Identification

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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
Thumb
Synonyms
  • (-)-(5R)-4,5-Epoxy-3-hydroxy-9α-methylmorphinan-6-one
  • 4,5-Epoxy-3-hydroxy-17-methylmorphinan-6-one
  • 4,5alpha-Epoxy-3-hydroxy-17-methyl-6-morphinanone
  • 6-Deoxy-7,8-dihydro-6-oxomorphine
  • 7,8-Dihydromorphinone
  • Dihydromorfinon
  • Dihydromorphinone
  • Dimorphone
  • Hidromorfona
  • Hydromorfona
  • Hydromorphone
  • Hydromorphonum
  • Idromorfone
External IDs
IDS-NH-004 / N02AA03 / NSC-19046
Product Ingredients
IngredientUNIICASInChI Key
Hydromorphone hydrochlorideL960UP2KRW71-68-1XHILEZUETWRSHC-NRGUFEMZSA-N
Hydromorphone sulfate75Y990NH3Z25333-57-7JBBINZRUTLUBFR-NRGUFEMZSA-N
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
DilaudidTablet2 mg/1OralLake Erie Medical &Surgical Supply Dba Quality Care Products Llc2011-12-012014-12-31Us
DilaudidTablet4 mg/1OralMckesson Rxpak Inc1956-01-01Not applicableUs
DilaudidLiquid1 mgOralPurdue Pharma1989-12-312018-01-23Canada
DilaudidTablet4 mgOralPurdue Pharma1984-12-31Not applicableCanada
DilaudidSolution5 mg/5mLOralRhodes Pharmaceuticals L.P.2017-05-15Not applicableUs
DilaudidTablet8 mg/1OralPurdue Pharma LP1956-01-01Not applicableUs
DilaudidTablet4 mg/1OralLake Erie Medical Dba Quality Care Produts Llc1956-01-012013-03-26Us
DilaudidTablet2 mgOralPurdue Pharma1984-12-31Not applicableCanada
DilaudidInjection, solution4 mg/1mLIntramuscular; Intravenous; SubcutaneousPurdue Pharma LP1926-01-01Not applicableUs
DilaudidTablet8 mg/1OralRhodes Pharmaceuticals L.P.2017-05-15Not applicableUs
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-hydromorphoneTabletOralApotex Corporation2012-12-18Not applicableCanada
Apo-hydromorphoneTabletOralApotex Corporation2012-12-18Not applicableCanada
Apo-hydromorphoneTabletOralApotex Corporation2012-12-18Not applicableCanada
Apo-hydromorphoneTabletOralApotex Corporation2012-12-18Not applicableCanada
Apo-hydromorphone CRCapsule, extended releaseOralApotex Corporation2018-10-10Not applicableCanada
Apo-hydromorphone CRCapsule, extended releaseOralApotex Corporation2018-10-10Not applicableCanada
Apo-hydromorphone CRCapsule, extended releaseOralApotex Corporation2018-10-10Not applicableCanada
Apo-hydromorphone CRCapsule, extended releaseOralApotex Corporation2018-10-10Not applicableCanada
Apo-hydromorphone CRCapsule, extended releaseOralApotex Corporation2018-10-10Not applicableCanada
Apo-hydromorphone CRCapsule, extended releaseOralApotex Corporation2018-10-10Not applicableCanada
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Hydromorphone HClHydromorphone hydrochloride (2 mg/1mL)Injection, solutionIntravenousCantrell Drug Company2014-08-20Not applicableUs
Hydromorphone HClHydromorphone hydrochloride (0.5 mg/1mL)Injection, solutionIntravenousCantrell Drug Company2014-08-13Not applicableUs
Hydromorphone HClHydromorphone hydrochloride (0.2 mg/1mL)Injection, solutionIntravenousCantrell Drug Company2010-08-232017-12-06Us
Hydromorphone HClHydromorphone hydrochloride (0.1 mg/1mL)Injection, solutionIntravenousCantrell Drug Company2014-08-21Not applicableUs
Hydromorphone HClHydromorphone hydrochloride (1 mg/1mL)Injection, solutionIntravenousCantrell Drug Company2012-08-302017-12-06Us
Hydromorphone HClHydromorphone hydrochloride (10 mg/1mL)Injection, solutionIntravenousCantrell Drug Company2014-08-13Not applicableUs
Hydromorphone HClHydromorphone hydrochloride (0.4 mg/1mL)Injection, solutionIntravenousCantrell Drug Company2014-08-13Not applicableUs
Hydromorphone HydrochlorideHydromorphone hydrochloride (2 mg/1mL)Injection, solutionIntramuscular; Intravenous; SubcutaneousHospira, Inc.2018-08-232021-10-31Us
Hydromorphone HydrochlorideHydromorphone hydrochloride (2 mg/1mL)InjectionIntramuscular; Intravenous; SubcutaneousWest-Ward Pharmaceuticals Corp.1972-01-01Not applicableUs
Hydromorphone HydrochlorideHydromorphone hydrochloride (2 mg/1mL)InjectionIntramuscular; Intravenous; SubcutaneousWest-Ward Pharmaceuticals Corp.1972-01-01Not applicableUs
Categories
UNII
Q812464R06
CAS number
466-99-9
Weight
Average: 285.3377
Monoisotopic: 285.136493479
Chemical Formula
C17H19NO3
InChI Key
WVLOADHCBXTIJK-YNHQPCIGSA-N
InChI
InChI=1S/C17H19NO3/c1-18-7-6-17-10-3-5-13(20)16(17)21-15-12(19)4-2-9(14(15)17)8-11(10)18/h2,4,10-11,16,19H,3,5-8H2,1H3/t10-,11+,16-,17-/m0/s1
IUPAC Name
(1S,5R,13R,17R)-10-hydroxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7(18),8,10-trien-14-one
SMILES
[H][C@@]12OC3=C(O)C=CC4=C3[C@@]11CCN(C)[C@]([H])(C4)[C@]1([H])CCC2=O

