U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C17H19NO3
Molecular Weight 285.3383
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of HYDROMORPHONE

SMILES

CN1CC[C@@]23[C@@]4([H])CCC(=O)[C@]2([H])Oc5c(ccc(C[C@]41[H])c53)O

InChI

InChIKey=WVLOADHCBXTIJK-YNHQPCIGSA-N
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

HIDE SMILES / InChI
Hydromorphone (also known as dihydromorphinone and the brand name Dilaudid among others) is a more potent opioid analgesic than morphine and is used for moderate to severe pain. It can be administered by injection, by infusion, by mouth, and rectally. Oral bioavailability is low. The kidney excretes hydromorphone and its metabolites. Some metabolites may have greater analgesic activity than hydromorphone itself but are unlikely to contribute to the pharmacological activity of hydromorphone. With the exception of pruritus, sedation and nausea and vomiting, which may occur less after hydromorphone than after morphine, the side-effects of these drugs are similar. 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. It also binds with kappa and delta receptors which are thought to mediate spinal analgesia, miosis and sedation.

Approval Year

Targets

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
DILAUDID-HP

Approved Use

DILAUDID INJECTION is indicated for the management of pain severe enough to require an opioid analgesic and for which alternate treatments are inadequate. DILAUDID-HP INJECTION is indicated for use in opioid-tolerant patients who require higher doses of opioids for the management of pain severe enough to require an opioid analgesic and for which alternate treatments are inadequate. Patients considered opioid tolerant are those who are taking for one week or longer,around-the-clock medicine consisting of at least 60 mg oral morphine per day, or at least 25 mcg transdermal fentanyl per hour, or at least 30 mg oral oxycodone per day, or at least 8 g oral hydromorphone per day, or at least 25 mg oral oxymorphone per day, or at least 60 mg oral hydrocodone per day, or an equianalgesic dose of another opioid for one week or longer. Patients must remain on around-the-clock opioids while administering DILAUDID-HP

Launch Date

442627200000
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
5.5 ng/mL
8 mg single, oral
dose: 8 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
HYDROMORPHONE HYDROCHLORIDE plasma
Homo sapiens
population: HEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
23.7 ng × h/mL
8 mg single, oral
dose: 8 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
HYDROMORPHONE HYDROCHLORIDE plasma
Homo sapiens
population: HEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
2.6 h
8 mg single, oral
dose: 8 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
HYDROMORPHONE HYDROCHLORIDE plasma
Homo sapiens
population: HEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
81%
8 mg single, oral
dose: 8 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
HYDROMORPHONE HYDROCHLORIDE plasma
Homo sapiens
population: HEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
540 mg single, intrathecal
Overdose
Dose: 540 mg
Route: intrathecal
Route: single
Dose: 540 mg
Sources:
unhealthy, 27
Health Status: unhealthy
Age Group: 27
Sex: F
Sources:
Disc. AE: Sleepiness, Nausea...
AEs leading to
discontinuation/dose reduction:
Sleepiness
Nausea
Sources:
2 mg 3 times / day multiple, intravenous
Recommended
Dose: 2 mg, 3 times / day
Route: intravenous
Route: multiple
Dose: 2 mg, 3 times / day
Sources:
unhealthy, 40
Health Status: unhealthy
Age Group: 40
Sex: M
Sources:
Disc. AE: Respiratory arrest...
AEs leading to
discontinuation/dose reduction:
Respiratory arrest (grade 5)
Sources:
4 mg 4 times / day multiple, oral
Recommended
Dose: 4 mg, 4 times / day
Route: oral
Route: multiple
Dose: 4 mg, 4 times / day
Sources:
unhealthy, 67.7
Health Status: unhealthy
Age Group: 67.7
Sex: M+F
Sources:
Disc. AE: Somnolence, Aspiration pneumonia...
AEs leading to
discontinuation/dose reduction:
Somnolence (serious, 1.14%)
Aspiration pneumonia (grade 5, 1.14%)
Toxic skin eruption (serious, 1.14%)
Nausea and vomiting (serious, 1.14%)
Sources:
10 mg single, intravenous
Overdose
Dose: 10 mg
Route: intravenous
Route: single
Dose: 10 mg
Sources:
unhealthy
Health Status: unhealthy
Sources:
Disc. AE: Cardio-respiratory arrest...
AEs leading to
discontinuation/dose reduction:
Cardio-respiratory arrest (grade 5)
Sources:
2 mg 6 times / day multiple, subcutaneous|intramuscular
Recommended
Dose: 2 mg, 6 times / day
Route: subcutaneous|intramuscular
Route: multiple
Dose: 2 mg, 6 times / day
Sources:
unhealthy
Disc. AE: Respiratory depression...
AEs leading to
discontinuation/dose reduction:
Respiratory depression
Sources:
4 mg 6 times / day multiple, oral
Recommended
Dose: 4 mg, 6 times / day
Route: oral
Route: multiple
Dose: 4 mg, 6 times / day
Sources:
unhealthy
Disc. AE: Addiction, Abuse...
AEs leading to
discontinuation/dose reduction:
Addiction
Abuse
Respiratory depression (grade 3-5)
Withdrawal syndrome neonatal (grade 3-5)
Coma (grade 5)
Sources:
AEs

