Volume 90 Issue 3 | pp. 36-37
Issue Date: January 16, 2012

Where Drug Names Come From

Behind every generic name lies a specific process
Department: Science & Technology
Keywords: Generic names, nomenclature, drug development
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MATCH GAME
See how quickly you can match each generic drug name to its definition. Need help? Use the official list of generic drug name stems from the US Adopted Names Council: http://www.ama-assn.org/resources/doc/usan/stem-list-cumulative.pdf
Generic-drug name quiz homepage.
 
MATCH GAME
See how quickly you can match each generic drug name to its definition. Need help? Use the official list of generic drug name stems from the US Adopted Names Council: http://www.ama-assn.org/resources/doc/usan/stem-list-cumulative.pdf

It isn’t every day that a molecular moniker is on the docket at Illinois’ Cook County Circuit Court. But then, the 2002 case of cis-8-methyl-N-vanillyl-6-nonenamide was most unusual.

The trouble wasn’t with the compound’s International Union of Pure & Applied Chemistry-approved name. It was that cis-8-methyl-N-vanillyl-6-nonenamide also happens to be a medication. Drug molecules get an additional, simpler name called a nonproprietary name or generic name. Winston Pharmaceuticals, a company that develops products based on cis-8-methyl-N-vanillyl-6-nonenamide, sought to change that molecule’s generic name, which an independent body had chosen in-line with decades of drug-naming conventions. If the case went Winston’s way, more than a name on a box would have been at stake.

Drug naming rarely involves drama. But this example illuminates a little-talked-about layer in drug development, one that affects doctors, pharmacists, and patients.

Unlike IUPAC-sanctioned chemical names, generic names usually describe a drug’s physiological function rather than its chemical structure. Today’s regimented generic-naming process got its start in the 1960s, a time when drugs had grown complex in structure and IUPAC names had grown to unwieldy lengths. In 1961, the American Medical Association, the U.S. Pharmacopeial Convention, and the American Pharmacists Association created the U.S. Adopted Names (USAN) Council to select concise generic names. The Food & Drug Administration joined the effort in 1967.

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Credit: Shutterstock/C&EN
These are some of the stems used to name generic drugs based on the drug's structure, target, and function.
 
Credit: Shutterstock/C&EN

Today, the USAN Council names the active ingredients in drugs, biologics, vaccines, and even contact lenses and sunscreens. The council recommends names to the World Health Organization’s (WHO) International Nonproprietary Names (INN) program, which ultimately chooses a single name for each new drug that’s acceptable worldwide. For drugmakers, obtaining a generic name is a required part of bringing new products to market. Choosing a brand, or trade, name is an entirely separate process.

USAN Council members believe it’s important to develop drug names that are free for anyone to use, says Ruta Freimanis, who served as associate executive secretary and then as executive secretary of the USAN Council between 1978 and 2000. Brand names might be handy at first, “but eventually drugs do go off patent,” she says. A generic name “can go in the literature, on package labels, or even in educational materials” without copyright issues related to brand names, she explains.

The naming process itself “is an evolving type of science,” says Stephanie C. Shubat, the current director and secretary to the USAN Council. Generic names have evolved from being truncated versions of chemical terminology to being largely independent of it, she explains.

A list of naming rules, some of them quirky, has evolved as well. The letters h, j, k, and w are off-limits because they lead to pronunciation problems in other languages. Drugmakers can suggest names to the USAN Council, but any name with an implication that a drug is better, newer, or more effective than the competition heads straight for the reject pile, Shubat says. When a prospective name reaches the WHO stage, international connotations come into play. A name that sounds perfectly fine in English might have bad or even obscene connotations elsewhere. No one wants to sell the Chevy Nova of the drug world.

The crux of the generic-naming system is a collection of short name fragments called stems. Each stem has a meaning connected to a particular drug class or mode of action. The official list of USAN and INN stems and substems has grown and changed over time as companies come up with new classes of drugs, Shubat explains.

Understanding drug names through stems is a lot like learning English vocabulary by studying Greek and Latin roots. Learn what the stems mean, and you’re most of the way to figuring out what a drug does. Take top-selling drug Nexium, which has a generic name of esomeprazole. The stem in that name is -prazole, which means the drug is a benzimidazole antiulcer agent. The drug’s es- prefix describes the nature of the drug’s chirality—esomeprazole is dextrorotatory and contains a chiral center in the S configuration.

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Naming Convention
Drugmakers propose generic names for new drugs by starting with stems that describe structure, function, and targets, then tacking on syllables of their choice.

