You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
Identification
NameHydromorphone
Accession NumberDB00327  (APRD01021)
TypeSmall Molecule
GroupsApproved, 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
Thumb
Synonyms
SynonymLanguageCode
(-)-(5R)-4,5-Epoxy-3-hydroxy-9alpha-methylmorphinan-6-oneNot AvailableNot Available
4,5-Epoxy-3-hydroxy-17-methylmorphinan-6-oneNot AvailableNot Available
4,5alpha-Epoxy-3-hydroxy-17-methyl-6-morphinanoneNot AvailableNot Available
6-Deoxy-7,8-dihydro-6-oxomorphineNot AvailableNot Available
7,8-DihydromorphinoneNot AvailableNot Available
DihydromorfinonCzechNot Available
DihydromorphinoneNot AvailableNot Available
DimorphoneNot AvailableNot Available
HidromorfonaSpanishINN
HydromorfonaSpanishNot Available
HydromorphoneNot AvailableNot Available
HydromorphonumLatinINN
IdromorfoneItalianNot Available
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Hydromorphone Hydrochlorideinjection, solution1 mg/mLintramuscular; intravenous; subcutaneousHospira, Inc.2011-12-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Hydromorphone Hydrochlorideinjection, solution4 mg/mLintramuscular; intravenous; subcutaneousHospira, Inc.2011-12-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Hydromorphone Hydrochlorideinjection, solution2 mg/mLintramuscular; intravenous; subcutaneousHospira, Inc.2011-12-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Hydromorphone Hydrochlorideinjection, solution4 mg/mLintramuscular; intravenous; subcutaneousHospira, Inc.2011-12-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Hydromorphone Hydrochlorideinjection, solution1 mg/mLintramuscular; intravenous; subcutaneousHospira, Inc.2011-12-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Hydromorphone Hydrochlorideinjection, solution2 mg/mLintramuscular; intravenous; subcutaneousHospira, Inc.2011-12-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Hydromorphone Hydrochlorideinjection, solution2 mg/mLintramuscular; intravenous; subcutaneousHospira, Inc.2011-12-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Hydromorphone Hydrochloridetablet8 mgoralSTAT Rx USA LLC2009-11-23Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Exalgotablet, extended release8 mgoralSTAT Rx USA LLC2011-03-14Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Exalgotablet, extended release8 mgoralMallinckrodt, Inc2011-03-14Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Exalgotablet, extended release12 mgoralMallinckrodt, Inc2011-03-14Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Exalgotablet, extended release16 mgoralMallinckrodt, Inc2011-03-14Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Exalgotablet, extended release32 mgoralMallinckrodt, Inc2012-08-24Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Dilaudidtablet4 mgoralLake Erie Medical DBA Quality Care Products LLC1956-01-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Dilaudidtablet2 mgoralLake Erie Medical & Surgical Supply DBA Quality Care Products LLC2011-12-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Exalgotablet, extended release12 mgoralLake Erie Medical DBA Quality Care Products LLC2011-03-14Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Exalgotablet, extended release16 mgoralLake Erie Medical DBA Quality Care Products LLC2011-03-14Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Exalgotablet, extended release8 mgoralLake Erie Medical DBA Quality Care Products LLC2011-03-14Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Hydromorphone Hydrochloridetablet2 mgoralRhodes Pharmaceuticals L.P.2009-11-23Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Hydromorphone Hydrochloridetablet4 mgoralRhodes Pharmaceuticals L.P.2009-11-23Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Hydromorphone Hydrochloridetablet8 mgoralRhodes Pharmaceuticals L.P.2009-11-23Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Hydromorphone Hydrochloridesolution5 mg/5mLoralRhodes Pharmaceuticals L.P.2012-07-20Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Exalgotablet, extended release8 mgoralPhysicians Total