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Details

Stereochemistry ACHIRAL
Molecular Formula 2Cl.Pt.2HO.2H3N
Molecular Weight 334.066
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DIAMMINEDICHLORODIHYDROXYPLATINUM IV

SMILES

N.N.[OH-].[OH-].[Cl-].[Cl-].[Pt+4]

InChI

InChIKey=WIBKDBYFIKUYJQ-UHFFFAOYSA-J
InChI=1S/2ClH.2H3N.2H2O.Pt/h2*1H;2*1H3;2*1H2;/q;;;;;;+4/p-4

HIDE SMILES / InChI

Molecular Formula HO
Molecular Weight 17.0073
Charge -1
Count
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
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula Pt
Molecular Weight 195.084
Charge 4
Count
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
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/24515615 | https://www.ncbi.nlm.nih.gov/pubmed/19587824 | https://www.ncbi.nlm.nih.gov/pubmed/7737155 | https://www.ncbi.nlm.nih.gov/pubmed/7923207

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

Sources: Zhurnal Neorganicheskoi Khimii Volume 2, Pages 2349-59, Journal, 1957

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: CHEMBL2311221
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Reinterpretation of the vibrational spectroscopy of the medicinal bioinorganic synthon c,c,t-[Pt(NH3)2Cl2(OH)2].
2014-06
Gene expressions changes in bronchial epithelial cells: markers for respiratory sensitizers and exploration of the NRF2 pathway.
2014-03
Identification of contact and respiratory sensitizers according to IL-4 receptor α expression and IL-2 production.
2012-04-15
Gene markers in dendritic cells unravel pieces of the skin sensitization puzzle.
2010-07-01
A plasmacytoid dendritic cell (CD123+/CD11c-) based assay system to predict contact allergenicity of chemicals.
2009-10-01
Gene profiles of THP-1 macrophages after in vitro exposure to respiratory (non-)sensitizing chemicals: identification of discriminating genetic markers and pathway analysis.
2009-09
THP-1 monocytes but not macrophages as a potential alternative for CD34+ dendritic cells to identify chemical skin sensitizers.
2009-04-15
Gene profiles of a human alveolar epithelial cell line after in vitro exposure to respiratory (non-)sensitizing chemicals: identification of discriminating genetic markers and pathway analysis.
2009-02-25
Role of p38 MAPK in the selective release of IL-8 induced by chemical allergen in naive THp-1 cells.
2008-03
Platinum group metal sensitivity: reactivity to platinum group metal salts in platinum halide salt-sensitive workers.
1987-12
Patents

Sample Use Guides

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
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
Created
by admin
on Mon Mar 31 19:52:41 GMT 2025
Edited
by admin
on Mon Mar 31 19:52:41 GMT 2025
Record UNII
VVI1VF51WL
Record Status Validated (UNII)
Record Version
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Name Type Language
DIAMMINEDICHLORODIHYDROXYPLATINUM IV
Common Name English
PLATINUM(4+) CHLORIDE HYDROXIDE AMMONIATE (1:2:2:2)
Preferred Name English
Code System Code Type Description
FDA UNII
VVI1VF51WL
Created by admin on Mon Mar 31 19:52:41 GMT 2025 , Edited by admin on Mon Mar 31 19:52:41 GMT 2025
PRIMARY
MESH
C043804
Created by admin on Mon Mar 31 19:52:41 GMT 2025 , Edited by admin on Mon Mar 31 19:52:41 GMT 2025
PRIMARY
PUBCHEM
123714
Created by admin on Mon Mar 31 19:52:41 GMT 2025 , Edited by admin on Mon Mar 31 19:52:41 GMT 2025
PRIMARY
CAS
53261-25-9
Created by admin on Mon Mar 31 19:52:41 GMT 2025 , Edited by admin on Mon Mar 31 19:52:41 GMT 2025
PRIMARY