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{{drugbox
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| IUPAC_name = cis-diamminedichloroplatinum(II)  
|authorTag=
| image = Cisplatin-2D.png
 
| width = 134
{{VP}}
| image2 = Cisplatin-3D-vdW.png
<!--Overview-->
| CAS_number = 15663-27-1
 
| ATC_prefix = L01
|genericName=
| ATC_suffix = XA01
 
| ATC_supplemental =  
 
| PubChem = 84691
 
| DrugBank = APRD00359
|aOrAn=
| Cl=2 | H=6 | N=2 | Pt=1
 
| molecular_weight = 300.05 g/mol
a
| bioavailability = complete
 
| protein_bound = > 90%
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| elimination_half-life = 30-100 hours
 
| pregnancy_US = D
 
| legal_status =  
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| routes_of_administration = Intravenous
 
| excretion = Renal
 
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==Overview==
There is limited information regarding <i>Patient Counseling Information</i> of {{PAGENAME}} in the drug label.
'''Cisplatin''', '''cisplatinum''' or '''cis-diamminedichloroplatinum(II) (CDDP)''' is a [[platinum]]-based [[chemotherapy]] [[medication|drug]] used to treat various types of cancers, including [[sarcoma]]s, some [[carcinoma]]s (e.g. [[lung cancer|small cell lung cancer]], and [[ovarian cancer]]), [[lymphoma]]s and germ cell tumors. It was the first member of its class, which now also includes [[carboplatin]] and [[oxaliplatin]].


==Pharmacology==
<!--Precautions with Alcohol-->
Upon administration, a chloride ligand undergo slow displacement with water (an aqua ligand)  molecules, in a process termed aquation. The  aqua ligand in the resulting [PtCl(H<sub>2</sub>O)(NH<sub>3</sub>)<sub>2</sub>]<sup>+</sup> is easily displaced, allowing cisplatin to coordinate a basic site in [[DNA]]. Subsequently, the platinum cross-links two bases via displacement of the other chloride ligand.<ref name = trzaska/> 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.


Most notable among the DNA changes are the 1,2-intrastrand cross-links with [[purine]] bases.  These include 1,2-intrastrand d([[guanine|G]]pG) adducts which form nearly 90% of the adducts and the less common 1,2-intrastrand d([[adenosine|A]]pG) adducts.  1,3-intrastrand d(GpXpG) adducts occur but are readily excised by the [[nucleotide]] excision repair ([[nucleotide excision repair|NER]]) .  Other adducts include inter-strand crosslinks and nonfunctional adducts that have been postulated to contribute to cisplatin's activity. Interaction with cellular proteins, particularly [[high mobility group|HMG]] domain proteins, has also been advanced as a mechanism of interfering with mitosis, although this is probably not its primary method of action.
|alcohol=


===''trans''-PtCl<sub>2</sub>(NH<sub>3</sub>)<sub>2</sub>===
* Alcohol-{{PAGENAME}} interaction has not been established. Talk to your doctor about the effects of taking alcohol with this medication.
The [[trans isomer|trans]]-[PtCl<sub>2</sub>(H<sub>2</sub>O)(NH<sub>3</sub>)<sub>2</sub> does not exhibit a comparably useful pharmacological effect.  Its low activity is generally thought to be due to rapid deactivation of the drug before it can arrive at the DNA. It is toxic, and it is desirable to test batches of ''cis''-platin for the absence of the trans isomer.  In a procedure by Woollins et al., which is based on the classic 'Kurnakov test', [[thiourea]] reacts with the sample to give derivatives are easily separated and detected by HPLC.<ref>{{cite journal | author = J. D. Woollins, A. Woollins and B. Rosenberg | title = The detection of trace amounts of trans-Pt(NH3)2Cl2 in the presence of cis-Pt(NH3)<sub>2</sub>Cl<sub>2</sub>. A high performance liquid chromatographic application of kurnakow's test | year = 1983 | journal = [[Polyhedron]] | volume = 2 | issue = 3 | pages = 175-178 | doi = 10.1016/S0277-5387(00)83954-6}}</ref><!--if this result were truly useful/notable, it would not be published in this  journal-->


