Talk:Cisplatin

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POV verbiage?

The previous version contained lots of POV verbage, most of it due to bias or in an attempt to sound like a popular science journalist. Cisplatin "saving lives" is a bit dramatic. JFW | T@lk 15:12, 14 Apr 2005 (UTC)

Excepting its use in the treatment of testicular cancer, where it has taken a mostly incurable disease and converted it to one most persons survive.Pproctor 04:37, 10 August 2006 (UTC)[reply]

Paclitaxel action unknown?

If you click through on this drug, it describes the mechanism of action: disturbance of microtubule dynamics. Suggesting, this latter sentence to be removed removed, which is referenced with article [14]: "The drug paclitaxel may be useful in the treatment of cisplatin-resistant cancer; the mechanism for this activity is unknown.[14] — Preceding unsigned comment added by Ansjovis86 (talk • contribs) 14:02, 6 July 2015 (UTC)[reply]

Cervical cancer chemo easier on black women?

According to this article, Cisplatin causes less resitance among Black women.

http://www.sciam.com/article.cfm?id=cervical-cancer-chemo-eas

A note of caution: A recent paper on Nature Genetics (Ross et al.2009, Genetic variants in TPMT and COMT are associated with hearing loss in children receiving cisplatin chemotherapy) shows that there is a race-related difference in the frequency of occurrence of a SNP increasing susceptibility to ototoxicity (and they cite another study regarding nephrotoxicity). Africans seem to be, as a population, more subject to these side effects than Caucasians or Asians.

Perin Paola (talk) 13:06, 24 February 2010 (UTC)Paola Perin[reply]

toxicity on normal tissue

Can anyone say why/if it preferentially damages tumours. Does it have more effect at certain stages of mitosis ? Why does it damage kidneys more than tissues that divide more often such as gut linings ? Rod57 (talk) 15:24, 12 December 2009 (UTC)[reply]

The reason seems to be that cisplatin does not penetrate inside gut cells, but does enter tumor cells and kidney cells (and inner ear, for the same reason). Membrane transports involved in cisplatin uptake in tumour are still unclear (copper transporters are a candidate, but remember that not all tumors are equal), but in kidney and ear OCT2 seems to be a major player, as shown here.

http://www.ncbi.nlm.nih.gov/pubmed/20110413?itool=EntrezSystem2.PEntrez.Pubmed.Pubmed_ResultsPanel.Pubmed_RVDocSum&ordinalpos=3

Interestingly, the same study shows that cimetidine blocks ototoxicity and reduces nephrotoxicity induced by cisplatin. However, they do not show whether antitumoral activity is preserved in these conditions. - Perin Paola (talk) 13:29, 24 February 2010 (UTC)[reply]

BIN1 and c-MYC involved in resistance

[1] says "the c-MYC oncoprotein decreases production of BIN1, a c-MYC inhibitor. BIN1 usually suppresses an enzyme essential for DNA repair. Thus the sensitivity of cancer cells to cisplatin depends upon BIN1 abundance". Rod57 (talk) 15:14, 26 March 2011 (UTC)[reply]

Naming

I admit that plenty of genuinely reputable sources use the double "M" for the full chemical name. However, it is unquestionable that "Amine" in any usage, is always used with 1 "m." perhaps there should be a note about this. The other names, which are more specific to the use of this chemical as a drug, are not at issue. The issue is the proper chemical name, which is technically incorrect, though there are journals with it spelled this way. Any chemist, IUPAC, or other wielder of correct chemical naming conventions will agree 100%. Doctors (MD) may disagree, but this is SPECIFICALLY a question of the CHEMICAL (as opposed to its "Drug" name) name. I suggest either a correction or at the very least a note mentioning the discrepancy to alleviate the vast hordes of undergraduates learning about isomerism (this is probably the most widely non-organic pedagogical example of the example of complex isomerism).68.6.76.31 (talk) 06:52, 6 April 2011 (UTC)[reply]

