Levocarnitine

Levocarnitine

Cat Number
API541151
CAS Number
541-15-1

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CAS Number
541-15-1
EINECS
208-768-0
Storage
Store at room temperature
Synonyms
ME3-GAMMA-ABU(BETA-HYDROXY)-OH; (R)-BETA-HYDROXY-GAMMA-(TRIMETHYLAMMONIO)BUTYRATE; (R)-3-HYDROXY-4-(TRIMETHYLAMMONIO)BUTYRATE; L-Carnitine; Tartrate; L-carnitine; Vitamin BT; L-ca greatrnitine; L-ctheirrnitine
Molecular Formula
C7H15NO3
Molecular Weight
161.2
Smiles
C[N+](C)(C)C[C@@H](CC(=O)[O-])O
Appearance
White crystalline hygroscopic powder
Melting Point
197-212℃
Boiling Point
287.5℃ (Rough Estimate)
pKa
3.8
General Description
Levocarnitine (L-carnitine) is a naturally occurring amino acid derivative essential for mitochondrial fatty acid oxidation. It is available for replacement therapy in primary and secondary carnitine deficiencies. The compound is synthesized endogenously in the liver and kidneys but may become depleted in certain disease states.
Mechanism of Action
Levocarnitine facilitates the transport of long-chain fatty acids across the inner mitochondrial membrane via the carnitine shuttle system. It forms esters with acyl-CoA molecules, enabling their transfer into the matrix where beta-oxidation occurs. The drug also buffers the acyl-CoA to free CoA ratio, preventing accumulation of toxic acyl-CoA intermediates.
Application
Levocarnitine is indicated for the treatment of primary systemic carnitine deficiency, a rare genetic disorder of the carnitine transporter. It is also used for secondary deficiency in patients with end-stage renal disease on hemodialysis, those receiving valproic acid therapy, or individuals with organic acidurias. Intravenous administration is reserved for acute metabolic crises, while oral maintenance therapy prevents cardiomyopathy, myopathy, and hypoglycemia in deficient patients.

L‑carnitine transports long‑chain fatty acids into mitochondria for β‑oxidation; its acetylated derivative acetyl‑L‑carnitine (ALCAR) can provide acetyl groups for energy, acetylcholine synthesis, and incorporation into glutamate, GABA, and lipids. Preclinical studies show that both compounds improve energy status, reduce oxidative stress, and prevent cell death in models of adult, neonatal, and pediatric brain injury. In rat pups, ALCAR given after brain injury improved long‑term functional outcomes including memory. The authors call for more research to explore their potential for protecting the developing brain, where therapies are urgently needed.

Fig. 1 L-Carnitine biosynthesis in humans. (Ferreira GC, McKenna MC, 2017) Fig. 1 L-Carnitine biosynthesis in humans. (Ferreira GC, McKenna MC, 2017)

References

  1. Ferreira GC, McKenna MC. L-Carnitine and Acetyl-L-carnitine Roles and Neuroprotection in Developing Brain. Neurochem Res. 2017;42(6):1661-1675.

In a 12‑month randomized controlled trial, maintenance hemodialysis patients receiving levocarnitine 1000 mg thrice weekly after dialysis maintained target hemoglobin and hematocrit levels while gradually reducing erythropoiesis‑stimulating agent (ESA) doses. At 6 and 12 months, the ESA dose and erythropoietin responsiveness index were significantly lower in the levocarnitine group than at baseline and, at 12 months, lower than in the control group. Levocarnitine improves ESA responsiveness, potentially reducing the required dose in renal anemia.

Fig. 2 Changes in Hb values from baseline to 6 and 12 months in the treatment and control groups with a comparison between the 2 groups. (Maruyama T, <i>et al</i>., 2017) Fig. 2 Changes in Hb values from baseline to 6 and 12 months in the treatment and control groups with a comparison between the 2 groups. (Maruyama T, et al., 2017)

References

  1. Maruyama T, et al. Levocarnitine Injections Decrease the Need for Erythropoiesis-Stimulating Agents in Hemodialysis Patients with Renal Anemia. Cardiorenal Med. 2017;7(3):188-197.

Does Levocarnitine require protection from light during storage?

It is relatively stable, but prolonged light exposure may cause slight degradation. Store in light-resistant containers in a cool, dry place.

What is the recommended storage temperature for Levocarnitine?

Store at controlled room temperature (15-25°C). It is thermally stable, but avoid excessive heat above 40°C, which can accelerate degradation to trimethylamine.

Is Levocarnitine highly hygroscopic, and how does this affect stability?

Yes, it is extremely hygroscopic and readily absorbs moisture, leading to deliquescence. It must be stored in tightly sealed, moisture-proof containers and opened only in low-humidity environments.

How is the impurity trimethylamine monitored during stability?

This degradation product (responsible for fishy odor) is quantified using a validated GC headspace method, ensuring it remains below acceptable limits.
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