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Details

Stereochemistry ACHIRAL
Molecular Formula 6Cl.Pt.2H4N
Molecular Weight 443.879
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AMMONIUM CHLOROPLATINATE

SMILES

[NH4+].[NH4+].[Cl-].[Cl-].[Cl-].[Cl-].[Cl-].[Cl-].[Pt+4]

InChI

InChIKey=PCCGQTHFYHJATL-UHFFFAOYSA-J
InChI=1S/6ClH.2H3N.Pt/h6*1H;2*1H3;/q;;;;;;;;+4/p-4

HIDE SMILES / InChI

Molecular Formula Pt
Molecular Weight 195.084
Charge 4
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 ClH
Molecular Weight 36.461
Charge 0
Count
MOL RATIO 6 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 2 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Diamminedichlorodihydroxyplatinum IV is the platinum-based antineoplasticis agent. Oxaliplatin is cis, cis, trans- isomer of Diamminedichlorodihydroxyplatinum IV. Oxaliplatin show high stability and therefore can be utilized orally for outpatient care. Although oxoplatin is capable of binding directly to DNA after prolonged incubation, platinum(IV) agents are considered to be largely inert prodrugs that are converted to highly cytotoxic platinum(II) compounds by reducing substances, enzymes, or microenvironmental conditions. Reaction of oxoplatin with 0.1 M hydrogen chloride mimicking gastric acid yields cis-diammine-tetrachlorido-platinum(IV) (DATCP[IV]), which exhibits two-fold increased activity. The oxoplatin metabolite DATCP(IV) constitutes a potent cytotoxic derivative that may be produced by gastric acid or acidic areas prevailing in larger solid tumors, depending on the respective pharmaceutical formulation of oxoplatin.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

PubMed

Sample Use Guides

In Vivo Use Guide
After single i.v. administration of trans-dihydroxy-cis-dichlorodiammine-platinum(IV), the LD50 values have been calculated to range between 80 and 130 mg/kg in mice, and between 22 and 45 mg/kg in rats.
Route of Administration: Intravenous
In Vitro Use Guide
The DNA binding/capture studies were done in a total volume of 20 μL containing 38.5 μM (bp) pBR322 DNA (New EnglandBioLabs Inc.), in 12 mM HEPES, N-(2-hydroxyethyl)-piperazine-N'-2-ethanesulfonicacid (pH 7.4) buffer or, when sodium bicarbonate was present, in 12 mM HEPES buffer plus 12 mM sodium bicarbonate (pH 7.4). The two reducing agents used were glutathione (GSH, 2 mM) and ascorbic acid (AsA, 50 μM). Stock solutions of the platinum compound Diamminedichlorodihydroxyplatinum IV in distilled water was in the range of 40–650 μM. Appropriate volumes of the stock solutions were added to solutions containing the buffer and DNA to give the final concentrations given earlier and values of r, where r=[platinum compound]/[DNA-bp], given in the captions to figures. The samples were incubated at 37 °C for 24 h in sealed Eppendorf tubes after which time 2.5 μL of a loading dye containing 50% glycerol, 0.25% bromophenol blue and 0.25% xylene cyanol was added. An 8 μL volume of each sample containing the loading dye was loaded in the wells of a 1% agarose gel. Electrophoresis was carried out for a period of ~4 h, at 100 V. After electrophoresis, the gel was immersed in 300 mL of deionized water containing 300 μL of a 0.5 mg/mL solution of ethidium bromide for 30 min to stain the DNA, and then soaked in water alone for 15 min to de-stain the background of the gel. A digital image of the stained gel was captured using a Kodak Gel Logic 100 imaging system equipped with Fisher Biotech IT-88A transilluminator.
Substance Class Chemical
Record UNII
1653N9XMIC
Record Status Validated (UNII)
Record Version