LEVOCARNITINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C7H15NO3
Molecular Weight	161.1989
Optical Activity	( - )
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=PHIQHXFUZVPYII-ZCFIWIBFSA-N

InChI=1S/C7H15NO3/c1-8(2,3)5-6(9)4-7(10)11/h6,9H,4-5H2,1-3H3/t6-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C7H15NO3
Molecular Weight	161.1989
Charge	0
Count

Stereochemistry	EPIMERIC
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/018948s026,019257s012,020182s013lbl.pdfhttps://www.ncbi.nlm.nih.gov/pubmed/22333562 | https://www.ncbi.nlm.nih.gov/pubmed/9534023 | DOI: 10.1201/b17092-12

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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Carnitine O-palmitoyltransferase 1, liver isoform 15 Target ID: P50416 Gene ID: 1374.0 Gene Symbol: CPT1A Target Organism: Homo sapiens (Human) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/018948s026,019257s012,020182s013lbl.pdf	Substrate 661
Carnitine O-palmitoyltransferase 2, mitochondrial 13 Target ID: P23786 Gene ID: 1376.0 Gene Symbol: CPT2 Target Organism: Homo sapiens (Human) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/018948s026,019257s012,020182s013lbl.pdf	Substrate 661
Carnitine O-acetyltransferase 18 Target ID: P43155 Gene ID: 1384.0 Gene Symbol: CRAT Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/21537157	Substrate 661
Mitochondrial carnitine/acylcarnitine carrier protein 13 Target ID: O43772 Gene ID: 788.0 Gene Symbol: SLC25A20 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/21537157	Substrate 661
Oxidative Stress 160 Target ID: WP408 Sources: DOI: 10.1201/b17092-12	Inhibitor 8297
Carnitine O-palmitoyltransferase 1, muscle isoform 15 Target ID: CHEMBL2216739 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2031869 \| DOI: 10.1201/b17092-12	Substrate 661
Oxidative phosphorylation 15 Target ID: WP623 Sources: DOI: 10.1201/b17092-12	Activator 1430

Conditions

Condition	Modality	Highest Phase	Product
Systemic primary carnitine deficiency 13 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/018948s026,019257s012,020182s013lbl.pdf	Primary	Approved 8429	CARNITOR Approved Use CARNITOR (levocarnitine) is indicated in the treatment of primary systemic carnitine deficiency. Launch Date 1985
Peripheral arterial occlusive disorders 14 Sources: http://adisinsight.springer.com/drugs/800003253	Primary	Approved 8429	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.
Ulcerative colitis 123 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21929562	Primary	Phase III 656	Unknown Approved Use Unknown
Congestive heart failure 54 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1737667 https://www.ncbi.nlm.nih.gov/pubmed/1493661	Primary	Phase III 656	Unknown Approved Use Unknown

C_max

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

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
		CYP2E1 128

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
CYP2E1 970	inducer 1573 Sources: https://pubmed.ncbi.nlm.nih.gov/8130774/	yes

