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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

[H][C@]12CCC(=O)[C@@H]3OC4=C5C(C[C@H]1N(C)CC[C@@]235)=CC=C4O

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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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.

CNS Activity

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
279.0 nM [EC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
DILAUDID-HP

Cmax

ValueDoseCo-administeredAnalytePopulation
5.5 ng/mL
8 mg single, oral
HYDROMORPHONE HYDROCHLORIDE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
23.7 ng × h/mL
8 mg single, oral
HYDROMORPHONE HYDROCHLORIDE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
2.6 h
8 mg single, oral
HYDROMORPHONE HYDROCHLORIDE plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
81%
8 mg single, oral
HYDROMORPHONE HYDROCHLORIDE plasma
Homo sapiens

Doses

AEs

OverviewOther

Other InhibitorOther SubstrateOther Inducer




Drug as perpetrator​

Drug as victim

Sourcing

PubMed

Sample Use Guides

In Vivo Use Guide
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
Record UNII
Q812464R06
Record Status Validated (UNII)
Record Version