Identification

Name
Hydromorphone
Accession Number
DB00327  (APRD01021)
Type
Small Molecule
Groups
Approved, Illicit
Description

An opioid analgesic derived from morphine and used mainly as an analgesic. It has a shorter duration of action and is more potent than morphine.

Structure
Thumb
Synonyms
  • (-)-(5R)-4,5-Epoxy-3-hydroxy-9α-methylmorphinan-6-one
  • 4,5-Epoxy-3-hydroxy-17-methylmorphinan-6-one
  • 4,5alpha-Epoxy-3-hydroxy-17-methyl-6-morphinanone
  • 6-Deoxy-7,8-dihydro-6-oxomorphine
  • 7,8-Dihydromorphinone
  • Dihydromorfinon
  • Dihydromorphinone
  • Dimorphone
  • Hidromorfona
  • Hydromorfona
  • Hydromorphone
  • Hydromorphonum
  • Idromorfone
External IDs
IDS-NH-004 / N02AA03 / NSC-19046
Product Ingredients
IngredientUNIICASInChI Key
Hydromorphone hydrochlorideL960UP2KRW71-68-1XHILEZUETWRSHC-NRGUFEMZSA-N
Hydromorphone sulfate75Y990NH3Z25333-57-7JBBINZRUTLUBFR-NRGUFEMZSA-N
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
DilaudidTablet4 mg/1OralPhysicians Total Care, Inc.2004-10-112013-06-30Us
DilaudidTablet2 mg/1OralPurdue Pharma LP1956-01-01Not applicableUs
DilaudidInjection, solution4 mg/1mLIntramuscular; Intravenous; SubcutaneousPurdue Pharma LP1926-01-01Not applicableUs
DilaudidInjection, solution1 mg/1mLIntramuscular; Intravenous; SubcutaneousFresenius Kabi2016-12-16Not applicableUs
DilaudidInjection, solution4 mg/1mLIntramuscular; Intravenous; SubcutaneousFresenius Kabi USA, LLC2016-12-162016-12-31Us
DilaudidTablet4 mg/1OralRhodes Pharmaceuticals L.P.2017-05-15Not applicableUs
DilaudidInjection, solution4 mg/1mLIntramuscular; Intravenous; SubcutaneousPhysicians Total Care, Inc.2004-08-132011-06-30Us
DilaudidTablet4 mg/1OralCardinal Health1926-01-01Not applicableUs
DilaudidTablet8 mg/1OralPurdue Pharma LP1956-01-01Not applicableUs
DilaudidSolution5 mg/5mLOralRhodes Pharmaceuticals L.P.2017-05-15Not applicableUs
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-hydromorphoneTablet1 mgOralApotex Corporation2012-12-18Not applicableCanada
Apo-hydromorphoneTablet4 mgOralApotex Corporation2012-12-18Not applicableCanada
Apo-hydromorphoneTablet2 mgOralApotex Corporation2012-12-18Not applicableCanada
Apo-hydromorphoneTablet8 mgOralApotex Corporation2012-12-18Not applicableCanada
Bar-hydromorphone HClCapsule, extended release24 mgOralBard Pharmaceuticals (1990) IncNot applicableNot applicableCanada
Bar-hydromorphone HClCapsule, extended release3 mgOralBard Pharmaceuticals (1990) IncNot applicableNot applicableCanada
Bar-hydromorphone HClCapsule, extended release6 mgOralBard Pharmaceuticals (1990) IncNot applicableNot applicableCanada
Bar-hydromorphone HClCapsule, extended release12 mgOralBard Pharmaceuticals (1990) IncNot applicableNot applicableCanada
Bar-hydromorphone HClCapsule, extended release4.5 mgOralBard Pharmaceuticals (1990) IncNot applicableNot applicableCanada
Bar-hydromorphone HClCapsule, extended release30 mgOralBard Pharmaceuticals (1990) IncNot applicableNot applicableCanada
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Hydromorphone HClHydromorphone hydrochloride (1 mg/1mL)Injection, solutionIntravenousCantrell Drug Company2012-08-302017-12-06Us
Hydromorphone HClHydromorphone hydrochloride (0.1 mg/1mL)Injection, solutionIntravenousCantrell Drug Company2014-08-21Not applicableUs
Hydromorphone HClHydromorphone hydrochloride (2 mg/1mL)Injection, solutionIntravenousCantrell Drug Company2014-08-13Not applicableUs
Hydromorphone HClHydromorphone hydrochloride (0.4 mg/1mL)Injection, solutionIntravenousCantrell Drug Company2014-08-13Not applicableUs
Hydromorphone HClHydromorphone hydrochloride (0.2 mg/1mL)Injection, solutionIntravenousCantrell Drug Company2010-08-232017-12-06Us
Hydromorphone HClHydromorphone hydrochloride (0.5 mg/1mL)Injection, solutionIntravenousCantrell Drug Company2014-08-13Not applicableUs
Hydromorphone HClHydromorphone hydrochloride (10 mg/1mL)Injection, solutionIntravenousCantrell Drug Company2014-08-13Not applicableUs
Hydromorphone HydrochlorideHydromorphone hydrochloride (2 mg/1mL)InjectionIntramuscular; Intravenous; SubcutaneousWest Ward Pharmaceutical1972-01-01Not applicableUs
Hydromorphone HydrochlorideHydromorphone hydrochloride (2 mg/1mL)InjectionIntramuscular; Intravenous; SubcutaneousWest Ward Pharmaceutical1972-01-01Not applicableUs
Hydromorphone HydrochlorideHydromorphone hydrochloride (3 mg/1)SuppositoryRectalPaddock Laboratories, LLC1996-01-31Not applicableUs
International/Other Brands
Palladone
Categories
UNII
Q812464R06
CAS number
466-99-9
Weight
Average: 285.3377
Monoisotopic: 285.136493479
Chemical Formula
C17H19NO3
InChI Key
WVLOADHCBXTIJK-YNHQPCIGSA-N
InChI
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
IUPAC Name
(1S,5R,13R,17R)-10-hydroxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7(18),8,10-trien-14-one
SMILES
[H][C@@]12OC3=C(O)C=CC4=C3[C@@]11CCN(C)[C@]([H])(C4)[C@]1([H])CCC2=O

