Hydrocodone
![]() | |
![]() | |
Clinical data | |
---|---|
Trade names | Hysingla ER, Zohydro ER |
Other names | Dihydrocodeinone, hydrocodone bitartrate |
AHFS/Drugs | Monograph |
MedlinePlus | a601006 |
License data | |
Dependence liability | High[1] |
Addiction liability | High |
Routes of administration | Clinical:by mouth[2] Others:intranasal,rectal |
Drug class | Opioid |
ATC code | |
Legal status | |
Legal status |
|
Pharmacokineticdata | |
Bioavailability | By mouth: 70%[4] |
Protein binding | Low[4][5] |
Metabolism | Liver:CYP3A4(major),CYP2D6(minor)[6] |
Metabolites | •Norhydrocodone[6] •Hydromorphone[6] • Others[6] |
Onset of action | 10–20 minutes[2] |
Eliminationhalf-life | Average: 3.8 hours[7] Range: 3.3–4.4 hours[2] |
Duration of action | 4–8 hours[2] |
Excretion | Urine[8][9] |
Identifiers | |
| |
CAS Number | |
PubChemCID | |
IUPHAR/BPS | |
DrugBank | |
ChemSpider | |
UNII | |
KEGG | |
ChEBI | |
ChEMBL | |
CompTox Dashboard(EPA) | |
ECHA InfoCard | 100.004.304 |
Chemical and physical data | |
Formula | C18H21NO3 |
Molar mass | 299.370g·mol−1 |
3D model (JSmol) | |
| |
| |
(verify) |
Hydrocodone,also known asdihydrocodeinone,is a semisyntheticopioidused to treatpainand as acough suppressant.[10]It is taken by mouth.[10]Typically it is dispensed as the combinationacetaminophen/hydrocodoneoribuprofen/hydrocodonefor pain severe enough to require an opioid[11][12][13]and in combination withhomatropine methylbromideto relieve cough.[10]It is also available by itself in a long-acting form under the brand name Zohydro ER, among others, to treat severe pain of a prolonged duration.[10][14]Hydrocodone is a controlled drug: in the United States aSchedule IIControlled Substance.
Side effects and mechanisms
[edit]Common side effects includedizziness,sleepiness, nausea, and constipation.[10]Serious side effects may includelow blood pressure,seizures,QT prolongation,respiratory depression,andserotonin syndrome.[10]Rapidly decreasing the dose may result inopioid withdrawal.[10]Use duringpregnancyorbreastfeedingis generally not recommended.[15]Hydrocodone is believed to work by activatingopioid receptors,mainly in the brain and spinal cord.[10]Hydrocodone 10 mg is equivalent to about 10 mg ofmorphineby mouth.[16]
History and culture
[edit]Hydrocodone was patented in 1923, while the long-acting formulation was approved for medical use in the United States in 2013.[10][17]It is most commonly prescribed in the United States, which consumed 99% of the worldwide supply as of 2010.[18]In 2018, it was the 402nd most commonly prescribed medication in the United States, with more than 400,000 prescriptions.[19]Hydrocodone is a semisynthetic opioid, converted fromcodeine[20][21]or less often fromthebaine.[22]Production using genetically engineered yeasts has been developed but is not used commercially.[23][24][25]
Medical uses
[edit]Hydrocodone is used to treat moderate to severe pain. In liquid formulations, it is used to treat cough.[10]In one study comparing the potency of hydrocodone to that ofoxycodone,it was found that it took 50% more hydrocodone to achieve the same degree of miosis (pupillary contraction).[26]The investigators interpreted this to mean that oxycodone is about 50% more potent than hydrocodone.
However, in a study ofemergency departmentpatients with fractures, it was found that an equal amount of either drug provided about the same degree of pain relief, indicating that there is little practical difference between them when used for that purpose.[27]Some references state that the analgesic action of hydrocodone begins in 20–30 minutes and lasts about 4–8 hours.[28]The manufacturer's information says onset of action is about 10–30 minutes and duration is about 4–6 hours.[29]Recommended dosing interval is 4–6 hours. Hydrocodone reaches peak serum levels after 1.3 hours.[30]
Available forms
[edit]Hydrocodone is available in a variety of formulations for oral administration:[31][32][33]
- The original oral form of hydrocodone alone, Dicodid, as immediate-release 5- and 10-mg tablets is available for prescription in Continental Europe per national drug control and prescription laws and Title 76 of the Schengen Treaty, butdihydrocodeinehas been more widely used for the same indications since the beginning in the early 1920s, with hydrocodone being regulated the same way asmorphinein the GermanBetäubungsmittelgesetz,the similarly named law in Switzerland and the AustrianSuchtmittelgesetz,whereas dihydrocodeine is regulated likecodeine.For a number of decades, the liquid hydrocodone products available have been cough medicines.
- Hydrocodone plushomatropine(Hycodan) in the form of small tablets for coughing and especially neuropathic moderate pain (the homatropine, an anticholinergic, is useful in both of those cases and is a deterrent to intentional overdose) was more widely used than Dicodid and was labelled as a cough medicine in the United States whilst Vicodin and similar drugs were the choices for analgesia.
