Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | 2C7H15NO3.C4H4O6.2H |
| Molecular Weight | 472.4846 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[H+].[H+].O[C@H]([C@@H](O)C([O-])=O)C([O-])=O.C[N+](C)(C)C[C@H](O)CC([O-])=O.C[N+](C)(C)C[C@H](O)CC([O-])=O
InChI
InChIKey=GADIJPCDIWZEMB-BTNVMJJCSA-N
InChI=1S/2C7H15NO3.C4H6O6/c2*1-8(2,3)5-6(9)4-7(10)11;5-1(3(7)8)2(6)4(9)10/h2*6,9H,4-5H2,1-3H3;1-2,5-6H,(H,7,8)(H,9,10)/t2*6-;1-,2-/m111/s1
| Molecular Formula | H |
| Molecular Weight | 1.0079 |
| Charge | 1 |
| 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 | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
| Molecular Formula | C4H4O6 |
| Molecular Weight | 148.071 |
| Charge | -2 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
Levocarnetine also known as L-carnitine is a naturally occurring substance required in mammalian energy metabolism that functions by facilitating long-chain fatty acid entry into cellular mitochondria, thereby delivering substrate for oxidation and subsequent energy production. Levocarnetine was approved by FDA for the treatment of carnetine deficiency.
Originator
Sources: http://adisinsight.springer.com/drugs/800003253www.ncbi.nlm.nih.gov/pubmed/16857830
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) |
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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 Date5.04489607E11 |
|||
| 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. |
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| 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 |
|
| Echocardiographic assessment of anthracycline cardiotoxicity during different therapeutic regimens. | 1987 |
|
| 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 |
|
| Contrasting effects of propionate and propionyl-L-carnitine on energy-linked processes in ischemic hearts. | 1994 Aug |
|
| Attenuation of levodopa-induced dyskinesia by normalizing dopamine D3 receptor function. | 2003 Jun |
|
| Renal transport of organic compounds mediated by mouse organic anion transporter 3 (mOat3): further substrate specificity of mOat3. | 2004 May |
|
| Fatty acid oxidation defects as a cause of neuromyopathic disease in infants and adults. | 2005 |
|
| Prediction of genotoxicity of chemical compounds by statistical learning methods. | 2005 Jun |
|
| Sodium valproate -- induced skeletal myopathy. | 2005 Mar |
|
| 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 |
|
| Acute renal failure due to phenazopyridine (Pyridium) overdose: case report and review of the literature. | 2006 Nov |
|
| 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 |
|
| 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 |
|
| Identification of a novel organic anion transporter mediating carnitine transport in mouse liver and kidney. | 2010 |
|
| 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 |
|
| The plasma carnitine concentration regulates renal OCTN2 expression and carnitine transport in rats. | 2010 Jun 10 |
|
| 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 |
|
| Transcellular movement of hydroxyurea is mediated by specific solute carrier transporters. | 2011 Apr |
|
| 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 mitochondrial carnitine/acylcarnitine transporter by H(2)O(2): molecular mechanism and possible implication in pathophysiology. | 2013 Apr 25 |
|
| 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
L- propionyl carnitine protected the heart against ischemia-reperfusion injury at 10 mM but did not exert significant protection at 1 mM concentration. Protection provided by 10 mM L-propionyl
carnitine was stronger than that of D-propionyl carnitine and similar to that of deferoxamine at 100 times the concentration.
| Substance Class |
Chemical
Created
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admin
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Wed Jul 05 23:50:09 UTC 2023
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| Record UNII |
4D8F2Q45LQ
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1364375
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PARENT -> SALT/SOLVATE |
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