Pharmacology

Indication

For the relief of moderate to severe pain such as that due to surgery, cancer, trauma/injury, or burns.

Associated Conditions
Pharmacodynamics

Hydromorphone is a hydrogenated ketone derivative of morphine that acts as a narcotic analgesic. It has a shorter duration of action than morphine. Hydromorphone is approximately 8 times more potent on a milligram basis than morphine. In addition, hydromorphone is better absorbed orally than is morphine. In clinical settings, Hydromorphone exerts its principal pharmacological effect on the central nervous system and gastrointestinal tract. Its primary actions of therapeutic value are analgesia and sedation. Hydromorphone appears to increase the patient's tolerance for pain and to decrease discomfort, although the presence of the pain itself may still be recognized. In addition to analgesia, alterations in mood, euphoria and dysphoria, and drowsiness commonly occur. Opioids also produce respiratory depression by direct action on brain stem respiratory centers.

Mechanism of action

Hydromorphone is a narcotic analgesic; its principal therapeutic effect is relief of pain. 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. They are also found on the terminal axons of primary afferents within laminae I and II (substantia gelatinosa) of the spinal cord and in the spinal nucleus of the trigeminal nerve. In clinical settings, Hydromorphone exerts its principal pharmacological effect on the central nervous system and gastrointestinal tract. Hydromorphone also binds with kappa-receptors which are thought to mediate spinal analgesia, miosis and sedation.

TargetActionsOrganism
AMu-type opioid receptor
agonist
Human
ADelta-type opioid receptor
partial agonist
Human
AKappa-type opioid receptor
agonist
Human
Absorption

Better absorbed orally than morphine

Volume of distribution
Not Available
Protein binding

20%

Metabolism

Primarily hepatic. After absorption hydromorphone is metabolized by the liver to the glucuronide conjugate which is then excreted in the urine. Hydromorphone is metabolized to the major metabolites hydromorphone-3-glucuronide, hydromorphone-3-glucoside and dihydroisomorphine-6-glucuronide.

Route of elimination

Only a small amount of the hydromorphone dose is excreted unchanged in the urine. Most of the dose is excreted as hydromorphone-3-glucuronide along with minor amounts of 6-hydroxy reduction metabolites.

Half life

2.6 hours (oral); 18.6 hours for sustained release Palladone

Clearance
  • 1.96 L/min
Toxicity

Hydromorphone is a schedule II narcotic which can lead to physical dependence or addiction. High doses lead to respiratory depression, nausea, and vomiting. Overdoses lead to extreme somnolence progressing to stupor or coma, skeletal muscle flaccidity, cold and clammy skin, and sometimes bradycardia and hypotension. In severe overdosage, apnea, circulatory collapse, cardiac arrest and death may occur.

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Hydromorphone Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe metabolism of (R)-warfarin can be decreased when combined with Hydromorphone.
(S)-WarfarinThe metabolism of (S)-Warfarin can be decreased when combined with Hydromorphone.
2,5-Dimethoxy-4-ethylamphetamineThe risk or severity of serotonin syndrome can be increased when Hydromorphone is combined with 2,5-Dimethoxy-4-ethylamphetamine.
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of serotonin syndrome can be increased when Hydromorphone is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
3,4-MethylenedioxyamphetamineThe risk or severity of serotonin syndrome can be increased when Hydromorphone is combined with 3,4-Methylenedioxyamphetamine.
3,5-diiodothyropropionic acidThe metabolism of 3,5-diiodothyropropionic acid can be decreased when combined with Hydromorphone.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of serotonin syndrome can be increased when Hydromorphone is combined with 4-Bromo-2,5-dimethoxyamphetamine.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be decreased when combined with Hydromorphone.
4-MethoxyamphetamineThe risk or severity of adverse effects can be increased when Hydromorphone is combined with 4-Methoxyamphetamine.
5-androstenedioneThe metabolism of 5-androstenedione can be decreased when combined with Hydromorphone.
Food Interactions
  • Take without regard to meals. Avoid alcohol.

