Tenofovir disoproxil fumarate CAS#: 202138-50-9; 凯望编码 (ChemWhat Code): 122766
Identification
| 英文名 | Tenofovir disoproxil fumarate |
| IUPAC Name | [[(2R)-1-(6-aminopurin-9-yl)propan-2-yl]oxymethyl-(propan-2-yloxycarbonyloxymethoxy)phosphoryl]oxymethyl propan-2-yl carbonate;(E)-but-2-enedioic acid |
| 分子结构 |  |
| CAS编号 | 202138-50-9 |
| EINECS Number | No data available |
| MDL Number | MFCD08141829 |
| Beilstein Registry Number | No data available |
| 别名 | tenofovir disoproxyl fumarateTenofovir Disoproxil Fumarate(R)-(((1-(6-amino-9H-purin-9-yl)propan-2-yloxy)methyl)phosphoryl)bis(oxy)bis(methylene)isopropyl dicarbonate fumarate2-(adenin-9-yl)-1-(R)-methyl-ethoxymethylphosphonic acid bis(isopropoxycarbonyloxymethyl)ester fumarate9-[(R)-2-[[bis[[(isopropoxycarbonyl) oxy]methoxy]phosphinyl]methoxy]propyl] adenine fumarate salt9-[2-(R)-[[bis[[(isopropoxycarbonyl)oxy]methoxy]phosphinoyl]methoxy]propyl]adenine fumarate9-[(R)-2-[[bis[[(isopropoxycarbonyl)oxy]methoxy]phosphinyl]methoxy]propyl]adenine fumarate |
| 分子式 | C23H34N5O14P |
| 分子量 | 635.515 |
| InChI | InChI=1S/C19H30N5O10P.C4H4O4/c1-12(2)33-18(25)28-9-31-35(27,32-10-29-19(26)34-13(3)4)11-30-14(5)6-24-8-23-15-16(20)21-7-22-17(15)24;5-3(6)1-2-4(7)8/h7-8,12-14H,6,9-11H2,1-5H3,(H2,20,21,22);1-2H,(H,5,6)(H,7,8)/b;2-1+/t14-;/m1./s1 |
| InChI Key | VCMJCVGFSROFHV-WZGZYPNHSA-N |
| Canonical SMILES | C[C@H](Cn1cnc2c1ncnc2N)OCP(=O)(OCOC(=O)OC(C)C)OCOC(=O)OC(C)C.C(=C/C(=O)O)\C(=O)O |
| Patent Information | ||
| Patent ID | Title | Publication Date |
| US2019/216831 | ANTIVIRAL COMPOSITION | 2019 |
| US2009/12292 | NOVEL PROCESS FOR ACYCLIC PHOSPHONATE NUCLEOTIDE ANALOGS | 2009 |
| WO2007/13085 | NOVEL PROCESS FOR ACYCLIC PHOSPHONATE NUCLEOTIDE ANALOGS | 2007 |
Physical Data
| Appearance | White powder |
| Solubility | No data available |
| Flash Point | No data available |
| Refractive index | No data available |
| Sensitivity | No data available |
| Melting Point, °C | Solvent (Melting Point) |
| 118.11 |
| Measurement Temperature, °C | Type (Density) |
| 25 | crystallographic |
Spectra
| Description (NMR Spectroscopy) | Nucleus (NMR Spectroscopy) | Solvents (NMR Spectroscopy) | Frequency (NMR Spectroscopy), MHz |
| Chemical shifts, Spectrum | 1H | dimethylsulfoxide-d6 | 300 |
| Chemical shifts, Spectrum | 1H | chloroform-d1 | |
| COSY (Correlation Spectroscopy) | 1H, 1H | ||
| CPMAS (Cross Polarization Magic-Angle Spinning), Chemical shifts, Spectrum | 13C | 100.6 |
| Description (IR Spectroscopy) | Solvent (IR Spectroscopy) |
| ATR (attenuated total reflectance), Bands | |
| Bands, Spectrum | |
| ATR-FTIR (attenuated total reflectance Fourier transform infrared spectroscopy), Bands, Spectrum | potassium bromide |
| Description (Mass Spectrometry) |
| tandem mass spectrometry, liquid chromatography mass spectrometry (LCMS), IT (ion trap), electrospray ionisation (ESI), CID (collision-induced dissociation), fragmentation pattern, spectrum |
| spectrum |
| liquid chromatography mass spectrometry (LCMS), high resolution mass spectrometry (HRMS), electrospray ionisation (ESI), time-of-flight mass spectra (TOFMS), fragmentation pattern, spectrum |
