A platinum-containing chemotherapeutic drug, Cl2H6N2Pt, used in the treatment of metastatic ovarian or testicular cancers and advanced bladder cancer.
[CIS- + PLATIN(UM).]
cisplatin
Dictionary:
cis·pla·tin (sĭs-plā'tn)  |
n.
A platinum-containing chemotherapeutic drug, Cl2H6N2Pt, used in the treatment of metastatic ovarian or testicular cancers and advanced bladder cancer.
A platinum-containing chemotherapeutic drug, Cl2H6N2Pt, used in the treatment of metastatic ovarian or testicular cancers and advanced bladder cancer.
| 5min Related Video: cisplatin |
| Chemistry Dictionary: cisplatin |
A platinum complex, cis-[PtCl2(NH3)2], used in cancer treatment to inhibit the growth of tumours. It acts by binding between strands of DNA.
| Oncology Encyclopedia: Cisplatin |
Key Terms: Anemia, Chemotherapy, DNA, Electrolytes, Food and Drug Administration, Intravenous, Metastatic, Neutropenia.
Definition
Cisplatin, also known by the brand name Platinol-AQ, Cis-platinum, CDDP, or DDP, is a chemotherapy medicine used to treat certain types of cancer by destroying cancerous cells.
Purpose
Cisplatin is approved by the Food and Drug Administration (FDA) to treat metastatic testicular cancer and metastatic ovarian cancer. It is also approved for late-stage bladder cancer and has been used to treat other types of cancer including head and neck cancer, esophageal cancer, stomach cancer, lung cancer, skin cancer, prostate cancer, lymphoma and others (breast, neuroblastoma, sarcoma, bladder, cervical, myeloma, mesothelioma, osteosarcoma).
Description
Cisplatin is a member of the group of chemotherapy drugs known as heavy metal alkylating-like agents. These drugs interfere with the genetic material (DNA) inside the cancer cells and prevent them from further dividing and growing more cancer cells.
Cisplatin has been used to treat cancer for more than 30 years. It can be used alone or in combination with other chemotherapies, including bleomycin-etoposide, ifosfamide, gemcitabine, paclitaxel, fluorouracil-leucovorin, vinorelbine, methotrexate-vinblastine-doxorubicin. Cisplatin may also be given with radiation therapy.
Recommended dosage A cisplatin dose can be determined using a mathematical calculation that measures body surface area (BSA), which depends on a person's overall size. Body surface area is measured in the units known as square meter (m2). The body surface area is calculated and then multiplied by the drug dosage in milligrams per m2 (mg/m2), which gives the proper dosage.
Cisplatin is a clear, colorless solution administered by an infusion into a vein. Infusions can be given once every three to four weeks over a 30 minutes up to two hours. It can also be given continuously over 24 hours a day for several days in a row. One cycle of cisplatin should not be given more frequently than once every three to four weeks. Dosages depend on the cancer being treated.
To Treat Metastatic Testicular Cancer
Dosages are 20 mg/m2 per day administered into a vein every day for five days in a row. This regimen is used in combination with other chemotherapy drugs, mainly bleomycin and etoposide or vinblastine.
To Treat Metastatic Ovarian Cancer
Dosages are 50 mg/m2 to 100 mg/m2 administered into a vein once every four weeks. This regimen can be combined with the chemotherapy drug cyclophosphamide or doxorubicin.
To Treat Advanced Bladder Cancer
Cisplatin doses range from 50 mg/m2 to 70 mg/m2 administered into a vein once every 3 to 4 weeks. Cisplatin is usually given alone for bladder cancer.
Before receiving cisplatin large volumes of intravenous fluids are given to keep the kidneys flushed with water. If patients have severe kidney problems the physician will either not use cisplatin or decrease the dose being used.
Normal metal ions found in the body, called electrolytes, can be lost due to administration of cisplatin. These may be added to these intravenous fluids for replacement.
Precautions
When receiving cisplatin, it is important to drink a lot of fluids to help flush the kidneys and prevent kidney damage. Patients also receive additional fluids through their veins before, during, and after receiving cisplatin.
Blood counts will be monitored regularly while on cisplatin therapy. During a certain time period after receiving cisplatin, there is an increased risk of getting infections. Caution should be taken to avoid unnecessary exposure to crowds and people with infections.