== Side effects==
<!--Brand Names-->
Cisplatin has a number of side-effects that can limit its use:
* [[Nephrotoxicity]] (kidney damage) is a major concern when cisplatin is given. The dose is reduced when the patient's [[creatinine clearance]] (a measure of [[renal function]]) is reduced. Adequate hydration and [[diuretic|diuresis]] is used to prevent renal damage. The nephrotoxicity of platinum-class drugs seems to be related to [[reactive oxygen species]] and in animal models can be ameliorated by [[free radical]] scavenging agents. This is a dose-limiting toxicity.
* [[Neurotoxicity]] (nerve damage) can be anticipated by performing [[nerve conduction studies]] before and after treatment.
* [[Nausea]] and [[vomiting]].  Cisplatin is one of the most emetogenic chemotherapy agents, but this is managed with prophylactic antiemetics (e.g. [[ondansetron]], [[granisetron]], etc.) in combination with [[corticosteroids]]. [[Aprepitant]] combined with [[ondansetron]] and [[dexamethasone]] has been shown to be better for highly emetogenic chemotherapy than just [[ondansetron]] and [[dexamethasone]].
* [[Ototoxicity]] (hearing loss): unfortunately there is at present no effective treatment to prevent this side effect, which may be severe.  Audiometric analysis may be necessary to assess the severity of ototoxicity.  Other drugs (such as the aminoglycoside antibiotic class) may also cause ototoxicity, and the administration of this class of antibiotics in patients receiving cisplatin is generally avoided.  The ototoxicity of both the aminoglycosides and cisplatin may be related to their ability to bind to [[melanin]] in the [[stria vascularis]] of the inner ear or the generation of [[reactive oxygen species]].
* [[Alopecia]] (hair loss): this is generally not a major problem in patients treated with cisplatin.
* [[Electrolyte disturbance]]: Cisplatin can cause hypomagnesaemia, hypokalaemia and hypocalcaemia. The hypocalcaemia seems to occur in those with low serum magnesium secondary to cisplatin, so it is not primarily due to the Cisplatin.


==History==
|brandNames=
The compound ''cis''-PtCl<sub>2</sub>(NH<sub>3</sub>)<sub>2</sub> was first described by M. Peyrone in 1845 (known as Peyrone's salt).<ref>Peyrone M. Ann Chemie Pharm '''1845''';51:129.</ref> The structure was deduced by Alfred Werner in 1893.<ref name = trzaska>{{cite journal | url = http://pubs.acs.org/cen/coverstory/83/8325/8325cisplatin.html | title = Cisplatin | author = Stephen Trzaska | journal= [[C&EN News]] | volume = 83 | issue = 25 | date = 20 Jun 05}}</ref> In the 1960s, [[Barnett Rosenberg]] and van Camp ''et al'' at Michigan State University discovered that [[electrolysis]] of a platinum electrode produced cisplatin, which inhibited binary fission in ''[[Escherichia coli]]'' (''E. coli'') bacteria. The bacteria grow to 300 times their normal length but cell division fails. Rosenberg then conducted a series of experiments to test the effects various [[platinum]] coordination complexes on [[sarcoma]]s artificially implanted in rats. This study found that cis-diamminedichloroplatinum(II) was the most effective out of this group, which started the medicinal career of cisplatin.<ref>{{cite journal
| author = Rosenberg, B. | coauthors = Van Camp, L.; Krigas, T. | year = 1965 | title = Inhibition of cell division in Escherichia coli by electrolysis products from a platinum electrode | journal = [[Nature (journal)|Nature]] | volume = 205 | issue = 4972 | pages = 698-699 | doi = 10.1038/205698a0}}</ref>


Approved for clinical use by the United States [[Food and Drug Administration]] (FDA) in 1978, it revolutionized the treatment of certain cancers. Detailed studies on its molecular [[mechanism of action]], using a variety of spectrocopic methods including X-ray, NMR spectroscopy, and other physico-chemical methods, revealed its ability to form irreversible crosslinks with bases in DNA.
* ®<ref>{{Cite web | title =  | url =  }}</ref>


==Synthesis==
<!--Look-Alike Drug Names-->
[[Image:Cisplatinsynthesis.jpg|500px|left|Synthesis of cisplatin]]


The synthesis of cisplatin is a classic in [[inorganic chemistry]]. Starting from [[potassium tetrachloroplatinate]], K<sub>2</sub>PtCl<sub>4</sub><sup>2−</sup>, the first NH<sub>3</sub> ligand is added to any of the four equivalent positions, but the second NH<sub>3</sub> could be added [[cis]] or [[trans]] to the amine [[ligand]]. Because Cl<sup>−</sup> has a larger [[trans effect]] than NH<sub>3</sub>, the second amine substitutes trans to a chloride ligand, and therefore cis to the first amine. The trans effect of the halides follows the order I<sup>-</sup>>Br<sup>-</sup>>Cl<sup>-</sup>, therefore the synthesis is conducted using PtI<sub>4</sub><sup>2−</sup> to ensure high yield and purity of the cis isomer, followed by conversion of the PtI<sub>2</sub></sup>(NH<sub>3</sub>)<sub>2</sub> into PtCl<sub>2</sub></sup>(NH<sub>3</sub>)<sub>2</sub>, as first described by Dhara.<ref>Dhara, S. C. Indian Journal of Chemistry 1970, volume 8, pp. 193–134.</ref><ref name = alderden>{{cite journal | title = The Discovery and Development of Cisplatin | author = Rebecca A. Alderden, Matthew D. Hall, and Trevor W. Hambley | year = 2006 | volume = 83 | pages = 728-724 | url = http://jchemed.chem.wisc.edu/journal/issues/2006/May/abs728.html | journal = [[J. Chem. Ed.]]}}</ref>
|lookAlike=


