U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS
This repository is under review for potential modification in compliance with Administration directives.

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
Structure of CODEINE ANHYDROUS

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

HIDE SMILES / InChI

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
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

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
CAPITAL AND CODEINE

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
66.9 ng/mL
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
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
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
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
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
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
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
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

AUC

ValueDoseCo-administeredAnalytePopulation
0.61 μM × h
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
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
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
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
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

T1/2

ValueDoseCo-administeredAnalytePopulation
1.47 h
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
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
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
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
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
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
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
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

Funbound

ValueDoseCo-administeredAnalytePopulation
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
Doses

Doses

DosePopulationAdverse events​
360 mg 1 times / day multiple, oral
Highest recorded dose
Dose: 360 mg, 1 times / day
Route: oral
Route: multiple
Dose: 360 mg, 1 times / day
Sources:
unhealthy
Health Status: unhealthy
Sex: M+F
Food Status: UNKNOWN
Sources:
OverviewDrug as perpetrator​Drug as victimTox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
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
Patents

Sample Use Guides

Unknown
Route of Administration: Oral
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:29:42 GMT 2025
Edited
by admin
on Mon Mar 31 18:29:42 GMT 2025
Record UNII
UX6OWY2V7J
Record Status Validated (UNII)
Record Version
  • Download
Related Record Type
Name Type Language
IDS-NC-005(SECT.-2)
Preferred Name English
CODEINE ANHYDROUS
Common Name English
MYTUSSIN
Common Name English
ETHYLMORPHINE HYDROCHLORIDE IMPURITY C [EP IMPURITY]
Common Name English
CODEINE [HSDB]
Common Name English
CODEINE [MI]
Common Name English
SS85U8K5ZN
Common Name English
KODELAK FITO
Common Name English
MORPHINE MONOMETHYL ETHER
Common Name English
HYDROCODONE HYDROGEN TARTRATE 2.5-HYDRATE IMPURITY C [EP IMPURITY]
Common Name English
7,8-didehydro-4,5?-epoxy-3-methoxy-17-methylmorphinan-6?-ol
Systematic Name English
O3-METHYLMORPHINE
Common Name English
CODICEPT
Common Name English
DIHYDROCODEINE HYDROGEN TARTRATE IMPURITY A [EP IMPURITY]
Common Name English
Codeine [WHO-DD]
Common Name English
METHYLMORPHINE
Common Name English
CODUCEPT
Common Name English
MORPHINAN-6-OL, 7,8-DIDEHYDRO-4,5-EPOXY-3-METHOXY-17-METHYL-, (5.ALPHA.,6.ALPHA.)-
Systematic Name English
MORPHINE SULFATE IMPURITY A [EP IMPURITY]
Common Name English
MORPHINE HYDROCHLORIDE IMPURITY A [EP IMPURITY]
Common Name English
Classification Tree Code System Code
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
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
CFR 21 CFR 862.3270
Created by admin on Mon Mar 31 18:29:42 GMT 2025 , Edited by admin on Mon Mar 31 18:29:42 GMT 2025
DEA NO. 9050
Created by admin on Mon Mar 31 18:29:42 GMT 2025 , Edited by admin on Mon Mar 31 18:29:42 GMT 2025
WHO-ATC N02AJ09
Created by admin on Mon Mar 31 18:29:42 GMT 2025 , Edited by admin on Mon Mar 31 18:29:42 GMT 2025
Code System Code Type Description
DRUG BANK
DB00318
Created by admin on Mon Mar 31 18:29:42 GMT 2025 , Edited by admin on Mon Mar 31 18:29:42 GMT 2025
PRIMARY
SMS_ID
100000079790
Created by admin on Mon Mar 31 18:29:42 GMT 2025 , Edited by admin on Mon Mar 31 18:29:42 GMT 2025
PRIMARY
CAS
76-57-3
Created by admin on Mon Mar 31 18:29:42 GMT 2025 , Edited by admin on Mon Mar 31 18:29:42 GMT 2025
PRIMARY
NCI_THESAURUS
C171855
Created by admin on Mon Mar 31 18:29:42 GMT 2025 , Edited by admin on Mon Mar 31 18:29:42 GMT 2025
ALTERNATIVE
ECHA (EC/EINECS)
200-969-1
Created by admin on Mon Mar 31 18:29:42 GMT 2025 , Edited by admin on Mon Mar 31 18:29:42 GMT 2025
PRIMARY
PUBCHEM
5284371
Created by admin on Mon Mar 31 18:29:42 GMT 2025 , Edited by admin on Mon Mar 31 18:29:42 GMT 2025
PRIMARY
MERCK INDEX
m3718
Created by admin on Mon Mar 31 18:29:42 GMT 2025 , Edited by admin on Mon Mar 31 18:29:42 GMT 2025
PRIMARY Merck Index
NCI_THESAURUS
C77284
Created by admin on Mon Mar 31 18:29:42 GMT 2025 , Edited by admin on Mon Mar 31 18:29:42 GMT 2025
PRIMARY
CHEBI
16714
Created by admin on Mon Mar 31 18:29:42 GMT 2025 , Edited by admin on Mon Mar 31 18:29:42 GMT 2025
PRIMARY
EPA CompTox
DTXSID2020341
Created by admin on Mon Mar 31 18:29:42 GMT 2025 , Edited by admin on Mon Mar 31 18:29:42 GMT 2025
PRIMARY
LEGACY_FDA_UNII
SS85U8K5ZN
Created by admin on Mon Mar 31 18:29:42 GMT 2025 , Edited by admin on Mon Mar 31 18:29:42 GMT 2025
PRIMARY
DAILYMED
UX6OWY2V7J
Created by admin on Mon Mar 31 18:29:42 GMT 2025 , Edited by admin on Mon Mar 31 18:29:42 GMT 2025
PRIMARY
RXCUI
236131
Created by admin on Mon Mar 31 18:29:42 GMT 2025 , Edited by admin on Mon Mar 31 18:29:42 GMT 2025
ALTERNATIVE
RXCUI
1545976
Created by admin on Mon Mar 31 18:29:42 GMT 2025 , Edited by admin on Mon Mar 31 18:29:42 GMT 2025
PRIMARY
HSDB
3043
Created by admin on Mon Mar 31 18:29:42 GMT 2025 , Edited by admin on Mon Mar 31 18:29:42 GMT 2025
PRIMARY
EVMPD
SUB127261
Created by admin on Mon Mar 31 18:29:42 GMT 2025 , Edited by admin on Mon Mar 31 18:29:42 GMT 2025
PRIMARY
EVMPD
SUB13424MIG
Created by admin on Mon Mar 31 18:29:42 GMT 2025 , Edited by admin on Mon Mar 31 18:29:42 GMT 2025
PRIMARY
FDA UNII
UX6OWY2V7J
Created by admin on Mon Mar 31 18:29:42 GMT 2025 , Edited by admin on Mon Mar 31 18:29:42 GMT 2025
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
BINDER->LIGAND
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SALT/SOLVATE -> PARENT
SOLVATE->ANHYDROUS
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
METABOLIC ENZYME -> SUBSTRATE
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