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Details

Stereochemistry RACEMIC
Molecular Formula C9H17NO4.ClH
Molecular Weight 239.697
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ACETYLCARNITINE HYDROCHLORIDE, (±)-

SMILES

Cl.CC(=O)OC(CC([O-])=O)C[N+](C)(C)C

InChI

InChIKey=JATPLOXBFFRHDN-UHFFFAOYSA-N
InChI=1S/C9H17NO4.ClH/c1-7(11)14-8(5-9(12)13)6-10(2,3)4;/h8H,5-6H2,1-4H3;1H

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C9H17NO4
Molecular Weight 203.2356
Charge 0
Count
Stereochemistry MIXED
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

L-acetylcarnitine or acet-L-carnitine, a compound, naturally produced by the body, is necessary for fatty-acid metabolism and energy production. It is often taken as a dietary supplement. The mechanisms of action of acetylcarnitine have not been fully elucidated, but it seems that the main role of acetylcarnitine is to donate an acetyl group during fatty acid metabolism to help transport fatty acids, such as acetyl CoA, into the mitochondrial matrix where fatty acid metabolism occurs. L-acetylcarnitine is an investigational drug, which is approved in some countries, for example in Italy for diabetic neuropathy. Phase IV of clinical trials have revealed, that it also effective agent to treat the Alzheimer's disease. In contrary, the efficacy of L-acetylcarnitine as a prophylaxis in migraine patients did not provide evidence of benefit for efficacy. Besides, Acetyl-L-carnitine was in clinical trial Phase III to investigate its efficacy in the treatment of peripheral sensory neuropathy that anti-cancer chemotherapeutics induce. Recently published article unexpectedly discovered that this drug increased chemotherapy-induced peripheral neuropathy in a randomized trial.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Palliative
Unknown

Approved Use

Unknown
Preventing
Unknown

Approved Use

Unknown
Palliative
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Long-term acetyl-L-carnitine treatment in Alzheimer's disease.
1991 Nov
Neuroprotective activity of acetyl-L-carnitine: studies in vitro.
1994 Jan
Acetyl-L-carnitine (levacecarnine) in the treatment of diabetic neuropathy. A long-term, randomised, double-blind, placebo-controlled study.
2002
L-acetylcarnitine: a proposed therapeutic agent for painful peripheral neuropathies.
2006 Jul
Treating Painful Diabetic Peripheral Neuropathy: An Update.
2016 Aug 1
Two-Year Trends of Taxane-Induced Neuropathy in Women Enrolled in a Randomized Trial of Acetyl-L-Carnitine (SWOG S0715).
2018 Jun 1
Patents

Patents

Sample Use Guides

orally at a dosage of 2000 mg/day
Route of Administration: Oral
In Vitro Use Guide
The neuroprotective properties of acetyl-L-carnitine (ALCAR) were investigated in primary cell cultures from rat hippocampal formation and cerebral cortex of 17-day-old rat embryos. ALCAR (10-50 microM for 10 days) reduced the cell mortality induced by 24 hr fetal calf serum deprivation. Protection was partial when the neuronal cells, chronically treated with ALCAR (50 microM), were exposed to glutamate (0.25-1 mM) and kainic acid (250-500 microM) for 24 hr. The neurotoxicity induced by N-methyl-D-aspartate (NMDA, 250 microM) was attenuated by the acute co-exposure with ALCAR (1 mM), the chronic treatment with ALCAR (50 microM) significantly reduced the neuronal death induced by NMDA (0.25-1 mM).
Substance Class Chemical
Created
by admin
on Sat Dec 16 00:39:35 GMT 2023
Edited
by admin
on Sat Dec 16 00:39:35 GMT 2023
Record UNII
2WQN168TM5
Record Status Validated (UNII)
Record Version
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Name Type Language
ACETYL CARNITINE HYDROCHLORIDE, DL-
Preferred Name English
ACETYLCARNITINE HYDROCHLORIDE, (±)-
Systematic Name English
1-PROPANAMINIUM, 2-(ACETYLOXY)-3-CARBOXY-N,N,N-TRIMETHYL-, CHLORIDE (1:1)
Systematic Name English
ACETYL DL-CARNITINE CHLORIDE
Common Name English
(±)-ACETYLCARNITINE CHLORIDE
Systematic Name English
ACETYLCARNITINE CHLORIDE, (±)-
Systematic Name English
ACETYLCARNITINE HYDROCHLORIDE, DL-
Common Name English
Code System Code Type Description
RXCUI
1593400
Created by admin on Sat Dec 16 00:39:35 GMT 2023 , Edited by admin on Sat Dec 16 00:39:35 GMT 2023
PRIMARY
PUBCHEM
197763
Created by admin on Sat Dec 16 00:39:35 GMT 2023 , Edited by admin on Sat Dec 16 00:39:35 GMT 2023
PRIMARY
CAS
2504-11-2
Created by admin on Sat Dec 16 00:39:35 GMT 2023 , Edited by admin on Sat Dec 16 00:39:35 GMT 2023
PRIMARY
EPA CompTox
DTXSID60947902
Created by admin on Sat Dec 16 00:39:35 GMT 2023 , Edited by admin on Sat Dec 16 00:39:35 GMT 2023
PRIMARY
FDA UNII
2WQN168TM5
Created by admin on Sat Dec 16 00:39:35 GMT 2023 , Edited by admin on Sat Dec 16 00:39:35 GMT 2023
PRIMARY
Related Record Type Details
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