329-89-5

Basic information

• Product Name: 6-Aminopyridine-3-carboxamide
• Synonyms: 2-AMINOPYRIDINE-5-CARBOXAMIDE;6-AMINOPYRIDINE-3-CARBOXAMIDE;6-AMINONICOTINAMIDE;6-AMINO-3-PYRIDINECARBOXAMIDE;2-Amino-5-carbamoylpyridine;3-Pyridinecarboxamide, 6-amino-;6-amino-3-pyridinecarboxamid;6-amino-nicotinamid
• CAS NO: 329-89-5
• Molecular Formula: C₆H₇N₃O
• Molecular Weight: 137.14
• EINECS: 206-349-7
• Product Categories: AMIDE;Pyridine series;Amines;Pyridines;Heterocyclic Compounds;Building Blocks;C6;Chemical Synthesis;Heterocyclic Building Blocks
• Mol File: 329-89-5.mol

Chemical Properties

• Melting Point: 245-248 °C(lit.)
• Boiling Point: 251.97°C (rough estimate)
• Flash Point: 184.6 °C
• Appearance: White crystalline solid
• Density: 1.2620 (rough estimate)
• Vapor Pressure: 5E-06mmHg at 25°C
• Refractive Index: 1.6910 (estimate)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: insoluble in H2O; insoluble in EtOH; ≥13.7 mg/mL in DMSO
• PKA: 15.66±0.50(Predicted)
• Water Solubility: Soluble in Dimethyl sulfoxide (DMSO). Insoluble in water.
• BRN: 116042
• CAS DataBase Reference: 6-Aminopyridine-3-carboxamide(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Aminopyridine-3-carboxamide(329-89-5)
• EPA Substance Registry System: 6-Aminopyridine-3-carboxamide(329-89-5)

Safety Data

• Hazard Codes: T
• Statements: 61
• Safety Statements: 53-45
• RIDADR: 1655
• WGK Germany: 3
• RTECS: US4550000
• HazardClass: 6.1
• PackingGroup: II
• Hazardous Substances Data: 329-89-5(Hazardous Substances Data)

Usage

Uses

Used in Antineoplastic Applications:
6-Aminopyridine-3-carboxamide is used as an antineoplastic agent, specifically as an apoptosis inducer in tumor cells. It is clinically utilized in the treatment of disseminated neoplastic diseases, helping to combat the growth and spread of cancer cells.
Used in Psoriasis Treatment:
6-Aminopyridine-3-carboxamide is also used in the treatment of psoriasis, a chronic skin condition characterized by the rapid buildup of skin cells, leading to red, scaly patches.
Used in Cancer Chemotherapy for Animals:
In addition to its use in human medicine, 6-Aminopyridine-3-carboxamide is employed as a cancer chemotherapeutic drug in veterinary medicine, providing a therapeutic option for animals suffering from neoplastic diseases.
Used in Pharmaceutical Industry:
6-Aminopyridine-3-carboxamide is used as an inhibitor in the pharmaceutical industry, specifically targeting the NADP+-dependent enzyme, 6-phosphogluconate dehydrogenase. Its ability to interfere with glycolysis and deplete ATP makes it a valuable compound in the development of drugs aimed at treating various diseases, including cancer.

Air & Water Reactions

Insoluble in water.

Health Hazard

ACUTE/CHRONIC HAZARDS: When heated to decomposition 6-Aminopyridine-3-carboxamide emits toxic fumes of NOx.

Fire Hazard

Flash point data for 6-Aminopyridine-3-carboxamide are not available; however, 6-Aminopyridine-3-carboxamide is probably combustible.

Biological Activity

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].

references

[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).

InChI:InChI=1/C6H7N3O/c7-5-2-1-4(3-9-5)6(8)10/h1-3H,(H2,7,9)(H2,8,10)

Upstream product

• 4214-73-7 6-aminonicotinonitrile 
• 6271-78-9 6-chloro-3-pyridinecarboxamide 
• 39658-41-8 ethyl-6-amino-nicotinate 
• 77837-05-9 6-acetylamino-nicotinic acid amide 
• 1603-41-4 (5-methyl-pyridin-2-yl)amine 
• 4931-47-9 N-(5-methylpyridin-2-yl)acetamide 
• 36052-24-1 methyl 6-aminonicotinoate 
• 98953-23-2 6-acetamide-nicotinic acid methyl ester 
• 21550-48-1 6-(acetylamino)pyridine-3-carboxylic acid 
• 3167-49-5 6-aminonicotinic acid 
• 3670-59-5 6-hydroxynicotinamide 

Downstream Products

• 3167-49-5 6-aminonicotinic acid 
• 39658-41-8 ethyl-6-amino-nicotinate 
• 156973-09-0 2-amino-5-aminomethyl-pyridine 
• 38922-97-3 2-phenylimidazo[1,2-a]pyridine-6-carboxamide 
• 652-81-3 diphosphoric acid-1-[(1R)-1-(2-amino-5-carbamoyl-pyridinio)-D-1,4-anhydro-ribitol-5-yl ester]-2-(O^2'-phosphono-adenosin-5'-yl ester)-betaine 
• 77837-05-9 6-acetylamino-nicotinic acid amide 
• 183853-45-4 ((R)-1-{(S)-2-[(6-Amino-pyridin-3-ylmethyl)-carbamoyl]-pyrrolidine-1-carbonyl}-2,2-dicyclohexyl-ethyl)-carbamic acid tert-butyl ester 
• 183853-48-7 ((R)-1-{(S)-2-[(6-Amino-pyridin-3-ylmethyl)-carbamoyl]-pyrrolidine-1-carbonyl}-2,2-diphenyl-ethyl)-carbamic acid tert-butyl ester 
• 87745-86-6 N-Benzyl-2-methyl-3-ethyl-4-oxo-4H-pyrido<1,2-a>pyrimidine-7-carboxamide 
• 113293-71-3 (6-amino-3-pyridinyl)methanol 
• 132213-03-7 imidazo<1,2-a>pyridin-6-ylmethylamine 
• 132213-07-1 6-(hydroxymethyl)imidazo[1,2-a]pyridine 
• 501921-60-4 C₂₃H₁₇ClN₄O₃ 
• 733-02-8 2-(4-fluoro-phenyl)-imidazo[1,2-a]pyridine-6-carboxylic acid amide 

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