U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of CISPLATIN

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

HIDE SMILES / InChI

Description
Curator's Comment:: 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

TargetsConditions

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

282873600000
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

282873600000
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

282873600000
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

282873600000
PubMed

PubMed

TitleDatePubMed
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

Name Type Language
CISPLATIN
EP   HSDB   INN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD   WHO-IP  
USAN   INN  
Official Name English
CIS-DIAMMINEDICHLOROPLATINUM II
Common Name English
CISPLATIN [USAN]
Common Name English
CISPLATIN [USP-RS]
Common Name English
CISPLATIN [INN]
Common Name English
CIS-DIAMMINEDICHLOROPLATINUM [WHO-IP]
Common Name English
PEYRONE'S SALT
Common Name English
FAULDISCIPLA
Common Name English
CISPLATIN [MART.]
Common Name English
CISPLATINUM
WHO-IP LATIN  
Common Name English
PLATINOL
Brand Name English
CIS-DDP
Code English
NSC-119875
Code English
CISPLATIN [IARC]
Common Name English
CISPLATIN [EP MONOGRAPH]
Common Name English
(SP-4-2)-DIAMMINEDICHLOROPLATINUM [WHO-IP]
Common Name English
CIS-DIAMMINEDICHLOROPLATINUM
WHO-IP  
Common Name English
CISPLATIN [WHO-DD]
Common Name English
INT-230-6 COMPONENT CISPLATIN
Code English
INT230-6 COMPONENT CISPLATIN
Code English
LIPLACIS
Brand Name English
CISPLATIN [WHO-IP]
Common Name English
CISPLATIN [ORANGE BOOK]
Common Name English
CISPLATIN [USP MONOGRAPH]
Common Name English
CIS-PLATIN
Common Name English
CDDP
Common Name English
CISPLATIN [JAN]
Common Name English
CISPLATINUM [WHO-IP LATIN]
Common Name English
CISPLATIN [HSDB]
Common Name English
CISPLATIN [MI]
Common Name English
CISPLATIN [EP]
Common Name English
PLATINUM, DIAMMINEDICHLORO-, (SP-4-2)-
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C798
Created by admin on Fri Jun 25 20:55:30 UTC 2021 , Edited by admin on Fri Jun 25 20:55:30 UTC 2021
WHO-ATC L01XA01
Created by admin on Fri Jun 25 20:55:30 UTC 2021 , Edited by admin on Fri Jun 25 20:55:30 UTC 2021
FDA ORPHAN DRUG 238607
Created by admin on Fri Jun 25 20:55:30 UTC 2021 , Edited by admin on Fri Jun 25 20:55:30 UTC 2021
FDA ORPHAN DRUG 221906
Created by admin on Fri Jun 25 20:55:30 UTC 2021 , Edited by admin on Fri Jun 25 20:55:30 UTC 2021
WHO-VATC QL01XA01
Created by admin on Fri Jun 25 20:55:30 UTC 2021 , Edited by admin on Fri Jun 25 20:55:30 UTC 2021
NDF-RT N0000175413
Created by admin on Fri Jun 25 20:55:30 UTC 2021 , Edited by admin on Fri Jun 25 20:55:30 UTC 2021
FDA ORPHAN DRUG 134800
Created by admin on Fri Jun 25 20:55:30 UTC 2021 , Edited by admin on Fri Jun 25 20:55:30 UTC 2021
FDA ORPHAN DRUG 536616
Created by admin on Fri Jun 25 20:55:30 UTC 2021 , Edited by admin on Fri Jun 25 20:55:30 UTC 2021
FDA ORPHAN DRUG 447514
Created by admin on Fri Jun 25 20:55:30 UTC 2021 , Edited by admin on Fri Jun 25 20:55:30 UTC 2021
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
EU-Orphan Drug EU/3/13/1169
Created by admin on Fri Jun 25 20:55:30 UTC 2021 , Edited by admin on Fri Jun 25 20:55:30 UTC 2021
LIVERTOX 211
Created by admin on Fri Jun 25 20:55:30 UTC 2021 , Edited by admin on Fri Jun 25 20:55:30 UTC 2021
FDA ORPHAN DRUG 557716
Created by admin on Fri Jun 25 20:55:30 UTC 2021 , Edited by admin on Fri Jun 25 20:55:30 UTC 2021
NCI_THESAURUS C1450
Created by admin on Fri Jun 25 20:55:30 UTC 2021 , Edited by admin on Fri Jun 25 20:55:30 UTC 2021
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
Code System Code Type Description
MESH
D002945
Created by admin on Fri Jun 25 20:55:30 UTC 2021 , Edited by admin on Fri Jun 25 20:55:30 UTC 2021
PRIMARY
USP_CATALOG
1134357
Created by admin on Fri Jun 25 20:55:30 UTC 2021 , Edited by admin on Fri Jun 25 20:55:30 UTC 2021
PRIMARY USP-RS
EPA CompTox
15663-27-1
Created by admin on Fri Jun 25 20:55:30 UTC 2021 , Edited by admin on Fri Jun 25 20:55:30 UTC 2021
PRIMARY
CAS
15663-27-1
Created by admin on Fri Jun 25 20:55:30 UTC 2021 , Edited by admin on Fri Jun 25 20:55:30 UTC 2021
PRIMARY
ChEMBL
CHEMBL11359
Created by admin on Fri Jun 25 20:55:30 UTC 2021 , Edited by admin on Fri Jun 25 20:55:30 UTC 2021
PRIMARY
DRUG CENTRAL
4392
Created by admin on Fri Jun 25 20:55:30 UTC 2021 , Edited by admin on Fri Jun 25 20:55:30 UTC 2021
PRIMARY
NCI_THESAURUS
C376
Created by admin on Fri Jun 25 20:55:30 UTC 2021 , Edited by admin on Fri Jun 25 20:55:30 UTC 2021
PRIMARY
FDA UNII
Q20Q21Q62J
Created by admin on Fri Jun 25 20:55:30 UTC 2021 , Edited by admin on Fri Jun 25 20:55:30 UTC 2021
PRIMARY
PUBCHEM
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
PRIMARY
LACTMED
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
PRIMARY
HSDB
3939
Created by admin on Fri Jun 25 20:55:30 UTC 2021 , Edited by admin on Fri Jun 25 20:55:30 UTC 2021
PRIMARY
ECHA (EC/EINECS)
239-733-8
Created by admin on Fri Jun 25 20:55:30 UTC 2021 , Edited by admin on Fri Jun 25 20:55:30 UTC 2021
PRIMARY
IUPHAR
5343
Created by admin on Fri Jun 25 20:55:30 UTC 2021 , Edited by admin on Fri Jun 25 20:55:30 UTC 2021
PRIMARY
INN
4426
Created by admin on Fri Jun 25 20:55:30 UTC 2021 , Edited by admin on Fri Jun 25 20:55:30 UTC 2021
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
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
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.
WIKIPEDIA
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
PRIMARY
DRUG BANK
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
PRIMARY
MERCK INDEX
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
PRIMARY Merck Index
RXCUI
2555
Created by admin on Fri Jun 25 20:55:30 UTC 2021 , Edited by admin on Fri Jun 25 20:55:30 UTC 2021
PRIMARY RxNorm
EVMPD
SUB07483MIG
Created by admin on Fri Jun 25 20:55:30 UTC 2021 , Edited by admin on Fri Jun 25 20:55:30 UTC 2021
PRIMARY