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

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
Carnitine deficiency associated with long-term pivampicillin treatment: the effect of a replacement therapy regime.	1992 Nov	1494519
Modulation of ethanol-mediated CYP2E1 induction by clofibrate and L-carnitine in rat liver.	1993 Dec	8130774
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
Differential long-term subcellular responses in heart and liver to adriamycin stress. Exogenous L-carnitine cardiac and hepatic protection.	2002 Jul	12408365
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	12644265
Attenuation of levodopa-induced dyskinesia by normalizing dopamine D3 receptor function.	2003 Jun	12740572
Role of L-carnitine in the prevention of acute liver damage induced by carbon tetrachloride in rats.	2004 Mar	14748882
Renal transport of organic compounds mediated by mouse organic anion transporter 3 (mOat3): further substrate specificity of mOat3.	2004 May	15100168
Carnitine: a nutritional, biosynthetic, and functional perspective.	2004 Oct-Dec	15363636
Expression, localization, and function of the carnitine transporter octn2 (slc22a5) in human placenta.	2005 Jan	15486076
Prediction of genotoxicity of chemical compounds by statistical learning methods.	2005 Jun	15962942
Pivotal role of Harakiri in the induction and prevention of gentamicin-induced hearing loss.	2005 Nov 1	16239342
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
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
High concentrations of stavudine impair fatty acid oxidation without depleting mitochondrial DNA in cultured rat hepatocytes.	2008 Jun	18299183
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
Inhibition of gene expression of heart fatty acid binding protein and organic cation/carnitine transporter in doxorubicin cardiomyopathic rat model.	2010 Aug 25	20470772
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
L-carnitine protects against nickel-induced neurotoxicity by maintaining mitochondrial function in Neuro-2a cells.	2011 May 15	21419151

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.

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