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(12) United States Patent (10) Patent No.: US 8,906,413 B2 Chang Et Al

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(12) United States Patent (10) Patent No.: US 8,906,413 B2 Chang Et Al USOO8906413B2 (12) United States Patent (10) Patent No.: US 8,906,413 B2 Chang et al. (45) Date of Patent: Dec. 9, 2014 (54) DRUG FORMULATIONS HAVING REDUCED (56) References Cited ABUSE POTENTIAL U.S. PATENT DOCUMENTS (75) Inventors: Rong-Kun Chang, Rockville, MD (US); 3,079,303 A 2f1963 Raffet al. 3,383,283 A * 5, 1968 Brindamour .................. 424/490 Richard A. Couch, Chevy Chase, MD 4,070,494 A 1/1978 Hoffmeister et al. ............. 424.2 (US); Beth A. Burnside, Bethesda, MD 4,401,672 A 8/1983 Portoghese ... ... 424,260 (US) 4,457.933 A 7/1984 Gordon et al. ... 424,260 4,834,965 A 5/1989 Martani et al. 5,162.341 A 1 1/1992 Cook ............................ 514,317 (73) Assignee: Supernus Pharmaceuticals, Inc., 5,236,714 A 8/1993 Lee et al. ...................... 424/449 Rockville, MD (US) (Continued) (*) Notice: Subject to any disclaimer, the term of this FOREIGN PATENT DOCUMENTS patent is extended or adjusted under 35 EP 1382.331 A1 1, 2004 U.S.C. 154(b) by 1073 days. OTHER PUBLICATIONS (21) Appl. No.: 10/435,597 Non-Final Office Action mailed on Apr. 7, 2009 in U.S. Appl. No. 1 1/250,309, 11 pages. Matschiner et al. “Characterization of ion pair formation between (22) Filed: May 12, 2003 erythromycin and lipophilic counter ions.” Pharmazie, 1995, vol. 50. pp. 462-464. (65) Prior Publication Data (Continued) US 2004/02288O2A1 Nov. 18, 2004 Primary Examiner — Lakshmi Channavaljala (74) Attorney, Agent, or Firm — Foley & Lardner LLP; Sunit Talapatra (51) Int. C. (57) ABSTRACT A6K9/20 (2006.01) Drug formulations having reduced abuse potential which A 6LX 9/50 (2006.01) contain one or more of (1) a bittering agent, (2) a bright A 6LX 9/70 (2006.01) deterrent/indicator dye and (3) fine insoluble particulate mat A6 IK3I/00 (2006.01) ter. The bittering agent and dye are in a form which does not A61 K9/28 (2006.01) affect proper administration of the drug, but the bittering (52) U.S. C. agent creates a bitter side effect when the dosage form is CPC ............. A61K 9/7061 (2013.01); A61 K9/5078 crushed or chemically extracted and nasally, orally, buccally (2013.01); A61 K9/205 (2013.01); A61 K9/2013 or Sublingually administered and the dye produces a bright (2013.01); A61 K9/7069 (2013.01); A61 K color when crushed and contacted. The fine insoluble particu 31/00 (2013.01); A61 K9/2846 (2013.01); A61 K late matter hinders extraction of the drug from the dosage 9/5084 (2013.01); A61 K9/2018 (2013.01) form and, when crushed, can deter intravenous injection USPC ............ 424/489: 424/451; 424/464; 424/490 because of the presence of the insoluble particles or hinder (58) Field of Classification Search injection by blocking an intravenous needle. The bright color CPC. A61K 9/167; A61 K9/1676; A61K9/5078; of the dye, when extracted, also has a psychologically deter A61K9/5073; A61K31/485 rent effect on intravenous abusers. See application file for complete search history. 23 Claims, 1 Drawing Sheet Mean Dissolution Profiles for examples 4, 5, and 6 20 1. pH1. pH 6.0: ph 7.5 mm a - 100 - - - - - - s O - -- m . - - - - - - - - - w M - - - - - M - Example 4 - . ... -- - - - - - - - - - - - - - - - - - - e. Example 5 20 -----3. I-A-/-------------------------------- - Example 6B - - --Example 6A - - - O -- 2 4. s 8 10 12 4. 8 18 20 22 24 Time (hours) US 8,906.413 B2 Page 2 (56) References Cited OTHER PUBLICATIONS Rao et al., “Effect of Sodium Lauryl Sulfate on the Release of U.S. PATENT DOCUMENTS Rifampicin from guar gum Matrix. Indian Journal of Pharmaceuti cal Sciences, Sep.-Oct. 2000, pp. 404–406. 5,958.458 A 9/1999 Norling et al. Wells et al., “Effect of Anionic Surfactants on the Release of 6,124,282 A 9/2000 Sellers et al. .............. 514,227.5 Chlorpheniramine Maleate from an Inert, Heterogeneous Matrix.” 6,159,501 A 12/2000 Skinho Drug Development and Industrial Pharmacy, 1992, vol. 18, No. 2, pp. 6,187,341 B1 2/2001 Johnson et al. ............... 424/480 175-186. 6,228,863 B1 5/2001 Palermo et al. ............... 514,282 El-Kheshern, S. et al. “Coating charcoal with polyacrylate polymethacrylate copolymer for haemoperfusion III: The Effect of 6,277,384 B1 8/2001 Kaiko et al. ... 424/400 the Coat thickness on the adsorption capacity of the coated charcoal 7,141,250 B2 11/2006 Oshlack et al. ............... 424/490 and it's adsorption to small and middle size molecules' J. 7,214,385 B2 5, 2007 Gruber .......................... 424/451 Microencapsulation, 1995, vol. 12, No. 5, pp. 505-514. 2003, OO64O99 Al 4/2003 Oshlack et al. ............... 424/465 Final Office Action in U.S. Appl. No. 1 1/250,309 dated Sep. 24, 2003, OO64122 A1 4/2003 Goldberg et al. 2012. 2003/009 1635 A1 5, 2003 Baichwal et al. 2006, 0083690 A1 4/2006 Chang * cited by examiner U.S. Patent Dec. 9, 2014 US 8,906.413 B2 peAOSSO ue).8 US 8,906,413 B2 1. 