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Details

Stereochemistry ABSOLUTE
Molecular Formula C17H21NO3.H2O
Molecular Weight 305.3688
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DIHYDROMORPHINE MONOHYDRATE

SMILES

O.[H][C@@]12OC3=C4C(C[C@@]5([H])N(C)CC[C@@]14[C@@]5([H])CC[C@@H]2O)=CC=C3O

InChI

InChIKey=AEUDPNLYBQEXMH-VYKNHSEDSA-N
InChI=1S/C17H21NO3.H2O/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;/h2,4,10-11,13,16,19-20H,3,5-8H2,1H3;1H2/t10-,11+,13-,16-,17-;/m0./s1

HIDE SMILES / InChI

Molecular Formula C17H21NO3
Molecular Weight 287.3535
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Dihydromorphine is a semi-synthetic opioid derived from morphine. dihydromorphine is a moderately strong analgesic and is used clinically in the treatment of pain and is also the active metabolite of dihydrocodeine. Dihydromorphine acts as an agonist at the μ-opioid (mu), δ-opioid (delta) and κ-opioid (kappa) receptors. Dihydromorphone is approved for clinical use in the United States, Europe, and Japan; and sold under the brand name Dilaudid. Similar to morphine, and other morphine derivatives, hydromorphone has a high potential for addiction and abuse and is listed as a Schedule II drug in the United States Controlled Substances Act of 1970 (and similarly regulated in other countries).

Originator

Curator's Comment: now Abott Laboratories

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P35372|||G8XRH8|||Q5TDA1|||Q9UN57
Gene ID: 4988.0
Gene Symbol: OPRM1
Target Organism: Homo sapiens (Human)
0.23 nM [Ki]
Target ID: P41143
Gene ID: 4985.0
Gene Symbol: OPRD1
Target Organism: Homo sapiens (Human)
Target ID: P41145
Gene ID: 4986.0
Gene Symbol: OPRK1
Target Organism: Homo sapiens (Human)
183.0 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
dilaudid

Approved Use

Dihydromorphine is approved for the treatment of pain and to be administered as an injection, oral tablet or oral solution. The usual starting injection dose is 1-2 mg subcutaneously or intramuscularly every 4 to 6 hours as necessary for pain control. The usual adult oral dosage of DILAUDID ORAL LIQUID is one-half (2.5 mL) to two teaspoonfuls (10 mL) corresponding to 2.5 mg - 10 mg every 3 to 6 hours as directed by the clinical situation. The usual starting dose for DILAUDID tablets is 2 mg to 4 mg, orally, every 4 to 6 hours.

Launch Date

4.42627195E11
PubMed

PubMed

TitleDatePubMed
Evaluation of urinary dihydrocodeine excretion in human by gas chromatography-mass spectrometry.
2001 Mar 5
Affinities of dihydrocodeine and its metabolites to opioid receptors.
2002 Aug
Hydromorphone metabolites: isolation and identification from pooled urine samples of a cancer patient.
2002 May
The role of active metabolites in dihydrocodeine effects.
2003 Mar
Pharmacological characterization of dihydromorphine, 6-acetyldihydromorphine and dihydroheroin analgesia and their differentiation from morphine.
2004 May 25
Identification and synthesis of norhydromorphone, and determination of antinociceptive activities in the rat formalin test.
2004 Nov 12
Opiate receptor binding properties of morphine-, dihydromorphine-, and codeine 6-O-sulfate ester congeners.
2006 Aug 15
[Symptomatic treatment of dyspnoea in patients receiving palliative care: nasal delivery of oxygen compared with opioid administration].
2007 Sep
Method for quantification of opioids and their metabolites in autopsy blood by liquid chromatography-tandem mass spectrometry.
2007 Sep
Using molecular similarity to highlight the challenges of routine immunoassay-based drug of abuse/toxicology screening in emergency medicine.
2009 Apr 28
Acupuncture treatment for pain: systematic review of randomised clinical trials with acupuncture, placebo acupuncture, and no acupuncture groups.
2009 Jan 27
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method.
2010 Dec
Endogenous morphine levels are increased in sepsis: a partial implication of neutrophils.
2010 Jan 20
The role of dihydrocodeine (DHC) metabolites in dihydrocodeine-related deaths.
2010 Oct
Patents

Sample Use Guides

Dihydromorphine is approved for the treatment of pain and to be administered as an injection, oral tablet or oral solution. The usual starting injection dose is 1-2 mg subcutaneously or intramuscularly every 4 to 6 hours as necessary for pain control. The usual adult oral dosage of DILAUDID ORAL LIQUID is one-half (2.5 mL) to two teaspoonfuls (10 mL) corresponding to 2.5 mg - 10 mg every 3 to 6 hours as directed by the clinical situation. The usual starting dose for DILAUDID tablets is 2 mg to 4 mg, orally, every 4 to 6 hours.
Route of Administration: Other
Human Embryonic Kidney 293 cells (HEK293) were transfected with mouse delta-opioid receptor and maintained in D-MEM/F-12 medium, supplemented with 10% (v/v)fetal calf serum (FCS), and 200 micro-g/mL G-418 in an atmosphere of 5% CO2 at 37 deg-C. Cells were re-plated once per week. Agonistic activity of opioid ligands was assessed by measuring the inhibitory effect of the ligands on forskolin-stimulated cAMP accumulation. Hydromorphone demonstrated an IC50 of 54 nM for the activation of HEK-delta cells.
Substance Class Chemical
Created
by admin
on Sat Dec 16 04:00:04 UTC 2023
Edited
by admin
on Sat Dec 16 04:00:04 UTC 2023
Record UNII
NU189G5QU4
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DIHYDROMORPHINE MONOHYDRATE
MI  
Common Name English
DIHYDROMORPHINE MONOHYDRATE [MI]
Common Name English
MORPHINAN-3,6-DIOL, 4,5-EPOXY-17-METHYL-, MONOHYDRATE, (5.ALPHA.,6.ALPHA.)-
Systematic Name English
Code System Code Type Description
PUBCHEM
68487363
Created by admin on Sat Dec 16 04:00:04 UTC 2023 , Edited by admin on Sat Dec 16 04:00:04 UTC 2023
PRIMARY
MERCK INDEX
m4464
Created by admin on Sat Dec 16 04:00:04 UTC 2023 , Edited by admin on Sat Dec 16 04:00:04 UTC 2023
PRIMARY Merck Index
FDA UNII
NU189G5QU4
Created by admin on Sat Dec 16 04:00:04 UTC 2023 , Edited by admin on Sat Dec 16 04:00:04 UTC 2023
PRIMARY
CAS
65943-40-0
Created by admin on Sat Dec 16 04:00:04 UTC 2023 , Edited by admin on Sat Dec 16 04:00:04 UTC 2023
PRIMARY
EPA CompTox
DTXSID60216165
Created by admin on Sat Dec 16 04:00:04 UTC 2023 , Edited by admin on Sat Dec 16 04:00:04 UTC 2023
PRIMARY
Related Record Type Details
ANHYDROUS->SOLVATE