References

Synthesis Reference

Anne M. Hailes, Christopher E. French, Neil C. Bruce, "Morphinone reductase for the preparation of hydromorphone and hydrocodone." U.S. Patent US5571685, issued November, 1990.

US5571685
General References
  1. Coda BA, Rudy AC, Archer SM, Wermeling DP: Pharmacokinetics and bioavailability of single-dose intranasal hydromorphone hydrochloride in healthy volunteers. Anesth Analg. 2003 Jul;97(1):117-23, table of contents. [PubMed:12818953]
  2. Vallner JJ, Stewart JT, Kotzan JA, Kirsten EB, Honigberg IL: Pharmacokinetics and bioavailability of hydromorphone following intravenous and oral administration to human subjects. J Clin Pharmacol. 1981 Apr;21(4):152-6. [PubMed:6165742]
External Links
Human Metabolome Database
HMDB0014472
KEGG Compound
C07042
PubChem Compound
5284570
PubChem Substance
46508700
ChemSpider
4447624
BindingDB
50241341
ChEBI
5790
ChEMBL
CHEMBL398707
Therapeutic Targets Database
DAP000472
PharmGKB
PA449918
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Hydromorphone
ATC Codes
N02AA03 — HydromorphoneN02AG04 — Hydromorphone and antispasmodics
AHFS Codes
  • 28:08.08 — Opiate Agonists
FDA label
Download (78.9 KB)
MSDS
Download (48.3 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0CompletedTreatmentLumbar Spinal Instability / Lumbar Spine Degeneration / Spinal Stenosis of Lumbar Region1
0RecruitingSupportive CareMetastatic Malignant Neoplasm / Neoplasms, Malignant / Pain NOS1
0RecruitingTreatmentPain NOS1
1CompletedNot AvailableHealthy Volunteers1
1CompletedNot AvailableHeroin Dependence / Opioid-Related Disorders1
1CompletedTreatmentAddictions / Opioid Dependence / Pain NOS1
1CompletedTreatmentHealthy Volunteers1
1CompletedTreatmentOpioid-Related Disorders / Pain, Chronic1
1CompletedTreatmentPain NOS1
1CompletedTreatmentPain NOS / Pain, Acute1
1CompletedTreatmentSubstance Abuse1
1, 2CompletedTreatmentOpioid Abuse / Opioid Addiction / Stimulant Abuse / Stimulant Addiction1
1, 2TerminatedTreatmentWound Healing1
2Active Not RecruitingTreatmentAdenotonsillitis / Tonsillitis1
2CompletedNot AvailableHeroin Dependence / Opioid-Related Disorders1
2CompletedTreatmentCesarean Section / Pain NOS1
2CompletedTreatmentLabour Pain1
2CompletedTreatmentOpiate Dependence1
2CompletedTreatmentOpioid Use Disorders1
2CompletedTreatmentPain NOS2
2CompletedTreatmentPain, Acute1
2CompletedTreatmentPostoperative pain1
2Not Yet RecruitingTreatmentMusculoskeletal Injuries1
2RecruitingBasic ScienceOpioid Abuse / Opioid-use Disorder1
2RecruitingTreatmentChronic Lymphocytic Leukaemia (CLL)1
2RecruitingTreatmentPain, Acute1
2WithdrawnTreatmentHb-SS Disease With Vasoocclusive Pain / Hemoglobin SS Disease With Crisis / Hemoglobin SS Disease With Vasoocclusive Crisis / Other Sickle Cell Disease With Vaso-Occlusive Pain / Sickle Cell Disorders1
2, 3CompletedSupportive CareChronic Obstructive Pulmonary Disease (COPD)1
2, 3CompletedTreatmentPain, Acute1
3CompletedSupportive CareManagement of Chronic Pain1
3CompletedSupportive CarePain NOS / Prostate Cancer1
3CompletedTreatmentHeroin Dependence / Opioid Dependence1
3CompletedTreatmentPain NOS2
3CompletedTreatmentPain, Acute2
3CompletedTreatmentPain, Chronic1
3Not Yet RecruitingTreatmentPain, Acute1
3Not Yet RecruitingTreatmentPain, Cancer1
3RecruitingSupportive CareBreast - Female1
3RecruitingSupportive CareIntraoperative Complications / Malignant Female Reproductive System Neoplasm / Pain NOS1