2 DRUG FORMULATIONS HAVING REDUCED hostility or paranoia. Additionally, taking high doses of ABUSE POTENTIAL stimulants may result in dangerously high body temperatures and an irregular heartbeat. FIELD OF THE INVENTION Abuse potential of these three classes of drugs is of major concern. This is specially true for opioids and stimulants and This invention relates to dosage forms of prescription psy hence they are classified by the Drug Enforcement Agency choactive drug formulations having a reduced potential for (DEA) as Schedule II drugs (substances that have a high abuse and to methods of reducing the potential for abuse of potential for abuse with severe liability to cause psychic or dosage forms of prescription psychoactive drugs. physical dependence, but have some approved medical use). 10 Various dosage forms of psychoactive drugs for medical BACKGROUND OF THE INVENTION use are available or possible. These include capsules, tablets, transdermal patches and liquid Suspensions. For example, Prescription psychoactive drugs can help patients manage methylphenidate (Ritalin) is available in oral, tablet and chronic or severe pain, restore emotional or behavioral bal 15 extended-release tablet dosage forms. Dextroamphetamine ance, control sleep disorders, or fight obesity. When such (Adderall) is available in immediate-release tablet and prescription medications are abused, however, the conse extended-release capsule dosage forms. Methylphenidate, quences, including addiction, can be dangerous, even deadly. amphetamine, fentanyl, 3-methyl fentanyl, morphine, etor The risks associated with abuse of three classes of commonly phine, etc. can be incorporated into transdermal patches. A abused prescription drugs, i.e., opioids; central nervous sys fentanyl patch (Duragesic) is already in the marketplace and tem (CNS) depressants, including sedatives and tranquilizers; a methylphenidate patch (Methypatch) is under FDA review. and stimulants, are well documented. Liquid Suspensions of drugs in immediate release and Sus Opioids include morphine, codeine, and related drugs such tained release forms are also possible. A Sustained release as oxycodone (Percodan and OxyContin), hydrocodone (Vi system can be formulated by using drug ion-exchange com codin), and meperidine (Demerol) and are commonly pre 25 plex particles with a further coating of ethyl cellulose. The scribed to relieve pain. Taken as prescribed, opioids can be ion-exchange technology makes reliable liquid controlled used to manage pain effectively without unwanted side release possible for many ionic drugs, which include amphet effects. Chronic use of opioids can result in tolerance, which amine, methylphenidate, hydrocodone, codeine, morphine, means that users must take higher doses to achieve the same and the like. effects. Long-term use also can lead to physical dependence 30 These various dosage forms provide valuable medical ben and addiction. Withdrawal can occur when an individual dis efits when properly taken or administered, but also have a continues use of the drugs. Withdrawal symptoms can include high potential for abuse. For example, Sustained release dos restlessness, muscle and bone pain, insomnia, diarrhea, Vom age forms are abused by crushing or chewing and then Swal iting, cold flashes with goose humps, and involuntary leg lowing or Snorting or by mixing or dissolving in water or the movements. Individuals who are addicted to opioids are more 35 like and then injecting. Transdermal patches can be chewed to likely to overdose on the drugs, which could be fatal. provide a quick onset via buccal, Sublingual, or oral absorp Among the most commonly prescribed CNS depressants tion of the controlled Substances. In addition, a significant are barbiturates, such as mephobarbital (Mebaral) and pen drug residue after normal administration of the patches is tobarbital sodium (Nembutal), which are prescribed to treat 40 quite common. Such residue can be extracted and concen anxiety, tension, and sleep disorders; and benzodiazepines, trated for abuse. Liquid Suspensions can be similarly concen Such as diazepam (Valium) and alprazolam (Xanax), which trated and abused. typically are prescribed to treat anxiety, acute stress reactions, It view of these problems, new and improved dosage forms and panic attacks. Other benzodiazepines, such as triazolam of psychoactive drugs having decreased abuse potential are (Halcion) and estazolam (ProSom), are prescribed for short 45 desired. Several approaches to reducing the abuse potential of term treatment of sleep disorders. Although the various dosage forms of drugs can be found in U.S. patents. These classes of CNS depressants work differently, they all produce include, for example, the incorporation of an opioid antago a beneficial drowsy or calming effect in individuals suffering nist into a dosage form (U.S. Pat. Nos. 4,401,672, 4,457.933, from sleep disorders or anxiety. However, if one uses these 5,162.341, 5,236,714, 6,277.384 and 6.228,863), the use of drugs over a long period of time, the body will develop 50 cytochrome P450 2D6 enzyme inhibitor (U.S.
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