Care, Inc.2012-12-31Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Exalgotablet, extended release16 mgoralPhysicians Total Care, Inc.2012-12-31Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Dilaudidtablet4 mgoralCardinal Health1926-01-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Dilaudidinjection, solution1 mg/mLintramuscular; intravenous; subcutaneousPurdue Pharma LP1926-01-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Dilaudidinjection, solution2 mg/mLintramuscular; intravenous; subcutaneousPurdue Pharma LP1926-01-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Dilaudidinjection, solution4 mg/mLintramuscular; intravenous; subcutaneousPurdue Pharma LP1926-01-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Dilaudidliquid5 mg/5mLoralPurdue Pharma LP1956-01-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Dilaudidtablet2 mgoralPurdue Pharma LP1956-01-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Dilaudidtablet4 mgoralPurdue Pharma LP1956-01-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Dilaudidtablet8 mgoralPurdue Pharma LP1956-01-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Hydromorphone Hydrochloridetablet4 mgoralbryant ranch prepack2009-11-23Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Hydromorphone Hydrochloridetablet2 mgoralbryant ranch prepack2009-11-23Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Hydromorphone Hydrochloridetablet4 mgoralRoxane Laboratories, Inc2009-07-29Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Hydromorphone Hydrochloridetablet8 mgoralRoxane Laboratories, Inc2009-07-29Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Hydromorphone Hydrochloridesolution1 mg/mLoralRoxane Laboratories, Inc2012-03-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Hydromorphone Hydrochloridetablet2 mgoralMallinckrodt, Inc.2009-05-14Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Hydromorphone Hydrochloridetablet4 mgoralMallinckrodt, Inc.2009-05-14Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Hydromorphone Hydrochloridetablet8 mgoralMallinckrodt, Inc.2009-05-14Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Hydromorphone Hydrochlorideinjection, solution10 mg/mLintramuscular; intravenous; subcutaneousHospira, Inc.2010-08-19Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Hydromorphone Hydrochloridetablet2 mgoralLannett Company, Inc.2009-12-09Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Hydromorphone Hydrochloridetablet4 mgoralLannett Company, Inc.2009-12-09Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Hydromorphone Hydrochloridetablet8 mgoralLannett Company, Inc.2009-12-09Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Hydromorphone Hydrochloridetablet, extended release8 mgoralWatson Laboratories, Inc.2014-05-21Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Hydromorphone Hydrochloridetablet, extended release16 mgoralWatson Laboratories, Inc.2014-05-21Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Hydromorphone Hydrochloridetablet, extended release12 mgoralWatson Laboratories, Inc.2014-05-21Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Hydromorphone Hydrochlorideinjection, solution10 mg/mLintramuscular; intravenous; subcutaneousTeva Parenteral Medicines, Inc.2011-01-18Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Hydromorphone Hydrochlorideinjection, solution10 mg/mLintramuscular; intravenous; subcutaneousTeva Parenteral Medicines, Inc.2011-01-18Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Hydromorphone Hydrochlorideinjection, solution10 mg/mLintramuscular; intravenous; subcutaneousTeva Parenteral Medicines, Inc.2011-01-18Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Hydromorphone Hydrochloridetablet2 mgoralSTAT Rx USA LLC2009-05-14Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Hydromorphone Hydrochlorideinjection10 mg/mLparenteralAkorn, Inc.2010-05-15Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Hydromorphone Hydrochloridetablet2 mgoralLake Erie Medical DBA Quality Care Products LLC2009-05-14Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Hydromorphone Hydrochloridetablet8 mgoralLake Erie Medical DBA