Patients with a known previous allergic reaction to chemotherapy drugs or any other medications should tell their doctor.
Patients who may be pregnant or trying to become pregnant should also tell their doctor before receiving cisplatin.
Chemotherapy can cause men and women to be sterile (not able to have children).
Patients should check with their doctors before receiving live virus vaccines while on chemotherapy.
An additional difficulty that can arise with cisplatin and other platinum-based anticancer drugs is that some tumor cells develop resistance to the drug. These resistant cells can then regrow and multiply. One strategy against drug resistance is to develop new drugs that can be used together with cisplatin to target resistant cells. In February 2004 the FDA approved pemetrexed (Alimta) for use together with cisplatin in the treatment of certain types of lung cancer. Another strategy for defeating tumor resistance to cisplatin is genetic modification of the resistant tumor cells. This approach in still in the early stages of experimentation as of 2004.
Side Effects
Common side effects include nausea and vomiting, which can begin from 1 hour after receiving the drug and last as long as a week. Patients are given medicines known as antiemetics, before and after receiving cisplatin to help prevent or decrease this side effect. Diarrhea has also been known to occur.
A serious common side effect related to the total dose of cisplatin received is kidney damage, which can occur in up to one-third of patients. Taking fluids before, during and after receiving cisplatin help prevent this from occurring. In addition, some researchers in Brazil have reported that quercetin, a yellowish plant pigment found in apples and onions, shows promise as a protective treatment against kidney damage related to cisplatin.
Hearing damage can also occur in up to one-third of patients. Patients may experience ringing in the ears and hearing loss of high-pitched frequency. Hearing tests may be requested before and/or after cisplatin therapy. One promising treatment for cisplatin-related hearing damage is vitamin E, which is being studied by a group of researchers in Illinois.
Low blood counts, referred to as myelosuppression, are expected due to cisplatin administration. When the white blood cell count is low this is called neutropenia and patients are at an increased risk of developing a fever and infections. Platelets are blood cells in the body that allow for the formation of clots. When the platelet count is low, patients are at an increased risk for bruising and bleeding. Low red blood cell counts, referred to as anemia, may also occur due to cisplatin administration. Low red counts make people feel tired.
Cisplatin can also cause damage to nerves and nervous system tissues. Patients may feel tingling, numbness and sometimes burning of the fingers and toes. This side effect is common and can be severe.
Less common side effects include change of taste sensation, loss of appetite, dizziness, seizures, confusion, muscle cramps, and uncontrolled muscle contractions. Men treated with cisplatin for testicular cancer sometimes develop so-called dry ejaculations. Other side effects include, hair loss (alopecia), hiccups, rash, allergic reactions with difficulty breathing, swelling, and a fast heart rate.
Cisplatin may cause the body to waste normal electrolytes that circulate in the body (potassium, magnesium, phosphate, sodium, calcium) resulting in low levels of these electrolytes. These will be monitored by the doctor and replacement drugs will be given if necessary.
All side effects should be reported to the doctor or nurse.
Interactions
Patients should avoid other drugs that may cause damage to the kidneys.
Certain water pills and cisplatin given together may increase the risk of hearing damage. Before starting any medications, patients should notify their doctors.
Cisplatin may make medications that control seizures less effective.
Resources
Books
Karch, A. M. Lippincott's Nursing Drug Guide. Springhouse, PA: Lippincott Williams & Wilkins, 2003.
Periodicals
Fossa, S. D. "Long-Term Sequelae after Cancer Therapy—Survivorship After Treatment for Testicular Cancer." Acta Oncologica 43 (February 2004): 134–141.
Francescato, H. D., T. M. Coimbra, R. S. Costa, and L. Bianchi Mde. "Protective Effect of Quercetin on the Evolution of Cisplatin-Induced Acute Tubular Necrosis." Kidney and Blood Pressure Research 27 (March 2004): 148–158.
Funato, T. "Utility of Antioncogene Ribozymes and Antisense Oligonucleotides in Reversing Drug Resistance." Methods in Molecular Medicine 106 (2004): 215–234.
