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Identification
NameDihydromorphine
Accession NumberDB01565
Typesmall molecule
Groupsexperimental, illicit
Description

A semisynthetic analgesic used in the study of narcotic receptors. It has abuse potential. [PubChem]

Structure
Thumb
SynonymsNot Available
SaltsNot Available
Brand namesNot Available
Brand mixturesNot Available
CategoriesNot Available
CAS number509-60-4
WeightAverage: 287.3535
Monoisotopic: 287.152143543
Chemical FormulaC17H21NO3
InChI KeyIJVCSMSMFSCRME-KBQPJGBKSA-N
InChI
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
IUPAC Name
(1S,5R,13R,14S,17R)-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0^{1,13}.0^{5,17}.0^{7,18}]octadeca-7(18),8,10-triene-10,14-diol
SMILES
[H][C@@]12OC3=C(O)C=CC4=C3[C@@]11CCN(C)[C@]([H])(C4)[C@]1([H])CC[C@@H]2O
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassAlkaloids and Derivatives
ClassMorphinans
SubclassNot Available
Direct parentMorphinans
Alternative parentsBenzylisoquinolines; Phenanthrenes and Derivatives; Tetralins; Benzofurans; Phenols and Derivatives; Alkyl Aryl Ethers; Cyclohexanols; Piperidines; Tertiary Amines; Cyclic Alcohols and Derivatives; Polyamines; Enols
Substituentsphenanthrene; tetralin; benzofuran; phenol derivative; cyclohexanol; alkyl aryl ether; benzene; piperidine; cyclic alcohol; tertiary amine; secondary alcohol; enol; ether; polyamine; amine; organonitrogen compound; alcohol
Classification descriptionThis compound belongs to the morphinans. These are polycyclic compounds with a four-ring skeleton with three condensed six-member rings forming a partially hydrogenated phenanthrene moiety, one of which is aromatic while the two others are alicyclic.
Pharmacology
IndicationDihydromorphine is an opioid analgesic used for moderate to severe pain relief.
PharmacodynamicsNot Available
Mechanism of actionNot Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.995
Blood Brain Barrier + 0.985
Caco-2 permeable + 0.8356
P-glycoprotein substrate Substrate 0.8896
P-glycoprotein inhibitor I Non-inhibitor 0.8653
P-glycoprotein inhibitor II Non-inhibitor 0.9868
Renal organic cation transporter Inhibitor 0.5516
CYP450 2C9 substrate Non-substrate 0.8115
CYP450 2D6 substrate Substrate 0.8647
CYP450 3A4 substrate Substrate 0.7582
CYP450 1A2 substrate Non-inhibitor 0.797
CYP450 2C9 substrate Non-inhibitor 0.9309
CYP450 2D6 substrate Non-inhibitor 0.617
CYP450 2C19 substrate Non-inhibitor 0.7678
CYP450 3A4 substrate Non-inhibitor 0.8793
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9646
Ames test Non AMES toxic 0.7901
Carcinogenicity Non-carcinogens 0.9598
Biodegradation Not ready biodegradable 0.9846
Rat acute toxicity 2.8928 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.8927
hERG inhibition (predictor II) Non-inhibitor 0.8414
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point157 dec °CPhysProp
Predicted Properties
PropertyValueSource
water solubility1.82e+00 g/lALOGPS
logP1.26ALOGPS
logP1.08ChemAxon
logS-2.2ALOGPS
pKa (strongest acidic)10.29ChemAxon
pKa (strongest basic)9.24ChemAxon
physiological charge1ChemAxon
hydrogen acceptor count4ChemAxon
hydrogen donor count2ChemAxon
polar surface area52.93ChemAxon
rotatable bond count0ChemAxon
refractivity79.16ChemAxon
polarizability30.66ChemAxon
number of rings5ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterYesChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis Reference

Herbert Merz, Ingrid Wiedemann, Helmut Ensinger, Klaus Stockhaus, Matthias Grauert, “14-hydroxy-N-(2-methoxyethyl)-7,8-dihydromorphine and -norisomorphine, processes for the preparation thereof and the use thereof as pharmaceutical compositions.” U.S. Patent US5240933, issued August 31, 1993.