Quality Care Products LLC2009-12-09Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Hydromorphone Hydrochloridetablet4 mgoralLake Erie Medical DBA Quality Care Products LLC2009-12-09Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Hydromorphone Hydrochloridetablet2 mgoralLake Erie Medical DBA Quality Care Products LLC2009-12-09Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Hydromorphone Hydrochloridetablet4 mgoralSTAT Rx USA LLC2007-09-19Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Hydromorphone Hydrochloridetablet2 mgoralSTAT Rx USA LLC2007-09-19Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Hydromorphone Hydrochloridetablet2 mgoralPd Rx Pharmaceuticals, Inc.2009-12-09Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Hydromorphone Hydrochloridetablet4 mgoralLake Erie Medical & Surgical Supply DBA Quality Care Products LLC2011-11-29Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Hydromorphone Hydrochloridetablet4 mgoralLake Erie Medical & Surgical Supply DBA Quality Care Products LLC2011-11-29Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Hydromorphone Hydrochloridetablet8 mgoralLake Erie Medical DBA Quality Care Products LLC2010-04-26Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Hydromorphone Hydrochloridetablet8 mgoralTAGI Pharma, Inc.2012-03-09Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Hydromorphone Hydrochloridetablet4 mgoralH.J. Harkins Company, Inc.2009-12-09Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Hydromorphone Hydrochloridetablet8 mgoralH.J. Harkins Company, Inc.2009-12-09Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Hydromorphone Hydrochloridetablet2 mgoralH.J. Harkins Company, Inc.2009-12-09Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Hydromorphone Hydrochloridetablet, film coated2 mgoralPhysicians Total Care, Inc.2004-09-20Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Hydromorphone Hydrochloridetablet, film coated8 mgoralPhysicians Total Care, Inc.2002-02-06Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Hydromorphone Hydrochloridetablet, film coated4 mgoralPhysicians Total Care, Inc.2004-01-07Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Hydromorphone Hydrochloridetablet8 mgoralbryant ranch prepack2009-07-29Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Hydromorphone Hydrochloridetablet2 mgoralAmerican Health Packaging2013-07-17Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Hydromorphone Hydrochloridetablet4 mgoralAmerican Health Packaging2013-07-17Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Hydromorphone Hydrochloridetablet8 mgoralAmerican Health Packaging2014-08-14Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Over the Counter ProductsNot Available
International Brands
NameCompany
PalladoneNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Hydromorphone Hydrochloride
71-68-1
Thumb
  • InChI Key: XHILEZUETWRSHC-NRGUFEMZSA-N
  • Monoisotopic Mass: 321.113171218
  • Average Mass: 321.799
DBSALT000444
Categories
CAS number466-99-9
WeightAverage: 285.3377
Monoisotopic: 285.136493479
Chemical FormulaC17H19NO3
InChI KeyWVLOADHCBXTIJK-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
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassMorphinans
Sub ClassNot Available
Direct ParentMorphinans
Alternative Parents
Substituents
  • Morphinan
  • Benzylisoquinoline
  • Phenanthrene
  • Isoquinolone
  • Tetralin
  • Benzofuran
  • Aralkylamine
  • Cyclohexanone
  • Alkyl aryl ether
  • Benzenoid
  • Piperidine
  • Tertiary aliphatic amine
  • Tertiary amine
  • Ketone
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Ether
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Pharmacology
IndicationFor the relief of moderate to severe pain such as that due to surgery, cancer, trauma/injury, or burns.
PharmacodynamicsHydromorphone 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 actionHydromorphone 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.
AbsorptionBetter absorbed orally than morphine
Volume of distributionNot Available
Protein binding20%
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.

