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

Details

Stereochemistry ABSOLUTE
Molecular Formula C17H19NO3.ClH
Molecular Weight 321.799
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of HYDROMORPHONE HYDROCHLORIDE

SMILES

Cl.[H][C@@]12OC3=C4C(C[C@H]5N(C)CC[C@@]14[C@@]5([H])CCC2=O)=CC=C3O

InChI

InChIKey=XHILEZUETWRSHC-NRGUFEMZSA-N
InChI=1S/C17H19NO3.ClH/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;1H/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

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

4.42627195E11
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: Page: p.274
unhealthy, 27
n = 1
Health Status: unhealthy
Condition: Pain
Age Group: 27
Sex: F
Population Size: 1
Sources: Page: p.274
Disc. AE: Sleepiness, Nausea...
AEs leading to
discontinuation/dose reduction:
Sleepiness
Nausea
Sources: Page: p.274
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: Page: p.378
unhealthy, 40
n = 1
Health Status: unhealthy
Condition: Pain
Age Group: 40
Sex: M
Population Size: 1
Sources: Page: p.378
Disc. AE: Respiratory arrest...
AEs leading to
discontinuation/dose reduction:
Respiratory arrest (grade 5)
Sources: Page: p.378
4 mg 4 times / day multiple, oral (max)
Recommended
Dose: 4 mg, 4 times / day
Route: oral
Route: multiple
Dose: 4 mg, 4 times / day
Sources: Page: p.545
unhealthy, 67.7
n = 88
Health Status: unhealthy
Condition: Pain
Age Group: 67.7
Sex: M+F
Population Size: 88
Sources: Page: p.545
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: Page: p.545
10 mg single, intravenous
Overdose
Dose: 10 mg
Route: intravenous
Route: single
Dose: 10 mg
Sources: Page: p.378
unhealthy
n = 1
Health Status: unhealthy
Condition: Pain
Population Size: 1
Sources: Page: p.378
Disc. AE: Cardio-respiratory arrest...
AEs leading to
discontinuation/dose reduction:
Cardio-respiratory arrest (grade 5)
Sources: Page: p.378
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: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Pain
Sources: Page: p.1
Disc. AE: Respiratory depression...
AEs leading to
discontinuation/dose reduction:
Respiratory depression
Sources: Page: p.1
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: Page: p.1
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: Page: p.1
AEs

AEs

AESignificanceDosePopulation
Nausea Disc. AE
540 mg single, intrathecal
Overdose
Dose: 540 mg
Route: intrathecal
Route: single
Dose: 540 mg
Sources: Page: p.274
unhealthy, 27
n = 1
Health Status: unhealthy
Condition: Pain
Age Group: 27
Sex: F
Population Size: 1
Sources: Page: p.274
Sleepiness Disc. AE
540 mg single, intrathecal
Overdose
Dose: 540 mg
Route: intrathecal
Route: single
Dose: 540 mg
Sources: Page: p.274
unhealthy, 27
n = 1
Health Status: unhealthy
Condition: Pain
Age Group: 27
Sex: F
Population Size: 1
Sources: Page: p.274
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: Page: p.378
unhealthy, 40
n = 1
Health Status: unhealthy
Condition: Pain
Age Group: 40
Sex: M
Population Size: 1
Sources: Page: p.378
Aspiration pneumonia grade 5, 1.14%
Disc. AE
4 mg 4 times / day multiple, oral (max)
Recommended
Dose: 4 mg, 4 times / day
Route: oral
Route: multiple
Dose: 4 mg, 4 times / day
Sources: Page: p.545
unhealthy, 67.7
n = 88
Health Status: unhealthy
Condition: Pain
Age Group: 67.7
Sex: M+F
Population Size: 88
Sources: Page: p.545
Nausea and vomiting serious, 1.14%
Disc. AE
4 mg 4 times / day multiple, oral (max)
Recommended
Dose: 4 mg, 4 times / day
Route: oral
Route: multiple
Dose: 4 mg, 4 times / day
Sources: Page: p.545
unhealthy, 67.7
n = 88
Health Status: unhealthy
Condition: Pain
Age Group: 67.7
Sex: M+F
Population Size: 88
Sources: Page: p.545
Somnolence serious, 1.14%
Disc. AE
4 mg 4 times / day multiple, oral (max)
Recommended
Dose: 4 mg, 4 times / day
Route: oral
Route: multiple
Dose: 4 mg, 4 times / day
Sources: Page: p.545
unhealthy, 67.7
n = 88
Health Status: unhealthy
Condition: Pain
Age Group: 67.7
Sex: M+F
Population Size: 88
Sources: Page: p.545
Toxic skin eruption serious, 1.14%
Disc. AE
4 mg 4 times / day multiple, oral (max)
Recommended
Dose: 4 mg, 4 times / day
Route: oral
Route: multiple
Dose: 4 mg, 4 times / day
Sources: Page: p.545
unhealthy, 67.7
n = 88
Health Status: unhealthy
Condition: Pain
Age Group: 67.7
Sex: M+F
Population Size: 88
Sources: Page: p.545
Cardio-respiratory arrest grade 5
Disc. AE
10 mg single, intravenous
Overdose
Dose: 10 mg
Route: intravenous
Route: single
Dose: 10 mg
Sources: Page: p.378
unhealthy
n = 1
Health Status: unhealthy
Condition: Pain
Population Size: 1
Sources: Page: p.378
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: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Pain
Sources: Page: p.1
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: Page: p.1
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: Page: p.1
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: Page: p.1
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: Page: p.1
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: Page: p.1
unhealthy
PubMed

