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Details

Stereochemistry ABSOLUTE
Molecular Formula 2C18H21NO3.3H2O.2H3O4P
Molecular Weight 848.7647
Optical Activity UNSPECIFIED
Defined Stereocenters 10 / 10
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CODEINE PHOSPHATE SESQUIHYDRATE

SMILES

O.O.O.OP(O)(O)=O.OP(O)(O)=O.[H][C@@]12OC3=C4C(C[C@H]5N(C)CC[C@@]14[C@@]5([H])C=C[C@@H]2O)=CC=C3OC.[H][C@@]67OC8=C9C(C[C@H]%10N(C)CC[C@@]69[C@@]%10([H])C=C[C@@H]7O)=CC=C8OC

InChI

InChIKey=UDIMULCGRYVAIM-REWFBLHLSA-N
InChI=1S/2C18H21NO3.2H3O4P.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;2*1-5(2,3)4;;;/h2*3-6,11-13,17,20H,7-9H2,1-2H3;2*(H3,1,2,3,4);3*1H2/t2*11-,12+,13-,17-,18-;;;;;/m00...../s1

HIDE SMILES / InChI

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

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 H3O4P
Molecular Weight 97.9952
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
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Codeine analgesia is due to codeine-6-glucuronide, not morphine.
2000 Jul-Aug
[Pharmacokinetic and toxicokinetic parameters of some drugs of abuse].
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
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
LC method for the analysis of acetylsalicylic acid, caffeine and codeine phosphate in pharmaceutical preparations.
2001 Apr
[Adverse cutaneous side-effect of codeine administration].
2001 Apr 15
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
Effect of penicillin on postoperative endodontic pain and swelling in symptomatic necrotic teeth.
2001 Feb
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
No pain relief from codeine...? An introduction to pharmacogenomics.
2001 Feb
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
Contribution of dihydrocodeine and dihydromorphine to analgesia following dihydrocodeine administration in man: a PK-PD modelling analysis.
2001 Jul
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
Are cannabinoids an effective and safe treatment option in the management of pain? A qualitative systematic review.
2001 Jul 7
Oral ibuprofen versus paracetamol plus codeine for analgesia after ambulatory surgery.
2001 Jun
Time of drug elimination in chronic drug abusers. Case study of 52 patients in a "low-step" detoxification ward.
2001 Jun 15
[Information on preparations containing codeine].
2001 Jun 20
Expression and activity of cell-wall-degrading enzymes in the latex of opium poppy, Papaver somniferum L.
2001 Mar
Acetylcodeine as a marker of illicit heroin in human hair: method validation and results of a pilot study.
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
Effect of an enteric-release formulation of naloxone on intestinal transit in volunteers taking codeine.
2001 May
[Analgesics-induced chronic renal failure in patients on dialysis therapy in Hungary].
2001 May 13
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
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
Seizures with intravenous codeine phosphate.
2001 Oct
Incorporation of selegiline metabolites into hair after oral selegiline intake.
2001 Oct
Ropivacaine with or without clonidine improves pediatric tonsillectomy pain.
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
Pain control in medical abortion.
2001 Sep
Engineering novel biocatalytic routes for production of semisynthetic opiate drugs.
2001 Sep
Patents

Sample Use Guides

Unknown
Route of Administration: Oral
Substance Class Chemical
Created
by admin
on Fri Dec 15 18:14:25 GMT 2023
Edited
by admin
on Fri Dec 15 18:14:25 GMT 2023
Record UNII
BKA0632GWS
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CODEINE PHOSPHATE SESQUIHYDRATE
EP   WHO-DD   WHO-IP  
Common Name English
CODEINE PHOSPHATE SESQUIHYDRATE [EP MONOGRAPH]
Common Name English
7,8-DIDEHYDRO-4,5.ALPHA.-EPOXY-3-METHOXY-17-METHYLMORPHINAN-6.ALPHA.-OL PHOSPHATE SESQUIHYDRATE
Common Name English
Codeine phosphate sesquihydrate [WHO-DD]
Common Name English
CODEINE PHOSPHATE SESQUIHYDRATE [WHO-IP]
Common Name English
Code System Code Type Description
CAS
5913-76-8
Created by admin on Fri Dec 15 18:14:25 GMT 2023 , Edited by admin on Fri Dec 15 18:14:25 GMT 2023
PRIMARY
FDA UNII
BKA0632GWS
Created by admin on Fri Dec 15 18:14:25 GMT 2023 , Edited by admin on Fri Dec 15 18:14:25 GMT 2023
PRIMARY
EPA CompTox
DTXSID20207872
Created by admin on Fri Dec 15 18:14:25 GMT 2023 , Edited by admin on Fri Dec 15 18:14:25 GMT 2023
PRIMARY
SMS_ID
100000092021
Created by admin on Fri Dec 15 18:14:25 GMT 2023 , Edited by admin on Fri Dec 15 18:14:25 GMT 2023
PRIMARY
PUBCHEM
5492885
Created by admin on Fri Dec 15 18:14:25 GMT 2023 , Edited by admin on Fri Dec 15 18:14:25 GMT 2023
PRIMARY
EVMPD
SUB01408MIG
Created by admin on Fri Dec 15 18:14:25 GMT 2023 , Edited by admin on Fri Dec 15 18:14:25 GMT 2023
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
CODEINE PHOSPHATE SESQUIHYDRATE
Created by admin on Fri Dec 15 18:14:25 GMT 2023 , Edited by admin on Fri Dec 15 18:14:25 GMT 2023
PRIMARY Description: Small, colourless crystals or a white, crystalline powder; odourless.Solubility: Soluble in 4 parts of water; slightly soluble in ethanol (~750 g/l) TS; practically insoluble in ether R.Category: Antitussive; analgesic.Storage: Codeine phosphate should be kept in a tightly closed container, protected from light.Labelling: The designation on the container should state if the Codeine phosphate is the hemihydrate or the sesquihydrate.Additional information: Codeine phosphate effloresces in dry air.
Related Record Type Details
PARENT -> SALT/SOLVATE
ANHYDROUS->SOLVATE
Related Record Type Details
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
Pending
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
correction factor: for the calculation of content, multiply the peak area of impurity C by 0.25
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
ACTIVE MOIETY