Details
Stereochemistry | ACHIRAL |
Molecular Formula | 2Cl.Pt.2H3N |
Molecular Weight | 300.0447 |
Optical Activity | NONE |
Additional Stereochemistry | Yes |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
Stereo Comments | SQUARE PLANAR 4-2 (SP4-2) |
SHOW SMILES / InChI
SMILES
[Cl-].[Cl-].N.N.[Pt+2]
InChI
InChIKey=LXZZYRPGZAFOLE-UHFFFAOYSA-L
InChI=1S/2ClH.2H3N.Pt/h2*1H;2*1H3;/q;;;;+2/p-2
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/24435208ftp://ftp.nrg.eu/pub/www/nrg/nrglib/2004/immobilisation_of_iodine.pdfhttps://www.accessdata.fda.gov/drugsatfda_docs/label/2015/018057s083lbl.pdfCurator's Comment:: description was created based on several sources, including
https://www.drugbank.ca/drugs/DB00515 | https://www.ncbi.nlm.nih.gov/pubmed/27736024 | https://www.ncbi.nlm.nih.gov/pubmed/25159039
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24435208ftp://ftp.nrg.eu/pub/www/nrg/nrglib/2004/immobilisation_of_iodine.pdfhttps://www.accessdata.fda.gov/drugsatfda_docs/label/2015/018057s083lbl.pdf
Curator's Comment:: description was created based on several sources, including
https://www.drugbank.ca/drugs/DB00515 | https://www.ncbi.nlm.nih.gov/pubmed/27736024 | https://www.ncbi.nlm.nih.gov/pubmed/25159039
Cisplatin is a chemotherapy medication used to treat a number of cancers. This includes testicular cancer, ovarian cancer, breast cancer, bladder cancer, head and neck cancer, cervical cancer, lung cancer, mesothelioma, esophageal cancer, brain tumors, and neuroblastoma. It is used by injection into a vein. Cisplatin is administered intravenously as a short-term infusion in normal saline for treatment of solid malignancies. Cisplatin interferes with DNA replication, which kills the fastest proliferating cells, which in theory are carcinogenic. Following administration, one of the two chloride ligands is slowly displaced by water to give the aquo complex cis-[PtCl(NH3)2(H2O)]+, in a process termed equation. Dissociation of the chloride ligand is favored inside the cell because the intracellular chloride concentration is only 3–20% of the approximately 100 mM chloride concentration in the extracellular fluid. The aqua ligand in cis-[PtCl(NH3)2(H2O)]+ is itself easily displaced by the N-heterocyclic bases on DNA. Guanine preferentially binds. Subsequent to the formation of [PtCl(guanine-DNA)(NH3)2]+, crosslinking can occur via displacement of the other chloride ligand, typically by another guanine. Cisplatin crosslinks DNA in several different ways, interfering with cell division by mitosis. The damaged DNA elicits DNA repair mechanisms, which in turn activate apoptosis when repair proves impossible. In 2008, researchers were able to show that the apoptosis induced by cisplatin in human colon cancer cells depends on the mitochondrial serine-protease Omi/Htra2. Cisplatin combination chemotherapy is the cornerstone of treatment of many cancers. Initial platinum responsiveness is high but the majority of cancer patients will eventually relapse with the cisplatin-resistant disease. Many mechanisms of cisplatin resistance have been proposed including changes in cellular uptake and efflux of the drug, increased detoxification of the drug, inhibition of apoptosis and increased DNA repair.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9865478
Curator's Comment:: With the injection of cisplatin into mice 3 h after the LPS treatment, platinum was detected in the CCR during the 7 days after the injection, while platinum was not detected in the CCR of cisplatin-injected mice without LPS pretreatment and of mice simultaneous treated with cisplatin and LPS.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL2311221 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27736024 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | CISPLATIN Approved UseCisplatin injection is indicated as therapy to be employed as follows: Metastatic Testicular Tumors In established combination therapy with other approved chemotherapeutic agents in patients with metastatic testicular tumors who have already received appropriate surgical and/or radiotherapeutic procedures. Metastatic Ovarian Tumors In established combination therapy with other approved chemotherapeutic agents in patients with metastatic ovarian tumors who have already received appropriate surgical and/or radiotherapeutic procedures. An established combination consists of Cisplatin injection and cyclophosphamide. Cisplatin injection, as a single agent, is indicated as secondary therapy in patients with metastatic ovarian tumors refractory to standard chemotherapy who have not previously received Cisplatin injection therapy. Advanced Bladder Cancer Cisplatin injection is indicated as a single agent for patients with transitional cell bladder cancer which is no longer amenable to local treatments, such as surgery and/or radiotherapy. Launch Date2.82873594E11 |
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Primary | CISPLATIN Approved UseCisplatin injection is indicated as therapy to be employed as follows: Metastatic Testicular Tumors In established combination therapy with other approved chemotherapeutic agents in patients with metastatic testicular tumors who have already received appropriate surgical and/or radiotherapeutic procedures. Metastatic Ovarian Tumors In established combination therapy with other approved chemotherapeutic agents in patients with metastatic ovarian tumors who have already received appropriate surgical and/or radiotherapeutic procedures. An established combination consists of Cisplatin injection and cyclophosphamide. Cisplatin injection, as a single agent, is indicated as secondary therapy in patients with metastatic ovarian tumors refractory to standard chemotherapy who have not previously received Cisplatin injection therapy. Advanced Bladder Cancer Cisplatin injection is indicated as a single agent for patients with transitional cell bladder cancer which is no longer amenable to local treatments, such as surgery and/or radiotherapy. Launch Date2.82873594E11 |
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Primary | CISPLATIN Approved UseCisplatin injection is indicated as therapy to be employed as follows: Metastatic Testicular Tumors In established combination therapy with other approved chemotherapeutic agents in patients with metastatic testicular tumors who have already received appropriate surgical and/or radiotherapeutic procedures. Metastatic Ovarian Tumors In established combination therapy with other approved chemotherapeutic agents in patients with metastatic ovarian tumors who have already received appropriate surgical and/or radiotherapeutic procedures. An established combination consists of Cisplatin injection and cyclophosphamide. Cisplatin injection, as a single agent, is indicated as secondary therapy in patients with metastatic ovarian tumors refractory to standard chemotherapy who have not previously received Cisplatin injection therapy. Advanced Bladder Cancer Cisplatin injection is indicated as a single agent for patients with transitional cell bladder cancer which is no longer amenable to local treatments, such as surgery and/or radiotherapy. Launch Date2.82873594E11 |