Pharmacology

Indication

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

TargetActionsOrganism
AMu-type opioid receptor
agonist
Humans
ADelta-type opioid receptor
partial agonist
Humans
AKappa-type opioid receptor
agonist
Humans
Additional Data Available
Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available
Contraindications

Structured 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.

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Blackbox Warnings

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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 hydromorphone 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
PathwayCategory
Hydromorphone Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
(R)-warfarinThe metabolism of (R)-warfarin can be decreased when combined with Hydromorphone.
(S)-WarfarinThe metabolism of (S)-Warfarin can be decreased when combined with Hydromorphone.
2,5-Dimethoxy-4-ethylamphetamine2,5-Dimethoxy-4-ethylamphetamine may increase the analgesic activities of Hydromorphone.
2,5-Dimethoxy-4-ethylthioamphetamine2,5-Dimethoxy-4-ethylthioamphetamine may increase the analgesic activities of Hydromorphone.
4-Bromo-2,5-dimethoxyamphetamine4-Bromo-2,5-dimethoxyamphetamine may increase the analgesic activities of Hydromorphone.
4-MethoxyamphetamineThe risk or severity of adverse effects can be increased when Hydromorphone is combined with 4-Methoxyamphetamine.
5-methoxy-N,N-dimethyltryptamineThe risk or severity of adverse effects can be increased when Hydromorphone is combined with 5-methoxy-N,N-dimethyltryptamine.
7-NitroindazoleThe risk or severity of adverse effects can be increased when Hydromorphone is combined with 7-Nitroindazole.
7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline may increase the serotonergic activities of Hydromorphone.
AbacavirHydromorphone may decrease the excretion rate of Abacavir which could result in a higher serum level.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    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
  1. Abi-Aad KR, Derian A: Hydromorphone . [PubMed:29261877]
  2. 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]
  3. Trescot AM, Datta S, Lee M, Hansen H: Opioid pharmacology. Pain Physician. 2008 Mar;11(2 Suppl):S133-53. [PubMed:18443637]
  4. Overholser BR, Foster DR: Opioid pharmacokinetic drug-drug interactions. Am J Manag Care. 2011 Sep;17 Suppl 11:S276-87. [PubMed:21999760]
  5. 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]
  6. 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]
  7. 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]
  8. 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]
  9. FDA approvals [Link]
  10. Clinical trials [Link]
  11. 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
PhaseStatusPurposeConditionsCount
0CompletedTreatmentLumbar Spinal Instability / Lumbar Spine Degeneration / Spinal Stenosis of Lumbar Region1
0CompletedTreatmentPain1
0RecruitingSupportive CareMetastatic Malignant Neoplasm / Neoplasms, Malignant / Pain1
1CompletedNot AvailableHealthy Volunteers1
1CompletedNot AvailableHeroin Dependence / Opioid-Related Disorders1
1CompletedTreatmentAddictions / Opioid Dependence / Pain1
1CompletedTreatmentAnalgesia2
1CompletedTreatmentAnalgesics, Opioid / Pain1
1CompletedTreatmentHealthy Volunteers2
1CompletedTreatmentOpioid-Related Disorders / Pain, Chronic1
1CompletedTreatmentPain1
1CompletedTreatmentPain / Pain, Acute1
1CompletedTreatmentSubstance Abuse1
1Not Yet RecruitingOtherHealthy Volunteers1
1RecruitingBasic ScienceOpioid-use Disorder / Pain, Acute1
