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[ CAS No. 330808-88-3 ] {[proInfo.proName]}

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Chemical Structure| 330808-88-3
Chemical Structure| 330808-88-3
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Product Details of [ 330808-88-3 ]

CAS No. :330808-88-3 MDL No. :MFCD08458876
Formula : C23H39ClN6O7S Boiling Point : -
Linear Structure Formula :- InChI Key :FBCDRHDULQYRTB-UHFFFAOYSA-N
M.W : 579.11 Pubchem ID :135413545
Synonyms :
Vardenafil (hydrochloride hydrate);BAY38-9456;Vivanza;Staxyn;Levitra;Vardenafil HCl;Vardenafil HCl Trihydrate

Calculated chemistry of [ 330808-88-3 ]

Physicochemical Properties

Num. heavy atoms : 38
Num. arom. heavy atoms : 15
Fraction Csp3 : 0.52
Num. rotatable bonds : 8
Num. H-bond acceptors : 11.0
Num. H-bond donors : 4.0
Molar Refractivity : 154.63
TPSA : 148.97 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -8.53 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 1.84
Log Po/w (WLOGP) : 3.0
Log Po/w (MLOGP) : -0.23
Log Po/w (SILICOS-IT) : 2.42
Consensus Log Po/w : 1.41

Druglikeness

Lipinski : 2.0
Ghose : None
Veber : 1.0
Egan : 1.0
Muegge : 1.0
Bioavailability Score : 0.17

Water Solubility

Log S (ESOL) : -4.35
Solubility : 0.0256 mg/ml ; 0.0000443 mol/l
Class : Moderately soluble
Log S (Ali) : -4.59
Solubility : 0.0149 mg/ml ; 0.0000258 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -6.21
Solubility : 0.000353 mg/ml ; 0.00000061 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 4.7

Safety of [ 330808-88-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 330808-88-3 ]

* 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 [ 330808-88-3 ]

