Over the years, I've given medicine to hundreds of cats. This has not always been a good experience --- for the cats or for me. I've gotten bitten and scratched, and cats who were my friends suddenly decided I was an enemy to be avoided at all costs. You can learn a lot from hurt feelings, and hurt hands! Here are a couple of the things I've learned.
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As with everything "cat," your attitude will determine whether you succeed or fail and whether the cat will love or hate you by the time you get the medication down his throat. If you're nervous and apprehensive, the cat will take full advantage of your weakened mental state. But if you're confident and positive and treat him gently and with love and respect, he'll probably choke down the medication willingly. Most cats respond positively to a "we're in this together" attitude.
-- Coercion is the best way to turn a friend into an enemy. Yes, you'll probably get the
medicine into the cat if you wrap him in a towel, back him into a corner or drag him out from under a bed. But if you do that more than a couple of times, he could become afraid of you for life. So it's important to find a way of administering medication that's acceptable to both of you. And that's especially true if your cat has a chronic disease that will require daily medication for the rest of his life.

Painless Pilling
When your cat needs medication, try to make the experience as pleasant as possible for both of you. Here are some suggestions:
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If your cat has a chronic disease that requires daily medication, consider having the medicine compounded into a flavor he likes. Compounding pharmacies can add a variety of flavors, including tuna and chicken. And some medications can be made into a topical cream that you rub into the inside of the cat's ear tip.
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Sandwich the pill into a soft moist treat. Even if the pill falls out of the treat, the cat will eat it because it tastes like the treat. Or, cut a treat with a soft center (Temptations, for instance) in half, put the pill into the soft center and reassemble the treat.
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Most pet supply stores sell Pill Pockets, or buy them online at Pillpockets.com. These are treats with a little pocket for hiding a pill. While Pill Pockets have gotten rave reviews from many people (and cats), my cats don't like them. And I've tried them with a couple of cats I pet sit for who took one sniff and walked away.
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Hide the pill in a little bit of food. Most cats know when their food has been tampered with and won't eat it. So use something your cat doesn't eat all the time. Turkey and ham baby food make great disguises for pills. So does a little bit of tuna. Try hiding a whole pill in the food first. If you crush the medication, and the cat doesn't eat all of the food, you won't know how much medicine he's gotten.
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Wrap the pill in a "treat" food, like cheese or liverwurst. For years, one of my cats got Tapazole and heart medication in tiny cheese balls twice a day. His favorite was Monterey Jack, but he also liked white American cheese.
-- Dissolve the pill in a tiny bit of water, liquid from a can of tuna or meat baby food and syringe it into the cat using a 1 CC plastic syringe. You should be able to get one from your vet.

The Straightforward Approach
If you and your cat decide the straightforward approach is best for the two of you, this is the way that works best for my cat friends and me. Be aware though that swallowing a pill without water is no easier for a cat than it is for you! And the pill could become lodged in the cat's esophagus causing very paindful erosive esophagitis. 
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Be positive and upbeat: "Let's do your medicine."
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Sit on the floor with the cat, and wrap your legs around the him while petting his head or scratching his neck. If he's the kind of cat who will swat at you just for the fun of it, sit with his back to you and press your knees around him.
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Open his mouth and drop or gently toss the pill into his mouth just beyond the hump in his tongue. Let him close his mouth. Do this quickly!
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Rub his throat or blow gently in his face to make him swallow. Opening his mouth just a little bit will also make him swallow. While you're doing this, tell him what a smart cat he is to take his medicine because it will make him feel much better.
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The second he swallows the pill, give him some canned food or liquid from a can of tuna. This will not only show how much you appreciate his cooperation, it will move the pill out of his throat and on its way to his stomach.

Liquid Medication
I find small plastic syringes easier to manage than the droppers that come with liquid medication. You can get a syringe from your vet.

Pills And Pet Sitters
If your cat doesn't know your pet sitter well or if he's difficult to medicate, ask the pet sitter to do a trial visit before you leave town. She should come when you're not home to track down and reassure the cat. If she finds that she can't medicate him without a lot of stress for both of them, he might be better off spending your vacation at the vet's. If boarding is not an option and your cat is very shy, confine him to a comfortable, sunny room. Put barricades around anything he could hide under. The stress of being chased around his own house or dragged out from under a bed by a total stranger could offset all the benefits of the medicine.

A Few Words About Health Care
Since animals speak a language very few humans understand, you need to become an advocate for your animal's health care. Take full advantage of the Internet to research any illness your cat or dog may have. And make your wishes, and your animal's, very clear to your vet. If he hates taking pills, tell your vet you need liquid medication. If he doesn't like that either, and he's on medication for life, insist that the vet become familiar with compounding pharmacies and call your cat's or dog's prescription in to one. Capsules are difficult for cats to swallow because they get sticky when wet, so ask for an alternative. Also ask for an alternative to very large pills that need to be cut into pieces, forcing you to pill the cat several times in one sitting. Most dogs will gulp down a pill in some peanut butter or cheese. Vets sometimes need to be reminded that cats are not small dogs!        

--- Missy Zane
How To Medicate Your Cat And Still Be Friends
Painless Pilling


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