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 |
|---|---|---|
| Saliva testing after single and chronic administration of dihydrocodeine. | 2001 |
|
| Dose-related effects of controlled release dihydrocodeine on oro-cecal transit and pupillary light reflex. A study in human volunteers. | 2001 Jan |
|
| Head-column field-amplified sample stacking in presence of siphoning. Application to capillary electrophoresis-electrospray ionization mass spectrometry of opioids in urine. | 2001 Jul 27 |
|
| Audit of pain management at home following tonsillectomy in children. | 2001 Mar |
|
| Treatment of severe pain from osteoarthritis with slow-release tramadol or dihydrocodeine in combination with NSAID's: a randomised study comparing analgesia, antinociception and gastrointestinal effects. | 2001 Mar |
|
| Evaluation of urinary dihydrocodeine excretion in human by gas chromatography-mass spectrometry. | 2001 Mar 5 |
|
| Dihydrocodeine--drug of use or misuse? | 2001 May |
|
| The role of dihydrocodeine in causing death among drug users in the west of Scotland. | 2001 Oct |
|
| Novel dynamic polymer coating for capillary electrophoresis in nonaqueous methanolic background electrolytes. | 2001 Oct |
|
| Predictors for completing an inpatient detoxification program among intravenous heroin users, methadone substituted and codeine substituted patients. | 2001 Oct 1 |
|
| Capillary electrophoresis and capillary electrophoresis-ion trap multiple-stage mass spectrometry for the differentiation and identification of oxycodone and its major metabolites in human urine. | 2002 Apr 25 |
|
| [Clinical study of BRON-L syrup (cough suppressant) abuse]. | 2002 Feb |
|
| Diclofenac does not interact with codeine metabolism in vivo: a study in healthy volunteers. | 2002 Feb 27 |
|
| Alcohol consumption in heroin users, methadone-substituted and codeine-substituted patients--frequency and correlates of use. | 2003 Jan |
|
| The role of active metabolites in dihydrocodeine effects. | 2003 Mar |
|
| Pharmacokinetic drug interactions of morphine, codeine, and their derivatives: theory and clinical reality, Part II. | 2003 Nov-Dec |
|
| The Leeds Evaluation of Efficacy of Detoxification Study (LEEDS) project: an open-label pragmatic randomised control trial comparing the efficacy of differing therapeutic agents for primary care detoxification from either street heroin or methadone [ISRCTN07752728]. | 2004 Apr 29 |
|
| Is intraperitoneal levobupivacaine with epinephrine useful for analgesia following laparoscopic cholecystectomy? A randomized controlled trial. | 2004 Aug |
|
| Activation of G-proteins by morphine and codeine congeners: insights to the relevance of O- and N-demethylated metabolites at mu- and delta-opioid receptors. | 2004 Feb |
|
| Evaluation of the One-Step ELISA kit for the detection of buprenorphine in urine, blood, and hair specimens. | 2004 Jul 16 |
|
| 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 |
|
| Replacement of immunoassay by LC tandem mass spectrometry for the routine measurement of drugs of abuse in oral fluid. | 2005 Jul |
|
| The effect of non-steroidal anti-inflammatory drugs on medical abortion with mifepristone and misoprostol at 13-22 weeks gestation. | 2005 Nov |
|
| 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 |
|
| 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 |
|
| Response to hydrocodone, codeine and oxycodone in a CYP2D6 poor metabolizer. | 2006 Sep 30 |
|
| 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 |
|
| 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 |
|
| Central and peripheral mechanisms of narcotic antitussives: codeine-sensitive and -resistant coughs. | 2007 Jul 9 |
|
| 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 |
|
| Factors that help injecting drug users to access and benefit from services: A qualitative study. | 2007 Oct 30 |
|
| 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 |
| Name | Type | Language | ||
|---|---|---|---|---|
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English |
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
DTXSID60189946
Created by
admin on Sat Dec 16 08:39:47 GMT 2023 , Edited by admin on Sat Dec 16 08:39:47 GMT 2023
|
PRIMARY | |||
|
100000078578
Created by
admin on Sat Dec 16 08:39:47 GMT 2023 , Edited by admin on Sat Dec 16 08:39:47 GMT 2023
|
PRIMARY | |||
|
5492723
Created by
admin on Sat Dec 16 08:39:47 GMT 2023 , Edited by admin on Sat Dec 16 08:39:47 GMT 2023
|
PRIMARY | |||
|
9073288YPO
Created by
admin on Sat Dec 16 08:39:47 GMT 2023 , Edited by admin on Sat Dec 16 08:39:47 GMT 2023
|
PRIMARY | |||
|
DBSALT000050
Created by
admin on Sat Dec 16 08:39:47 GMT 2023 , Edited by admin on Sat Dec 16 08:39:47 GMT 2023
|
PRIMARY | |||
|
SUB16417MIG
Created by
admin on Sat Dec 16 08:39:47 GMT 2023 , Edited by admin on Sat Dec 16 08:39:47 GMT 2023
|
PRIMARY | |||
|
36418-29-8
Created by
admin on Sat Dec 16 08:39:47 GMT 2023 , Edited by admin on Sat Dec 16 08:39:47 GMT 2023
|
PRIMARY | |||
|
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
|
PRIMARY |
ACTIVE MOIETY
SUBSTANCE RECORD
