Name | 5-Azacytidine |
Synonyms | 5-AC 5 AZC 5-AZAC 5-AZCR u18496 u 18496 mylosar wr 183027 nci-c01569 nsc-102816 Azacitidine ladakamycin Mylosar-15N4 5-Azacytidine NSC 102816-15N4 Azacitidine-15N4 LadakaMycin-15N4 LedakaMycin-15N4 Azacytidine-15N4 antibioticu18496 NSC 103-627-15N4 Antibiotic u 18496 Antibiotic U 18496-15N4 4-amino-1-pentofuranosyl-1,3,5-triazin-2(1H)-one 4-amino-1-beta-d-ribofuranosyl-s-triazin-2(1h)-on 4-amino-1-D-lyxofuranosyl-1,3,5-triazin-2(1H)-one 4-amino-1-beta-D-ribofuranosyl-s-triazin-2(1H)-one 5-triazin-2(1h)-one,4-amino-1-beta-d-ribofuranosyl-3 4-amino-1-beta-D-ribofuranosyl-1,3,5-triazin-2(1H)-one 4-Amino-1-(beta-D-ribofuranosyl)-1,3,5-triazin-2(1H)-one |
CAS | 320-67-2 |
EINECS | 206-280-2 |
InChI | InChI=1/C8H12N4O5/c9-7-10-2-12(8(16)11-7)6-5(15)4(14)3(1-13)17-6/h2-6,13-15H,1H2,(H2,9,11,16)/t3-,4+,5+,6?/m1/s1 |
InChIKey | NMUSYJAQQFHJEW-WGDKFINWSA-N |
Molecular Formula | C8H12N4O5 |
Molar Mass | 244.2 |
Density | 1.4287 (rough estimate) |
Melting Point | 226-232°C (dec.)(lit.) |
Boling Point | 387.12°C (rough estimate) |
Specific Rotation(α) | 40 º (C=1, H2O 22 ºC) |
Flash Point | 277°C |
Water Solubility | 0.5-1.0 g/100 mL at 21 ºC |
Solubility | Soluble in 10mg/ml 1M hydrochloric acid water. |
Vapor Presure | 1.18E-13mmHg at 25°C |
Appearance | White to white-like powder |
Color | White to Off-white |
Merck | 14,887 |
BRN | 620461 |
pKa | 13.46±0.70(Predicted) |
Storage Condition | -20°C |
Stability | Stable for 2 years from date of purchase as supplied. Solutions in DMSO or distilled water may be stored at -20° for up to 1 month. |
Sensitive | Easily absorbing moisture |
Refractive Index | 1.6590 (estimate) |
MDL | MFCD00006539 |
Physical and Chemical Properties | This product is a pyrimidine nucleoside analog produced by microbial strep toverticilium ladakanus, and can also be synthesized by chemical methods. It is a cell cycle-specific drug acting on S phase, which can rapidly phosphorylate and incorporate RNA and DNA to inhibit protein synthesis by disrupting the smooth translation of nucleic acid into protein. Pyrimidine synthesis can also be affected by inhibition of orotate nucleotide decarboxylase. |
Use | Antimetabolites. The primary indication is acute myeloid leukemia that does not respond to conventional therapy. Also used for breast cancer, melanoma, colon cancer, etc. The main toxicities were leukopenia, thrombocytopenia and anemia. Nausea and Vomit are common adverse reactions, which can be improved by long-term continuous infusion, or with antiemetics 24h to 48h before treatment. Other toxic effects were Diarrhea, neuromuscular disturbances, Fever, hypotension and rash. The formulations were freshly formulated 3-4H before use. |
Hazard Symbols | T - Toxic |
Risk Codes | R45 - May cause cancer R46 - May cause heritable genetic damage R22 - Harmful if swallowed |
Safety Description | S53 - Avoid exposure - obtain special instructions before use. S22 - Do not breathe dust. S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) |
WGK Germany | 3 |
RTECS | XZ3017500 |
FLUKA BRAND F CODES | 10-23 |
HS Code | 29349990 |
Toxicity | LD50 in mice (mg/kg): 115.9 i.p.; 572.3 orally (Palm, Kensler) |
This product is a pyrimidine nucleoside analog produced by microorganism Streptoverticil-lium ladakan,us, and can also be synthesized by chemical methods. It is rapidly phosphorylated and binds to RNA and DNA by disrupting the smooth translation of nucleic acids into proteins, while inhibiting protein synthesis. In addition, it affects the synthesis of pyrimidine by inhibiting orotate nucleotide decarboxylase. It is a cell cycle-specific drug that acts on the S phase. Molecular weight 244. 21.
dose-limiting toxicity is mainly hematologic and is often manifested by leukopenia, thrombocytopenia, and anemia. Nausea and Vomit are common and can be severe and long. The symptoms may be improved by prolonged continuous infusion. Antiemetics may be helpful 24-48h before treatment. Other toxic effects were Diarrhea, neuromuscular disturbances, Fever, hepatotoxicity, hypotension and rash. The preparation was freshly prepared 3-4H before use.