AEs

AESignificanceDosePopulation
Nausea Disc. AE
540 mg single, intrathecal
Overdose
Dose: 540 mg
Route: intrathecal
Route: single
Dose: 540 mg
Sources:
unhealthy, 27
Health Status: unhealthy
Age Group: 27
Sex: F
Sources:
Sleepiness Disc. AE
540 mg single, intrathecal
Overdose
Dose: 540 mg
Route: intrathecal
Route: single
Dose: 540 mg
Sources:
unhealthy, 27
Health Status: unhealthy
Age Group: 27
Sex: F
Sources:
Respiratory arrest grade 5
Disc. AE
2 mg 3 times / day multiple, intravenous
Recommended
Dose: 2 mg, 3 times / day
Route: intravenous
Route: multiple
Dose: 2 mg, 3 times / day
Sources:
unhealthy, 40
Health Status: unhealthy
Age Group: 40
Sex: M
Sources:
Aspiration pneumonia grade 5, 1.14%
Disc. AE
4 mg 4 times / day multiple, oral
Recommended
Dose: 4 mg, 4 times / day
Route: oral
Route: multiple
Dose: 4 mg, 4 times / day
Sources:
unhealthy, 67.7
Health Status: unhealthy
Age Group: 67.7
Sex: M+F
Sources:
Nausea and vomiting serious, 1.14%
Disc. AE
4 mg 4 times / day multiple, oral
Recommended
Dose: 4 mg, 4 times / day
Route: oral
Route: multiple
Dose: 4 mg, 4 times / day
Sources:
unhealthy, 67.7
Health Status: unhealthy
Age Group: 67.7
Sex: M+F
Sources:
Somnolence serious, 1.14%
Disc. AE
4 mg 4 times / day multiple, oral
Recommended
Dose: 4 mg, 4 times / day
Route: oral
Route: multiple
Dose: 4 mg, 4 times / day
Sources:
unhealthy, 67.7
Health Status: unhealthy
Age Group: 67.7
Sex: M+F
Sources:
Toxic skin eruption serious, 1.14%
Disc. AE
4 mg 4 times / day multiple, oral
Recommended
Dose: 4 mg, 4 times / day
Route: oral
Route: multiple
Dose: 4 mg, 4 times / day
Sources:
unhealthy, 67.7
Health Status: unhealthy
Age Group: 67.7
Sex: M+F
Sources:
Cardio-respiratory arrest grade 5
Disc. AE
10 mg single, intravenous
Overdose
Dose: 10 mg
Route: intravenous
Route: single
Dose: 10 mg
Sources:
unhealthy
Health Status: unhealthy
Sources:
Respiratory depression Disc. AE
2 mg 6 times / day multiple, subcutaneous|intramuscular
Recommended
Dose: 2 mg, 6 times / day
Route: subcutaneous|intramuscular
Route: multiple
Dose: 2 mg, 6 times / day
Sources:
unhealthy
Abuse Disc. AE
4 mg 6 times / day multiple, oral
Recommended
Dose: 4 mg, 6 times / day
Route: oral
Route: multiple
Dose: 4 mg, 6 times / day
Sources:
unhealthy
Addiction Disc. AE
4 mg 6 times / day multiple, oral
Recommended
Dose: 4 mg, 6 times / day
Route: oral
Route: multiple
Dose: 4 mg, 6 times / day
Sources:
unhealthy
Respiratory depression grade 3-5
Disc. AE
4 mg 6 times / day multiple, oral
Recommended
Dose: 4 mg, 6 times / day
Route: oral
Route: multiple
Dose: 4 mg, 6 times / day
Sources:
unhealthy
Withdrawal syndrome neonatal grade 3-5
Disc. AE
4 mg 6 times / day multiple, oral
Recommended
Dose: 4 mg, 6 times / day
Route: oral
Route: multiple
Dose: 4 mg, 6 times / day
Sources:
unhealthy
Coma grade 5
Disc. AE
4 mg 6 times / day multiple, oral
Recommended
Dose: 4 mg, 6 times / day
Route: oral
Route: multiple
Dose: 4 mg, 6 times / day
Sources:
unhealthy
PubMed

