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

Sample Use Guides

Unknown
Route of Administration: Oral
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
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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