Sourcing

Vendor/Aggregator	ID	URL
3B Scientific (Wuhan) Corp	3B2-0707	http://www.3bsc.com/index/pro_info.php?id=20063
3B Scientific (Wuhan) Corp	3B1-00224	http://www.3bsc.com/index/pro_info.php?id=20436
3B Scientific (Wuhan) Corp	3B3-006066	http://www.3bsc.com/index/pro_info.php?id=27979
AEchem Scientific Corp., USA	AE065382	https://www.aechemsc.com/info_products/AE065382.php
AHH Chemical co.,ltd	API-1679	http://www.ahhchemical.com/product/API-1679.html
AbMole Bioscience	M3580	http://www.abmole.com/products/l-carnitine.html
Achemtek	0101-001291	http://www.achemtek.com/541-15-1
Acorn PharmaTech	ACN-038319	http://www.acornpharmatech.com/
Acros Organics	AC241040010	https://www.fishersci.com/shop/products/l-carnitine-99-acros-organics-1/AC241040010
Acros Organics	AC241040100	https://www.fishersci.com/shop/products/l-carnitine-99-acros-organics-1/AC241040100
Acros Organics	AC241040500	https://www.fishersci.com/shop/products/l-carnitine-99-acros-organics/AC241040500
Active Biopharma	ABP000696	http://www.activebiopharma.com/541-15-1
Alfa Aesar	A17618	https://www.alfa.com/en/catalog/A17618/
Anward	ANW-31960	http://www.anward.com/pro_result/24876
ApexBio Technology	N1935	http://www.apexbt.com/l-carnitine-inner-salt-14559.html
Ark Pharma Scientific Limited	N-2975	http://www.arkpharmtech.com/product/244514.html
Aronis	ARONIS24315	http://www.aronis.ru/store/index.php?main_page=product_info&cPath=1&products_id=1451
Aurora Fine Chemicals LLC	K02.098.714	http://online.aurorafinechemicals.com/info?ID=K02.098.714
Avantor Inc	200012-980	https://us.vwr.com/store/product/18600933/l-carnitine
Avantor Inc	700007-570	https://us.vwr.com/store/product/9581406/l-carnitine-free-base-97
Avantor Inc	700007-572	https://us.vwr.com/store/product/9581406/l-carnitine-free-base-97
Avantor Inc	700007-574	https://us.vwr.com/store/product/9581406/l-carnitine-free-base-97
Avantor Inc	700007-578	https://us.vwr.com/store/product/9581406/l-carnitine-free-base-97
BLD Pharm	BD34022	http://www.bldpharm.com/products/541-15-1.html
BioSynth	C-1985	http://www.biosynth.com/index.asp?topic_id=97&g=19&m=249&feld=katno&wert=C-1985
CSNpharm	CSN16390	https://www.csnpharm.com/products/l-carnitine.html
Capot Chemical	5901	http://www.capotchem.com/en/5901.htm
Capot Chemical	PubChem5901	http://www.capotchem.com/en/5901.htm
Chem Scene	CS-2495	http://www.chemscene.com/541-15-1.html
ChemFaces	CFN99739	http://www.chemfaces.com/natural/L-Carnitine-inner-salt-CFN99739.html
ChemMol	1030424	http://www.chemmol.com/chemmol/1030424.html
ChemMol	80101467	http://www.chemmol.com/chemmol/80101467.html
ChemMol	99088982	http://www.chemmol.com/chemmol/99088982.html
Chemspace	CSSB00000004043	https://chem-space.com/CSSB00000004043
China MainChem Co., Ltd	MS541-15-1	https://www.mainchem.com/product/l-carnitine/
Chiralblock Biosciences	CB10390	http://www.chiralblock.com/products/541-15-1.html
Hairui	HR134980	http://www.hairuichem.com/en/product/541-15-1.html
LGC Standards	DRE-A11045500AL-100	https://www.lgcstandards.com/US/en/p/DRE-A11045500AL-100
LGC Standards	DRE-C11045500	https://www.lgcstandards.com/US/en/p/DRE-C11045500
Lab Network	LN00195276	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00195276
MedChem Express	HY-B0399	https://www.medchemexpress.com/l-carnitine.html
Oakwood	448663	http://www.oakwoodchemical.com/ProductsList.aspx?CategoryID=-2&txtSearch=197711&ExtHyperLink=1
Parchem	17046	http://www.parchem.com/chemical-supplier-distributor/L-Carnitine-007046.aspx
Sigma-Aldrich	L0399900_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/l0399900?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	PHR1569_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/phr1569?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	C0158_SIGMA	https://www.sigmaaldrich.com/catalog/product/sigma/c0158?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	1359903_USP	https://www.sigmaaldrich.com/catalog/product/usp/1359903?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
TCI (Tokyo Chemical Industry)	C0049	http://www.tcichemicals.com/eshop/en/us/commodity/C0049/index.html
TripleBond	CC0198	http://www.triplebond-canada.com/prod/1212/
VladaChem	VL141148	https://www.vladachem.com/product.php?products=541-15-1
VladaChem	VL265638-1G	https://www.vladachem.com/product.php?products=541-15-1
Watanabe Chemical Ind.	H00050	https://www.watanabechem.co.jp/en/search/details.php?code=H00050
abcr GmbH	AB114595	http://www.abcr.com/shop/en/AB114595
abcr GmbH	AB548630	http://www.abcr.com/shop/en/AB548630
eNovation Chemicals	D676290	https://www.enovationchem.com/ProductDetails.asp?ProductID=D676290
eNovation Chemicals	D765946	https://www.enovationchem.com/ProductDetails.asp?ProductID=D765946
eNovation Chemicals	D916294	https://www.enovationchem.com/ProductDetails.asp?ProductID=D916294
eNovation Chemicals	D961002	https://www.enovationchem.com/ProductDetails.asp?ProductID=D961002
iChemical	EBD2197949	http://www.ichemical.com/products/541-15-1.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs

