Sumatriptan
Número de catálogo B127528
Peso molecular: 295.40 g/mol
Clave InChI: KQKPFRSPSRPDEB-UHFFFAOYSA-N
Atención: Solo para uso de investigación. No para uso humano o veterinario.
Patent
US06255502B1
Procedure details
Sumatriptan caprate and gamma-cyclodextrin was complexed by the kneading method. Sumatriptan caprate (1.325 g) and gamma-cyclodextrin (3.675 g) were blended together. Water (6 mL) was added and the mixture ground together in a mortar with a pestle to form a uniform paste. Grinding was continued for 30 minutes. The paste was then dried in a vacuum oven (40° C.; 0 bar) for 48 hours. The solid mass was broken up, passed through a 60 mesh screen and returned to the vacuum oven (40° C.; 0 bar) for 12 hours in order to ensure uniform drying of the complex. Analysis by HPLC for sumatriptan base content, and Karl Fischer for moisture content gave the following results: % sumatriptan base was 16.78% and the moisture content was 6.80%. The complex was characterised by DSC, FT-IR and XRD.
Name
Sumatriptan caprate
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
Name
gamma-cyclodextrin
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
Name
Sumatriptan caprate
Quantity
1.325 g
Type
reactant
Reaction Step Three
Name
gamma-cyclodextrin
Quantity
3.675 g
Type
reactant
Reaction Step Four
Name
Identifiers
|
REACTION_CXSMILES
|
[CH3:1][NH:2][S:3]([CH2:6][C:7]1[CH:8]=[CH:9][C:10]2[NH:15][CH:14]=[C:13]([CH2:16][CH2:17][N:18]([CH3:20])[CH3:19])[C:11]=2[CH:12]=1)(=[O:5])=[O:4].[O-]C(CCCCCCCCC)=O.C(O)[C@H]1O[C@@H]2O[C@H]3[C@H](O)[C@@H](O)[C@@H](O[C@H]4[C@H](O)[C@@H](O)[C@@H](O[C@H]5[C@H](O)[C@@H](O)C(OC6[C@H](O)[C@@H](O)C(C7[C@H](O)[C@@H](O)C(O[C@H]8[C@H](O)[C@@H](O)[C@@H](O[C@H]9[C@H](O)[C@@H](O)[C@@H](O[C@H]1[C@H](O)[C@H]2O)O[C@@H]9CO)O[C@@H]8CO)O[C@@H]7CO)O[C@@H]6CO)O[C@@H]5CO)O[C@@H]4CO)O[C@@H]3CO>O>[CH3:1][NH:2][S:3]([CH2:6][C:7]1[CH:8]=[CH:9][C:10]2[NH:15][CH:14]=[C:13]([CH2:16][CH2:17][N:18]([CH3:20])[CH3:19])[C:11]=2[CH:12]=1)(=[O:5])=[O:4] |f:0.1|
|
Inputs
Step One
|
Name
|
Sumatriptan caprate
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
reactant
|
|
Smiles
|
CNS(=O)(=O)CC=1C=CC2=C(C1)C(=CN2)CCN(C)C.[O-]C(=O)CCCCCCCCC
|
Step Two
|
Name
|
gamma-cyclodextrin
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
reactant
|
|
Smiles
|
C([C@@H]1[C@@H]2[C@@H]([C@H]([C@H](O1)O[C@@H]3[C@H](O[C@@H]([C@@H]([C@H]3O)O)O[C@@H]4[C@H](O[C@@H]([C@@H]([C@H]4O)O)O[C@@H]5[C@H](OC([C@@H]([C@H]5O)O)OC6[C@H](OC([C@@H]([C@H]6O)O)C7[C@H](OC([C@@H]([C@H]7O)O)O[C@@H]8[C@H](O[C@@H]([C@@H]([C@H]8O)O)O[C@@H]9[C@H](O[C@H](O2)[C@@H]([C@H]9O)O)CO)CO)CO)CO)CO)CO)CO)O)O)O
|
Step Three
|
Name
|
Sumatriptan caprate
|
|
Quantity
|
1.325 g
|
|
Type
|
reactant
|
|
Smiles
|
CNS(=O)(=O)CC=1C=CC2=C(C1)C(=CN2)CCN(C)C.[O-]C(=O)CCCCCCCCC
|
Step Four
|
Name
|
gamma-cyclodextrin
|
|
Quantity
|
3.675 g
|
|
Type
|
reactant
|
|
Smiles
|
C([C@@H]1[C@@H]2[C@@H]([C@H]([C@H](O1)O[C@@H]3[C@H](O[C@@H]([C@@H]([C@H]3O)O)O[C@@H]4[C@H](O[C@@H]([C@@H]([C@H]4O)O)O[C@@H]5[C@H](OC([C@@H]([C@H]5O)O)OC6[C@H](OC([C@@H]([C@H]6O)O)C7[C@H](OC([C@@H]([C@H]7O)O)O[C@@H]8[C@H](O[C@@H]([C@@H]([C@H]8O)O)O[C@@H]9[C@H](O[C@H](O2)[C@@H]([C@H]9O)O)CO)CO)CO)CO)CO)CO)CO)O)O)O
|
Step Five
|
Name
|
|
|
Quantity
|
6 mL
|
|
Type
|
solvent
|
|
Smiles
|
O
|
Conditions
Other
|
Conditions are dynamic
|
1
|
|
Details
|
See reaction.notes.procedure_details.
|
Workups
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
the mixture ground together in a mortar with a pestle to form a uniform paste
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
Grinding
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
The paste was then dried in a vacuum oven (40° C.; 0 bar) for 48 hours
|
|
Duration
|
48 h
|
WAIT
|
Type
|
WAIT
|
|
Details
|
returned to the vacuum oven (40° C.; 0 bar) for 12 hours in order
|
|
Duration
|
12 h
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
to ensure uniform drying of the complex
|
Outcomes
Product
Details
Reaction Time |
30 min |
|
Name
|
|
|
Type
|
product
|
|
Smiles
|
CNS(=O)(=O)CC=1C=CC2=C(C1)C(=CN2)CCN(C)C
|
Source
|
Source
|
Open Reaction Database (ORD) |
|
Description
|
The Open Reaction Database (ORD) is an open-access schema and infrastructure for structuring and sharing organic reaction data, including a centralized data repository. The ORD schema supports conventional and emerging technologies, from benchtop reactions to automated high-throughput experiments and flow chemistry. Our vision is that a consistent data representation and infrastructure to support data sharing will enable downstream applications that will greatly improve the state of the art with respect to computer-aided synthesis planning, reaction prediction, and other predictive chemistry tasks. |