[ 330808-88-3 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 224785-90-4 ]
  • 1-[[3-(1,4-dihydro-5-methyl-4-oxo-7-propylimidazo[5,1-f][1,2,4]triazin-2-yl)-4-ethoxyphenyl]sulfonyl]-4-ethylpiperazine dihydrochloride dihydrate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; water In acetone at 29 - 55℃; for 0.5h; 5 EXAMPLE 5 Preparation of the Dihydrate of Vardenafil Dihydrochloride 11 g of vardenafil free base was taken into a round bottom flask followed by the addition of 39 ml of a mixture of acetone and water in the ratio of 12:1 v/v at 29° C. 3 ml of 36% concentrated hydrochloric acid was added to the above reaction mass and heated to a temperature of 55° C. and maintained for 30 minutes. It was then cooled to temperature of about 45° C. followed by distillation under vacuum of 280 torr and 45° C. The resultant reaction mass was cooled to 20° C. followed by the addition of 50 ml of diethyl ether with simultaneous stirring and the reaction mass was filtered at 20° C. The solid material was washed with 20 ml of ether and the material was dried at 40° C. for 1.5 hours to yield 10.5 g of the dihydrate of vardenafil dihydrochloride. Moisture content: 6% by weight. Melting point range: 214° C. to 232° C.
  • 2
  • [ 224785-91-5 ]
  • [ 330808-88-3 ]
YieldReaction ConditionsOperation in experiment
Stage #1: vardenafil hydrochloride With sodium hydroxide; water at 30℃; Stage #2: With hydrogenchloride; water In acetone at 3 - 45℃; for 0.75h; 7 EXAMPLE 7 Preparation of the Trihydrate of Vardenafil Monohydrochloride 14 g of vardenafil hydrochloride was taken into a round bottom flask followed by the addition of 70 ml water and the pH of the reaction mass was adjusted using sodium hydroxide to 11 at 30° C. 280 ml of dichloromethane was added to the above reaction mass and the layers were separated. The organic layer was dried over sodium sulfate and the organic layer was transferred into a round bottom flask and subjected to heating for distillation at 40° C. for 1.5 hours. The solid material was transferred into a round bottom flask and 36 ml of a mixture of acetone and water in 12:1 ratio was added with stirring, then 2.2 ml of 36% aqueous hydrochloric acid was added with stirring. The reaction mass was heated to a temperature of about 45° C. and the undissolved particles were removed by filtration. The filtrate was taken into a round bottom flask and cooled to 5° C., maintained for 45 minutes at 3 to 5° C. followed by the filtration of the solid which was then subjected to suction drying and finally dried at 40° C. to yield 9.0 g of the trihydrate of vardenafil monohydrochloride.
  • 3
  • 1-[[3-(1,4-dihydro-5-methyl-4-oxo-7-propylimidazo[5,1-f][1,2,4]triazin-2-yl)-4-ethoxyphenyl]sulfonyl]-4-ethylpiperazine dihydrochloride dihydrate [ No CAS ]
  • [ 224785-90-4 ]
  • 1-[[3-(1,4-dihydro-5-methyl-4-oxo-7-propylimidazo[5,1-f][1,2,4]triazin-2-yl)-4-ethoxyphenyl]sulfonyl]-4-ethylpiperazine dihydrochloride monohydrate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: vardenafil With water In acetone at 28℃; for 0.166667h; Stage #2: With hydrogenchloride; water In acetone at 5 - 55℃; for 0.5h; Stage #3: 1-[[3-(1,4-dihydro-5-methyl-4-oxo-7-propylimidazo[5,1-f][1,2,4]triazin-2-yl)-4-ethoxyphenyl]sulfonyl]-4-ethylpiperazine dihydrochloride dihydrate In acetone at 3℃; 4 EXAMPLE 4 Preparation of the Monohydrate of Vardenafil Dihydrochloride 10 g of vardenafil free base was taken into a round bottom flask and a mixture of 24 ml of acetone and 2 ml of water (a ratio of 12:1 v/v) was added and stirred for about 10 minutes at 28° C. 3 ml of 36% conc. aqueous hydrochloric acid was added with stirring to the reaction mixture and heated to a temperature of 55° C. for 30 minutes. The reaction mixture was cooled to a temperature of 20° C. and then further cooled to a temperature of about 5° C. The reaction mixture was then seeded with vardenafil dihydrochloride dihydrate at 3° C. The solid was filtered and washed with 15 ml of acetone and subjected to suction drying. The solid mass was transferred into an oven and dried at a temperature of 44° C. for 2 hours to yield 8.4 g of the monohydrate of vardenafil dihydrochloride. Moisture content: 3.6% by weight. Melting point range: 233° C. to 238° C.
  • 4
  • 1-[[3-(1,4-dihydro-5-methyl-4-oxo-7-propylimidazo[5,1-f][1,2,4]triazin-2-yl)-4-ethoxyphenyl]sulfonyl]-4-ethylpiperazine dihydrochloride dihydrate [ No CAS ]
  • [ 224785-90-4 ]
  • 1-[[3-(1,4-dihydro-5-methyl-4-oxo-7-propylimidazo[5,1-f][1,2,4]triazin-2-yl)-4-ethoxyphenyl]sulfonyl]-4-ethylpiperazine dihydrochloride trihydrate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: vardenafil With hydrogenchloride; water In acetone at 5 - 56℃; for 0.5h; Stage #2: 1-[[3-(1,4-dihydro-5-methyl-4-oxo-7-propylimidazo[5,1-f][1,2,4]triazin-2-yl)-4-ethoxyphenyl]sulfonyl]-4-ethylpiperazine dihydrochloride dihydrate In acetone at 3℃; 6 EXAMPLE 6 Preparation of the Trihydrate of Vardenafil Dihydrochloride 24 g of vardenafil free base was taken into a round bottom flask followed by the addition of 60 ml of a mixture of acetone and water in the ratio of 12:1 v/v at 28° C. 7.2 ml of 36% aqueous hydrochloric acid was added to the above reaction mass and heated to 56° C., and maintained for 30 minutes. It was then cooled to temperature of 5° C. and the reaction mass was then seeded with vardenafil dihydrochloride dihydrate at 3° C. to get a solid. The reaction material was filtered by applying vacuum of about 280 torr, washed with 35 ml of acetone and subjected to suction drying. The solid mass was transferred into a oven and dried at a temperature of 45° C. for 1.5 hours to yield 23.6 g of the trihydrate of vardenafil dihydrochloride. Moisture content: 12.1% by weight. Melting point range: 224° C. to 239° C.
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