Opiates: Use, Abuse, and Detection
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1 piates: Use, Abuse, and Detection Dr. Leo Kadehjian Palo Alto, California Abused Prescription Drugs pioids CS Depressants Morphine, codeine, etc. xycodone (xycontin) Buprenorphine Methadone entanyl Meperidine Propoxyphene Benzodiazepines on-benzos Barbiturates TC Ephedrine, etc. Dextromethorphan Antihistamines Stimulants Cocaine Amphetamine Methamphetamine Methylphenidate ther Carisoprodol Ketamine Steroids United States Drug Consumption 4.6% of world population Consumes 2/3 of illicit drug supply Consumes 8% of global opioid supply Consumes 99% of global hydrocodone supply L. Manchikanti and A. Singh, 28 1
2 Millions 6 on-medical Use of Drugs Prescription pioids Cocaine Methamphetamine Heroin SDUH, 21 xycodone per Capita DEA 213 xycodone Production Quota: 135, kg 211 U.S. Population: 311,591, , kg 311,591,917 persons = 422 mg/person! etail Sales of pioids (millions of grams) mg/person 329 mg/person +347% Ç HÅ Ç H xycodone +732% Hydrocodone +244% (#1 prescribed drug in U.S.) Codeine -25% Morphine +196% Methadone +1177% Meperidine -28% Å Hydromorphone +274% É É entanyl +479% www. deadiversion.usdoj.gov 2
3 6 5 % increase Increase in Abuse of Controlled Drugs + 542% ew teenager opioid abuse % 12 to 17 yr. olds abusing + 15% Prescriptions + 81% Adults abusing + 14% U.S. Population L. Manchikanti, Past Year Illicit Drug Use Thousands Marijuana 2 15 Psychotherapeutic 1 5 Cocaine H H H H H H H H H H L. Manchikanti, 26 Admitted Drug Abuse Millions Prescription Cocaine Hallucinogens Inhalants Heroin CASA, Under the Counter:, 25 3
4 6 Millions on-medical Use of Prescription Drugs Pain relievers Tranquilizers Stimulants Sedatives SDUH, 27 Past Year Initiates in Illicit Drug Use Thousands Pain relievers Marijuana É É É É É H H H H H É H É H Tranquilizers É É É Cocaine H H H Stimulants Ç Ç Ç Ç Ç Ç Ç Ç Ç Ç Sedatives Heroin L. Manchikanti, 26 6 ED Visits Drug Abuse Warning etwork, 25 4
5 H H H H H H H Morphine Hydromorphone (Dilaudid) xymorphone (umorphan) Dihydromorphine H 3 C H 3 C H 3 C H 3 C H Codeine H H Hydrocodone xycodone Dihydrocodeine (Vicodin, Lortab) (Percodan, xycontin) (Synalgos) H H 3 C H Morphine H Codeine Heroin H H 3 C Levorphanol Dextromethorphan H H H Morphine H 3 C H Buprenorphine H H altrexone evia, Vivitrol Methadone 5
6 piates: History 5 BC Sumerians Plant of joy" 4 BC Pain reliever (Hippocrates, Galen, Dioscorides) 153 Paracelsus mixes opium with alcohol ( laudanum ) 17s 1st modern anti-drug laws, China, against opium 183 Morphine isolated ( Morpheus ) 1822 De Quincey Confessions of an English pium Eater 1832 Codeine isolated 1839, 56 pium Wars (Hong Kong ceded to British) piates: History 1853 Hypodermic syringe invented Civil War, 4, addicts ( soldier s disease ) 1874 Diacetylmorphine synthesized 1875 S.. ban on opium houses (1st US drug law) 1898 Bayer markets Heroin (from heroisch ), as non-addictive alternative to morphine!!!??? (same year as aspirin) 196 U.S. Pure ood and Drug Act, labelling requirements 199 pium Exclusion Act, no importation International pium Commission, Shanghai piates: History 1914 Harrison arcotic Act, heroin controlled (<1 mg/g) 1923 Morphine structure 1924 Heroin Act, heroin illegal 1937 Methadone synthesized 1938 Meperidine (Demerol) introduced 195s 197s Morphine total synthesis piate receptors discovered Enkephalins, endorphins, discovered 6
7 piates: History 1993 Morphine µ-receptor sequenced, cloned 199s Heroin trials: Switzerland, several other countries ng/ml Urine Morphine after Poppy Seed Consumption n=9 poppy seeds: morphine content: 152 µg/g morphine intake: mg codeine levels: 6 82 ng/ml Hr M. Thevis et al., 23 piate Testing Cut-offs (ng/ml) SAMHSA Previous 12/98 DoD Initial Confirmation Morphine Codeine 6-MAM
8 esolution of piate Positives: Poppy Seeds or ot? Examine claimed consumption (positives unlikely for >1 day) Eliminate seeds from diet, collect another specimen after 3 days Test for 6-monoacetylmorphine (presence proves heroin use) Measure total morphine levels (>5 ng/ml unlikely for seeds) Measure morphine/codeine ratio (morphine > codeine for seeds) Look for evidence of opiate use (needle tracks, needles, behavior) H 3 C H H 3 C Heroin t 1/2 : 2 8 min H H Morphine t 1/2 : 4 hr H 3 C 6 Monoacetylmorphine t 1/2 : 1 2 min AM ng/ml Heroin, 12 mg i.v Hr. M. Smith et al., 21 8
