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CAS No. : | 29094-61-9 | MDL No. : | MFCD00072159 |
Formula : | C21H27N5O4S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | ZJJXGWJIGJFDTL-UHFFFAOYSA-N |
M.W : | 445.54 | Pubchem ID : | 3478 |
Synonyms : |
K 4024;CP 28720;Ozidia;Minodiab;Melizide;Glydiazinamide;Minidiab;Glucotrol;TK 1320
|
Num. heavy atoms : | 31 |
Num. arom. heavy atoms : | 12 |
Fraction Csp3 : | 0.43 |
Num. rotatable bonds : | 10 |
Num. H-bond acceptors : | 6.0 |
Num. H-bond donors : | 3.0 |
Molar Refractivity : | 115.3 |
TPSA : | 138.53 Ų |
GI absorption : | Low |
BBB permeant : | No |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | Yes |
CYP2D6 inhibitor : | Yes |
CYP3A4 inhibitor : | Yes |
Log Kp (skin permeation) : | -7.66 cm/s |
Log Po/w (iLOGP) : | 2.51 |
Log Po/w (XLOGP3) : | 1.91 |
Log Po/w (WLOGP) : | 3.16 |
Log Po/w (MLOGP) : | 0.21 |
Log Po/w (SILICOS-IT) : | 1.67 |
Consensus Log Po/w : | 1.89 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 1.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.43 |
Solubility : | 0.165 mg/ml ; 0.00037 mol/l |
Class : | Soluble |
Log S (Ali) : | -4.44 |
Solubility : | 0.0161 mg/ml ; 0.0000361 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -6.66 |
Solubility : | 0.0000975 mg/ml ; 0.000000219 mol/l |
Class : | Poorly soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 2.0 |
Synthetic accessibility : | 3.33 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H320-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With iron(III)-acetylacetonate In methanol at 20 - 30℃; for 6 h; | The reaction bottle II compounds are point pen 3.77 g (10 mmol), methanol 20 ml, cyclohexylamine 1.29 g (13 mmol), Fe (acac)317. 6 Mg (0.05 mmol, 0.5percent), the system vacuum to -0.098 mpa, subsequently access CO gas to the atmospheric pressure, repeated 3 times, thermal insulation 20 - 30oC stirring reaction 6 h. After the reaction is finished, add 30 ml water dilution, for 2 N hydrochloric acid to adjust the pH=3 - 4, filtering, the filter cake is washed 10 ml * 2 times, 70 - 80oC blast drying to obtain the Glipizide 3.79 g, HPLC method for determining content of 98.8percent, yield 85percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With water; sodium methylate In methanol at 85℃; | 4-(2-aminoethyl)-N-(cyclohexylcarbamoyl)benzenesulfonamide (25g, 0.076moles) and methyl 5-methylpyrazine-2-carboxylate (12.27g, 0.O8moles) were charged and mixed in a reaction vessel. Solution of sodium methoxide in methanol (33.17g, 0.l5moles) was added to the vessel. The mixture was stirred at 85°C for lhr and second lot of methyl 5-methylpyrazine-2-carboxylate (1. 17g, 0.OO7moles) and 25percent sodium methoxide solution (1.7g, 0.OO7moles) was added to the mass.After completion of reaction, the reaction mixture was cooled to 25°C to 35°C and water (125m1) was added to it. The mixture was acidified using diluted hydrochloric acid to precipitate out the solid. The solid obtained was filtered, washed with water (2x25m1) and dried to afford Glipizide (29g).Yield: 84percent Purity: 96.89percent |
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