Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Dilaudid	Tablet	4 mg/1	Oral	Lake Erie Medical Dba Quality Care Produts Llc	1956-01-01	2013-03-26
Dilaudid	Tablet	2 mg/1	Oral	Physicians Total Care, Inc.	2003-11-11	2011-06-30
Dilaudid	Tablet	4 mg	Oral	Purdue Pharma	1984-12-31	Not applicable
Dilaudid	Injection, solution	1 mg/1mL	Intramuscular; Intravenous; Subcutaneous	Purdue Pharma LP	1926-01-01	2017-02-01
Dilaudid	Tablet	4 mg/1	Oral	Rhodes Pharmaceuticals L.P.	2017-05-15	Not applicable
Dilaudid	Tablet	2 mg/1	Oral	Purdue Pharma LP	1956-01-01	Not applicable
Dilaudid	Injection, solution	2 mg/1mL	Intramuscular; Intravenous; Subcutaneous	Fresenius Kabi USA, LLC	2016-12-16	Not applicable
Dilaudid	Liquid	5 mg/5mL	Oral	Abbvie	1992-12-07	2008-12-31
Dilaudid	Tablet	4 mg/1	Oral	Cardinal Health	1926-01-01	Not applicable
Dilaudid	Tablet	2 mg	Oral	Purdue Pharma	1984-12-31	Not applicable

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Apo-hydromorphone	Tablet	8 mg	Oral	Apotex Corporation	2012-12-18	Not applicable
Apo-hydromorphone	Tablet	4 mg	Oral	Apotex Corporation	2012-12-18	Not applicable
Apo-hydromorphone	Tablet	2 mg	Oral	Apotex Corporation	2012-12-18	Not applicable
Apo-hydromorphone	Tablet	1 mg	Oral	Apotex Corporation	2012-12-18	Not applicable
Bar-hydromorphone HCl	Capsule, extended release	9 mg	Oral	Bard Pharmaceuticals (1990) Inc	Not applicable	Not applicable
Bar-hydromorphone HCl	Capsule, extended release	24 mg	Oral	Bard Pharmaceuticals (1990) Inc	Not applicable	Not applicable
Bar-hydromorphone HCl	Capsule, extended release	6 mg	Oral	Bard Pharmaceuticals (1990) Inc	Not applicable	Not applicable
Bar-hydromorphone HCl	Capsule, extended release	18 mg	Oral	Bard Pharmaceuticals (1990) Inc	Not applicable	Not applicable
Bar-hydromorphone HCl	Capsule, extended release	4.5 mg	Oral	Bard Pharmaceuticals (1990) Inc	Not applicable	Not applicable
Bar-hydromorphone HCl	Capsule, extended release	12 mg	Oral	Bard Pharmaceuticals (1990) Inc	Not applicable	Not applicable

Unapproved/Other Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
Hydromorphone HCl	Hydromorphone hydrochloride (0.4 mg/1mL)	Injection, solution	Intravenous	Cantrell Drug Company	2014-08-13	Not applicable
Hydromorphone HCl	Hydromorphone hydrochloride (0.2 mg/1mL)	Injection, solution	Intravenous	Cantrell Drug Company	2010-08-23	2017-12-06
Hydromorphone HCl	Hydromorphone hydrochloride (0.5 mg/1mL)	Injection, solution	Intravenous	Cantrell Drug Company	2014-08-13	Not applicable
Hydromorphone HCl	Hydromorphone hydrochloride (1 mg/1mL)	Injection, solution	Intravenous	Cantrell Drug Company	2012-08-30	2017-12-06
Hydromorphone HCl	Hydromorphone hydrochloride (2 mg/1mL)	Injection, solution	Intravenous	Cantrell Drug Company	2014-08-13	Not applicable
Hydromorphone HCl	Hydromorphone hydrochloride (0.1 mg/1mL)	Injection, solution	Intravenous	Cantrell Drug Company	2014-08-21	Not applicable
Hydromorphone HCl	Hydromorphone hydrochloride (10 mg/1mL)	Injection, solution	Intravenous	Cantrell Drug Company	2014-08-13	Not applicable
Hydromorphone Hydrochloride	Hydromorphone hydrochloride (3 mg/1)	Suppository	Rectal	Paddock Laboratories, LLC	1996-01-31	Not applicable
Hydromorphone Hydrochloride	Hydromorphone hydrochloride (2 mg/1mL)	Injection	Intramuscular; Intravenous; Subcutaneous	West-Ward Pharmaceuticals Corp.	1972-01-01	Not applicable
Hydromorphone Hydrochloride	Hydromorphone hydrochloride (2 mg/1mL)	Injection	Intramuscular; Intravenous; Subcutaneous	West-Ward Pharmaceuticals Corp.	1972-01-01	Not applicable

