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

Molecular Formula	C7H15NO3
Molecular Weight	161.1989
Charge	0
Count

Stereochemistry	MIXED
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

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
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 supplementation on acute valproate intoxication.	1996 Jul	8681902
L-carnitine supplementation in patients with cystic acne on isotretinoin therapy.	1999 Nov	10642057
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
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
Lethal cardiomyopathy in epidermolysis bullosa associated with amitriptyline.	2005 Aug	16040888
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
Cardio-protective effects of carnitine in streptozotocin-induced diabetic rats.	2006 Jan 19	16423284
Acute renal failure due to phenazopyridine (Pyridium) overdose: case report and review of the literature.	2006 Nov	16897003
Carnitine deficiency aggravates carboplatin nephropathy through deterioration of energy status, oxidant/anti-oxidant balance, and inflammatory endocoids.	2008 Dec 5	18852009
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
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
Identification of a novel organic anion transporter mediating carnitine transport in mouse liver and kidney.	2010	20332632
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
Transcellular movement of hydroxyurea is mediated by specific solute carrier transporters.	2011 Apr	21256917
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

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).

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:12:53 GMT 2023` Edited by `admin` on `Fri Dec 15 15:12:53 GMT 2023`
Record UNII	S7UI8SM58A
Record Status	`Validated (UNII)`
Record Version

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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