1SuspendedOtherNalbuphine / Opioid Abuse1
1TerminatedHealth Services ResearchCesarean Section / Obstetric Anesthesia1
1, 2CompletedTreatmentOpioid Abuse / Opioid Addiction / Stimulant Abuse / Stimulant Addiction1
1, 2TerminatedTreatmentWound Healing1
2Active Not RecruitingTreatmentAdenotonsillitis / Tonsillitis1
2CompletedNot AvailableHeroin Dependence / Opioid-Related Disorders1
2CompletedTreatmentAnalgesia / Orthopedic Procedures / Postoperative pain1
2CompletedTreatmentBack Pain Lower Back1
2CompletedTreatmentCesarean Section / Pain1
2CompletedTreatmentLabour Pain1
2CompletedTreatmentOpiate Dependence1
2CompletedTreatmentOpioid Use Disorders1
2CompletedTreatmentPain2
2CompletedTreatmentPain, Acute1
2CompletedTreatmentPostoperative pain1
2RecruitingTreatmentMusculoskeletal Injuries1
2RecruitingTreatmentPain, Acute1
2WithdrawnTreatmentHb-SS Disease With Vasoocclusive Pain / Hemoglobin SS Disease With Crisis / Hemoglobin SS Disease With Vasoocclusive Crisis / Other Sickle Cell Disease With Vaso-Occlusive Pain / Sickle Cell Disorders1
2, 3CompletedSupportive CareChronic Obstructive Pulmonary Disease (COPD)1
2, 3CompletedTreatmentConstipation1
2, 3CompletedTreatmentPain, Acute1
3CompletedSupportive CareManagement of Chronic Pain1
3CompletedSupportive CarePain / Prostate Cancer1
3CompletedTreatmentAnalgesics, Opioid / Pain4
3CompletedTreatmentAnalgesics / Opioids / Pain1
3CompletedTreatmentBack Pain Lower Back1
3CompletedTreatmentBack Pain Lower Back Chronic1
3CompletedTreatmentHeroin Dependence / Opioid Dependence1
3CompletedTreatmentKnee Osteoarthritis (Knee OA) / Osteoarthritis, Hip2
3CompletedTreatmentKnee Osteoarthritis (Knee OA) / Osteoarthritis, Hip / Pain1
3CompletedTreatmentPain4
3CompletedTreatmentPain, Acute3
3CompletedTreatmentPain, Chronic2
3CompletedTreatmentPostoperative paralytic ileus1
3RecruitingSupportive CareBreast - Female1
3RecruitingSupportive CareDiseases of Liver / Liver and Intrahepatic Bile Duct Disorder1
3RecruitingSupportive CareIntraoperative Complications / Malignant Female Reproductive System Neoplasm / Pain1
3RecruitingTreatmentPain, Cancer1
3RecruitingTreatmentSickle Cell Disorders1
3TerminatedTreatmentBack Pain, Unspecified / Lumbar Spine Fusion / Pain1
3TerminatedTreatmentChronic Non-Malignant Pain1
3TerminatedTreatmentFracture Bone / Pain, Acute / Trauma, Multiple1
3TerminatedTreatmentNeoplasms / Pain1
3TerminatedTreatmentPain, Chronic1
3Unknown StatusSupportive CareMalignancies / Pain1
3Unknown StatusTreatmentCancer Related Pain (Breakthrough Pain)1
3WithdrawnTreatmentMucositis1
4Active Not RecruitingSupportive CareAdvanced Cancers / Pain1
4Active Not RecruitingTreatmentPostoperative pain1
4Active Not RecruitingTreatmentObstetrical analgesia therapy1
4CompletedNot AvailablePain2
4CompletedBasic ScienceHealthy Volunteers1
4CompletedPreventionCaesarean Sections1
4CompletedSupportive CareSickle Cell Disorders1
4CompletedTreatmentAbdominal Pain1
4CompletedTreatmentAcute Postoperative Pain1
4CompletedTreatmentAcute Postoperative Pain / Chronic Persistent Surgical Pain / Hydromorphone Use / Patients Satisfaction1
4CompletedTreatmentBack Pain Lower Back1
4CompletedTreatmentBreakthrough Pain / Pain, Chronic / Pain, Intractable1
4CompletedTreatmentCesarean Section / Obstetrical analgesia therapy1
4CompletedTreatmentConstipation / Narcotic Use / Nausea / Pain1
4CompletedTreatmentLabour Pain1
4CompletedTreatmentMalignancies / Pain1
4CompletedTreatmentMigraine1
4CompletedTreatmentNausea1
4CompletedTreatmentPain5
4CompletedTreatmentPain, Acute3
4CompletedTreatmentPain, Cancer2
4CompletedTreatmentPain, Neuropathic1
