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IdentificationPharmacologyInteractionsReferencesTrialsEconomicsPropertiesSpectraTaxonomyHydromorphone
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. [PubChem]
- Structure
Structure for Hydromorphone (DB00327)
- Synonyms
- (-)-(5R)-4,5-Epoxy-3-hydroxy-9alpha-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
Ingredient UNII CAS InChI Key Hydromorphone Hydrochloride L960UP2KRW 71-68-1 XHILEZUETWRSHC-NRGUFEMZSA-N Hydromorphone sulfate 75Y990NH3Z 25333-57-7 JBBINZRUTLUBFR-NRGUFEMZSA-N - Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Dilaudid Tablet 4 mg/1 Oral Cardinal Health 1926-01-01 Not applicable US 
Dilaudid Tablet 8 mg/1 Oral Purdue Pharma LP 1956-01-01 Not applicable US Dilaudid Injection, solution 1 mg/1mL Intramuscular; Intravenous; Subcutaneous Fresenius Kabi 2016-12-16 Not applicable US Dilaudid Tablet 8 mg/1 Oral Rhodes Pharmaceuticals L.P. 2017-05-15 Not applicable US Dilaudid Tablet 1 mg Oral Purdue Pharma 1986-12-31 Not applicable Canada 
Dilaudid Tablet 8 mg/1 Oral Abbvie 1992-12-07 2008-12-31 US Dilaudid Tablet 2 mg/1 Oral Physicians Total Care, Inc. 2003-11-11 2011-06-30 US Dilaudid Liquid 5 mg/5mL Oral Purdue Pharma LP 1956-01-01 Not applicable US Dilaudid Tablet 4 mg Oral Purdue Pharma 1984-12-31 Not applicable Canada Dilaudid Injection, solution 4 mg/1mL Intramuscular; Intravenous; Subcutaneous Physicians Total Care, Inc. 2004-08-13 2011-06-30 US - 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 Canada Apo-hydromorphone Tablet 1 mg Oral Apotex Corporation 2012-12-18 Not applicable Canada Apo-hydromorphone Tablet 4 mg Oral Apotex Corporation 2012-12-18 Not applicable Canada Apo-hydromorphone Tablet 2 mg Oral Apotex Corporation 2012-12-18 Not applicable Canada Bar-hydromorphone HCl Capsule, extended release 12 mg Oral Bard Pharmaceuticals (1990) Inc Not applicable Not applicable Canada Bar-hydromorphone HCl Capsule, extended release 4.5 mg Oral Bard Pharmaceuticals (1990) Inc Not applicable Not applicable Canada Bar-hydromorphone HCl Capsule, extended release 24 mg Oral Bard Pharmaceuticals (1990) Inc Not applicable Not applicable Canada Bar-hydromorphone HCl Capsule, extended release 9 mg Oral Bard Pharmaceuticals (1990) Inc Not applicable Not applicable Canada Bar-hydromorphone HCl Capsule, extended release 18 mg Oral Bard Pharmaceuticals (1990) Inc Not applicable Not applicable Canada Bar-hydromorphone HCl Capsule, extended release 6 mg Oral Bard Pharmaceuticals (1990) Inc Not applicable Not applicable Canada - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Hydromorphone HCl Hydromorphone Hydrochloride (0.5 mg/1mL) Injection, solution Intravenous Cantrell Drug Company 2014-08-13 Not applicable US Hydromorphone HCl Hydromorphone Hydrochloride (0.2 mg/1mL) Injection, solution Intravenous Cantrell Drug Company 2010-08-23 2017-12-06 US Hydromorphone HCl Hydromorphone Hydrochloride (10 mg/1mL) Injection, solution Intravenous Cantrell Drug Company 2014-08-13 Not applicable US Hydromorphone HCl Hydromorphone Hydrochloride (0.1 mg/1mL) Injection, solution Intravenous Cantrell Drug Company 2014-08-21 Not applicable US Hydromorphone HCl Hydromorphone Hydrochloride (1 mg/1mL) Injection, solution Intravenous Cantrell Drug Company 2012-08-30 2017-12-06 US Hydromorphone HCl Hydromorphone Hydrochloride (0.4 mg/1mL) Injection, solution Intravenous Cantrell Drug Company 2014-08-13 Not applicable US Hydromorphone HCl Hydromorphone Hydrochloride (2 mg/1mL) Injection, solution Intravenous Cantrell Drug Company 2014-08-13 Not applicable US Hydromorphone Hydrochloride Hydromorphone Hydrochloride (2 mg/1mL) Injection Intramuscular; Intravenous; Subcutaneous West Ward Pharmaceutical 1972-01-01 Not applicable US Hydromorphone Hydrochloride Hydromorphone Hydrochloride (2 mg/1mL) Injection Intramuscular; Intravenous; Subcutaneous West Ward Pharmaceutical 1972-01-01 Not applicable US Hydromorphone Hydrochloride Hydromorphone Hydrochloride (3 mg/1) Suppository Rectal Paddock Laboratories, Inc. 1996-01-31 Not applicable US - International/Other Brands
- Palladone
- Categories
- Alkaloids
- Analgesics
- Central Nervous System Agents
- Central Nervous System Depressants
- Cytochrome P-450 CYP2C9 Substrates
- Cytochrome P-450 CYP2D6 Substrates
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Substrates
- Morphinans
- Morphine Derivatives
- Narcotics
- Natural Opium Alkaloids
- Nervous System
- Opiate Agonists
- Opiate Alkaloids
- Opioid Agonist
- Opioids
- Peripheral Nervous System Agents
- Phenanthrenes
- Semi-synthetic Opioids
- Sensory System Agents
- Serotonergic Drugs Shown to Increase Risk of Serotonin Syndrome
- UGT1A9 Substrates
- 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 agonistHuman ADelta-type opioid receptor partial agonistHuman AKappa-type opioid receptor agonistHuman - 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.
- Hydromorphone Dihydromorphine
- Hydromorphone Dihydroisomorphine
- Hydromorphone Norhydromorphone
- Hydromorphone Hydromorphone 3-beta-O-glucuronide
- Hydromorphone Dihydroisomorphine-6-glucuronide
- Hydromorphone Hydromorphone-3-glucoside
- Hydromorphone Hydromorphone-3-glucuronide
- Hydromorphone Hydromorphone-3-sulphate
- 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 — 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
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 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 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 16 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 1 mg/1mL Injection, solution Intramuscular; Intravenous; Subcutaneous 10 mg/1mL Injection, solution Intramuscular; Intravenous; Subcutaneous 2 mg/1mL Solution Oral 1 mg/1mL Solution Oral 5 mg/5mL Suppository Rectal 3 mg/1 Tablet Oral 2 mg/1 Tablet Oral 4 mg/1 Tablet Oral 8 mg/1 Tablet, extended release Oral 12 mg/1 Tablet, extended release Oral 32 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 DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) US5968551 No 1994-12-24 2011-12-24 US US6589960 No 2000-11-09 2020-11-09 US US9248229 No 2014-03-12 2034-03-12 US US9731082 No 2012-04-23 2032-04-23 US
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
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
- 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
- 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]
- 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
- 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]
- 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
- 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
- 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
- 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]
- 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
- 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
- Steroid hydroxylase activity
- Specific Function
- Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
- Gene Name
- CYP2D6
- Uniprot ID
- P10635
- Uniprot Name
- Cytochrome P450 2D6
- Molecular Weight
- 55768.94 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]
- 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
- 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
- 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 November 14, 2018 12:40