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

Details

Stereochemistry ABSOLUTE
Molecular Formula C17H19NO3
Molecular Weight 285.3377
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of HYDROMORPHONE

SMILES

CN1CC[C@]23[C@H]4OC5=C(O)C=CC(C[C@@H]1[C@@H]2CCC4=O)=C35

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

Molecular Formula C17H19NO3
Molecular Weight 285.3377
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

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

1984
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
Antihyperalgesic effect of simultaneously released hydromorphone and bupivacaine from polymer fibers in the rat chronic constriction injury model.
2003-11-14
Effects of buprenorphine maintenance dose on mu-opioid receptor availability, plasma concentrations, and antagonist blockade in heroin-dependent volunteers.
2003-11
[Combined use of intrathecal morphine and diclofenac suppository for postoperative analgesia after caesarean section].
2003-10
The use of long-acting opioids in chronic pain management.
2003-09
Oral vs. i.v. hydromorphone. Add a measure of caution.
2003-09
Comparison of morphine and hydromorphone analysis on reversed phase columns with different diameters.
2003-08-08
Calculating opioid dose conversions #36.
2003-08
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).
2003-08
Is the analgesic effect of systemic lidocaine mediated through opioid receptors?
2003-08
[Pain therapy with semisynthetic opioids. Patients have opioid-type side effects more rarely].
2003-07-10
Long-term outcomes during treatment of chronic pain with intrathecal clonidine or clonidine/opioid combinations.
2003-07
Pharmacokinetics and bioavailability of single-dose intranasal hydromorphone hydrochloride in healthy volunteers.
2003-07
Management of postoperative pain after T6 corpectomy: use of epidural bupivacaine and sufentanil--a case report.
2003-06
Oral oxycodone: new preparation. No better than oral morphine.
2003-06
Antinociceptive effects of hydromorphone, bupivacaine and biphalin released from PLGA polymer after intrathecal implantation in rats.
2003-05
Opioid equianalgesic conversion: the right dose.
2003-04-15
Morphine and hydromorphone for postoperative analgesia: focus on safety.
2003-04
Embolized crospovidone (poly[N-vinyl-2-pyrrolidone]) in the lungs of intravenous drug users.
2003-04
Pharmacokinetic drug interactions of morphine, codeine, and their derivatives: theory and clinical reality, part I.
2003-03-06
Using saccadic eye movements as objective measures of tolerance in methadone dependent individuals during the hydromorphone challenge test.
2003-03
Changes in intraocular pressure and pupil size following intramuscular administration of hydromorphone hydrochloride and acepromazine in clinically normal dogs.
2003-03
Opioid ligands having delayed long-term antagonist activity: potential pharmacotherapies for opioid abuse.
2003-03
Quantification of the O- and N-demethylated metabolites of hydrocodone and oxycodone in human liver microsomes using liquid chromatography with ultraviolet absorbance detection.
2003-02-25
Postoperative hypoxemia and hypercarbia in healthy dogs undergoing routine ovariohysterectomy or castration and receiving butorphanol or hydromorphone for analgesia.
2003-02-01
A systematic review of hydromorphone in acute and chronic pain.
2003-02
Hydromorphone transfer into breast milk after intranasal administration.
2003-02
Activity of opioid ligands in cells expressing cloned mu opioid receptors.
2003-01-04
Catheter-associated masses in patients receiving intrathecal analgesic therapy.
2003-01
