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).
CNS Activity
Originator
Sources: https://patents.google.com/patent/DE365683C/en
Curator's Comment: now Abott Laboratories
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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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 |
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Sources: https://www.ncbi.nlm.nih.gov/pubmed/15178355 |
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 |
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Standard binding and functional assays related to medications development division testing for potential cocaine and opiate narcotic treatment medications. | 1998 Mar |
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LC-MS-MS analysis of hydromorphone and hydromorphone metabolites with application to a pharmacokinetic study in the male Sprague-Dawley rat. | 2002 Feb |
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The role of active metabolites in dihydrocodeine effects. | 2003 Mar |
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Pharmacological characterization of dihydromorphine, 6-acetyldihydromorphine and dihydroheroin analgesia and their differentiation from morphine. | 2004 May 25 |
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Identification and synthesis of norhydromorphone, and determination of antinociceptive activities in the rat formalin test. | 2004 Nov 12 |
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Capillary electrophoresis contributions to the hydromorphone metabolism in man. | 2006 Jun |
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[Symptomatic treatment of dyspnoea in patients receiving palliative care: nasal delivery of oxygen compared with opioid administration]. | 2007 Sep |
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Using molecular similarity to highlight the challenges of routine immunoassay-based drug of abuse/toxicology screening in emergency medicine. | 2009 Apr 28 |
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Acupuncture treatment for pain: systematic review of randomised clinical trials with acupuncture, placebo acupuncture, and no acupuncture groups. | 2009 Jan 27 |
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Recent advances in the use of opioids for cancer pain. | 2009 Sep 23 |
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Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method. | 2010 Dec |
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Endogenous morphine levels are increased in sepsis: a partial implication of neutrophils. | 2010 Jan 20 |
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The role of dihydrocodeine (DHC) metabolites in dihydrocodeine-related deaths. | 2010 Oct |
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In vitro and in vivo pharmacological profile of the 5-benzyl analogue of 14-methoxymetopon, a novel mu opioid analgesic with reduced propensity to alter motor function. | 2010 Sep 11 |
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12437765
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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admin
on
Edited
Sat Dec 16 02:10:13 GMT 2023
by
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on
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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Record Version |
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DEA NO. |
9145
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m4464
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DIHYDROMORPHINE
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TARGET -> AGONIST |
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SOLVATE->ANHYDROUS | |||
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PARENT -> DERIVATIVE |
DIHYDROMORPHINE (derivative of morphine) as per INCB
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SALT/SOLVATE -> PARENT |
APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)
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PARENT -> METABOLITE |
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URINE
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PARENT -> METABOLITE ACTIVE |
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USP
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