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 2C18H21NO3.3H2O.H2O4S
Molecular Weight 750.853
Optical Activity UNSPECIFIED
Defined Stereocenters 10 / 10
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CODEINE SULFATE

SMILES

O.O.O.OS(O)(=O)=O.COC1=C2O[C@H]3[C@@H](O)C=C[C@H]4[C@H]5CC(C=C1)=C2[C@@]34CCN5C.COC6=C7O[C@H]8[C@@H](O)C=C[C@H]9[C@H]%10CC(C=C6)=C7[C@@]89CCN%10C

InChI

InChIKey=BOLDZXRCJAJADM-AAXBYHQXSA-N
InChI=1S/2C18H21NO3.H2O4S.3H2O/c2*1-19-8-7-18-11-4-5-13(20)17(18)22-16-14(21-2)6-3-10(15(16)18)9-12(11)19;1-5(2,3)4;;;/h2*3-6,11-13,17,20H,7-9H2,1-2H3;(H2,1,2,3,4);3*1H2/t2*11-,12+,13-,17-,18-;;;;/m00..../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
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
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
Saliva testing after single and chronic administration of dihydrocodeine.
2001
Pharmacological control of cough.
2001 Apr
The use of compound 48/80 and codeine phosphate as positive controls for intradermal skin testing in dogs.
2001 Apr
Simultaneous determination of codeine and ethyl morphine HCL in tablet formulations using LC.
2001 Aug
LC method for the analysis of paracetamol, caffeine and codeine phosphate in pharmaceutical preparations.
2001 Dec
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
Dose-related effects of controlled release dihydrocodeine on oro-cecal transit and pupillary light reflex. A study in human volunteers.
2001 Jan
Opiate-sensitivity: clinical characteristics and the role of skin prick testing.
2001 Jul
Use of beta-cyclodextrin in the capillary zone electrophoretic separation of the components of clandestine heroin preparations.
2001 Jul 27
Are cannabinoids an effective and safe treatment option in the management of pain? A qualitative systematic review.
2001 Jul 7
[Chronic pain in geriatrics].
2001 Jun
Codeine phosphate in paediatric medicine.
2001 Mar
Codeine phosphate in children: time for re-evaluation?
2001 Mar
Myocardial Infarction associated with methadone and/or dihydrocodeine.
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
Acetylcodeine as a marker of illicit heroin in human hair: method validation and results of a pilot study.
2001 Mar
Opiate use to control bowel motility may induce chronic daily headache in patients with migraine.
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
Evaluation of urinary dihydrocodeine excretion in human by gas chromatography-mass spectrometry.
2001 Mar 5
Dihydrocodeine--drug of use or misuse?
2001 May
[Analgesics-induced chronic renal failure in patients on dialysis therapy in Hungary].
2001 May 13
Scalp nerve blocks decrease the severity of pain after craniotomy.
2001 Nov
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
Seizures with intravenous codeine phosphate.
2001 Oct
Incorporation of selegiline metabolites into hair after oral selegiline intake.
2001 Oct
Analysis of morphine and codeine in samples adulterated with Stealth.
2001 Oct
Detection of opiate use in a methadone maintenance treatment population with the CEDIA 6-acetylmorphine and CEDIA DAU opiate assays.
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
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
Tramadol/acetaminophen combination tablets and codeine/acetaminophen combination capsules for the management of chronic pain: a comparative trial.
2001 Sep
Blind trials of an onsite saliva drug test for marijuana and opiates.
2001 Sep
[Weak opioids].
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
Detection of non-prescription heroin markers in urine with liquid chromatography-atmospheric pressure chemical ionization mass spectrometry.
2001 Sep
Pain control in medical abortion.
2001 Sep
Can standard open pediatric urological procedures be performed on an outpatient basis?
2001 Sep
Patents

