Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C18H21NO3.ClH.2H2O |
| Molecular Weight | 371.856 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 5 / 5 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O.O.Cl.COC1=C2O[C@H]3[C@@H](O)C=C[C@H]4[C@H]5CC(C=C1)=C2[C@@]34CCN5C
InChI
InChIKey=AWFZELCPUGEQGQ-NLMNJOOOSA-N
InChI=1S/C18H21NO3.ClH.2H2O/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;1H;2*1H2/t11-,12+,13-,17-,18-;;;/m0.../s1
| Molecular Formula | ClH |
| Molecular Weight | 36.461 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| 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 |
| Molecular Formula | H2O |
| Molecular Weight | 18.0153 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
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) |
|||
Target ID: P41143 Gene ID: 4985.0 Gene Symbol: OPRD1 Target Organism: Homo sapiens (Human) |
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 |
|---|---|---|---|---|
| major | ||||
| major | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| yes | ||||
| yes | ||||
| yes | ||||
| yes | ||||
| yes |
Tox targets
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
PubMed
| Title | Date | PubMed |
|---|---|---|
| Analgesic abuse, ureteric obstruction, and retroperitoneal fibrosis. | 1975 Apr 12 |
|
| 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 |
|
| [Pharmacokinetic and toxicokinetic parameters of some drugs of abuse]. | 2001 |
|
| The use of compound 48/80 and codeine phosphate as positive controls for intradermal skin testing in dogs. | 2001 Apr |
|
| Sticky business: patterns of procurement and misuse of prescription cough syrup in Houston. | 2001 Apr-Jun |
|
| Randomized placebo controlled trial of lofexidine hydrochloride for chronic pelvic pain in women. | 2001 Aug |
|
| Simultaneous determination of codeine and ethyl morphine HCL in tablet formulations using LC. | 2001 Aug |
|
| Precipitated withdrawal following codeine administration is dependent on CYP genotype. | 2001 Aug 17 |
|
| [Paracetamol-codeine induced hepatic colic]. | 2001 Aug-Sep |
|
| The safety of dextromethorphan in pregnancy : results of a controlled study. | 2001 Feb |
|
| No pain relief from codeine...? An introduction to pharmacogenomics. | 2001 Feb |
|
| Dose-related effects of controlled release dihydrocodeine on oro-cecal transit and pupillary light reflex. A study in human volunteers. | 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 |
|
| Opiate-sensitivity: clinical characteristics and the role of skin prick testing. | 2001 Jul |
|
| Contribution of dihydrocodeine and dihydromorphine to analgesia following dihydrocodeine administration in man: a PK-PD modelling analysis. | 2001 Jul |
|
| Heroin use by motorists in Sweden confirmed by analysis of 6-acetylmorphine in urine. | 2001 Jul-Aug |
|
| [Chronic pain in geriatrics]. | 2001 Jun |
|
| Effect of apical trephination on postoperative pain and swelling in symptomatic necrotic teeth. | 2001 Jun |
|
| Myth: codeine is a powerful and effective analgesic. | 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 |
|
| Myocardial Infarction associated with methadone and/or dihydrocodeine. | 2001 Mar |
|
| GC-MS determination of heroin metabolites in meconium: evaluation of four solid-phase extraction cartridges. | 2001 Mar |
|
| Quantitation of morphine and codeine in human urine using high-filed asymmetric waveform ion mobility spectrometry (FAIMS) with mass spectrometric detection. | 2001 Mar |
|
| Opiate use to control bowel motility may induce chronic daily headache in patients with migraine. | 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 |
|
| Dextromethorphan is an effective cough suppressant. | 2001 May |
|
| Dihydrocodeine--drug of use or misuse? | 2001 May |
|
| Effect of an enteric-release formulation of naloxone on intestinal transit in volunteers taking codeine. | 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 |
|
| Application of liquid chromatography to the simultaneous determination of acetylsalicylic acid, caffeine, codeine, paracetamol, pyridoxine, and thiamine in pharmaceutical preparations. | 2001 May-Jun |
|
| Scalp nerve blocks decrease the severity of pain after craniotomy. | 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 |
|
| Seizures with intravenous codeine phosphate. | 2001 Oct |
|
| Ropivacaine with or without clonidine improves pediatric tonsillectomy pain. | 2001 Oct |
|
| Drug contamination of US paper currency. | 2001 Oct 1 |
|
| Predictors for completing an inpatient detoxification program among intravenous heroin users, methadone substituted and codeine substituted patients. | 2001 Oct 1 |
|
| Endogenous morphine and codeine. Possible role as endogenous anticonvulsants. | 2001 Oct 12 |
|
| Community pharmacists' experience of over-the-counter medicine misuse in Scotland. | 2001 Sep |
|
| [Strong opioids]. | 2001 Sep |
|
| Concentration ratios of codeine-to-morphine in plasma after a single oral dose (100 mg) of codeine phosphate. | 2001 Sep |
|
| Experience with urine drug testing by the Correctional Service of Canada. | 2001 Sep 15 |
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:39:15 GMT 2025
by
admin
on
Mon Mar 31 18:39:15 GMT 2025
|
| Record UNII |
NTZ53GG7XN
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
Download
| Name | Type | Language | ||
|---|---|---|---|---|
|
Preferred Name | English | ||
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Common Name | English | ||
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Systematic Name | English | ||
|
Common Name | English | ||
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Common Name | English | ||
|
Common Name | English |
| Classification Tree | Code System | Code | ||
|---|---|---|---|---|
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DEA NO. |
9050
Created by
admin on Mon Mar 31 18:39:15 GMT 2025 , Edited by admin on Mon Mar 31 18:39:15 GMT 2025
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| Code System | Code | Type | Description | ||
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NTZ53GG7XN
Created by
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DBSALT001068
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Codeine hydrochloride
Created by
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DTXSID10207886
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SUB01405MIG
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1115966
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44146477
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SUB11840MIG
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5916-29-0
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100000076636
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ACTIVE MOIETY |