3RecruitingTreatmentDiseases of Liver1
3RecruitingTreatmentPain, Chronic1
3TerminatedTreatmentBack Pain / Lumbar Spine Fusion / Pain NOS1
3TerminatedTreatmentChronic Non-Malignant Pain1
3TerminatedTreatmentFracture Bone / Pain, Acute / Trauma, Multiple1
3Unknown StatusSupportive CareMalignancies / Pain NOS1
3Unknown StatusTreatmentBreakthrough Cancer Pain1
3WithdrawnTreatmentMucositis1
4Active Not RecruitingSupportive CareAdvanced Cancers / Pain NOS1
4Active Not RecruitingTreatmentPostoperative pain1
4Active Not RecruitingTreatmentObstetrical analgesia therapy1
4CompletedBasic ScienceHealthy Volunteers1
4CompletedSupportive CareSickle Cell Disorders1
4CompletedTreatmentAbdominal Pain (AP)1
4CompletedTreatmentAcute Postoperative Pain1
4CompletedTreatmentAcute Postoperative Pain / Chronic Persistent Surgical Pain / Hydromorphone Use / Patients Satisfaction1
4CompletedTreatmentBack Pain Lower Back1
4CompletedTreatmentBreakthrough Pain / Pain, Chronic / Pain, Intractable1
4CompletedTreatmentCesarean Section / Obstetrical analgesia therapy1
4CompletedTreatmentLabour Pain1
4CompletedTreatmentMigraines1
4CompletedTreatmentNarcotic Use / Nausea / Occasional Constipation / Pain NOS1
4CompletedTreatmentNausea1
4CompletedTreatmentPain NOS4
4CompletedTreatmentPain, Acute2
4CompletedTreatmentPain, Cancer1
4CompletedTreatmentPain, Neuropathic1
4CompletedTreatmentPost Operative Pain1
4CompletedTreatmentPostoperative pain3
4CompletedTreatmentPostoperative pain / Thoracic Surgery, Video-Assisted1
4CompletedTreatmentUnilateral Knee Arthroplasty1
4CompletedTreatmentAcute, severe Pain1
4Not Yet RecruitingTreatmentAnalgesics, Opioid / Anti-Inflammatory Agents, Non-Steroidal / Child/Adolescent Problems / Emergency Service, Hospital / Fentanyl / Ibuprofen / Pain, Acute1
4Not Yet RecruitingTreatmentPostoperative pain1
4RecruitingPreventionCaesarean Sections1
4RecruitingPreventionPain NOS / Rotator Cuff Injury1
4RecruitingSupportive CareColon Diverticulosis / Colonic Neoplasms / Constipation Drug Induced / Diverticulitis, Colonic / Ileus / Ileus paralytic / Ileus; Mechanical / Malignant Neoplasm of Colon / Occasional Constipation / Postoperative pain / Rectum Cancer / Rectum Neoplasm1
4RecruitingTreatmentBMI >30 kg/m2 / Postoperative pain / Respiratory Insufficiency1
4RecruitingTreatmentBody Weight Changes / Post-Operative Nausea and Vomiting (PONV) / Postoperative Hemorrhages / Postoperative pain1
4RecruitingTreatmentFusion of Spine, Lumbar Region1
4RecruitingTreatmentOpioids Use / Postoperative pain1
4RecruitingTreatmentPain NOS1
4RecruitingTreatmentPectus Excavatum1
4RecruitingTreatmentRib Fracture Multiple / Rib Fractures1
4TerminatedTreatmentPain NOS1
4Unknown StatusNot AvailableAdults / Healthy Volunteers / Humans / Parturient1
4WithdrawnTreatmentPain, Acute / Postoperative pain / Surgery, Colorectal1
Not AvailableActive Not RecruitingTreatmentPain NOS / Post Operative Nausea and Vomiting (PONV)1
Not AvailableActive Not RecruitingTreatmentRib Fractures1
Not AvailableCompletedNot AvailableBreakthrough Cancer Pain / Pain, Cancer / Pain, Neuropathic / Tumors1
Not AvailableCompletedNot AvailableCancer of the Ovary / Cervical Cancers / Endometrial Cancers / Fallopian Tube Cancer / Pain NOS / Perioperative/Postoperative Complications / Sarcomas1
Not AvailableCompletedNot AvailableGeneral Surgery1