PubMed

TitleDatePubMed
Survey of pain management therapy provided for children with sickle cell disease.
1992 Apr
Clonazepam treatment of myoclonic contractions associated with high-dose opioids: case report.
1992 May
Opioid formulations: tailoring to the needs in chronic pain.
2001
Pharmacokinetics of oral immediate-release hydromorphone (Dilaudid IR) in subjects with moderate hepatic impairment.
2001
Pharmacokinetics of oral immediate-release hydromorphone (Dilaudid IR) in subjects with renal impairment.
2001
Pharmacokinetics of oral immediate-release hydromorphone (Dilaudid IR) in young and elderly subjects.
2001
Pharmacokinetics of oral immediate-release hydromorphone (Dilaudid IR) in male and female subjects.
2001
Effect of food on the pharmacokinetics of oral immediate-release hydromorphone (Dilaudid IR).
2001
Dose proportionality of the pharmacokinetics of oral immediate-release hydromorphone (Dilaudid IR).
2001
Opioid equianalgesic conversion: the right dose.
2001 Jul-Aug
The simultaneous determination of codeine, morphine, hydrocodone, hydromorphone, 6-acetylmorphine, and oxycodone in hair and oral fluid.
2002 Apr
A convenient synthesis of delta(7,8)-morphinan-6-one and its direct oxidation to 14-hydroxy-delta(7,8)-morphinan-6-one.
2002 Aug 5
Screening extemporaneously compounded intraspinal injections with the bacterial endotoxins test.
2002 Dec 15
[Opioid rotation in pain therapy. Case report].
2002 Jan
Breaking the deadlock over an Australian trial of injectable opioid maintenance.
2002 Jan 21
Synthesis and biological activity of 8beta-substituted hydrocodone indole and hydromorphone indole derivatives.
2002 Jan 21
The role of spinal opioid receptors in antinociceptive effects produced by intrathecal administration of hydromorphone and buprenorphine in the rat.
2002 Jun
The addition of hydromorphone to epidural fentanyl does not affect analgesia in early labour.
2002 Jun-Jul
Simultaneous determination of hydrocodone and hydromorphone in human plasma by liquid chromatography with tandem mass spectrometric detection.
2002 Mar 25
Postthoracotomy pain management.
2002 May
Dose conversion and titration with a novel, once-daily, OROS osmotic technology, extended-release hydromorphone formulation in the treatment of chronic malignant or nonmalignant pain.
2002 May
Separating politics and scientific research on heroin prescription.
2002 May 6
Pain and suffering in an adolescent with neuroblastoma.
2002 May-Jun
Opioid rotation in the treatment of joint pain. A review of 67 cases.
2002 Oct
Simultaneous quantitation of opioids in blood by GC-EI-MS analysis following deproteination, detautomerization of keto analytes, solid-phase extraction, and trimethylsilyl derivatization.
2002 Oct
Detection of cocaine analytes and opiates in nails from postmortem cases.
2002 Oct
Envenomation by the Mexican beaded lizard: a case report.
2003
Morphine and hydromorphone for postoperative analgesia: focus on safety.
2003 Apr
Embolized crospovidone (poly[N-vinyl-2-pyrrolidone]) in the lungs of intravenous drug users.
2003 Apr
Calculating opioid dose conversions #36.
2003 Aug
Summary version of the Standards, Options and Recommendations for the use of analgesia for the treatment of nociceptive pain in adults with cancer (update 2002).
2003 Aug
Is the analgesic effect of systemic lidocaine mediated through opioid receptors?
2003 Aug
A systematic review of hydromorphone in acute and chronic pain.
2003 Feb
Postoperative hypoxemia and hypercarbia in healthy dogs undergoing routine ovariohysterectomy or castration and receiving butorphanol or hydromorphone for analgesia.
2003 Feb 1
Quantification of the O- and N-demethylated metabolites of hydrocodone and oxycodone in human liver microsomes using liquid chromatography with ultraviolet absorbance detection.
2003 Feb 25
Long-term outcomes during treatment of chronic pain with intrathecal clonidine or clonidine/opioid combinations.
2003 Jul
Pharmacokinetics and bioavailability of single-dose intranasal hydromorphone hydrochloride in healthy volunteers.
2003 Jul
[Pain therapy with semisynthetic opioids. Patients have opioid-type side effects more rarely].
2003 Jul 10
Management of postoperative pain after T6 corpectomy: use of epidural bupivacaine and sufentanil--a case report.
2003 Jun
Oral oxycodone: new preparation. No better than oral morphine.
2003 Jun
Using saccadic eye movements as objective measures of tolerance in methadone dependent individuals during the hydromorphone challenge test.
2003 Mar
Changes in intraocular pressure and pupil size following intramuscular administration of hydromorphone hydrochloride and acepromazine in clinically normal dogs.
2003 Mar
Opioid ligands having delayed long-term antagonist activity: potential pharmacotherapies for opioid abuse.
2003 Mar
Pharmacokinetic drug interactions of morphine, codeine, and their derivatives: theory and clinical reality, part I.
2003 Mar-Apr
Antinociceptive effects of hydromorphone, bupivacaine and biphalin released from PLGA polymer after intrathecal implantation in rats.
2003 May
Effects of buprenorphine maintenance dose on mu-opioid receptor availability, plasma concentrations, and antagonist blockade in heroin-dependent volunteers.
2003 Nov
Antihyperalgesic effect of simultaneously released hydromorphone and bupivacaine from polymer fibers in the rat chronic constriction injury model.
2003 Nov 14
[Combined use of intrathecal morphine and diclofenac suppository for postoperative analgesia after caesarean section].
2003 Oct
The use of long-acting opioids in chronic pain management.
2003 Sep
Oral vs. i.v. hydromorphone. Add a measure of caution.
2003 Sep
Patents

