DIHYDROMORPHINE HYDROCHLORIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C17H21NO3.ClH
Molecular Weight	323.814
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of DIHYDROMORPHINE HYDROCHLORIDE

Structure Search

SMILES

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

InChI

InChIKey=DZGJPYLWWJSNCT-VYKNHSEDSA-N

InChI=1S/C17H21NO3.ClH/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;1H/t10-,11+,13-,16-,17-;/m0./s1

HIDE SMILES / InChI

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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

Description
Sources: https://www.drugbank.ca/drugs/DB01565 | https://www.ncbi.nlm.nih.gov/pubmed/15178355 | https://www.drugs.com/pro/hydromorphone.html

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

Approval Year

Targets

Primary Target	Pharmacology	Potency
Mu-type opioid receptor 61 Target ID: P35372\|\|\|G8XRH8\|\|\|Q5TDA1\|\|\|Q9UN57 Gene ID: 4988.0 Gene Symbol: OPRM1 Target Organism: Homo sapiens (Human) Sources: https://www.drugbank.ca/drugs/DB01565 \| https://www.ncbi.nlm.nih.gov/pubmed/15178355	Agonist 2678	0.23 nM [Ki]
Delta-type opioid receptor 45 Target ID: P41143 Gene ID: 4985.0 Gene Symbol: OPRD1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/15178355 \| https://www.drugbank.ca/drugs/DB01565	Agonist 2678
Kappa-type opioid receptor 60 Target ID: P41145 Gene ID: 4986.0 Gene Symbol: OPRK1 Target Organism: Homo sapiens (Human) Sources: https://www.drugbank.ca/drugs/DB01565 \| https://www.ncbi.nlm.nih.gov/pubmed/15178355	Agonist 2678	183.0 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pain 614 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15178355	Primary		Approved 8429	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 1984

PubMed

Title	Date	PubMed
Standard binding and functional assays related to medications development division testing for potential cocaine and opiate narcotic treatment medications.	1998 Mar	9686407
LC-MS-MS analysis of hydromorphone and hydromorphone metabolites with application to a pharmacokinetic study in the male Sprague-Dawley rat.	2002 Feb	11868970
Morphine 6 glucuronide stimulates nitric oxide release in mussel neural tissues: evidence for a morphine 6 glucuronide opiate receptor subtype.	2002 Mar	11964135
The role of active metabolites in dihydrocodeine effects.	2003 Mar	12665158
Pharmacological characterization of dihydromorphine, 6-acetyldihydromorphine and dihydroheroin analgesia and their differentiation from morphine.	2004 May 25	15178355
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method.	2010 Dec	21818443

Patents

Sample Use Guides

In Vivo Use Guide

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

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 04:18:48 GMT 2023` Edited by `admin` on `Sat Dec 16 04:18:48 GMT 2023`
Record UNII	3T8C8KE0AW
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

DIHYDROMORPHINE HYDROCHLORIDE

Common Name

English

MORPHINAN-3,6.ALPHA.-DIOL, 4,5.ALPHA.-EPOXY-17-METHYL-, HYDROCHLORIDE

Systematic Name

English

DIALUDID

Brand Name

English

NSC-404353

Code

English

MORPHINAN-3,6-DIOL, 4,5-EPOXY-17-METHYL-, HYDROCHLORIDE, (5.ALPHA.,6.ALPHA.)-

Systematic Name

English

DIHYDROMORPHINE HYDROCHLORIDE [MI]

Common Name

English

MORPHINE, DIHYDRO-, HYDROCHLORIDE

Common Name

English

Code System Code Type Description

MERCK INDEX

m4464