Talk:Prodrug

Cabamazepine / Carbamazepine

Cabamazepine is listed as having no page. I think that there is likely a mispelling. I got to this page from various steps related to Carbamazepine. Based on the content and the other pages I was looking at (which included a drug related to carbamazepine).Especially as it's listed in the section linked to livers, and as I'm taking carbamazepine I need to get regular liver tests. However I'm not a pharmacist so I'm not making the change to the page. Let me know if this ever comes in handy Marcie (talk) 02:33, 16 November 2009 (UTC)

Tidy-up

I simplified the first section. I used less technical language, and I removed the technical details of specific implementations. I do not believe they are necessary for the introductory/summary section. TheRealJoeWiki (talk) 01:45, 3 September 2012 (UTC)

Sadly, since my initial rewrite, the introductory section has been modified to make it too technical and difficult for the layman to read. Given that the point of the rewrite was to respond to the request to rewrite it for the layman, I shall undertake this again. Would you chemists mind leaving the technical jargon out of the first section? TheRealJoeWiki (talk) 03:53, 16 June 2013 (UTC)

The "History" contains very little history and is written in a way that focuses way too much on the technical aspects of how prodrugs work, instead of providing a useful history. However, it at least falls below the introduction, so I will leave it as is. TheRealJoeWiki (talk) 04:05, 16 June 2013 (UTC)

Proposed merge

I've proposed a merge between Active metabolite because these article appear to be about the same topic, and it would enhance the quality of information on both articles to have it presented in a single place. The articles could be split at a later date if need be. LT910001 (talk) 11:37, 16 October 2013 (UTC)

Conceptually, the two terms are related, but I would be careful about saying they are the same topic. There is a distinction between the two. The term prodrug is used for a medication that is designed to be metabolized into an active drug. The prodrug is typically inactive itself - the pharmacological action lies primarily with the metabolite. With an active metabolite, the parent drug very often is still pharmacologically more important. A prodrug produces an active metabolite, but an active metabolite doesn't necessary arise from a prodrug. There is probably a way to handle the two topics in the same article, but it may be easier to keep them separate even if they have some overlapping content. -- Ed (Edgar181) 11:57, 16 October 2013 (UTC)

Suggested points of expansion

Page needs expanding, with more references. I suggest adding a discussion of acetylation of salicylic acid as being an inspiration for acetylation of morphine (i.e., heroin, as suggested by others here). Also recommend referring to The Organic Chemistry of Drug Design and Drug Action by Silverman and discussion of fosphenytoin. The list of example prodrugs should also be alphabetical. It's missing a lot of examples (I just added cyclophosphamide). I'm a new Wiki editor, happy to take the lead. — Preceding unsigned comment added by PharmaPatentExaminer (talk • contribs) 06:15, 28 January 2014 (UTC)

Is lisdexamfetamine type IIA or type IIB?

This chart lists it as IIA:

https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3978533/table/pharmaceuticals-02-00077-t001/

But this Wikipedia article lists it as IIB. In addition, I've seen a few journal articles that claim the drug is metabolized by red blood cells, which (I believe) would suggest IIB.

Anyone with expertise care to weigh in? — Preceding unsigned comment added by 98.7.34.119 (talk) 22:22, 22 May 2017 (UTC)

Unsourced list of examples

Moved here per WP:PRESERVE. Per WP:BURDEN, pls don't restore without finding reliable sources, checking the content against them, and citing them.