Sample Use Guides

Subcutaneous or Intramuscular Administration: The usual starting dose of DILAUDID INJECTION is 1 mg to 2 mg every 2 to 3 hours as necessary. Depending on the clinical situation, the initial starting dose may be lowered in patients who are opioid naïve.
Route of Administration: Other
Name Type Language
HYDROMORPHONE
HSDB   INN   MI   VANDF   WHO-DD  
INN  
Official Name English
HYDROMORPHON
Common Name English
HYDROMORPHONE [WHO-DD]
Common Name English
HYDROCODONE HYDROGEN TARTRATE 2.5-HYDRATE SPECIFIED IMPURITY K [EP]
Common Name English
NOVOLAUDON
Common Name English
JURNISTA
Common Name English
HYDROMORPHONE [INN]
Common Name English
IDS-NH-004
Code English
HYDROMORPHONE [VANDF]
Common Name English
MORPHINAN-6-ONE, 4,5-EPOXY-3-HYDROXY-17-METHYL-, (5.ALPHA.)-
Systematic Name English
HYDROMORPHONE [MI]
Common Name English
NSC-19046
Code English
HYDROMORPHONE [HSDB]
Common Name English
4,5.ALPHA.-EPOXY-3-HYDROXY-17-METHYLMORPHINAN-6-ONE
Systematic Name English
N02AA03
Code English
DIMORPHONE
Common Name English
Classification Tree Code System Code
DEA NO. 9150
Created by admin on Sat Jun 26 00:32:26 UTC 2021 , Edited by admin on Sat Jun 26 00:32:26 UTC 2021
WHO-VATC QN02AA03
Created by admin on Sat Jun 26 00:32:26 UTC 2021 , Edited by admin on Sat Jun 26 00:32:26 UTC 2021
WHO-ATC N02AA03
Created by admin on Sat Jun 26 00:32:26 UTC 2021 , Edited by admin on Sat Jun 26 00:32:26 UTC 2021
WHO-VATC QN02AG04
Created by admin on Sat Jun 26 00:32:26 UTC 2021 , Edited by admin on Sat Jun 26 00:32:26 UTC 2021
NDF-RT N0000175684
Created by admin on Sat Jun 26 00:32:26 UTC 2021 , Edited by admin on Sat Jun 26 00:32:26 UTC 2021
NCI_THESAURUS C67413
Created by admin on Sat Jun 26 00:32:26 UTC 2021 , Edited by admin on Sat Jun 26 00:32:26 UTC 2021
LIVERTOX 487
Created by admin on Sat Jun 26 00:32:26 UTC 2021 , Edited by admin on Sat Jun 26 00:32:26 UTC 2021
NDF-RT N0000175690
Created by admin on Sat Jun 26 00:32:26 UTC 2021 , Edited by admin on Sat Jun 26 00:32:26 UTC 2021
NCI_THESAURUS C1506
Created by admin on Sat Jun 26 00:32:26 UTC 2021 , Edited by admin on Sat Jun 26 00:32:26 UTC 2021
WHO-ATC N02AA53
Created by admin on Sat Jun 26 00:32:26 UTC 2021 , Edited by admin on Sat Jun 26 00:32:26 UTC 2021
WHO-ATC N02AG04
Created by admin on Sat Jun 26 00:32:26 UTC 2021 , Edited by admin on Sat Jun 26 00:32:26 UTC 2021
