Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C18H21NO3 |
Molecular Weight | 299.3642 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 5 / 5 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=C2O[C@H]3[C@@H](O)C=C[C@H]4[C@H]5CC(C=C1)=C2[C@@]34CCN5C
InChI
InChIKey=OROGSEYTTFOCAN-DNJOTXNNSA-N
InChI=1S/C18H21NO3/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,7-9H2,1-2H3/t11-,12+,13-,17-,18-/m0/s1
Molecular Formula | C18H21NO3 |
Molecular Weight | 299.3642 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 5 / 5 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Codeine is an opiate used to manage mild to moderate pain severe enough to require an opioid. Codeine is a selective agonist for the mu opioid receptor and has an affinity to delta and kappa-opioid receptors. In some countries, this drug is regulated under various narcotic control laws, because its chronic use can cause physical dependence. In others, it is available without a medical prescription in combination with paracetamol.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL233 |
6.1 µM [EC50] | ||
Target ID: P41145 Gene ID: 4986.0 Gene Symbol: OPRK1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/7885194 |
|||
Target ID: P41143 Gene ID: 4985.0 Gene Symbol: OPRD1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/7885194 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | CAPITAL AND CODEINE Approved UseUnknown |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
66.9 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1391681/ |
30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered: |
CODEINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
145 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7094509/ |
60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered: |
CODEINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
229 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7094509/ |
60 mg single, intramuscular dose: 60 mg route of administration: Intramuscular experiment type: SINGLE co-administered: |
CODEINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
93 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7094509/ |
60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered: |
CODEINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
242 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7094509/ |
60 mg single, intramuscular dose: 60 mg route of administration: Intramuscular experiment type: SINGLE co-administered: |
CODEINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
53.5 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1391681/ |
30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered: |
MORPHINE-3-GLUCURONIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
66.9 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1391681/ |
30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered: |
CODEINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
968 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1391681/ |
30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered: |
CODEINE-6-GLUCURONIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
0.61 μM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1391681/ |
30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered: |
CODEINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
466 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7094509/ |
60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered: |
CODEINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
849 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7094509/ |
60 mg single, intramuscular dose: 60 mg route of administration: Intramuscular experiment type: SINGLE co-administered: |
CODEINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
467 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7094509/ |
60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered: |
CODEINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
937 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7094509/ |
60 mg single, intramuscular dose: 60 mg route of administration: Intramuscular experiment type: SINGLE co-administered: |
CODEINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1.47 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1391681/ |
30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered: |
CODEINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
2.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7094509/ |
60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered: |
CODEINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
2.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7094509/ |
60 mg single, intramuscular dose: 60 mg route of administration: Intramuscular experiment type: SINGLE co-administered: |
CODEINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
2.7 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7094509/ |
60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered: |
CODEINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
2.9 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7094509/ |
60 mg single, intramuscular dose: 60 mg route of administration: Intramuscular experiment type: SINGLE co-administered: |
CODEINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
1.71 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1391681/ |
30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered: |
MORPHINE-3-GLUCURONIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
1.47 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1391681/ |
30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered: |
CODEINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
2.75 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1391681/ |
30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered: |
CODEINE-6-GLUCURONIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
75% |
15 mg single, oral dose: 15 mg route of administration: Oral experiment type: SINGLE co-administered: |
CODEINE plasma | Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
inconclusive [IC50 35.7774 uM] | ||||
no | ||||
no | ||||
no | ||||
no | ||||
unlikely [IC50 400 uM] | ||||
yes [IC50 10.5 uM] |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 24.0 |
major | |||
Page: 20.0 |
major | |||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
Page: 20.0 |
yes | |||
Page: 20.0 |
yes | |||
yes | ||||
yes | ||||
yes |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
---|---|---|
Codeine analgesia is due to codeine-6-glucuronide, not morphine. | 2000 Jul-Aug |
|
Saliva testing after single and chronic administration of dihydrocodeine. | 2001 |
|
Pharmacological control of cough. | 2001 Apr |
|
Chromatographic analysis of phenethylamine-antihistamine combinations using C8, C18 or cyano columns and micellar sodium dodecyl sulfate-pentanol mixtures. | 2001 Apr |
|
Angle closure risk from proprietary medicines. | 2001 Apr |
|
The diagnosis and treatment of cough. | 2001 Apr 5 |
|
Prescribing limitations. | 2001 Aug 11 |
|
Precipitated withdrawal following codeine administration is dependent on CYP genotype. | 2001 Aug 17 |
|
Opioids for chronic nonmalignant pain. Attitudes and practices of primary care physicians in the UCSF/Stanford Collaborative Research Network. University of California, San Francisco. | 2001 Feb |
|
The safety of dextromethorphan in pregnancy : results of a controlled study. | 2001 Feb |
|
No pain relief from codeine...? An introduction to pharmacogenomics. | 2001 Feb |
|
Detection of acetylcodeine in urine as an indicator of illicit heroin use: method validation and results of a pilot study. | 2001 Feb |
|
