotoxicity by carnitine is specific of the L-diasteroisomer. | 1981 May |
|
| Effect of administration of carnitine on the severity of myocardial infarction induced by isoproterenol in rats. | 1986 Feb |
|
| Carnitine protection against adriamycin-induced cardiomyopathy in rats. | 1986 Feb 10 |
|
| Echocardiographic assessment of anthracycline cardiotoxicity during different therapeutic regimens. | 1987 |
|
| Carnitine deficiency associated with long-term pivampicillin treatment: the effect of a replacement therapy regime. | 1992 Nov |
|
| Modulation of ethanol-mediated CYP2E1 induction by clofibrate and L-carnitine in rat liver. | 1993 Dec |
|
| Zidovudine-induced mitochondrial myopathy is associated with muscle carnitine deficiency and lipid storage. | 1994 Apr |
|
| Effect of L-carnitine on the zidovudine-induced destruction of human myotubes. Part I: L-carnitine prevents the myotoxicity of AZT in vitro. | 1994 Jul |
|
| Muscle carnitine deficiency associated with zidovudine-induced mitochondrial myopathy. | 1994 Oct |
|
| Effect of L-carnitine supplementation on acute valproate intoxication. | 1996 Jul |
|
| L-carnitine supplementation in patients with cystic acne on isotretinoin therapy. | 1999 Nov |
|
| Long-chain hydroxydicarboxylic aciduria, carnitine depletion and acetaminophen exposure. | 2000 Mar |
|
| Molecular cloning and functional characterization of the OCTN2 transporter at the RBE4 cells, an in vitro model of the blood-brain barrier. | 2003 Apr 4 |
|
| Renal transport of organic compounds mediated by mouse organic anion transporter 3 (mOat3): further substrate specificity of mOat3. | 2004 May |
|
| Lethal cardiomyopathy in epidermolysis bullosa associated with amitriptyline. | 2005 Aug |
|
| Expression, localization, and function of the carnitine transporter octn2 (slc22a5) in human placenta. | 2005 Jan |
|
| Prediction of genotoxicity of chemical compounds by statistical learning methods. | 2005 Jun |
|
| Pivotal role of Harakiri in the induction and prevention of gentamicin-induced hearing loss. | 2005 Nov 1 |
|
| L-carnitine ameliorates doxorubicin-induced nephrotic syndrome in rats. | 2006 Aug |
|
| Effects of doxorubicin-containing chemotherapy and a combination with L-carnitine on oxidative metabolism in patients with non-Hodgkin lymphoma. | 2006 Feb |
|
| Positive regulation of hepatic carnitine palmitoyl transferase 1A (CPT1A) activities by soy isoflavones and L-carnitine. | 2006 Mar |
|
| Acute renal failure due to phenazopyridine (Pyridium) overdose: case report and review of the literature. | 2006 Nov |
|
| Carnitine deficiency aggravates carboplatin nephropathy through deterioration of energy status, oxidant/anti-oxidant balance, and inflammatory endocoids. | 2008 Dec 5 |
|
| Pharmacological analysis demonstrates dramatic alteration of D1 dopamine receptor neuronal distribution in the rat analog of L-DOPA-induced dyskinesia. | 2009 Apr 15 |
|
| Interaction between pivaloylcarnitine and L-carnitine transport into L6 cells overexpressing hOCTN2. | 2009 Aug 14 |
|
| Organic cation/carnitine transporter OCTN3 is present in astrocytes and is up-regulated by peroxisome proliferators-activator receptor agonist. | 2009 Dec |
|
| The carnitine transporter SLC22A5 is not a general drug transporter, but it efficiently translocates mildronate. | 2009 Feb |
|
| Progression of diethylnitrosamine-induced hepatic carcinogenesis in carnitine-depleted rats. | 2009 Mar 21 |
|
| Inactivation by omeprazole of the carnitine transporter (OCTN2) reconstituted in liposomes. | 2009 May 15 |
|
| Peroxisome proliferator-activated receptor alpha plays a crucial role in L-carnitine anti-apoptosis effect in renal tubular cells. | 2009 Oct |
|
| Comparative effects of captopril and l-carnitine on blood pressure and antioxidant enzyme gene expression in the heart of spontaneously hypertensive rats. | 2010 Apr 25 |
|
| Inhibition of gene expression of heart fatty acid binding protein and organic cation/carnitine transporter in doxorubicin cardiomyopathic rat model. | 2010 Aug 25 |
|
| Increased urinary losses of carnitine and decreased intramitochondrial coenzyme A in gentamicin-induced acute renal failure in rats. | 2010 Jan |
|
| The plasma carnitine concentration regulates renal OCTN2 expression and carnitine transport in rats. | 2010 Jun 10 |
|
| Selective regulation of cardiac organic cation transporter novel type 2 (OCTN2) in dilated cardiomyopathy. | 2011 Jun |
|
| The disruption of L-carnitine metabolism by aluminum toxicity and oxidative stress promotes dyslipidemia in human astrocytic and hepatic cells. | 2011 Jun 24 |
|
| L-carnitine protects against nickel-induced neurotoxicity by maintaining mitochondrial function in Neuro-2a cells. | 2011 May 15 |
|
| Bezafibrate upregulates carnitine palmitoyltransferase II expression and promotes mitochondrial energy crisis dissipation in fibroblasts of patients with influenza-associated encephalopathy. | 2011 Nov |
|
| 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 |
|
| L-Carnitine rescues ketamine-induced attenuated heart rate and MAPK (ERK) activity in zebrafish embryos. | 2012 Apr |
|
| Propionyl-L-Carnitine Enhances Wound Healing and Counteracts Microvascular Endothelial Cell Dysfunction. | 2015 |
|
| Inflammatory and fibrotic processes are involved in the cardiotoxic effect of sunitinib: Protective role of L-carnitine. | 2016 Jan 22 |
Patents
Sample Use Guides
Adults: The recommended oral dosage for adults is 990 mg two or three times a day using the 330 mg tablets, depending on clinical response. Infants and children: The recommended oral dosage for infants and children is between 50 and 100 mg/kg/day in divided doses, with a maximum of 3 g/day. Dosage should begin at 50 mg/kg/day.
Route of Administration:
Oral
| Substance Class |
Chemical
Created
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| Record UNII |
12FW2YBF04
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Validated (UNII)
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CHEMBL1516469
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