U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C18H21NO3.H2O
Molecular Weight 317.3795
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CODEINE

SMILES

O.COC1=C2O[C@H]3[C@@H](O)C=C[C@H]4[C@H]5CC(C=C1)=C2[C@@]34CCN5C

InChI

InChIKey=WRRSFOZOETZUPG-FFHNEAJVSA-N
InChI=1S/C18H21NO3.H2O/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;1H2/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

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.

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
LC method for the analysis of paracetamol, caffeine and codeine phosphate in pharmaceutical preparations.
2001-12
The role of adrenal corticosteroids in induction of micronuclei by morphine.
2001-11-15
Nutritional effects of surgical and medical treatment for short bowel syndrome.
2001-11-02
Scalp nerve blocks decrease the severity of pain after craniotomy.
2001-11
Concentration ratios of morphine to codeine in blood of impaired drivers as evidence of heroin use and not medication with codeine.
2001-11
Endogenous morphine and codeine. Possible role as endogenous anticonvulsants.
2001-10-12
Drug contamination of US paper currency.
2001-10-01
Predictors for completing an inpatient detoxification program among intravenous heroin users, methadone substituted and codeine substituted patients.
2001-10-01
Novel dynamic polymer coating for capillary electrophoresis in nonaqueous methanolic background electrolytes.
2001-10
Seizures with intravenous codeine phosphate.
2001-10
Incorporation of selegiline metabolites into hair after oral selegiline intake.
2001-10
Analysis of morphine and codeine in samples adulterated with Stealth.
2001-10
Detection of opiate use in a methadone maintenance treatment population with the CEDIA 6-acetylmorphine and CEDIA DAU opiate assays.
2001-10
Ropivacaine with or without clonidine improves pediatric tonsillectomy pain.
2001-10
Experience with urine drug testing by the Correctional Service of Canada.
2001-09-15
Spontaneous reports on drug-induced pancreatitis in Denmark from 1968 to 1999.
2001-09
Community pharmacists' experience of over-the-counter medicine misuse in Scotland.
2001-09
Cetirizine inhibits skin reactions but not mediator release in immediate and developing late-phase allergic cutaneous reactions. A double-blind, placebo-controlled study.
2001-09
Rofecoxib versus codeine/acetaminophen in postoperative dental pain: a double-blind, randomized, placebo- and active comparator-controlled clinical trial.
2001-09
Tramadol/acetaminophen combination tablets and codeine/acetaminophen combination capsules for the management of chronic pain: a comparative trial.
2001-09
Blind trials of an onsite saliva drug test for marijuana and opiates.
2001-09
[Weak opioids].
2001-09
[Strong opioids].
2001-09
Concentration ratios of codeine-to-morphine in plasma after a single oral dose (100 mg) of codeine phosphate.
2001-09
Detection of non-prescription heroin markers in urine with liquid chromatography-atmospheric pressure chemical ionization mass spectrometry.
2001-09
Pain control in medical abortion.
2001-09
Engineering novel biocatalytic routes for production of semisynthetic opiate drugs.
2001-09
Can standard open pediatric urological procedures be performed on an outpatient basis?
2001-09
Precipitated withdrawal following codeine administration is dependent on CYP genotype.
2001-08-17
From codeine to transdermal fentanyl for cancer pain control: a safety and efficacy clinical trial.
2001-08-15
Heroin use by motorists in Sweden confirmed by analysis of 6-acetylmorphine in urine.
2001-08-14
Laboratory analysis of remotely collected oral fluid specimens for opiates by immunoassay.
2001-08-14
Prescribing limitations.
2001-08-11
[Paracetamol-codeine induced hepatic colic].
2001-08-02
Randomized placebo controlled trial of lofexidine hydrochloride for chronic pelvic pain in women.
2001-08
Simultaneous determination of codeine and ethyl morphine HCL in tablet formulations using LC.
2001-08
Sticky business: patterns of procurement and misuse of prescription cough syrup in Houston.
2001-07-31
Head-column field-amplified sample stacking in presence of siphoning. Application to capillary electrophoresis-electrospray ionization mass spectrometry of opioids in urine.
2001-07-27
Use of beta-cyclodextrin in the capillary zone electrophoretic separation of the components of clandestine heroin preparations.
2001-07-27
Opiate-sensitivity: clinical characteristics and the role of skin prick testing.
2001-07
Contribution of dihydrocodeine and dihydromorphine to analgesia following dihydrocodeine administration in man: a PK-PD modelling analysis.
2001-07
[Information on preparations containing codeine].
2001-06-20
[Chronic pain in geriatrics].
2001-06
Effect of apical trephination on postoperative pain and swelling in symptomatic necrotic teeth.
2001-06
Codeine phosphate in paediatric medicine.
2001-03
Codeine phosphate in children: time for re-evaluation?
2001-03
Effect of penicillin on postoperative endodontic pain and swelling in symptomatic necrotic teeth.
2001-02
Effect of prophylactic amoxicillin on endodontic flare-up in asymptomatic, necrotic teeth.
2001-01
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
Patents

