Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C17H21NO3.C6H3N3O7 |
| Molecular Weight | 516.4575 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 5 / 5 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OC1=C(C=C(C=C1[N+]([O-])=O)[N+]([O-])=O)[N+]([O-])=O.CN2CC[C@]34[C@H]5OC6=C(O)C=CC(C[C@@H]2[C@@H]3CC[C@@H]5O)=C46
InChI
InChIKey=RIEAKNQPZCQWTP-VYKNHSEDSA-N
InChI=1S/C17H21NO3.C6H3N3O7/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;10-6-4(8(13)14)1-3(7(11)12)2-5(6)9(15)16/h2,4,10-11,13,16,19-20H,3,5-8H2,1H3;1-2,10H/t10-,11+,13-,16-,17-;/m0./s1
| 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 | C6H3N3O7 |
| Molecular Weight | 229.1039 |
| 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).
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
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
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | dilaudid Approved UseDihydromorphine 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 Date1984 |
Overview
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
OverviewOther
| Other Inhibitor | Other Substrate | Other Inducer |
|---|---|---|
Drug as perpetrator
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| inconclusive [IC50 2.4733 uM] | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no |
Drug as victim
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| major | ||||
Page: 49 | 61 |
no |
Tox targets
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
PubMed
| Title | Date | PubMed |
|---|---|---|
| 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 |
|
| LC-MS-MS analysis of hydromorphone and hydromorphone metabolites with application to a pharmacokinetic study in the male Sprague-Dawley rat. | 2002 Feb |
|
| 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 |
|
| Capillary electrophoresis contributions to the hydromorphone metabolism in man. | 2006 Jun |
|
| Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method. | 2010 Dec |
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
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Edited
Mon Mar 31 23:08:18 GMT 2025
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Mon Mar 31 23:08:18 GMT 2025
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| Record UNII |
S6V722J7YS
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| Record Status |
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PARENT -> SALT/SOLVATE |