Game Online: Test your knowledge by matching drugs' generic names to their definitions.
These generic-drug names are broken down to explain what each stem represents.
 
Naming Convention
Drugmakers propose generic names for new drugs by starting with stems that describe structure, function, and targets, then tacking on syllables of their choice.

Game Online: Test your knowledge by matching drugs' generic names to their definitions.

A prefix, in fact, was a player in the Winston case. The generic name Winston wanted to change, zucapsaicin, contains the prefix “zu,” which comes from German chemical nomenclature and indicates a cis isomer. Zucapsaicin is the cis isomer of capsaicin, a compound in chili peppers. The molecule targets a specific ion channel and can be used to treat pain, inflammation, or itch, says Joel E. Bernstein, a physician and Winston’s chief executive officer. Winston requested a name change from zucapsaicin to civamide, which according to the company was commonly used in hospitals and pharmacies.

It’s possible to change generic names, but only on rare occasions, and usually only for safety reasons. In 2009, for instance, the entire family of botulinum toxin drugs, which includes the popular cosmetic Botox, got a generic-name makeover in light of reports of serious side effects and deaths from dosage mix-ups.

Winston did not win its court case. A 2004 petition to FDA to change the name didn’t work out either. The name zucapsaicin was found to be in-line with established naming precedents. As for name confusion among physicians and pharmacists, the USAN Council concluded Winston was partly to blame.

The name zucapsaicin had been on the books since 1994. The council negotiated the name with a company called GenDerm, which owned the rights to the drug at the time. Civamide was a generic name GenDerm suggested. After that name was rejected, GenDerm continued to use the name civamide in the literature and its documentation. Winston continued the practice when it acquired the rights to the drug in 1999.

Most of the documents Winston cited to support its claim are dated after 1994, wrote then-USAN program director Sophia V. Fuerst in a letter to Winston. It’s both Winston and GenDerm’s “use of the name civamide after the name zucapsaicin was adopted that has caused the confusion,” she wrote.

Bernstein disputes that idea. Still, he says, “we weren’t able to get USAN to change their mind, nor FDA, so we have zucapsaicin.”

Most of the time, a simple back-and-forth between a company and the USAN Council is enough to settle any name disputes, says John E. Kasik, professor emeritus at the University of Iowa Carver College of Medicine and a longtime member of USAN’s review board, which settles naming spats. In fact, the review board has only had to step in to resolve five disputes throughout its decades-long existence.

Sometimes small disagreements occur when a manufacturer asks for a new stem to be created, Shubat says. It’s the council’s job to keep naming as streamlined as possible, which means being conservative when it comes to adding new stems, she explains.

“Manufacturers have to supply concrete arguments as to what differentiates their compound to qualify for a new stem,” Freimanis says. Drugs within the same category are different, she says, “otherwise manufacturers wouldn’t be selling them.”

Once the council builds in stems, prefixes, and other conventions, “a lot of times a name is three-quarters predetermined,” Shubat says. Once in a while, though, companies get to do something special with the syllable or two they supply. Onyx Pharmaceuticals’ experimental multiple myeloma treatment carfilzomib is named after molecular biologist Philip Whitcome and his wife, Carla, who both succumbed to cancer. (The ph in Philip was changed to an f to make the name compatible with multiple languages.) Philip Whitcome was a founder of the company Proteolix, which first developed carfilzomib, says Onyx spokeswoman Lori Melançon. With the name, the company “wanted to celebrate both Phil and Carla’s legacy,” she says.

Bristol-Myers Squibb’s experimental hepatitis C drug asunaprevir gets part of its name from Li-Qiang Sun, the chemist who first made it, says Joel C. Barrish, BMS’s vice president of medicinal chemistry.

And dasatinib, a chronic myelogenous leukemia medication BMS markets under the brand name Sprycel, is named for research fellow Jagabandhu Das. Das, or Jag, as he’s known around the labs, didn’t discover dasatinib. “What Jag did was challenge dogma,” Barrish explains. On two separate occasions, Das’s discoveries pulled his teammates out of medicinal chemistry ruts.

Long after a drug’s patent expires, “it’s the generic name that will always be remembered,” Barrish says. “Being able to recognize Jag that way for his accomplishments made the whole team feel good.”


Read about how Jagabandhu Das earned a namesake drug at CENtral Science blog The Haystack, cenm.ag/das.