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.

Target	Actions	Organism
AMu-type opioid receptor	agonist	Humans
ADelta-type opioid receptor	partial agonist	Humans
AKappa-type opioid receptor	agonist	Humans

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

Pathway	Category
Hydromorphone Action Pathway	Drug action

Pharmacogenomic Effects/ADRs

Not Available

Interactions

Drug Interactions

Drug	Interaction
(R)-warfarin	The metabolism of (R)-warfarin can be decreased when combined with Hydromorphone.
(S)-Warfarin	The metabolism of (S)-Warfarin can be decreased when combined with Hydromorphone.
2,5-Dimethoxy-4-ethylamphetamine	The risk or severity of serotonin syndrome can be increased when Hydromorphone is combined with 2,5-Dimethoxy-4-ethylamphetamine.
2,5-Dimethoxy-4-ethylthioamphetamine	The risk or severity of serotonin syndrome can be increased when Hydromorphone is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
3,4-Methylenedioxyamphetamine	The risk or severity of serotonin syndrome can be increased when Hydromorphone is combined with 3,4-Methylenedioxyamphetamine.
3,5-diiodothyropropionic acid	The metabolism of 3,5-diiodothyropropionic acid can be decreased when combined with Hydromorphone.
4-Bromo-2,5-dimethoxyamphetamine	The risk or severity of serotonin syndrome can be increased when Hydromorphone is combined with 4-Bromo-2,5-dimethoxyamphetamine.
4-hydroxycoumarin	The metabolism of 4-hydroxycoumarin can be decreased when combined with Hydromorphone.
4-Methoxyamphetamine	The risk or severity of adverse effects can be increased when Hydromorphone is combined with 4-Methoxyamphetamine.
5-androstenedione	The 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

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]
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 — Hydromorphone