| Description (UV/VIS Spectroscopy) | Solvent (UV/VIS Spectroscopy) | Absorption Maxima (UV/VIS), nm |
| Spectrum | water | 281 |
| Spectrum | 260 |
Route of Synthesis (ROS)
| Conditions | Yield |
| Stage #1: tenofovir With triethylamine In 1-methyl-pyrrolidin-2-one at 63℃; for 0.5h; Stage #2: chloromethyl isopropyl carbonate In 1-methyl-pyrrolidin-2-one at 63℃; for 4h; Stage #3: (2E)-but-2-enedioic acid In isopropyl alcohol at 50℃; for 0.5h; Concentration; | 90% |
| Stage #1: chloromethyl isopropyl carbonate; tenofovir With tetrabutylammomium bromide; triethylamine at 50℃; for 3h; Inert atmosphere; Stage #2: (2E)-but-2-enedioic acid In isopropyl alcohol Reagent/catalyst; Temperature; Reflux; | 78.8% |
| Stage #1: chloromethyl isopropyl carbonate; tenofovir With tetrabutylammomium bromide; triethylamine In 1-methyl-pyrrolidin-2-one; toluene at 45 – 55℃; for 5h; Stage #2: (2E)-but-2-enedioic acid In isopropyl alcohol at 50 – 55℃; for 2h; | 63.6% |
Safety and Hazards
| Pictogram(s) |    |
| Signal | Danger |
| GHS Hazard Statements | H302 (88.37%): Harmful if swallowed [Warning Acute toxicity, oral] H318 (16.28%): Causes serious eye damage [Danger Serious eye damage/eye irritation] H319 (83.72%): Causes serious eye irritation [Warning Serious eye damage/eye irritation] H373 (81.4%): Causes damage to organs through prolonged or repeated exposure [Warning Specific target organ toxicity, repeated exposure] Information may vary between notifications depending on impurities, additives, and other factors. |
| Precautionary Statement Codes | P260, P264, P270, P280, P301+P312, P305+P351+P338, P310, P314, P330, P337+P313, and P501 (The corresponding statement to each P-code can be found at the GHS Classification page.) |
Other Data
| Transportation | NONH for all modes of transport |
| Under the room temperature and away from light | |
| HS Code | No data available |
| Storage | Under the room temperature and away from light |
| Shelf Life | 2 years |
| Market Price | USD 350/mg |
| Druglikeness | |
| Lipinski rules component | |
| 分子量 | 635.522 |
| HBA | 19 |
| HBD | 3 |
| Matching Lipinski Rules | 1 |
| Veber rules component | |
| Polar Surface Area (PSA) | 269.85 |
| Rotatable Bond (RotB) | 19 |
| Matching Veber Rules | 0 |
| Use Pattern |
| Tenofovir disoproxil fumarate CAS#: 202138-50-9 Pharmaceuticals |
| Tenofovir disoproxil fumarate CAS#: 202138-50-9 treating HBV infection, in combination with 3-[(8aS)-7-[[(4S)-5-ethoxycarbonyl-4-(3-fluoro-2-methylphenyl)-2-thiazol-2-yl-1,4-dihydropyrimidin-6-yl]methyl]-3-oxo-5,6,8,8a-tetrahydro-1H-imidazo[1,5-a]pyrazin-2-yl]-2,2-dimethylpropanoic acid |
| Tenofovir disoproxil fumarate CAS#: 202138-50-9 treatment of HIV |
| Tenofovir disoproxil fumarate CAS#: 202138-50-9 augmenting immune activation in combination with N-carbamimidoyl-5-(1-methylpyrazol-4-yl)naphthalene-2-carboxamide |
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| Caming Pharmaceutical Ltd | http://www.caming.com/ |
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