Sample Use Guides

Unknown
Route of Administration: Oral
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:45:32 GMT 2025
Edited
by admin
on Mon Mar 31 17:45:32 GMT 2025
Record UNII
Q830PW7520
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CODEINE
EP   MART.   USP   VANDF  
Common Name English
CODEINE MONOHYDRATE
WHO-DD   WHO-IP  
Preferred Name English
LEAN
Common Name English
MORPHINAN-6-OL, 7,8-DIDEHYDRO-4,5-EPOXY-3-METHOXY-17-METHYL-, MONOHYDRATE, (5.ALPHA.,6.ALPHA.)-
Systematic Name English
CODEINUM
HPUS  
Common Name English
CODEINUM MONOHYDRICUM [WHO-IP LATIN]
Common Name English
CODEINE [MART.]
Common Name English
7,8-Didehydro-4,5?-epoxy-3-methoxy-17-methylmorphinan-6?-ol monohydrate
Systematic Name English
CODEINE [USP MONOGRAPH]
Common Name English
CODEINE MONOHYDRATE [EP MONOGRAPH]
Common Name English
DEA NO. 9050
Common Name English
CODEINE MONOHYDRATE [WHO-IP]
Common Name English
CODEINE [VANDF]
Common Name English
CODEINUM [HPUS]
Common Name English
Codeine monohydrate [WHO-DD]
Common Name English
Classification Tree Code System Code
WHO-ATC N02AA79
Created by admin on Mon Mar 31 17:45:32 GMT 2025 , Edited by admin on Mon Mar 31 17:45:32 GMT 2025
WHO-ATC N02AJ06
Created by admin on Mon Mar 31 17:45:32 GMT 2025 , Edited by admin on Mon Mar 31 17:45:32 GMT 2025
WHO-ESSENTIAL MEDICINES LIST 2.2
Created by admin on Mon Mar 31 17:45:32 GMT 2025 , Edited by admin on Mon Mar 31 17:45:32 GMT 2025
WHO-VATC QN02AA79
Created by admin on Mon Mar 31 17:45:32 GMT 2025 , Edited by admin on Mon Mar 31 17:45:32 GMT 2025
WHO-ATC N02AJ08
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CFR 21 CFR 341.14
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CFR 21 CFR 1308.15
Created by admin on Mon Mar 31 17:45:32 GMT 2025 , Edited by admin on Mon Mar 31 17:45:32 GMT 2025
CFR 21 CFR 341.74
Created by admin on Mon Mar 31 17:45:32 GMT 2025 , Edited by admin on Mon Mar 31 17:45:32 GMT 2025
WHO-ATC N02AA59
Created by admin on Mon Mar 31 17:45:32 GMT 2025 , Edited by admin on Mon Mar 31 17:45:32 GMT 2025
DEA NO. 9050
Created by admin on Mon Mar 31 17:45:32 GMT 2025 , Edited by admin on Mon Mar 31 17:45:32 GMT 2025
CFR 21 CFR 290.2
Created by admin on Mon Mar 31 17:45:32 GMT 2025 , Edited by admin on Mon Mar 31 17:45:32 GMT 2025
WHO-ATC R05DA04
Created by admin on Mon Mar 31 17:45:32 GMT 2025 , Edited by admin on Mon Mar 31 17:45:32 GMT 2025
WHO-ATC N02AJ07
Created by admin on Mon Mar 31 17:45:32 GMT 2025 , Edited by admin on Mon Mar 31 17:45:32 GMT 2025
NCI_THESAURUS C1657
Created by admin on Mon Mar 31 17:45:32 GMT 2025 , Edited by admin on Mon Mar 31 17:45:32 GMT 2025
WHO-VATC QR05DA04
Created by admin on Mon Mar 31 17:45:32 GMT 2025 , Edited by admin on Mon Mar 31 17:45:32 GMT 2025
NDF-RT N0000175690
Created by admin on Mon Mar 31 17:45:32 GMT 2025 , Edited by admin on Mon Mar 31 17:45:32 GMT 2025
WHO-VATC QN02AA59
Created by admin on Mon Mar 31 17:45:32 GMT 2025 , Edited by admin on Mon Mar 31 17:45:32 GMT 2025