SubstrateEnzymesProduct
Hydromorphone
DihydromorphineDetails
Hydromorphone
DihydroisomorphineDetails
Hydromorphone
NorhydromorphoneDetails
Hydromorphone
Hydromorphone 3-beta-O-glucuronideDetails
Hydromorphone
Not Available
Dihydroisomorphine-6-glucuronideDetails
Hydromorphone
Not Available
Hydromorphone-3-glucosideDetails
Hydromorphone
Not Available
Hydromorphone-3-glucuronideDetails
Hydromorphone
Not Available
Hydromorphone-3-sulphateDetails
Dihydromorphine
Dihydromorphine-3-glucuronideDetails
Route of eliminationOnly 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 life2.6 hours (oral); 18.6 hours for sustained release Palladone
Clearance
  • 1.96 L/min
ToxicityHydromorphone 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
PathwayCategorySMPDB ID
Hydromorphone Action PathwayDrug actionSMP00410
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9931
Caco-2 permeable+0.8647
P-glycoprotein substrateSubstrate0.8174
P-glycoprotein inhibitor INon-inhibitor0.8497
P-glycoprotein inhibitor IINon-inhibitor0.9641
Renal organic cation transporterInhibitor0.6374
CYP450 2C9 substrateNon-substrate0.7925
CYP450 2D6 substrateSubstrate0.8618
CYP450 3A4 substrateSubstrate0.7571
CYP450 1A2 substrateNon-inhibitor0.6918
CYP450 2C9 substrateNon-inhibitor0.9539
CYP450 2D6 substrateNon-inhibitor0.5197
CYP450 2C19 substrateNon-inhibitor0.8088
CYP450 3A4 substrateNon-inhibitor0.8177
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9413
Ames testNon AMES toxic0.7214
CarcinogenicityNon-carcinogens0.9554
BiodegradationNot ready biodegradable0.9815
Rat acute toxicity2.9191 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8906
hERG inhibition (predictor II)Non-inhibitor0.8992
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
Dosage forms
FormRouteStrength
Injectionparenteral10 mg/mL
Injection, solutionintramuscular; intravenous; subcutaneous1 mg/mL
Injection, solutionintramuscular; intravenous; subcutaneous10 mg/mL
Injection, solutionintramuscular; intravenous; subcutaneous2 mg/mL
Injection, solutionintramuscular; intravenous; subcutaneous4 mg/mL
Liquidoral5 mg/5mL
Solutionoral1 mg/mL
Solutionoral5 mg/5mL
Tabletoral2 mg
Tabletoral4 mg
Tabletoral8 mg
Tablet, extended releaseoral12 mg
Tablet, extended releaseoral16 mg
Tablet, extended releaseoral32 mg
Tablet, extended releaseoral8 mg
Tablet, film coatedoral2 mg
Tablet, film coatedoral4 mg
Tablet, film coatedoral8 mg
Prices
Unit descriptionCostUnit
Hydromorphone hcl powder166.25USD g
Dilaudid-hp 250 mg vial114.8USD vial
Dilaudid Sterile Powder 250 mg/vial78.99USD vial
HYDROmorphone HCl 6 3 mg Suppository Box54.92USD box
Hydromorphone Hp 50 50 mg/ml13.78USD ml
Dilaudid-Xp 50 mg/ml11.82USD ml
Hydromorphone 3 mg suppository11.11USD suppository
Dilaudid-Hp-Plus 20 mg/ml5.08USD ml
Hydromorphone Hp 20 20 mg/ml4.72USD ml
Hydromorph Contin 30 mg Controlled-Release Capsule4.21USD capsule
Hydromorph Contin 24 mg Controlled-Release Capsule3.52USD capsule
Dilaudid-Hp 10 mg/ml3.14USD ml
Hydromorphone Hp 10 mg/ml2.92USD ml
Hydromorph Contin 18 mg Controlled-Release Capsule2.75USD capsule
Hydromorphone 10 mg/ml ampul2.58USD ml
Pms-Hydromorphone 3 mg Suppository2.42USD suppository
Dilaudid 4 mg/ml ampul2.2USD ml
Dilaudid 8 mg tablet2.19USD tablet
HYDROmorphone HCl 4 mg/ml Solution 1ml Cartridge2.07USD cartridge
Hydromorph Contin 12 mg Controlled-Release Capsule1.91USD capsule
Dilaudid 2 mg/ml ampul1.81USD ml
Dilaudid 1 mg/ml ampul1.64USD ml
Hydromorphone hcl 8 mg tablet1.4USD tablet
Dilaudid 4 mg tablet1.36USD tablet
Hydromorphone 8 mg tablet1.32USD tablet
Dilaudid 2 mg/ml1.28USD ml
