Dihydrocodeine

Identification

Summary

Dihydrocodeine is an opioid analgesic agent used for the management of pain severe enough to require an opioid analgesic and for which alternative treatments are inadequate.

Brand Names
Dvorah, Trezix
Generic Name
Dihydrocodeine
DrugBank Accession Number
DB01551
Background

Dihydrocodeine is an opioid analgesic used as an alternative or adjunct to codeine to treat moderate to severe pain, severe dyspnea, and cough.

It is semi-synthetic, and was developed in Germany in 1908 during an international search to find a more effective antitussive agent to help reduce the spread of airborne infectious diseases such as tuburculosis. It was marketed in 1911.

Type
Small Molecule
Groups
Approved, Illicit
Structure
Weight
Average: 301.3801
Monoisotopic: 301.167793607
Chemical Formula
C18H23NO3
Synonyms
  • DHC
  • Dihydrocodeine
External IDs
  • IDS-ND-008(SECT.2)
  • NSC-231319

Pharmacology

Indication

Dihydrocodeine is used for the treatment of moderate to severe pain, including post-operative and dental pain [2]. It can also be used to treat chronic pain [1], breathlessness and coughing.

In heroin addicts, dihydrocodeine has been used as a substitute drug, in doses up to 2500mg/day to treat addiction. [http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2014322/]

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Used in combination to treatPainCombination Product in combination with: Caffeine (DB00201), Acetylsalicylic acid (DB00945)•••••••••••••••••••
Used in combination to manageSevere painCombination Product in combination with: Caffeine (DB00201), Acetaminophen (DB00316)••••••••••••
Used in combination to manageModerate painCombination Product in combination with: Caffeine (DB00201), Acetaminophen (DB00316)••••••••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

Possible opioid related side effects include, but are not limited to, drowsiness, nausea, headache, dry mouth, constipation, difficulty passing urine, and mild euphoria.

Mechanism of action

Dihydrocodeine is metabolized to dihydromorphine -- a highly active metabolite with a high affinity for mu opioid receptors. [3]

Absorption

Bioavailability is low (approximately 20%) if administered orally. This may be due to poor gastrointestinal absorption. It is also likely due to pre-systemic metabolism by the liver and intestinal wall. [2]

The AUCs after oral and intravenous administration are similar (3203ug/l/h and 3401ug/l/h, respectively). [2]

Time to peak values are 1.6 and 1.8hours for a 30mg and 60mg dose, respectively. The concentrations achieved were 71.8 ug/1 and 146 ug/1, respectively. [2]

Volume of distribution

The disposition of dihydrocodeine is described as a two compartment model. [2]

Protein binding

Not Available

Metabolism

Metabolized in the liver by CYP 2D6 into an active metabolite, dihydromorphine, and by CYP 3A4 into secondary primary metabolite, nordihydrocodeine. A third primary metabolite is dihydrocodeine-6-glucuronide. [1]

The time for mean peak concentration in acid metabolites is 1.76h and 1.98h for a 30 and 60mg dose, respectively. The concentrations achieved were 563 ug/1 and 1476 ug/1, respectively. [2]

Route of elimination

Renal elimination and urinary excretion. [1]

Half-life

4h

Clearance

Plasma clearance is approximately 300ml/min. [2]

The pharmacokinetics of dihydrocodeine and active metabolite dihydromorphine have been reported to be linear. [1]

The decline in plasma dihydrocodeine concentrations after intravenous administration has been described as bi-exponential, with a sleep decline in the initial 2h following administration, followed by a mono-exponential decline thereafter. Clearance was not dose dependent. [2]

