DL-CARNITINE

First approved in 2009

Details

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

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=PHIQHXFUZVPYII-UHFFFAOYSA-N

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

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16924874

L-carnitine (L-beta-hydroxy-gamma-N,N,N-trimethylaminobutyric acid) is conditionally necessary for mitochondrial transport and metabolism of long-chain fatty acids, and thus for myocardial energetic metabolism. D-carnitine is not biologically active and might interfere with proper utilization of the L isomer, and so there are claims that the racemic mixture (DL-carnitine) should be avoided. The pharmacological effects of carnitine are stereospecific: L-carnitine was effective in various animal and clinical studies, while D- and DL-carnitine was found to be ineffective or even toxic to some cells and tissues, such as muscle cells and the myocardium. DL-carnitine caused symptoms of myasthenia and cardiac arrhythmias, which disappeared after L-carnitine administration.

CNS Activity

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

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

in rat: supplemented with dl-carnitine (DLC) (1.2 mmol . kg-1. d-1)

Route of Administration: Oral

In Vitro Use Guide

Using rat phrenic nerve diaphragm preparations indirectly and directly stimulated with high rate pulses, D-carnitine (30 and 60 micro M), L-carnitine (60 micro M) and DL-carnitine (60 micro M) were shown to induce tetanic fade (D-carnitine = 19.7 +/- 3.1%, N = 6; L-carnitine = 16.6 +/- 2.4%, N = 6; DL-carnitine = 14.9 +/- 2.1%, N = 6) without any reduction of maximal tetanic tension. It was shown, that tetanic fade induced by L- and DL-carnitine was antagonized by choline (60 micro M).

Name

Type

Language

CARNITINE

Preferred Name

English

DL-CARNITINE

Common Name

English

CARNITINE, DL-

Common Name

English

Carnitine, (+/-)-

Common Name

English

CARNITINE [MART.]

Common Name

English

CARNITINE DL-FORM [MI]

Common Name

English

CARNITINE [INCI]

Common Name

English

CARNITINE [VANDF]

Common Name

English

Carnitine [WHO-DD]

Common Name

English

carnitine [INN]

Common Name

English

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

Common Name

English

NSC-757390

Code

English

Classification Tree Code System Code

LOINC

53096-4