Examples

• Aspirin
• 6-Monoacetylmorphine (6-MAM) is a heroin metabolite which converts into active morphine in vivo.
• ALD-52 and MLD-41 will both convert into the active psychedelic LSD-25.
• BL-1020 (perphenazine 4-aminobutanoate trimesylate) is converted into perphenazine and GABA into the brain.
• Carisoprodol is metabolized into meprobamate. Until 2012, carisoprodol was not a controlled substance in the United States, but meprobamate was classified as a potentially addictive controlled substance that can produce dangerous and painful withdrawal symptoms upon discontinuation of the drug.
• Chloramphenicol succinate ester is used as an intravenous prodrug of chloramphenicol, because pure chloramphenicol does not dissolve in water.
• Codeine is converted into morphine by cytochrome P450 enzyme CYP2D6.
• Cyclophosphamide is a prodrug activated by liver cytochrome P450 (CYP) enzymes to form the metabolite 4-hydroxy cyclophosphamide.
• Diethylpropion is a diet pill that does not become active as a monoamine releaser or reuptake inhibitor until it has been N-dealkylated to ethylpropion.
• Dipivefrine, given topically as an anti-glaucoma drug, is bioactivated to epinephrine.
• Enalapril is bioactivated by esterase to the active enalaprilat.
• Fenofibrate is an isopropyl ester of fenofibric acid.
• Fesoterodine is an antimuscarinic that is bioactivated to 5-hydroxymethyl tolterodine, the principle active metabolite of tolterodine.
• Fosamprenavir is hydrolyzed to the active amprenavir.
• Fospropofol is metabolized by alkaline phosphatases to an active metabolite, propofol.
• Heroin is deacetylated by esterase to the active morphine.
• Latanoprost is an isopropyl ester, that is hydrolyzed by esterases in the cornea to the biologically active acid.
• Leflunomide is rapidly metabolized to the active teriflunomide in the gut wall and liver.
• Levodopa is bioactivated by DOPA decarboxylase to the active dopamine.
• Lisdexamfetamine is L-lysyl amide that is metabolized in the bloodstream to dextroamphetamine at a controlled (slow) rate for the treatment of attention-deficit hyperactivity disorder
• Molsidomine is metabolized into linsidomine which decomposes into the active compound nitric oxide.
• Mycophenolate mofetil is an ester of mycophenolic acid used in transplant medicine.
• Olmesartan medoxomil is hydrolyzed to olmesartan during absorption from the gastrointestinal tract.
• Oseltamivir is an ethyl ester prodrug of Ro 64-0802, a selective inhibitor of influenza virus neuraminidase.
• Paliperidone is an atypical antipsychotic for schizophrenia. It is the active metabolite of risperidone.
• Prednisone, a synthetic corticosteroid drug, is bioactivated by the liver into the active drug prednisolone, which is also a steroid.
• Primidone is metabolized by cytochrome P450 enzymes into phenobarbital, which is major, and phenylethylmalonamide, which is minor.
• Psilocybin is dephosphorylated to the active psilocin.
• Tenofovir disoproxil fumarate is an anti-HIV drug (NtRTI class) that is bioactivated to tenofovir (PMPA).
• Valaciclovir is bioactivated by esterase to the active aciclovir.
• Ximelagatran is dealkylated and dehydroxylated to the active melagatran.

-- Jytdog (talk) 15:57, 28 October 2017 (UTC)

I concur with this constructive, redactive edit, and would encourage the editorial research work to return a component of this list, with sources, to the list. See also simvistatin section herein. Cheers.

Request for presentation of examples, starting queue

Per the previous entry, it seems wise and helpful to present a list of documented examples. Here is potential future content with preliminary sourcing, offered as a sandbox type of working list:

• Aspirin, the activity of which, for many anti-inflammatory and analgesic conditions, involves hydrolysis to salicylic acid ("salicylate") in the liver, as well as in the stomach, intestinal mucosa, and blood (an exception being antiplatelet-aggregation, mediated by the prodrug itself).

I would encourage that such societally important drugs as oseltamivir, prednisone, enalapril, and a morphine-family case be used as further examples, and that thereafter, choices be made on the basis of representing the breadth of prodrug chemistries. That is, for a comprehensive list, a list article should be created (perhaps starting from the sourced list generated here). Cheers.

Пролекарство это плохо!?

Тамифлю это пролекарство 89.113.141.133 (talk) 07:49, 11 September 2022 (UTC)