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Details

Stereochemistry ACHIRAL
Molecular Formula 2Cl.Pt.2H3N
Molecular Weight 300.051
Optical Activity NONE
Additional Stereochemistry Yes
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0
Stereo Comments SP-4-1 (TRANS)

SHOW SMILES / InChI
Structure of TRANSPLATIN

SMILES

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

InChI

InChIKey=LXZZYRPGZAFOLE-UHFFFAOYSA-L
InChI=1S/2ClH.2H3N.Pt/h2*1H;2*1H3;/q;;;;+2/p-2

HIDE SMILES / InChI

Molecular Formula Cl
Molecular Weight 35.453
Charge -1
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

Molecular Formula Pt
Molecular Weight 195.084
Charge 2
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.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

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: CHEMBL2311221
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
CISPLATIN

Approved Use

Cisplatin 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 Date

2.82873594E11
Primary
CISPLATIN

Approved Use

Cisplatin 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 Date

2.82873594E11
Primary
CISPLATIN

Approved Use

Cisplatin 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 Date

2.82873594E11
Primary
CISPLATIN

Approved Use

Cisplatin 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 Date

2.82873594E11
PubMed

PubMed

TitleDatePubMed
Platinum(II) chloride-catalyzed stereoselective domino enyne isomerization/Diels-Alder reaction.
2010 Nov 19
Platinum-catalyzed one-pot alkenylation of aldehydes using alkynes and triethylsilane: dual catalysis by platinum(II) chloride.
2013 Nov 1
Synthesis of tetracyclic chromenones via platinum(II) chloride catalysed cascade cyclization of enediyne-enones.
2014 Feb 28
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

Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Sun Dec 18 10:54:56 UTC 2022
Edited
by admin
on Sun Dec 18 10:54:56 UTC 2022
Record UNII
BW0OY6ZTD4
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TRANSPLATIN
Common Name English
TRANS-DIAMINEDICHLOROPLATINUM
Common Name English
TRANS-DDP
Common Name English
TRANS-DICHLORODIAMMINEPLATINUM(II)
Systematic Name English
(SP-4-1)-DIAMMINEDICHLOROPLATINUM
Systematic Name English
TRANSPLATIN [USP-RS]
Common Name English
PLATINUM, DIAMMINEDICHLORO-, (SP-4-1)-
Systematic Name English
TRANS-DICHLORODIAMINEPLATINUM(II)
Systematic Name English
TRANS-PLATINUMDIAMMINE DICHLORIDE
Systematic Name English
NSC-131558
Code English
TRANS-PLATINUM(II) AMMONIUM CHLORIDE
Systematic Name English
TRANS-DIAMMINEDICHLOROPLATINUM(II)
Common Name English
TRANS-DICHLORODIAMMINE PLATINUM
Systematic Name English
TRANS-DIAMMINEDICHLOROPLATINUM
Common Name English
Code System Code Type Description
PUBCHEM
84691
Created by admin on Sun Dec 18 10:54:56 UTC 2022 , Edited by admin on Sun Dec 18 10:54:56 UTC 2022
PRIMARY
CAS
14913-33-8
Created by admin on Sun Dec 18 10:54:56 UTC 2022 , Edited by admin on Sun Dec 18 10:54:56 UTC 2022
PRIMARY
NSC
131558
Created by admin on Sun Dec 18 10:54:56 UTC 2022 , Edited by admin on Sun Dec 18 10:54:56 UTC 2022
PRIMARY
HSDB
3940
Created by admin on Sun Dec 18 10:54:56 UTC 2022 , Edited by admin on Sun Dec 18 10:54:56 UTC 2022
PRIMARY
FDA UNII
BW0OY6ZTD4
Created by admin on Sun Dec 18 10:54:56 UTC 2022 , Edited by admin on Sun Dec 18 10:54:56 UTC 2022
PRIMARY
CHEBI
35852
Created by admin on Sun Dec 18 10:54:56 UTC 2022 , Edited by admin on Sun Dec 18 10:54:56 UTC 2022
PRIMARY
EPA CompTox
DTXSID101016811
Created by admin on Sun Dec 18 10:54:56 UTC 2022 , Edited by admin on Sun Dec 18 10:54:56 UTC 2022
PRIMARY
RS_ITEM_NUM
1672803
Created by admin on Sun Dec 18 10:54:56 UTC 2022 , Edited by admin on Sun Dec 18 10:54:56 UTC 2022
PRIMARY
WIKIPEDIA
Transplatin
Created by admin on Sun Dec 18 10:54:56 UTC 2022 , Edited by admin on Sun Dec 18 10:54:56 UTC 2022
PRIMARY
ECHA (EC/EINECS)
238-980-9
Created by admin on Sun Dec 18 10:54:56 UTC 2022 , Edited by admin on Sun Dec 18 10:54:56 UTC 2022
PRIMARY
Related Record Type Details
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