Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C17H19NO3.ClH |
Molecular Weight | 321.799 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.[H][C@@]12OC3=C4C(C[C@H]5N(C)CC[C@@]14[C@@]5([H])CCC2=O)=CC=C3O
InChI
InChIKey=XHILEZUETWRSHC-NRGUFEMZSA-N
InChI=1S/C17H19NO3.ClH/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;1H/t10-,11+,16-,17-;/m0./s1
Hydromorphone (also known as dihydromorphinone and the brand name Dilaudid among others) is a more potent opioid analgesic than morphine and is used for moderate to severe pain. It can be administered by injection, by infusion, by mouth, and rectally. Oral bioavailability is low. The kidney excretes hydromorphone and its metabolites. Some metabolites may have greater analgesic activity than hydromorphone itself but are unlikely to contribute to the pharmacological activity of hydromorphone. With the exception of pruritus, sedation and nausea and vomiting, which may occur less after hydromorphone than after morphine, the side-effects of these drugs are similar. Hydromorphone interacts predominantly with the opioid mu-receptors. These mu-binding sites are discretely distributed in the human brain, with high densities in the posterior amygdala, hypothalamus, thalamus, nucleus caudatus, putamen, and certain cortical areas. It also binds with kappa and delta receptors which are thought to mediate spinal analgesia, miosis and sedation.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL237 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16433932 |
279.0 nM [EC50] | ||
Target ID: CHEMBL236 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9301669 |
|||
Target ID: CHEMBL233 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18789923 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Palliative | DILAUDID-HP Approved UseDILAUDID INJECTION is indicated for the management of pain severe enough to require an opioid analgesic and for which alternate treatments are inadequate. DILAUDID-HP INJECTION is indicated for use in opioid-tolerant patients who require higher doses of opioids for the management of pain severe enough to require an opioid analgesic and for which alternate treatments are inadequate. Patients considered opioid tolerant are those who are taking for one week or longer,around-the-clock medicine consisting of at least 60 mg oral morphine per day, or at least 25 mcg transdermal fentanyl per hour, or at least 30 mg oral oxycodone per day, or at least 8 g oral hydromorphone per day, or at least 25 mg oral oxymorphone per day, or at least 60 mg oral hydrocodone per day, or an equianalgesic dose of another opioid for one week or longer. Patients must remain on around-the-clock opioids while administering DILAUDID-HP Launch Date4.42627195E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
5.5 ng/mL |
8 mg single, oral dose: 8 mg route of administration: Oral experiment type: SINGLE co-administered: |
HYDROMORPHONE HYDROCHLORIDE plasma | Homo sapiens population: HEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
23.7 ng × h/mL |
8 mg single, oral dose: 8 mg route of administration: Oral experiment type: SINGLE co-administered: |
HYDROMORPHONE HYDROCHLORIDE plasma | Homo sapiens population: HEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2.6 h |
8 mg single, oral dose: 8 mg route of administration: Oral experiment type: SINGLE co-administered: |
HYDROMORPHONE HYDROCHLORIDE plasma | Homo sapiens population: HEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
81% |
8 mg single, oral dose: 8 mg route of administration: Oral experiment type: SINGLE co-administered: |
HYDROMORPHONE HYDROCHLORIDE plasma | Homo sapiens population: HEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
540 mg single, intrathecal Overdose Dose: 540 mg Route: intrathecal Route: single Dose: 540 mg Sources: Page: p.274 |
