5-AMino-1H-[1,2,3]triazolo[4,5-d]pyriMidin-7(6H)-one
8-Azaguanine
CAS: 134-58-7
Molecular Formula: C4H4N6O
5-AMino-1H-[1,2,3]triazolo[4,5-d]pyriMidin-7(6H)-one - Names and Identifiers
5-AMino-1H-[1,2,3]triazolo[4,5-d]pyriMidin-7(6H)-one - Physico-chemical Properties
| Molecular Formula | C4H4N6O |
| Molar Mass | 152.11 |
| Density | 1.5579 (rough estimate) |
| Melting Point | >300°C(lit.) |
| Boling Point | 274.55°C (rough estimate) |
| Flash Point | 132.7°C |
| Water Solubility | 1.47E+004 mg/L |
| Vapor Presure | 0.00149mmHg at 25°C |
| Appearance | White powder |
| Merck | 896 |
| pKa | 6.75±0.20(Predicted) |
| Storage Condition | Keep in dark place,Inert atmosphere,Store in freezer, under -20°C |
| Refractive Index | 2.3000 (estimate) |
| MDL | MFCD00056937 |
| Physical and Chemical Properties | Needle-like crystalline powder; About 300 ℃ decomposition; Difficult to dissolve in water, soluble in dilute alkali and dilute acid. |
| In vitro study | 8-Azaguanine is a purine analog that shows antitumor activity. It acts as an antimetabolite, easily integrates into ribonucleic acid, interferes with normal biosynthetic pathways, and thereby inhibits cell growth. |
| In vivo study | In vivo metabolic studies of 8-azaguanine-2-C 14 were performed in tumors of mice susceptible or resistant to growth inhibition by 8 azagnanine. The results showed that the growth of these tumors transformed from 8-azaguanine to 8-azaguanylic acid was largely inhibited by 8-azaguanine. |
5-AMino-1H-[1,2,3]triazolo[4,5-d]pyriMidin-7(6H)-one - Risk and Safety
| Hazard Symbols | Xn - Harmful |
| Risk Codes | 22 - Harmful if swallowed |
| Safety Description | S22 - Do not breathe dust. S24/25 - Avoid contact with skin and eyes. |
| WGK Germany | 3 |
| RTECS | XZ6157000 |
| FLUKA BRAND F CODES | 10-23 |
| HS Code | 29335990 |
| Toxicity | LD50 oral in mouse: 1500mg/kg |
5-AMino-1H-[1,2,3]triazolo[4,5-d]pyriMidin-7(6H)-one - Nature
Open Data Verified Data
This product is needle-like crystalline powder with a molecular weight of 152.12. Decomposition at about 300 °c. Difficult to dissolve in water, soluble in dilute alkali and dilute acid. This product is purine antimetabolites, can inhibit microbial, Virus, the proliferation of tumor cells. May be through the inhibition of ribonucleoside reductase, thereby blocking
A ribonucleotide is converted to a deoxyribonucleotide; Its toxic effect may also be manifested by incorporation into RNA.
Last Update：2024-01-02 23:10:35
5-AMino-1H-[1,2,3]triazolo[4,5-d]pyriMidin-7(6H)-one - Use
Open Data Verified Data
- anticancer drug. For leukemia, uterine cancer, breast cancer, bone cancer, lung cancer, rectal cancer, sarcoma, etc.
- usage and dose of intramuscular injection, Daily 40~160mg, total 2000mg. Intravenous injection, Daily 20 ~ lOOmg, the total amount of 2000 ~ 3500mg.
Last Update：2022-01-01 11:12:26
5-AMino-1H-[1,2,3]triazolo[4,5-d]pyriMidin-7(6H)-one - Safety
Open Data Verified Data
Nausea, Vomit, loss of appetite, Diarrhea, Head Pain, thirst, skin erythema, flushing, leukopenia, malaise, rash, bleeding spots. Myelosuppression was mild, with renal impairment, arrhythmia, and myocardial infarction.
Last Update：2022-01-01 11:12:27
5-AMino-1H-[1,2,3]triazolo[4,5-d]pyriMidin-7(6H)-one - Reference Information
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| Biological activity | Azaguanine-8 (NSC-749, SF-337, SK 1150) are purine analogs with anti-tumor activity and compete with guanine in metabolism. |
| use | anticancer drugs. It is a purine antimetabolite that can inhibit the proliferation of microorganisms, viruses, and tumor cells. Adverse reactions include nausea, vomiting, loss of appetite, diarrhea, headache, thirst, skin erythema, facial redness, leukopenia, general fatigue, rash, and bleeding spots. Minor bone marrow suppression, kidney injury, arrhythmia and myocardial infarction. pharmaceutical intermediate, used to produce anti-tumor drug cancer enemy-M. |
| Production method | It is obtained by nitrosation, reduction, diazotization and cyclization of 2, 4-diamino-6-hydroxypyrimidine. (1) 2, 4-diamino-5-nitroso-6-hydroxypyrimidine is obtained by nitrosation: below 15 ℃, sodium nitrite is added to an aqueous solution of 2, 4-diamino-6-hydroxypyrimidine, and concentrated hydrochloric acid is added dropwise to precipitate rose red precipitate with a pH of about 3.5. Filter and wash with water until neutral to obtain 2, 4-diamino-5-nitroso-6-hydroxypyrimidine (nitroso). (2) Reduction to obtain 2,4, 5-triamino-6-hydroxypyrimidine sulfate (triamino): the nitroso substance is mixed and suspended in water, and the hydrosulfite is gradually added under stirring. Then add sodium hydroxide solution to make pH = 9, heat to boiling, and change the reaction solution from red to light yellow. Add activated carbon to decolorize and filter. After the filtrate is cooled, it is adjusted to Congo red with sulfuric acid to be acidic, and yellow precipitate is precipitated. Filter and wash with ethanol to get triamino. (3) 8-azoguanine is obtained by diazotization and cyclization: the triamino group is suspended in water, sodium hydroxide solution is added, and heated to dissolve. Then add sodium nitrite, stir and dissolve after adding glacial acetic acid. Heat to 90 ℃ for 1h. Cooling, filtering, 8-azoguanine crude, refined to obtain the finished product. |
| category | toxic substances |
| toxicity classification | poisoning |
| acute toxicity | abdominal cavity-rat LD50: 1000 mg/kg; Oral administration-mouse LD50: 1500 mg/kg |
| flammability hazard characteristics | combustible; combustion produces toxic nitrogen oxide smoke |
| storage and transportation characteristics | warehouse ventilation and low temperature drying |
| fire extinguishing agent | dry powder, foam, sand, carbon dioxide, mist water |
Last Update：2024-04-09 02:00:06
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Multiple SpecificationsSpot supply
Product Name: 8-Azaguanine Visit Supplier Webpage Request for quotationCAS: 134-58-7
Tel: 18301782025
Email: 3008007409@qq.com
Mobile: 18021002903
QQ: 3008007409
Wechat: 18301782025
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