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 | | Cisplatin | | Systematic (IUPAC) name | | cis-diamminedichloroplatinum(II) | | Identifiers | | CAS number | 15663-27-1 | | ATC code | L01XA01 | | PubChem | 84691 | | DrugBank | APRD00359 | | Chemical data | | Formula | ? | | Mol. mass | 300.05 g/mol | | Pharmacokinetic data | | Bioavailability | complete | | Protein binding | > 90% | | Metabolism | ? | | Half life | 30-100 hours | | Excretion | Renal | | Therapeutic considerations | | Pregnancy cat. | D(US) Image File history File links Download high-resolution version (1100x623, 32 KB) File links The following pages on the English Wikipedia link to this file (pages on other projects are not listed): Cisplatin ...
Image File history File links Download high-resolution version (1100x949, 269 KB) File links The following pages on the English Wikipedia link to this file (pages on other projects are not listed): Cisplatin ...
IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ...
CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ...
The Anatomical Therapeutic Chemical Classification System is used for the classification of drugs. ...
A section of the Anatomical Therapeutic Chemical Classification System. ...
PubChem is a database of chemical molecules. ...
The DrugBank database available at the University of Alberta is a unique bioinformatics and cheminformatics resource that combines detailed drug (i. ...
This article or section does not cite any references or sources. ...
The molecular mass (abbreviated Mr) of a substance, formerly also called molecular weight and abbreviated as MW, is the mass of one molecule of that substance, relative to the unified atomic mass unit u (equal to 1/12 the mass of one atom of carbon-12). ...
In pharmacology, bioavailability is used to describe the fraction of an administered dose of unchanged drug that reaches the systemic circulation, one of the principal pharmacokinetic properties of drugs. ...
A drugs efficacy may be affected by the degree to which it binds to the proteins within blood plasma. ...
Drug metabolism is the metabolism of drugs, their biochemical modification or degradation, usually through specialized enzymatic systems. ...
It has been suggested that Effective half-life be merged into this article or section. ...
Excretion is the process of eliminating waste products of metabolism and other materials that are of no use. ...
The pregnancy category of a pharmaceutical agent is an assessment of the risk of fetal injury due to the pharmaceutical, if it is used as directed by the mother during pregnancy. ...
Motto: (Out Of Many, One) (traditional) In God We Trust (1956 to date) Anthem: The Star-Spangled Banner Capital Washington D.C. Largest city New York City None at federal level (English de facto) Government Federal constitutional republic - President George Walker Bush (R) - Vice President Dick Cheney (R) Independence from...
| | Legal status | | | Routes | Intravenous | Cisplatin, cisplatinum or cis-diamminedichloroplatinum(II) (CDDP) is a platinum-based chemotherapy drug used to treat various types of cancers, including sarcomas, some carcinomas (e.g. small cell lung cancer and ovarian cancer), lymphomas and germ cell tumors. It was the first member of its class, which now also includes carboplatin and oxaliplatin. The regulation of therapeutic goods, that is drugs and therapeutic devices, varies by jurisdiction. ...
In pharmacology and toxicology, a route of administration is the path by which a drug, fluid, poison or other substance is brought into contact with the body 1. ...
General Name, Symbol, Number platinum, Pt, 78 Chemical series transition metals Group, Period, Block 10, 6, d Appearance grayish white Standard atomic weight 195. ...
Chemotherapy is the use of chemical substances to treat disease. ...
This article does not cite any references or sources. ...
A sarcoma is a cancer of the connective or supportive tissue (bone, cartilage, fat, muscle, blood vessels) and soft tissue. ...
In medicine, carcinoma is any cancer that arises from epithelial cells. ...
Lung cancer is the malignant transformation and expansion of lung tissue, and is the most lethal of all cancers worldwide, responsible for 1. ...
Ovarian cancer is a malignant tumor (a kind of neoplasm) located on an ovary. ...
This article is about lymphoma in humans. ...
Carboplatin is a chemotherapy drug used against some forms of cancer. ...
Oxaliplatin is a platinum-based chemotherapy drug in the same family as cisplatin and carboplatin. ...