PubMed

Title	Date	PubMed
Antagonism of doxorubicin cardiotoxicity by carnitine is specific of the L-diasteroisomer.	1981 May	7260239
Effect of administration of carnitine on the severity of myocardial infarction induced by isoproterenol in rats.	1986 Feb	3964138
Carnitine protection against adriamycin-induced cardiomyopathy in rats.	1986 Feb 10	3945174
Echocardiographic assessment of anthracycline cardiotoxicity during different therapeutic regimens.	1987	3474215
Modulation of ethanol-mediated CYP2E1 induction by clofibrate and L-carnitine in rat liver.	1993 Dec	8130774
Zidovudine-induced mitochondrial myopathy is associated with muscle carnitine deficiency and lipid storage.	1994 Apr	8154877
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	7518879
Muscle carnitine deficiency associated with zidovudine-induced mitochondrial myopathy.	1994 Oct	7944307
Effect of L-carnitine supplementation on acute valproate intoxication.	1996 Jul	8681902
Lethal cardiomyopathy in epidermolysis bullosa associated with amitriptyline.	2005 Aug	16040888
Pivotal role of Harakiri in the induction and prevention of gentamicin-induced hearing loss.	2005 Nov 1	16239342
L-carnitine ameliorates doxorubicin-induced nephrotic syndrome in rats.	2006 Aug	16889571
Involvement of recognition and interaction of carnitine transporter in the decrease of L-carnitine concentration induced by pivalic acid and valproic acid.	2006 Aug	16826461
Effects of doxorubicin-containing chemotherapy and a combination with L-carnitine on oxidative metabolism in patients with non-Hodgkin lymphoma.	2006 Feb	16283381
Cardio-protective effects of carnitine in streptozotocin-induced diabetic rats.	2006 Jan 19	16423284
Positive regulation of hepatic carnitine palmitoyl transferase 1A (CPT1A) activities by soy isoflavones and L-carnitine.	2006 Mar	16362726
Mechanism of the inhibitory effect of zwitterionic drugs (levofloxacin and grepafloxacin) on carnitine transporter (OCTN2) in Caco-2 cells.	2006 Nov	16928358
Acute renal failure due to phenazopyridine (Pyridium) overdose: case report and review of the literature.	2006 Nov	16897003
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	18762717
Carnitine deficiency aggravates carboplatin nephropathy through deterioration of energy status, oxidant/anti-oxidant balance, and inflammatory endocoids.	2008 Dec 5	18852009
High concentrations of stavudine impair fatty acid oxidation without depleting mitochondrial DNA in cultured rat hepatocytes.	2008 Jun	18299183
L-carnitine mediates protection against DNA damage in lymphocytes of aged rats.	2009 Apr	18629605
Pharmacological analysis demonstrates dramatic alteration of D1 dopamine receptor neuronal distribution in the rat analog of L-DOPA-induced dyskinesia.	2009 Apr 15	19369551
Interaction between pivaloylcarnitine and L-carnitine transport into L6 cells overexpressing hOCTN2.	2009 Aug 14	19539806
Organic cation/carnitine transporter OCTN3 is present in astrocytes and is up-regulated by peroxisome proliferators-activator receptor agonist.	2009 Dec	19735737
The carnitine transporter SLC22A5 is not a general drug transporter, but it efficiently translocates mildronate.	2009 Feb	18981167
Carnitine deficiency: a possible risk factor in paracetamol hepatotoxicity.	2009 Feb	18597074
Progression of diethylnitrosamine-induced hepatic carcinogenesis in carnitine-depleted rats.	2009 Mar 21	19294768
Inactivation by omeprazole of the carnitine transporter (OCTN2) reconstituted in liposomes.	2009 May 15	19041296
Peroxisome proliferator-activated receptor alpha plays a crucial role in L-carnitine anti-apoptosis effect in renal tubular cells.	2009 Oct	19491382
Identification of a novel organic anion transporter mediating carnitine transport in mouse liver and kidney.	2010	20332632
Vincristine-induced peripheral neuropathy in a neonate with congenital acute lymphoblastic leukemia.	2010 Apr	20216233
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	20123095
Inhibition of gene expression of heart fatty acid binding protein and organic cation/carnitine transporter in doxorubicin cardiomyopathic rat model.	2010 Aug 25	20470772
Increased urinary losses of carnitine and decreased intramitochondrial coenzyme A in gentamicin-induced acute renal failure in rats.	2010 Jan	19737869
Valproate-induced hyperammonemic encephalopathy, rapidly improved by i.v. carnitine and glucose/thiamine.	2010 Jun	20163200
The plasma carnitine concentration regulates renal OCTN2 expression and carnitine transport in rats.	2010 Jun 10	20303936
Inhibition of hepatic carnitine palmitoyl-transferase I (CPT IA) by valproyl-CoA as a possible mechanism of valproate-induced steatosis.	2010 Mar 1	19854160
Integration of metabolomics and transcriptomics data to aid biomarker discovery in type 2 diabetes.	2010 May	20567778
Transcellular movement of hydroxyurea is mediated by specific solute carrier transporters.	2011 Apr	21256917
Selective regulation of cardiac organic cation transporter novel type 2 (OCTN2) in dilated cardiomyopathy.	2011 Jun	21641380
The disruption of L-carnitine metabolism by aluminum toxicity and oxidative stress promotes dyslipidemia in human astrocytic and hepatic cells.	2011 Jun 24	21439360
L-carnitine protects against nickel-induced neurotoxicity by maintaining mitochondrial function in Neuro-2a cells.	2011 May 15	21419151
Bezafibrate upregulates carnitine palmitoyltransferase II expression and promotes mitochondrial energy crisis dissipation in fibroblasts of patients with influenza-associated encephalopathy.	2011 Nov	21816645
Downregulation of oxidative and nitrosative apoptotic signaling by L-carnitine in Ifosfamide-induced Fanconi syndrome rat model.	2012	23213347
Inhibition of gene expression of organic cation/carnitine transporter and antioxidant enzymes in oxazaphosphorines-induced acute cardiomyopathic rat models.	2012	22701146
The protection role of heat shock protein 70 (HSP-70) in the testes of cadmium-exposed rats.	2012	22359436
L-Carnitine rescues ketamine-induced attenuated heart rate and MAPK (ERK) activity in zebrafish embryos.	2012 Apr	22027688
Inhibition of mitochondrial carnitine/acylcarnitine transporter by H(2)O(2): molecular mechanism and possible implication in pathophysiology.	2013 Apr 25	23402788
Inflammatory and fibrotic processes are involved in the cardiotoxic effect of sunitinib: Protective role of L-carnitine.	2016 Jan 22	26581635