Not AvailableCompletedBasic ScienceHealthy Volunteers1
Not AvailableCompletedPreventionPost-Operative Nausea and Vomiting (PONV)1
Not AvailableCompletedSupportive CarePain Measurement / Visual Analog Pain Scale1
Not AvailableCompletedTreatmentBack Pain Lower Back1
Not AvailableCompletedTreatmentCancer, Breast1
Not AvailableCompletedTreatmentConditions Requiring Colorectal Surgery1
Not AvailableCompletedTreatmentEpidural Analgesia1
Not AvailableCompletedTreatmentObstetric Surgical Procedures / Obstetrical analgesia therapy1
Not AvailableCompletedTreatmentOpioid-Related Disorders1
Not AvailableCompletedTreatmentPost Operative Pain1
Not AvailableNot Yet RecruitingPreventionCaudal epidural block therapy / Postoperative pain / Surgery, Cardiac1
Not AvailableRecruitingNot AvailableAcute Bacterial Exacerbation of Chronic Bronchitis (ABECB) / Acute Bacterial Sinusitis (ABS) / Acute Decompensated Heart Failure (ADHF) / Acute Pyelonephritis / Adenovirus / Adjunct to general anesthesia therapy / Adrenal Insufficiency / Airway Swelling / Anaesthesia therapy / Anxiolysis / Arterial Hypotension / Autism, Early Infantile / Autistic Disorder / Bartonellosis / Benzodiazepine Withdrawal / Benzodiazepines / Bipolar Disorder (BD) / Bloodstream Infections / Bone and Joint Infections / Brain Swelling / Bronchospasm / Brucellosis / Cardiac Arrest / Central Nervous System Infections / Cholera / Chronic Bacterial Prostatitis / Community Acquired Pneumonia (CAP) / Complicated Urinary Tract Infections / Convulsions / Cytomegalovirus Retinitis / Drug hypersensitivity reaction / Early-onset Schizophrenia Spectrum Disorders / Edema / Epilepsies / Feeling Anxious / Flu caused by Influenza / Gastroparesis / Gynaecological infection / Headaches / Herpes Simplex Virus / High Blood Pressure (Hypertension) / High Cholesterol / Hospital-acquired bacterial pneumonia / Hyperlipidemias / Infantile Hemangiomas / Infection NOS / Inflammatory Conditions / Inflammatory Reaction / Influenza Treatment or Prophylaxis / Inhalational Anthrax (Post-Exposure) / Intra-Abdominal Infections / Life-threatening Fungal Infections / Lower Respiratory Tract Infection (LRTI) / Meningitis, Bacterial / Migraines / Muscle Spasms / Nausea / Opioid Addiction / Pain NOS / Plague / Pneumonia / Prophylaxis / Psittacosis / Q Fever / Reflux / Relapsing Fever / Rocky Mountain Spotted Fever / Schizophrenic Disorders / Sedation therapy / Seizures / Sepsis / Skeletal Muscle Spasms / Skin and Subcutaneous Tissue Bacterial Infections / Skin Structures and Soft Tissue Infections / Stable Angina (SA) / Thromboprophylaxis / Thrombotic events / Toxic effect of hydrocyanic acid and cyanides / Trachoma / Treatment-resistant Schizophrenia / Tularemia / Typhus Fever / Uncomplicated Skin and Skin Structure Infections / Uncomplicated Urinary Tract Infections / Urinary Tract Infections (UTIs) / Vomiting / Withdrawal1
Not AvailableRecruitingNot AvailableAnaesthesia therapy / Pain NOS1
Not AvailableRecruitingPreventionPostoperative pain1
Not AvailableRecruitingPreventionPregnancy1
Not AvailableRecruitingTreatmentNausea / Pain NOS1
Not AvailableTerminatedSupportive CarePain NOS / Respiratory Depression1
Not AvailableTerminatedTreatmentLaparoscopic Colorectal Resection1
Not AvailableUnknown StatusTreatmentPain NOS1
Not AvailableWithdrawnTreatmentPain NOS / Ventilatory Depression1

