Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C18H23NO3.ClH |
| Molecular Weight | 337.841 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 5 / 5 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.[H][C@@]12OC3=C4C(C[C@H]5N(C)CC[C@@]14[C@@]5([H])CC[C@@H]2O)=CC=C3OC
InChI
InChIKey=VMZXMTVGOAQUEN-FFHNEAJVSA-N
InChI=1S/C18H23NO3.ClH/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;1H/t11-,12+,13-,17-,18-;/m0./s1
DescriptionSources: http://www.drugbank.ca/drugs/DB01551Curator's Comment: Description was created based on several sources, including
Sources: http://www.drugbank.ca/drugs/DB01551
Curator's Comment: Description was created based on several sources, including
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. Dihydrocodeine is metabolized to dihydromorphine -- a highly active metabolite with a high affinity for mu opioid receptors. Dihydrocodeine is used for the treatment of moderate to severe pain, including post-operative and dental pain. It can also be used to treat chronic pain, breathlessness and coughing. In heroin addicts, dihydrocodeine has been used as a substitute drug, in doses up to 2500mg/day to treat addiction.
CNS Activity
Approval Year
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
487 pmol/g |
60 mg 2 times / day multiple, oral dose: 60 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
DIHYDROCODEINE serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
341 nM |
60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered: |
DIHYDROCODEINE serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
739 nM |
90 mg 1 times / day multiple, oral dose: 90 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
DIHYDROCODEINE serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
918 nM |
120 mg 1 times / day multiple, oral dose: 120 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
DIHYDROCODEINE serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
60.089 ng/mL |
20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered: |
DIHYDROCODEINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
18 nM |
120 mg 1 times / day multiple, oral dose: 120 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
DIHYDROMORPHINE serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
8.7 nM |
60 mg 1 times / day multiple, oral dose: 60 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
DIHYDROMORPHINE serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
4.7 pmol/g |
60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered: |
DIHYDROMORPHINE serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
13 nM |
90 mg 1 times / day multiple, oral dose: 90 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
DIHYDROMORPHINE serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
3367 nM × h |
60 mg 2 times / day multiple, oral dose: 60 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
DIHYDROCODEINE serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
3415 nM × h |
60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered: |
DIHYDROCODEINE serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
5118 nM × h |
90 mg 1 times / day multiple, oral dose: 90 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
DIHYDROCODEINE serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
6566 nM × h |
120 mg 1 times / day multiple, oral dose: 120 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
DIHYDROCODEINE serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
301.643 ng × h/mL |
20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered: |
DIHYDROCODEINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
132 nM × h |
120 mg 1 times / day multiple, oral dose: 120 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
DIHYDROMORPHINE serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
65 nM × h |
60 mg 1 times / day multiple, oral dose: 60 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
DIHYDROMORPHINE serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
70 nM × h |
60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered: |
DIHYDROMORPHINE serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
99 nM × h |
90 mg 1 times / day multiple, oral dose: 90 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
DIHYDROMORPHINE serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
3.146 h |
20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered: |
DIHYDROCODEINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
Doses
| Dose | Population | Adverse events |
|---|---|---|
32 mg 6 times / day multiple, oral Recommended Dose: 32 mg, 6 times / day Route: oral Route: multiple Dose: 32 mg, 6 times / day Co-administed with:: aspirin(356.4 mg) Sources: caffeine(30 mg) |
unhealthy, > 18 years Health Status: unhealthy Age Group: > 18 years Sources: |
Other AEs: Respiratory depression... Other AEs: Respiratory depression (grade 5) Sources: |
240 mg 2 times / day multiple, oral Overdose Dose: 240 mg, 2 times / day Route: oral Route: multiple Dose: 240 mg, 2 times / day Sources: |
unhealthy |
Other AEs: Hypercapnic respiratory failure... |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Respiratory depression | grade 5 | 32 mg 6 times / day multiple, oral Recommended Dose: 32 mg, 6 times / day Route: oral Route: multiple Dose: 32 mg, 6 times / day Co-administed with:: aspirin(356.4 mg) Sources: caffeine(30 mg) |
unhealthy, > 18 years Health Status: unhealthy Age Group: > 18 years Sources: |
| Hypercapnic respiratory failure | 240 mg 2 times / day multiple, oral Overdose Dose: 240 mg, 2 times / day Route: oral Route: multiple Dose: 240 mg, 2 times / day Sources: |
unhealthy |
PubMed
| Title | Date | PubMed |
|---|---|---|
| ECG abnormalities in co-proxamol (paracetamol/dextropropoxyphene) poisoning. | 2005 |
|
| Simultaneous analysis of thebaine, 6-MAM and six abused opiates in postmortem fluids and tissues using Zymark automated solid-phase extraction and gas chromatography-mass spectrometry. | 2005 Aug 5 |
|
| Clinical urinalysis of drugs and alcohol in instances of suspected surreptitious administration ("spiked drinks"). | 2005 Jul-Sep |
|
| The effect of non-steroidal anti-inflammatory drugs on medical abortion with mifepristone and misoprostol at 13-22 weeks gestation. | 2005 Nov |
|
| Evaluation of buprenorphine CEDIA assay versus GC-MS and ELISA using urine samples from patients in substitution treatment. | 2005 Nov-Dec |
|
