WASHINGTON — A federal crackdown on the Florida pain pill market will pit Walgreens against the Drug Enforcement Administration in a high-level and multi-front legal battle that comes to a capital courtroom this week.

Represented in part by the former U.S. solicitor general, the nation’s largest retail pharmacy company is challenging the DEA’s effort to stop a major South Florida distribution center from shipping controlled substances like oxycodone, a powerful painkiller. Both sides are sounding alarms, as they prepare to face off Thursday before the U.S. Court of Appeals for the District of Columbia Circuit.

“This case involves an abuse of the extraordinary power that the Drug Enforcement Administration wields over ordinary citizens and businesses in the fight against diversion of certain prescription drugs,” Walgreens attorneys said in one brief.

The DEA counters that the company’s busy distribution center in Jupiter, Fla., had a troubled history of filling suspicious drug orders and posed an imminent danger to public safety.

The Jupiter facility, one of 13 distribution centers operated by Walgreens nationwide, shipped drugs to more than 850 pharmacies throughout Florida and surrounding states. “DEA’s investigation revealed that, even when managers recognized that orders plainly raised suspicions, they continued to make shipments without conducting inquiries,” Justice Department attorneys state in a brief.

Underscoring the stakes, Walgreens’ position will be argued Thursday by Gregory G. Garre, who as solicitor general in 2008 served as the George W. Bush administration’s top lawyer.

He has argued more than three dozen times before the U.S. Supreme Court, and his appearance during the 20-minute oral argument Thursday will be before an appellate panel often considered to be the nation’s second-highest court.

Walgreens spokesman Jim Graham said Tuesday that the company will let the legal filings “be the full expression of our views” for the time being.

Last year, another D.C.-based federal judge upheld a similar DEA action against a drug distribution facility in Lakeland, Fla., run by Cardinal Health. Investigators cited a “staggeringly high and exponentially increasing rate of oxycodone distribution” by the Lakeland facility.

The DEA acted following a six-month investigation into the Jupiter facility, the largest distributor of oxycodone products throughout Florida.

Investigators, for instance, found that one Walgreens pharmacy in a Florida town of fewer than 3,000 residents had been supplied with 3,271 bottles of oxycodone in a single 40-day period.

One company official wondered in an email obtained by investigators how the store managed to “even house this many bottle(s),” but distribution continued.