D-Carnitine

HCID 2724480

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Grundinformationen

CAS
541-14-0
Standard-SMILES
C[N+](C)(C)C[C@@H](O)CC(=O)[O-]
InChIKey
PHIQHXFUZVPYII-LURJTMIESA-N
Summenformel
C7H15NO3
Durchschnittliche Molmasse
161,2 g/mol

Überblick

(S)-carnitine is the (S)-enantiomer of carnitine. It is a conjugate base of a (S)-carnitinium. It is an enantiomer of a (R)-carnitine.

Namen und Bezeichner

Bevorzugter Name
D-Carnitine
IUPAC
(3S)-3-hydroxy-4-(trimethylazaniumyl)butanoate

Namen und Synonyme

D-carnitine541-14-0D-(+)-carnitine(+)-Carnitine(S)-carnitine(3S)-3-hydroxy-4-(trimethylazaniumyl)butanoateCarnitine, (+)-UNII-U9VY0ZOK7AU9VY0ZOK7ACARNITINE, D-(3S)-3-hydroxy-4-(trimethylammonio)butanoate(+)-D-CARNITINE
Weitere Namen anzeigen
CHEBI:11060S-(+)-3-hydroxy-4-trimethylaminobutyrate1-Propanaminium, 3-carboxy-2-hydroxy-N,N,N-trimethyl-, hydroxide, inner salt, (S)-1-PROPANAMINIUM, 3-CARBOXY-2-HYDROXY-N,N,N-TRIMETHYL-, INNER SALT, (2S)-RefChem:130511L-I3-Trimethyl-I2-hydroxybutyrobetaine1-Propanaminium, 3-carboxy-2-hydroxy-N,N,N-trimethyl-, hydroxide, inner salt, (S)-(9CI)625-884-0

Datenbank-Bezeichner

CAS
541-14-0
PubChem CID
2724480
ChEMBL
CHEMBL503189
ChEBI
CHEBI:11060
UNII
U9VY0ZOK7A
EC Number
625-884-0
Nikkaji
J94.155G

Eigenschaften

Berechnete StruktureigenschaftenWird ergänzt

XLogP
-0,2
Polarare Oberfläche (TPSA)
60,4 Ų
H-Brücken-Donoren
1
H-Brücken-Akzeptoren
3
Frei drehbare Bindungen
3
Schwere Atome
11

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 39 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Hazard Classes and CategoriesSkin Irrit. 2 (100%)

Toxikologische Informationen

Exposure RoutesIntravenous, Oral. Absolute bioavailability is 15% (tablets or solution). Time to maximum plasma concentration was found to be 3.3 hours.
Toxicity Summary · 1 Eintrag

Levocarnitine can be synthesised within the body from the amino acids lysine or methionine. Vitamin C (ascorbic acid) is essential to the synthesis of carnitine. Levocarnitine is a carrier molecule in the transport of long chain fatty acids across the inner mitochondrial membrane. It also exports acyl groups from subcellular organelles and from cells to urine before they accumulate to toxic concentrations. Only the L isomer of carnitine (sometimes called vitamin BT) affects lipid metabolism. Levocarnitine is handled by several proteins in different pathways including carnitine transporters, carnitine translocases, carnitine acetyltransferases and carnitine palmitoyltransferases.

Signs and SymptomsAdverse effects include hypertension, fever, tachycardia and seizures.
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Toxicity DataLD<sub>50</sub> > 8g/kg (mouse, oral).

Chemie und Industrie

Pharmakologische Informationen

Metabolism/Metabolites · 1 Eintrag

After oral administration L-carnitine which is unabsorbed is metabolized in the gastrointestinal tract by bacterial microflora. Major metabolites include trimethylamine N-oxide and [3H]-gamma-butyrobetaine. Route of Elimination: Following a single intravenous dose, 73.1 +/- 16% of the dose was excreted in the urine during the 0-24 hour interval. Post administration of oral carnitine supplements, in addition to a high carnitine diet, 58-65% of the administered radioactive dose was recovered from urine and feces in 5-11 days. Half Life: 17.4 hours (elimination) following a single intravenous dose.

Verwendung und Herstellung

Uses · 1 Eintrag

For treatment of primary systemic carnitine deficiency, a genetic impairment of normal biosynthesis or utilization of levocarnitine from dietary sources, or for the treatment of secondary carnitine deficiency resulting from an inborn error of metabolism such as glutaric aciduria II, methyl malonic aciduria, propionic acidemia, and medium chain fatty acylCoA dehydrogenase deficiency. Used therapeutically to stimulate gastric and pancreatic secretions and in the treatment of hyperlipoproteinemias. Parenteral levocarnitine is indicated for the prevention and treatment of carnitine deficiency in patients with end-stage renal disease.

Anbieter100 Anbieter

阿诺西(上海)生物技术有限公司400-1107768 15058188853 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
Career Henan Chemica Co+86-0371-86658258 +86-13203830695 · [email protected]
武汉英诺医药科技有限公司+86-027-59232304 15387063101 · [email protected]
艾吉析科技(上海)有限公司17717235263 · [email protected]

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