N02AG04 — 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

Phase	Status	Purpose	Conditions	Count
0	Completed	Treatment	Lumbar Spinal Instability / Lumbar Spine Degeneration / Spinal Stenosis of Lumbar Region	1
0	Completed	Treatment	Pain NOS	1
0	Recruiting	Supportive Care	Metastatic Malignant Neoplasm / Neoplasms, Malignant / Pain NOS	1
1	Completed	Not Available	Healthy Volunteers	1
1	Completed	Not Available	Heroin Dependence / Opioid-Related Disorders	1
1	Completed	Treatment	Addictions / Opioid Dependence / Pain NOS	1
1	Completed	Treatment	Healthy Volunteers	1
1	Completed	Treatment	Opioid-Related Disorders / Pain, Chronic	1
1	Completed	Treatment	Pain NOS	1
1	Completed	Treatment	Pain NOS / Pain, Acute	1
1	Completed	Treatment	Substance Abuse	1
1, 2	Completed	Treatment	Opioid Abuse / Opioid Addiction / Stimulant Abuse / Stimulant Addiction	1
1, 2	Terminated	Treatment	Wound Healing	1
2	Active Not Recruiting	Treatment	Adenotonsillitis / Tonsillitis	1
2	Completed	Not Available	Heroin Dependence / Opioid-Related Disorders	1
2	Completed	Treatment	Cesarean Section / Pain NOS	1
2	Completed	Treatment	Labour Pain	1
2	Completed	Treatment	Opiate Dependence	1
2	Completed	Treatment	Opioid Use Disorders	1
2	Completed	Treatment	Pain NOS	2
2	Completed	Treatment	Pain, Acute	1
2	Completed	Treatment	Postoperative pain	1
2	Not Yet Recruiting	Treatment	Musculoskeletal Injuries	1
2	Recruiting	Basic Science	Opioid Abuse / Opioid-use Disorder	1
2	Recruiting	Treatment	Chronic Lymphocytic Leukaemia (CLL)	1
2	Recruiting	Treatment	Pain, Acute	1
2	Withdrawn	Treatment	Hb-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 Disorders	1
2, 3	Completed	Supportive Care	Chronic Obstructive Pulmonary Disease (COPD)	1
2, 3	Completed	Treatment	Pain, Acute	1
3	Completed	Supportive Care	Management of Chronic Pain	1
3	Completed	Supportive Care	Pain NOS / Prostate Cancer	1
3	Completed	Treatment	Heroin Dependence / Opioid Dependence	1
3	Completed	Treatment	Pain NOS	2
3	Completed	Treatment	Pain, Acute	2
3	Completed	Treatment	Pain, Chronic	1
3	Not Yet Recruiting	Treatment	Pain, Acute	1
3	Not Yet Recruiting	Treatment	Pain, Cancer	1
3	Recruiting	Supportive Care	Breast - Female	1
3	Recruiting	Supportive Care	Intraoperative Complications / Malignant Female Reproductive System Neoplasm / Pain NOS	1
3	Recruiting	Treatment	Diseases of Liver	1
3	Recruiting	Treatment	Pain, Chronic	1
3	Terminated	Treatment	Back Pain / Lumbar Spine Fusion / Pain NOS	1
3	Terminated	Treatment	Chronic Non-Malignant Pain	1
3	Terminated	Treatment	Fracture Bone / Pain, Acute / Trauma, Multiple	1
3	Unknown Status	Supportive Care	Malignancies / Pain NOS	1
3	Unknown Status	Treatment	Breakthrough Cancer Pain	1
3	Withdrawn	Treatment	Mucositis	1
4	Active Not Recruiting	Supportive Care	Advanced Cancers / Pain NOS	1
4	Active Not Recruiting	Treatment	Postoperative pain	1
4	Active Not Recruiting	Treatment	Obstetrical analgesia therapy	1
4	Completed	Basic Science	Healthy Volunteers	1
4	Completed	Supportive Care	Sickle Cell Disorders	1
4	Completed	Treatment	Abdominal Pain (AP)	1
4	Completed	Treatment	Acute Postoperative Pain	1
4	Completed	Treatment	Acute Postoperative Pain / Chronic Persistent Surgical Pain / Hydromorphone Use / Patients Satisfaction	1
4	Completed	Treatment	Back Pain Lower Back	1
4	Completed	Treatment	Breakthrough Pain / Pain, Chronic / Pain, Intractable	1
4	Completed	Treatment	Cesarean Section / Obstetrical analgesia therapy	1
4	Completed	Treatment	Labour Pain	1
4	Completed	Treatment	Migraine	1
4	Completed	Treatment	Narcotic Use / Nausea / Occasional Constipation / Pain NOS	1
4	Completed	Treatment	Nausea	1
4	Completed	Treatment	Pain NOS	4
4	Completed	Treatment	Pain, Acute	2