Synthesis
The synthesis of cisplatin is a classic in inorganic chemistry. Starting from tetrachloroplatinate, PtCl42−, the first NH3 ligand is added to any of the four equivalent positions, but the second NH3 could be added cis or trans to the amine ligand. Because Cl− has a larger trans effect than NH3, the second amine substitutes trans to the chloride ligand, and therefore cis to the first amine. The trans effect of the halides follows the order I->Br->Cl-, therefore the synthesis is conducted using PtI42− to ensure high yield and purity of the cis isomer, followed by conversion of the PtI2(NH3)2 into PtCl2(NH3)2, as first described by Dhara.[citation needed]
 Inorganic chemistry is the branch of chemistry concerned with the properties and reactions of inorganic compounds. ...
CIS usually refers to: Commonwealth of Independent States, a modern-day political entity consisting of 11 former Soviet Union Republics CIS is also an acronym for: Canadian Interuniversity Sport Cancer Information Service Carcinoma in situ Centre for Independent Studies Center for Immigration Studies Chinese International School Cisalpino Citizenship & Immigration Services...
Trans is a Latin noun or prefix, meaning across, beyond or on the opposite side [of] . It is the opposite of cis, which means on the same side [of]. In chemistry, a double bond (or ring) not subject to free rotation in which the greater radical on both ends is...
In chemistry, a ligand is an atom, ion, or molecule (see also: functional group) that generally donates one or more of its electrons through a coordinate covalent bond to, or shares its electrons through a covalent bond with, one or more central atoms or ions (these ligands act as a...
In inorganic chemistry, the trans effect is the labilization of ligands trans to certain other ligands, which can thus be regarded as trans directing ligands. ...
Image File history File links Download high-resolution version (1800x930, 107 KB) Synthetic scheme for the synthesis of the anti-cancer drug cisplatin, cis-diamminedichloroplatinum(II), based on the commonly used method reported by Dhara in 1969. ...
Pharmacology
Mechanism of action Upon administration, a chlorine ligand can undergo slow displacement with water (an aqua ligand) molecules, in a process termed aquation. The aqua ligand is highly reactive, allowing cisplatin to coordinate a base in DNA, and a subsequent cross-link is formed after loss of the second chlorine ligand. Cisplatin acts by crosslinking DNA in several different ways, making it impossible for rapidly dividing cells to duplicate their DNA for mitosis. The damaged DNA sets off DNA repair mechanisms, which activate apoptosis when repair proves impossible. The trans isomer does not have this pharmacological effect, though this is generally thought to be due to rapid deactivation of the drug before it can arrive at the DNA. The structure of part of a DNA double helix Deoxyribonucleic acid, or DNA, is a nucleic acid molecule that contains the genetic instructions used in the development and functioning of all known living organisms. ...
Mitosis is the process in which a cell duplicates its chromosomes to generate two identical cells. ...
DNA damage resulting in multiple broken chromosomes DNA repair refers to a collection of processes by which a cell identifies and corrects damage to the DNA molecules that encode its genome. ...
A section of mouse liver showing an apoptotic cell indicated by an arrow // Apoptosis is a process of deliberate life relinquishment by a cell in a multicellular organism. ...
In chemistry, geometric isomerism is a form of stereoisomerism and describes the orientation of functional groups at the ends of a bond around which no rotation is possible. ...
The cis isomer is cytotoxic to the tumor cells whereas the trans isomer does not have an anticancer effect, it is toxic, therefore it is normal to test batches of cis-platin by HPLC for the absence of the trans isomer. This test, based on the classic 'Kurnakov test', uses thiourea as a ligand; cis compounds turn yellow, trans compounds give a white precipitate.[1] Chromatography is a family of analytical chemistry techniques for the separation of mixtures. ...
Most notable among the DNA changes are the 1,2-intrastrand cross-links with purine bases. These include 1,2-intrastrand d(GpG) adducts which form nearly 90% of the adducts and the less common 1,2-intrastrand d(ApG) adducts. 1,3-intrastrand d(GpXpG) adducts occur but are readily excised by the 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 HMG domain proteins, has also been advanced as a mechanism of interfering with mitosis, although this is probably not its primary method of action. Purine is a heterocyclic aromatic organic compound, consisting of a pyrimidine ring fused to an imidazole ring. ...