In vivo pain relief effectiveness of an analgesic-anesthetic carrying biodegradable controlled release rod systems.
2003
Envenomation by the Mexican beaded lizard: a case report.
2003
Postoperative analgesia and sedation in the adult intensive care unit: a guide to drug selection.
2003
Screening extemporaneously compounded intraspinal injections with the bacterial endotoxins test.
2002-12-15
Role of urine toxicology testing in the management of chronic opioid therapy.
2002-12-14
Clinical pharmacology of opioids for pain.
2002-12-14
Epidural and intrathecal analgesia for cancer pain.
2002-12
Activation profiles of opioid ligands in HEK cells expressing delta opioid receptors.
2002-11-18
Opioid rotation in the treatment of joint pain. A review of 67 cases.
2002-10
Simultaneous quantitation of opioids in blood by GC-EI-MS analysis following deproteination, detautomerization of keto analytes, solid-phase extraction, and trimethylsilyl derivatization.
2002-10
A field evaluation of five on-site drug-testing devices.
2002-10
Detection of cocaine analytes and opiates in nails from postmortem cases.
2002-10
Input characteristics and bioavailability after administration of immediate and a new extended-release formulation of hydromorphone in healthy volunteers.
2002-10
Fentanyl-associated syndrome of inappropriate antidiuretic hormone secretion.
2002-09
A convenient synthesis of delta(7,8)-morphinan-6-one and its direct oxidation to 14-hydroxy-delta(7,8)-morphinan-6-one.
2002-08-05
The addition of hydromorphone to epidural fentanyl does not affect analgesia in early labour.
2002-06-18
The use of methadone for cancer pain.
2002-06
Pain management for joint arthroplasty: preemptive analgesia.
2002-06
Postthoracotomy pain management.
2002-05
New directions in pain management.
2002-02
Clonazepam treatment of myoclonic contractions associated with high-dose opioids: case report.
1992-05
Survey of pain management therapy provided for children with sickle cell disease.
1992-04
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. Intravenous Administration: The initial starting dose is 0.2 to 1 mg every 2 to 3 hours. Intravenous administration should be given slowly, over at least 2 to 3 minutes, depending on the dose. The initial dose should be reduced in the elderly or debilitated and may be lowered to 0.2 mg.
Route of Administration: Other
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Wed Apr 02 09:52:43 GMT 2025
Edited
by admin
on Wed Apr 02 09:52:43 GMT 2025
Record UNII
Q812464R06
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
HYDROMORPHONE
HSDB   INN   MI   VANDF   WHO-DD  
INN  
Official Name English
N02AA03
Preferred Name English
HYDROMORPHON
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
Hydromorphone [WHO-DD]
Common Name English
HYDROCODONE HYDROGEN TARTRATE 2.5-HYDRATE IMPURITY K [EP IMPURITY]
Common Name English
DIMORPHONE
Common Name English
Classification Tree Code System Code
DEA NO. 9150
Created by admin on Wed Apr 02 09:52:43 GMT 2025 , Edited by admin on Wed Apr 02 09:52:43 GMT 2025
WHO-VATC QN02AA03
Created by admin on Wed Apr 02 09:52:43 GMT 2025 , Edited by admin on Wed Apr 02 09:52:43 GMT 2025
WHO-ATC N02AA03
Created by admin on Wed Apr 02 09:52:43 GMT 2025 , Edited by admin on Wed Apr 02 09:52:43 GMT 2025
WHO-VATC QN02AG04
Created by admin on Wed Apr 02 09:52:43 GMT 2025 , Edited by admin on Wed Apr 02 09:52:43 GMT 2025
NDF-RT N0000175684
Created by admin on Wed Apr 02 09:52:43 GMT 2025 , Edited by admin on Wed Apr 02 09:52:43 GMT 2025
NCI_THESAURUS C67413
Created by admin on Wed Apr 02 09:52:43 GMT 2025 , Edited by admin on Wed Apr 02 09:52:43 GMT 2025
LIVERTOX NBK548775