4	Completed	Treatment	Pain, Cancer	1
4	Completed	Treatment	Pain, Neuropathic	1
4	Completed	Treatment	Post Operative Pain	1
4	Completed	Treatment	Postoperative pain	3
4	Completed	Treatment	Postoperative pain / Thoracic Surgery, Video-Assisted	1
4	Completed	Treatment	Unilateral Knee Arthroplasty	1
4	Completed	Treatment	Acute, severe Pain	1
4	Not Yet Recruiting	Treatment	Analgesics, Opioid / Anti-Inflammatory Agents, Non-Steroidal / Child/Adolescent Problems / Emergency Service, Hospital / Fentanyl / Ibuprofen / Pain, Acute	1
4	Not Yet Recruiting	Treatment	Postoperative pain	1
4	Recruiting	Prevention	Caesarean Sections	1
4	Recruiting	Prevention	Pain NOS / Rotator Cuff Injury	1
4	Recruiting	Supportive Care	Colon Diverticulosis / Colonic Neoplasms / Constipation Drug Induced / Diverticulitis, Colonic / Ileus / Ileus paralytic / Ileus; Mechanical / Malignant Neoplasm of Colon / Occasional Constipation / Postoperative pain / Rectum Cancer / Rectum Neoplasm	1
4	Recruiting	Treatment	BMI >30 kg/m2 / Postoperative pain / Respiratory Insufficiency	1
4	Recruiting	Treatment	Body Weight Changes / Post-Operative Nausea and Vomiting (PONV) / Postoperative Hemorrhages / Postoperative pain	1
4	Recruiting	Treatment	Fusion of Spine, Lumbar Region	1
4	Recruiting	Treatment	Opioids Use / Postoperative pain	1
4	Recruiting	Treatment	Pain NOS	1
4	Recruiting	Treatment	Rib Fracture Multiple / Rib Fractures	1
4	Terminated	Treatment	Pain NOS	1
4	Terminated	Treatment	Pectus Excavatum	1
4	Unknown Status	Not Available	Adults / Healthy Volunteers / Humans / Parturient	1
4	Withdrawn	Treatment	Pain, Acute / Postoperative pain / Surgery, Colorectal	1
Not Available	Active Not Recruiting	Treatment	Pain NOS / Post Operative Nausea and Vomiting (PONV)	1
Not Available	Active Not Recruiting	Treatment	Rib Fractures	1
Not Available	Completed	Not Available	Breakthrough Cancer Pain / Pain, Cancer / Pain, Neuropathic / Tumors	1
Not Available	Completed	Not Available	Cancer of the Ovary / Cervical Cancers / Endometrial Cancers / Fallopian Tube Cancer / Pain NOS / Perioperative/Postoperative Complications / Sarcomas	1
Not Available	Completed	Not Available	General Surgery	1
Not Available	Completed	Basic Science	Healthy Volunteers	1
Not Available	Completed	Prevention	Post-Operative Nausea and Vomiting (PONV)	1
Not Available	Completed	Supportive Care	Pain Measurement / Visual Analog Pain Scale	1
Not Available	Completed	Treatment	Back Pain Lower Back	1
Not Available	Completed	Treatment	Cancer, Breast	1
Not Available	Completed	Treatment	Conditions Requiring Colorectal Surgery	1
Not Available	Completed	Treatment	Epidural Analgesia	1
Not Available	Completed	Treatment	Obstetric Surgical Procedures / Obstetrical analgesia therapy	1
Not Available	Completed	Treatment	Opioid-Related Disorders	1
Not Available	Completed	Treatment	Pain Conditions	1
Not Available	Completed	Treatment	Post Operative Pain	1
Not Available	Not Yet Recruiting	Prevention	Caudal epidural block therapy / Postoperative pain / Surgery, Cardiac	1
Not Available	Recruiting	Not Available	Acute 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 / Migraine / 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 / Withdrawal	1
Not Available	Recruiting	Not Available	Anaesthesia therapy / Pain NOS	1
Not Available	Recruiting	Prevention	Postoperative pain	1
Not Available	Recruiting	Prevention	Pregnancy	1
Not Available	Recruiting	Treatment	Nausea / Pain NOS	1
Not Available	Terminated	Supportive Care	Pain NOS / Respiratory Depression	1
Not Available	Terminated	Treatment	Laparoscopic Colorectal Resection	1
Not Available	Unknown Status	Treatment	Pain NOS	1
Not Available	Withdrawn	Treatment	Pain NOS / Ventilatory Depression	1

