Hydromorphone

Hydromorphone, also known as

Hydromorphone
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] Clinical data
Hydromorphone is believed to work by activating Trade names Dilaudid, others
opioid receptors, mainly in the brain and spinal Other names Dihydromorphinone
cord.[7] Hydromorphone 2 mg IV is equivalent to
AHFS/Drugs.com Monograph (https://www.drug
approximately 10 mg morphine IV.[9]
s.com/monograph/hydromorp
Hydromorphone was patented in 1923.[12] hone-hydrochloride.html)
Hydromorphone is made from morphine.[13] It is on MedlinePlus a682013 (https://medlineplus.
the World Health Organization's List of Essential gov/druginfo/meds/a682013.h
Medicines.[14] It is available as a generic tml)
medication.[7] In 2022, it was the 233rd most License data US DailyMed: Hydromorphone
commonly prescribed medication in the United (https://dailymed.nlm.nih.gov/
States, with more than 1 million prescriptions.[15][16] dailymed/search.cfm?labeltyp
e=all&query=Hydromorphon
e)
Side effects Pregnancy AU: C
[1]
category
Adverse effects of hydromorphone are similar to Dependence High[2]
those of other potent opioid analgesics such as liability
morphine and heroin. The major hazards of Addiction High[3]
hydromorphone include dose-related respiratory liability
depression, urinary retention, bronchospasm, and Routes of By mouth, intramuscular,
administration intravenous, subcutaneous
sometimes, circulatory depression.[17] More common
side effects include lightheadedness, dizziness, Drug class Opioid
sedation, itching, constipation, nausea, vomiting, ATC code N02AA03 (WHO (https://www.
headache, perspiration, and hallucinations.[17] These whocc.no/atc_ddd_index/?co
symptoms are common in ambulatory patients and in de=N02AA03))
those not experiencing severe pain.
Legal status
Simultaneous use of hydromorphone with other Legal status AU: S8 (Controlled drug)
opioids, muscle relaxants, tranquilizers, sedatives, BR: Class A1 (Narcotic
and general anesthetics may cause a significant drugs)[4]
increase in respiratory depression, progressing to
CA: Schedule I
coma or death. Taking benzodiazepines (e.g.,
DE: Anlage III (Special
diazepam) in conjunction with hydromorphone may
increase side effects such as dizziness and difficulty prescription form required)
concentrating.[18] If simultaneous use of these drugs NZ: Class B

is required, dose adjustment may be made.[19] UK: Class A Controlled Drug:

Schedule II
A particular problem that may occur with
US: Schedule II
hydromorphone is accidental administration in place
of morphine due to a mix-up between the similar UN: Narcotic Schedule I

names, either at the time the prescription is written or SE: Förteckning II

when the drug is dispensed. This has led to several Pharmacokinetic data
deaths and calls for hydromorphone to be distributed Bioavailability By mouth: 25–50%,[5]
in distinctly different packaging from morphine to
Intranasal: 52–58%,[6] IV/IM:
avoid confusion.[20][21]
100%

