Hydromorphone
Identification
- Name
- Hydromorphone
- Accession Number
- DB00327 (APRD01021)
- Type
- Small Molecule
- Groups
- Approved, Illicit
- Description
Hydromorphone is a pure opioid,[1] a semi-synthetic hydrogenated ketone derivative of morphine that has been available clinically since 1920. Structurally, hydromorphone derived from morphine in the modification of the hydroxyl group in the carbon 6 to a carbonyl and the absence of a double bond between the carbon 7 and 8. Due to these modifications, it presents a very high potency and comparable side effect profile to the parent compound.[2] Even though hydromorphone does not present a 6-hydroxyl group, it is categorized under the family of phenanthrenes and it is considered a chemical under the schedule II (medical purposes with high addiction potential).[3]
The first reported approved product containing hydromorphone in the form of hydromorphone hydrochloride was developed by Fresenius Kabi USA and FDA approved in 1984.[9]
- Structure
Structure for Hydromorphone (DB00327)
- 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
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 Unlock Additional DataDilaudid Injection, solution 4 mg/1mL Intramuscular; Intravenous; Subcutaneous Physicians Total Care, Inc. 2004-08-13 2011-06-30 US 
Dilaudid Injection, solution 4 mg/1mL Intramuscular; Intravenous; Subcutaneous Fresenius Kabi USA, LLC 2016-12-16 2016-12-31 US Dilaudid Tablet 8 mg Oral Purdue Pharma 1989-12-31 Not applicable Canada 
Dilaudid Injection, solution 1 mg/1mL Intramuscular; Intravenous; Subcutaneous Purdue Pharma LP 1926-01-01 2017-02-01 US Dilaudid Injection, solution 2 mg/1mL Intramuscular; Intravenous; Subcutaneous Purdue Pharma LP 1926-01-01 Not applicable US Dilaudid Injection, solution 4 mg/1mL Intramuscular; Intravenous; Subcutaneous Purdue Pharma LP 1926-01-01 Not applicable US Dilaudid Injection, solution 1 mg/1mL Intramuscular; Intravenous; Subcutaneous Fresenius Kabi USA, LLC 2016-12-16 Not applicable US Dilaudid Injection, solution 2 mg/1mL Intramuscular; Intravenous; Subcutaneous Fresenius Kabi USA, LLC 2016-12-16 Not applicable US Dilaudid Tablet 4 mg/1 Oral Cardinal Health 1926-01-01 Not applicable US Dilaudid Liquid 1 mg Oral Purdue Pharma 1989-12-31 Not applicable Canada Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
- Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Unlock Additional DataApo-hydromorphone Tablet 1 mg Oral Apotex Corporation 2012-12-18 Not applicable Canada Apo-hydromorphone Tablet 2 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 8 mg Oral Apotex Corporation 2012-12-18 Not applicable Canada Bar-hydromorphone HCl Capsule, extended release 3 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 6 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 12 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 Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
- Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End 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 (0.2 mg/1mL) Injection, solution Intravenous Cantrell Drug Company 2010-08-23 2017-12-06 US Hydromorphone HCl Hydromorphone hydrochloride (0.5 mg/1mL) Injection, solution Intravenous Cantrell Drug Company 2014-08-13 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 (3 mg/1) Suppository Rectal Paddock Laboratories, LLC 1996-01-31 Not applicable US Hydromorphone Hydrochloride Hydromorphone hydrochloride (2 mg/1mL) Injection Intramuscular; Intravenous; Subcutaneous West-Ward Pharmaceuticals Corp. 1972-01-01 Not applicable US Hydromorphone Hydrochloride Hydromorphone hydrochloride (2 mg/1mL) Injection Intramuscular; Intravenous; Subcutaneous West-Ward Pharmaceuticals Corp. 1972-01-01 Not applicable US - Categories
- Alkaloids
- Analgesics
- Central Nervous System Agents
- Central Nervous System Depressants
- Cytochrome P-450 CYP2C9 Substrates
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 CYP3A4 Substrates (strength unknown)
