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[ CAS No. 84057-84-1 ] {[proInfo.proName]}

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Chemical Structure| 84057-84-1
Chemical Structure| 84057-84-1
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Product Citations

Product Citations

Fouad S. Moghrabi ; Aktham Aburub ; Hala M. Fadda DOI: PubMed ID:

Abstract: Purpose: pH-dependent drug-drug interactions (DDIs) with poorly soluble, weakly basic drugs may lead to clinical implications. Dasatinib is a tyrosine kinase inhibitor with reduced absorption in patients on acid-reducing agents (ARAs). The objective of this study is to investigate the influence of gastric pH on dasatinib supersaturation and determine if vitamin C (L-ascorbic acid) can improve dasatinib concentrations under simulated hypochlorhydric gastric conditions. Methods: A dynamic, in vitro, multi-compartment, simulated stomach duodenum (SSD) model mimicking fluid volumes and transfer rates was used to investigate the concentration of BCS class IIb drugs versus time curves. Dasatinib and lamotrigine were explored under normal, fasted, simulated gastric fluids (pH 2) (FaSGF), hypochlorhydric simulated gastric fluids (pH 4.5) (FaSGFhypo) and FaSGFhypo with 1000 mg of vitamin C. Results: Significant supersaturation of dasatinib was observed in the duodenum compartment of the SSD model in FaSGF. A 90% reduction in dasatinib AUC∞ was observed in FaSGFhypo. Upon addition of vitamin C to FaSGFhypo, drug concentrations were restored to those observed in FaSGF. Lamotrigine AUC∞ in the duodenal compartment were similar in both FaSGF and FaSGFhypo. The in vitro trends observed for dasatinib and lamotrigine are reflective of the trends observed in vivo in subjects receiving treatment with ARAs. Conclusions: The SSD model serves as a good in vitro tool for assessing the effect of pH-dependent DDIs on bioavailability of weakly basic drugs with solubility/ dissolution limited absorption. Vitamin C provides a promising approach for improving bioavailability of poorly soluble, weakly basic drugs in hypochlorhydric patients.

Keywords: Dissolution ; Ionization ; In vitro in?vivo correlations ; Proton pump inhibitors ; Oral drug delivery

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Product Details of [ 84057-84-1 ]

CAS No. :84057-84-1 MDL No. :MFCD00865333
Formula : C9H7Cl2N5 Boiling Point : -
Linear Structure Formula :- InChI Key :PYZRQGJRPPTADH-UHFFFAOYSA-N
M.W : 256.09 Pubchem ID :3878
Synonyms :
LTG;BW430C;Lamotrigine, Lamictal, BW-430C, Crisomet, Lamictin, Lamitor
Chemical Name :6-(2,3-Dichlorophenyl)-1,2,4-triazine-3,5-diamine

Calculated chemistry of [ 84057-84-1 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 64.09
TPSA : 90.71 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.85 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.51
Log Po/w (XLOGP3) : 1.42
Log Po/w (WLOGP) : 2.03
Log Po/w (MLOGP) : 1.34
Log Po/w (SILICOS-IT) : 1.75
Consensus Log Po/w : 1.61

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.81
Solubility : 0.395 mg/ml ; 0.00154 mol/l
Class : Soluble
Log S (Ali) : -2.93
Solubility : 0.301 mg/ml ; 0.00118 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.32
Solubility : 0.0124 mg/ml ; 0.0000483 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.72

Safety of [ 84057-84-1 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P301+P310 UN#:2811
Hazard Statements:H301 Packing Group:Ⅲ
GHS Pictogram:

Application In Synthesis of [ 84057-84-1 ]

* 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.