- Extended-release hydrocodone in a time-release syrup also containing chlorphenamine/chlorpheniramineis a cough medicine called Tussionex in North America. In Europe, similar time-release syrups containing codeine (numerous), dihydrocodeine (Paracodin Retard Hustensaft), nicocodeine (Tusscodin),thebacon,acetyldihydrocodeine,dionine,andnicodicodeineare used instead.
- Immediate-release hydrocodone withparacetamol(acetaminophen) (Vicodin, Lortab, Lorcet, Maxidone, Norco, Zydone)
- Immediate-release hydrocodone withibuprofen(Vicoprofen, Ibudone, Reprexain)
- Immediate-release hydrocodone withaspirin(Alor 5/500, Azdone, Damason-P, Lortab ASA, Panasal 5/500)
- Controlled-release hydrocodone (Hysingla ER byPurdue Pharma,Zohydro ER)[34]
Hydrocodone is not available inparenteralor any other non-oral forms.[5][2]
Side effects
[edit]
Commonside effectsof hydrocodone arenausea,vomiting,constipation,drowsiness,dizziness,lightheadedness,anxiety,abnormally happy or sad mood, dry throat, difficultyurinating,rash,itching,and contraction of the pupils. Serious side effects include slowed or irregular breathing and chest tightness.[35]
Several cases of progressive bilateral hearing loss unresponsive to steroid therapy have been described as an infrequent adverse reaction to hydrocodone/paracetamol misuse. This adverse effect has been considered by some to be due to theototoxicityof hydrocodone.[36][37]Other researchers have suggested that paracetamol is the primary agent responsible for theototoxicity.[38][39]
The U.S.Food and Drug Administration(FDA) assigns the drug topregnancy categoryC, meaning that no adequate and well-controlled studies in humans have been conducted. A newborn of a mother taking opioid medications regularly prior to the birth will be physically dependent.[40][41]The baby may also exhibit respiratory depression if the opioid dose was high.[42]An epidemiological study indicated that opioid treatment during early pregnancy results in increased risk of various birth defects.[43]
Symptoms of hydrocodoneoverdoseinclude narrowed or widened pupils; slow, shallow, or stopped breathing; slowed or stopped heartbeat; cold, clammy, or blue skin; excessive sleepiness; loss of consciousness; seizures; or death.[35]
Hydrocodone can be habit forming, causing physical and psychological dependence. Its abuse liability is similar to morphine and less than oxycodone.[44]
Interactions
[edit]Hydrocodone ismetabolizedby thecytochrome P450enzymesCYP2D6andCYP3A4,andinhibitorsandinducersof these enzymes can modify hydrocodone exposure.[45]One study found that combination ofparoxetine,aselective serotonin reuptake inhibitor(SSRI) and strong CYP2D6 inhibitor, with once-daily extended-release hydrocodone, did not modify exposure to hydrocodone or the incidence of adverse effects.[45][46]These findings suggest that hydrocodone can be coadministered with CYP2D6 inhibitors without dosage modification.[45][46]Conversely, combination ofhydrocodone/acetaminophenwith theantiviralregimen ofombitasvir,paritaprevir,ritonavir,anddasabuvirfor treatment ofhepatitis Cincreasedpeak concentrationsof hydrocodone by 27%,total exposureby 90%, andelimination half-lifefrom 5.1hours to 8.0hours.[47]Ritonavir is a strong CYP3A4 inhibitor as well as inducer of CYP3A and other enzymes, and the other antivirals are known to inhibitdrug transporterslikeorganic anion transporting polypeptide(OATP)1B1and1B3,P-glycoprotein,andbreast cancer resistance protein(BCRP).[47]The changes in hydrocodone levels are consistent with CYP3A4 inhibition by ritonavir.[47]Based on these findings, a 50% lower dose of hydrocodone and closer clinical monitoring was recommended when hydrocodone is used in combination with this antiviral regimen.[47]
People consumingalcohol,other opioids,anticholinergicantihistamines,antipsychotics,anxiolytics,or othercentral nervous system(CNS)depressantstogether with hydrocodone may exhibit an additiveCNS depression.[42]Hydrocodone taken concomitantly withserotonergicmedications like SSRIantidepressantsmay increase the risk ofserotonin syndrome.[48]
Pharmacology
[edit]Pharmacodynamics
[edit]Compound | Affinities(Ki ) | Ratio | Ref | ||
---|---|---|---|---|---|
MOR | DOR | KOR | MOR:DOR:KOR | ||
Hydrocodone | 11.1 nM | 962 nM | 501 nM | 1:87:45 | [49] |
Hydromorphone | 0.47 nM | 18.5 nM | 24.9 nM | 1:39:53 | [50] |
Compound | Route | Dose |
---|---|---|
Codeine | PO | 200 mg |
Hydrocodone | PO | 20–30 mg |
Hydromorphone | PO | 7.5 mg |
Hydromorphone | IV | 1.5 mg |
Morphine | PO | 30 mg |
Morphine | IV | 10 mg |
Oxycodone | PO | 20 mg |
Oxycodone | IV | 10 mg |
Oxymorphone | PO | 10 mg |
Oxymorphone | IV | 1 mg |
Hydrocodone is a highlyselectivefull agonistof theμ-opioid receptor(MOR).[28][54][49]This is the mainbiological targetof theendogenousopioidneuropeptideβ-endorphin.[55]Hydrocodone has lowaffinityfor theδ-opioid receptor(DOR) and theκ-opioid receptor(KOR), where it is anagonistsimilarly.[49]