9 Total Morphine, 6-AM after Heroin Dosing Lower dosing (3 7 mg) Total morphine: 1,392 9,25 ng/ml (median 3,62) 6-AM: ng/ml (median 16) Detection 1 ng/ml: 5.1 hr (median 2.3) Higher dosing ( mg) Total morphine: 2,65 29,3 ng/ml (median 16,47) 6-AM: ng/ml (median 242) Detection 1 ng/ml: hr (median 4.5) M. Smith et al., 21 6-AM After Heroin Dosing (3, 6 mg) 6-AM (ng/ml) 25 2 n = 6 t = 2 8 hr Total morphine (ng/ml) Cone et al., AM in Morphine Specimens >5 ng/ml AM (ng/ml) n = Total morphine (ng/ml) eal and Poklis,
10 Cross-eactivity piate assay 6-AM assay 3 ng/ml 2, ng/ml 1 ng/ml 6-Acetylmorphine 435 2,1 1 Morphine 3 2, 1, Morphine-3-glucuronide 626 6,167 6, Morphine-6-glucuronide 6, Codeine ,98 5, Dihydrocodeine 291 1,872 5, Hydromorphone 498 5,349 1, Hydrocodone 247 1,545 3, xymorphone 9,3 >1, 8, xycodone 1,5 23, 4, xycodone Effects: analgesia, euphoria, sedation, miosis (pupil constriction) Adverse effects: nausea, constipation, respiratory depression, hypotension, tolerance, withdrawal High oral bioavailability: 6% (vs. 2 3% for morphine) t 1/2 = 5 hr (vs hr for morphine) Metabolism/Elimination: xycodone, oxymorphone, and noroxycodone; conjugates xycontin 1996 Slow-release form of oxycodone (1915) Schedule II controlled substance 1 16 mg tablets (Purdue Pharma) Street price: $1/mg = 1x prescription cost Dosing: initial 1 mg/12 hr (vs. 1 3 mg/4 hr for oxycodone) Potency: 6x more potent than codeine equipotent to morphine and hydrocodone (Vicodin) 1/4 potency of hydromorphone (Dilaudid) 1x more potent than meperidine (Demerol) DAW: 3 4K mentions for oxycodone (3 5x morphine) 1
11 xycodone Metabolism and Elimination H H 3 C H H 3 C xymorphone H 13 14% conjugated 86 1% cross-reactivity xycodone 13 19% free 7 29% conjugated oroxycodone H major H Urine Concentrations of xycodone xycodone, ng/ml n = 2 5 mg oral 64 and 4 ( 24 hr) Baselt and Stewart, mg im n = 9 ~5 1, ( 24 hr) Poyhia et al., mg oral n = 2 1 mg im 2 mg im 2,5 and 75 (5 9 hr) 2,5 1, ( 3 9 hr) 6 8 (2 9 hr) Smith et al., 1995 n = 1 7 mg/day! 12, 9 Weinstein and Gaylord, 1979 H H H 3 C H H H aloxone Buprenorphine H Morphine 11
12 Buprenorphine (Subutex, Suboxone) Partial µ-opioid receptor agonist (strong binding, weak effects!-opioid receptor antagonist Combined with naloxone (Suboxone) to minimize abuse 25 4x more potent analgesic than morphine educed physical dependence, reduced respiratory depression Drug Addiction Treatment Act of 2 (Pub. L ) DA approval 1/8/2 (Schedule III) Buprenorphine (Subutex, Suboxone) Dosing: Addiction treatment mg/d (sublingual) Pain: <1 mg Therapeutic urine concentrations: Addiction treatment: few to several hundred ng/ml Pain: 4 6 ng/ml Bup, 6 26 ng/ml or Abusers: few to several hundred ng/ml or more atal overdoses: 4 1, ng/ml 3,4 ng/ml Bup, 6 or Assay cutoff: 5 ng/ml Sensitivity:.7 ng/ml Good 3 ng/ml Glucuronidation Buprenorphine Metabolism and Elimination H Hydroxylation (minor) Dealkylation H H H 3 C H Hydroxylation (minor) H 3 C Buprenorphine orbuprenorphine active 1%, mostly conjugated 14%, mostly conjugated 2/3 in feces 1/3 in urine H 12
13 # Urine Buprenorphine in Suboxone Patients 7 patients, 8 24 mg/d n=216 specimens for n=176 unadulterated avg. 164 ng/ml 2 1 < M. Hull et al., , ng/ml (LC/MS/MS) 1,-1,4 1,4-1, >1, Abuse Supra-therapeutic use, misuse Therapeutic use Concentration Pharmacokinetics Pharmacodynamics Dose Blood eceptors Effects Absorption Distribution Metabolism Elimination Urine, sweat, oral fluid, hair, 13
14 Urine Drug Concentrations (ng/ml): 1,922 Chronic Pain Patients Mean Median ange Amphetamine 1,163 3, ,372 Methamphetamine 15,674 1, ,591 xycodone xymorphone Hydrocodone Hydromorphone Methadone 7,599 2, ,9 4,93 1, ,36 2,953 1, ,2 1, ,526 4,167 2, ,322 Meperidine ormeperidine 3,86 3,49 1, ,216 1, ,98 E. Cone et al., 28 Assay response Positive sample Cut-off egative sample Estimated concentration Cut-off Estimated concentration egative does T mean o drug 14
15 µ-pioid eceptor Genotype and altrexone esponse 1% 9% 8% 7% 6% 5% 4% 3% 2% 1% % % With good clinical outcome Placebo altrexone Asn4 Asp4. Anton et al., 28 esources on Prescription Drug Abuse ational Institute on Drug Abuse (IDA), www. drugabuse.gov/drugpages/prescription.html ational Survey on Drug Use and Health (SDUH), Monitoring the uture, Drug Abuse Warning etwork (DAW) Treatment Episode Data Set (TEDS) Community Epidemiology Working Group (CEWG), Medline (PubMed), 15
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