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

Form	Route	Strength
Capsule, extended release	Oral	9 mg
Injection, solution	Intramuscular; Intravenous; Subcutaneous	1 mg/1mL
Injection, solution	Intramuscular; Intravenous; Subcutaneous	2 mg/1mL
Injection, solution	Intramuscular; Intravenous; Subcutaneous	4 mg/1mL
Liquid	Intramuscular; Intravenous; Subcutaneous	2 mg
Liquid	Oral	1 mg
Liquid	Oral	5 mg/5mL
Powder, for solution	Intramuscular; Intravenous; Subcutaneous	250 mg
Solution	Oral	5 mg/5mL
Injection, powder, lyophilized, for solution	Intramuscular; Intravenous; Subcutaneous	10 mg/1mL
Liquid	Intramuscular; Intravenous; Subcutaneous	10 mg
Powder	Intramuscular; Intravenous; Subcutaneous	250 mg/25mL
Solution	Intramuscular; Intravenous; Subcutaneous	500 mg/50mL
Liquid	Intramuscular; Intravenous; Subcutaneous	50 mg
Tablet, extended release	Oral	12 mg/1
Tablet, extended release	Oral	16 mg/1
Tablet, extended release	Oral	32 mg/1
Tablet, extended release	Oral	8 mg/1
Capsule, extended release	Oral	4.5 mg
Capsule, extended release	Oral	12 mg
Capsule, extended release	Oral	18 mg
Capsule, extended release	Oral	24 mg
Capsule, extended release	Oral	30 mg
Capsule, extended release	Oral	3 mg
Capsule, extended release	Oral	6 mg
Injection, solution	Intravenous	0.1 mg/1mL
Injection, solution	Intravenous	0.2 mg/1mL
Injection, solution	Intravenous	0.4 mg/1mL
Injection, solution	Intravenous	0.5 mg/1mL
Injection, solution	Intravenous	1 mg/1mL
Injection, solution	Intravenous	10 mg/1mL
Injection, solution	Intravenous	2 mg/1mL
Solution	Oral	5 mg/1mL
Solution	Intramuscular; Intravenous; Subcutaneous	10 mg
Solution	Intramuscular; Intravenous; Subcutaneous	20 mg
Solution	Intramuscular; Intravenous; Subcutaneous	50 mg
Solution	Intramuscular; Intravenous; Subcutaneous	1000 mg
Injection	Intramuscular; Intravenous; Subcutaneous	2 mg/1mL
Injection	Parenteral	10 mg/1mL
Injection, solution	Intramuscular; Intravenous; Subcutaneous	10 mg/1mL
Solution	Oral	1 mg/1mL
Suppository	Rectal	3 mg/1
Tablet	Oral	2 mg/1
Tablet	Oral	4 mg/1
Tablet	Oral	8 mg/1
Tablet, film coated	Oral	2 mg/1
Tablet, film coated	Oral	4 mg/1
Tablet, film coated	Oral	8 mg/1
Tablet, film coated, extended release	Oral	12 mg/1
Tablet, film coated, extended release	Oral	16 mg/1
Tablet, film coated, extended release	Oral	8 mg/1
Solution	Intramuscular; Intravenous; Subcutaneous	100 mg
Solution	Intramuscular; Intravenous; Subcutaneous	2 mg
Tablet, extended release	Oral	16 mg
Tablet, extended release	Oral	32 mg
Tablet, extended release	Oral	4 mg
Tablet, extended release	Oral	8 mg
Capsule, extended release	Oral	12 mg/1
Capsule, extended release	Oral	16 mg/1
Capsule, extended release	Oral	24 mg/1
Capsule, extended release	Oral	32 mg/1
Capsule, extended release	Oral	16 mg
Syrup	Oral	1 mg
Suppository	Rectal	3 mg
Tablet	Oral	1 mg
Tablet	Oral	2 mg
Tablet	Oral	4 mg
Tablet	Oral	8 mg

