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« Nickel Carbonyl (Liquid, suffocating metal) | Main | Brodifacoum (Warfarin: with a vengance) »

Warfarin (Koagulation kops)

Category: Drugs
Posted on: January 22, 2007 6:14 PM, by Molecule of the Day

Warfarin belongs to a previously-covered class of molecules known as the coumarins. Coumarins see use both as anticoagulants (in people) and poisons (in certain small animals).

InChI=1/C19H16O4/c1-12(20)11-15(13-7-3-2-4-8-13)17-18(21)14-9-5-6-10-16(14)23-19(17)22/h2-10,15,21H,11H2,1H3

Warfarin works by inhibiting a crucial step in vitamin K metabolism. Its structure isn't so far off:

Vitamin K is named for the German koagulation. We get a lot of our chemical vocabulary from German - it wasn't that long ago that American chemistry undergrads had to take German as part of their degree. This is no longer the case, and it probably leads to a lot of frustration the first time people are looking over a periodic table: Ok, hydrogen, helium, lithium, beryllium, boron, carbon, nitrogen, oxygen, fluorine, neon, Na? K?

These come from the German natrium and kalium. If it weren't for English's Germanic roots, I guarantee you that chemical terms would make even less sense!

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Comments

Many years ago I used to walk by the Warf (Wisconsin Alumni Research Foundation) building in Madison amazed that it was built partly because of this drug, and its patent. I hope it continues a lonng time.

Posted by: Markk | January 22, 2007 6:54 PM

Wasn't it first discovered in fermented clover after a bunch of livestock bled to death after ingesting it? Not quite as nice as the discovery of artificial sweeteners, but another interesting serendipitous find.

Posted by: Jon | January 22, 2007 8:57 PM

The first off-campus house I (and six of my closest friends) first lived in as an undergrad had a mouse problem. At one point, we had both poison (could've been Warfarin, I suppose, but definitely an anticoagulant) AND spring traps out. All I can say is that if a mouse is unfortunate enough to gorge on anticoagulants and then survive long enough to find a trap, you may learn that a tiny mouse contains a shocking amount of blood. I don't think I'll ever forget the gruesome sight of the puddle on the kitchem floor one morning...

Posted by: Russ | January 23, 2007 8:29 AM

The word natrium, as well as many other 'strange' looking elemental symbols, actually have their roots in Latin.

Na - Natrium
K - Kalium
Cu - Cuprum
Sn - Stannum
Sb - Stibium
Hg - Hydrargyrum (actually Latinized Greek)
W - Wolfram
Pb - Plumbum

Just a little food for thought, I know all those years studying Latin would pay off...

Posted by: Around the corner and down the hal | January 23, 2007 8:55 AM

Looks like you are right, Kalium is apparently from Arabic actually! Thanks for the correction, I just deleted that part of the post, since there wasn't really a way to rework it in a way that made sense.

Posted by: MotD | January 23, 2007 9:56 AM

Just to be explicit, yes, warfarin is in fact named for the Wisconsin Alumni Research Foundation. The joke etymology "Wisconsin Anti-Rat Federation" was also used.

Posted by: Adam | January 24, 2007 8:51 PM

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