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Primary | CISPLATIN Approved UseCisplatin injection is indicated as therapy to be employed as follows: Metastatic Testicular Tumors In established combination therapy with other approved chemotherapeutic agents in patients with metastatic testicular tumors who have already received appropriate surgical and/or radiotherapeutic procedures. Metastatic Ovarian Tumors In established combination therapy with other approved chemotherapeutic agents in patients with metastatic ovarian tumors who have already received appropriate surgical and/or radiotherapeutic procedures. An established combination consists of Cisplatin injection and cyclophosphamide. Cisplatin injection, as a single agent, is indicated as secondary therapy in patients with metastatic ovarian tumors refractory to standard chemotherapy who have not previously received Cisplatin injection therapy. Advanced Bladder Cancer Cisplatin injection is indicated as a single agent for patients with transitional cell bladder cancer which is no longer amenable to local treatments, such as surgery and/or radiotherapy. Launch Date2.82873594E11 |
PubMed
Title | Date | PubMed |
---|---|---|
Platinum(II) chloride-catalyzed stereoselective domino enyne isomerization/Diels-Alder reaction. | 2010 Nov 19 |
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Platinum-catalyzed one-pot alkenylation of aldehydes using alkynes and triethylsilane: dual catalysis by platinum(II) chloride. | 2013 Nov 1 |
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Synthesis of tetracyclic chromenones via platinum(II) chloride catalysed cascade cyclization of enediyne-enones. | 2014 Feb 28 |
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Retrospective Analysis of the Risk Factors for Grade IV Neutropenia in Oesophageal Cancer Patients Treated with a Docetaxel, Cisplatin, and 5-Fluorouracil Regimen. | 2017 |
Patents
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C798
Created by
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WHO-ATC |
L01XA01
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admin on Fri Jun 25 20:55:30 UTC 2021 , Edited by admin on Fri Jun 25 20:55:30 UTC 2021
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FDA ORPHAN DRUG |
238607
Created by
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FDA ORPHAN DRUG |
221906
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WHO-VATC |
QL01XA01
Created by
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NDF-RT |
N0000175413
Created by
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FDA ORPHAN DRUG |
134800
Created by
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FDA ORPHAN DRUG |
536616
Created by
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FDA ORPHAN DRUG |
447514
Created by
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NDF-RT |
N0000175073
Created by
admin on Fri Jun 25 20:55:30 UTC 2021 , Edited by admin on Fri Jun 25 20:55:30 UTC 2021
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EU-Orphan Drug |
EU/3/13/1169
Created by
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LIVERTOX |
211
Created by
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FDA ORPHAN DRUG |
557716
Created by
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NCI_THESAURUS |
C1450
Created by
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FDA ORPHAN DRUG |
133200
Created by
admin on Fri Jun 25 20:55:30 UTC 2021 , Edited by admin on Fri Jun 25 20:55:30 UTC 2021
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Code System | Code | Type | Description | ||
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D002945
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1134357
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15663-27-1
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15663-27-1
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CHEMBL11359
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4392
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C376
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Q20Q21Q62J
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PRIMARY | |||
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84691
Created by
admin on Fri Jun 25 20:55:30 UTC 2021 , Edited by admin on Fri Jun 25 20:55:30 UTC 2021
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PRIMARY | |||
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Cisplatin
Created by
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3939
Created by
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239-733-8
Created by
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5343
Created by
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4426
Created by
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CISPLATIN
Created by
admin on Fri Jun 25 20:55:30 UTC 2021 , Edited by admin on Fri Jun 25 20:55:30 UTC 2021
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PRIMARY | Description: White to yellowish crystals or a yellow powder.Solubility: Slightly soluble in water; sparingly soluble in dimethylformamide R; practically insoluble in methanol R.Category: Cytotoxic drug.Storage: Cisplatin should be kept in a tightly closed container, protected from light, and stored at a temperature between 2 and 8?C.Additional information: CAUTION: Cisplatin must be handled with care, avoiding contact with the skin and inhalation of airborneparticles.When heated, it blackens at about 270 ?C with decomposition. | ||
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CISPLATIN
Created by
admin on Fri Jun 25 20:55:30 UTC 2021 , Edited by admin on Fri Jun 25 20:55:30 UTC 2021
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DB00515
Created by
admin on Fri Jun 25 20:55:30 UTC 2021 , Edited by admin on Fri Jun 25 20:55:30 UTC 2021
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M3586
Created by
admin on Fri Jun 25 20:55:30 UTC 2021 , Edited by admin on Fri Jun 25 20:55:30 UTC 2021
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PRIMARY | Merck Index | ||
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2555
Created by
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PRIMARY | RxNorm | ||
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SUB07483MIG
Created by
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PRIMARY |
ACTIVE MOIETY
METABOLITE ACTIVE (PRODRUG)
METABOLITE ACTIVE (PRODRUG)
PRODRUG (METABOLITE ACTIVE)