Hazarika, M., R. M. White, J. R. Johnson, and R. Pazdur. "FDA Drug Approval Summaries: Pemetrexed (Alimta)." Oncologist 9 (March 2004): 482–488.
Kalkanis, J. G., C. Whitworth, and L. P. Rybak. "Vitamin E Reduces Cisplatin Ototoxicity." Laryngoscope 114 (March 2004): 538–542.
Organizations
American Society of Health-System Pharmacists (ASHP). 7272 Wisconsin Avenue, Bethesda, MD 20814. (301) 657-3000.
United States Food and Drug Administration (FDA). 5600 Fishers Lane, Rockville, MD 20857-0001. (888) INFO-FDA.
—Nancy J. Beaulieu, RPh., BCOP; Rebecca J. Frey, PhD
| Dental Dictionary: cisplatin |
n
An antineoplastic prescribed in the treatment of a wide variety of neoplasms such as metastatic testicular, prostatic, and ovarian tumors.
| Drug Info: Cisplatin |
Brand names: Platinol®Platinol®-AQ
Chemical formula:
- Español:
- Cisplatino, Solución para inyección
Cisplatin Solution for injection
What is this medicine?
CISPLATIN (SIS pla tin) is a chemotherapy drug. It targets fast dividing cells, like cancer cells, and causes these cells to die. This medicine is used to treat many types of cancer like bladder, ovarian, and testicular cancers.
This medicine may be used for other purposes; ask your health care provider or pharmacist if you have questions.
What should I tell my health care provider before I take this medicine?
They need to know if you have any of these conditions:
•blood disorders
•hearing problems
•kidney disease
•recent or ongoing radiation therapy
•an unusual or allergic reaction to cisplatin, carboplatin, other chemotherapy, other medicines, foods, dyes, or preservatives
•pregnant or trying to get pregnant
•breast-feeding
How should I use this medicine?
This drug is given as an infusion into a vein. It is administered in a hospital or clinic by a specially trained health care professional.
Talk to your pediatrician regarding the use of this medicine in children. Special care may be needed.
Overdosage: If you think you have taken too much of this medicine contact a poison control center or emergency room at once.
NOTE: This medicine is only for you. Do not share this medicine with others.
What if I miss a dose?
It is important not to miss a scheduled appointment. If you miss a scheduled appointment, contact your prescriber or health care professional as soon as possible.What may interact with this medicine?
•dofetilide
•foscarnet
•medicines for seizures
•medicines to increase blood counts like filgrastim, pegfilgrastim, sargramostim
•probenecid
•pyridoxine used with altretamine
•rituximab
•some antibiotics like amikacin, gentamicin, neomycin, polymyxin B, streptomycin, tobramycin
•sulfinpyrazone
•vaccines
•zalcitabine
Talk to your doctor or health care professional before taking any of these medicines:
•acetaminophen
•aspirin
•ibuprofen
•ketoprofen
•naproxen
This list may not describe all possible interactions. Give your health care provider a list of all the medicines, herbs, non-prescription drugs, or dietary supplements you use. Also tell them if you smoke, drink alcohol, or use illegal drugs. Some items may interact with your medicine.
What should I watch for while using this medicine?
Your condition will be monitored carefully while you are receiving this medicine. You will need important blood work done while you are taking this medicine.
This drug may make you feel generally unwell. This is not uncommon, as chemotherapy can affect healthy cells as well as cancer cells. Report any side effects. Continue your course of treatment even though you feel ill unless your doctor tells you to stop.
In some cases, you may be given additional medicines to help with side effects. Follow all directions for their use.
Call your doctor or health care professional for advice if you get a fever, chills or sore throat, or other symptoms of a cold or flu. Do not treat yourself. This drug decreases your body's ability to fight infections. Try to avoid being around people who are sick.
This medicine may increase your risk to bruise or bleed. Call your doctor or health care professional if you notice any unusual bleeding.
Be careful brushing and flossing your teeth or using a toothpick because you may get an infection or bleed more easily. If you have any dental work done, tell your dentist you are receiving this medicine.
Avoid taking products that contain aspirin, acetaminophen, ibuprofen, naproxen, or ketoprofen unless instructed by your doctor. These medicines may hide a fever.