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
1,2-BenzodiazepineThe risk or severity of adverse effects can be increased when Dihydrocodeine is combined with 1,2-Benzodiazepine.
AbametapirThe serum concentration of Dihydrocodeine can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Dihydrocodeine can be increased when combined with Abatacept.
AbirateroneThe metabolism of Dihydrocodeine can be decreased when combined with Abiraterone.
AcebutololThe metabolism of Dihydrocodeine can be decreased when combined with Acebutolol.
Food Interactions
  • Avoid alcohol. Alcohol can enhance the CNS depressant effects of this drug.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Dihydrocodeine bitartrate8LXS95BSA95965-13-9ZGSZBVAEVPSPFM-HYTSPMEMSA-N
Dihydrocodeine hydrochloride9073288YPO36418-29-8VMZXMTVGOAQUEN-FFHNEAJVSA-N
Dihydrocodeine hydroiodide6D04Y0152T5965-15-1COAKEBDIEZAZMT-FFHNEAJVSA-N
Dihydrocodeine phosphate5D9XI60ASE24204-13-5HFBYLYCMISIEMM-FFHNEAJVSA-N
Dihydrocodeine thiocyanate442C0H2H3P84824-87-3HVXYRJWFMXAVJG-FFHNEAJVSA-N
Active Moieties
NameKindUNIICASInChI Key
CodeineunknownUX6OWY2V7J76-57-3OROGSEYTTFOCAN-DNJOTXNNSA-N
International/Other Brands
Codidol / Contugesic / Dehace / DF-118 Forte / Dicogesic / Hydrocodin / Remedacen
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Acetaminophen, Caffeine and Dihydrocodeine BitartrateDihydrocodeine bitartrate (16 mg/1) + Acetaminophen (325 mg/1) + Caffeine (30 mg/1)TabletOralAtland Pharmaceuticals, Llc2020-01-30Not applicableUS flag
Acetaminophen, Caffeine and Dihydrocodeine BitartrateDihydrocodeine bitartrate (16 mg/1) + Acetaminophen (325 mg/1) + Caffeine (30 mg/1)TabletOralLarken Laboratories Inc.2016-10-04Not applicableUS flag
Acetaminophen, Caffeine and Dihydrocodeine BitartrateDihydrocodeine bitartrate (32 mg/1) + Acetaminophen (712.8 mg/1) + Caffeine (60 mg/1)TabletOralBoca Pharmacal, Inc.2007-04-032013-05-23US flag
Acetaminophen, Caffeine and Dihydrocodeine BitartrateDihydrocodeine bitartrate (32 mg/1) + Acetaminophen (712.8 mg/1) + Caffeine (60 mg/1)TabletOralMikart, Inc.2006-10-06Not applicableUS flag
Acetaminophen, Caffeine, Dihydrocodeine BitartrateDihydrocodeine bitartrate (16 mg/1) + Acetaminophen (320.5 mg/1) + Caffeine (30 mg/1)CapsuleOralPreferreed Pharmaceuticals Inc.2015-09-112018-03-05US flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Centussin DhcDihydrocodeine bitartrate (3 mg/5mL) + Brompheniramine maleate (4 mg/5mL) + Phenylephrine hydrochloride (7.5 mg/5mL)LiquidOralCenturion Labs2009-11-242016-05-02US flag
ColdcoughDihydrocodeine bitartrate (7.5 mg/5mL) + Chlorpheniramine maleate (2.0 mg/5mL) + Pseudoephedrine hydrochloride (15 mg/5mL)SyrupOralBreckenridge Pharmaceutical, Inc.2003-07-012011-08-31US flag
Coldcough PDDihydrocodeine bitartrate (3 mg/5mL) + Chlorpheniramine maleate (2 mg/5mL) + Phenylephrine hydrochloride (7.5 mg/5mL)SyrupOralBreckenridge Pharmaceutical, Inc.2003-07-012011-12-31US flag
DiHydro CPDihydrocodeine bitartrate (7.5 mg/5mL) + Chlorpheniramine maleate (2 mg/5mL) + Pseudoephedrine hydrochloride (15 mg/5mL)SyrupOralCypress Pharmaceuticals, Inc.2007-02-152011-08-26US flag
Dihydrocodeine BPM Phenyleph HClDihydrocodeine bitartrate (3 mg/5mL) + Brompheniramine maleate (4 mg/5mL) + Phenylephrine hydrochloride (7.5 mg/5mL)LiquidOralRiver's Edge Pharmaceuticals, LLC2010-03-012012-02-29US flag

Categories

ATC Codes
N02AA58 — Dihydrocodeine, combinationsN02AA08 — DihydrocodeineN02AJ02 — Dihydrocodeine and acetylsalicylic acidN02AJ01 — Dihydrocodeine and paracetamol
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as 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.
Kingdom
Organic compounds
Super Class
Alkaloids and derivatives
Class
Morphinans
Sub Class
Not Available
Direct Parent
Morphinans
Alternative Parents
Phenanthrenes and derivatives / Tetralins / Coumarans / Anisoles / Aralkylamines / Alkyl aryl ethers / Piperidines / Trialkylamines / Secondary alcohols / Cyclic alcohols and derivatives
show 4 more
Substituents
Alcohol / Alkyl aryl ether / Amine / Anisole / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Coumaran / Cyclic alcohol
show 16 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
N9I9HDB855
CAS number
125-28-0
InChI Key
RBOXVHNMENFORY-DNJOTXNNSA-N
InChI
InChI=1S/C18H23NO3/c1-19-8-7-18-11-4-5-13(20)17(18)22-16-14(21-2)6-3-10(15(16)18)9-12(11)19/h3,6,11-13,17,20H,4-5,7-9H2,1-2H3/t11-,12+,13-,17-,18-/m0/s1
IUPAC Name
(1S,5R,13R,14S,17R)-10-methoxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0^{1,13}.0^{5,17}.0^{7,18}]octadeca-7,9,11(18)-trien-14-ol
SMILES
[H][C@@]12OC3=C4C(C[C@H]5N(C)CC[C@@]14[C@@]5([H])CC[C@@H]2O)=CC=C3OC

References

Synthesis Reference

Igor Likhotvorik, "Preparation of dihydrocodeine from codeine." U.S. Patent US06887999, issued May 03, 2005.