Hydromorphone 2 mg/ml1.19USD ml
Hydromorph Contin 6 mg Controlled-Release Capsule1.1USD capsule
Hydromorphone-ns 0.4 mg/ml1.08USD ml
Hydromorphone-ns 0.3 mg/ ml1.05USD ml
Hydromorphone 2 mg/ml vial1.02USD ml
Hydromorphone-ns 25 mg/25 ml1.01USD ml
Dilaudid 2 mg tablet1.0USD tablet
Hydromorphone-ns 2.5 mg/25 ml0.96USD ml
HYDROmorphone HCl 4 mg tablet0.8USD tablet
HYDROmorphone HCl 2 mg tablet0.77USD tablet
Hydromorph Contin 3 mg Controlled-Release Capsule0.73USD capsule
Hydromorphone 4 mg tablet0.72USD tablet
Dilaudid 8 mg Tablet0.55USD tablet
Hydromorphone-ns 0.2 mg/ml0.49USD ml
Hydromorphone 2 mg tablet0.37USD tablet
Pms-Hydromorphone 8 mg Tablet0.37USD tablet
Dilaudid 4 mg Tablet0.35USD tablet
Dilaudid-5 1 mg/ml liquid0.33USD ml
Hydromorphone-ns 5.5 mg/55 ml0.33USD ml
Dilaudid 2 mg Tablet0.23USD tablet
Pms-Hydromorphone 4 mg Tablet0.23USD tablet
Dilaudid 1 mg Tablet0.16USD tablet
Pms-Hydromorphone 2 mg Tablet0.15USD tablet
Pms-Hydromorphone 1 mg Tablet0.1USD tablet
Dilaudid 1 mg/ml Liquid0.09USD ml
Pms-Hydromorphone 1 mg/ml Liquid0.07USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
CountryPatent NumberApprovedExpires (estimated)
United States59685511994-12-242011-12-24
United States65899602000-11-092020-11-09
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point266.5 °CPhysProp
logP0.9Not Available
Predicted Properties
PropertyValueSource
Water Solubility4.39 mg/mLALOGPS
logP1.69ALOGPS
logP1.62ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)10.11ChemAxon
pKa (Strongest Basic)8.59ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area49.77 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity78.26 m3·mol-1ChemAxon
Polarizability30.02 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraMS
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 Reference
  1. Coda BA, Rudy AC, Archer SM, Wermeling DP: Pharmacokinetics and bioavailability of single-dose intranasal hydromorphone hydrochloride in healthy volunteers. Anesth Analg. 2003 Jul;97(1):117-23, table of contents. Pubmed
  2. Vallner JJ, Stewart JT, Kotzan JA, Kirsten EB, Honigberg IL: Pharmacokinetics and bioavailability of hydromorphone following intravenous and oral administration to human subjects. J Clin Pharmacol. 1981 Apr;21(4):152-6. Pubmed
External Links
ATC CodesN02AA03
AHFS Codes
  • 28:08.08
PDB EntriesNot Available
FDA labelDownload (78.9 KB)
MSDSDownload (48.3 KB)
Interactions
Drug Interactions
Drug
AcetazolamideAnalgesics (Opioid) may enhance the adverse/toxic effect of Diuretics.
AlvimopanAnalgesics (Opioid) may enhance the adverse/toxic effect of Alvimopan. This is most notable for patients receiving long-term (i.e., more than 7 days) opiates prior to alvimopan initiation.
AmilorideAnalgesics (Opioid) may enhance the adverse/toxic effect of Diuretics.
Ammonium chlorideMay increase the excretion of Analgesics (Opioid).
AmphetamineMay enhance the analgesic effect of Analgesics (Opioid).
BendroflumethiazideAnalgesics (Opioid) may enhance the adverse/toxic effect of Diuretics.
BumetanideAnalgesics (Opioid) may enhance the adverse/toxic effect of Diuretics.
CathinoneMay enhance the analgesic effect of Analgesics (Opioid).
ChlorothiazideAnalgesics (Opioid) may enhance the adverse/toxic effect of Diuretics.
ChlorthalidoneAnalgesics (Opioid) may enhance the adverse/toxic effect of Diuretics.
CyclothiazideAnalgesics (Opioid) may enhance the adverse/toxic effect of Diuretics.
DesmopressinAnalgesics (Opioid) may enhance the adverse/toxic effect of Desmopressin.
DoxylamineMay enhance the CNS depressant effect of CNS Depressants.
