Grundinformationen
- Standard-SMILES
O=C([O-])c1cccnc1- InChIKey
PVNIIMVLHYAWGP-UHFFFAOYSA-M- Summenformel
- C6H4NO2-
- Durchschnittliche Molmasse
- 122,1 g/mol
- Monoisotopische Masse
- 122,02420337
Namen und Bezeichner
- Bevorzugter Name
- Nicotinate
- IUPAC
- pyridine-3-carboxylate
Namen und Synonyme
Datenbank-Bezeichner
- PubChem CID
- 937
- ChEBI
CHEBI:32544- Nikkaji
- J239.335B
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 0,9
- Polarare Oberfläche (TPSA)
- 53 Ų
- H-Brücken-Donoren
- 0
- H-Brücken-Akzeptoren
- 3
- Frei drehbare Bindungen
- 0
- Schwere Atome
- 9
- Formalladung
- -1
- Komplexität
- 108
Experimentelle und physikochemische Eigenschaften
Collision Cross Section
121 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)];124 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]
124 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]
Sicherheit und Regulatorisches
Toxikologische Informationen
Health Effects
Niacin at extremely high doses can have life-threatening acute toxic reactions. Extremely high doses of niacin can also cause niacin maculopathy, a thickening of the macula and retina which leads to blurred vision and blindness. This maculopathy is reversible after stopping niacin intake. Side effects of hyperglycemia, cardiac arrhythmias and birth defects have also been reported. (A729)
Toxicity Summary
Niacin binds to Nicotinate D-ribonucleotide phyrophsopate phosphoribosyltransferase, Nicotinic acid phosphoribosyltransferase, Nicotinate N-methyltransferase and the Niacin receptor. Niacin is the precursor to nicotinamide adenine dinucleotide (NAD) and nicotinamide adenine dinucleotide phosphate (NADP), which are vital cofactors for dozens of enzymes. The mechanism by which niacin exerts its lipid lowering effects is not entirely understood, but may involve several actions, including a decrease in esterification of hepatic triglycerides. Niacin treatment also decreases the serum levels of apolipoprotein B-100 (apo B), the major protein component of the VLDL (very low-density lipoprotein) and LDL fractions.
Signs and Symptoms
Nicotinic acid can cause vasodilation of cutaneous blood vessels resulting in increased blood flow, principally in the face, neck and chest. This produces the niacin- or nicotinic acid-flush. The niacin-flush is thought to be mediated via the prostaglandin prostacyclin. Histamine may also play a role in the niacin-flush. Flushing is the adverse reaction first observed after intake of a large dose of nicotinic acid, and the most bothersome one.
Chemie und Industrie
Pharmakologische Informationen
Metabolism/Metabolites
Niacin is rapidly metabolized and undergoes extensive first-pass metabolism in the liver. The drug is converted to several metabolites, including nicotinuric acid (NUA), nicotinamide, and nicotinamide adenine dinucleotide (NAD). At doses used to treat hyperlipoproteinemia, the principal metabolic pathways appear to be saturable, and niacin is thought to exhibit nonlinear, dose-dependent pharmacokinetics. (L1323) Half Life: 20-45 minutes.
MeSH Pharmacological Classification
Substances that lower the levels of certain LIPIDS in the BLOOD. They are used to treat HYPERLIPIDEMIAS.
Drugs used to cause dilation of the blood vessels.
A group of water-soluble vitamins, some of which are COENZYMES.
Verwendung und Herstellung
Uses
For the treatment of type IV and V hyperlipidemia. It is indicated as ajunctive therapy. It can be found in various foods, such as liver, chicken, beef, fish, cereal, peanuts and legumes. Niacin is also used as a pharmaceutical to reverse atherosclerosis. (A729)
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