PubMed

TitleDatePubMed
Pharmacokinetics of oral immediate-release hydromorphone (Dilaudid IR) in subjects with renal impairment.
2001
Effect of food on the pharmacokinetics of oral immediate-release hydromorphone (Dilaudid IR).
2001
A dual epidural catheter technique to provide analgesia following posterior spinal fusion for scoliosis in children and adolescents.
2001 Mar
Morphine and alternative opioids in cancer pain: the EAPC recommendations.
2001 Mar 2
The role of the brain reward system in depression.
2001 May
Intravenous methadone in the management of chronic cancer pain: safe and effective starting doses when substituting methadone for fentanyl.
2001 Oct 1
Enadoline, a selective kappa opioid agonist: comparison with butorphanol and hydromorphone in humans.
2001 Sep
Stability, compatibility, and safety of intrathecal bupivacaine administered chronically via an implantable delivery system.
2001 Sep
Hydromorphone for acute and chronic pain.
2002
The simultaneous determination of codeine, morphine, hydrocodone, hydromorphone, 6-acetylmorphine, and oxycodone in hair and oral fluid.
2002 Apr
Screening extemporaneously compounded intraspinal injections with the bacterial endotoxins test.
2002 Dec 15
[New Level III opioids of the World Health Organization].
2002 Jan
Synthesis and biological activity of 8beta-substituted hydrocodone indole and hydromorphone indole derivatives.
2002 Jan 21
The use of methadone for cancer pain.
2002 Jun
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
Activation profiles of opioid ligands in HEK cells expressing delta opioid receptors.
2002 Nov 18
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
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
Activity of opioid ligands in cells expressing cloned mu opioid receptors.
2003 Jan 4
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
Oral oxycodone: new preparation. No better than oral morphine.
2003 Jun
Opioid ligands having delayed long-term antagonist activity: potential pharmacotherapies for opioid abuse.
2003 Mar
Antinociceptive effects of hydromorphone, bupivacaine and biphalin released from PLGA polymer after intrathecal implantation in rats.
2003 May
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
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. 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 Fri Dec 15 15:00:27 UTC 2023
Edited
by admin
on Fri Dec 15 15:00:27 UTC 2023
Record UNII
L960UP2KRW
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
HYDROMORPHONE HYDROCHLORIDE
EP   MART.   MI   ORANGE BOOK   USP   VANDF   WHO-DD  
Common Name English
HYDROMORPHONE HYDROCHLORIDE CII
USP-RS  
Common Name English
4,5α-Epoxy-3-hydroxy-17-methylmorphinan-6-one hydrochloride
Systematic Name English
HYDROMORPHONE HYDROCHLORIDE [EP MONOGRAPH]
Common Name English
DIHYDROMORPHINONE HYDROCHLORIDE
Common Name English
Hydromorphone hydrochloride [WHO-DD]
Common Name English
HYDROMORPHONE HYDROCHLORIDE CII [USP-RS]
Common Name English
HYDROMORPHONE HYDROCHLORIDE [MART.]
Common Name English
