6-Aminonicotinamid

Bezeichnung:6-Aminonicotinamid

CAS-Nr329-89-5

Englisch Name:6-Aminopyridine-3-carboxamide

CBNumberCB9224555

SummenformelC6H7N3O

Molgewicht137.14

MOL-Datei329-89-5.mol

Synonyma

6-Aminonicotinamid

6-Aminonicotinamid physikalisch-chemischer Eigenschaften

Schmelzpunkt	245-248 °C (lit.)
Siedepunkt	251.97°C (rough estimate)
Dichte	1.2620 (rough estimate)
Brechungsindex	1.6910 (estimate)
storage temp.	Keep in dark place,Inert atmosphere,Room temperature
Löslichkeit	insoluble in H2O; insoluble in EtOH; ≥13.7 mg/mL in DMSO
Aggregatzustand	powder to crystal
pka	15.66±0.50(Predicted)
Farbe	White to Light yellow
Wasserlöslichkeit	Soluble in Dimethyl sulfoxide (DMSO). Insoluble in water.
BRN	116042
CAS Datenbank	329-89-5(CAS DataBase Reference)
NIST chemische Informationen	Nicotinamide, 6-amino-(329-89-5)
EPA chemische Informationen	6-Aminonicotinamide (329-89-5)

Sicherheit

Kennzeichnung gefährlicher	T
R-Sätze:	61
S-Sätze:	53-45
RIDADR	1655
WGK Germany	3
RTECS-Nr.	US4550000
Hazard Note	Toxic
HazardClass	6.1
PackingGroup	II
HS Code	29333990

Gefahreninformationscode (GHS)

6-Aminopyridine-3-carboxamide Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R61:Kann das Kind im Mutterleib schädigen.
S-Sätze Betriebsanweisung:
S53:Exposition vermeiden - vor Gebrauch besondere Anweisungen einholen.
S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn möglich, dieses Etikett vorzeigen).
Verwenden
6-Aminonicotinamide induces apoptosis in tumor cells. It is clinically used in disseminated neoplastic disease. It also acts as 6-phosphogluconate dehydrogenase inhibitor. It aids in the treatment of psoriasis. It is used as cancer chemotherapeutic drug in animals.
Verwenden
antineoplastic, apoptosis inducer
Definition
ChEBI: A monocarboxylic acid amide resulting from the formal condensation of the carboxy group of 6-aminonicotinic acid with ammonia. An inhibitor of the NADP+-dependent enzyme, 6-phosphogluconate dehydrogenase, it interferes with glycolysis resulting in ATP depletion and synergizes with DNA-crosslinking chemotherapy drugs, such as cisplatin, in killing cancer cells.
Allgemeine Beschreibung
White crystalline solid.
Air & Water Reaktionen
Insoluble in water.
Reaktivität anzeigen
An amine and amide. Amines are chemical bases. They neutralize acids to form salts plus water. These acid-base reactions are exothermic. The amount of heat that is evolved per mole of amine in a neutralization is largely independent of the strength of the amine as a base. Amines may be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated by amines in combination with strong reducing agents, such as hydrides. Organic amides/imides react with azo and diazo compounds to generate toxic gases. Flammable gases are formed by the reaction of organic amides/imides with strong reducing agents. Amides are very weak bases (weaker than water). Imides are less basic yet and in fact react with strong bases to form salts. That is, they can react as acids. Mixing amides with dehydrating agents such as P2O5 or SOCl2 generates the corresponding nitrile. The combustion of these compounds generates mixed oxides of nitrogen (NOx).
Health Hazard
ACUTE/CHRONIC HAZARDS: When heated to decomposition 6-Aminopyridine-3-carboxamide emits toxic fumes of NOx.
Brandgefahr
Flash point data for 6-Aminopyridine-3-carboxamide are not available; however, 6-Aminopyridine-3-carboxamide is probably combustible.
Biologische Aktivität
ki: 0.46 μm6-aminonicotinamide is a 6-phosphogluconate dehydrogenase inhibitor.6-phosphogluconate dehydrogenase, an enzyme in the pentose phosphate pathway, can produce ribulose 5-phosphate from 6-phosphogluconate. 6-phosphogluconate dehydrogenase is also an oxidative carboxylase catalyzing the decarboxylating reduction of 6-phosphogluconate into ribulose 5-phosphate in the presence of nadp.
in vitro
6-aminonicotinamide could be metabolized to 6-amino-nad(p+), a competitive inhibitor of nad(p+)-requiring processes, especially the pentose phosphate pathway enzyme, 6-phosphogluconate dehydrogenase. moreove, 6-aminonicotinamide as a single agent could cause a significant inhibition of glycolytic flux but had no effect on the pentose phosphate pathway. 31p-nmr studies of perifused rif-1 cells indicated that 4 h of exposure to 6-aminonicotinamide was enough to cause significant accumulation of 6-phosphogluconate, the substrate for this enzyme [1].
in vivo
the influence of 6-aminonicotinamide on the g-6-p-dh- and 6-pg-dh-levels of the pentose phosphate pathway in the kidney was investigated. following i.p. administration of 6-aminonicotinamide at 6 mg/kg, the 6-pg-level rose from a value less than 10 nmoles/g to 1000 nmoles/g fresh weight within 24 h. in addition, at the end of the assay, after 7 days, a 6-pg-concentration of about 150 nmoles/g fresh weight was still seen. moreove, the g-6-p level simultaneously rose with the 6-pg-level to about 150% of the control level and returned to normal on the 5th day [2].
Einzelnachweise
[1] street, j. c.,alfieri, a.a. and koutcher, j.a. quantitation of metabolic and radiobiological effects of 6-aminonicotinamide in rif-1 tumor cells in vitro. cancer research 57, 3956-3962 (1997).
[2] lange, k. and proft, e.r. inhibition of the 6-phosphogluconate dehydrogenase in the rat kidney by 6-aminonicotinamide. naunyn-schmiedeberg's archives of pharmacology 267, 177-180 (1970).

6-Aminonicotinamid Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

329-89-5, 6-Aminopyridine-3-carboxamide Verwandte Suche:

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