| I currently work at a drug store; here's some of the money-saving techniques we tell our customers about:
If there's a generic available, get it. I can only think of three drugs where it is difficult to switch to a generic: Coumadin (generic name: Warfarin Sodium), Synthroid (generic name: Levothyroxine Sodium), and (depending on the health of the patient) Lanoxin (generic name: Digoxin). But this is not because of any flaw in the generics. Warfarin is an anticoagulant; Levothroid is for the thyroid; Lanoxin is a cardiac glycoside. Because they require such a delicate balance in the system, it's not recommended to switch brands if you can avoid it. If a doctor writes you a prescription for Synthroid, Coumadin, or Lanoxin, get the generic the very first time, or you may be stuck taking the overpriced brand name until a dosage change is required.
Make sure the doctor is making the generic available If the doctor writes a prescription for a brand name then writes "DAW" or "dispense as written" or checks a box on the script that says that, ask them why they aren't allowing you to get the generic. If you come into the drugstore with a DAW script for a brand name, we can't legally give you the generic unless the doctor authorizes a new prescription.
Also, there are some brand name drugs without a generic that are in the same family of drugs as a different brandname that has a generic available. Ultracet, for example, contains acetaminophen along with the same drug as Ultram (generic name: Tramadol). It might save you money to get a prescription for Tramadol and take OTC acetaminophen instead. If the doctor writes a prescription for acetaminophen, the pharmacist may be able to run the OTC acetaminophen through as a prescription so you don't have to pay sales tax on it. Which brings us to the next tip:
Some OTC's can be run through as prescriptions so you don't have to pay sales tax Also, if this is an OTC that legally can be ran through as a prescription, you may also be able to tax deduct it.
Avoid drugs that re-patent themselves with new names to keep you from changing to generics. The most successful drug I can think of that employs this dirty trick is Nexium (the "new" purple pill). Nexium is the same basic molecule as Prilosec (which is OTC and has a very affordable prescription generic, Omeprazole), only Nexium is a mixture of "left hand" and "right hand" molecule and Prilosec is only the "right hand" molecule. (see Isomer node if curious about this) There's a rumor going around that Nexium works better because it's "new" and is a mixture of both kinds. Lies, all lies. The study used to say Nexium works better was comparing 40mg strength Nexium to 20mg strength Prilosec. Very misleading.
Make sure you have refills before you drive to the drugstore This will save you gas and time. Calling the drugstore is the best way to check this. Just because a bottle you have says "x number of refills" doesn't guarantee you have that many. The prescription may have expired (most expire after one year), or you may be looking at an older bottle.
Splitting pills Certain drugs (Lipitor, Pravacol, and Zocur expecially) cost very little more for a higher dose. If you don't pay a flat copay, ask how much money you could save if you bought half as many pills in a double dose and split them (assuming it's in a form that can be split). The drugstore I work at splits pills for free (A thank you would be nice, though we rarely get one). It's possible to quarter pills, but the drugstore won't do this for you because pills have a tendency to crumble and the drugstore doesn't want to be held liable for that. One of our customers is supposed to take Zocur 10, so he buys Zocur 80 and carefully splits it into eighths. His insurance company allows him to get four months worth of pills for one copay this way. Sometimes it is possible, through splitting of pills, to get more than one month at a time, but it depends on your insurance, number of refills, and applicable laws. If you have a flat copay, getting more than one month for one copay can save you money (but keep in mind most insurances don't allow it). Having your doctor specify that the directions are "use as directed" can make it easier to get a larger-than-one-month supply covered by one copay. If you do this, make sure that you know what the directed use is (eg. "1/2 tablet every morning with food"). The prescription will not say this, so please don't expect the pharmacist to know.
If your insurance and the government allows (and you have enough refills), getting more than one month at a time might save you money. There is a per-ticket fee for every prescription (to pay for the bottle, label, sack, paperwork, etc), so getting several months at once (if feasible) can remove some of the per-ticket fees if you don't have a flat copay. If you have a flat copay, you may be able to get more than one month (3 months at a time usually, called a "vacation override") and only pay the one copay. This depends on your insurer though, so please don't blame the pharmacist if your insurer doesn't allow it. For control drugs, there is very little possibility that you can get more than one month at a time. Please do not expect the pharmacist to break the law for you. It's not going to happen.
Please do not be rude to the people at the drugstore. Not all of these tips are going to work in every situation. Often your insurance or a law may get in the way. We didn't pick your insurance, and we have to abide by the law. If you are mean to us when we're trying to help you, we will be less likely to tell you about money-saving opportunities in the future because we will be in a hurry to get you out of the store and far away from us.
(Please do not msg me for medical advice. I'm not a doctor or a pharmacist. More importantly, I'm not your doctor or pharmacist.)
An alternate version of this wu has been concurrently published as Post of the Day at The Motley Fool. | 
