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Details

Stereochemistry ABSOLUTE
Molecular Formula C10H19NO4
Molecular Weight 217.2622
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LEVOCARNITINE PROPIONATE

SMILES

CCC(=O)O[C@H](CC([O-])=O)C[N+](C)(C)C

InChI

InChIKey=UFAHZIUFPNSHSL-MRVPVSSYSA-N
InChI=1S/C10H19NO4/c1-5-10(14)15-8(6-9(12)13)7-11(2,3)4/h8H,5-7H2,1-4H3/t8-/m1/s1

HIDE SMILES / InChI
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.

CNS Activity

Curator's Comment: Known to be CNS penetrant in model animals. Human data not available.

Originator

Sources: www.ncbi.nlm.nih.gov/pubmed/16857830http://adisinsight.springer.com/drugs/800003253

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
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)
Target ID: P43155
Gene ID: 1384.0
Gene Symbol: CRAT
Target Organism: Homo sapiens (Human)
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: WP623
Sources: DOI: 10.1201/b17092-12
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
CARNITOR

Approved Use

CARNITOR (levocarnitine) is indicated in the treatment of primary systemic carnitine deficiency.

Launch Date

1985
Primary
Dromos

Approved Use

It is indicated for patients with peripheral arterial occlusive disorders and for exercise intolerance enchancement in patients with chronic congestive heart failure.
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
79.2 nmol/mL
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
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

AUC

ValueDoseCo-administeredAnalytePopulation
771.4 nmol × h/mL
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
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
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
yes
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
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
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
Lethal cardiomyopathy in epidermolysis bullosa associated with amitriptyline.
2005 Aug
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
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
Cardio-protective effects of carnitine in streptozotocin-induced diabetic rats.
2006 Jan 19
Positive regulation of hepatic carnitine palmitoyl transferase 1A (CPT1A) activities by soy isoflavones and L-carnitine.
2006 Mar
Mechanism of the inhibitory effect of zwitterionic drugs (levofloxacin and grepafloxacin) on carnitine transporter (OCTN2) in Caco-2 cells.
2006 Nov
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
Carnitine deficiency aggravates carboplatin nephropathy through deterioration of energy status, oxidant/anti-oxidant balance, and inflammatory endocoids.
2008 Dec 5
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
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
Carnitine deficiency: a possible risk factor in paracetamol hepatotoxicity.
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
Identification of a novel organic anion transporter mediating carnitine transport in mouse liver and kidney.
2010
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 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
Valproate-induced hyperammonemic encephalopathy, rapidly improved by i.v. carnitine and glucose/thiamine.
2010 Jun
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
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
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
L-Carnitine rescues ketamine-induced attenuated heart rate and MAPK (ERK) activity in zebrafish embryos.
2012 Apr
Inhibition of mitochondrial carnitine/acylcarnitine transporter by H(2)O(2): molecular mechanism and possible implication in pathophysiology.
2013 Apr 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
Human neuroblastoma or human astrocytoma cells were exposed to 100 nM (20 ug levocarnetine hydrochloride/L) to 100 uM (20 mg levocarnetine hydrochloride/L). At these concentrations levocarnetine produced significant increases in mitochondrial function.
Name Type Language
LEVOCARNITINE PROPIONATE
MART.   WHO-DD  
Common Name English
Levocarnitine propionate [WHO-DD]
Common Name English
LEVOCARNITINE PROPIONATE [MART.]
Common Name English
(2R)-3-CARBOXY-N,N,N-TRIMETHYL-2-(PROPANOYLOXY)PROPAN-1-AMINIUM
Systematic Name English
L-CARNITINE PROPIONATE
Systematic Name English
PROPIONYL-L-CARNITINE
Systematic Name English
CARNITINE PROPIONATE, (-)-
Systematic Name English
Classification Tree Code System Code
DSLD 1586 (Number of products:24)
Created by admin on Fri Dec 15 18:55:29 GMT 2023 , Edited by admin on Fri Dec 15 18:55:29 GMT 2023
Code System Code Type Description
DRUG CENTRAL
4040
Created by admin on Fri Dec 15 18:55:29 GMT 2023 , Edited by admin on Fri Dec 15 18:55:29 GMT 2023
PRIMARY
HSDB
7589
Created by admin on Fri Dec 15 18:55:29 GMT 2023 , Edited by admin on Fri Dec 15 18:55:29 GMT 2023
PRIMARY
SMS_ID
100000091165
Created by admin on Fri Dec 15 18:55:29 GMT 2023 , Edited by admin on Fri Dec 15 18:55:29 GMT 2023
PRIMARY
PUBCHEM
188824
Created by admin on Fri Dec 15 18:55:29 GMT 2023 , Edited by admin on Fri Dec 15 18:55:29 GMT 2023
PRIMARY
CAS
99581-18-7
Created by admin on Fri Dec 15 18:55:29 GMT 2023 , Edited by admin on Fri Dec 15 18:55:29 GMT 2023
ALTERNATIVE
EVMPD
SUB26424
Created by admin on Fri Dec 15 18:55:29 GMT 2023 , Edited by admin on Fri Dec 15 18:55:29 GMT 2023
PRIMARY
CAS
20064-19-1
Created by admin on Fri Dec 15 18:55:29 GMT 2023 , Edited by admin on Fri Dec 15 18:55:29 GMT 2023
PRIMARY
FDA UNII
0HU2UI27HF
Created by admin on Fri Dec 15 18:55:29 GMT 2023 , Edited by admin on Fri Dec 15 18:55:29 GMT 2023
PRIMARY
EPA CompTox
DTXSID40173883
Created by admin on Fri Dec 15 18:55:29 GMT 2023 , Edited by admin on Fri Dec 15 18:55:29 GMT 2023
PRIMARY