US06887999
General References
  1. Ammon S, Hofmann U, Griese EU, Gugeler N, Mikus G: Pharmacokinetics of dihydrocodeine and its active metabolite after single and multiple oral dosing. Br J Clin Pharmacol. 1999 Sep;48(3):317-22. [Article]
  2. Rowell FJ, Seymour RA, Rawlins MD: Pharmacokinetics of intravenous and oral dihydrocodeine and its acid metabolites. Eur J Clin Pharmacol. 1983;25(3):419-24. [Article]
  3. Schmidt H, Vormfelde SV, Walchner-Bonjean M, Klinder K, Freudenthaler S, Gleiter CH, Gundert-Remy U, Skopp G, Aderjan R, Fuhr U: The role of active metabolites in dihydrocodeine effects. Int J Clin Pharmacol Ther. 2003 Mar;41(3):95-106. [Article]
  4. FDA Approved Drug Products: SYNALGOS®-DC (aspirin, caffeine, and dihydrocodeine bitartrate) capsules, for oral use, CIII (Jan 2024) [Link]
KEGG Drug
D01481
PubChem Compound
5284543
PubChem Substance
46506478
ChemSpider
4447600
RxNav
23088
ChEBI
135276
ChEMBL
CHEMBL1595
ZINC
ZINC000004215736
PharmGKB
PA449322
Drugs.com
Drugs.com Drug Page
Wikipedia
Dihydrocodeine