Dose-related effects of controlled release dihydrocodeine on oro-cecal transit and pupillary light reflex. A study in human volunteers. | 2001 Jan |
|
Successful use of propranolol in migraine associated with electroconvulsive therapy. | 2001 Jan |
|
Inhibition by glucocorticoids of the mast cell-dependent weal and flare response in human skin in vivo. | 2001 Jan |
|
Packaging of codeine phosphate suppositories. | 2001 Jan |
|
Using evidence from different sources: an example using paracetamol 1000 mg plus codeine 60 mg. | 2001 Jan 10 |
|
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 |
|
Use of beta-cyclodextrin in the capillary zone electrophoretic separation of the components of clandestine heroin preparations. | 2001 Jul 27 |
|
Successful withdrawal from analgesic abuse in a group of youngsters with chronic daily headache. | 2001 Jun |
|
Myth: codeine is a powerful and effective analgesic. | 2001 Jun |
|
Oral ibuprofen versus paracetamol plus codeine for analgesia after ambulatory surgery. | 2001 Jun |
|
Ulcerated hemangiomas: clinical characteristics and response to therapy. | 2001 Jun |
|
Analysis of cocaine, benzoylecgonine, codeine, and morphine in hair by supercritical fluid extraction with carbon dioxide modified with methanol. | 2001 Jun 1 |
|
Time of drug elimination in chronic drug abusers. Case study of 52 patients in a "low-step" detoxification ward. | 2001 Jun 15 |
|
Codeine phosphate in paediatric medicine. | 2001 Mar |
|
Codeine phosphate in children: time for re-evaluation? | 2001 Mar |
|
Expression and activity of cell-wall-degrading enzymes in the latex of opium poppy, Papaver somniferum L. | 2001 Mar |
|
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 |
|
Generalized eczema due to codeine. | 2001 Mar |
|
Dextromethorphan is an effective cough suppressant. | 2001 May |
|
Capillary electrophoresis-electrospray ionization ion trap mass spectrometry for analysis and confirmation testing of morphine and related compounds in urine. | 2001 May 4 |
|
Selective antibodies to methadone enantiomers: synthesis of (R)- and (R,S)-methadone conjugates and determination by an immunoenzymatic method in human serum. | 2001 May 5 |
|
From codeine to transdermal fentanyl for cancer pain control: a safety and efficacy clinical trial. | 2001 May-Jun |
|
Application of liquid chromatography to the simultaneous determination of acetylsalicylic acid, caffeine, codeine, paracetamol, pyridoxine, and thiamine in pharmaceutical preparations. | 2001 May-Jun |
|
Regional block and mexiletine: the effect on pain after cancer breast surgery. | 2001 May-Jun |
|
Concentration ratios of morphine to codeine in blood of impaired drivers as evidence of heroin use and not medication with codeine. | 2001 Nov |
|
The role of adrenal corticosteroids in induction of micronuclei by morphine. | 2001 Nov 15 |
|
Nutritional effects of surgical and medical treatment for short bowel syndrome. | 2001 Nov-Dec |
|
Novel dynamic polymer coating for capillary electrophoresis in nonaqueous methanolic background electrolytes. | 2001 Oct |
|
Incorporation of selegiline metabolites into hair after oral selegiline intake. | 2001 Oct |
|
Drug contamination of US paper currency. | 2001 Oct 1 |
|
Blind trials of an onsite saliva drug test for marijuana and opiates. | 2001 Sep |
|
Engineering novel biocatalytic routes for production of semisynthetic opiate drugs. | 2001 Sep |
|
Experience with urine drug testing by the Correctional Service of Canada. | 2001 Sep 15 |
Sample Use Guides
In Vivo Use Guide
Sources: https://online.lexi.com/lco/medguides/622452.pdf
Unknown
Route of Administration:
Oral
Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:29:42 GMT 2025
by
admin
on
Mon Mar 31 18:29:42 GMT 2025
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Record UNII |
UX6OWY2V7J
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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NDF-RT |
N0000175690
Created by
admin on Mon Mar 31 18:29:42 GMT 2025 , Edited by admin on Mon Mar 31 18:29:42 GMT 2025
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NDF-RT |
N0000175684
Created by
admin on Mon Mar 31 18:29:42 GMT 2025 , Edited by admin on Mon Mar 31 18:29:42 GMT 2025
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CFR |
21 CFR 862.3270
Created by
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DEA NO. |
9050
Created by
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WHO-ATC |
N02AJ09
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Code System | Code | Type | Description | ||
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DB00318
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100000079790
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76-57-3
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C171855
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200-969-1
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5284371
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m3718
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PRIMARY | Merck Index | ||
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C77284
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16714
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DTXSID2020341
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SS85U8K5ZN
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UX6OWY2V7J
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236131
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1545976
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3043
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SUB127261
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SUB13424MIG
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UX6OWY2V7J
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Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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BINDER->LIGAND |
BINDING
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SALT/SOLVATE -> PARENT |
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SOLVATE->ANHYDROUS | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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METABOLIC ENZYME -> SUBSTRATE | |||
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SUB_CONCEPT->SUBSTANCE | |||
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT | |||
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METABOLIC ENZYME -> SUBSTRATE | |||
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SALT/SOLVATE -> PARENT |
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METABOLIC ENZYME -> SUBSTRATE |
Related Record | Type | Details | ||
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METABOLITE -> PARENT |
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METABOLITE INACTIVE -> PARENT |
Metabolic Enzyme - cytochrome P-450 3A4
|
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METABOLITE ACTIVE -> PRODRUG |
MAJOR METABOLITE MAY BE RESPONSIBLE FOR ANALGESIC EFFECT
MAJOR
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METABOLITE ACTIVE -> PRODRUG |
MINOR METABOLITE
MINOR
|
Related Record | Type | Details | ||
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PARENT -> IMPURITY |
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PARENT -> IMPURITY |
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PARENT -> IMPURITY | |||
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PARENT -> IMPURITY | |||
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PARENT -> IMPURITY | |||
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PARENT -> IMPURITY |
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Related Record | Type | Details | ||
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ACTIVE MOIETY |