Studies have shown hydrocodone is stronger thancodeinebut only one-tenth as potent asmorphineat binding to receptors and reported to be only 59% as potent as morphine in analgesic properties. However, in tests conducted on rhesus monkeys, the analgesic potency of hydrocodone was actually higher than morphine.[7]Oralhydrocodone has a mean equivalent daily dosage (MEDD) factor of 0.4, meaning that 1 mg of hydrocodone is equivalent to 0.4 mg of intravenous morphine. However, because of morphine's loworal bioavailability,there is a 1:1 correspondence between orally administered morphine and orally administered hydrocodone.[56]
Pharmacokinetics
[edit]Absorption
[edit]Hydrocodone is only pharmaceutically available as anoralmedication.[2]It is well-absorbed,but the oralbioavailabilityof hydrocodone is only approximately 25%.[4][5]Theonset of actionof hydrocodone via this route is 10 to 20 minutes, with a peak effect (Tmax) occurring at 30 to 60 minutes,[51]and it has a duration of 4 to 8 hours.[2]The FDA label for immediate-release hydrocodone with acetaminophen does not include any information on the influence of food on its absorption or other pharmacokinetics.[57]Conversely, coadministration with a high-fat meal increases peak concentrations of different formulations of extended-release hydrocodone by 14 to 54%, whereasarea-under-the-curve levelsare not notably affected.[58][59][60][61]
Distribution
[edit]Thevolume of distributionof hydrocodone is 3.3 to 4.7 L/kg.[5]Theplasma protein bindingof hydrocodone is 20 to 50%.[28]
Metabolism
[edit]In theliver,hydrocodone is transformed into severalmetabolites,includingnorhydrocodone,hydromorphone,6α-hydrocodol(dihydrocodeine), and6β-hydrocodol.[6]6α- and 6β-hydromorphol are also formed, and the metabolites of hydrocodone are conjugated (viaglucuronidation).[62][63]Hydrocodone has aterminal half-lifethat averages 3.8 hours (range 3.3–4.4 hours).[7][2]The hepaticcytochrome P450enzymeCYP2D6converts hydrocodone into hydromorphone, a more potent opioid (5-fold higher binding affinity to the MOR).[6][64]However, extensive and poorcytochrome 450CYP2D6 metabolizers had similar physiological and subjective responses to hydrocodone, and CYP2D6 inhibitorquinidinedid not change the responses of extensive metabolizers, suggesting that inhibition of CYP2D6 metabolism of hydrocodone has no practical importance.[65][66]Ultra-rapid CYP2D6 metabolizers (1–2% of the population) may have an increased response to hydrocodone; however, hydrocodone metabolism in this population has not been studied.[67]
Norhydrocodone, the major metabolite of hydrocodone, is predominantly formed by CYP3A4-catalyzed oxidation.[6]In contrast to hydromorphone, it is described as inactive.[64]However, norhydrocodone is actually a MOR agonist with similar potency to hydrocodone, but has been found to produce only minimal analgesia when administered peripherally to animals (likely due to poorblood–brain barrierand thuscentral nervous systempenetration).[68]Inhibition of CYP3A4 in a child who was, in addition, a poor CYP2D6 metabolizer, resulted in a fatal overdose of hydrocodone.[69]Approximately 40% of hydrocodone metabolism is attributed to non-cytochrome P450-catalyzed reactions.[70]
Elimination
[edit]Hydrocodone isexcretedinurine,mainly in the form ofconjugates.[8][9]
Chemistry
[edit]Detection in body fluids
[edit]Hydrocodone concentrations are measured in blood, plasma, and urine to seek evidence of misuse, to confirm diagnoses of poisoning, and to assist in investigations into deaths. Many commercial opiate screening tests react indiscriminately with hydrocodone, other opiates, and their metabolites, but chromatographic techniques can easily distinguish hydrocodone uniquely. Blood and plasma hydrocodone concentrations typically fall into the 5–30 μg/L range among people taking the drug therapeutically, 100–200 μg/L among recreational users, and 100–1,600 μg/L in cases of acute, fatal overdosage. Co-administration of the drug with food or alcohol can very significantly increase the resulting plasma hydrocodone concentrations that are subsequently achieved.[71][72]
Synthesis
[edit]Hydrocodone is most commonly synthesized fromthebaine,a constituent of opium latex from the dried poppy plant. Once thebaine is obtained, the reaction undergoeshydrogenationusing a palladium catalyst.[73]
Structure
[edit]There are three important structures in hydrocodone: theamine group,which binds to the tertiary nitrogen binding site in the central nervous system'sopioid receptor,thehydroxy groupthat binds to the anionic binding side, and thephenyl groupwhich binds to the phenolic binding site.[74]This triggers a G protein activation and subsequent release ofdopamine.[75]
History
[edit]Hydrocodone was first synthesized in Germany in 1920 byCarl Mannichand Helene Löwenheim.[76]It was approved by theFood and Drug Administrationon 23 March 1943 for sale in the United States and approved byHealth Canadafor sale in Canada under the brand name Hycodan.[77][78]