LIVERTOX NBK548359
Created by admin on Mon Mar 31 17:45:32 GMT 2025 , Edited by admin on Mon Mar 31 17:45:32 GMT 2025
Code System Code Type Description
WHO INTERNATIONAL PHARMACOPEIA
CODEINE
Created by admin on Mon Mar 31 17:45:32 GMT 2025 , Edited by admin on Mon Mar 31 17:45:32 GMT 2025
PRIMARY Description: Colourless crystals or a white, crystalline powder; odourless.Solubility: Slightly soluble in water; freely soluble in ethanol (~750 g/l) TS and ether R.Category: Antitussive; analgesic.Storage: Codeine monohydrate should be kept in a tightly closed container, protected from light.Additional information: Codeine monohydrate effloresces slowly in dry air.
IUPHAR
1673
Created by admin on Mon Mar 31 17:45:32 GMT 2025 , Edited by admin on Mon Mar 31 17:45:32 GMT 2025
PRIMARY
EPA CompTox
DTXSID20209391
Created by admin on Mon Mar 31 17:45:32 GMT 2025 , Edited by admin on Mon Mar 31 17:45:32 GMT 2025
PRIMARY
WIKIPEDIA
CODEINE
Created by admin on Mon Mar 31 17:45:32 GMT 2025 , Edited by admin on Mon Mar 31 17:45:32 GMT 2025
PRIMARY
ChEMBL
CHEMBL485
Created by admin on Mon Mar 31 17:45:32 GMT 2025 , Edited by admin on Mon Mar 31 17:45:32 GMT 2025
PRIMARY
EVMPD
SUB26908
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PRIMARY
NCI_THESAURUS
C383
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PRIMARY
DRUG BANK
DB00318
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PRIMARY
CHEBI
16714
Created by admin on Mon Mar 31 17:45:32 GMT 2025 , Edited by admin on Mon Mar 31 17:45:32 GMT 2025
PRIMARY
PUBCHEM
5362471
Created by admin on Mon Mar 31 17:45:32 GMT 2025 , Edited by admin on Mon Mar 31 17:45:32 GMT 2025
PRIMARY
SMS_ID
100000090266
Created by admin on Mon Mar 31 17:45:32 GMT 2025 , Edited by admin on Mon Mar 31 17:45:32 GMT 2025
PRIMARY
EVMPD
SUB13424MIG
Created by admin on Mon Mar 31 17:45:32 GMT 2025 , Edited by admin on Mon Mar 31 17:45:32 GMT 2025
PRIMARY
CHEBI
57871
Created by admin on Mon Mar 31 17:45:32 GMT 2025 , Edited by admin on Mon Mar 31 17:45:32 GMT 2025
PRIMARY
DAILYMED
Q830PW7520
Created by admin on Mon Mar 31 17:45:32 GMT 2025 , Edited by admin on Mon Mar 31 17:45:32 GMT 2025
PRIMARY
FDA UNII
Q830PW7520
Created by admin on Mon Mar 31 17:45:32 GMT 2025 , Edited by admin on Mon Mar 31 17:45:32 GMT 2025
PRIMARY
MESH
D003061
Created by admin on Mon Mar 31 17:45:32 GMT 2025 , Edited by admin on Mon Mar 31 17:45:32 GMT 2025
PRIMARY
RXCUI
2670
Created by admin on Mon Mar 31 17:45:32 GMT 2025 , Edited by admin on Mon Mar 31 17:45:32 GMT 2025
PRIMARY RxNorm
DRUG CENTRAL
725
Created by admin on Mon Mar 31 17:45:32 GMT 2025 , Edited by admin on Mon Mar 31 17:45:32 GMT 2025
PRIMARY
LACTMED
Codeine
Created by admin on Mon Mar 31 17:45:32 GMT 2025 , Edited by admin on Mon Mar 31 17:45:32 GMT 2025
PRIMARY
CAS
6059-47-8
Created by admin on Mon Mar 31 17:45:32 GMT 2025 , Edited by admin on Mon Mar 31 17:45:32 GMT 2025
PRIMARY
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