DronabinolMay enhance the CNS depressant effect of CNS Depressants.
DroperidolMay enhance the CNS depressant effect of CNS Depressants.
Ethacrynic acidAnalgesics (Opioid) may enhance the adverse/toxic effect of Diuretics.
EthoxzolamideAnalgesics (Opioid) may enhance the adverse/toxic effect of Diuretics.
FurosemideAnalgesics (Opioid) may enhance the adverse/toxic effect of Diuretics.
HydrochlorothiazideAnalgesics (Opioid) may enhance the adverse/toxic effect of Diuretics.
HydrocodoneCNS Depressants may enhance the CNS depressant effect of Hydrocodone.
HydroflumethiazideAnalgesics (Opioid) may enhance the adverse/toxic effect of Diuretics.
HydroxyzineMay enhance the CNS depressant effect of CNS Depressants.
IndapamideAnalgesics (Opioid) may enhance the adverse/toxic effect of Diuretics.
IsocarboxazidMAO Inhibitors may enhance the adverse/toxic effect of HYDROmorphone.
LinezolidMAO Inhibitors may enhance the adverse/toxic effect of HYDROmorphone.
Magnesium SulfateMay enhance the CNS depressant effect of CNS Depressants.
MethotrimeprazineCNS Depressants may enhance the CNS depressant effect of Methotrimeprazine. Methotrimeprazine may enhance the CNS depressant effect of CNS Depressants.
MetolazoneAnalgesics (Opioid) may enhance the adverse/toxic effect of Diuretics.
MetyrosineCNS Depressants may enhance the sedative effect of Metyrosine.
MirtazapineCNS Depressants may enhance the CNS depressant effect of Mirtazapine.
MoclobemideMAO Inhibitors may enhance the adverse/toxic effect of HYDROmorphone.
NabiloneMay enhance the CNS depressant effect of CNS Depressants.
NaltrexoneMay diminish the therapeutic effect of Analgesics (Opioid).
OrphenadrineCNS Depressants may enhance the CNS depressant effect of Orphenadrine.
PegvisomantAnalgesics (Opioid) may diminish the therapeutic effect of Pegvisomant.
PerampanelMay enhance the CNS depressant effect of CNS Depressants.
PhenelzineMAO Inhibitors may enhance the adverse/toxic effect of HYDROmorphone.
PramipexoleCNS Depressants may enhance the sedative effect of Pramipexole.
ProcarbazineMAO Inhibitors may enhance the adverse/toxic effect of HYDROmorphone.
RasagilineMAO Inhibitors may enhance the adverse/toxic effect of HYDROmorphone.
RopiniroleCNS Depressants may enhance the sedative effect of ROPINIRole.
RotigotineCNS Depressants may enhance the sedative effect of Rotigotine.
RufinamideMay enhance the adverse/toxic effect of CNS Depressants. Specifically, sleepiness and dizziness may be enhanced.
SelegilineMAO Inhibitors may enhance the adverse/toxic effect of HYDROmorphone.
SpironolactoneAnalgesics (Opioid) may enhance the adverse/toxic effect of Diuretics.
SuccinylcholineMay enhance the bradycardic effect of Analgesics (Opioid).
SuvorexantCNS Depressants may enhance the CNS depressant effect of Suvorexant.
TapentadolMay enhance the CNS depressant effect of CNS Depressants.
Tedizolid PhosphateMAO Inhibitors may enhance the adverse/toxic effect of HYDROmorphone.
ThalidomideCNS Depressants may enhance the CNS depressant effect of Thalidomide.
TicrynafenAnalgesics (Opioid) may enhance the adverse/toxic effect of Diuretics.
TorasemideAnalgesics (Opioid) may enhance the adverse/toxic effect of Diuretics.
TranylcypromineMAO Inhibitors may enhance the adverse/toxic effect of HYDROmorphone.
TriamtereneAnalgesics (Opioid) may enhance the adverse/toxic effect of Diuretics.
TrichlormethiazideAnalgesics (Opioid) may enhance the adverse/toxic effect of Diuretics.
ZolpidemCNS Depressants may enhance the CNS depressant effect of Zolpidem.
Food Interactions
  • Take without regard to meals. Avoid alcohol.