Hydrocodone was first marketed by Knoll as Dicodid, starting in February 1924 in Germany. This name is analogous to other products the company introduced or otherwise marketed: Dilaudid (hydromorphone, 1926), Dinarkon (oxycodone, 1917), Dihydrin (dihydrocodeine, 1911), and Dimorphan (dihydromorphine). Paramorfan is the trade name of dihydromorphine from another manufacturer, as is Paracodin, for dihydrocodeine.[79][80]
The name Dicodid was registered in the United States and appears without a monograph as late as 1978 in thePhysicians' Desk Reference;Dicodid may have been marketed to one extent or another in North America in the 1920s and early 1930s. The drug was pure hydrocodone in small 5 and 10 mg tablets, physically similar to the Dilaudid tablets. It is no longer manufactured by Knoll in Germany, nor is a generic available. Hydrocodone was never as common in Europe as it is in North America—dihydrocodeine is used for its spectrum of indications. Germany was the number two consumer of hydrocodone until the manufacture of the drug was discontinued there. Now,[when?]the world outside the United States accounts for less than 1% of annual consumption. It was listed as aSuchtgiftunder the GermanBetäubungsmittelgesetzand regulated like morphine. It became available in theSchengen Areaof the European Union as of 1 January 2002 under Title 76 of the Schengen Treaty.[citation needed]
Society and culture
[edit]Formulations
[edit]Several common imprints for hydrocodone are M365, M366, M367.[81]
Combination products
[edit]![](https://upload.wikimedia.org/wikipedia/commons/thumb/b/bf/Hydrocodone-paracetamol-5-500.jpg/220px-Hydrocodone-paracetamol-5-500.jpg)
Most hydrocodone formulations include a second analgesic, such as paracetamol (acetaminophen) or ibuprofen. Examples of hydrocodone combinations include Norco, Vicodin, Vicoprofen and Riboxen.[82]
Legal status in the United States
[edit]The US government imposed tougher prescribing rules for hydrocodone in 2014, changing the drug fromSchedule IIItoSchedule II.[83][84][85][86]In 2011, hydrocodone products were involved in around 100,000 abuse-related emergency department visits in the United States, more than double the number in 2004.[87]
References
[edit]- ^Bonewit-West K, Hunt SA, Applegate E (2012).Today's Medical Assistant: Clinical and Administrative Procedures.Elsevier Health Sciences. p. 571.ISBN9781455701506.Archivedfrom the original on 10 January 2023.Retrieved20 August2019.
- ^abcdefghElliott JA (19 April 2016)."Opioids in the management of acute pain".In Elliott JA, Smith HS (eds.).Handbook of Acute Pain Management.CRC Press. pp. 79–.ISBN978-1-4665-9635-1.
- ^Anvisa(31 March 2023)."RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial"[Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese).Diário Oficial da União(published 4 April 2023).Archivedfrom the original on 3 August 2023.Retrieved16 August2023.
- ^abcPolsten GR, Wallace MS (21 June 2016)."Analgesic Agents in Rheumatic Disease".In Firestein GS, Budd R, Gabriel SE, McInnes IB, O'Dell JR (eds.).Kelley and Firestein's Textbook of Rheumatology.Elsevier Health Sciences. pp. 1081–.ISBN978-0-323-41494-4.Archivedfrom the original on 12 January 2023.Retrieved23 September2016.
- ^abcdChabner BA, Longo DL (8 November 2010)."Chapter 37: Drug Therapy of Pain in Cancer Patients".Cancer Chemotherapy and Biotherapy: Principles and Practice.Lippincott Williams & Wilkins. pp. 700–.ISBN978-1-60547-431-1.Archivedfrom the original on 12 January 2023.Retrieved23 September2016.
- ^abcdefgZhou S (6 April 2016)."Substrates of Human CYP2D6: Opioids and Opioid Receptor Antagonists".Cytochrome P450 2D6: Structure, Function, Regulation and Polymorphism.CRC Press. pp. 164–.ISBN978-1-4665-9788-4.
- ^abcDavis MP, Glare P, Hardy J (2005).Opioids in Cancer Pain.Oxford University Press. pp. 59–68.ISBN978-0-19-852943-9.
- ^abBluth MH (16 November 2016).Toxicology and Drug Testing, An Issue of Clinics in Laboratory Medicine, E-Book.Elsevier Health Sciences. pp. 85–.ISBN978-0-323-47795-6.Archivedfrom the original on 12 January 2023.Retrieved22 June2018.
- ^abSmith HS (21 February 2013).Opioid Therapy in the 21st Century.OUP USA. pp. 68–.ISBN978-0-19-984497-5.Archivedfrom the original on 12 January 2023.Retrieved22 June2018.
- ^abcdefghij"Hydrocodone Bitartrate Monograph for Professionals".Drugs.American Society of Health-System Pharmacists.Archivedfrom the original on 14 November 2010.Retrieved15 April2019.
- ^Mallinckrodt (10 March 2021)."HYDROCODONE BITARTRATE AND ACETAMINOPHEN tablet (label)".National Institutes of Health DailyMed.Archivedfrom the original on 6 November 2021.Retrieved6 November2021.
- ^Briggs GG, Freeman RK, Yaffe SJ (2011).Drugs in Pregnancy and Lactation: A Reference Guide to Fetal and Neonatal Risk.Lippincott Williams & Wilkins. p. 692.ISBN9781608317080.