Guanine is one of the five main nucleobases found in the nucleic acids DNA and RNA; the others being adenine, cytosine, thymine, and uracil. ...
Adenosine is a nucleoside comprised of adenine attached to a ribose (ribofuranose) moiety via a β-N9-glycosidic bond. ...
A nucleotide is a chemical compound that consists of a heterocyclic base, a sugar, and one or more phosphate groups. ...
// Nucleotide Excision Repair DNA constantly requires repair due to chemical damage that can occur to bases, and nucleotide excision repair (NER) is one of the mechanisms by which the cell can prevent unwanted mutations caused by base damage (see also Base excision repair). ...
High Mobility Group or HMG is a group of chromosomal proteins that help with transcription, replication, recombination, and DNA repair. ...
Side effects 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 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.
Nephrotoxicity is a poisonous effect of some substances, both toxins and medication, on the kidney. ...
Creatinine clearance is a method that estimates the glomerular filtration rate (GFR) of the kidneys. ...
In medicine (nephrology) renal function is an indication of the state of the kidney and its role in physiology. ...
A diuretic (colloquially called a water pill) is any drug or herb that elevates the rate of bodily urine excretion (diuresis). ...
Reactive oxygen species (ROS) include oxygen ions, free radicals and peroxides both inorganic and organic. ...
In chemistry free radicals are uncharged atomic or molecular species with unpaired electrons or an otherwise open shell configuration. ...
Neurotoxicity occurs when the exposure to natural or manmade toxic substances ,which are called neurotoxins, alters the normal activity of the nervous system. ...
A nerve conduction study (NCS) is a test commonly used to evaluate the function, especially the ability of electrical conduction, of the motor and sensory nerves of the human body. ...
For other uses, see Nausea (disambiguation). ...
Vomiting (also throwing up or emesis) is the forceful expulsion of the contents of ones stomach through the mouth and sometimes the nose. ...
Ondansetron (INN) (IPA: ) is a serotonin 5-HT3 receptor antagonist used mainly to treat nausea and vomiting following chemotherapy. ...
Granisetron is used to prevent nausea and vomiting caused by cancer chemotherapy and radiation therapy. ...
In physiology, corticosteroids are a class of steroid hormones that are produced in the adrenal cortex. ...
Aprepitant (brand name: Emendâ„¢) is a medication, that is used in the treatment of chemotherapy induced nausea / emesis. ...
Ondansetron (INN) (IPA: ) is a serotonin 5-HT3 receptor antagonist used mainly to treat nausea and vomiting following chemotherapy. ...
Dexamethasone is a potent synthetic member of the glucocorticoid class of steroid hormones. ...
Ondansetron (INN) (IPA: ) is a serotonin 5-HT3 receptor antagonist used mainly to treat nausea and vomiting following chemotherapy. ...
Dexamethasone is a potent synthetic member of the glucocorticoid class of steroid hormones. ...
Ototoxicity is damage of the ear (oto), specifically the cochlea or auditory nerve and sometimes the vestibulum, by a toxin (often medication). ...
Broadly, melanin is any of the polyacetylene, polyaniline, and polypyrrole blacks and browns or their mixed copolymers. ...
The upper portion of the spiral ligament contains numerous capillary loops and small blood vessels, and is termed the stria vascularis. ...
Reactive oxygen species (ROS) include oxygen ions, free radicals and peroxides both inorganic and organic. ...
Alopecia is a set of disorders ranging from male and female pattern alopecia (alopecia androgenetica), to alopecia areata, which involves the loss of some of the hair from the head, alopecia totalis, which involves the loss of all head hair, to the most extreme form, alopecia universalis, which involves the...
Electrolyte disturbance refers to an abnormal change in the levels of electrolytes in the body. ...
History As a compound cisplatin was first described by M. Peyrone in 1845 (known as Peyrone's salt). The structure was elucidated by Alfred Werner in 1893. It was rediscovered in the 1960s by Barnett Rosenberg and van Campet al, who discovered that electrolysis products from a platinum electrode inhibited binary fission in Escherichia coli (E. coli) bacteria. The bacteria grow to 300 times their normal length but cell division fails. Alfred Werner (December 12, 1866 - November 15, 1919) was a German Nobel prize-winning chemist. ...