Created by admin on Wed Apr 02 09:52:43 GMT 2025 , Edited by admin on Wed Apr 02 09:52:43 GMT 2025
NDF-RT N0000175690
Created by admin on Wed Apr 02 09:52:43 GMT 2025 , Edited by admin on Wed Apr 02 09:52:43 GMT 2025
NCI_THESAURUS C1506
Created by admin on Wed Apr 02 09:52:43 GMT 2025 , Edited by admin on Wed Apr 02 09:52:43 GMT 2025
WHO-ATC N02AA53
Created by admin on Wed Apr 02 09:52:43 GMT 2025 , Edited by admin on Wed Apr 02 09:52:43 GMT 2025
WHO-ATC N02AG04
Created by admin on Wed Apr 02 09:52:43 GMT 2025 , Edited by admin on Wed Apr 02 09:52:43 GMT 2025
Code System Code Type Description
INN
1770
Created by admin on Wed Apr 02 09:52:43 GMT 2025 , Edited by admin on Wed Apr 02 09:52:43 GMT 2025
PRIMARY
ChEMBL
CHEMBL398707
Created by admin on Wed Apr 02 09:52:43 GMT 2025 , Edited by admin on Wed Apr 02 09:52:43 GMT 2025
PRIMARY
CAS
466-99-9
Created by admin on Wed Apr 02 09:52:43 GMT 2025 , Edited by admin on Wed Apr 02 09:52:43 GMT 2025
PRIMARY
ECHA (EC/EINECS)
207-383-5
Created by admin on Wed Apr 02 09:52:43 GMT 2025 , Edited by admin on Wed Apr 02 09:52:43 GMT 2025
PRIMARY
WIKIPEDIA
HYDROMORPHONE
Created by admin on Wed Apr 02 09:52:43 GMT 2025 , Edited by admin on Wed Apr 02 09:52:43 GMT 2025
PRIMARY
EVMPD
SUB08070MIG
Created by admin on Wed Apr 02 09:52:43 GMT 2025 , Edited by admin on Wed Apr 02 09:52:43 GMT 2025
PRIMARY
IUPHAR
7082
Created by admin on Wed Apr 02 09:52:43 GMT 2025 , Edited by admin on Wed Apr 02 09:52:43 GMT 2025
PRIMARY
MERCK INDEX
m6110
Created by admin on Wed Apr 02 09:52:43 GMT 2025 , Edited by admin on Wed Apr 02 09:52:43 GMT 2025
PRIMARY Merck Index
NSC
19046
Created by admin on Wed Apr 02 09:52:43 GMT 2025 , Edited by admin on Wed Apr 02 09:52:43 GMT 2025
PRIMARY
DRUG BANK
DB00327
Created by admin on Wed Apr 02 09:52:43 GMT 2025 , Edited by admin on Wed Apr 02 09:52:43 GMT 2025
PRIMARY
DAILYMED
Q812464R06
Created by admin on Wed Apr 02 09:52:43 GMT 2025 , Edited by admin on Wed Apr 02 09:52:43 GMT 2025
PRIMARY
HSDB
3341
Created by admin on Wed Apr 02 09:52:43 GMT 2025 , Edited by admin on Wed Apr 02 09:52:43 GMT 2025
PRIMARY
MESH
D004091
Created by admin on Wed Apr 02 09:52:43 GMT 2025 , Edited by admin on Wed Apr 02 09:52:43 GMT 2025
PRIMARY
LACTMED
Hydromorphone
Created by admin on Wed Apr 02 09:52:43 GMT 2025 , Edited by admin on Wed Apr 02 09:52:43 GMT 2025
PRIMARY
PUBCHEM
5284570
Created by admin on Wed Apr 02 09:52:43 GMT 2025 , Edited by admin on Wed Apr 02 09:52:43 GMT 2025
PRIMARY
CHEBI
5790
Created by admin on Wed Apr 02 09:52:43 GMT 2025 , Edited by admin on Wed Apr 02 09:52:43 GMT 2025
PRIMARY
RXCUI
3423
Created by admin on Wed Apr 02 09:52:43 GMT 2025 , Edited by admin on Wed Apr 02 09:52:43 GMT 2025
PRIMARY RxNorm
DRUG CENTRAL
1393
Created by admin on Wed Apr 02 09:52:43 GMT 2025 , Edited by admin on Wed Apr 02 09:52:43 GMT 2025
PRIMARY
FDA UNII
Q812464R06
Created by admin on Wed Apr 02 09:52:43 GMT 2025 , Edited by admin on Wed Apr 02 09:52:43 GMT 2025
PRIMARY
EPA CompTox
DTXSID8023133
Created by admin on Wed Apr 02 09:52:43 GMT 2025 , Edited by admin on Wed Apr 02 09:52:43 GMT 2025
PRIMARY
NCI_THESAURUS
C62034
Created by admin on Wed Apr 02 09:52:43 GMT 2025 , Edited by admin on Wed Apr 02 09:52:43 GMT 2025
PRIMARY
SMS_ID
100000090462
Created by admin on Wed Apr 02 09:52:43 GMT 2025 , Edited by admin on Wed Apr 02 09:52:43 GMT 2025
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)
SALT/SOLVATE -> PARENT
APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)
SALT/SOLVATE -> PARENT
APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)
Related Record Type Details
PARENT -> IMPURITY
Related Record Type Details
ACTIVE MOIETY