ZALCITABINE
2',3'-dideoxycytidine
CAS: 7481-89-2
Molecular Formula: C9H13N3O3
ZALCITABINE - Names and Identifiers
| Name | 2',3'-dideoxycytidine |
| Synonyms | DDC D 2C ZALCITABINE zalcitabine dideoxycytidine 2',3'-DIDEOXYCYTIDINE 2',3'-dideoxycytidine 2',3'-dideoxy-cytidin 2',3'-Dideoxy-D-cytidine BETA-D-2',3'-DIDEOXYCYTIDINE Cytidine, 2',3'-dideoxy- (8CI, 9CI) 2'',3''-DIDEOXYCYTIDINE(ZALCITABINE) 1-(2',3'-DIDEOXY-BETA-RIBOFURANOSYL)CYTOSINE 4-AMINO-1-[(2R,5S)-5-(HYDROXYMETHYL)OXOLAN-2-YL]PYRIMIDIN-2-ONE 4-amino-1-[5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidin-2(1H)-one 4-amino-1-[(5S)-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidin-2(1H)-one |
| CAS | 7481-89-2 |
| EINECS | 620-762-3 |
| InChI | InChI=1/C9H13N3O3/c10-7-3-4-12(9(14)11-7)8-2-1-6(5-13)15-8/h3-4,6,8,13H,1-2,5H2,(H2,10,11,14)/t6-,8?/m0/s1 |
| InChIKey | WREGKURFCTUGRC-POYBYMJQSA-N |
ZALCITABINE - Physico-chemical Properties
| Molecular Formula | C9H13N3O3 |
| Molar Mass | 211.22 |
| Density | 1.2605 (rough estimate) |
| Melting Point | 217-218°C(lit.) |
| Boling Point | 350.9°C (rough estimate) |
| Specific Rotation(α) | D25 +81° (c = 0.635 in water) |
| Flash Point | 204.776°C |
| Water Solubility | 5-10 g/100 mL at 19 ºC |
| Solubility | DMSO (Slightly, Heated), Methanol (Slightly), Water (Slightly, Sonicated) |
| Vapor Presure | 0mmHg at 25°C |
| Appearance | powder |
| Color | colorless |
| Merck | 14,10109 |
| BRN | 654956 |
| pKa | 14.44±0.10(Predicted) |
| Storage Condition | Keep in dark place,Inert atmosphere,Store in freezer, under -20°C |
| Stability | Stable. Combustible. Incompatible with strong oxidizing agents. |
| Refractive Index | 78 ° (C=0.5, H2O) |
| MDL | MFCD00012188 |
| Physical and Chemical Properties | Crystallization from ethanol and benzene, melting point 215-217 °c melting point 209-210 °c has also been reported. [Α] D23 8l °(C = 0.635, water). UV maximum absorption (0.1mol/L hydrochloric acid):280nm (× 17720);(0.1mol/L sodium hydroxide):270nm (× 8410). |
ZALCITABINE - Risk and Safety
| Risk Codes | R40 - Limited evidence of a carcinogenic effect R36/37 - Irritating to eyes and respiratory system. R34 - Causes burns |
| Safety Description | S22 - Do not breathe dust. S36 - Wear suitable protective clothing. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. S27 - Take off immediately all contaminated clothing. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. |
| WGK Germany | 3 |
| RTECS | HA3870000 |
| FLUKA BRAND F CODES | 10-23 |
| HS Code | 2934990002 |
ZALCITABINE - Reference
| Reference Show more | 1. [IF=4.411] Yujiao Hua et al."Quality Evaluation of Pseudostellariae Radix Based on Simultaneous Determination of Multiple Bioactive Components Combined with Grey Relational Analysis."Molecules. 2017 Jan;22(1):13 2. [IF=1.618] Wang Shengnan et al."Simultaneous Determination of Iridoid Glycosides, Phenylpropanoid Glycosides, Organic Acids, Nucleosides and Amino Acids in Scrophulariae Radix Processed by Different Processing Methods by HPLC-QTRAP-MS/MS."J Chromatogr Sci. 2021 Jun; |
ZALCITABINE - Reference Information
| (IARC) carcinogen classification | 2B (Vol. 76) 2000 |
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| biological activity | zallitabine (NSC 606170, Ro 24-2027/000) is a nucleoside HIV reverse transcriptase inhibitor (NARTI). |
| Target | Value |
| Use | acts at the early stage of HIV replication, inhibiting Virus of reverse transcriptase and terminating Virus of DNA strand replication. For the treatment of patients with advanced immunodeficiency virus infection. antiviral drugs, used for anti-cancer, anti-HIV |
| production method | N-acetyl cytosine nucleoside (4G, 14 mmol) was refluxed in mL of acetonitrile, acetyl bromide (10ml,0.137 mol) was added dropwise over 30min and refluxed for 3h after addition. The solvent was distilled off, and the residue was dissolved in 100ml of chloroform and washed with 100ml of water. The chloroform was distilled off, and the residue was recrystallized from 10ml of ethanol to obtain 2g of compound (I) in a yield of 33% with a melting point of 79 ° -180 ° C. (decomposition) as colorless Flake crystals. Compound (I)(1G, 2.3 mmol), 1g of calcium carbonate, 50% G of palladium-barium sulfate and 50ml of methanol were shaken with hydrogen gas for 1H at 25 ° C. And normal pressure (60ml of hydrogen was absorbed). The crystals were removed by filtration and the filtrate was concentrated to dryness. The residue was dissolved in 10ml of a 20% ammonia-methanol solution and allowed to stand at 5 °c overnight. After column chromatography, it was recrystallized from ethanol to obtain 34mg of colourless crystalline gemcitabine in a yield of 7%. |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-10 22:29:15
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View History
ZALCITABINE
十二羰基三铁 (Assay on dry basis), 5-10% 甲醇做稳定剂
D-Alanine, alanyl- (9CI)
4(3H)-Quinazolinimine, 3-[(2-chlorophenyl)methyl]-2-[[(2,4-dichlorophenyl)methyl]thio]-6,7-dimethoxy-
全氟己基乙基二甲基丁醚
三(3-三甲氧基硅丙基)异氰脲酸酯
2-(4-甲氧苯基)-氯乙烷
4-硝基三氟乙酸苯酯
2-Heptanone, 6-methyl-7-[(tetrahydro-2H-pyran-2-yl)oxy]-, (6S)-
十二羰基三铁 (Assay on dry basis), 5-10% 甲醇做稳定剂
D-Alanine, alanyl- (9CI)
4(3H)-Quinazolinimine, 3-[(2-chlorophenyl)methyl]-2-[[(2,4-dichlorophenyl)methyl]thio]-6,7-dimethoxy-
全氟己基乙基二甲基丁醚
三(3-三甲氧基硅丙基)异氰脲酸酯
2-(4-甲氧苯基)-氯乙烷
4-硝基三氟乙酸苯酯
2-Heptanone, 6-methyl-7-[(tetrahydro-2H-pyran-2-yl)oxy]-, (6S)-