The 1960s decade refers to the years from January 1, 1960 to December 31, 1969, inclusive. ...
Barnett Rosenberg (1926 - ) is an American chemist best known for the discovery of the anti-cancer drug cisplatin. ...
This article is about the chemical process. ...
E. coli redirects here. ...
In the 1960s, a series of experiments were conducted at Michigan State University to test the effects the cis-diamminedichloroplatinum(II), along with other platinum coordination complexes, on sarcomas 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. Michigan State University (MSU) is a co-educational public research university in East Lansing, Michigan USA. Founded in 1855, it was the pioneer land-grant institution and served as a model for future land-grant colleges in the United States under the 1862 Morrill Act. ...
General Name, Symbol, Number platinum, Pt, 78 Chemical series transition metals Group, Period, Block 10, 6, d Appearance grayish white Standard atomic weight 195. ...
A sarcoma is a cancer of the connective or supportive tissue (bone, cartilage, fat, muscle, blood vessels) and soft tissue. ...
Species 50 species; see text *Several subfamilies of Muroids include animals called rats. ...
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 and other physico-chemical methods, revealed its ability to form irreversible crosslinks with bases in DNA. hi “FDA†redirects here. ...
Wikipedia does not yet have an article with this exact name. ...
References - ^ Woollins, J. D.; Woollins, A.; Rosenberg, B. Polyhedron, 1983, 2, 175-178.
- Rosenberg B, Vancamp L, Krigas T. Inhibition of cell division in Escherichia coli by electrolysis products from a platinum electrode. Nature 1965;205:698-9. PMID 14287410.
- Peyrone M. Ann Chemie Pharm 1845;51:129.
- Alderden, Hall and Hambley 'The Discovery and Development of Cisplatin' , Journal of Chemical Education, 2006, 83:728-724 (http://jchemed.chem.wisc.edu/journal/issues/2006/May/abs728.html).
Nature is one of the most prominent scientific journals, first published on 4 November 1869. ...
External links | Chemotherapeutic agents/Antineoplastic agents (L01) | | Alkylating agents | Nitrogen mustards: (Chlorambucil, Chlormethine, Cyclophosphamide, Ifosfamide, Melphalan). Nitrosoureas:(Carmustine, Fotemustine, Lomustine, Streptozocin). Platinum: (Carboplatin, Cisplatin, Oxaliplatin, BBR3464). Busulfan, Dacarbazine, Procarbazine, Temozolomide, ThioTEPA, Uramustine | | Antimetabolites | Folic acid: (Aminopterin, Methotrexate, Pemetrexed, Raltitrexed). Purine:(Cladribine, Clofarabine, Fludarabine, Mercaptopurine, Pentostatin, Thioguanine). Pyrimidine:(Capecitabine, Cytarabine, Fluorouracil, Floxuridine, Gemcitabine) | | Spindle poison/mitotic inhibitor | Taxane: (Docetaxel, Paclitaxel). Vinca: (Vinblastine, Vincristine, Vindesine, Vinorelbine). | | Cytotoxic/antitumor antibiotics | Anthracycline family: (Daunorubicin, Doxorubicin, Epirubicin, Idarubicin, Mitoxantrone, Valrubicin) - streptomyces (Actinomycin, Bleomycin, Mitomycin, Plicamycin) - Hydroxyurea | | Topoisomerase inhibitors | Camptotheca: (Camptothecin, Topotecan, Irinotecan), Podophyllum:(Etoposide, Teniposide) | | CI monoclonal antibodies | Alemtuzumab, Bevacizumab, Cetuximab, Gemtuzumab, Panitumumab, Rituximab, Tositumomab, Trastuzumab | | Photosensitizers | Aminolevulinic acid, Methyl aminolevulinate, Porfimer sodium, Verteporfin | | Tyrosine kinase inhibitors | Dasatinib, Erlotinib, Gefitinib, Imatinib, Lapatinib, Sorafenib, Sunitinib | | Other | retinoids (Alitretinoin, Tretinoin) - Altretamine, Amsacrine, Anagrelide, Arsenic trioxide, Asparaginase (Pegaspargase), Bexarotene, Bortezomib, Denileukin diftitox, Estramustine, Masoprocol, Mitotane | |
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