Prices

Unit description	Cost	Unit
Hydromorphone hcl powder	166.25USD	g
Dilaudid-hp 250 mg vial	114.8USD	vial
Dilaudid Sterile Powder 250 mg/vial	78.99USD	vial
HYDROmorphone HCl 6 3 mg Suppository Box	54.92USD	box
Hydromorphone Hp 50 50 mg/ml	13.78USD	ml
Dilaudid-Xp 50 mg/ml	11.82USD	ml
Hydromorphone 3 mg suppository	11.11USD	suppository
Dilaudid-Hp-Plus 20 mg/ml	5.08USD	ml
Hydromorphone Hp 20 20 mg/ml	4.72USD	ml
Hydromorph Contin 30 mg Controlled-Release Capsule	4.21USD	capsule
Hydromorph Contin 24 mg Controlled-Release Capsule	3.52USD	capsule
Dilaudid-Hp 10 mg/ml	3.14USD	ml
Hydromorphone Hp 10 mg/ml	2.92USD	ml
Hydromorph Contin 18 mg Controlled-Release Capsule	2.75USD	capsule
Hydromorphone 10 mg/ml ampul	2.58USD	ml
Pms-Hydromorphone 3 mg Suppository	2.42USD	suppository
Dilaudid 4 mg/ml ampul	2.2USD	ml
Dilaudid 8 mg tablet	2.19USD	tablet
HYDROmorphone HCl 4 mg/ml Solution 1ml Cartridge	2.07USD	cartridge
Hydromorph Contin 12 mg Controlled-Release Capsule	1.91USD	capsule
Dilaudid 2 mg/ml ampul	1.81USD	ml
Dilaudid 1 mg/ml ampul	1.64USD	ml
Hydromorphone hcl 8 mg tablet	1.4USD	tablet
Dilaudid 4 mg tablet	1.36USD	tablet
Hydromorphone 8 mg tablet	1.32USD	tablet
Dilaudid 2 mg/ml	1.28USD	ml
Hydromorphone 2 mg/ml	1.19USD	ml
Hydromorph Contin 6 mg Controlled-Release Capsule	1.1USD	capsule
Hydromorphone-ns 0.4 mg/ml	1.08USD	ml
Hydromorphone-ns 0.3 mg/ ml	1.05USD	ml
Hydromorphone 2 mg/ml vial	1.02USD	ml
Hydromorphone-ns 25 mg/25 ml	1.01USD	ml
Dilaudid 2 mg tablet	1.0USD	tablet
Hydromorphone-ns 2.5 mg/25 ml	0.96USD	ml
HYDROmorphone HCl 4 mg tablet	0.8USD	tablet
HYDROmorphone HCl 2 mg tablet	0.77USD	tablet
Hydromorph Contin 3 mg Controlled-Release Capsule	0.73USD	capsule
Hydromorphone 4 mg tablet	0.72USD	tablet
Dilaudid 8 mg Tablet	0.55USD	tablet
Hydromorphone-ns 0.2 mg/ml	0.49USD	ml
Hydromorphone 2 mg tablet	0.37USD	tablet
Pms-Hydromorphone 8 mg Tablet	0.37USD	tablet
Dilaudid 4 mg Tablet	0.35USD	tablet
Dilaudid-5 1 mg/ml liquid	0.33USD	ml
Hydromorphone-ns 5.5 mg/55 ml	0.33USD	ml
Dilaudid 2 mg Tablet	0.23USD	tablet
Pms-Hydromorphone 4 mg Tablet	0.23USD	tablet
Dilaudid 1 mg Tablet	0.16USD	tablet
Pms-Hydromorphone 2 mg Tablet	0.15USD	tablet
Pms-Hydromorphone 1 mg Tablet	0.1USD	tablet
Dilaudid 1 mg/ml Liquid	0.09USD	ml
Pms-Hydromorphone 1 mg/ml Liquid	0.07USD	ml