- Drugs that are Mainly Renally Excreted
- 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
- UGT1A3 substrates
- UGT2B7 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
Hydromorphone is indicated for the management of moderate to severe acute pain and severe chronic pain. Due to its addictive potential and overdose risk, hydromorphone is only prescribed when other first-line treatments have failed.[1]
The WHO has proposed a three-step ladder for the management of pain in which it is suggested to start with a non-opioid medication followed by addition of weak opioids to the non-opioid treatment for moderate pain and finishing in the use of strong opioids such as hydromorphone along with the existing regimen for cases of severe pain.[2]
Off-label, hydromorphone can be administered for the suppression of refractory cough.[1]
- Associated Conditions
- Pharmacodynamics
In clinical trials, hydromorphone has been shown to be suitable for pain relief in patients that do not tolerate the side effects of morphine or that suffer from renal failure or asthma. It has been shown to be 5-7 times more potent than morphine with a shorter duration of analgesia.[2]
Some of the observed effects of the consumption of hydromorphone for acute pain are complete and longlasting pain relief when compared to other pain relief agents such as meperidine, morphine, diamorphine, bupivacaine, indomethacin, and fentanyl. On the same trials, hydromorphone was shown to produce respiratory depression, lower cognitive function, miosis, mydriasis, constipation, hypotension, and vertigo but to present a reduced incidence of pruritus (which indicates a lower release of histamine) and nausea.[7]
The respiratory depression is known to be caused by the effect on the brain stem respiratory centers as well as to a reduction in the responsiveness of this brain stems to increase carbon dioxide tension.[10]
- Mechanism of action
Hydromorphone is an opioid agonist that can bind to different types of opioid receptors. Its analgesic effect is suggested to be related to the effect on the mu-opioid receptors. It has been reported to also have a minor affinity for the delta and kappa receptor.[3, 6] On the other hand, it is known to act at the level of the medulla which allows it to depress the respiratory drive and suppress cough.[1]
The onset of action of the immediate release form of hydromorphone is achieved in 15-20 minutes and having a lasting effect for 3-4 hours while the extended-release form onset of action is of 6 hours lasting for about 13 hours.[1]
Target Actions Organism AMu-type opioid receptor agonistHumans ADelta-type opioid receptor partial agonistHumans AKappa-type opioid receptor agonistHumans - Absorption
The immediate release version of hydromorphone reaches its peak concentration after 30-60 minutes while the extended-release version reaches the peak concentration after 9 hours.[1] When administered orally, hydromorphone is absorbed mainly in the upper small intestine with a bioavailability of 60% due to intensive first-pass metabolism. In the controlled-release version of hydromorphone, the absorption follows a biphasic pharmacokinetic profile. However, even though there are clear distinctions in the absorption pathway of hydromorphone, the AUC of both versions is reported to be of 34 ng.h/ml which indicates an equivalence.[2]
The parenteral administration of hydromorphone, which is the most common pathway, presents an almost immediate absorption as observed by the presence of peak plasma concentration almost immediately. This peak plasma concentration declines rapidly due to fast redistribution into liver, spleen, kidney and skeletal muscle. In the parenteral route, the pharmacokinetic profile is log-linear and dose-dependent and to present a higher bioavailability of 78%.[2]
Other administration routes such as rectal, nasal, intraspinal and transdermal present lower bioavailability and changes in their pharmacokinetic profile.[2]