unhealthy, 27 n = 1 Health Status: unhealthy Condition: Pain Age Group: 27 Sex: F Population Size: 1 Sources: Page: p.274 |
Disc. AE: Sleepiness, Nausea... AEs leading to discontinuation/dose reduction: Sleepiness Sources: Page: p.274Nausea |
2 mg 3 times / day multiple, intravenous Recommended Dose: 2 mg, 3 times / day Route: intravenous Route: multiple Dose: 2 mg, 3 times / day Sources: Page: p.378 |
unhealthy, 40 n = 1 Health Status: unhealthy Condition: Pain Age Group: 40 Sex: M Population Size: 1 Sources: Page: p.378 |
Disc. AE: Respiratory arrest... AEs leading to discontinuation/dose reduction: Respiratory arrest (grade 5) Sources: Page: p.378 |
4 mg 4 times / day multiple, oral (max) Recommended Dose: 4 mg, 4 times / day Route: oral Route: multiple Dose: 4 mg, 4 times / day Sources: Page: p.545 |
unhealthy, 67.7 n = 88 Health Status: unhealthy Condition: Pain Age Group: 67.7 Sex: M+F Population Size: 88 Sources: Page: p.545 |
Disc. AE: Somnolence, Aspiration pneumonia... AEs leading to discontinuation/dose reduction: Somnolence (serious, 1.14%) Sources: Page: p.545Aspiration pneumonia (grade 5, 1.14%) Toxic skin eruption (serious, 1.14%) Nausea and vomiting (serious, 1.14%) |
10 mg single, intravenous Overdose Dose: 10 mg Route: intravenous Route: single Dose: 10 mg Sources: Page: p.378 |
unhealthy n = 1 Health Status: unhealthy Condition: Pain Population Size: 1 Sources: Page: p.378 |
Disc. AE: Cardio-respiratory arrest... AEs leading to discontinuation/dose reduction: Cardio-respiratory arrest (grade 5) Sources: Page: p.378 |
2 mg 6 times / day multiple, subcutaneous|intramuscular Recommended Dose: 2 mg, 6 times / day Route: subcutaneous|intramuscular Route: multiple Dose: 2 mg, 6 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Pain Sources: Page: p.1 |
Disc. AE: Respiratory depression... AEs leading to discontinuation/dose reduction: Respiratory depression Sources: Page: p.1 |
4 mg 6 times / day multiple, oral Recommended Dose: 4 mg, 6 times / day Route: oral Route: multiple Dose: 4 mg, 6 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Pain Sources: Page: p.1 |
Disc. AE: Addiction, Abuse... AEs leading to discontinuation/dose reduction: Addiction Sources: Page: p.1Abuse Respiratory depression (grade 3-5) Withdrawal syndrome neonatal (grade 3-5) Coma (grade 5) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Nausea | Disc. AE | 540 mg single, intrathecal Overdose Dose: 540 mg Route: intrathecal Route: single Dose: 540 mg Sources: Page: p.274 |
unhealthy, 27 n = 1 Health Status: unhealthy Condition: Pain Age Group: 27 Sex: F Population Size: 1 Sources: Page: p.274 |
Sleepiness | Disc. AE | 540 mg single, intrathecal Overdose Dose: 540 mg Route: intrathecal Route: single Dose: 540 mg Sources: Page: p.274 |
unhealthy, 27 n = 1 Health Status: unhealthy Condition: Pain Age Group: 27 Sex: F Population Size: 1 Sources: Page: p.274 |
Respiratory arrest | grade 5 Disc. AE |
2 mg 3 times / day multiple, intravenous Recommended Dose: 2 mg, 3 times / day Route: intravenous Route: multiple Dose: 2 mg, 3 times / day Sources: Page: p.378 |
unhealthy, 40 n = 1 Health Status: unhealthy Condition: Pain Age Group: 40 Sex: M Population Size: 1 Sources: Page: p.378 |
Aspiration pneumonia | grade 5, 1.14% Disc. AE |
4 mg 4 times / day multiple, oral (max) Recommended Dose: 4 mg, 4 times / day Route: oral Route: multiple Dose: 4 mg, 4 times / day Sources: Page: p.545 |
unhealthy, 67.7 n = 88 Health Status: unhealthy Condition: Pain Age Group: 67.7 Sex: M+F Population Size: 88 Sources: Page: p.545 |
Nausea and vomiting | serious, 1.14% Disc. AE |
4 mg 4 times / day multiple, oral (max) Recommended Dose: 4 mg, 4 times / day Route: oral Route: multiple Dose: 4 mg, 4 times / day Sources: Page: p.545 |
unhealthy, 67.7 n = 88 Health Status: unhealthy Condition: Pain Age Group: 67.7 Sex: M+F Population Size: 88 Sources: Page: p.545 |
Somnolence | serious, 1.14% Disc. AE |