Do not become pregnant while taking this medicine. Women should inform their doctor if they wish to become pregnant or think they might be pregnant. There is a potential for serious side effects to an unborn child. Talk to your health care professional or pharmacist for more information. Do not breast-feed an infant while taking this medicine.
Drink fluids as directed while you are taking this medicine. This will help protect your kidneys.
Call your doctor or health care professional if you get diarrhea. Do not treat yourself.
What side effects may I notice from receiving this medicine?
Side effects that you should report to your doctor or health care professional as soon as possible:
•allergic reactions like skin rash, itching or hives, swelling of the face, lips, or tongue
•signs of infection - fever or chills, cough, sore throat, pain or difficulty passing urine
•signs of decreased platelets or bleeding - bruising, pinpoint red spots on the skin, black, tarry stools, nosebleeds
•signs of decreased red blood cells - unusually weak or tired, fainting spells, lightheadedness
•breathing problems
•changes in hearing
•gout pain
•low blood counts - This drug may decrease the number of white blood cells, red blood cells and platelets. You may be at increased risk for infections and bleeding.
•nausea and vomiting
•pain, swelling, redness or irritation at the injection site
•pain, tingling, numbness in the hands or feet
•problems with balance, movement
•trouble passing urine or change in the amount of urine
Side effects that usually do not require medical attention (report to your doctor or health care professional if they continue or are bothersome):
•changes in vision
•loss of appetite
•metallic taste in the mouth or changes in taste
This list may not describe all possible side effects. Call your doctor for medical advice about side effects. You may report side effects to FDA at 1-800-FDA-1088.
Where should I keep my medicine?
This drug is given in a hospital or clinic and will not be stored at home.
Last updated: 7/1/2002
Important Disclaimer: The drug information provided here is for educational purposes only. It is intended to supplement, not substitute for, the diagnosis, treatment and advice of a medical professional. This drug information does not cover all possible uses, precautions, side effects and interactions. It should not be construed to indicate that this or any drug is safe for you. Consult your medical professional for guidance before using any prescription or over the counter drugs.
| Wikipedia: Cisplatin |
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Cisplatin
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| Systematic (IUPAC) name | |
| (SP-4-2)-diamminedichloroplatinum | |
| Identifiers | |
| CAS number | 15663-27-1 |
| ATC code | L01XA01 |
| PubChem | 84691 |
| DrugBank | APRD00359 |
| Chemical data | |
| Formula | H6Cl2N2Pt |
| 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) |
| Legal status | |
| Routes | Intravenous |
 (what is this?) (verify) |
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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 a class of anti-cancer drugs which now also includes carboplatin and oxaliplatin. These platinum complexes react in vivo, binding to and causing crosslinking of DNA which ultimately triggers apoptosis (programmed cell death).
Contents |
Pharmacology
Following administration, one of the chloride ligands is slowly displaced by water (an aqua ligand), in a process termed aquation. The aqua ligand in the resulting [PtCl(H2O)(NH3)2]+ is itself easily displaced, allowing the platinum atom to coordinate to a basic site in DNA. Subsequently, crosslinking of two DNA bases occurs via displacement of the other chloride ligand.[1] 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. Recently it was shown that the apoptosis induced by cisplatin on human colon cancer cells depends on the mitochondrial serine-protease Omi/Htra2[2]. Since this was only demonstrated for colon carcinoma cells, it remains an open question if the Omi/Htra2 protein participates in the cisplatin-induced apoptosis in carcinomas from other tissues.
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.
Note that although cisplatin is frequently designated as an alkylating agent, it has no alkyl group and cannot carry out alkylating reactions. It is correctly classified as alkylating-like.
Usage
Cisplatin is administered intravenously as short-term infusion in physiological saline for treatment of solid malignacies.