- Volume of distribution
The volume of distribution of hydromorphone is reported to be of 4 L/kg.[1]
- Protein binding
The protein-bound form of hydromorphone corresponds to about 8-19% of the administered dose.[1]
- Metabolism
The metabolism of hydromorphone is mainly hepatic and it is represented by the generation of hydromorphone-3-glucuronide through glucuronidation reactions.[1] This primary metabolic pathway is done by the activity of the UDP-glucuronosyltransferase-2B7.[4] The first-pass hepatic metabolism is so large that it represents 62% of the initial administered dose.[3]
On the other hand, hydromorphone is also characterized by the presence of minor metabolic pathways such as the CYP3A4- and CYP2C9-driven generation of norhydromorphone.[5]
- Route of elimination
The main elimination route of hydromorphone is through the urine in the form of the main metabolite hydromorphone-3-glucuronide. The elimination of the parent compound represents 7% of the urine elimination and 1% of the fecal elimination.[1]
- Half life
The half-life of hydromorphone immediate-release is of 2-3 hour while the extended release can range from 8-15 hours.[1]
- Clearance
The mean plasma clearance of methadone is reported to be of 105.7 ml/min.[8] The systemic clearance is reported to be of 1.96 L/min.[10]
- Toxicity
The reported LD50 of hydromorphone in the mouse was of 104 mg/kg when given intravenously and 84 mg/kg when given orally.[11] The reports of overdose with hydromorphone are characterized by respiratory depression, somnolence, skeletal muscle flaccidity, cold and clammy skin, constricted pupils, myosis, mydriasis, bradycardia, hypotension, apnea, circulatory collapse, cardiac arrest, and even death.[Label]
The management of an overdose might require assisted ventilation, supportive measures, as well as cardiac massage and defibrillation. It can be recommended the use of naloxone solely in the cases of respiratory depression. The use of opioid antagonist should be restricted to patients that present respiratory depression as they can produce acute abstinence symptoms.[Label]
Hydromorphone was not shown to be mutagenic nor clastogenic and long-term studies of carcinogenicity studies have not been performed. On the other hand, reduced implantation sites and viable fetuses were noted at a 2X normal concentration.[Label]
- Affected organisms
- Humans and other mammals
- Pathways
Pathway Category Hydromorphone Action Pathway Drug action - Pharmacogenomic Effects/ADRs
- Not Available
Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.
Learn moreStructured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.
Learn moreStructured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.
Learn moreInteractions
- Drug Interactions
Drug Interaction Unlock Additional Data(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 2,5-Dimethoxy-4-ethylamphetamine may increase the analgesic activities of Hydromorphone. 2,5-Dimethoxy-4-ethylthioamphetamine 2,5-Dimethoxy-4-ethylthioamphetamine may increase the analgesic activities of Hydromorphone. 3,5-diiodothyropropionic acid The metabolism of 3,5-diiodothyropropionic acid can be decreased when combined with Hydromorphone. 4-Bromo-2,5-dimethoxyamphetamine 4-Bromo-2,5-dimethoxyamphetamine may increase the analgesic activities of Hydromorphone. 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. 6-Deoxyerythronolide B The metabolism of Hydromorphone can be decreased when combined with 6-Deoxyerythronolide B. Additional Data Available- Extended DescriptionExtended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - Severity
- Evidence Level
- ActionEvidence Level
An effect category for each drug interaction. Know how this interaction affects the subject drug.
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- Food Interactions
- Take without regard to meals. Avoid alcohol.