* A® — B®<ref name="www.ismp.org">{{Cite web  | last =  | first =  | title = http://www.ismp.org | url = http://www.ismp.org | publisher =  | date =  }}</ref>


<!--Drug Shortage Status-->


|drugShortage=
}}


==References==
<!--Pill Image-->
<references/>


==External links==
{{PillImage
* [http://chemcases.com/cisplat/index.htm Cisplatin: The Invention of an Anticancer Drug] by Andri Smith
|fileName=No image.jpg|This image is provided by the National Library of Medicine.
* [http://www2.mrc-lmb.cam.ac.uk/personal/sl/Html/Frames.html Cisplatin and its Analogues (excellent detailed overview)
|drugName=
* [http://www.nlm.nih.gov/medlineplus/druginfo/medmaster/a684036.html MedlinePlus page on cisplatin]
|NDC=
* [http://www-cie.iarc.fr/htdocs/monographs/suppl7/cisplatin.html IARC Monograph: "Cisplatin"]
|drugAuthor=
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{{Chemotherapeutic agents}}
<!--Label Display Image-->


[[Category:Platinum compounds]]
{{LabelImage
[[Category:Chemotherapeutic agents]]
|fileName={{PAGENAME}}11.png|This image is provided by the National Library of Medicine.
[[Category:IARC Group 2A carcinogens]]
}}
[[Category:Coordination compounds]]
 
{{LabelImage
|fileName={{PAGENAME}}11.png|This image is provided by the National Library of Medicine.
}}


[[de:Cisplatin]]
<!--Category-->
[[fr:Cisplatine]]
[[nl:Cisplatine]]
[[ja:シスプラチン]]
[[pl:Cisplatyna]]
[[pt:Cisplatina (química)]]
[[ru:Цисплатин]]
[[tr:Sisplatin]]
{{WH}}
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Revision as of 19:51, 23 December 2014

Cisplatin
Black Box Warning
Adult Indications & Dosage
Pediatric Indications & Dosage
Contraindications
Warnings & Precautions
Adverse Reactions
Drug Interactions
Use in Specific Populations
Administration & Monitoring
Overdosage
Pharmacology
Clinical Studies
How Supplied
Images
Patient Counseling Information
Precautions with Alcohol
Brand Names
Look-Alike Names

Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]; Associate Editor(s)-in-Chief: Vignesh Ponnusamy, M.B.B.S. [2]

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Black Box Warning

Title
See full prescribing information for complete Boxed Warning.
ConditionName:
  • Content

Overview

Cisplatin is a that is FDA approved for the {{{indicationType}}} of . There is a Black Box Warning for this drug as shown here. Common adverse reactions include .

Adult Indications and Dosage

FDA-Labeled Indications and Dosage (Adult)

Condition1
  • Dosing Information
  • Dosage
Condition2
  • Dosing Information
  • Dosage
Condition3
  • Dosing Information
  • Dosage
Condition4
  • Dosing Information
  • Dosage

Off-Label Use and Dosage (Adult)

Guideline-Supported Use

Condition1
  • Developed by:
  • Class of Recommendation:
  • Strength of Evidence:
  • Dosing Information
  • Dosage
Condition2

There is limited information regarding Off-Label Guideline-Supported Use of Cisplatin in adult patients.

Non–Guideline-Supported Use

Condition1
  • Dosing Information
  • Dosage
Condition2

There is limited information regarding Off-Label Non–Guideline-Supported Use of Cisplatin in adult patients.

Pediatric Indications and Dosage

FDA-Labeled Indications and Dosage (Pediatric)

Condition1
  • Dosing Information
  • Dosage
Condition2

There is limited information regarding FDA-Labeled Use of Cisplatin in pediatric patients.

Off-Label Use and Dosage (Pediatric)

Guideline-Supported Use

Condition1
  • Developed by:
  • Class of Recommendation:
  • Strength of Evidence:
  • Dosing Information
  • Dosage
Condition2

There is limited information regarding Off-Label Guideline-Supported Use of Cisplatin in pediatric patients.

