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How do some medicines derive their names?

For instance, is the name oxycodone somewhat arbitrary? I am not well-versed in Chemistry (1st semester student) but does the prefix oxy- imply some chemical meaning as well as the -codone such as some sort of functional group or grouping of molecules?

I realize such nomenclature such as di- implies "two".

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    $\begingroup$ Note that oxy also means "sharp", and not always necessarily has to do with oxygen (it's probably not the case here, but still). There are several families and genera of living animals (snakes, birds, worms, ...) starting with oxy too, however I doubt there is a direct correlation with chemistry (Oxybelis, Oxycontin, Oxydendrum, Oxylebius, Oxytropis, Oxyura, Oxyuranus etc.). $\endgroup$ – andselisk Jan 4 '18 at 11:24
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    $\begingroup$ As for other words, drugs names usually have an etymology that is not completely arbitrary. For example, the etymology dictionary etymonline.com offers this explanation for the origin of oxycodone: "from (hydr)oxy(l) + codeine". As for codeine, "coined, with chemical suffix -ine, from Greek kodeia "poppy head". $\endgroup$ – toliveira Jan 4 '18 at 17:47
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    $\begingroup$ The sarcastic answer $\endgroup$ – chipbuster Jan 4 '18 at 18:38
  • $\begingroup$ Being a student you should do this exercise. And if it doesn't make sense then come back and try again when you have taken organic chem. Look at the structures for codeine, hydrocodone, and oxycodone and then look at the structures for morphine, hydromorphone, and oxymorphone. You'll start to see part of the pattern. $\endgroup$ – Delta_G Jan 4 '18 at 21:05
  • $\begingroup$ @toliveira, you raised a perfectly valid point. Indeed the name oxycodone is not random at all, but has lots of Chemistry attached to, which I tried to highlight below $\endgroup$ – xavier_fakerat Jan 8 '18 at 4:17
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The reason why the generic name of most drugs have seemingly little semblance to their chemistry is in the interests of practicality; a doctor would find it easier to write sildenafil (generic name) or Viagra (brand name) in a prescription than 5-{2-Ethoxy-5-[(4-methylpiperazin-1-yl)sulfonyl]phenyl}-1-methyl-3-propyl-1$\ce{H}$,6$\ce{H}$,7$\ce{H}$-pyrazolo[4,3-d]pyrimidin-7-one (chemical name) unless he had a weird fetish for IUPAC nomenclature .

As for how manufacturers (and the relevant regulatory bodies) arrive at those generic and brand names, msdsmanuals.com has a take on this,

When a drug is under patent protection, the company markets it under its brand name. When the drug is off-patent (no longer protected by patent), the company may market its product under either the generic name or brand name. Other companies that file for approval to market the off-patent drug must use the same generic name but can create their own brand name. As a result, the same generic drug may be sold under either the generic name (for example, ibuprofen) or one of many brand names (such as Advil or Motrin).

Furthermore, they add,

Generic names are usually more complicated and harder to remember than brand names. Many generic names are a shorthand version of the drug’s chemical name, structure, or formula. In contrast, brand names are usually catchy, often related to the drug’s intended use, and relatively easy to remember, so that doctors will prescribe the drug and consumers will look for it by name. Brand names often suggest a characteristic of the drug. For example, Lopressor lowers blood pressure, Glucotrol controls high blood sugar (glucose) levels, and Skelaxin relaxes skeletal muscles. Sometimes, the brand name is simply a shortened version of the drug’s generic name—for example, Minocin for minocycline.

I found equally useful information on popsci.com,

As for commercial names, pharmaceutical companies are reluctant to share their strategies. These are hugely important brands, even after the patents expire--nobody knows what Sildenafil citrate is, but everyone knows its brand name of Viagra. And the odds are you know someone who insists on brand-name Tylenol instead of discount-store acetaminophen.

Though pharmaceutical companies contacted by PopSci wouldn't share their marketing secrets, you can still derive a drug's molecular and popular heritage just by studying its name. Like, for example, Tylenol. Its chemical name is $\ce{N}$-acetyl-p-aminophenol--see the -tyl and -ol in there? Then there's Viagra. It doesn't sound like sildenafil, but it certainly suggests vigor and virility--exactly what Pfizer wants you to think. Xeljanz, which was approved earlier this year after almost 20 years of research, targets a protein called Janus kinase. It works in a different cellular pathway from other arthritis drugs. That's where you get the -jan part of that name, which, to someone with a drug decoder, connotes its uniqueness.

As for oxycodone specifically, it's anyone's guess, since that information can't be found (online) easily enough.


Note: I've italicized all generic and brand names because, well... they're generic and brand names. Italicizing actual chemical/IUPAC names is against convention, so don't get the wrong idea ;-)