References
- Synthesis Reference
- US5571685
- General References
- Abi-Aad KR, Derian A: Hydromorphone . [PubMed:29261877]
- Kumar MG, Lin S: Hydromorphone in the management of cancer-related pain: an update on routes of administration and dosage forms. J Pharm Pharm Sci. 2007;10(4):504-18. [PubMed:18261371]
- Trescot AM, Datta S, Lee M, Hansen H: Opioid pharmacology. Pain Physician. 2008 Mar;11(2 Suppl):S133-53. [PubMed:18443637]
- Overholser BR, Foster DR: Opioid pharmacokinetic drug-drug interactions. Am J Manag Care. 2011 Sep;17 Suppl 11:S276-87. [PubMed:21999760]
- 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]
- Drewes AM, Jensen RD, Nielsen LM, Droney J, Christrup LL, Arendt-Nielsen L, Riley J, Dahan A: Differences between opioids: pharmacological, experimental, clinical and economical perspectives. Br J Clin Pharmacol. 2013 Jan;75(1):60-78. doi: 10.1111/j.1365-2125.2012.04317.x. [PubMed:22554450]
- Murray A, Hagen NA: Hydromorphone. J Pain Symptom Manage. 2005 May;29(5 Suppl):S57-66. doi: 10.1016/j.jpainsymman.2005.01.007. [PubMed:15907647]
- Perlman R, Giladi H, Brecht K, Ware MA, Hebert TE, Joseph L, Shir Y: Intradialytic clearance of opioids: methadone versus hydromorphone. Pain. 2013 Dec;154(12):2794-800. doi: 10.1016/j.pain.2013.08.015. Epub 2013 Aug 20. [PubMed:23973378]
- FDA approvals [Link]
- Clinical trials [Link]
- BAR-hydromorphone monograph [File]
- 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
- N02AA53 — Hydromorphone and naloxoneN02AA03 — HydromorphoneN02AG04 — Hydromorphone and antispasmodics
- AHFS Codes
- 28:08.08 — Opiate Agonists
- FDA label
- Download (600 KB)
- MSDS
- Download (73.3 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 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 32 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) Unlock Additional DataUS5968551 No 1999-10-19 2011-12-24 US US6589960 No 2003-07-08 2020-11-09 US US9248229 No 2016-02-02 2034-03-12 US US9731082 No 2017-08-15 2032-04-23 US Additional Data Available- Filed On
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) Decomposes at 305ºC 'MSDS' boiling point (°C) Decomposes at 305ºC 'MSDS' water solubility Highly soluble Trescot A. et al. (2008). Pain Physician. logP 1.06 Agilent. SAMHSA-Compilant Analysis of Opiates. pKa 8.2 Agilent. SAMHSA-Compilant Analysis of Opiates. - 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
- 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]
- 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]
- 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
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- 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
- 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]
- 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]
- Baldacci A, Thormann W: Capillary electrophoresis contributions to the hydromorphone metabolism in man. Electrophoresis. 2006 Jun;27(12):2444-57. doi: 10.1002/elps.200500867. [PubMed:16718649]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- 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
- Humans
- Pharmacological action
- No
- 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. Isoform 2 lacks transferase activity but acts as a negative reg...
- Gene Name
- UGT1A3
- Uniprot ID
- P35503
- Uniprot Name
- UDP-glucuronosyltransferase 1-3
- Molecular Weight
- 60337.835 Da
References
- Gudin J: Opioid therapies and cytochrome p450 interactions. J Pain Symptom Manage. 2012 Dec;44(6 Suppl):S4-14. doi: 10.1016/j.jpainsymman.2012.08.013. [PubMed:23218233]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Glucuronosyltransferase activity
- Specific Function
- UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.Its unique specificity for 3,4-catechol estrogens and estriol su...
- Gene Name
- UGT2B7
- Uniprot ID
- P16662
- Uniprot Name
- UDP-glucuronosyltransferase 2B7
- Molecular Weight
- 60694.12 Da
References
- Overholser BR, Foster DR: Opioid pharmacokinetic drug-drug interactions. Am J Manag Care. 2011 Sep;17 Suppl 11:S276-87. [PubMed:21999760]
- Gudin J: Opioid therapies and cytochrome p450 interactions. J Pain Symptom Manage. 2012 Dec;44(6 Suppl):S4-14. doi: 10.1016/j.jpainsymman.2012.08.013. [PubMed:23218233]
Carriers
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Binder
- General Function
- Toxic substance binding
- Specific Function
- Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
- Gene Name
- ALB
- Uniprot ID
- P02768
- Uniprot Name
- Serum albumin
- Molecular Weight
- 69365.94 Da
References
- Abi-Aad KR, Derian A: Hydromorphone . [PubMed:29261877]
Drug created on June 13, 2005 07:24 / Updated on April 24, 2019 15:24