Pharmacoeconomics

Manufacturers
  • Purdue pharma lp
  • Purdue pharmaceutical products lp
  • Akorn inc
  • Barr laboratories inc
  • Hospira inc
  • Watson laboratories inc
  • Roxane laboratories inc
  • Mallinckrodt inc
  • Actavis totowa llc
  • Kv pharmaceutical co
  • Lannett holdings inc
  • Tyco healthcare mallinckrodt
Packagers
  • Abbott Laboratories Ltd.
  • Akorn Inc.
  • Barr Pharmaceuticals
  • BASF Corp.
  • Baxter International Inc.
  • Blenheim Pharmacal
  • Bristol-Myers Squibb Co.
  • Cardinal Health
  • D.M. Graham Laboratories Inc.
  • Direct Dispensing Inc.
  • Endo Pharmaceuticals Inc.
  • Ethex Corp.
  • Hospira Inc.
  • KV Pharmaceutical Co.
  • Lake Erie Medical and Surgical Supply
  • Lannett Co. Inc.
  • Mallinckrodt Inc.
  • Mckesson Corp.
  • Nucare Pharmaceuticals Inc.
  • Paddock Labs
  • PD-Rx Pharmaceuticals Inc.
  • Pharmakon
  • Pharmedium
  • Physicians Total Care Inc.
  • Purdue Pharma LP
  • Qualitest
  • Rhodes Pharmaceutical LP
  • Roxane Labs
  • Stat Rx Usa
Dosage forms
FormRouteStrength
Capsule, extended releaseOral9 mg
Injection, solutionIntramuscular; Intravenous; Subcutaneous1 mg/1mL
Injection, solutionIntramuscular; Intravenous; Subcutaneous2 mg/1mL
Injection, solutionIntramuscular; Intravenous; Subcutaneous4 mg/1mL
LiquidIntramuscular; Intravenous; Subcutaneous2 mg
LiquidOral1 mg
LiquidOral5 mg/5mL
Powder, for solutionIntramuscular; Intravenous; Subcutaneous250 mg
SolutionOral5 mg/5mL
Injection, powder, lyophilized, for solutionIntramuscular; Intravenous; Subcutaneous10 mg/1mL
LiquidIntramuscular; Intravenous; Subcutaneous10 mg
PowderIntramuscular; Intravenous; Subcutaneous250 mg/25mL
SolutionIntramuscular; Intravenous; Subcutaneous500 mg/50mL
LiquidIntramuscular; Intravenous; Subcutaneous50 mg
Tablet, extended releaseOral12 mg/1
Tablet, extended releaseOral16 mg/1
Tablet, extended releaseOral8 mg/1
Capsule, extended releaseOral4.5 mg
Capsule, extended releaseOral12 mg
Capsule, extended releaseOral18 mg
Capsule, extended releaseOral24 mg
Capsule, extended releaseOral30 mg
Capsule, extended releaseOral3 mg
Capsule, extended releaseOral6 mg
Injection, solutionIntravenous0.1 mg/1mL
Injection, solutionIntravenous0.2 mg/1mL
Injection, solutionIntravenous0.4 mg/1mL
Injection, solutionIntravenous0.5 mg/1mL
Injection, solutionIntravenous1 mg/1mL
Injection, solutionIntravenous10 mg/1mL
Injection, solutionIntravenous2 mg/1mL
SolutionOral5 mg/1mL
SolutionIntramuscular; Intravenous; Subcutaneous10 mg
SolutionIntramuscular; Intravenous; Subcutaneous20 mg
SolutionIntramuscular; Intravenous; Subcutaneous50 mg
SolutionIntramuscular; Intravenous; Subcutaneous1000 mg
InjectionIntramuscular; Intravenous; Subcutaneous2 mg/1mL
InjectionParenteral10 mg/1mL
Injection, solutionIntramuscular; Intravenous; Subcutaneous10 mg/1mL
SolutionOral1 mg/1mL
SuppositoryRectal3 mg/1
TabletOral2 mg/1
TabletOral4 mg/1
TabletOral8 mg/1
Tablet, film coatedOral2 mg/1
Tablet, film coatedOral4 mg/1
Tablet, film coatedOral8 mg/1
Tablet, film coated, extended releaseOral12 mg/1
Tablet, film coated, extended releaseOral16 mg/1
Tablet, film coated, extended releaseOral8 mg/1
Tablet, extended releaseOral32 mg/1
SolutionIntramuscular; Intravenous; Subcutaneous100 mg
SolutionIntramuscular; Intravenous; Subcutaneous2 mg
Tablet, extended releaseOral16 mg
Tablet, extended releaseOral32 mg
Tablet, extended releaseOral4 mg
Tablet, extended releaseOral8 mg
Capsule, extended releaseOral12 mg/1
Capsule, extended releaseOral16 mg/1
Capsule, extended releaseOral24 mg/1
Capsule, extended releaseOral32 mg/1
Capsule, extended releaseOral16 mg
SyrupOral1 mg
SuppositoryRectal3 mg
TabletOral1 mg
TabletOral2 mg
TabletOral4 mg
TabletOral8 mg
Prices
Unit descriptionCostUnit
Hydromorphone hcl powder166.25USD g
Dilaudid-hp 250 mg vial114.8USD vial
Dilaudid Sterile Powder 250 mg/vial78.99USD vial
HYDROmorphone HCl 6 3 mg Suppository Box54.92USD box
Hydromorphone Hp 50 50 mg/ml13.78USD ml
Dilaudid-Xp 50 mg/ml11.82USD ml
Hydromorphone 3 mg suppository11.11USD suppository
Dilaudid-Hp-Plus 20 mg/ml5.08USD ml
Hydromorphone Hp 20 20 mg/ml4.72USD ml
Hydromorph Contin 30 mg Controlled-Release Capsule4.21USD capsule
Hydromorph Contin 24 mg Controlled-Release Capsule3.52USD capsule
Dilaudid-Hp 10 mg/ml3.14USD ml
Hydromorphone Hp 10 mg/ml2.92USD ml