4CompletedTreatmentPelvic Organ Prolapse (POP) / Postoperative pain1
4CompletedTreatmentPost Operative Pain1
4CompletedTreatmentPostoperative pain3
4CompletedTreatmentPostoperative pain / Thoracic Surgery, Video-Assisted1
4CompletedTreatmentUnilateral Knee Arthroplasty1
4CompletedTreatmentAcute, severe Pain1
4Not Yet RecruitingSupportive CareAnalgesia, Patient-Controlled1
4Not Yet RecruitingTreatmentAnalgesics, Opioid / Anti-Inflammatory Agents, Non-Steroidal / Child/Adolescent Problems / Emergency Service, Hospital / Fentanyl / Ibuprofen / Pain, Acute1
4Not Yet RecruitingTreatmentPostoperative pain1
4RecruitingDiagnosticProlonged QT Interval1
4RecruitingOtherOpioid Substitution Treatment1
4RecruitingPreventionPain / Rotator Cuff Injury1
4RecruitingSupportive CareColon Diverticulosis / Colonic Neoplasms / Constipation / Constipation Drug Induced / Diverticulitis, Colonic / Ileus / Ileus paralytic / Ileus; Mechanical / Malignant Neoplasm of Colon / Postoperative pain / Rectum Cancer / Rectum Neoplasm1
4RecruitingTreatmentOpioids Use / Postoperative pain1
4RecruitingTreatmentPain1
4RecruitingTreatmentPain, Chronic1
4RecruitingTreatmentPost Operative Nausea and Vomiting (PONV) / Postoperative Hemorrhages / Postoperative pain / Weight Changes1
4RecruitingTreatmentRib Fracture Multiple / Rib Fractures1
4TerminatedTreatmentFusion of Spine, Lumbar Region1
4TerminatedTreatmentPain2
4TerminatedTreatmentPectus Excavatum1
4TerminatedTreatmentPostoperative pain1
4Unknown StatusNot AvailableAdults / Healthy Volunteers / Humans / Parturient1
4WithdrawnTreatmentBMI >30 kg/m2 / Postoperative pain / Respiratory Insufficiency1
4WithdrawnTreatmentPain, Acute / Postoperative pain / Surgery, Colorectal1
Not AvailableActive Not RecruitingTreatmentPain / Post Operative Nausea and Vomiting (PONV)1
Not AvailableActive Not RecruitingTreatmentRib Fractures1
Not AvailableCompletedNot AvailableCancer Related Pain (Breakthrough Pain) / Pain, Cancer / Pain, Neuropathic / Tumors1
Not AvailableCompletedNot AvailableCervical Cancers / Endometrial Cancer / Fallopian Tube Cancer / Ovarian Cancer / Pain / Perioperative/Postoperative Complications / Sarcomas1
Not AvailableCompletedNot AvailableGeneral Surgery1
Not AvailableCompletedBasic ScienceHealthy Volunteers1
Not AvailableCompletedPreventionPost Operative Nausea and Vomiting (PONV)1
Not AvailableCompletedSupportive CarePain Measurement / Visual Analog Pain Scale1
Not AvailableCompletedTreatmentBack Pain Lower Back1
Not AvailableCompletedTreatmentBreast Cancer1
Not AvailableCompletedTreatmentConditions Requiring Colorectal Surgery1
Not AvailableCompletedTreatmentEpidural Analgesia1
Not AvailableCompletedTreatmentObstetric Surgical Procedures / Obstetrical analgesia therapy1
Not AvailableCompletedTreatmentOpioid-Related Disorders1
Not AvailableCompletedTreatmentPain Conditions1
Not AvailableCompletedTreatmentPost Operative Pain1
Not AvailableNot Yet RecruitingPreventionCaudal epidural block therapy / Postoperative pain / Surgery, Cardiac1
Not AvailableRecruitingNot AvailableAnaesthesia therapy / Pain1
Not AvailableRecruitingPreventionPostoperative pain1
Not AvailableRecruitingPreventionPregnancy1
Not AvailableRecruitingTreatmentHepatectomy / Neoplasms, Hepatic / Postoperative pain1
Not AvailableRecruitingTreatmentNausea / Pain1
Not AvailableTerminatedSupportive CarePain / Respiratory Depression1
Not AvailableTerminatedTreatmentLaparoscopic Colorectal Resection1
Not AvailableTerminatedTreatmentPain, Acute1
Not AvailableUnknown StatusNot AvailableAnalgesic Response1
Not AvailableUnknown StatusTreatmentPain1
Not AvailableWithdrawnTreatmentPain / Ventilatory Depression1

