Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C17H21NO3 |
| Molecular Weight | 287.3535 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 5 / 5 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]12OC3=C(O)C=CC4=C3[C@@]15CCN(C)[C@H](C4)[C@]5([H])CC[C@@H]2O
InChI
InChIKey=IJVCSMSMFSCRME-KBQPJGBKSA-N
InChI=1S/C17H21NO3/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/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 |
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 |
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 |
|
| Hydromorphone metabolites: isolation and identification from pooled urine samples of a cancer patient. | 2002 May |
|
| Practical and high-yield syntheses of dihydromorphine from tetrahydrothebaine and efficient syntheses of (8S)-8-bromomorphide. | 2003 Mar 7 |
|
| Opiate receptor binding properties of morphine-, dihydromorphine-, and codeine 6-O-sulfate ester congeners. | 2006 Aug 15 |
|
| 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 |
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
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Sat Dec 16 02:10:13 GMT 2023
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| Record UNII |
C3S5FRP6JW
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| Record Status |
Validated (UNII)
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9145
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m4464
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DIHYDROMORPHINE
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100000079222
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5359421
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URINE
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