Code System Code Type Description
INN
1770
Created by admin on Sat Jun 26 00:32:26 UTC 2021 , Edited by admin on Sat Jun 26 00:32:26 UTC 2021
PRIMARY
ChEMBL
CHEMBL398707
Created by admin on Sat Jun 26 00:32:26 UTC 2021 , Edited by admin on Sat Jun 26 00:32:26 UTC 2021
PRIMARY
CAS
466-99-9
Created by admin on Sat Jun 26 00:32:26 UTC 2021 , Edited by admin on Sat Jun 26 00:32:26 UTC 2021
PRIMARY
ECHA (EC/EINECS)
207-383-5
Created by admin on Sat Jun 26 00:32:26 UTC 2021 , Edited by admin on Sat Jun 26 00:32:26 UTC 2021
PRIMARY
WIKIPEDIA
HYDROMORPHONE
Created by admin on Sat Jun 26 00:32:26 UTC 2021 , Edited by admin on Sat Jun 26 00:32:26 UTC 2021
PRIMARY
EVMPD
SUB08070MIG
Created by admin on Sat Jun 26 00:32:26 UTC 2021 , Edited by admin on Sat Jun 26 00:32:26 UTC 2021
PRIMARY
IUPHAR
7082
Created by admin on Sat Jun 26 00:32:26 UTC 2021 , Edited by admin on Sat Jun 26 00:32:26 UTC 2021
PRIMARY
MERCK INDEX
M6110
Created by admin on Sat Jun 26 00:32:26 UTC 2021 , Edited by admin on Sat Jun 26 00:32:26 UTC 2021
PRIMARY Merck Index
DRUG BANK
DB00327
Created by admin on Sat Jun 26 00:32:26 UTC 2021 , Edited by admin on Sat Jun 26 00:32:26 UTC 2021
PRIMARY
HSDB
3341
Created by admin on Sat Jun 26 00:32:26 UTC 2021 , Edited by admin on Sat Jun 26 00:32:26 UTC 2021
PRIMARY
MESH
D004091
Created by admin on Sat Jun 26 00:32:26 UTC 2021 , Edited by admin on Sat Jun 26 00:32:26 UTC 2021
PRIMARY
LACTMED
Hydromorphone
Created by admin on Sat Jun 26 00:32:26 UTC 2021 , Edited by admin on Sat Jun 26 00:32:26 UTC 2021
PRIMARY
PUBCHEM
5284570
Created by admin on Sat Jun 26 00:32:26 UTC 2021 , Edited by admin on Sat Jun 26 00:32:26 UTC 2021
PRIMARY
RXCUI
3423
Created by admin on Sat Jun 26 00:32:26 UTC 2021 , Edited by admin on Sat Jun 26 00:32:26 UTC 2021
PRIMARY RxNorm
DRUG CENTRAL
1393
Created by admin on Sat Jun 26 00:32:26 UTC 2021 , Edited by admin on Sat Jun 26 00:32:26 UTC 2021
PRIMARY
FDA UNII
Q812464R06
Created by admin on Sat Jun 26 00:32:26 UTC 2021 , Edited by admin on Sat Jun 26 00:32:26 UTC 2021
PRIMARY
EPA CompTox
466-99-9
Created by admin on Sat Jun 26 00:32:26 UTC 2021 , Edited by admin on Sat Jun 26 00:32:26 UTC 2021
PRIMARY
NCI_THESAURUS
C62034
Created by admin on Sat Jun 26 00:32:26 UTC 2021 , Edited by admin on Sat Jun 26 00:32:26 UTC 2021
PRIMARY