US5240933
General ReferenceNot Available
External Links
ResourceLink
KEGG CompoundC11782
PubChem Compound5359421
PubChem Substance46506587
ChemSpider4514282
WikipediaDihydromorphine
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Mu-type opioid receptor

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Mu-type opioid receptor P35372 Details

References:

  1. Crooks PA, Kottayil SG, Al-Ghananeem AM, Byrn SR, Butterfield DA: Opiate receptor binding properties of morphine-, dihydromorphine-, and codeine 6-O-sulfate ester congeners. Bioorg Med Chem Lett. 2006 Aug 15;16(16):4291-5. Epub 2006 Jun 13. Pubmed
  2. Dietis N, Guerrini R, Calo G, Salvadori S, Rowbotham DJ, Lambert DG: Simultaneous targeting of multiple opioid receptors: a strategy to improve side-effect profile. Br J Anaesth. 2009 Jul;103(1):38-49. Epub 2009 May 27. Pubmed
  3. Gilbert AK, Hosztafi S, Mahurter L, Pasternak GW: Pharmacological characterization of dihydromorphine, 6-acetyldihydromorphine and dihydroheroin analgesia and their differentiation from morphine. Eur J Pharmacol. 2004 May 25;492(2-3):123-30. Pubmed

2. Delta-type opioid receptor

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: agonist

Components

Name UniProt ID Details
Delta-type opioid receptor P41143 Details

References:

  1. Crooks PA, Kottayil SG, Al-Ghananeem AM, Byrn SR, Butterfield DA: Opiate receptor binding properties of morphine-, dihydromorphine-, and codeine 6-O-sulfate ester congeners. Bioorg Med Chem Lett. 2006 Aug 15;16(16):4291-5. Epub 2006 Jun 13. Pubmed
  2. Dietis N, Guerrini R, Calo G, Salvadori S, Rowbotham DJ, Lambert DG: Simultaneous targeting of multiple opioid receptors: a strategy to improve side-effect profile. Br J Anaesth. 2009 Jul;103(1):38-49. Epub 2009 May 27. Pubmed
  3. Gilbert AK, Hosztafi S, Mahurter L, Pasternak GW: Pharmacological characterization of dihydromorphine, 6-acetyldihydromorphine and dihydroheroin analgesia and their differentiation from morphine. Eur J Pharmacol. 2004 May 25;492(2-3):123-30. Pubmed

3. Kappa-type opioid receptor

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: agonist

Components

Name UniProt ID Details
Kappa-type opioid receptor P41145 Details

References:

  1. Crooks PA, Kottayil SG, Al-Ghananeem AM, Byrn SR, Butterfield DA: Opiate receptor binding properties of morphine-, dihydromorphine-, and codeine 6-O-sulfate ester congeners. Bioorg Med Chem Lett. 2006 Aug 15;16(16):4291-5. Epub 2006 Jun 13. Pubmed
  2. Dietis N, Guerrini R, Calo G, Salvadori S, Rowbotham DJ, Lambert DG: Simultaneous targeting of multiple opioid receptors: a strategy to improve side-effect profile. Br J Anaesth. 2009 Jul;103(1):38-49. Epub 2009 May 27. Pubmed
  3. Gilbert AK, Hosztafi S, Mahurter L, Pasternak GW: Pharmacological characterization of dihydromorphine, 6-acetyldihydromorphine and dihydroheroin analgesia and their differentiation from morphine. Eur J Pharmacol. 2004 May 25;492(2-3):123-30. Pubmed

4. E3 ubiquitin-protein ligase TRIM13

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: agonist

Components

Name UniProt ID Details
E3 ubiquitin-protein ligase TRIM13 O60858 Details

References:

  1. Liebmann C, Schnittler M, Hartrodt B, Born I, Neubert K: Structure-activity studies of novel casomorphin analogues: binding profiles towards mu 1-, mu 2- and delta -opioid receptors. Pharmazie. 1991 May;46(5):345-8. Pubmed
  2. Maneckjee R, Archer S, Zukin RS: Characterization of a polyclonal antibody to the mu opioid receptor. J Neuroimmunol. 1988 Feb;17(3):199-208. Pubmed
  3. Ishizuka Y, Oka T: Relation of diltiazem binding sites to opioid receptor subtypes in the guinea-pig brain. Tokai J Exp Clin Med. 1987 Mar;12(1):11-7. Pubmed
  4. Koman A, Kolb VM, Terenius L: A naloxone-steroid hybrid azine with selective and long-acting opioid antagonism at delta receptors in vitro. Pharm Res. 1987 Apr;4(2):147-9. Pubmed
  5. Ho CL, Hammonds RG Jr, Li CH: Opiate receptor binding profile in the rabbit cerebellum and brain membranes. Biochem Pharmacol. 1985 Apr 1;34(7):925-31. Pubmed

5. Pro-opiomelanocortin

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: agonist

Components

Name UniProt ID Details
Pro-opiomelanocortin P01189 Details

References:

  1. Somoza E: Influence of neuroleptics on the binding of met-enkephalin, morphine and dihydromorphine to synaptosome-enriched fractions of rat brain. Neuropharmacology. 1978 Aug;17(8):577-81. Pubmed
  2. Johnson N, Houghten R, Pasternak GW: Binding of 3H-beta-endorphin in rat brain. Life Sci. 1982 Sep 20-27;31(12-13):1381-4. Pubmed

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Drug created on July 31, 2007 07:10 / Updated on September 16, 2013 17:15