- ^"Hydrocodone Combination Products: MedlinePlus Drug Information".medlineplus.gov.Archivedfrom the original on 5 July 2016.Retrieved4 November2023.
- ^"Hydrocodone: MedlinePlus Drug Information".medlineplus.gov.Archivedfrom the original on 15 April 2019.Retrieved15 April2019.
- ^"Hydrocodone Use During Pregnancy".Drugs.Archivedfrom the original on 28 January 2014.Retrieved15 April2019.
- ^"Opioid Dose Calculator".Agency Medical Directors' Group.Archived fromthe originalon 10 February 2016.Retrieved15 April2019.
- ^Fischer J, Ganellin CR (2006).Analogue-based Drug Discovery.John Wiley & Sons. p. 526.ISBN9783527607495.Archivedfrom the original on 14 January 2023.Retrieved25 August2020.
- ^"Making Some Painkillers Harder to Get".The New York Times.21 February 2013.Archivedfrom the original on 3 January 2022.Retrieved15 April2019.
- ^"Hydrocodone - Drug Usage Statistics".ClinCalc.Archivedfrom the original on 13 November 2022.Retrieved7 October2022.
- ^Stoker HS (2012).General, Organic, and Biological Chemistry.Cengage Learning. p. 567.ISBN9781133711285.
- ^Vardanyan R, Hruby V (10 March 2006).Synthesis of Essential Drugs.Elsevier.ISBN978-0-08-046212-7.
- ^Narcotic Drugs 2020, Estimated World Requirements for 2021, Statistics for 2019(PDF).International Narcotics Control Board. 2020. p. 37.ISBN978-92-1-148355-0.Archived(PDF)from the original on 3 November 2021.Retrieved12 December2021.
Thebaine itself is not used in therapy, but it is an important starting material for the manufacture of a number of opioids, mainly codeine, dihydrocodeine, etorphine, hydrocodone, oxycodone and oxymorphone...
- ^Galanie S, Thodey K, Trenchard IJ, Filsinger Interrante M, Smolke CD (September 2015)."Complete biosynthesis of opioids in yeast".Science.349(6252): 1095–1100.Bibcode:2015Sci...349.1095G.doi:10.1126/science.aac9373.PMC4924617.PMID26272907.
- ^Thodey K, Galanie S, Smolke CD (October 2014)."A microbial biomanufacturing platform for natural and semisynthetic opioids".Nature Chemical Biology.10(10): 837–844.doi:10.1038/nchembio.1613.PMC4167936.PMID25151135.
- ^Nakagawa A, Matsumura E, Koyanagi T, Katayama T, Kawano N, Yoshimatsu K, et al. (February 2016)."Total biosynthesis of opiates by stepwise fermentation using engineered Escherichia coli".Nature Communications.7(1): 10390.Bibcode:2016NatCo...710390N.doi:10.1038/ncomms10390.PMC4748248.PMID26847395.
{{cite journal}}
:CS1 maint: overridden setting (link) - ^Zacny JP, Gutierrez S (April 2009)."Within-subject comparison of the psychopharmacological profiles of oral hydrocodone and oxycodone combination products in non-drug-abusing volunteers".Drug and Alcohol Dependence.101(1–2): 107–114.doi:10.1016/j.drugalcdep.2008.11.013.PMID19118954.Archivedfrom the original on 18 January 2021.Retrieved25 August2020.
- ^Marco CA, Plewa MC, Buderer N, Black C, Roberts A (April 2005)."Comparison of oxycodone and hydrocodone for the treatment of acute pain associated with fractures: a double-blind, randomized, controlled trial".Academic Emergency Medicine.12(4): 282–288.doi:10.1197/j.aem.2004.12.005.PMID15805317.
- ^abcVallejo R, Barkin RL, Wang VC (2011)."Pharmacology of opioids in the treatment of chronic pain syndromes".Pain Physician.14(4): E343–E360.doi:10.36076/ppj.2011/14/E343.PMID21785485.
- ^"Opioid (Narcotic Analgesics and Acetaminophen Systemic )".Archived fromthe originalon 22 March 2014.Retrieved22 March2014.
- ^"Labeling-Package Insert: Hydrocodone/acetaminophen 7.5 mg/325 mg"(PDF).Drugs@FDA: FDA-Approved Drugs.Chartwell. 18 October 2013.Archived(PDF)from the original on 27 April 2024.Retrieved22 January2024.
- ^McPherson ML (24 August 2009)."Appendix: Opioid Formulations".Demystifying Opioid Conversion Calculations: A Guide for Effective Dosing.ASHP. pp. 187–188.ISBN978-1-58528-297-5.Archivedfrom the original on 12 January 2023.Retrieved23 September2016.
- ^Odom-Forren J, Drain C (11 February 2008).PeriAnesthesia Nursing: A Critical Care Approach.Elsevier Health Sciences. pp. 751–.ISBN978-1-4377-2610-7.Archivedfrom the original on 12 January 2023.Retrieved23 September2016.
- ^Skidmore-Roth L (27 June 2013)."Hydrocodone".Mosby's Drug Guide for Nursing Students, with 2014 Update.Elsevier Health Sciences. pp. 524–.ISBN978-0-323-22268-6.Archivedfrom the original on 12 January 2023.Retrieved23 September2016.
