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.CN1CC[C@]23[C@H]4OC5=C(O)C=CC(C[C@@H]1[C@@H]2CCC4=O)=C35
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
| Molecular Formula | C17H19NO3 |
| Molecular Weight | 285.3377 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
| Molecular Formula | ClH |
| Molecular Weight | 36.461 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
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 Date1984 |
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: |
unhealthy, 27 |
Disc. AE: Sleepiness, Nausea... AEs leading to discontinuation/dose reduction: Sleepiness Sources: Nausea |
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: |
unhealthy, 40 |
Disc. AE: Respiratory arrest... AEs leading to discontinuation/dose reduction: Respiratory arrest (grade 5) Sources: |
4 mg 4 times / day multiple, oral Recommended Dose: 4 mg, 4 times / day Route: oral Route: multiple Dose: 4 mg, 4 times / day Sources: |
unhealthy, 67.7 |
Disc. AE: Somnolence, Aspiration pneumonia... AEs leading to discontinuation/dose reduction: Somnolence (serious, 1.14%) Sources: Aspiration 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: |
unhealthy |
Disc. AE: Cardio-respiratory arrest... AEs leading to discontinuation/dose reduction: Cardio-respiratory arrest (grade 5) Sources: |
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: |
unhealthy Health Status: unhealthy Sources: |
Disc. AE: Respiratory depression... AEs leading to discontinuation/dose reduction: Respiratory depression Sources: |
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: |
unhealthy Health Status: unhealthy Sources: |
Disc. AE: Addiction, Abuse... AEs leading to discontinuation/dose reduction: Addiction Sources: Abuse 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: |
unhealthy, 27 |
| Sleepiness | Disc. AE | 540 mg single, intrathecal Overdose Dose: 540 mg Route: intrathecal Route: single Dose: 540 mg Sources: |
unhealthy, 27 |
| 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: |
unhealthy, 40 |
| Aspiration pneumonia | grade 5, 1.14% Disc. AE |
4 mg 4 times / day multiple, oral Recommended Dose: 4 mg, 4 times / day Route: oral Route: multiple Dose: 4 mg, 4 times / day Sources: |
unhealthy, 67.7 |
| Nausea and vomiting | serious, 1.14% Disc. AE |
4 mg 4 times / day multiple, oral Recommended Dose: 4 mg, 4 times / day Route: oral Route: multiple Dose: 4 mg, 4 times / day Sources: |
unhealthy, 67.7 |
| Somnolence | serious, 1.14% Disc. AE |
4 mg 4 times / day multiple, oral Recommended Dose: 4 mg, 4 times / day Route: oral Route: multiple Dose: 4 mg, 4 times / day Sources: |
unhealthy, 67.7 |
| Toxic skin eruption | serious, 1.14% Disc. AE |
4 mg 4 times / day multiple, oral Recommended Dose: 4 mg, 4 times / day Route: oral Route: multiple Dose: 4 mg, 4 times / day Sources: |
unhealthy, 67.7 |
| Cardio-respiratory arrest | grade 5 Disc. AE |
10 mg single, intravenous Overdose Dose: 10 mg Route: intravenous Route: single Dose: 10 mg Sources: |
unhealthy |
| 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: |
unhealthy Health Status: unhealthy Sources: |
| 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: |
unhealthy Health Status: unhealthy Sources: |
| 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: |
unhealthy Health Status: unhealthy Sources: |
| 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: |
unhealthy Health Status: unhealthy Sources: |
| 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: |
unhealthy Health Status: unhealthy Sources: |
| 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: |
unhealthy Health Status: unhealthy Sources: |
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 |
|---|---|---|
| Antihyperalgesic effect of simultaneously released hydromorphone and bupivacaine from polymer fibers in the rat chronic constriction injury model. | 2003-11-14 |
|
| Effects of buprenorphine maintenance dose on mu-opioid receptor availability, plasma concentrations, and antagonist blockade in heroin-dependent volunteers. | 2003-11 |
|
| [Combined use of intrathecal morphine and diclofenac suppository for postoperative analgesia after caesarean section]. | 2003-10 |
|
| The use of long-acting opioids in chronic pain management. | 2003-09 |
|
| Oral vs. i.v. hydromorphone. Add a measure of caution. | 2003-09 |
|
| Comparison of morphine and hydromorphone analysis on reversed phase columns with different diameters. | 2003-08-08 |
|
| Calculating opioid dose conversions #36. | 2003-08 |
|
| 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). | 2003-08 |
|
| Is the analgesic effect of systemic lidocaine mediated through opioid receptors? | 2003-08 |
|
| [Pain therapy with semisynthetic opioids. Patients have opioid-type side effects more rarely]. | 2003-07-10 |
|
| Long-term outcomes during treatment of chronic pain with intrathecal clonidine or clonidine/opioid combinations. | 2003-07 |
|
| Pharmacokinetics and bioavailability of single-dose intranasal hydromorphone hydrochloride in healthy volunteers. | 2003-07 |
|
| Management of postoperative pain after T6 corpectomy: use of epidural bupivacaine and sufentanil--a case report. | 2003-06 |
|
| Oral oxycodone: new preparation. No better than oral morphine. | 2003-06 |
|
| Antinociceptive effects of hydromorphone, bupivacaine and biphalin released from PLGA polymer after intrathecal implantation in rats. | 2003-05 |
|
| Opioid equianalgesic conversion: the right dose. | 2003-04-15 |
|