4 mg 4 times / day multiple, oral (max) Recommended Dose: 4 mg, 4 times / day Route: oral Route: multiple Dose: 4 mg, 4 times / day Sources: Page: p.545 |
unhealthy, 67.7 n = 88 Health Status: unhealthy Condition: Pain Age Group: 67.7 Sex: M+F Population Size: 88 Sources: Page: p.545 |
Toxic skin eruption | serious, 1.14% Disc. AE |
4 mg 4 times / day multiple, oral (max) Recommended Dose: 4 mg, 4 times / day Route: oral Route: multiple Dose: 4 mg, 4 times / day Sources: Page: p.545 |
unhealthy, 67.7 n = 88 Health Status: unhealthy Condition: Pain Age Group: 67.7 Sex: M+F Population Size: 88 Sources: Page: p.545 |
Cardio-respiratory arrest | grade 5 Disc. AE |
10 mg single, intravenous Overdose Dose: 10 mg Route: intravenous Route: single Dose: 10 mg Sources: Page: p.378 |
unhealthy n = 1 Health Status: unhealthy Condition: Pain Population Size: 1 Sources: Page: p.378 |
Respiratory depression | Disc. AE | 2 mg 6 times / day multiple, subcutaneous|intramuscular Recommended Dose: 2 mg, 6 times / day Route: subcutaneous|intramuscular Route: multiple Dose: 2 mg, 6 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Pain Sources: Page: p.1 |
Abuse | Disc. AE | 4 mg 6 times / day multiple, oral Recommended Dose: 4 mg, 6 times / day Route: oral Route: multiple Dose: 4 mg, 6 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Pain Sources: Page: p.1 |
Addiction | Disc. AE | 4 mg 6 times / day multiple, oral Recommended Dose: 4 mg, 6 times / day Route: oral Route: multiple Dose: 4 mg, 6 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Pain Sources: Page: p.1 |
Respiratory depression | grade 3-5 Disc. AE |
4 mg 6 times / day multiple, oral Recommended Dose: 4 mg, 6 times / day Route: oral Route: multiple Dose: 4 mg, 6 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Pain Sources: Page: p.1 |
Withdrawal syndrome neonatal | grade 3-5 Disc. AE |
4 mg 6 times / day multiple, oral Recommended Dose: 4 mg, 6 times / day Route: oral Route: multiple Dose: 4 mg, 6 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Pain Sources: Page: p.1 |
Coma | grade 5 Disc. AE |
4 mg 6 times / day multiple, oral Recommended Dose: 4 mg, 6 times / day Route: oral Route: multiple Dose: 4 mg, 6 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Pain Sources: Page: p.1 |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 6.0 |
weak [IC50 >50 uM] | |||
Page: 6.0 |
weak [IC50 >50 uM] | |||
Page: 6.0 |
weak [IC50 >50 uM] | |||
Page: 6.0 |
weak [IC50 >50 uM] | |||
Page: 6.0 |
weak [IC50 >50 uM] |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
yes | ||||
yes | ||||
yes | ||||
yes |
PubMed
Title | Date | PubMed |
---|---|---|
Opioid formulations: tailoring to the needs in chronic pain. | 2001 |
|
Pharmacokinetics of oral immediate-release hydromorphone (Dilaudid IR) in subjects with moderate hepatic impairment. | 2001 |
|
Pharmacokinetics of oral immediate-release hydromorphone (Dilaudid IR) in subjects with renal impairment. | 2001 |
|
Dose proportionality of the pharmacokinetics of oral immediate-release hydromorphone (Dilaudid IR). | 2001 |
|
Effects of hydromorphone or oxymorphone, with or without acepromazine, on preanesthetic sedation, physiologic values, and histamine release in dogs. | 2001 Apr 1 |
|
Pretreatment with hydromorphone, a mu-opioid agonist, does not alter the acute behavioral and physiological effects of ethanol in humans. | 2001 Jan |
|
Pharmacodynamics of orally administered sustained- release hydromorphone in humans. | 2001 Jan |
|
Opioid equianalgesic conversion: the right dose. | 2001 Jul-Aug |
|
Postoperative pain control using epidural catheters after anterior spinal fusion for adolescent scoliosis. | 2001 Jun 1 |
|
A dual epidural catheter technique to provide analgesia following posterior spinal fusion for scoliosis in children and adolescents. | 2001 Mar |
|
Intravenous methadone in the management of chronic cancer pain: safe and effective starting doses when substituting methadone for fentanyl. | 2001 Oct 1 |