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedTreatmentPain1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • A-S Medication Solutions LLC
  • Boca Pharmacal
  • Caraco Pharmaceutical Labs
  • Leitner Pharmaceuticals LLC
  • Mikart Inc.
  • Nucare Pharmaceuticals Inc.
  • Pamlab LLC
  • PD-Rx Pharmaceuticals Inc.
  • Pharmedix
  • Physicians Total Care Inc.
  • West-Ward Pharmaceuticals
  • Zerxis Pharmaceuticals
Dosage Forms
FormRouteStrength
TabletOral
CreamOral; Vaginal
Solution / dropsOral
Tablet, film coatedOral120 mg
Tablet, film coatedOral60 mg
Tablet, film coatedOral90 mg
TabletOral
SyrupOral0.242 g
SolutionOral242 mg
SolutionOral0.242 g
CapsuleOral
LiquidOral
SuspensionOral240 mg
SyrupOral242 mg
TabletOral10 mg
Solution / dropsOral10 mg/g
SyrupOral200 mg/100g
SolutionOral15 g
SolutionOral30 g
Solution / dropsOral10.25 mg/mL
SolutionOral13.6 mg
TabletOral30 mg
SyrupOral
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)112.5 °CPhysProp
Predicted Properties
PropertyValueSource
Water Solubility2.38 mg/mLALOGPS
logP1.58ALOGPS
logP1.55Chemaxon
logS-2.1ALOGPS
pKa (Strongest Acidic)14.15Chemaxon
pKa (Strongest Basic)9.33Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area41.93 Å2Chemaxon
Rotatable Bond Count1Chemaxon
Refractivity83.64 m3·mol-1Chemaxon
Polarizability32.8 Å3Chemaxon
Number of Rings5Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9942
Blood Brain Barrier+0.9974
Caco-2 permeable+0.8388
P-glycoprotein substrateSubstrate0.8754
P-glycoprotein inhibitor IInhibitor0.5937
P-glycoprotein inhibitor IINon-inhibitor0.9652
Renal organic cation transporterInhibitor0.5676
CYP450 2C9 substrateNon-substrate0.831
CYP450 2D6 substrateSubstrate0.9143
CYP450 3A4 substrateSubstrate0.7941
CYP450 1A2 substrateNon-inhibitor0.8554
CYP450 2C9 inhibitorNon-inhibitor0.9074
CYP450 2D6 inhibitorInhibitor0.7395
CYP450 2C19 inhibitorNon-inhibitor0.7689
CYP450 3A4 inhibitorNon-inhibitor0.8114
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.957
Ames testNon AMES toxic0.8074
CarcinogenicityNon-carcinogens0.9522
BiodegradationNot ready biodegradable0.9857
Rat acute toxicity2.9382 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9058
hERG inhibition (predictor II)Non-inhibitor0.8246
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0fe3-3090000000-0e18b782719802231e79
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0udi-0009000000-0621835c3e6c1a244d1c
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0udi-0009000000-215351ab6e3d6923cb7a
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0udi-0239000000-d9a28afb4f2a26a792fb
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0f6t-0931000000-8f6a91fec0761febddae
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-006t-0910000000-b17807fd1304c69ce71d
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0udi-0009000000-422aaa0732f083783954
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0udi-0009000000-6826eb02e5bf4f87fde7
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0udi-0359000000-b1a87ac83b5ead5b10ba
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0f6t-0941000000-85f127ae74a67d7544d7
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-006t-0910000000-fc3b87d3fb93d21f90f4
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-062d-0900000000-c8e88928923875169e0b
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-0009000000-64bcbcc1c824a7e9461f
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-0009000000-9fb44b80ffaa24d991b4
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-0039000000-cc5e53cd2d1d136f7e75
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-0029000000-2394e373e27bb522d111
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0zir-0092000000-b4b73651dbbc8973ce14
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4l-2091000000-8dee0d580487f5c8a97c
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-0009000000-64bcbcc1c824a7e9461f
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-0009000000-9fb44b80ffaa24d991b4
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-0029000000-2394e373e27bb522d111
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-0039000000-cc5e53cd2d1d136f7e75
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4l-2091000000-8dee0d580487f5c8a97c
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0zir-0092000000-b4b73651dbbc8973ce14
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-174.8310872
predicted
DarkChem Lite v0.1.0
[M-H]-175.4669872
predicted
DarkChem Lite v0.1.0
[M-H]-177.15668
predicted
DeepCCS 1.0 (2019)
[M-H]-174.8310872
predicted
DarkChem Lite v0.1.0
[M-H]-175.4669872
predicted
DarkChem Lite v0.1.0
[M-H]-177.15668
predicted
DeepCCS 1.0 (2019)
[M+H]+174.9010872
predicted
DarkChem Lite v0.1.0
[M+H]+175.4787872
predicted
DarkChem Lite v0.1.0
[M+H]+179.5262
predicted
DeepCCS 1.0 (2019)
[M+H]+174.9010872
predicted
DarkChem Lite v0.1.0
[M+H]+175.4787872
predicted
DarkChem Lite v0.1.0
[M+H]+179.5262
predicted
DeepCCS 1.0 (2019)
[M+Na]+175.3010872
predicted
DarkChem Lite v0.1.0
[M+Na]+175.5157872
predicted
DarkChem Lite v0.1.0
[M+Na]+186.96376
predicted
DeepCCS 1.0 (2019)
[M+Na]+175.3010872
predicted
DarkChem Lite v0.1.0
[M+Na]+175.5157872
predicted
DarkChem Lite v0.1.0
[M+Na]+186.96376
predicted
DeepCCS 1.0 (2019)

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Hutchinson MR, Menelaou A, Foster DJ, Coller JK, Somogyi AA: CYP2D6 and CYP3A4 involvement in the primary oxidative metabolism of hydrocodone by human liver microsomes. Br J Clin Pharmacol. 2004 Mar;57(3):287-97. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. Kirkwood LC, Nation RL, Somogyi AA: Characterization of the human cytochrome P450 enzymes involved in the metabolism of dihydrocodeine. Br J Clin Pharmacol. 1997 Dec;44(6):549-55. [Article]
  2. Schmidt H, Vormfelde Sv, Klinder K, Gundert-Remy U, Gleiter CH, Skopp G, Aderjan R, Fuhr U: Affinities of dihydrocodeine and its metabolites to opioid receptors. Pharmacol Toxicol. 2002 Aug;91(2):57-63. [Article]
  3. Fromm MF, Hofmann U, Griese EU, Mikus G: Dihydrocodeine: a new opioid substrate for the polymorphic CYP2D6 in humans. Clin Pharmacol Ther. 1995 Oct;58(4):374-82. doi: 10.1016/0009-9236(95)90049-7. [Article]
  4. Schmidt H, Vormfelde SV, Walchner-Bonjean M, Klinder K, Freudenthaler S, Gleiter CH, Gundert-Remy U, Skopp G, Aderjan R, Fuhr U: The role of active metabolites in dihydrocodeine effects. Int J Clin Pharmacol Ther. 2003 Mar;41(3):95-106. [Article]

Drug created at July 31, 2007 13:10 / Updated at January 22, 2024 17:49