Massive overdoses are rarely observed in opioid- Protein binding 20%

tolerant individuals, but when they occur, they may Metabolism Liver
lead to circulatory system collapse. Symptoms of Onset of action 15–30 min[7]
overdose include respiratory depression, drowsiness Elimination 2–3 hours[8]
leading to coma and sometimes to death, drooping of half-life
skeletal muscles, low heart rate, and decreasing Duration of 4–5 hours[7]
blood pressure. At the hospital, individuals with action
hydromorphone overdose are provided supportive Excretion Kidney
care, such as assisted ventilation to provide oxygen Identifiers
and gut decontamination using activated charcoal IUPAC name
through a nasogastric tube. Opioid antagonists, such
4,5-α-Epoxy-3-hydroxy-17-methyl morphinan-6-on
as naloxone, also may be administered concurrently
e
with oxygen supplementation. Naloxone works by
CAS Number 466-99-9 (https://commonche
reversing the effects of hydromorphone, and only is
administered in the presence of significant mistry.cas.org/detail?cas_rn=
respiratory depression and circulatory depression.[19] 466-99-9)
PubChem CID 5284570 (https://pubchem.nc
Sugar cravings associated with hydromorphone use bi.nlm.nih.gov/compound/528
are the result of a glucose crash after transient 4570)
hyperglycemia following injection, or a less
IUPHAR/BPS 7082 (https://www.guidetopha
rmacology.org/GRAC/Ligand
profound lowering of blood sugar over a period of DisplayForward?ligandId=708
hours, in common with morphine, heroin, codeine, 2)
and other opioids. DrugBank DB00327 (https://www.drugba
nk.ca/drugs/DB00327)
Hormone imbalance ChemSpider 4447624 (https://www.chems
As with other opioids, hydromorphone (particularly pider.com/Chemical-Structur
during heavy chronic use) often causes temporary e.4447624.html)
hypogonadism or hormone imbalance.[22] UNII Q812464R06 (https://precisio
n.fda.gov/uniisearch/srs/unii/
Q812464R06)
Neurotoxicity
KEGG D08047 (https://www.kegg.jp/
In the setting of prolonged use, high dosage, and/or
entry/D08047)
kidney dysfunction, hydromorphone has been
associated with neuroexcitatory symptoms such as ChEBI CHEBI:5790 (https://www.ebi.
tremor, myoclonus, agitation, and cognitive ac.uk/chebi/searchId.do?cheb
dysfunction.[23][24][25] This toxicity is less than that iId=CHEBI:5790)
associated with other classes of opioids such as the ChEMBL ChEMBL398707 (https://www.
pethidine class of synthetics in particular. ebi.ac.uk/chembl/explore/com
pound/ChEMBL398707)
Withdrawal CompTox DTXSID8023133 (https://com
Dashboard (EPA)
Users of hydromorphone may experience painful ptox.epa.gov/dashboard/che
mical/details/DTXSID802313
symptoms if the drug is suspended.[26] Some people
3)
cannot tolerate the symptoms, which results in
continuous drug use.[26] Symptoms of opioid ECHA InfoCard 100.006.713 (https://echa.eur
withdrawal are not easy to decipher, as there are opa.eu/substance-informatio
differences between drug-seeking behaviors and true n/-/substanceinfo/100.006.71
withdrawal effects.[27] Symptoms associated with 3)
hydromorphone withdrawal include:[26][27][28] Chemical and physical data
Formula C17H19NO3
Abdominal pain
Molar mass 285.343 g·mol−1
Anxiety
3D model Interactive image (https://che
Panic attacks
(JSmol)
Depression mapps.stolaf.edu/jmol/jmol.ph
Piloerection (goose bumps) p?model=O%3DC4%5BC%4
Inability to enjoy daily activities 0%40H%5D5Oc1c2c%28ccc
Muscle and joint pain 1O%29C%5BC%40H%5D3
N%28CC%5BC%40%5D25%
Nausea
5BC%40H%5D3CC4%29C)
Vomiting
Runny nose and excessive secretion of Solubility in HCl salt: 333
tears water

Sweating SMILES
O=C4[C@@H]5Oc1c2c(ccc1O)C[C@H]3N(CC[C
In the clinical setting, excessive secretion of tears, @]25[C@H]3CC4)C
yawning, and dilation of pupils are helpful
InChI
presentations in diagnosing opioid withdrawal.[29]
Hydromorphone is a rapid-acting painkiller;
however, some formulations may last up to several InChI=1S/C17H19NO3/c1-18-7-6-17-10-3-5-13(2
0)16(17)21-15-12(19)4-2-9(14(15)17)8-11(10)1
hours. Patients who stop taking this drug abruptly
8/h2,4,10-11,16,19H,3,5-8H2,1H3/t10-,11+,16-,
may experience withdrawal symptoms,[28][30] which 17-/m0/s1
may start within hours of taking the last dose of
Key:WVLOADHCBXTIJK-YNHQPCIGSA-N
hydromorphone, and last up to several weeks.[26]
(verify)
Withdrawal symptoms in people who stopped taking
the opioid may be managed by using opioids or non-
opioid adjuncts.[31] Methadone is an opioid commonly used for this kind of therapy. However, the
selection of therapy should be tailored to each specific person.[32] Methadone also is used for
detoxification in people who have opiate addiction, such as heroin or drugs similar to morphine.[32] It
may be given orally or intramuscularly. There is controversy regarding whether any opioid (such as
methadone) should be included in the treatment of opioid withdrawal symptoms, since these agents also
may cause relapse when therapy is suspended.[26] Clonidine is a non-opioid adjunct which may be used
in situations where opioid use is not desired, such as in patients with high blood pressure.[33]

Interactions
CNS depressants may enhance the depressant effects of hydromorphone, such as other opioids,
anesthetics, sedatives, hypnotics, barbiturates, benzodiazepines, phenothiazines, chloral hydrate,
dimenhydrinate, and glutethimide. The depressant effect of hydromorphone also may be enhanced by
monoamine oxidase inhibitors (MAO inhibitors), first-generation antihistamines (e.g., brompheniramine,
promethazine, diphenhydramine, chlorphenamine), beta blockers, and alcohol. When combined therapy is
contemplated, the dose of one or both agents should be reduced.[23]