Well actually, when an amine is a ligand it becomes an ammine; see Ammine complex, and this is the IUPAC recommendation from Nomenclature_of_Inorganic_Chemistry. Just like when water is a ligand it becomes aquo. The names change, although in this case it is slightly confusing because it is so similar to amine. Chris (talk) 10:15, 6 April 2011 (UTC)[reply]

I assume the above text was meant to have "aqua" as the name for coordinated water and not aquo (aqua = IUPAC rule since 1970); any ligand ending in -o is negative. — Preceding unsigned comment added by Reedijk (talk • contribs) 14:49, 30 July 2011 (UTC)[reply]

I agree that there should be something in the lead to explain the name. I suspect very many readers familiar with "amine" but not with "ammine" have done a double take at the name and looked either here or on google to find out, but many more have wondered and not bothered. --Dan Wylie-Sears 2 (talk) 20:53, 1 September 2011 (UTC)[reply]

Side effect references

Hello, I have been looking up different references for the side effects. I was wondering how is it possible to get someone to remove the banner regaurding the not cited work under side effects? thank youBeckejac (talk) 17:07, 19 April 2012 (UTC)[reply]

Side Effects

My sister is taking Cisplatin right now. Early on she developed a rather severe problem with something I can only describe as tinitus. After talking with her doctor she was told that the Cisplatin will cause that in a small percentage of people. highwayman65251 (talk) 16:10, 10 May 2012 (UTC)[reply]

Dunno if you're still reading this. I had small bower cancer and after surgery was given Fluoruracil chemotherapy. It dramatically increased my tinitus. My oncologist told me that that is a common side effect of many chemotherapy drugs. — Preceding unsigned comment added by 58.167.145.28 (talk) 09:06, 8 March 2019 (UTC)[reply]

Platinum-based anticancer drugs

The new Platinum-based anticancer drugs from Wikipedia:Wiki Ed/UCLA/Chem 171 Winter 2016 (Winter 2016) should be looked at and if needed merged or ........

--Stone (talk) 20:36, 14 March 2016 (UTC)[reply]

Announce changes

My name is Florian Schaub at Merck KGaA. My aim is to make some little changes in this article. From our point of view squamous cell carcinoma of the head and neck should be added to the passage "Medical Use". Ormaplatin and Zeniplatin can also be added to "See also". Please let me know if anyone has concerns.

--Florian Schaub at Merck KGaA (talk) 18:00, 31 May 2016 (UTC)[reply]

Thanks for the note and the disclosure of your potential COI. We would only have a Ormaplatin and Zeniplatin under "see also" if we actually had articles to see. You are welcome to start them if you think that they are notable. I encourage you to make the changes about the other aspect. Happy editing.--Smokefoot (talk) 17:34, 31 May 2016 (UTC)[reply]

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Structure

This is a planar, specifically square-planar molecule, is it not? If it is, why is it shown with (unnecessary) above-plane and below-plane stereochemistry?HowardJWilk (talk) 20:49, 7 May 2017 (UTC)[reply]

The molecule as a whole is not planar as the hydrogen atoms cannot be arranged symmetrically above and below the plane defined by the chlorine and nitrogen atoms. Petergans (talk) 09:22, 27 February 2018 (UTC)[reply]

Mechanism of action

"Cisplatin interferes with DNA replication, which kills the fastest proliferating cells, which in theory are carcinogenic.  Following administration, one of the two chloride atoms is slowly displaced by water to give the aquo complex cis-[PtCl(NH₃)₂(H₂O)]⁺, in a process termed aquation.  Dissociation of the chloride 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.^[1]^[2]

This is in direct disagreement with a recent article by Lippard himself which shows ^[3] the conversion of the cisplatin molecule, cis-[PtCl₂(NH₃)₂] to the diaqua complex cis-[Pt(H₂O)₂(NH₃)₂]²⁺, not the mono-aqua, mono-chloro complex that is now cited in the article. Although the mono-chloro complex must be formed an an intermediate in the hydrolysis process, it will be destroyed in a second hydrolysis reaction. Petergans (talk) 15:18, 2 March 2018 (UTC)[reply]

