Structure of 6325-93-5
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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New Liquid Biomaterials for Nanoemulsion-mediated Drug Delivery
Padilla, Marshall Scott ;
Abstract: Most potent therapeutics fail to reach clinical trials and FDA-approval due to their inability to reach their target in a safe and controlled manner. To overcome these barriers, nanotechnology can be employed to create vehicles that aid in the delivery of drugs. One promising class of drug delivery vehicles are nanoemulsions, which are nanometer-sized particles that contain a hydrophobic droplet that houses and protects the therapeutics. Nanoemulsions have seen success in the delivery of drugs as several nanoemulsion formulations have received FDA-approved. However, despite their success, one of their limiting factors is their lack of diverse hydrophobic components. Typically, the hydrophobic droplet is a lipid, and as a result, only drugs that are lipophilic can be dissolved. This means that hydrophilic small molecule and biological therapeutics cannot be formulated, significantly reducing the potential of this drug delivery vehicle.
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CAS No. : | 6325-93-5 |
Formula : | C6H6N2O4S |
M.W : | 202.19 |
SMILES Code : | O=S(C1=CC=C([N+]([O-])=O)C=C1)(N)=O |
MDL No. : | MFCD00007937 |
InChI Key : | QWKKYJLAUWFPDB-UHFFFAOYSA-N |
Pubchem ID : | 22784 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 13 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 2 |
Num. H-bond acceptors | 5.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 46.26 |
TPSA ? Topological Polar Surface Area: Calculated from |
114.36 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
0.1 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
0.64 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.32 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
-0.74 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
-2.11 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
-0.16 |
Log S (ESOL):? ESOL: Topological method implemented from |
-1.71 |
Solubility | 3.98 mg/ml ; 0.0197 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.62 |
Solubility | 0.489 mg/ml ; 0.00242 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-1.35 |
Solubility | 9.03 mg/ml ; 0.0447 mol/l |
Class? Solubility class: Log S scale |
Soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
High |
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg |
No |
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) |
No |
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) |
No |
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) |
No |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
No |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) |
No |
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) |
No |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-7.08 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from |
0.0 |
Ghose? Ghose filter: implemented from |
None |
Veber? Veber (GSK) filter: implemented from |
0.0 |
Egan? Egan (Pharmacia) filter: implemented from |
0.0 |
Muegge? Muegge (Bayer) filter: implemented from |
0.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
0.55 |
PAINS? Pan Assay Interference Structures: implemented from |
0.0 alert |
Brenk? Structural Alert: implemented from |
2.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
2.07 |
* 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 |
---|---|---|
69% | Dissolve 1 g of p-nitrobenzenesulfonamide in DMF and add 1.0 g of sodium hydride under an ice bath. Stir for 30 minutes and add dropwise.2.1 g of iodomethane was stirred at room temperature for 2 hours and the reaction was complete. Insoluble material was filtered off, water was added, solids were stirred, precipitated, filtered, and dried to give a pale yellow solid which was directly put into the next reaction.2.3g of the above product was added to methanol and 1g of 10% palladium on carbon was added. A few drops of acetic acid were added dropwise at 50C.After 6 hours, at the end of the reaction, the catalyst was removed by filtration, washed twice with dichloromethane, and the combined filtrates were evaporated to remove the solvent and purified by column chromatography.(Yellowish solid, 1.38g, yield 69%. |
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