| Pain and pain treatments in European palliative care units. A cross sectional survey from the European Association for Palliative Care Research Network. | 2005 Sep |
|
| Palliative management of refractory dyspnea in COPD. | 2006 |
|
| Hyperinflation and its management in COPD. | 2006 |
|
| Opiate receptor binding properties of morphine-, dihydromorphine-, and codeine 6-O-sulfate ester congeners. | 2006 Aug 15 |
|
| Addressing the efficacy of dihydrocodeine versus methadone as an alternative maintenance treatment for opiate dependence: A randomized controlled trial. | 2006 Dec |
|
| Simultaneous determination of psychoactive drugs and their metabolites in aqueous matrices by liquid chromatography mass Spectrometry. | 2006 Dec 1 |
|
| Simple and sensitive determination of free and total morphine in human liver and kidney using gas chromatography-mass spectrometry. | 2006 Jan 18 |
|
| Treatment of pain during medical abortion. | 2006 Jul |
|
| Transdermal buprenorphine in the management of persistent pain - safety aspects. | 2006 Mar |
|
| Validation of the Immunalysis microplate ELISA for the detection of buprenorphine and its metabolite norbuprenorphine in urine. | 2006 Mar |
|
| Comparison of an automated and point-of-care immunoassay to GC-MS for urine oxycodone testing in the clinical laboratory. | 2006 Mar |
|
| Substance abuse in pregnancy: opioid substitution in a northern Ireland maternity unit. | 2006 Sep |
|
| Review of deaths related to analgesic- and cough suppressant-opioids; England and Wales 1996-2002. | 2006 Sep |
|
| An exploratory study in the UK of the effectiveness of three different pain management regimens for post-caesarean section women. | 2006 Sep |
|
| Response to hydrocodone, codeine and oxycodone in a CYP2D6 poor metabolizer. | 2006 Sep 30 |
|
| Glucuronidation of paracetamol by human liver microsomes in vitro / enzyme kinetic parameters and interactions with short-chain aliphatic alcohols and opiates. | 2007 |
|
| [Transient sick sinus syndrome by oral intake of high dose dehydrocodeine for postherpetic neuralgia]. | 2007 Apr |
|
| Interrupted time-series analysis of regulations to reduce paracetamol (acetaminophen) poisoning. | 2007 Apr |
|
| Dihydrocodeine as effective as methadone for maintenance of treatment for opiate dependence? | 2007 Aug |
|
| Deglutition and respiration: development, coordination, and practical implications. | 2007 Aug |
|
| Distribution of drugs of abuse within specific regions of the human brain. | 2007 Aug 6 |
|
| Patterns in drug use in the United Kingdom as revealed through analysis of hair in a large population sample. | 2007 Aug 6 |
|
| London audit of drug-related overdose deaths: characteristics and typology, and implications for prevention and monitoring. | 2007 Feb |
|
| Evaluation of the lipophilic properties of opioids, amphetamine-like drugs, and metabolites through electrochemical studies at the interface between two immiscible solutions. | 2007 Feb 15 |
|
| Substitution treatment for opioid addicts in Germany. | 2007 Feb 2 |
|
| The Leeds Evaluation of Efficacy of Detoxification Study (LEEDS) prisons project pilot study: protocol for a randomised controlled trial comparing dihydrocodeine and buprenorphine for opiate detoxification. | 2007 Jan 8 |
|
| Buprenorphine versus dihydrocodeine for opiate detoxification in primary care: a randomised controlled trial. | 2007 Jan 8 |
|
| A mixed methods study to investigate needs assessment for knee pain and disability: population and individual perspectives. | 2007 Jul 4 |
|
| Central and peripheral mechanisms of narcotic antitussives: codeine-sensitive and -resistant coughs. | 2007 Jul 9 |
|
| The enantiomers of tramadol and its major metabolite inhibit peristalsis in the guinea pig small intestine via differential mechanisms. | 2007 Mar 16 |
|
| "Me's me and you's you": Exploring patients' perspectives of single patient (n-of-1) trials in the UK. | 2007 Mar 19 |
|
| Pharmacokinetic-pharmacodynamic modeling of the miotic effects of dihydrocodeine in humans. | 2007 Nov |
|
| The role of tramadol in current treatment strategies for musculoskeletal pain. | 2007 Oct |
|
| The effect of ethanol on the release of opioids from oral prolonged-release preparations. | 2007 Oct |
|
| Factors that help injecting drug users to access and benefit from services: A qualitative study. | 2007 Oct 30 |
|
| Hemodynamic effects of methadone and dihydrocodeine in overdose. | 2007 Oct-Nov |
|
| Method for quantification of opioids and their metabolites in autopsy blood by liquid chromatography-tandem mass spectrometry. | 2007 Sep |
|
| Development and GC-MS validation of a highly sensitive recombinant G6PDH-based homogeneous immunoassay for the detection of buprenorphine and norbuprenorphine in urine. | 2007 Sep |
|
| The management of dyspnea in cancer patients: a systematic review. | 2008 Apr |
|
| Resolution of secondary amenorrhoea following withdrawal of dihydocodeine. | 2008 Apr |
|
| Hepatotoxicity associated with sulfasalazine in inflammatory arthritis: A case series from a local surveillance of serious adverse events. | 2008 Apr 11 |
|
| [Liposomal boron delivery system for neutron capture therapy]. | 2008 Feb |
|
| Comparison of analgesic effects and patient tolerability of nabilone and dihydrocodeine for chronic neuropathic pain: randomised, crossover, double blind study. | 2008 Jan 26 |
|
| Differentiation between drug use and environmental contamination when testing for drugs in hair. | 2008 Mar 21 |
|
| Primary care incidence and treatment of four neuropathic pain conditions: a descriptive study, 2002-2005. | 2008 May 6 |
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| Code System | Code | Type | Description | ||
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DTXSID60189946
Created by
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100000078578
Created by
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5492723
Created by
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9073288YPO
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DBSALT000050
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SUB16417MIG
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36418-29-8
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253-026-1
Created by
admin on Sat Dec 16 08:39:47 GMT 2023 , Edited by admin on Sat Dec 16 08:39:47 GMT 2023
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ACTIVE MOIETY
SUBSTANCE RECORD
