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Hydrocodone

Not to be confused with Dihydrocodeine.

Hydrocodone
Clinical data
Trade namesHysingla ER, Zohydro ER
Other namesDihydrocodeinone, hydrocodone bitartrate
AHFS/Drugs.comMonograph
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
Pharmacokinetic data
BioavailabilityOral: 70%[4]
Protein bindingLow[4][5]
MetabolismLiver: CYP3A4 (major), CYP2D6 (minor)[6]
MetabolitesNorhydrocodone[6]
Hydromorphone[6]
Others[6]
Onset of action10–20 minutes[2]
Elimination half-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
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.004.304 Edit this at Wikidata
Chemical and physical data
FormulaC18H21NO3
Molar mass299.370 g·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/s1 checkY
  • Key:LLPOLZWFYMWNKH-CMKMFDCUSA-N checkY
  (verify)

Hydrocodone, also known as dihydrocodeinone, is a semi-synthetic opioid used to treat pain and as a cough suppressant.[10] It is taken by mouth.[10] Typically, it is dispensed as the combination acetaminophen/hydrocodone or ibuprofen/hydrocodone for pain severe enough to require an opioid[11][12][13] and in combination with homatropine methylbromide to relieve cough.[10] It is also available by itself in a long-acting form sold 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, it is classified as a Schedule II Controlled Substance.

Common side effects include dizziness, sleepiness, nausea, and constipation.[10] Serious side effects may include low blood pressure, seizures, QT prolongation, respiratory depression, and serotonin syndrome.[10] Rapidly decreasing the dose may result in opioid withdrawal.[10] Use during pregnancy or breastfeeding is generally not recommended.[15] Hydrocodone is believed to work by activating opioid receptors, mainly in the brain and spinal cord.[10] Hydrocodone 10 mg is equivalent to about 10 mg of morphine by mouth.[16]

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 from codeine[20][21] or less often from thebaine.[22] Production using genetically engineered yeasts has been developed but is not used commercially.[23][24][25]

  1. ^ Bonewit-West K, Hunt SA, Applegate E (2012). Today's Medical Assistant: Clinical and Administrative Procedures. Elsevier Health Sciences. p. 571. ISBN 9781455701506. Archived from the original on 10 January 2023. Retrieved 20 August 2019.
  2. ^ a b c d Cite error: The named reference ElliottSmith2016 was invoked but never defined (see the help page).
  3. ^ 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). Archived from the original on 3 August 2023. Retrieved 16 August 2023.
  4. ^ a b Polsten 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–. ISBN 978-0-323-41494-4. Archived from the original on 12 January 2023. Retrieved 23 September 2016.
  5. ^ Chabner 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–. ISBN 978-1-60547-431-1. Archived from the original on 12 January 2023. Retrieved 23 September 2016.
  6. ^ a b c d Cite error: The named reference Zhou2016 was invoked but never defined (see the help page).
  7. ^ Cite error: The named reference DavisGlare2005 was invoked but never defined (see the help page).
  8. ^ Bluth MH (16 November 2016). Toxicology and Drug Testing, An Issue of Clinics in Laboratory Medicine, E-Book. Elsevier Health Sciences. pp. 85–. ISBN 978-0-323-47795-6. Archived from the original on 12 January 2023. Retrieved 22 June 2018.
  9. ^ Smith HS (21 February 2013). Opioid Therapy in the 21st Century. OUP USA. pp. 68–. ISBN 978-0-19-984497-5. Archived from the original on 12 January 2023. Retrieved 22 June 2018.
  10. ^ a b c d e f g h i "Hydrocodone Bitartrate Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Archived from the original on 14 November 2010. Retrieved 15 April 2019.
  11. ^ Mallinckrodt (10 March 2021). "HYDROCODONE BITARTRATE AND ACETAMINOPHEN tablet (label)". National Institutes of Health DailyMed. Archived from the original on 6 November 2021. Retrieved 6 November 2021.
  12. ^ 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. ISBN 9781608317080.
  13. ^ "Hydrocodone Combination Products: MedlinePlus Drug Information". medlineplus.gov. Archived from the original on 5 July 2016. Retrieved 4 November 2023.
  14. ^ "Hydrocodone: MedlinePlus Drug Information". medlineplus.gov. Archived from the original on 15 April 2019. Retrieved 15 April 2019.
  15. ^ "Hydrocodone Use During Pregnancy". Drugs.com. Archived from the original on 28 January 2014. Retrieved 15 April 2019.
  16. ^ "Opioid Dose Calculator". Agency Medical Directors' Group. Archived from the original on 10 February 2016. Retrieved 15 April 2019.
  17. ^ Cite error: The named reference Fis2006 was invoked but never defined (see the help page).
  18. ^ "Making Some Painkillers Harder to Get". The New York Times. 21 February 2013. Archived from the original on 3 January 2022. Retrieved 15 April 2019.
  19. ^ "Hydrocodone - Drug Usage Statistics". ClinCalc. Archived from the original on 13 November 2022. Retrieved 7 October 2022.
  20. ^ Stoker HS (2012). General, Organic, and Biological Chemistry. Cengage Learning. p. 567. ISBN 9781133711285.
  21. ^ Vardanyan R, Hruby V (10 March 2006). Synthesis of Essential Drugs. Elsevier. ISBN 978-0-08-046212-7.
  22. ^ Narcotic Drugs 2020, Estimated World Requirements for 2021, Statistics for 2019 (PDF). International Narcotics Control Board. 2020. p. 37. ISBN 978-92-1-148355-0. Archived (PDF) from the original on 3 November 2021. Retrieved 12 December 2021. 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...
  23. ^ 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. PMC 4924617. PMID 26272907.
  24. ^ 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. PMC 4167936. PMID 25151135.
  25. ^ 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. PMC 4748248. PMID 26847395.{{cite journal}}: CS1 maint: overridden setting (link)

Hydrocodone

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