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

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	MOL RATIO 1 MOL RATIO (average)

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

Description

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	Substrate 661
Carnitine O-palmitoyltransferase 2, mitochondrial 13	Substrate 661
Carnitine O-acetyltransferase 18	Substrate 661
Mitochondrial carnitine/acylcarnitine carrier protein 13	Substrate 661
Oxidative Stress 160	Inhibitor 8,297
Carnitine O-palmitoyltransferase 1, muscle isoform 15	Substrate 661
Oxidative phosphorylation 15	Activator 1,430

Conditions

Condition	Modality	Highest Phase	Product
Systemic primary carnitine deficiency 13	Primary	Approved 8,429	CARNITOR
Peripheral arterial occlusive disorders 14	Primary	Approved 8,429	Dromos
Ulcerative colitis 123	Primary	Phase III 656	Unknown
Congestive heart failure 54	Primary	Phase III 656	Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
79.2 nmol/mL	330 mg 2 times / day multiple, oral		LEVOCARNITINE blood	Homo sapiens
80.3 nmol/mL	2 g 2 times / day multiple, oral		LEVOCARNITINE blood	Homo sapiens

AUC

Value	Dose	Co-administered	Analyte	Population
771.4 nmol × h/mL	330 mg 2 times / day multiple, oral		LEVOCARNITINE blood	Homo sapiens
779.9 nmol × h/mL	2 g 2 times / day multiple, oral		LEVOCARNITINE blood	Homo sapiens

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
		CYP2E1 128

Drug as perpetrator

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Target	Modality	Activity	Metabolite	Clinical evidence
CYP2E1 970	inducer 1,573	yes

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Sourcing

Sourcing

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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

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PubMed

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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
Antiradical effects in L-propionyl carnitine protection of the heart against ischemia-reperfusion injury: the possible role of iron chelation.	1992 Aug 1	1321584

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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.