- ^Vadivelu N, Schermer E, Kodumudi G, Berger JM (July 2016). "The Clinical Applications of Extended-Release Abuse-Deterrent Opioids".CNS Drugs.30(7): 637–646.doi:10.1007/s40263-016-0357-0.PMID27290716.S2CID26878027.
- ^ab"Hydrocodone Combination Products".MedlinePlus.U.S. National Library of Medicine. 1 October 2008.Archivedfrom the original on 5 July 2016.Retrieved20 April2013.
- ^Friedman RA, House JW, Luxford WM, Gherini S, Mills D (March 2000). "Profound hearing loss associated with hydrocodone/acetaminophen abuse".The American Journal of Otology.21(2): 188–191.doi:10.1016/S0196-0709(00)80007-1.PMID10733182.
- ^Ho T, Vrabec JT, Burton AW (May 2007)."Hydrocodone use and sensorineural hearing loss".Pain Physician.10(3): 467–472.PMID17525781.Archived fromthe originalon 23 July 2011.
- ^Yorgason JG, Kalinec GM, Luxford WM, Warren FM, Kalinec F (June 2010). "Acetaminophen ototoxicity after acetaminophen/hydrocodone abuse: evidence from two parallel in vitro mouse models".Otolaryngology–Head and Neck Surgery.142(6): 814–9, 819.e1–2.doi:10.1016/j.otohns.2010.01.010.PMID20493351.S2CID25083914.
- ^Curhan SG, Eavey R, Shargorodsky J, Curhan GC (March 2010)."Analgesic use and the risk of hearing loss in men".The American Journal of Medicine.123(3): 231–237.doi:10.1016/j.amjmed.2009.08.006.PMC2831770.PMID20193831.
- ^"Neonatal abstinence syndrome: MedlinePlus Medical Encyclopedia".medlineplus.gov.Archivedfrom the original on 28 July 2017.Retrieved11 January2022.
- ^"Opioid Use and Opioid Use Disorder in Pregnancy".acog.org.Archivedfrom the original on 11 January 2022.Retrieved11 January2022.
- ^ab"REPREXAIN (hydrocodone bitartrate, ibuprofen) tablet, film coated".dailymed.nlm.nih.gov.NIH.Archivedfrom the original on 6 July 2013.Retrieved27 April2013.
- ^Broussard CS, Rasmussen SA, Reefhuis J, Friedman JM, Jann MW, Riehle-Colarusso T, et al. (April 2011)."Maternal treatment with opioid analgesics and risk for birth defects".American Journal of Obstetrics and Gynecology.204(4): 314.e1–314.11.doi:10.1016/j.ajog.2010.12.039.PMID21345403.
- ^Wightman R, Perrone J, Portelli I, Nelson L (December 2012)."Likeability and abuse liability of commonly prescribed opioids".Journal of Medical Toxicology.8(4): 335–340.doi:10.1007/s13181-012-0263-x.PMC3550270.PMID22992943.
- ^abcFeng XQ, Zhu LL, Zhou Q (2017)."Opioid analgesics-related pharmacokinetic drug interactions: from the perspectives of evidence based on randomized controlled trials and clinical risk management".Journal of Pain Research.10:1225–1239.doi:10.2147/JPR.S138698.PMC5449157.PMID28579821.
- ^abKapil RP, Friedman K, Cipriano A, Michels G, Shet M, Mondal SA, et al. (October 2015)."Effects of paroxetine, a CYP2D6 inhibitor, on the pharmacokinetic properties of hydrocodone after coadministration with a single-entity, once-daily, extended-release hydrocodone tablet".Clinical Therapeutics.37(10): 2286–2296.doi:10.1016/j.clinthera.2015.08.007.PMID26350273.
- ^abcdPolepally AR, King JR, Ding B, Shuster DL, Dumas EO, Khatri A, et al. (August 2016)."Drug-Drug Interactions Between the Anti-Hepatitis C Virus 3D Regimen of Ombitasvir, Paritaprevir/Ritonavir, and Dasabuvir and Eight Commonly Used Medications in Healthy Volunteers".Clinical Pharmacokinetics.55(8): 1003–1014.doi:10.1007/s40262-016-0373-8.PMC4933729.PMID26895022.
{{cite journal}}
:CS1 maint: overridden setting (link) - ^Gnanadesigan N, Espinoza RT, Smith RL (June 2005). "The serotonin syndrome".The New England Journal of Medicine.352(23): 2454–6, author reply 2454–6.doi:10.1056/NEJM200506093522320.PMID15948273.
- ^abcCodd EE, Shank RP, Schupsky JJ, Raffa RB (September 1995)."Serotonin and norepinephrine uptake inhibiting activity of centrally acting analgesics: structural determinants and role in antinociception".The Journal of Pharmacology and Experimental Therapeutics.274(3): 1263–1270.PMID7562497.Archivedfrom the original on 2 February 2017.Retrieved21 June2018.
- ^Filizola M, Villar HO, Loew GH (January 2001). "Molecular determinants of non-specific recognition of delta, mu, and kappa opioid receptors".Bioorganic & Medicinal Chemistry.9(1): 69–76.doi:10.1016/S0968-0896(00)00223-6.PMID11197347.
