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
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 |
---|---|---|
Mimicking gene defects to treat drug dependence. | 2000 |
|
Codeine analgesia is due to codeine-6-glucuronide, not morphine. | 2000 Jul-Aug |
|
Over-the-counter medications for acute cough in children and adults in ambulatory settings. | 2001 |
|
Dystonia as acute adverse reaction to cough suppressant in a 3-year-old girl. | 2001 |
|
[Guillain-Barre syndrome as a result of poisoning with a mixture of "kompot"(Polish heroin) and drugs]. | 2001 |
|
Determination of opiates in serum, saliva and hair addicted persons. | 2001 |
|
Results of a phase-I/II randomized, masked, placebo-controlled trial of recombinant human interleukin-11 (rhIL-11) in the treatment of subjects with active rheumatoid arthritis. | 2001 |
|
The use of compound 48/80 and codeine phosphate as positive controls for intradermal skin testing in dogs. | 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 |
|
[Adverse cutaneous side-effect of codeine administration]. | 2001 Apr 15 |
|
Prescribing limitations. | 2001 Aug 11 |
|
Effect of prophylactic amoxicillin on endodontic flare-up in asymptomatic, necrotic teeth. | 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 |
|
Are cannabinoids an effective and safe treatment option in the management of pain? A qualitative systematic review. | 2001 Jul 7 |
|
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 |
|
Myocardial Infarction associated with methadone and/or dihydrocodeine. | 2001 Mar |
|
Acetylcodeine as a marker of illicit heroin in human hair: method validation and results of a pilot study. | 2001 Mar |
|
Effect of an enteric-release formulation of naloxone on intestinal transit in volunteers taking codeine. | 2001 May |
|
The analgesic effect of codeine as compared to imipramine in different human experimental pain models. | 2001 May |
|
[Analgesics-induced chronic renal failure in patients on dialysis therapy in Hungary]. | 2001 May 13 |
|
Capillary electrophoresis-electrospray ionization ion trap mass spectrometry for analysis and confirmation testing of morphine and related compounds in urine. | 2001 May 4 |
|
Regional block and mexiletine: the effect on pain after cancer breast surgery. | 2001 May-Jun |
|
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 |
|
Ropivacaine with or without clonidine improves pediatric tonsillectomy pain. | 2001 Oct |
|
Drug contamination of US paper currency. | 2001 Oct 1 |
|
Spontaneous reports on drug-induced pancreatitis in Denmark from 1968 to 1999. | 2001 Sep |
|
Community pharmacists' experience of over-the-counter medicine misuse in Scotland. | 2001 Sep |
|
Cetirizine inhibits skin reactions but not mediator release in immediate and developing late-phase allergic cutaneous reactions. A double-blind, placebo-controlled study. | 2001 Sep |
|
Rofecoxib versus codeine/acetaminophen in postoperative dental pain: a double-blind, randomized, placebo- and active comparator-controlled clinical trial. | 2001 Sep |
|
Blind trials of an onsite saliva drug test for marijuana and opiates. | 2001 Sep |
Sample Use Guides
In Vivo Use Guide
Sources: https://online.lexi.com/lco/medguides/622452.pdf
Unknown
Route of Administration:
Oral
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Classification Tree | Code System | Code | ||
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NDF-RT |
N0000175690
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NDF-RT |
N0000175684
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CFR |
21 CFR 862.3270
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DEA NO. |
9050
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WHO-ATC |
N02AJ09
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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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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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ACTIVE MOIETY
METABOLITE (PARENT)
METABOLITE ACTIVE (PRODRUG)
METABOLITE ACTIVE (PRODRUG)
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