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
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
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.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL233 |
6.1 µM [EC50] | ||
Target ID: P41145 Gene ID: 4986.0 Gene Symbol: OPRK1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/7885194 |
|||
Target ID: P41143 Gene ID: 4985.0 Gene Symbol: OPRD1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/7885194 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | CAPITAL AND CODEINE Approved UseUnknown |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
66.9 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1391681/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7094509/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7094509/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7094509/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7094509/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1391681/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1391681/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1391681/ |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
0.61 μM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1391681/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7094509/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7094509/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7094509/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7094509/ |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1.47 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1391681/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7094509/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7094509/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7094509/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7094509/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1391681/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1391681/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1391681/ |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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 |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
inconclusive [IC50 35.7774 uM] | ||||
no | ||||
no | ||||
no | ||||
no | ||||
unlikely [IC50 400 uM] | ||||
yes [IC50 10.5 uM] |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 24.0 |
major | |||
Page: 20.0 |
major | |||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
Page: 20.0 |
yes | |||
Page: 20.0 |
yes | |||
yes | ||||
yes | ||||
yes |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
---|---|---|
Analgesic abuse, ureteric obstruction, and retroperitoneal fibrosis. | 1975 Apr 12 |
|
Determination of opiates in serum, saliva and hair addicted persons. | 2001 |
|
Saliva testing after single and chronic administration of dihydrocodeine. | 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 |
|
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 |
|
The diagnosis and treatment of cough. | 2001 Apr 5 |
|
Simultaneous determination of codeine and ethyl morphine HCL in tablet formulations using LC. | 2001 Aug |
|
[Paracetamol-codeine induced hepatic colic]. | 2001 Aug-Sep |
|
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 |
|
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 |
|
Heroin use by motorists in Sweden confirmed by analysis of 6-acetylmorphine in urine. | 2001 Jul-Aug |
|
[Chronic pain in geriatrics]. | 2001 Jun |
|
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 |
|
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 |
|
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 |
|
GC-MS determination of heroin metabolites in meconium: evaluation of four solid-phase extraction cartridges. | 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 |
|
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 |
|
Evaluation of urinary dihydrocodeine excretion in human by gas chromatography-mass spectrometry. | 2001 Mar 5 |
|
Dihydrocodeine--drug of use or misuse? | 2001 May |
|
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 |
|
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 |
|
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 |
|
Incorporation of selegiline metabolites into hair after oral selegiline intake. | 2001 Oct |
|
Spontaneous reports on drug-induced pancreatitis in Denmark from 1968 to 1999. | 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 |
|
[Strong opioids]. | 2001 Sep |
|
Concentration ratios of codeine-to-morphine in plasma after a single oral dose (100 mg) of codeine phosphate. | 2001 Sep |
|
Pain control in medical abortion. | 2001 Sep |
|
Can standard open pediatric urological procedures be performed on an outpatient basis? | 2001 Sep |
|
Experience with urine drug testing by the Correctional Service of Canada. | 2001 Sep 15 |
Sample Use Guides
In Vivo Use Guide
Sources: https://online.lexi.com/lco/medguides/622452.pdf
Unknown
Route of Administration:
Oral
Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 17:45:32 GMT 2025
by
admin
on
Mon Mar 31 17:45:32 GMT 2025
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Record UNII |
Q830PW7520
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Record Status |
Validated (UNII)
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Record Version |
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-
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Common Name | English | ||
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Preferred Name | English | ||
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Systematic Name | English | ||
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Systematic Name | English | ||
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Common Name | English | ||
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Common Name | English |
Classification Tree | Code System | Code | ||
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WHO-ATC |
N02AA79
Created by
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WHO-ATC |
N02AJ06
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WHO-ESSENTIAL MEDICINES LIST |
2.2
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WHO-VATC |
QN02AA79
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WHO-ATC |
N02AJ08
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CFR |
21 CFR 341.14
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CFR |
21 CFR 1308.15
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CFR |
21 CFR 341.74
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WHO-ATC |
N02AA59
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DEA NO. |
9050
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CFR |
21 CFR 290.2
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WHO-ATC |
R05DA04
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WHO-ATC |
N02AJ07
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NCI_THESAURUS |
C1657
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WHO-VATC |
QR05DA04
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NDF-RT |
N0000175690
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WHO-VATC |
QN02AA59
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LIVERTOX |
NBK548359
Created by
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Code System | Code | Type | Description | ||
---|---|---|---|---|---|
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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
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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. | ||
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1673
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PRIMARY | |||
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DTXSID20209391
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PRIMARY | |||
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CODEINE
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PRIMARY | |||
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CHEMBL485
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PRIMARY | |||
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SUB26908
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PRIMARY | |||
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C383
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PRIMARY | |||
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DB00318
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PRIMARY | |||
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16714
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PRIMARY | |||
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5362471
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PRIMARY | |||
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100000090266
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PRIMARY | |||
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SUB13424MIG
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PRIMARY | |||
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57871
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PRIMARY | |||
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Q830PW7520
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PRIMARY | |||
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Q830PW7520
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PRIMARY | |||
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D003061
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PRIMARY | |||
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2670
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PRIMARY | RxNorm | ||
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725
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PRIMARY | |||
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Codeine
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PRIMARY | |||
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6059-47-8
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PRIMARY |
Related Record | Type | Details | ||
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PARENT -> SALT/SOLVATE |
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ANHYDROUS->SOLVATE |
Related Record | Type | Details | ||
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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