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Hydromorphone

"Dihydromorphinone" redirects here. Not to be confused with dihydromorphine (Paramorfan, etc.), a different opioid.

Hydromorphone
Structural formula of hydromorphone
Space-filling model of hydromorphone
Clinical data
Trade namesDilaudid, others
Other namesDihydromorphinone
AHFS/Drugs.comMonograph
MedlinePlusa682013
License data
Pregnancy
category
Dependence
liability		High[2]
Addiction
liability		High[3]
Routes of
administration		By mouth, intramuscular, intravenous, subcutaneous
Drug classOpioid
ATC code
Legal status
Legal status
Pharmacokinetic data
BioavailabilityBy mouth: 25–50%,[5] Intranasal: 52–58%,[6] IV/IM: 100%
Protein binding20%
MetabolismLiver
Onset of action15–30 min[7]
Elimination half-life2–3 hours[8]
Duration of action4–5 hours[7]
ExcretionKidney
Identifiers
  • 4,5-α-Epoxy-3-hydroxy-17-methyl morphinan-6-one
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.006.713 Edit this at Wikidata
Chemical and physical data
FormulaC17H19NO3
Molar mass285.343 g·mol−1
3D model (JSmol)
Solubility in waterHCl salt: 333
  • O=C4[C@@H]5Oc1c2c(ccc1O)C[C@H]3N(CC[C@]25[C@H]3CC4)C
  • InChI=1S/C17H19NO3/c1-18-7-6-17-10-3-5-13(20)16(17)21-15-12(19)4-2-9(14(15)17)8-11(10)18/h2,4,10-11,16,19H,3,5-8H2,1H3/t10-,11+,16-,17-/m0/s1 checkY
  • Key:WVLOADHCBXTIJK-YNHQPCIGSA-N checkY
  (verify)

Hydromorphone, also known as dihydromorphinone, and sold under the brand name Dilaudid among others, is a morphinan opioid used to treat moderate to severe pain.[7] Typically, long-term use is only recommended for pain due to cancer.[9] It may be used by mouth or by injection into a vein, muscle, or under the skin.[7] Effects generally begin within half an hour and last for up to five hours.[7] A 2016 Cochrane review (updated in 2021) found little difference in benefit between hydromorphone and other opioids for cancer pain.[10]

Common side effects include dizziness, sleepiness, nausea, itchiness, and constipation.[7] Serious side effects may include abuse, low blood pressure, seizures, respiratory depression, and serotonin syndrome.[7] Rapidly decreasing the dose may result in opioid withdrawal.[7] Generally, use during pregnancy or breastfeeding is not recommended.[11] Hydromorphone is believed to work by activating opioid receptors, mainly in the brain and spinal cord.[7] Hydromorphone 2 mg IV is equivalent to approximately 10 mg morphine IV.[9]

Hydromorphone was patented in 1923.[12] Hydromorphone is made from morphine.[13] It is on the World Health Organization's List of Essential Medicines.[14] It is available as a generic medication.[7] In 2021, it was the 261st most commonly prescribed medication in the United States, with more than 1 million prescriptions.[15][16]

  1. ^ "Hydromorphone Use During Pregnancy". Drugs.com. 19 November 2019. Retrieved 16 May 2020.
  2. ^ Bonewit-West K, Hunt SA, Applegate E (2012). Today's Medical Assistant: Clinical and Administrative Procedures. Elsevier Health Sciences. p. 571. ISBN 9781455701506.
  3. ^ 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.
  4. ^ 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.
  5. ^ 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.
  6. ^ Coda BA, Rudy AC, Archer SM, Wermeling DP (July 2003). "Pharmacokinetics and bioavailability of single-dose intranasal hydromorphone hydrochloride in healthy volunteers". Anesthesia and Analgesia. 97 (1): 117–23, table of contents. CiteSeerX 10.1.1.551.6509. doi:10.1213/01.ANE.0000066311.40978.4F. PMID 12818953. S2CID 22694749.
  7. ^ a b c d e f g h i j "Hydromorphone Hydrochloride Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Retrieved 15 April 2019.
  8. ^ Vallner JJ, Stewart JT, Kotzan JA, Kirsten EB, Honigberg IL (April 1981). "Pharmacokinetics and bioavailability of hydromorphone following intravenous and oral administration to human subjects". Journal of Clinical Pharmacology. 21 (4): 152–156. doi:10.1002/j.1552-4604.1981.tb05693.x. PMID 6165742. S2CID 29864565.
  9. ^ a b British national formulary: BNF 76 (76 ed.). Pharmaceutical Press. 2018. pp. 24, 456. ISBN 9780857113382.
  10. ^ Li Y, Ma J, Lu G, Dou Z, Knaggs R, Xia J, et al. (August 2021). "Hydromorphone for cancer pain". The Cochrane Database of Systematic Reviews. 2021 (8): CD011108. doi:10.1002/14651858.CD011108.pub3. PMC 8406835. PMID 34350974.
  11. ^ "Hydromorphone Use During Pregnancy". Drugs.com. Retrieved 15 April 2019.
  12. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 526. ISBN 9783527607495.
  13. ^ Vardanyan R, Hruby V (2006). Synthesis of Essential Drugs. Elsevier. p. 25. ISBN 9780080462127.
  14. ^ World Health Organization (2023). The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023). Geneva: World Health Organization. hdl:10665/371090. WHO/MHP/HPS/EML/2023.02.
  15. ^ "The Top 300 of 2021". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.
  16. ^ "Hydromorphone - Drug Usage Statistics". ClinCalc. Retrieved 14 January 2024.
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