|
Effects of buprenorphine sublingual tablet maintenance on opioid drug-seeking behavior by humans. | 2002 Apr |
|
A convenient synthesis of delta(7,8)-morphinan-6-one and its direct oxidation to 14-hydroxy-delta(7,8)-morphinan-6-one. | 2002 Aug 5 |
|
Epidural and intrathecal analgesia for cancer pain. | 2002 Dec |
|
New directions in pain management. | 2002 Feb |
|
Blockade of hydromorphone effects by buprenorphine/naloxone and buprenorphine. | 2002 Jan |
|
The role of spinal opioid receptors in antinociceptive effects produced by intrathecal administration of hydromorphone and buprenorphine in the rat. | 2002 Jun |
|
Dose conversion and titration with a novel, once-daily, OROS osmotic technology, extended-release hydromorphone formulation in the treatment of chronic malignant or nonmalignant pain. | 2002 May |
|
Pain and suffering in an adolescent with neuroblastoma. | 2002 May-Jun |
|
Input characteristics and bioavailability after administration of immediate and a new extended-release formulation of hydromorphone in healthy volunteers. | 2002 Oct |
|
Summary version of the Standards, Options and Recommendations for the use of analgesia for the treatment of nociceptive pain in adults with cancer (update 2002). | 2003 Aug |
|
Is the analgesic effect of systemic lidocaine mediated through opioid receptors? | 2003 Aug |
|
Postoperative hypoxemia and hypercarbia in healthy dogs undergoing routine ovariohysterectomy or castration and receiving butorphanol or hydromorphone for analgesia. | 2003 Feb 1 |
|
Quantification of the O- and N-demethylated metabolites of hydrocodone and oxycodone in human liver microsomes using liquid chromatography with ultraviolet absorbance detection. | 2003 Feb 25 |
|
Long-term outcomes during treatment of chronic pain with intrathecal clonidine or clonidine/opioid combinations. | 2003 Jul |
Sample Use Guides
Subcutaneous or Intramuscular Administration: The usual starting dose of DILAUDID INJECTION is 1 mg to 2 mg every 2 to 3 hours as necessary. Depending on the clinical situation, the initial starting dose may be lowered in patients who are opioid naïve.
Intravenous Administration: The initial starting dose is 0.2 to 1 mg every 2 to 3 hours. Intravenous administration should be given slowly, over at least 2 to 3 minutes, depending on the dose. The initial dose should be reduced in the elderly or debilitated and may be lowered to 0.2 mg.
Route of Administration:
Other
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Classification Tree | Code System | Code | ||
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FDA ORPHAN DRUG |
499415
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NCI_THESAURUS |
C67413
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NCI_THESAURUS |
C1506
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C436
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200-762-6
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CHEMBL398707
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L960UP2KRW
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117862
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m6110
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SUB02573MIG
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203177
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100000090577
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1323000
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5462347
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L960UP2KRW
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71-68-1
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5791
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DBSALT000444
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DTXSID90991291
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ACTIVE MOIETY
SUBSTANCE RECORD