| Morphine and hydromorphone for postoperative analgesia: focus on safety. | 2003-04 |
|
| Embolized crospovidone (poly[N-vinyl-2-pyrrolidone]) in the lungs of intravenous drug users. | 2003-04 |
|
| Pharmacokinetic drug interactions of morphine, codeine, and their derivatives: theory and clinical reality, part I. | 2003-03-06 |
|
| Using saccadic eye movements as objective measures of tolerance in methadone dependent individuals during the hydromorphone challenge test. | 2003-03 |
|
| Changes in intraocular pressure and pupil size following intramuscular administration of hydromorphone hydrochloride and acepromazine in clinically normal dogs. | 2003-03 |
|
| Opioid ligands having delayed long-term antagonist activity: potential pharmacotherapies for opioid abuse. | 2003-03 |
|
| Quantification of the O- and N-demethylated metabolites of hydrocodone and oxycodone in human liver microsomes using liquid chromatography with ultraviolet absorbance detection. | 2003-02-25 |
|
| Postoperative hypoxemia and hypercarbia in healthy dogs undergoing routine ovariohysterectomy or castration and receiving butorphanol or hydromorphone for analgesia. | 2003-02-01 |
|
| A systematic review of hydromorphone in acute and chronic pain. | 2003-02 |
|
| Hydromorphone transfer into breast milk after intranasal administration. | 2003-02 |
|
| Activity of opioid ligands in cells expressing cloned mu opioid receptors. | 2003-01-04 |
|
| Catheter-associated masses in patients receiving intrathecal analgesic therapy. | 2003-01 |
|
| In vivo pain relief effectiveness of an analgesic-anesthetic carrying biodegradable controlled release rod systems. | 2003 |
|
| Envenomation by the Mexican beaded lizard: a case report. | 2003 |
|
| Postoperative analgesia and sedation in the adult intensive care unit: a guide to drug selection. | 2003 |
|
| Screening extemporaneously compounded intraspinal injections with the bacterial endotoxins test. | 2002-12-15 |
|
| Role of urine toxicology testing in the management of chronic opioid therapy. | 2002-12-14 |
|
| Clinical pharmacology of opioids for pain. | 2002-12-14 |
|
| Epidural and intrathecal analgesia for cancer pain. | 2002-12 |
|
| Activation profiles of opioid ligands in HEK cells expressing delta opioid receptors. | 2002-11-18 |
|
| Opioid rotation in the treatment of joint pain. A review of 67 cases. | 2002-10 |
|
| Simultaneous quantitation of opioids in blood by GC-EI-MS analysis following deproteination, detautomerization of keto analytes, solid-phase extraction, and trimethylsilyl derivatization. | 2002-10 |
|
| A field evaluation of five on-site drug-testing devices. | 2002-10 |
|
| Detection of cocaine analytes and opiates in nails from postmortem cases. | 2002-10 |
|
| Input characteristics and bioavailability after administration of immediate and a new extended-release formulation of hydromorphone in healthy volunteers. | 2002-10 |
|
| Fentanyl-associated syndrome of inappropriate antidiuretic hormone secretion. | 2002-09 |
|
| A convenient synthesis of delta(7,8)-morphinan-6-one and its direct oxidation to 14-hydroxy-delta(7,8)-morphinan-6-one. | 2002-08-05 |
|
| The addition of hydromorphone to epidural fentanyl does not affect analgesia in early labour. | 2002-06-18 |
|
| The use of methadone for cancer pain. | 2002-06 |
|
| Pain management for joint arthroplasty: preemptive analgesia. | 2002-06 |
|
| Postthoracotomy pain management. | 2002-05 |
|
| New directions in pain management. | 2002-02 |
|
| Clonazepam treatment of myoclonic contractions associated with high-dose opioids: case report. | 1992-05 |
|
| Survey of pain management therapy provided for children with sickle cell disease. | 1992-04 |
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
| Substance Class |
Chemical
Created
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admin
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Mon Mar 31 17:34:56 GMT 2025
by
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on
Mon Mar 31 17:34:56 GMT 2025
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| Record UNII |
L960UP2KRW
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| Record Status |
Validated (UNII)
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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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| Related Record | Type | Details | ||
|---|---|---|---|---|
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PARENT -> SALT/SOLVATE | |||
|
BASIS OF STRENGTH->SUBSTANCE |
ASSAY (TITRATION)
EP
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|
BASIS OF STRENGTH->SUBSTANCE |
ASSAY (TITRATION)
USP
|
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
Procedure 1 and 2
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
||
|
IMPURITY -> PARENT |
Procedure 1
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
||
|
IMPURITY -> PARENT |
Procedure 2
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
||
|
IMPURITY -> PARENT |
Procedure 2
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
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|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
Procedure 1
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
||
|
IMPURITY -> PARENT |
Procedure 1
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
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|
IMPURITY -> PARENT |
Procedure 1
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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ACTIVE MOIETY |