Pharmacoeconomics

Manufacturers
  • Purdue pharma lp
  • Purdue pharmaceutical products lp
  • Akorn inc
  • Barr laboratories inc
  • Hospira inc
  • Watson laboratories inc
  • Roxane laboratories inc
  • Mallinckrodt inc
  • Actavis totowa llc
  • Kv pharmaceutical co
  • Lannett holdings inc
  • Tyco healthcare mallinckrodt
Packagers
  • Abbott Laboratories Ltd.
  • Akorn Inc.
  • Barr Pharmaceuticals
  • BASF Corp.
  • Baxter International Inc.
  • Blenheim Pharmacal
  • Bristol-Myers Squibb Co.
  • Cardinal Health
  • D.M. Graham Laboratories Inc.
  • Direct Dispensing Inc.
  • Endo Pharmaceuticals Inc.
  • Ethex Corp.
  • Hospira Inc.
  • KV Pharmaceutical Co.
  • Lake Erie Medical and Surgical Supply
  • Lannett Co. Inc.
  • Mallinckrodt Inc.
  • Mckesson Corp.
  • Nucare Pharmaceuticals Inc.
  • Paddock Labs
  • PD-Rx Pharmaceuticals Inc.
  • Pharmakon
  • Pharmedium
  • Physicians Total Care Inc.
  • Purdue Pharma LP
  • Qualitest
  • Rhodes Pharmaceutical LP
  • Roxane Labs
  • Stat Rx Usa
Dosage forms
FormRouteStrength
Injection, solutionIntramuscular; Intravenous; Subcutaneous1 mg/1mL
Injection, solutionIntramuscular; Intravenous; Subcutaneous2 mg/1mL
Injection, solutionIntramuscular; Intravenous; Subcutaneous4 mg/1mL
LiquidIntramuscular; Intravenous; Subcutaneous2 mg
LiquidOral1 mg
LiquidOral5 mg/5mL
Powder, for solutionIntramuscular; Intravenous; Subcutaneous250 mg
SolutionOral5 mg/5mL
SuppositoryRectal3 mg
TabletOral1 mg
TabletOral2 mg
TabletOral4 mg
TabletOral8 mg
Injection, powder, lyophilized, for solutionIntramuscular; Intravenous; Subcutaneous10 mg/1mL
LiquidIntramuscular; Intravenous; Subcutaneous10 mg
PowderIntramuscular; Intravenous; Subcutaneous250 mg/25mL
SolutionIntramuscular; Intravenous; Subcutaneous500 mg/50mL
LiquidIntramuscular; Intravenous; Subcutaneous
Tablet, extended releaseOral12 mg/1
Tablet, extended releaseOral16 mg/1
Tablet, extended releaseOral8 mg/1
Capsule, extended releaseOral
Injection, solutionIntravenous0.1 mg/1mL
Injection, solutionIntravenous0.2 mg/1mL
Injection, solutionIntravenous0.4 mg/1mL
Injection, solutionIntravenous0.5 mg/1mL
Injection, solutionIntravenous1 mg/1mL
Injection, solutionIntravenous10 mg/1mL
Injection, solutionIntravenous2 mg/1mL
SolutionOral5 mg/1mL
InjectionIntramuscular; Intravenous; Subcutaneous2 mg/1mL
InjectionParenteral10 mg/1mL
Injection, solutionIntramuscular; Intravenous; Subcutaneous10 mg/1mL
SolutionOral1 mg/1mL
SuppositoryRectal3 mg/1
TabletOral2 mg/1
TabletOral4 mg/1
TabletOral8 mg/1
