Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C9H17NO4.C6H14N4O2.2ClH |
| Molecular Weight | 450.358 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.Cl.N[C@@H](CCCNC(N)=N)C(O)=O.CC(=O)O[C@H](CC([O-])=O)C[N+](C)(C)C
InChI
InChIKey=YNRSDRXTLHBJHG-DBBIGLEBSA-N
InChI=1S/C9H17NO4.C6H14N4O2.2ClH/c1-7(11)14-8(5-9(12)13)6-10(2,3)4;7-4(5(11)12)2-1-3-10-6(8)9;;/h8H,5-6H2,1-4H3;4H,1-3,7H2,(H,11,12)(H4,8,9,10);2*1H/t8-;4-;;/m10../s1
| Molecular Formula | C9H17NO4 |
| Molecular Weight | 203.2356 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
| Molecular Formula | C6H14N4O2 |
| Molecular Weight | 174.201 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| 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 |
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Target ID: CHEMBL2216739 |
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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 |
|
| 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 |
|
| Analysis of carnitine biosynthesis metabolites in urine by HPLC-electrospray tandem mass spectrometry. | 2002 Jun |
|
| Attenuation of levodopa-induced dyskinesia by normalizing dopamine D3 receptor function. | 2003 Jun |
|
| Role of L-carnitine in the prevention of acute liver damage induced by carbon tetrachloride in rats. | 2004 Mar |
|
| Carnitine: a nutritional, biosynthetic, and functional perspective. | 2004 Oct-Dec |
|
| 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 |
|
| Sodium valproate -- induced skeletal myopathy. | 2005 Mar |
|
| Pivotal role of Harakiri in the induction and prevention of gentamicin-induced hearing loss. | 2005 Nov 1 |
|
| 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 |
|
| Carnitine deficiency: a possible risk factor in paracetamol hepatotoxicity. | 2009 Feb |
|
| Peroxisome proliferator-activated receptor alpha plays a crucial role in L-carnitine anti-apoptosis effect in renal tubular cells. | 2009 Oct |
|
| 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 |
|
| Inhibition of hepatic carnitine palmitoyl-transferase I (CPT IA) by valproyl-CoA as a possible mechanism of valproate-induced steatosis. | 2010 Mar 1 |
|
| Integration of metabolomics and transcriptomics data to aid biomarker discovery in type 2 diabetes. | 2010 May |
|
| Downregulation of oxidative and nitrosative apoptotic signaling by L-carnitine in Ifosfamide-induced Fanconi syndrome rat model. | 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 |
|
| 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 |
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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Edited
Sat Dec 16 18:40:55 GMT 2023
by
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Sat Dec 16 18:40:55 GMT 2023
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| Record UNII |
DDL9STT4CE
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| Record Status |
Validated (UNII)
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| Record Version |
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