Pharmacology
Hydromorphone is a semi-synthetic μ-opioid agonist. Hydromorphone at opioid receptors[34]
As a hydrogenated ketone of morphine, it shares the
Affinities (Ki) Ratio
pharmacologic properties typical of opioid analgesics.
Hydromorphone and related opioids produce their MOR DOR KOR MOR:DOR:KOR
major effects on the central nervous system and 0.47 nM 18.5 nM 24.9 nM 1:39:53
gastrointestinal tract. These include analgesia,
drowsiness, mental clouding, changes in mood, euphoria or dysphoria, respiratory depression, cough
suppression, decreased gastrointestinal motility, nausea, vomiting, increased cerebrospinal fluid pressure,
increased biliary pressure, and increased pinpoint constriction of the pupils.[30]

Formulations
Hydromorphone is available in parenteral, rectal, subcutaneous, and oral formulations, and also can be
administered via epidural or intrathecal injection.[38] Hydromorphone also has been administered via
nebulization to treat shortness of breath, but it is not used as a route for pain control due to low
bioavailability.[39] Transdermal delivery systems are also under consideration to induce local skin
analgesia.[40]
Concentrated aqueous solutions of hydromorphone hydrochloride
have a visibly different refractive index from pure water, isotonic Equianalgesic doses[35][36][37]
9 ‰ (0·9 per cent) saline and the like, especially when stored in Compound Route Dose
clear ampoules and phials may acquire a slight clear amber Codeine PO 200 mg
discolouration upon exposure to light; this reportedly has no effect
Hydrocodone PO 20–30 mg
on the potency of the solution, but 14-dihydromorphinones such
as hydromorphone, oxymorphone, and relatives come with Hydromorphone PO 7.5 mg
instructions to protect from light.[41] Ampoules of solution which Hydromorphone IV 1.5 mg
have developed a precipitate should be discarded.[41] Morphine PO 30 mg

Battery-powered intrathecal drug delivery systems are implanted Morphine IV 10 mg

for chronic pain when other options are ruled out, such as surgery Oxycodone PO 20 mg
and traditional pharmacotherapy, provided that the patient is Oxycodone IV 10 mg
considered a suitable fit in terms of any contraindications, both
Oxymorphone PO 10 mg
physiological and psychological.[42]
Oxymorphone IV 1 mg
An extended-release (once-daily) version of hydromorphone is
available in the United States.[43] Previously, an extended-release
version of hydromorphone, Palladone, was available before being
voluntarily withdrawn from the market after a July 2005 FDA
advisory warned of a high overdose potential when taken with
alcohol. As of March 2010, it is still available in the United
Kingdom under the brand name Palladone SR, Nepal under the
brand name Opidol, and in most other European countries,[44] In
Canada, pre­scrip­tion continuous release hydro­morphone is
available as both brand name (Hydro­morph Contin) and generic
formu­lations (Apo-Hydro­morphone CR).[45]

Pharmacokinetics
The chemical modification of the morphine molecule to hydromorphone results in higher lipid solubility
and greater ability to cross the blood–brain barrier to produce more rapid and complete central nervous
system penetration. On a per milligram basis, hydromorphone is considered to be five times as potent as
morphine; although the conversion ratio may vary from 4–8 times, five times is in typical clinical
usage.[46][47]

Patients with renal abnormalities must exercise caution when dosing hydromorphone. In those with renal
impairment, the half-life of hydromorphone may increase to as much as 40 hours. The typical half-life of
intravenous hydromorphone is 2.3 hours.[48] Peak plasma levels usually occur between 30 and 60 minutes
after oral dosing.[49]

The onset of action for hydromorphone administered intravenously is less than 5 minutes and within 30
minutes of oral administration (immediate release).[39]

Metabolism
While other opioids in its class, such as codeine or oxycodone, are metabolized via CYP450 enzymes,
hydromorphone is not.[50] Hydromorphone is extensively metabolized in the liver to hydromorphone-3-
glucuronide, which has no analgesic effects. As similarly seen with the morphine metabolite, morphine-3-
glucuronide, a build-up in levels of hydromorphone-3-glucuronide may produce excitatory neurotoxic
effects such as restlessness, myoclonus and hyperalgesia. Patients with compromised kidney function and
older patients are at higher risk for metabolite accumulation.[51]

Chemistry
With a formula of C17H19NO3 and a molecular weight of 285.343, both identical to morphine,
hydromorphone can be considered a structural isomer of morphine and is a hydrogenated ketone
thereof.[52]