Equilibrium concentrations

The hydrolysis of cis-Pt(NH₃)₂Cl₂) is an equilibrium process, with the following equilibrium constants. Reference B Kankia,T Funck,L Marky; J.Solution Chem., 28,1249 (1999)

Pt(NH₃)₂ Cl₂ + H₂O ⇌ [Pt(NH₃)₂(H₂O) Cl]⁺+ Cl^- ; logK₁=2.60

[Pt(NH₃)₂(H₂O) Cl]⁺ + H₂O ⇌ [Pt(NH₃)₂(H₂O)₂]²⁺ + Cl^- ; logK₂=4.52

Therefore, it is incorrect to say that cis-platin is converted into the di-aqua complex on passing into a cell. What happens is that the uncharged molecule passes through the cell membrane more easily than the charged species. Then, as the chloride concentration is lower inside the cell, the equilibria are shifted to the right, increasing the proportions present of both the mono-aqua complex and di-aqua complex relative to the di-chloro complex, compared to the concentrations present when the platinum complexes are outside the cell.

In view of the aggressive reactions to my previous edits, I will not make the required changes myself. Petergans (talk) 09:18, 5 March 2018 (UTC)[reply]

References

^ Wang, Dong; Lippard, Stephen J. (2005). "Cellular processing of platinum anticancer drugs". Nature Reviews Drug Discovery. 4 (4): 307–320. doi:10.1038/nrd1691. ISSN 1474-1776.
^ Johnstone, Timothy C.; Suntharalingam, Kogularamanan; Lippard, Stephen J. (2016). "The Next Generation of Platinum Drugs: Targeted Pt(II) Agents, Nanoparticle Delivery, and Pt(IV) Prodrugs". Chem. Rev. 116: 3436–3486. doi:10.1021/acs.chemrev.5b00597. PMC 4792284. PMID 26865551.
^ Riddell, Imogen A.; Lippard, Stephen J. (2018). "Figure 2, p 6 in, Chapter 1. Cisplatin and Oxaliplatin:Our Current Understanding of Their Actions )". In Sigel, Astrid; Sigel, Helmut; Freisinger, Eva; Sigel, Roland K. O. (eds.). Metallo-Drugs:Development and Action of Anticancer Agents. Berlin: de Gruyter GmbH. pp. 1–42. doi:10.1515/9783110470734-007.

An obviously unfinished sentence.

Under Side Effects -> Nephrotoxicity, we have this sentence: "The dose should be reduced when the person's kidney function." This is obviously incomplete. Can someone knowledgeable please complete it? — Preceding unsigned comment added by 58.167.145.28 (talk) 09:07, 8 March 2019 (UTC)[reply]

Good catch. Added "impaired" from citation. Sandcherry (talk) 20:57, 8 March 2019 (UTC)[reply]

[WangLippard2005-1] Wang, Dong; Lippard, Stephen J. (2005). "Cellular processing of platinum anticancer drugs". Nature Reviews Drug Discovery. 4 (4): 307–320. doi:10.1038/nrd1691. ISSN 1474-1776.

[2] Johnstone, Timothy C.; Suntharalingam, Kogularamanan; Lippard, Stephen J. (2016). "The Next Generation of Platinum Drugs: Targeted Pt(II) Agents, Nanoparticle Delivery, and Pt(IV) Prodrugs". Chem. Rev. 116: 3436–3486. doi:10.1021/acs.chemrev.5b00597. PMC 4792284. PMID 26865551.

[3] Riddell, Imogen A.; Lippard, Stephen J. (2018). "Figure 2, p 6 in, Chapter 1. Cisplatin and Oxaliplatin:Our Current Understanding of Their Actions )". In Sigel, Astrid; Sigel, Helmut; Freisinger, Eva; Sigel, Roland K. O. (eds.). Metallo-Drugs:Development and Action of Anticancer Agents. Berlin: de Gruyter GmbH. pp. 1–42. doi:10.1515/9783110470734-007.

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