  • Downstream synthetic route of [ 84057-84-1 ]

[ 84057-84-1 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 6574-97-6 ]
  • [ 2582-30-1 ]
  • [ 84057-84-1 ]
YieldReaction ConditionsOperation in experiment
With aqueous nitric acid; In dimethyl sulfoxide; EXAMPLE 1 Preparation of 3,5-Diamino-6-(2,3-dichlorophenyl)-1,2,4-triazine A solution of <strong>[6574-97-6]2,3-dichlorophenyl cyanide</strong> (32g, 0.26M) in dimethylsulphoxide (80mls) was added dropwise to a stirred suspension of aminoguanidine bicarbonate (81.67g, 0.6M) which had been treated with 8N aqueous nitric acid (400mls) at a temperature of about 25° C. The mixture was stirred for three hours, then left to stand at room temperature for seven days. The cooled mixture was stirred and basified with 0.880 aqueous ammonia (400mls) at 20° C., then stirred with ice cooling for thirty minutes, filtered and the resulting solid washed thoroughly with water and finally dried in vacuo.
With potassium hydroxide; aqueous nitric acid; In methanol; (2S)-N-methyl-1-phenylpropan-2-amine hydrate; dimethyl sulfoxide; Example 1 Preparation of 3,5-Diamino-6-(2,3-dichlorophenyl)-1,2,4-triazine. A solution of <strong>[6574-97-6]2,3-dichlorophenyl cyanide</strong> (32g, 0.16M) in dimethylsulphoxide (80mls) was added dropwise to a stirred suspension of aminoguanidine bicarbonate (81.67g, 0.6M) which had been treated with 8N aqueous nitric acid (400mls) at a temperature of about 25°C. The mixture was stirred for three hours, then left to stand at room temperature for seven days. The cooled mixture was stirred and basified with 0.880 aqueous ammonia (400mls) at 20°C, then stirred with ice cooling for thirty minutes, filtered and the resulting solid washed thoroughly with water and finally dried in vacuo . The above solid was added to a 10percent solution of potassium hydroxide pellets in methanol (400mls) and the solution heated to reflux for one and a half hours. When cool the solution was evaporated down in vacuo , treated with ice water (800mls) then stirred for thirty minutes and filtered. The residue was dried and recrystallized for isopropanol to give 3,5-Diamino-6-(2,3-dichlorophenyl)-1,2,4-triazine. Yield 6.8g (15.6percent), m.p. 216-218°C.
  • 2
  • [ 71-23-8 ]
  • [ 6574-97-6 ]
  • [ 2582-30-1 ]
  • [ 84057-84-1 ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide; sulfuric acid; In water; acetonitrile; Example 2 Preparation of 3,5-Diamino-6-(2,3-dichlorophenyl)-1,2,4-triazine. Aminoguanidine bicarbonate (48.1g, 0.354M), followed by a solution of <strong>[6574-97-6]2,3-dichlorophenyl cyanide</strong> (40.0g, 0.2M) in acetonitrile (160mls), was added to a stirred solution of concentrate sulphuric acid (441g) in water (240mls). The mixture was stirred at 20-30°C for forty-eight hours and then filtered. The solid was added to a cooled solution of sodium hydroxide (28g) in water (150mls) below 30°C. The suspension was filtered and the resulting solid washed thoroughly with water and dried at 80°C. The above solid was added to propan-1-ol (308mls) and the solution heated to reflux for one and a half hours. When cool the solid was filtered, dried at 100°C and then recrystallized from propan-1-ol to give 3,5-Diamino-6-(2,3-dichlorophenyl)-1,2,4-triazine. Yield 21.0g (41percent), m.p. 216-218°C.
  • 3
  • [ 104405-59-6 ]
  • [ 151169-74-3 ]
  • [ 84057-84-1 ]
YieldReaction ConditionsOperation in experiment
87.4% With 2,6-iPr2C6H3NC(4-CH3OC6H4)NHPy; palladium dichloride; In N,N-dimethyl-formamide; at 90℃;Inert atmosphere; 2,3-Dichlorobenzeneboronic acid (0.95 g, 5 mmol), 3,5-diamino 6-bromo-1,2,4-triazine (0.95 g, 5 mmol), potassium phosphate (1.09 g, 3.44 mmol) ), PdCl 2 (0.05 g, 10%, w/w%), ligand L4 (0.040 g, 0.1 mmol) was added to a mixed solution of DMF (30 mL), the system was replaced with nitrogen 4 times, under nitrogen protection at 90 C reacted overnight. The reaction was completely detected by TLC, cooled to room temperature, filtered, and the filtrate was diluted with ethyl acetate (300 mL), and washed three times with water (100 mL), the organic phase was evaporated to remove solvent, and the residue was purified by flash column chromatography The triazine was 1.12 g, and the yield was 87.4%.
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