Hydromorphone is made from morphine either by direct re-arrangement (made by reflux heating of
alcoholic or acidic aqueous solution of morphine in the presence of platinum or palladium catalyst) or
reduction to dihydromorphine (usually via catalytic hydrogenation), followed by oxidation with
benzophenone in presence of potassium tert butoxide or aluminium tert butoxide (Oppenauer oxidation).
The 6 ketone group may be replaced with a methylene group via the Wittig reaction to produce 6-
Methylenedihydrodesoxymorphine, which is 80× stronger than morphine.[53]

Hydromorphone is more soluble in water than morphine; therefore, hydromorphone solutions may be
produced to deliver the drug in a smaller volume of water. The hydrochloride salt is soluble in three parts
of water, whereas a gram of morphine hydrochloride dissolves in 16 ml of water; for all common
purposes, the pure powder for hospital use can be used to produce solutions of virtually arbitrary
concentration. When the powder appeared on the street, this very small volume of powder needed for a
dose means that overdoses are likely for those who mistake it for heroin or other powdered narcotics,
especially those that have been diluted prior to consumption.[54]

Bacteria
Some bacteria have been shown to be able to turn morphine into closely related drugs, including
hydromorphone and dihydromorphine among others. The bacterium Pseudomonas putida serotype M10
produces a naturally-occurring NADH-dependent morphinone reductase that can work on unsaturated 7,8
bonds, with result that, when these bacteria are living in an aqueous solution containing morphine,
significant amounts of hydromorphone form, as it is an intermediary metabolite in this process; the same
goes for codeine being turned into hydrocodone.[55]

History
Hydromorphone was patented in 1923.[12] It was introduced to the mass market in 1926 under the brand
name Dilaudid,[56] indicating its derivation and degree of similarity to morphine (by way of laudanum).

Society and culture

Names
Hydromorphone is known in various countries around the world by the brand names Hydal, Dimorphone,
Exalgo, Sophidone LP, Dilaudid, Hydrostat, Hydromorfan, Hydromorphan, Hymorphan, Laudicon,
Opidol, Palladone, Hydromorph Contin, and others. An extended-release version of hydromorphone,
called Palladone, was available for a short time in the United States before being voluntarily withdrawn
from the market after a July 2005 FDA advisory warned of a high overdose potential when taken with
alcohol.[57] As of March 2010, it is still available in Nepal under the brand name Opidol, in the United
Kingdom under the brand name Palladone SR, and in most other European countries.

There has also been a once-daily prolonged release version of hydromorphone available in Australia
under the brand name Jurnista as of May 2009.[58]

Legal status
In the United States, the main drug control agency, the Drug Enforcement Administration, reports an
increase in annual aggregate production quotas of hydromorphone from 766 kilograms (1,689 pounds) in
1998 to 3,300 kilograms (7,300 lb) in 2006, and an increase in prescriptions in this time of 289%, from
about 470,000 to 1,830,000. The 2013 production quota was 5,968 kilograms (13,157 lb).[59]

Like all opioids used for analgesia, hydromorphone is potentially habit-forming and is listed in Schedule
II of the United States Controlled Substances Act of 1970 as well as in similar levels under the drugs laws
of practically all other countries and it is listed in the Single Convention On Narcotic Drugs. The DEA
ACSCN for hydromorphone is 9150.

Hydromorphone is listed under the German Betäubungsmittelgesetz as a Betäubungsmittel in the most

restricted schedule for medicinal drugs; it is controlled similarly in Austria (Suchtgift) under the SMG
and the Swiss BetmG. The Misuse of Drugs Act 1971 (United Kingdom) and comparable French,
Canadian, Australian, Italian, Czech, Croatian, Slovenian, Swedish, Polish, Spanish, Greek, Russian, and
other laws similarly control it, as do regulations in virtually all other countries.

Use in executions
In 2009, Ohio approved the use of an intramuscular injection of 500 mg of hydromorphone and a
supratherapeutic dose of midazolam as a backup means of carrying out executions by lethal injection
when a suitable vein cannot be found for intravenous injection.[60]
Hydromorphone and midazolam was injected intravenously to execute double-murderer Joseph Wood in
Arizona on 24 July 2014. Wood was heavily sedated (surgical anesthesia) within four minutes from start,
but took almost two hours to transition to stage 4 (cessation of respiration) and death.[61]

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External links
Dihydromorphinones from morphine & analogues (http://www.erowid.org/archive/rhodium/ch
emistry/dihydromorphinones.html)
"When is a pain doctor a drug pusher?" (https://www.nytimes.com/2007/06/17/magazine/17
pain-t.html), The New York Times, 17 June 2007

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