- ^abKing TL, Miller EL (25 October 2010)."Analgesia and Anesthesia".In King TL, Brucker MC (eds.).Pharmacology for Women's Health.Jones & Bartlett Publishers. pp. 332–.ISBN978-1-4496-1073-9.
- ^Parker RK, Hepner D, Eappin S (28 February 2014)."Chapter 27 Postoperative and Chronic Pain: Systemic and Regional Analgesic Techniques".In Chestnut DH, Wong CA, Tsen LC, Kee WD, Beilin Y, Mhyre J (eds.).Chestnut's Obstetric Anesthesia: Principles and Practice E-Book.Elsevier Health Sciences. pp. 611–.ISBN978-0-323-11374-8.Archivedfrom the original on 11 January 2023.Retrieved22 June2018.
- ^Tiziani AP (1 June 2013)."Opiod Analgesics".Havard's Nursing Guide to Drugs.Elsevier Health Sciences. pp. 933–.ISBN978-0-7295-8162-2.Archivedfrom the original on 11 January 2023.Retrieved22 June2018.
- ^Thompson CM, Wojno H, Greiner E, May EL, Rice KC, Selley DE (February 2004). "Activation of G-proteins by morphine and codeine congeners: insights to the relevance of O- and N-demethylated metabolites at mu- and delta-opioid receptors".The Journal of Pharmacology and Experimental Therapeutics.308(2): 547–554.doi:10.1124/jpet.103.058602.PMID14600248.S2CID22492018.
- ^Agar M, Clark K (10 February 2015)."Palliative Medicine".In Talley NJ, Frankum B, Currow D (eds.).Essentials of Internal Medicine(3rd ed.). Elsevier Health Sciences. pp. 491–.ISBN978-0-7295-8081-6.
- ^"Instructions for Mean Equivalent Daily Dose (MEDD)"(PDF).Archived fromthe original(PDF)on 27 July 2011.Retrieved22 August2010.
- ^Hydrocodone Bitartrate and Acetaminophen Tablets, USP 5 mg/325 mg CIIArchived22 February 2024 at theWayback Machinefda.gov
- ^Raffa RB, Colucci R, Pergolizzi JV (September 2017). "The effects of food on opioid-induced nausea and vomiting and pharmacological parameters: a systematic review".Postgraduate Medicine.129(7): 698–708.doi:10.1080/00325481.2017.1345282.PMID28635354.S2CID46184629.
- ^Bond M, Rabinovich-Guilatt L, Selim S, Darwish M, Tracewell W, Robertson P, et al. (December 2017). "Effect of Food on the Pharmacokinetics of Single- and Multiple-Dose Hydrocodone Extended Release in Healthy Subjects".Clinical Drug Investigation.37(12): 1153–1163.doi:10.1007/s40261-017-0575-3.PMID28948482.S2CID32440860.
{{cite journal}}
:CS1 maint: overridden setting (link) - ^Farr SJ, Robinson CY, Rubino CM (2015)."Effects of food and alcohol on the pharmacokinetics of an oral, extended-release formulation of hydrocodone in healthy volunteers".Clinical Pharmacology.7:1–9.doi:10.2147/CPAA.S70831.PMC4307648.PMID25653563.
- ^Devarakonda K, Kostenbader K, Giuliani MJ, Young JL (November 2015)."Single-dose pharmacokinetics of 2 or 3 tablets of biphasic immediate-release/extended-release hydrocodone bitartrate/acetaminophen (MNK-155) under fed and fasted conditions: two randomized open-label trials".BMC Pharmacology & Toxicology.16:31.doi:10.1186/s40360-015-0032-y.PMC4662814.PMID26614499.
- ^Jenkins AJ (9 October 2007)."Pharmacokinetics of Specific Drugs".In Karch SB (ed.).Pharmacokinetics and Pharmacodynamics of Abused Drugs.CRC Press. pp. 56–.ISBN978-1-4200-5460-6.Archivedfrom the original on 12 January 2023.Retrieved23 September2016.
- ^Broussard LA (22 January 2013)."Challenges in Confirmation Testing for Drugs of Abuse".In Dasgupta A, Sepulveda JL (eds.).Accurate Results in the Clinical Laboratory: A Guide to Error Detection and Correction.Newnes. pp. 239–.ISBN978-0-12-415858-0.
- ^abSepulveda JL (23 April 2012)."Genetic Aspect of Opiate Metabolism and Addiction".In Dasgupta A, Langman LJ (eds.).Pharmacogenomics of Alcohol and Drugs of Abuse.CRC Press. pp. 175–.ISBN978-1-4398-5611-6.Archivedfrom the original on 12 January 2023.Retrieved23 September2016.
- ^Kaplan HL, Busto UE, Baylon GJ, Cheung SW, Otton SV, Somer G, et al. (April 1997). "Inhibition of cytochrome P450 2D6 metabolism of hydrocodone to hydromorphone does not importantly affect abuse liability".The Journal of Pharmacology and Experimental Therapeutics.281(1): 103–108.PMID9103485.
- ^Gardiner SJ, Begg EJ (September 2006). "Pharmacogenetics, drug-metabolizing enzymes, and clinical practice".Pharmacological Reviews.58(3): 521–590.doi:10.1124/pr.58.3.6.PMID16968950.S2CID25747320.