Targets

1. Mu-type opioid receptor

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Mu-type opioid receptor P35372 Details

References:

  1. Quigley C: Hydromorphone for acute and chronic pain. Cochrane Database Syst Rev. 2002;(1):CD003447. Pubmed
  2. Inturrisi CE: Clinical pharmacology of opioids for pain. Clin J Pain. 2002 Jul-Aug;18(4 Suppl):S3-13. Pubmed
  3. Sarhill N, Walsh D, Nelson KA: Hydromorphone: pharmacology and clinical applications in cancer patients. Support Care Cancer. 2001 Mar;9(2):84-96. Pubmed
  4. Kumar P, Sunkaraneni S, Sirohi S, Dighe SV, Walker EA, Yoburn BC: Hydromorphone efficacy and treatment protocol impact on tolerance and mu-opioid receptor regulation. Eur J Pharmacol. 2008 Nov 12;597(1-3):39-45. Epub 2008 Aug 30. Pubmed

2. Delta-type opioid receptor

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: partial agonist

Components

Name UniProt ID Details
Delta-type opioid receptor P41143 Details

References:

  1. Fang X, Larson DL, Portoghese PS: 7-spirobenzocyclohexyl derivatives of naltrexone, oxymorphone, and hydromorphone as selective opioid receptor ligands. J Med Chem. 1997 Sep 12;40(19):3064-70. Pubmed
  2. Hennies HH, Friderichs E, Schneider J: Receptor binding, analgesic and antitussive potency of tramadol and other selected opioids. Arzneimittelforschung. 1988 Jul;38(7):877-80. Pubmed
  3. Jiang Q, Sebastian A, Archer S, Bidlack JM: 5 beta-Methyl-14 beta-(p-nitrocinnamoylamino)-7,8-dihydromorphinone and its corresponding N-cyclopropylmethyl analog, N-cyclopropylmethylnor-5 beta-methyl-14 beta-(p-nitrocinnamoylamino)- 7,8-dihydromorphinone: mu-selective irreversible opioid antagonists. J Pharmacol Exp Ther. 1994 Mar;268(3):1107-13. Pubmed
  4. Guay DR: Use of oral oxymorphone in the elderly. Consult Pharm. 2007 May;22(5):417-30. Pubmed
  5. Hartvig P, Neil A, Terenius L, Antoni G, Rimland A, Ulin J, Langstrom B: Brain and plasma kinetics of the opioid 11C-hydromorphone in two macaque species. Pharmacol Toxicol. 1989 Sep;65(3):214-6. Pubmed
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

3. Kappa-type opioid receptor

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Kappa-type opioid receptor P41145 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Gharagozlou P, Hashemi E, DeLorey TM, Clark JD, Lameh J: Pharmacological profiles of opioid ligands at kappa opioid receptors. BMC Pharmacol. 2006 Jan 25;6:3. Pubmed

Enzymes

1. Cytochrome P450 3A4

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 3A4 P08684 Details

References:

  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. Pubmed
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

2. Cytochrome P450 2C9

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 2C9 P11712 Details

References:

  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. Pubmed
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

3. Cytochrome P450 2D6

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 2D6 P10635 Details

References:

  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. Pubmed
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

4. Prostaglandin G/H synthase 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Prostaglandin G/H synthase 1 P23219 Details

References:

  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. Pubmed

5. UDP-glucuronosyltransferase 1-9

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
UDP-glucuronosyltransferase 1-9 O60656 Details

References:

  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. Pubmed

Comments
comments powered by Disqus
Drug created on June 13, 2005 07:24 / Updated on January 20, 2014 21:22