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    $\begingroup$ PopSci mistake: "Like, for example, Tylenol. Its chemical name is N-acetyl-p-aminophenol--see the -tyl and -ol in there?" - actually, it ends in the whole enol, not just ol... $\endgroup$ – Izkata Jan 4 '18 at 19:17
  • $\begingroup$ @Izkata Yup that looks like the case, good catch! :-) $\endgroup$ – paracetamol Jan 4 '18 at 19:23
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    $\begingroup$ I think there's a piece missing here, which is that the generic drug names are not selected by the manufacturers (as you said in paragraph 2) but ultimately (in the US) by the United States Adopted Name council, although perhaps with input from the original manufacturer. The USAN's nomenclature is partly systematic, and this is why the generic names of the related benzodiazepine antianxiety drugs clonazepam, diazepam, lorazepam, etc. all end in -azepam. The NLM has a (partial) list of such suffixes. $\endgroup$ – MJD Jan 4 '18 at 20:44
  • $\begingroup$ @MJD I'm not based in the US, but that's an understandable point you've raised. I've made an edit to the question (hopefully, it improves the accuracy of this post). Thanks! :-) $\endgroup$ – paracetamol Jan 4 '18 at 21:51
  • $\begingroup$ @flurbiprofen Well, I said "...it's anyone's guess, since that information can't be found (online) easily enough.". It was supposed to be interpreted as "I can't find that info easily enough, so until someone else posts a more precise answer about it, you'll have to make do with what's in my post" ;-) This post (and the sources I've cited) concur on the fact that generic names are (far more often than not) derived from the drug's chemical constitution or physiological function; it's just that I lack the resources/connections required to obtain oxycodone's etymology reasonably quickly. :-) $\endgroup$ – paracetamol Jan 8 '18 at 12:48
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The naming of drugs is not completely a randomised process but depends on various factors most of which are linked to origins, chemistry or any modifications during the drug discovery pipeline although in old times serendipity discovery often led to trivial names being given to drugs.

While morphine seems have been named arbitrarily, the same is not true for its synthetic derivatives . In the opioid class morphine and codeine are considered prototype drugs to which other derivatives are synthesised:

Note: the additional 3-methoxy group gives rise to the -cod- stem name.

e.g. hydromorphone (a synthetic derivative of morphine prepared by the catalytic hydrogenation 7,8 double bond and dehydrogenation of morphine under acidic conditions) hydrocodone (3 methoxy version of hydromorphone) oxycodone (14 beta-hydroxyl version of hydrocodone) and oxymorphone (4 beta-hydroxyl version of hydromorphone, analogous to the hydrocodone, oxycodone pair)


How are drugs named?

Most drugs have at least three different names by which they can be recognised. These are their chemical, generic (non proprietary) and trade (proprietary) names. Chemicals names of drugs are extremely cumbersome to use that they they are almost never used except by pharmacologists and chemists such a name for example: N-(2,6 dimethylphenyl)-5,6-dihydro-4H-1,3-thiazin-2-amine, which is more commonly known as xylazine.

Every drug has several different names, and some have a very large number. This abundance of names is often a source of confusion and can indeed be dangerous. The various names have different origins and uses.

To avoid using this, a simplified name method has evolved where original drug manufacturers together with appropriate drug authorities derive a simplified chemical name from the full name. The simplified chemical name can mean little with respect of the chemical name since at times random extraction of pieces of the chemical name are used to produce a name easier to recall. e.g diazepam:

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Drugs are named in a variety of ways. During the drug’s earliest stages of development, the first name it receives is the chemical name. The chemical name provides scientific and technical information because it is a precise description of the substance in accordance with chemical nomenclature rules established by the International Union of Pure and Applied Chemistry (IUPAC). The chemical name describes the chemical structure of the drug. Because they are long and complex, however, chemical names are rarely used in clinical medicine.

The generic name is commonly used to describe the active drug(s) in the product and is easier to pronounce and remember than the chemical name.

Morphine is derived form the Greek god of sleep, Morpheus (Morphine was isolated from opium in 1806 by a German pharmacist, Seturner. He named the compound “morphine” after the Greek god of dreams “Morpheus.”).

On the other hand Salbutamol derived from its chemical name which includes salicyl, butyl, amine and alcohol groups another similar example is acetaminophen or paracetamol.

Other names are derived from the nature of the drug or how it is isolated from the parent substance for example monoclonal antibodies: because the original monoclonal antibodies (mAbs) were of mouse origin and therefore immunogenic, newer generation mAbs are genetically engineered to modify the mouse regions to appear more “humanized.” mAb nomenclature indicates “-umab” e.g adalimumab as human (produced using transgenic technology), “-ximab” e.g rituximab as chimeric, and “-zumab” e.g alemtuzumab as humanized.

Chemical name

There are precise rules for naming chemical compounds, and the chemical name defines the structure of the drug molecule. Because of this the chemical name of a drug is complex and unsuitable for use inprescribing.

Approved name (or generic)

The approved name is the official name given to the drug. It is usually a short name based on the drug's chemical structure and has the advantage that related drugs have similar names. The approved name is the one which should be used in prescribing.

Proprietary or trade name

The proprietary name is the commercial name given to the drug by the pharmaceutical company which makes and promotes it. Newer drugs are only protected by patent for a few years after their introduction so it is important for the manufacturer to firmly establish the trade name during this period so that when it is out of patent the drug will continue earning revenue. After the patent period runs out, other manufacturers can market the drug and usually introduce new trade names, resulting in the same drug marketed under many different names.


An example case study

The process for naming a marketable drug involves five steps: new chemical entity (NCE) submission and patent application, generic naming, brand naming, FDA review, and final approval.

The U.S Adopted Names Council USAN Council is responsible for creating and assigning generic names to chemicals that appear to have potential as new drugs.

The USAN Council has several criteria for a generic name. The name must be appropriate for the drug; short, easy to pronounce, and euphonic; and suitable for routine use both in the United States and internationally. The name cannot be misleading or confusing or imply efficacy or application to particular anatomical parts. The name often has a stem common to related drugs (e.g., angiotensin-converting-enzyme inhibitors end in "pril"). The USAN Council attempts to minimize similarities with other drug names,


References

  1. Names and classes of drugs. P. Lewis, Essential Clinical Pharmacology. © P. J. Lewis 1981

  2. Veterinary Drug Use, Prescribing, Acquisition, and Pharmacy Management. Brand Name (®) Or Not?

  3. Wilson and Gisvold’s Textbook of Organic Medicinal and Pharmaceutical Chemistry, 12th ed

  4. Naming of drugs: Fundamentals of Pharmacology: Drug nomenclature. Gralbraith et al

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