Hydromorph Contin 18 mg Controlled-Release Capsule2.75USD capsule
Hydromorphone 10 mg/ml ampul2.58USD ml
Pms-Hydromorphone 3 mg Suppository2.42USD suppository
Dilaudid 4 mg/ml ampul2.2USD ml
Dilaudid 8 mg tablet2.19USD tablet
HYDROmorphone HCl 4 mg/ml Solution 1ml Cartridge2.07USD cartridge
Hydromorph Contin 12 mg Controlled-Release Capsule1.91USD capsule
Dilaudid 2 mg/ml ampul1.81USD ml
Dilaudid 1 mg/ml ampul1.64USD ml
Hydromorphone hcl 8 mg tablet1.4USD tablet
Dilaudid 4 mg tablet1.36USD tablet
Hydromorphone 8 mg tablet1.32USD tablet
Dilaudid 2 mg/ml1.28USD ml
Hydromorphone 2 mg/ml1.19USD ml
Hydromorph Contin 6 mg Controlled-Release Capsule1.1USD capsule
Hydromorphone-ns 0.4 mg/ml1.08USD ml
Hydromorphone-ns 0.3 mg/ ml1.05USD ml
Hydromorphone 2 mg/ml vial1.02USD ml
Hydromorphone-ns 25 mg/25 ml1.01USD ml
Dilaudid 2 mg tablet1.0USD tablet
Hydromorphone-ns 2.5 mg/25 ml0.96USD ml
HYDROmorphone HCl 4 mg tablet0.8USD tablet
HYDROmorphone HCl 2 mg tablet0.77USD tablet
Hydromorph Contin 3 mg Controlled-Release Capsule0.73USD capsule
Hydromorphone 4 mg tablet0.72USD tablet
Dilaudid 8 mg Tablet0.55USD tablet
Hydromorphone-ns 0.2 mg/ml0.49USD ml
Hydromorphone 2 mg tablet0.37USD tablet
Pms-Hydromorphone 8 mg Tablet0.37USD tablet
Dilaudid 4 mg Tablet0.35USD tablet
Dilaudid-5 1 mg/ml liquid0.33USD ml
Hydromorphone-ns 5.5 mg/55 ml0.33USD ml
Dilaudid 2 mg Tablet0.23USD tablet
Pms-Hydromorphone 4 mg Tablet0.23USD tablet
Dilaudid 1 mg Tablet0.16USD tablet
Pms-Hydromorphone 2 mg Tablet0.15USD tablet
Pms-Hydromorphone 1 mg Tablet0.1USD tablet
Dilaudid 1 mg/ml Liquid0.09USD ml
Pms-Hydromorphone 1 mg/ml Liquid0.07USD ml
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Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5968551No1999-10-192011-12-24Us
US6589960No2003-07-082020-11-09Us
US9248229No2016-02-022034-03-12Us
US9731082No2017-08-152032-04-23Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)266.5 °CPhysProp
logP0.9Not Available
Predicted Properties
PropertyValueSource
Water Solubility4.39 mg/mLALOGPS
logP1.69ALOGPS
logP1.62ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)10.11ChemAxon
pKa (Strongest Basic)8.59ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area49.77 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity78.26 m3·mol-1ChemAxon
Polarizability30.02 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9931
Caco-2 permeable+0.8647
P-glycoprotein substrateSubstrate0.8174
P-glycoprotein inhibitor INon-inhibitor0.8497
P-glycoprotein inhibitor IINon-inhibitor0.9641
Renal organic cation transporterInhibitor0.6374
CYP450 2C9 substrateNon-substrate0.7925
CYP450 2D6 substrateSubstrate0.8618
CYP450 3A4 substrateSubstrate0.7571
CYP450 1A2 substrateNon-inhibitor0.6918
CYP450 2C9 inhibitorNon-inhibitor0.9539
CYP450 2D6 inhibitorNon-inhibitor0.5197
CYP450 2C19 inhibitorNon-inhibitor0.8088
CYP450 3A4 inhibitorNon-inhibitor0.8177
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9413
Ames testNon AMES toxic0.7214
CarcinogenicityNon-carcinogens0.9554
BiodegradationNot ready biodegradable0.9815
Rat acute toxicity2.9191 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8906
hERG inhibition (predictor II)Non-inhibitor0.8992
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Mass Spectrum (Electron Ionization)MSsplash10-002r-6960000000-9f3d9b17d56e032d76c5
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as morphinans. These are polycyclic compounds with a four-ring skeleton with three condensed six-member rings forming a partially hydrogenated phenanthrene moiety, one of which is aromatic while the two others are alicyclic.
Kingdom
Organic compounds
Super Class
Alkaloids and derivatives
Class
Morphinans
Sub Class
Not Available
Direct Parent
Morphinans
Alternative Parents
Phenanthrenes and derivatives / Isoquinolones and derivatives / Tetralins / Coumarans / Aralkylamines / Alkyl aryl ethers / 1-hydroxy-2-unsubstituted benzenoids / Piperidines / Trialkylamines / Ketones
show 5 more
Substituents
Morphinan / Phenanthrene / Isoquinolone / Tetralin / Coumaran / Alkyl aryl ether / 1-hydroxy-2-unsubstituted benzenoid / Aralkylamine / Piperidine / Benzenoid
show 17 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
morphinane alkaloid, organic heteropentacyclic compound (CHEBI:5790)