Tablet, extended releaseOral32 mg/1
Tablet, film coatedOral2 mg/1
Tablet, film coatedOral4 mg/1
Tablet, film coatedOral8 mg/1
Tablet, film coated, extended releaseOral12 mg/1
Tablet, film coated, extended releaseOral16 mg/1
Tablet, film coated, extended releaseOral32 mg/1
Tablet, film coated, extended releaseOral8 mg/1
SolutionIntramuscular; Intravenous; Subcutaneous
SolutionIntravenous
Tablet, extended releaseOral
Capsule, extended releaseOral12 mg/1
Capsule, extended releaseOral16 mg/1
Capsule, extended releaseOral24 mg/1
Capsule, extended releaseOral32 mg/1
SyrupOral
SuppositoryRectal
TabletOral
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
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5968551No1999-10-192011-12-24Us
US6589960No2003-07-082020-11-09Us
US9248229No2016-02-022034-03-12Us
US9731082No2017-08-152032-04-23Us
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

    Learn more

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)Decomposes at 305ºC'MSDS'
boiling point (°C)Decomposes at 305ºC'MSDS'
water solubilityHighly solubleTrescot A. et al. (2008). Pain Physician.
logP1.06Agilent. SAMHSA-Compilant Analysis of Opiates.
pKa8.2Agilent. SAMHSA-Compilant Analysis of Opiates.
Predicted Properties
PropertyValueSource
Water Solubility4.39 mg/mLALOGPS
logP1.69ALOGPS
logP1.62ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)10.11ChemAxon
pKa (Strongest Basic)8.59ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area49.77 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity78.26 m3·mol-1ChemAxon
Polarizability30.02 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9931
Caco-2 permeable+0.8647
P-glycoprotein substrateSubstrate0.8174
P-glycoprotein inhibitor INon-inhibitor0.8497
P-glycoprotein inhibitor IINon-inhibitor0.9641
Renal organic cation transporterInhibitor0.6374
CYP450 2C9 substrateNon-substrate0.7925
CYP450 2D6 substrateSubstrate0.8618
CYP450 3A4 substrateSubstrate0.7571
CYP450 1A2 substrateNon-inhibitor0.6918
CYP450 2C9 inhibitorNon-inhibitor0.9539
CYP450 2D6 inhibitorNon-inhibitor0.5197
CYP450 2C19 inhibitorNon-inhibitor0.8088
CYP450 3A4 inhibitorNon-inhibitor0.8177
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9413
Ames testNon AMES toxic0.7214
CarcinogenicityNon-carcinogens0.9554
BiodegradationNot ready biodegradable0.9815
Rat acute toxicity2.9191 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8906
hERG inhibition (predictor II)Non-inhibitor0.8992
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