 
Chemical & Engineering News
ISSN 0009-2347
Copyright © American Chemical Society
Comments
Paul Bracher (January 16, 2012 2:57 AM)
Awesome story!
» Reply
Vicki Crooms (January 18, 2012 1:41 AM)
Really cool story.
» Reply
John Kalasky (January 18, 2012 2:04 PM)
I'm training to be a physician and this is a great article. It should be required reading in for all Pharmacology courses on day one. Thank you.
Eric Walters (January 18, 2012 3:01 PM)
The HIV protease inhibitor darunavir was named for its discoverer, Dr. Arun Ghosh, of Purdue University
Carmen Drahl (January 22, 2012 10:55 AM)
Thanks for your comments, everyone. And Eric, thanks for the tip- I will have to look into the darunavir story.
Larry Mavis (January 28, 2012 11:55 AM)
I have had students planning medical careers. To spark interest I've tried unsuccessfully to find this information. Thanks for the article!
Harold Shaw (August 7, 2012 3:17 PM)
As a senior citizen I've wondered for a long while how my several medications got their names. Now I know. What a great article..

Of course I don't understand it yet but I will after the third or fourth reading.
AnilKumar (February 19, 2013 11:42 PM)
Kindly give me the diference between generic Names and generic drugs
Anonymous (March 7, 2013 1:48 PM)
kindly use google
Khang Tran (March 19, 2013 1:44 AM)
To answer your question about the difference between generic name and generic drug:
1. Generic name vs. brand name: A drug always has at least two names: a brand name and a generic name. A generic name is a common name that describes the chemical agent. For example, bupropion (an antidepressant). Brand names are unique names that the drug manufacturers come up with to differentiate different formulations, and to make it easier to market them for certain purpose. For example, bupropion may be called Wellbutrin when it is intended to treat depression. It can also be used for smoking cessation with a formulation called Zyban. A drug can have only 1 generic name, but it can have multiple brand names depending on the indications.
2. Generic drug vs. branded drug: This refers to who makes the drug that you are buying. When a drug is first introduced to the market, the company with the patent on it will sell it as a branded product at a much higher price because they have the exclusive right to sell it. After a certain number of years, the patent runs out. When that happens, generic-drug manufacturers have the right to produce similar formulations of that drug that contain the same active ingredient. These are called generic drugs. While a branded product is typically made by one company (i.e., the one that originally has the patent to it), the generic version can be made by many generic manufacturers.
Cynthia Farrington (March 26, 2013 9:27 PM)
Thank you for this explanation on how drugs are named. I worked as a Nursing Supervisor for 15 years in a small hospital and had to retrieve medications from the pharmacy during the night. All the drugs were placed on the shelf in order generically. Many doctors wrote their orders using the brand/trade name. I became very familiar with the generic names of most drugs. Now that I have retired, I have pondered the question of how these names are chosen and by whom. My husband and I have discussed this issue often, but I decided to Google it and found your information. It is very well written and I am so happy to finally have the answer to my question.
Carol Morris (April 25, 2013 7:53 AM)
Would I be able to name a new medicine on my own? Like in a contest? Or, would I have to work for a drug company.
Carmen (April 26, 2013 6:20 AM)
Hi Carol- it is the USAN council that comes up with most of the names new medicines. Sometimes a company gets to pick a syllable or two and sometimes not. Your question is interesting - to my knowledge there's not been a contest to pick out that last bit of a name.
David (April 16, 2014 6:05 PM)
Hi, wondering if you can tell me why the drug Rasburicase is called Fasturec (in Europe anyway)and also why it is called Rasburicase?
I would be grateful also if you could give me a good website as to the origin of drug names.

Kind regards,

David
Stella Reed (May 31, 2014 1:48 PM)
Hi,
Can you give me any information as to how Ofatumumab and / or Arzerra was named?
Thank you.
Mary S Palmer (October 10, 2015 2:19 PM)
I LOVED this article as I knew Phil and Carla personally and it made me so pleased to see these wonderful folks so Honored!
A. Evan Lewis PhD, MD (February 6, 2016 9:31 PM)
Although this is an excellent and informative article I think as a physician it is time for a revision in the methods used to develop the names of generic drugs. These names are far too difficult for many lay people, and especially older people, to pronounce, let alone remember. Even university professors stumble over them.

It is unlikely that we will avoid having two names for every drug, but at least we could simplify the names we assign to generic drugs. The stem on the end of the name is useful for identifying a group of drugs which belong to a particular class, but careful attention to making names easy to pronounce and spell is critically important in our attempts to improve safety in medicine. The current system is failing in this regard. Take for example abciximab, fondaparinux, dabigatran, rivaroxiban, ofatumumab. These are horribly complicated names. It is hard to believe that the American Medical Association and Pharmaceutical societies actually support this process.
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