Targets

Details
1. Mu-type opioid receptor
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Agonist
General Function
Voltage-gated calcium channel activity
Specific Function
Receptor for endogenous opioids such as beta-endorphin and endomorphin. Receptor for natural and synthetic opioids including morphine, heroin, DAMGO, fentanyl, etorphine, buprenorphin and methadone...
Gene Name
OPRM1
Uniprot ID
P35372
Uniprot Name
Mu-type opioid receptor
Molecular Weight
44778.855 Da
References
  1. Quigley C: Hydromorphone for acute and chronic pain. Cochrane Database Syst Rev. 2002;(1):CD003447. [PubMed:11869661]
  2. Inturrisi CE: Clinical pharmacology of opioids for pain. Clin J Pain. 2002 Jul-Aug;18(4 Suppl):S3-13. [PubMed:12479250]
  3. Sarhill N, Walsh D, Nelson KA: Hydromorphone: pharmacology and clinical applications in cancer patients. Support Care Cancer. 2001 Mar;9(2):84-96. [PubMed:11305075]
  4. Kumar P, Sunkaraneni S, Sirohi S, Dighe SV, Walker EA, Yoburn BC: Hydromorphone efficacy and treatment protocol impact on tolerance and mu-opioid receptor regulation. Eur J Pharmacol. 2008 Nov 12;597(1-3):39-45. doi: 10.1016/j.ejphar.2008.08.025. Epub 2008 Aug 30. [PubMed:18789923]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Partial agonist
General Function
Opioid receptor activity
Specific Function
G-protein coupled receptor that functions as receptor for endogenous enkephalins and for a subset of other opioids. Ligand binding causes a conformation change that triggers signaling via guanine n...
Gene Name
OPRD1
Uniprot ID
P41143
Uniprot Name
Delta-type opioid receptor
Molecular Weight
40368.235 Da
References
  1. Fang X, Larson DL, Portoghese PS: 7-spirobenzocyclohexyl derivatives of naltrexone, oxymorphone, and hydromorphone as selective opioid receptor ligands. J Med Chem. 1997 Sep 12;40(19):3064-70. [PubMed:9301669]
  2. Hennies HH, Friderichs E, Schneider J: Receptor binding, analgesic and antitussive potency of tramadol and other selected opioids. Arzneimittelforschung. 1988 Jul;38(7):877-80. [PubMed:2849950]
  3. Jiang Q, Sebastian A, Archer S, Bidlack JM: 5 beta-Methyl-14 beta-(p-nitrocinnamoylamino)-7,8-dihydromorphinone and its corresponding N-cyclopropylmethyl analog, N-cyclopropylmethylnor-5 beta-methyl-14 beta-(p-nitrocinnamoylamino)- 7,8-dihydromorphinone: mu-selective irreversible opioid antagonists. J Pharmacol Exp Ther. 1994 Mar;268(3):1107-13. [PubMed:7511163]
  4. Guay DR: Use of oral oxymorphone in the elderly. Consult Pharm. 2007 May;22(5):417-30. [PubMed:17658959]
  5. Hartvig P, Neil A, Terenius L, Antoni G, Rimland A, Ulin J, Langstrom B: Brain and plasma kinetics of the opioid 11C-hydromorphone in two macaque species. Pharmacol Toxicol. 1989 Sep;65(3):214-6. [PubMed:2478994]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Agonist
General Function
Opioid receptor activity
Specific Function
G-protein coupled opioid receptor that functions as receptor for endogenous alpha-neoendorphins and dynorphins, but has low affinity for beta-endorphins. Also functions as receptor for various synt...
Gene Name
OPRK1
Uniprot ID
P41145
Uniprot Name
Kappa-type opioid receptor
Molecular Weight
42644.665 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Gharagozlou P, Hashemi E, DeLorey TM, Clark JD, Lameh J: Pharmacological profiles of opioid ligands at kappa opioid receptors. BMC Pharmacol. 2006 Jan 25;6:3. [PubMed:16433932]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Curator comments
Data on this enzyme effect supported by 1 in vitro study.
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. Benetton SA, Borges VM, Chang TK, McErlane KM: Role of individual human cytochrome P450 enzymes in the in vitro metabolism of hydromorphone. Xenobiotica. 2004 Apr;34(4):335-44. doi: 10.1080/00498250310001657559 . [PubMed:15268978]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Prostaglandin-endoperoxide synthase activity
Specific Function
Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Involved in the constitutive production of prostanoids in particular in the stomach and platelets. In gas...
Gene Name
PTGS1
Uniprot ID
P23219
Uniprot Name
Prostaglandin G/H synthase 1
Molecular Weight
68685.82 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Retinoic acid binding
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols. Isoform 2 lacks trans...
Gene Name
UGT1A9
Uniprot ID
O60656
Uniprot Name
UDP-glucuronosyltransferase 1-9
Molecular Weight
59940.495 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]

Drug created on June 13, 2005 07:24 / Updated on December 18, 2018 09:06