- ^Crews KR, Gaedigk A, Dunnenberger HM, Klein TE, Shen DD, Callaghan JT, et al. (February 2012)."Clinical Pharmacogenetics Implementation Consortium (CPIC) guidelines for codeine therapy in the context of cytochrome P450 2D6 (CYP2D6) genotype".Clinical Pharmacology and Therapeutics.91(2): 321–326.doi:10.1038/clpt.2011.287.PMC3289963.PMID22205192.
{{cite journal}}
:CS1 maint: overridden setting (link) - ^Madadi P, Hildebrandt D, Gong IY, Schwarz UI, Ciszkowski C, Ross CJ, et al. (October 2010). "Fatal hydrocodone overdose in a child: pharmacogenetics and drug interactions".Pediatrics.126(4): e986–e989.doi:10.1542/peds.2009-1907.PMID20837591.S2CID42365304.
{{cite journal}}
:CS1 maint: overridden setting (link) - ^Vuilleumier PH, Stamer UM, Landau R (2012)."Pharmacogenomic considerations in opioid analgesia".Pharmacogenomics and Personalized Medicine.5:73–87.doi:10.2147/PGPM.S23422.PMC3513230.PMID23226064.
- ^Spiller HA (March 2003). "Postmortem oxycodone and hydrocodone blood concentrations".Journal of Forensic Sciences.48(2): 429–431.doi:10.1520/JFS2002309.PMID12665006.
- ^Baselt RC (2017).Disposition of Toxic Drugs and Chemicals in Man.Biomedical Publications. pp. 1050–1052.ISBN978-0-692-77499-1.
- ^Carroll RJ, Leisch H, Rochon L, Hudlicky T, Cox DP (January 2009). "One-pot conversion of thebaine to hydrocodone and synthesis of neopinone ketal".The Journal of Organic Chemistry.74(2): 747–752.doi:10.1021/jo802454v.PMID19072148.
- ^Sinatra RS (6 December 2010).The Essence of Analgesia and Analgesics.Cambridge: Cambridge University Press. pp. 73, 81.ISBN9780511841378.
- ^Cruz SL (27 October 2016).Neuroscience in the 21st Century.New York, NY: Springer. pp. 3626, 3657.ISBN978-1-4939-3474-4.
- ^Mannich C, Löwenheim H (1920)."Ueber zwei neue Reduktionsprodukte des Kodeins".Archiv der Pharmazie.258(2–4): 295–316.doi:10.1002/ardp.19202580218.ISSN0365-6233.S2CID97513395.Archivedfrom the original on 1 August 2020.Retrieved12 September2019.
- ^"Drugs@FDA—Approval History: Hycodan".FDA.Archivedfrom the original on 28 August 2021.Retrieved7 January2006.
- ^"FDA Docket No. 2007N-0353, Drug Products Containing Hydrocodone; Enforcement Action Dates".FDA.Archivedfrom the original on 12 January 2008.Retrieved7 January2006.See section I. B.,DESI Review of Hydrocodone Products
- ^"Dihydromorphine".PubChem.U.S. National Library of Medicine.Archivedfrom the original on 14 July 2014.Retrieved21 May2021.
- ^"Dihydrocodeine".PubChem.U.S. National Library of Medicine.Archivedfrom the original on 21 May 2021.Retrieved21 May2021.
- ^International Narcotics Control Board Report 2008.United Nations Pubns. 2009. p. 20.ISBN978-9211482324.[permanent dead link]
- ^"Hydrocodone Combination Products".MedlinePlus.The American Society of Health-System Pharmacists, Inc.Archivedfrom the original on 5 July 2016.Retrieved14 July2018.
- ^McCarthy M (January 2016). "Prescriptions for hydrocodone plummet after US tightens prescribing rules".BMJ.352:i549.doi:10.1136/bmj.i549.PMID26819247.S2CID45954090.
- ^Jones CM, Lurie PG, Throckmorton DC (March 2016)."Effect of US Drug Enforcement Administration's Rescheduling of Hydrocodone Combination Analgesic Products on Opioid Analgesic Prescribing".JAMA Internal Medicine.176(3): 399–402.doi:10.1001/jamainternmed.2015.7799.PMID26809459.
- ^Chambers J, Gleason RM, Kirsh KL, Twillman R, Webster L, Berner J, et al. (September 2016)."An Online Survey of Patients' Experiences Since the Rescheduling of Hydrocodone: The First 100 Days".Pain Medicine.17(9): 1686–1693.doi:10.1093/pm/pnv064.PMID26814291.
{{cite journal}}
:CS1 maint: overridden setting (link) - ^"Schedules of Controlled Substances: Rescheduling of Hydrocodone Combination Products From Schedule III to Schedule II".Federal Register.22 August 2014.Archivedfrom the original on 11 August 2017.Retrieved11 August2017.
- ^"Drug-Related Hospital Emergency Room Visits".National Institute on Drug Abuse.Archivedfrom the original on 11 August 2017.Retrieved11 August2017.
External links
[edit]- "DEA Schedules of Controlled Substances: Rescheduling of Hydrocodone Combination Products From Schedule III to Schedule II".Federal Register.6 October 2014.Archivedfrom the original on 10 August 2016.Retrieved6 October2014.