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

Taxonomy

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

Targets

Details
1. Mu-type opioid receptor
Kind
Protein
Organism
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
  1. Quigley C: Hydromorphone for acute and chronic pain. Cochrane Database Syst Rev. 2002;(1):CD003447. [PubMed:11869661]
  2. Inturrisi CE: Clinical pharmacology of opioids for pain. Clin J Pain. 2002 Jul-Aug;18(4 Suppl):S3-13. [PubMed:12479250]
  3. Sarhill N, Walsh D, Nelson KA: Hydromorphone: pharmacology and clinical applications in cancer patients. Support Care Cancer. 2001 Mar;9(2):84-96. [PubMed:11305075]
  4. Kumar P, Sunkaraneni S, Sirohi S, Dighe SV, Walker EA, Yoburn BC: Hydromorphone efficacy and treatment protocol impact on tolerance and mu-opioid receptor regulation. Eur J Pharmacol. 2008 Nov 12;597(1-3):39-45. doi: 10.1016/j.ejphar.2008.08.025. Epub 2008 Aug 30. [PubMed:18789923]
Kind
Protein
Organism
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
  1. Fang X, Larson DL, Portoghese PS: 7-spirobenzocyclohexyl derivatives of naltrexone, oxymorphone, and hydromorphone as selective opioid receptor ligands. J Med Chem. 1997 Sep 12;40(19):3064-70. [PubMed:9301669]
  2. Hennies HH, Friderichs E, Schneider J: Receptor binding, analgesic and antitussive potency of tramadol and other selected opioids. Arzneimittelforschung. 1988 Jul;38(7):877-80. [PubMed:2849950]
  3. Jiang Q, Sebastian A, Archer S, Bidlack JM: 5 beta-Methyl-14 beta-(p-nitrocinnamoylamino)-7,8-dihydromorphinone and its corresponding N-cyclopropylmethyl analog, N-cyclopropylmethylnor-5 beta-methyl-14 beta-(p-nitrocinnamoylamino)- 7,8-dihydromorphinone: mu-selective irreversible opioid antagonists. J Pharmacol Exp Ther. 1994 Mar;268(3):1107-13. [PubMed:7511163]
  4. Guay DR: Use of oral oxymorphone in the elderly. Consult Pharm. 2007 May;22(5):417-30. [PubMed:17658959]
  5. Hartvig P, Neil A, Terenius L, Antoni G, Rimland A, Ulin J, Langstrom B: Brain and plasma kinetics of the opioid 11C-hydromorphone in two macaque species. Pharmacol Toxicol. 1989 Sep;65(3):214-6. [PubMed:2478994]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
Kind
Protein
Organism
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
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Gharagozlou P, Hashemi E, DeLorey TM, Clark JD, Lameh J: Pharmacological profiles of opioid ligands at kappa opioid receptors. BMC Pharmacol. 2006 Jan 25;6:3. [PubMed:16433932]

Enzymes

Kind
Protein
Organism
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
  1. Benetton SA, Borges VM, Chang TK, McErlane KM: Role of individual human cytochrome P450 enzymes in the in vitro metabolism of hydromorphone. Xenobiotica. 2004 Apr;34(4):335-44. doi: 10.1080/00498250310001657559 . [PubMed:15268978]
Kind
Protein
Organism
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
  1. 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
  1. Overholser BR, Foster DR: Opioid pharmacokinetic drug-drug interactions. Am J Manag Care. 2011 Sep;17 Suppl 11:S276-87. [PubMed:21999760]
  2. 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
  1. Abi-Aad KR, Derian A: Hydromorphone . [PubMed:29261877]

Drug created on June 13, 2005 07:24 / Updated on December 08, 2019 20:10