HYDROMORPHONE HYDROCHLORIDE [JAN]
Common Name English
HYDROMORPHONE HYDROCHLORIDE [ORANGE BOOK]
Common Name English
HYDROMORPHONE HYDROCHLORIDE [USP MONOGRAPH]
Common Name English
HYDROMORPHONE HYDROCHLORIDE [VANDF]
Common Name English
EXALGO
Brand Name English
PALLADONE
Brand Name English
NSC-117862
Code English
DILAUDID
Brand Name English
HYDROMORPHONE HYDROCHLORIDE [MI]
Common Name English
MORPHINAN-6-ONE, 4,5-EPOXY-3-HYDROXY-17-METHYL-, HYDROCHLORIDE, (5.ALPHA.)-
Systematic Name English
HYDROMORPHONE HCL
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 499415
Created by admin on Fri Dec 15 15:00:27 UTC 2023 , Edited by admin on Fri Dec 15 15:00:27 UTC 2023
NCI_THESAURUS C67413
Created by admin on Fri Dec 15 15:00:27 UTC 2023 , Edited by admin on Fri Dec 15 15:00:27 UTC 2023
NCI_THESAURUS C1506
Created by admin on Fri Dec 15 15:00:27 UTC 2023 , Edited by admin on Fri Dec 15 15:00:27 UTC 2023
Code System Code Type Description
NCI_THESAURUS
C436
Created by admin on Fri Dec 15 15:00:27 UTC 2023 , Edited by admin on Fri Dec 15 15:00:27 UTC 2023
PRIMARY
ECHA (EC/EINECS)
200-762-6
Created by admin on Fri Dec 15 15:00:27 UTC 2023 , Edited by admin on Fri Dec 15 15:00:27 UTC 2023
PRIMARY
ChEMBL
CHEMBL398707
Created by admin on Fri Dec 15 15:00:27 UTC 2023 , Edited by admin on Fri Dec 15 15:00:27 UTC 2023
PRIMARY
FDA UNII
L960UP2KRW
Created by admin on Fri Dec 15 15:00:27 UTC 2023 , Edited by admin on Fri Dec 15 15:00:27 UTC 2023
PRIMARY
NSC
117862
Created by admin on Fri Dec 15 15:00:27 UTC 2023 , Edited by admin on Fri Dec 15 15:00:27 UTC 2023
PRIMARY
MERCK INDEX
m6110
Created by admin on Fri Dec 15 15:00:27 UTC 2023 , Edited by admin on Fri Dec 15 15:00:27 UTC 2023
PRIMARY Merck Index
EVMPD
SUB02573MIG
Created by admin on Fri Dec 15 15:00:27 UTC 2023 , Edited by admin on Fri Dec 15 15:00:27 UTC 2023
PRIMARY
RXCUI
203177
Created by admin on Fri Dec 15 15:00:27 UTC 2023 , Edited by admin on Fri Dec 15 15:00:27 UTC 2023
PRIMARY RxNorm
SMS_ID
100000090577
Created by admin on Fri Dec 15 15:00:27 UTC 2023 , Edited by admin on Fri Dec 15 15:00:27 UTC 2023
PRIMARY
RS_ITEM_NUM
1323000
Created by admin on Fri Dec 15 15:00:27 UTC 2023 , Edited by admin on Fri Dec 15 15:00:27 UTC 2023
PRIMARY
PUBCHEM
5462347
Created by admin on Fri Dec 15 15:00:27 UTC 2023 , Edited by admin on Fri Dec 15 15:00:27 UTC 2023
PRIMARY
DAILYMED
L960UP2KRW
Created by admin on Fri Dec 15 15:00:27 UTC 2023 , Edited by admin on Fri Dec 15 15:00:27 UTC 2023
PRIMARY
CAS
71-68-1
Created by admin on Fri Dec 15 15:00:27 UTC 2023 , Edited by admin on Fri Dec 15 15:00:27 UTC 2023
PRIMARY
CHEBI
5791
Created by admin on Fri Dec 15 15:00:27 UTC 2023 , Edited by admin on Fri Dec 15 15:00:27 UTC 2023
PRIMARY
DRUG BANK
DBSALT000444
Created by admin on Fri Dec 15 15:00:27 UTC 2023 , Edited by admin on Fri Dec 15 15:00:27 UTC 2023
PRIMARY
EPA CompTox
DTXSID90991291
Created by admin on Fri Dec 15 15:00:27 UTC 2023 , Edited by admin on Fri Dec 15 15:00:27 UTC 2023
PRIMARY
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