Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C10H19NO4.C2H5NO2 |
| Molecular Weight | 292.3288 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
NCC(O)=O.CCC(=O)O[C@H](CC([O-])=O)C[N+](C)(C)C
InChI
InChIKey=UXXCWGVLNFBBAY-DDWIOCJRSA-N
InChI=1S/C10H19NO4.C2H5NO2/c1-5-10(14)15-8(6-9(12)13)7-11(2,3)4;3-1-2(4)5/h8H,5-7H2,1-4H3;1,3H2,(H,4,5)/t8-;/m1./s1
| Molecular Formula | C2H5NO2 |
| Molecular Weight | 75.0666 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | C10H19NO4 |
| Molecular Weight | 217.2622 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
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) |
|||
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) |
|||
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 |
|---|---|---|
| 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 |
|
| Antiradical effects in L-propionyl carnitine protection of the heart against ischemia-reperfusion injury: the possible role of iron chelation. | 1992 Aug 1 |
|
| Carnitine deficiency associated with long-term pivampicillin treatment: the effect of a replacement therapy regime. | 1992 Nov |
|
| Zidovudine-induced mitochondrial myopathy is associated with muscle carnitine deficiency and lipid storage. | 1994 Apr |
|
| L-carnitine supplementation in patients with cystic acne on isotretinoin therapy. | 1999 Nov |
|
| Long-chain hydroxydicarboxylic aciduria, carnitine depletion and acetaminophen exposure. | 2000 Mar |
|
| Differential long-term subcellular responses in heart and liver to adriamycin stress. Exogenous L-carnitine cardiac and hepatic protection. | 2002 Jul |
|
| Analysis of carnitine biosynthesis metabolites in urine by HPLC-electrospray tandem mass spectrometry. | 2002 Jun |
|
| 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 |
|
| Role of L-carnitine in the prevention of acute liver damage induced by carbon tetrachloride in rats. | 2004 Mar |
|
| Renal transport of organic compounds mediated by mouse organic anion transporter 3 (mOat3): further substrate specificity of mOat3. | 2004 May |
|
| Carnitine: a nutritional, biosynthetic, and functional perspective. | 2004 Oct-Dec |
|
| Fatty acid oxidation defects as a cause of neuromyopathic disease in infants and adults. | 2005 |
|
| 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 |
|
| Ammonia-mediated LTP inhibition: effects of NMDA receptor antagonists and L-carnitine. | 2005 Nov |
|
| Pivotal role of Harakiri in the induction and prevention of gentamicin-induced hearing loss. | 2005 Nov 1 |
|
| Involvement of recognition and interaction of carnitine transporter in the decrease of L-carnitine concentration induced by pivalic acid and valproic acid. | 2006 Aug |
|
| Effects of doxorubicin-containing chemotherapy and a combination with L-carnitine on oxidative metabolism in patients with non-Hodgkin lymphoma. | 2006 Feb |
|
| High concentrations of stavudine impair fatty acid oxidation without depleting mitochondrial DNA in cultured rat hepatocytes. | 2008 Jun |
|
| L-carnitine mediates protection against DNA damage in lymphocytes of aged rats. | 2009 Apr |
|
| Interaction between pivaloylcarnitine and L-carnitine transport into L6 cells overexpressing hOCTN2. | 2009 Aug 14 |
|
| The carnitine transporter SLC22A5 is not a general drug transporter, but it efficiently translocates mildronate. | 2009 Feb |
|
| Vincristine-induced peripheral neuropathy in a neonate with congenital acute lymphoblastic leukemia. | 2010 Apr |
|
| 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 |
|
| Valproate-induced hyperammonemic encephalopathy, rapidly improved by i.v. carnitine and glucose/thiamine. | 2010 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 |
|
| 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 |
|
| L-Carnitine rescues ketamine-induced attenuated heart rate and MAPK (ERK) activity in zebrafish embryos. | 2012 Apr |
|
| Changes in the levels of l-carnitine, acetyl-l-carnitine and propionyl-l-carnitine are involved in perfluorooctanoic acid induced developmental cardiotoxicity in chicken embryo. | 2016 Dec |
|
| Regression of fibrosis/cirrhosis by Glycine propionyl-l-carnitine treatment in d-Galactosamine induced chronic liver damage. | 2016 Dec 25 |
|
| 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
by
admin
on
Edited
Sat Dec 16 16:58:58 GMT 2023
by
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on
Sat Dec 16 16:58:58 GMT 2023
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| Record UNII |
8KVN59D5FL
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| Record Status |
Validated (UNII)
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| Record Version |
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Common Name | English | ||
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Common Name | English |
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DSLD |
3179 (Number of products:106)
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PARENT -> SALT/SOLVATE |
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PARENT -> SALT/SOLVATE |
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