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Details

Stereochemistry ACHIRAL
Molecular Formula C6H13N.2C2H3O2.2Cl.Pt.H3N
Molecular Weight 500.283
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge -4

SHOW SMILES / InChI
Structure of SATRAPLATIN

SMILES

N.[Cl-].[Cl-].[Pt].CC([O-])=O.CC([O-])=O.NC1CCCCC1

InChI

InChIKey=QFDCPOONOIIAOS-UHFFFAOYSA-J
InChI=1S/C6H13N.2C2H4O2.2ClH.H3N.Pt/c7-6-4-2-1-3-5-6;2*1-2(3)4;;;;/h6H,1-5,7H2;2*1H3,(H,3,4);2*1H;1H3;/p-4

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
MOL RATIO 2 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula H3N
Molecular Weight 17.0305
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C6H13N
Molecular Weight 99.1741
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C2H3O2
Molecular Weight 59.044
Charge -1
Count
MOL RATIO 2 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula Pt
Molecular Weight 195.084
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Satraplatin is a fourth-generation platinum-based anticancer drug developed by GPC Biotech, Inc. Unlike its predecessors cisplatin and carboplatin, which were administered intravenously, satraplatin was developed for oral administration. Satraplatin mediates its action through the formation of DNA adducts and inter- and intra-strand crosslinks. These adducts distort the DNA template with a deceleration of cells in S phase followed with G2 phase arrest. Satraplatin also inhibits DNA replication and transcription and induces signal transduction pathway, leading to cell cycle arrest and apoptosis. Satraplatin was investigated in phase III clinical trials against metastatic castrate-resistant prostate cancer. Despite the improvement in progression-free survival and palliation, overall survival was not improved with satraplatin therapy. The median survival was 61.3 weeks in the satraplatin group and 61.4 weeks in the prednisone and placebo group. In July 2007, GPC Biotech announced the withdrawal of the New Drug Application (NDA) for satraplatin, and the development of the drug was discontinued.

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
Substance Class Chemical
Record UNII
8D7B37T28G
Record Status Validated (UNII)
Record Version