Patents

Sample Use Guides

In Vivo Use Guide

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

In Vitro Use Guide

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.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 15:52:46 GMT 2023` Edited by `admin` on `Sat Dec 16 15:52:46 GMT 2023`
Record UNII	0G389FZZ9M
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LEVOCARNITINE

Official Name

English

L-CARNITINE

Systematic Name

English

LEVOCARNITINE [HSDB]

Common Name

English

LEVOCARNITINE [USAN]

Common Name

English

LEVOCARNITINE [MART.]

Common Name

English

(3R)-3-HYDROXY-4-(TRIMETHYLAMMONIO)BUTANOATE

Systematic Name

English

LEVOCARNITINE [VANDF]

Common Name

English

CARNITINE, L-

Systematic Name

English

LEVOCARNITINE [USP-RS]

Common Name

English

CARNITOR

Brand Name

English

levocarnitine [INN]

Common Name

English

Levocarnitine [WHO-DD]

Common Name

English

NSC-759132

Code

English

LEVOCARNITINE [ORANGE BOOK]

Common Name

English

LEVOCARNITINE [JAN]

Common Name

English

1-PROPANAMINIUM, 3-CARBOXY-2-HYDROXY-N,N,N-TRIMETHYL-, HYDROXIDE, INNER SALT, (R)-

Common Name

English

CARNITINE, (-)-

Systematic Name

English

L-CARNITINE [VANDF]

Common Name

English

L-CARNITINE [FCC]

Common Name

English

CARNITINE [MI]

Common Name

English

LEVOCARNITINE [EP MONOGRAPH]

Common Name

English

(L-3-CARBOXY-2-HYDROXYPROPYL)TRIMETHYLAMMONIUM HYDROXIDE, INNER SALT

Common Name

English

LEVOCARNITINE [USP MONOGRAPH]

Common Name

English

Classification Tree Code System Code

NDF-RT

N0000006688