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Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)
US5968551	No	1999-10-19	2011-12-24
US6589960	No	2003-07-08	2020-11-09
US9248229	No	2016-02-02	2034-03-12
US9731082	No	2017-08-15	2032-04-23

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	266.5 °C	PhysProp
logP	0.9	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	4.39 mg/mL	ALOGPS
logP	1.69	ALOGPS
logP	1.62	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	10.11	ChemAxon
pKa (Strongest Basic)	8.59	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	49.77 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	78.26 m³·mol^-1	ChemAxon
Polarizability	30.02 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted ADMET features

Property	Value	Probability
Human Intestinal Absorption	+	1.0
Blood Brain Barrier	+	0.9931
Caco-2 permeable	+	0.8647
P-glycoprotein substrate	Substrate	0.8174
P-glycoprotein inhibitor I	Non-inhibitor	0.8497
P-glycoprotein inhibitor II	Non-inhibitor	0.9641
Renal organic cation transporter	Inhibitor	0.6374
CYP450 2C9 substrate	Non-substrate	0.7925
CYP450 2D6 substrate	Substrate	0.8618
CYP450 3A4 substrate	Substrate	0.7571
CYP450 1A2 substrate	Non-inhibitor	0.6918
CYP450 2C9 inhibitor	Non-inhibitor	0.9539
CYP450 2D6 inhibitor	Non-inhibitor	0.5197
CYP450 2C19 inhibitor	Non-inhibitor	0.8088
CYP450 3A4 inhibitor	Non-inhibitor	0.8177
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.9413
Ames test	Non AMES toxic	0.7214
Carcinogenicity	Non-carcinogens	0.9554
Biodegradation	Not ready biodegradable	0.9815
Rat acute toxicity	2.9191 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.8906
hERG inhibition (predictor II)	Non-inhibitor	0.8992

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	Not Available
Mass Spectrum (Electron Ionization)	MS	splash10-002r-6960000000-9f3d9b17d56e032d76c5
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	Not 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

Property	Measurement	pH	Temperature (°C)	References
EC 50 (nM)	2.6	N/A	N/A	19282177
Ki (nM)	0.28	N/A	N/A	19282177

Details1. Mu-type opioid receptor

Kind: Protein
Organism: Humans
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

Quigley C: Hydromorphone for acute and chronic pain. Cochrane Database Syst Rev. 2002;(1):CD003447. [PubMed:11869661]
Inturrisi CE: Clinical pharmacology of opioids for pain. Clin J Pain. 2002 Jul-Aug;18(4 Suppl):S3-13. [PubMed:12479250]
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]
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]

Details2. Delta-type opioid receptor

Kind: Protein
Organism: Humans
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

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]
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]
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]
Guay DR: Use of oral oxymorphone in the elderly. Consult Pharm. 2007 May;22(5):417-30. [PubMed:17658959]
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]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]

Property	Measurement	pH	Temperature (°C)	References
EC 50 (nM)	11	N/A	N/A	19282177
Ki (nM)	2.8	N/A	N/A	19282177

Details3. Kappa-type opioid receptor

Kind: Protein
Organism: Humans
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

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]
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]
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

Details1. Cytochrome P450 3A4

Kind: Protein
Organism: Humans
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

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]
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]

Details2. Cytochrome P450 2C9

Kind: Protein
Organism: Humans
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

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]

Details3. Prostaglandin G/H synthase 1

Kind: Protein
Organism: Humans
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

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]

Details4. UDP-glucuronosyltransferase 1-9

Kind: Protein
Organism: Humans
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

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 February 22, 2019 22:55

Hydromorphone

Identification

Structure for Hydromorphone (DB00327)

Pharmacology

Interactions

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra

Taxonomy

Targets

References

References

References

Enzymes

References

References

References

References