Sample Use Guides

Unknown
Route of Administration: Oral
Name Type Language
CODEINE SULFATE
USP  
Official Name English
CODEINE SULFATE [VANDF]
Preferred Name English
Morphinan-6-ol, 7,8-didehydro-4,5-epoxy-3-methoxy-17-methyl-, (5?,6?)-, sulfate (2:1) (salt), trihydrate
Systematic Name English
Codeine sulfate trihydrate
Common Name English
Dicodeine monosulfate trihydrate
Common Name English
CODEINE SULFATE [USP-RS]
Common Name English
Codeine sulfate [WHO-DD]
Common Name English
Morphinan-6?-ol, 7,8-didehydro-4,5?-epoxy-3-methoxy-17-methyl-, sulfate (2:1) salt, trihydrate
Systematic Name English
7,8-Didehydro-4,5?-epoxy-3-methoxy-17-methylmorphinan-6?-ol sulfate (2:1) (salt) trihydrate
Common Name English
CODEINE SULFATE [USP MONOGRAPH]
Common Name English
CODEINE SULFATE [MART.]
Common Name English
CODEINE SULFATE [ORANGE BOOK]
Common Name English
Codeine hemisulfate sesquihydrate
Common Name English
CODEINE SULPHATE
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C1657
Created by admin on Mon Mar 31 17:36:57 GMT 2025 , Edited by admin on Mon Mar 31 17:36:57 GMT 2025
CFR 21 CFR 341.74
Created by admin on Mon Mar 31 17:36:57 GMT 2025 , Edited by admin on Mon Mar 31 17:36:57 GMT 2025
CFR 21 CFR 1308.15
Created by admin on Mon Mar 31 17:36:57 GMT 2025 , Edited by admin on Mon Mar 31 17:36:57 GMT 2025
CFR 21 CFR 290.2
Created by admin on Mon Mar 31 17:36:57 GMT 2025 , Edited by admin on Mon Mar 31 17:36:57 GMT 2025
CFR 21 CFR 341.14
Created by admin on Mon Mar 31 17:36:57 GMT 2025 , Edited by admin on Mon Mar 31 17:36:57 GMT 2025
Code System Code Type Description
SMS_ID
100000087978
Created by admin on Mon Mar 31 17:36:57 GMT 2025 , Edited by admin on Mon Mar 31 17:36:57 GMT 2025
PRIMARY
ChEMBL
CHEMBL485
Created by admin on Mon Mar 31 17:36:57 GMT 2025 , Edited by admin on Mon Mar 31 17:36:57 GMT 2025
PRIMARY
EPA CompTox
DTXSID50218658
Created by admin on Mon Mar 31 17:36:57 GMT 2025 , Edited by admin on Mon Mar 31 17:36:57 GMT 2025
PRIMARY
FDA UNII
11QV9BS0CB
Created by admin on Mon Mar 31 17:36:57 GMT 2025 , Edited by admin on Mon Mar 31 17:36:57 GMT 2025
PRIMARY
DRUG BANK
DBSALT001843
Created by admin on Mon Mar 31 17:36:57 GMT 2025 , Edited by admin on Mon Mar 31 17:36:57 GMT 2025
PRIMARY
RS_ITEM_NUM
1145003
Created by admin on Mon Mar 31 17:36:57 GMT 2025 , Edited by admin on Mon Mar 31 17:36:57 GMT 2025
PRIMARY
DAILYMED
11QV9BS0CB
Created by admin on Mon Mar 31 17:36:57 GMT 2025 , Edited by admin on Mon Mar 31 17:36:57 GMT 2025
PRIMARY
NCI_THESAURUS
C53137
Created by admin on Mon Mar 31 17:36:57 GMT 2025 , Edited by admin on Mon Mar 31 17:36:57 GMT 2025
PRIMARY
CAS
6854-40-6
Created by admin on Mon Mar 31 17:36:57 GMT 2025 , Edited by admin on Mon Mar 31 17:36:57 GMT 2025
PRIMARY
PUBCHEM
21155870
Created by admin on Mon Mar 31 17:36:57 GMT 2025 , Edited by admin on Mon Mar 31 17:36:57 GMT 2025
PRIMARY
EVMPD
SUB01410MIG
Created by admin on Mon Mar 31 17:36:57 GMT 2025 , Edited by admin on Mon Mar 31 17:36:57 GMT 2025
PRIMARY
RXCUI
91104
Created by admin on Mon Mar 31 17:36:57 GMT 2025 , Edited by admin on Mon Mar 31 17:36:57 GMT 2025
PRIMARY RxNorm