Non–Guideline-Supported Use

Condition1
  • Dosing Information
  • Dosage
Condition2

There is limited information regarding Off-Label Non–Guideline-Supported Use of Cisplatin in pediatric patients.

Contraindications

  • Condition1

Warnings

Title
See full prescribing information for complete Boxed Warning.
ConditionName:
  • Content
  • Description

Precautions

  • Description

Adverse Reactions

Clinical Trials Experience

There is limited information regarding Clinical Trial Experience of Cisplatin in the drug label.

Body as a Whole
Cardiovascular
Digestive
Endocrine
Hematologic and Lymphatic
Metabolic and Nutritional
Musculoskeletal
Neurologic
Respiratory
Skin and Hypersensitivy Reactions
Special Senses
Urogenital
Miscellaneous

Postmarketing Experience

There is limited information regarding Postmarketing Experience of Cisplatin in the drug label.

Body as a Whole
Cardiovascular
Digestive
Endocrine
Hematologic and Lymphatic
Metabolic and Nutritional
Musculoskeletal
Neurologic
Respiratory
Skin and Hypersensitivy Reactions
Special Senses
Urogenital
Miscellaneous

Drug Interactions

  • Drug
  • Description

Use in Specific Populations

Pregnancy

Pregnancy Category (FDA):

  • Pregnancy Category


Pregnancy Category (AUS):

  • Australian Drug Evaluation Committee (ADEC) Pregnancy Category

There is no Australian Drug Evaluation Committee (ADEC) guidance on usage of Cisplatin in women who are pregnant.

Labor and Delivery

There is no FDA guidance on use of Cisplatin during labor and delivery.

Nursing Mothers

There is no FDA guidance on the use of Cisplatin with respect to nursing mothers.

Pediatric Use

There is no FDA guidance on the use of Cisplatin with respect to pediatric patients.

Geriatic Use

There is no FDA guidance on the use of Cisplatin with respect to geriatric patients.

Gender

There is no FDA guidance on the use of Cisplatin with respect to specific gender populations.

Race

There is no FDA guidance on the use of Cisplatin with respect to specific racial populations.

Renal Impairment

There is no FDA guidance on the use of Cisplatin in patients with renal impairment.

Hepatic Impairment

There is no FDA guidance on the use of Cisplatin in patients with hepatic impairment.

Females of Reproductive Potential and Males

There is no FDA guidance on the use of Cisplatin in women of reproductive potentials and males.

Immunocompromised Patients

There is no FDA guidance one the use of Cisplatin in patients who are immunocompromised.

Administration and Monitoring

Administration

  • Oral
  • Intravenous

Monitoring

There is limited information regarding Monitoring of Cisplatin in the drug label.

  • Description

IV Compatibility

There is limited information regarding IV Compatibility of Cisplatin in the drug label.

Overdosage

Acute Overdose

Signs and Symptoms

  • Description

Management

  • Description

Chronic Overdose

There is limited information regarding Chronic Overdose of Cisplatin in the drug label.

Pharmacology

There is limited information regarding Cisplatin Pharmacology in the drug label.

Mechanism of Action

Structure

This image is provided by the National Library of Medicine.

Pharmacodynamics

There is limited information regarding Pharmacodynamics of Cisplatin in the drug label.

Pharmacokinetics

There is limited information regarding Pharmacokinetics of Cisplatin in the drug label.

Nonclinical Toxicology

There is limited information regarding Nonclinical Toxicology of Cisplatin in the drug label.

Clinical Studies

There is limited information regarding Clinical Studies of Cisplatin in the drug label.

How Supplied

Storage

There is limited information regarding Cisplatin Storage in the drug label.

Images

Drug Images

{{#ask: Page Name::Cisplatin |?Pill Name |?Drug Name |?Pill Ingred |?Pill Imprint |?Pill Dosage |?Pill Color |?Pill Shape |?Pill Size (mm) |?Pill Scoring |?NDC |?Drug Author |format=template |template=DrugPageImages |mainlabel=- |sort=Pill Name }}

Package and Label Display Panel

{{#ask: Label Page::Cisplatin |?Label Name |format=template |template=DrugLabelImages |mainlabel=- |sort=Label Page }}

Patient Counseling Information

There is limited information regarding Patient Counseling Information of Cisplatin in the drug label.

Precautions with Alcohol

  • Alcohol-Cisplatin interaction has not been established. Talk to your doctor about the effects of taking alcohol with this medication.

Brand Names

Look-Alike Drug Names

Drug Shortage Status

Price

References

The contents of this FDA label are provided by the National Library of Medicine.

  1. ↑ Empty citation (help)
  2. ↑ "http://www.ismp.org". External link in |title= (help)


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