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Details

Stereochemistry RACEMIC
Molecular Formula C9H17NO4
Molecular Weight 203.2356
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

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

SMILES

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

InChI

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

HIDE SMILES / InChI

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 Fri Dec 15 16:51:17 GMT 2023
Edited
by admin
on Fri Dec 15 16:51:17 GMT 2023
Record UNII
07OP6H4V4A
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ACETYLCARNITINE, (±)-
Systematic Name English
1-PROPANAMINIUM, 2-(ACETYLOXY)-3-CARBOXY-N,N,N-TRIMETHYL-, INNER SALT
Systematic Name English
DL-ACETYLCARNITINE
Common Name English
2-(ACETYLOXY)-3-CARBOXY-N,N,N-TRIMETHYL-1-PROPANAMINIUM INNER SALT
Common Name English
O-ACETYL-DL-CARNITINE
Common Name English
ACETYLCARNITINE RACEMATE [MI]
Common Name English
(3-CARBOXY-2-HYDROXYPROPYL)TRIMETHYLAMMONIUM HYDROXIDE INNER SALT ACETATE
Common Name English
ACETYL-DL-CARNITINE
Common Name English
AMMONIUM, (3-CARBOXY-2-HYDROXYPROPYL)TRIMETHYL-, HYDROXIDE, INNER SALT, ACETATE
Common Name English
ACETYLCARNITINE, DL-
Common Name English
ACETYLCARNITINE DL-FORM
MI  
Common Name English
Code System Code Type Description
MERCK INDEX
m1349
Created by admin on Fri Dec 15 16:51:17 GMT 2023 , Edited by admin on Fri Dec 15 16:51:17 GMT 2023
PRIMARY
PUBCHEM
1
Created by admin on Fri Dec 15 16:51:17 GMT 2023 , Edited by admin on Fri Dec 15 16:51:17 GMT 2023
PRIMARY
RXCUI
1310540
Created by admin on Fri Dec 15 16:51:17 GMT 2023 , Edited by admin on Fri Dec 15 16:51:17 GMT 2023
PRIMARY RxNorm
EPA CompTox
DTXSID2048117
Created by admin on Fri Dec 15 16:51:17 GMT 2023 , Edited by admin on Fri Dec 15 16:51:17 GMT 2023
PRIMARY
CAS
14992-62-2
Created by admin on Fri Dec 15 16:51:17 GMT 2023 , Edited by admin on Fri Dec 15 16:51:17 GMT 2023
PRIMARY
FDA UNII
07OP6H4V4A
Created by admin on Fri Dec 15 16:51:17 GMT 2023 , Edited by admin on Fri Dec 15 16:51:17 GMT 2023
PRIMARY
CHEBI
73024
Created by admin on Fri Dec 15 16:51:17 GMT 2023 , Edited by admin on Fri Dec 15 16:51:17 GMT 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY