Phosphate → Vincristine

HRID 2085903Notes

Reaction equation

[CH3:1][CH2:2][C@@:3]1([OH:60])[CH2:21][N:19]2[CH2:20][C@@H:5]([CH2:6][C@:7]([C:56]([O:58][CH3:59])=[O:57])([C:22]3[CH:23]=[C:24]4[C@:32]56[C@@H:36]7[C@:37]([CH2:52][CH3:53])([C@@H:41]([O:48][C:49]([CH3:51])=[O:50])[C@:42]([OH:47])([C:43]([O:45][CH3:46])=[O:44])[C@@H:31]5[N:30]([CH:54]=[O:55])[C:25]4=[CH:26][C:27]=3[O:28][CH3:29])[CH:38]=[CH:39][CH2:40][N:35]7[CH2:34][CH2:33]6)[C:8]3[NH:16][C:15]4[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=4[C:9]=3[CH2:17][CH2:18]2)[CH2:4]1.OS(O)(=O)=O.C(O)[C@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O.C([O-])(=O)C.[Na+].C([O-])(=O)CC(CC([O-])=O)(C([O-])=O)O.P([O-])([O-])([O-])=O>>[CH3:1][CH2:2][C@@:3]1([OH:60])[CH2:21][N:19]2[CH2:20][C@@H:5]([CH2:6][C@:7]([C:56]([O:58][CH3:59])=[O:57])([C:22]3[CH:23]=[C:24]4[C@:32]56[C@@H:36]7[C@:37]([CH2:52][CH3:53])([C@@H:41]([O:48][C:49]([CH3:51])=[O:50])[C@:42]([OH:47])([C:43]([O:45][CH3:46])=[O:44])[C@@H:31]5[N:30]([CH:54]=[O:55])[C:25]4=[CH:26][C:27]=3[O:28][CH3:29])[CH:38]=[CH:39][CH2:40][N:35]7[CH2:34][CH2:33]6)[C:8]3[NH:16][C:15]4[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=4[C:9]=3[CH2:17][CH2:18]2)[CH2:4]1

Participants

Reactant 5

HCID 1061Phosphate

HCID 6251Mannitol

HCID 31348Citrate

HCID 249332Vincristine Sulfate

HCID 517045Sodium Acetate

Product 1

HCID 5978Vincristine

Procedure

Liposome-encapsulated vincristine (Vincristine Sulfate Liposome Injection) was prepared using a six vial kit. Vials 1 and 2 contained a vincristine sulfate solution (1 mg/mL Vincasar PFS® SP Pharmaceuticals LLC, Albuqueque, N.Mex.) in buffer comprising mannitol and sodium acetate, pH 4.5-4.7, vial 3 contained empty liposomes (100 mg/mL Sphingomyelin/Cholesterol liposomes, at a ratio of between about 60/40 to 50/50, or more preferably 55/45 mol %/mol %) in buffer comprising 300 mM citrate at pH 4.0, vials 4 and 5 contained an alkaline phosphate buffer (14.2 mg/mL dibasic sodium phosphate hepta hydrate), and vial 6 was an empty, sterile vial. The foregoing empty liposomes were prepared using thin film hydration and standard extrusion techniques, as described in U.S. Pat. No. 5,741,516.

Workup

customThe foregoing empty liposomes were prepared

Sources & evidence

ORD record: ord-7d2a0976914c43ba9e17fd56688269d0
Source dataset: uspto-grants-2004_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06723338B1

Reaction notes

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