Cisplatin resistance
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 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.[3] Oxaliplatin is active in highly cisplatin-resistant cancer cells in the laboratory, however there is little evidence for its activity in the clinical treatment of patients with cisplatin-resistant cancer.[3] The drug Paclitaxel may be useful in the treatment of cisplatin-resistant cancer; the mechanism for this activity is unknown.[4]
Transplatin
Transplatin, the trans stereoisomer of cisplatin, has formula trans-[PtCl2(NH3)2] and 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.[citation needed] 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 which can easily be separated and detected by HPLC.[5]
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 (e.g., amifostine). 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 (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 does not generally affect 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
The compound cis-PtCl2(NH3)2 was first described by M. Peyrone in 1845, and known for a long time as Peyrone's salt.[6] The structure was deduced by Alfred Werner in 1893.[1] In the 1960s, Barnett Rosenberg, 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 of various platinum coordination complexes on sarcomas artificially implanted in rats. This study found that cis-PtCl2(NH3)2 was the most effective out of this group, which started the medicinal career of cisplatin.[7]
Approved for clinical use by the United States Food and Drug Administration (FDA) in 1978,[8][1] it revolutionized the treatment of certain cancers. Detailed studies on its molecular mechanism of action, using a variety of spectroscopic methods including X-ray, NMR spectroscopy, and other physico-chemical methods, revealed its ability to form irreversible crosslinks with bases in DNA.
Synthesis
The synthesis of cisplatin is a classic in inorganic chemistry. Starting from potassium tetrachloroplatinate(II), K2[PtCl4], 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 bound ammine ligand. Because Cl− has a larger trans effect than NH3, the second ammine preferentially substitutes trans to a chloride ligand, and therefore cis to the original ammine. The trans effect of the halides follows the order I->Br->Cl-, therefore the synthesis is conducted using [PtI4]2− 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.[9][10]
References
- ^ a b c Stephen Trzaska (20 June 2005). "Cisplatin". C&EN News 83 (25). http://pubs.acs.org/cen/coverstory/83/8325/8325cisplatin.html.
- ^ Pruefer FG, Lizarraga F, Maldonado V, Melendez-Zajgla J (June 2008). "Participation of Omi Htra2 serine-protease activity in the apoptosis induced by cisplatin on SW480 colon cancer cells". J Chemother 20 (3): 348–54. PMID 18606591. http://www.jchemother.it/cgi-bin/digisuite.exe/searchresult?range=pubmed&volume=20&year=2008&firstpage=348.
- ^ a b Stordal B, Davey M (November 2007). "Understanding cisplatin resistance using cellular models". IUBMB Life 59 (11): 696–9. doi:. PMID 17885832.
- ^ Stordal B, Pavlakis N, Davey R (December 2007). "A systematic review of platinum and taxane resistance from bench to clinic: an inverse relationship". Cancer Treat. Rev. 33 (8): 688–703. doi:. PMID 17881133.
- ^ J. D. Woollins, A. Woollins and B. Rosenberg (1983). "The detection of trace amounts of trans-Pt(NH3)2Cl2 in the presence of cis-Pt(NH3)2Cl2. A high performance liquid chromatographic application of kurnakow's test". Polyhedron 2 (3): 175–178. doi:.
- ^ Peyrone M. (1845). Ann Chemie Pharm 51: 129.
- ^ Rosenberg, B.; Van Camp, L.; Krigas, T. (1965). "Inhibition of cell division in Escherichia coli by electrolysis products from a platinum electrode". Nature 205 (4972): 698–699. doi:.
- ^ "Approval Summary for cisplatin for Metastatic ovarian tumors". FDA Oncology Tools. Food and Drug Administration, Center for Drug Evaluation and Research. 1978-12-19. Archived from the original on 2008-02-08. http://web.archive.org/web/20080208232952/http://www.accessdata.fda.gov/scripts/cder/onctools/summary.cfm?ID=73. Retrieved 2009-07-15.
- ^ Dhara, S. C. (1970). Indian Journal of Chemistry 8: 193–134.
- ^ Rebecca A. Alderden, Matthew D. Hall, and Trevor W. Hambley (2006). "The Discovery and Development of Cisplatin" (abstract). J. Chem. Ed. 83: 728–724. http://jchemed.chem.wisc.edu/journal/issues/2006/May/abs728.html.
External links
- Cisplatin: The Invention of an Anticancer Drug by Andri Smith
- Anti-cancer Agents: A treatment of Cisplatin and their analogues by Sia M. Liu (excellent detailed overview)
- MedlinePlus page on cisplatin
- IARC Monograph: "Cisplatin"
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 | DDP |
| carboplatin |
| 5-fluorouracil |
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