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Hydrocodone

From Wikipedia, the free encyclopedia
Not to be confused withDihydrocodeine.

Hydrocodone
Clinical data
Trade namesHysingla ER, Zohydro ER
Other namesDihydrocodeinone, hydrocodone bitartrate
AHFS/DrugsMonograph
MedlinePlusa601006
License data
Dependence
liability		High[1]
Addiction
liability		High
Routes of
administration		Clinical:by mouth[2]
Others:intranasal,rectal
Drug classOpioid
ATC code
Legal status
Legal status
Pharmacokineticdata
BioavailabilityBy mouth: 70%[4]
Protein bindingLow[4][5]
MetabolismLiver:CYP3A4(major),CYP2D6(minor)[6]
Metabolites•Norhydrocodone[6]
•Hydromorphone[6]
• Others[6]
Onset of action10–20 minutes[2]
Eliminationhalf-lifeAverage: 3.8 hours[7]
Range: 3.3–4.4 hours[2]
Duration of action4–8 hours[2]
ExcretionUrine[8][9]
Identifiers
  • 4,5α-epoxy-3-methoxy-17-methylmorphinan-6-one
CAS Number
PubChemCID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.004.304Edit this at Wikidata
Chemical and physical data
FormulaC18H21NO3
Molar mass299.370g·mol−1
3D model (JSmol)
  • O=C4[C@@H]5Oc1c2c(ccc1OC)C[C@H]3N(CC[C@]25[C@H]3CC4)C
  • InChI=1S/C18H21NO3/c1-19-8-7-18-11-4-5-13(20)17(18)22-16-14(21-2)6-3-10(15(16)18)9-12(11)19/h3,6,11-12,17H,4-5,7-9H2,1-2H3/t11-,12+,17-,18-/m0/s1checkY
  • Key:LLPOLZWFYMWNKH-CMKMFDCUSA-NcheckY
(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]
See also:Hydrocodone/paracetamol,Hydrocodone/ibuprofen,andHydrocodone/aspirin

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]
Hydrocodone (and metabolite) at opioid receptors
Compound Affinities(KiTooltip Inhibitor constant) Ratio Ref
MORTooltip μ-Opioid receptor DORTooltip δ-Opioid receptor KORTooltip κ-Opioid receptor 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]

Equivalent analgesiadoses[51][52][53]
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]
Main articles:Hydrocodone/paracetamolandHydrocodone/ibuprofen
Hydrocodone and paracetamol (acetaminophen) 10-325 tablets (Mallinckrodt)

Most hydrocodone formulations include a second analgesic, such as paracetamol (acetaminophen) or ibuprofen. Examples of hydrocodone combinations include Norco, Vicodin, Vicoprofen and Riboxen.[82]

[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]

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