Two “Unresolvable” Prescribing/Dispensing Red Flags Unfurled

We appreciate receiving feedback on our blog posts.  We received a response to our post on the prescribing red flags indicating the likelihood of certain prescriptions filled by Walgreens pharmacies “were invalid because they lacked a legitimate medical purpose or were not issued in the usual course of professional practice.”  Press Release, Walgreens Agrees To Pay Up to $350M for Illegally Filling Unlawful Opioid Prescriptions and Submitting False Claims, U.S. Attorney’s Office, Northern District of Illinois, April 21, 2025, quoted here.

We noted that the Drug Enforcement Administration (“DEA”) had explained in its 2021 Gulf Med Pharmacy decision that prescribing red flags do not prohibit pharmacies from filling a prescription but are potential signs of diversion or risks to patient harm that pharmacists must resolve before filling.  Gulf Med Pharmacy; Decision and Order, 86 Fed. Reg. 72,694, 72,703 (Dec. 22, 2021).  Our reader informed us of two additional prescribing/dispensing red flags that DEA has alleged are “unresolvable” that he wanted to share with the pharmacy community.

The first “unresolvable” red flag is the continued prescribing and dispensing of immediate-release/short-acting opioids after two or three months.  Immediate-release/short-acting opioids act faster than extended-release/long-acting opioids.  DEA alleged that the pharmacy at issue dispensed oxycodone 30 mg., oxycodone/acetaminophen 10/325, hydromorphone 8 mg., and tramadol 50 mg. tablets to patients over the course of many months.  DEA specifically alleged that the pharmacy dispensed immediate-release opioids over a significant period of time, often at the highest strength available and in combination with other immediate-release opioids.

While prescribing immediate-release/short-acting opioids as a red flag is not new, that it is considered “unresolvable” is.  DEA’s position is contrary to statements made in the agency’s 2024 Coconut Grove decision when its expert opined at the hearing that filling immediate-release opioids prescribed and dispensed over a period of one and a half to two years “presented red flags and [the pharmacy] needed to properly resolve these red flags before dispensing.”  Coconut Grove Pharmacy; Decision and Order, 89 Fed. Reg. 50,372, 50,375, (June 13, 2024).  That decision includes a footnote stating that the expert “did not testify as to a specific time period that would cause concern, but made clear that a patient taking immediate-release opioids for ‘30, 60 days maximum’ would be acceptable and that over two years would be ‘very concerning.’”  Id. at 50,374-75 n.18.

The assertion that prescribing immediate-release opioids longer than two or three months is a red flag may have originated with the Center for Disease Control and Prevention (“CDC”) 2022 Clinical Practice Guideline for Prescribing Opioids for Pain.  The Guideline recommends that when clinicians begin opioid therapy for acute pain (of less than one month), subacute pain (of between one to three months) and chronic pain (longer than three months), they should prescribe immediate-release opioids instead of extended release-long-acting opioids.  Deborah Dowell et al., CDC Clinical Practice Guideline for Prescribing Opioids for Pain – United States, 2022, 71 MMWR Recomm. Rep. 1, Recommendation 3.  The Guideline also recommends when diagnosis and severity of acute pain warrant the use of opioids, clinicians should prescribe immediate-release opioids instead of extended-release and long-acting opioids at the lowest effective doses and for no longer than the expected duration of pain severe enough to require opioids to minimize the initiation of long-term opioid use.  Id., Recommendation 1.  However, the 2022 Clinical Practice Guideline, which updated the CDC’s 2016 Guideline, notes that its “recommendations are voluntary and intended to be flexible to support, not supplant, individualized, patient-centered care.”  Id. at Background.

The second “unresolvable” red flag alleged by DEA and shared by our reader was patients continuing to pay cash after the pharmacy filled their second prescription.  While certain circumstances surrounding a patient paying cash for controlled medication may be a prescribing/dispensing red flag, we cannot help but think that there are many legitimate reasons for patients paying cash for it to be patently “unresolvable” after their second fill.