Identification
- Summary
Codeine is an opioid analgesic used to treat moderate to severe pain when the use of an opioid is indicated.
- Brand Names
- Ascomp, Cheratussin, Cheratussin Dac, Codar Ar, Codar D, Codar Gf, Codeine Contin, Covan, Damylin With Codeine, Fioricet With Codeine, Histex Ac, Linctus Codeine Blanc, M-clear Wc, M-end PE, Mar-cof BP, Mar-cof Cg, Mersyndol, Ninjacof Xg, Pseudodine C, Robaxacet-8, Robaxisal, Triacin-C, Trianal C, Triatec, Triatec-30, Triatec-8, Tusnel C, Tuxarin, Tuzistra, Tylenol With Codeine
- Generic Name
- Codeine
- DrugBank Accession Number
- DB00318
- Background
The relief of pain (analgesia) is a primary goal for enhancing the quality of life of patients and for increasing the ability of patients to engage in day to day activities. Codeine, an opioid analgesic, was originally approved in the US in 1950 and is a drug used to decrease pain by increasing the threshold for pain without impairing consciousness or altering other sensory functions. Opiates such as codeine are derived from the poppy plant, Papaver somniferum (Papaveraceae).4
Codeine is utilized as a central analgesic, sedative, hypnotic, antinociceptive, and antiperistaltic agent, and is also recommended in certain diseases with incessant coughing.Label,4
- Type
- Small Molecule
- Groups
- Approved, Illicit
- Structure
Structure for Codeine (DB00318)
- Weight
- Average: 299.3642
Monoisotopic: 299.152143543 - Chemical Formula
- C18H21NO3
- Synonyms
- (−)-Codeine
- (5alpha,6alpha)-7,8-Didehydro-4,5-epoxy-3-methoxy-17-methylmorphinan-6-ol
- 7,8-didehydro-4,5α-epoxy-3-methoxy-17-methylmorphinan-6α-ol
- Codein
- Codeína
- Codéine
- Codeine anhydrous
- Codeine polistirex
- Codeinum
- L-Codeine
- Methylmorphine
- morphine 3-methyl ether
- Morphine monomethyl ether
- morphine-3-methyl ether
- O3-Methylmorphine
- External IDs
- IDS-NC-005(SECT.-2)
Pharmacology
- Indication
Codeine sulfate is a form of this drug that is commonly used. It is available in tablet form Label and indicated for the relief of mild to moderately severe pain, where the use of an opioid analgesic is appropriate Label.
The solution form is used by itself or combined in a syrup with other drugs and is used as a cough suppressant in adults aged 18 and above 14, 15.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Used in combination for symptomatic treatment of Common cold Combination Product in combination with: Chlorpheniramine (DB01114), Acetaminophen (DB00316) ••• ••• ••••••• Treatment of Cough •••••••••••• Used in combination to treat Coughing Combination Product in combination with: Thiocolchicoside (DB11582), Ephedrine (DB01364), Sodium citrate (DB09154) •••••••••••• ••••• Used in combination for symptomatic treatment of Flu caused by influenza Combination Product in combination with: Chlorpheniramine (DB01114), Acetaminophen (DB00316) ••• ••• ••••••• Treatment of Mild pain •••••••••••• - Associated Therapies
- Contraindications & Blackbox Warnings
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General effects
Codeine is a weak narcotic pain reliever and cough suppressant that is similar to morphine and hydrocodone. A small amount of ingested codeine is converted to morphine in the body. Codeine increases tolerance to pain, reducing existing discomfort. In addition to decreasing pain, codeine also causes sedation, drowsiness, and respiratory depression 4.
Antitussive activity
This drug has shown antitussive activity in clinical trials 6 and has been effective in cough secondary to tuberculosis and insomnia due to coughing 4. Codeine suppresses the cough reflex through a direct effect on the cough center in the medulla 18.
Effects on intestinal motility
Codeine may reduce intestinal motility through both a local and possibly central mechanism of action 19. This may possibly lead to constipation 18. The chronic use of opioids, including codeine sulfate, may lead to obstructive bowel disease, particularly in patients with underlying disorders of intestinal motility Label.
Effects on the central nervous system
Codeine phosphate is an opioid analgesic with uses similar to those of morphine, but is much less potent as an analgesic. Its primary site of action is at the mu opioid receptors distributed throughout the central nervous system. The sedative activities of codeine are less potent than those of morphine 18. Codeine may cause respiratory system depression by the activation of μ-opioid receptors at specific sites in the central nervous system 8.
Effects on blood pressure
This drug poses an increased risk of compromised ability to maintain blood pressure due to peripheral vasodilation and other mechanisms Label.
Effects on chronic cancer pain and other types of pain
Codeine is an opioid analgesic with similar indications to those of morphine, however, is much less potent in its pain alleviating properties. Its primary action takes place at the mu opioid receptors, which are distributed throughout the central nervous system. The average duration of action is about 4 hours 18.
Regular dosing of opioid analgesics such as codeine in patients with severe cancer pain has been well documented to improve symptoms 4, 7.
- Mechanism of action
Although the exact mechanism of action of codeine is still unknown, it is generally thought to be mediated through the agonism of opioid receptors, particularly the mu-opioid receptors.4 Morphine was previously postulated to contribute to the analgesic effect of codeine due to the O-demethylation of codeine to morphine by CYP2D6. Particularly, CYP2D6 poor metabolizer did not experience the analgesic effect of codeine.2,10 However, this is unlikely to be the main mechanism of action of codeine as only 5% of codeine is metabolized to morphine.2 Other hypotheses also postulate that codeine-6-glucuronide, the main metabolite of codeine, mediates the analgesic effect of codeine as it not only has an affinity to the mu receptors as codeine but also can be metabolized to morphine-6-glucuronide, which was observed to be more potent than morphine.3
Binding to the mu receptors by codeine activates the G-proteins Gαi, causing a decrease in intracellular cAMP and Ca2+ level.11,12 This causes hyperpolarization of nociceptive neurons, thus imparing the transmission of pain signals.11,12
Target Actions Organism AMu-type opioid receptor agonistregulatorHumans AKappa-type opioid receptor agonistHumans ADelta-type opioid receptor agonistHumans - Absorption
Absorption
Codeine is absorbed from the gastrointestinal tract. The maximum plasma concentration occurs 60 minutes after administration Label.
Food Effects
When 60 mg codeine sulfate was given 30 minutes post-ingestion of a high high-calorie meal, there was no significant change in the absorption of codeine Label.
Steady-state concentration
The administration of 15 mg codeine sulfate every 4 hours for 5 days lead to steady-state concentrations of codeine, morphine, morphine-3-glucuronide (M3G) and morphine-6-glucuronide (M6G) within 48 hours Label.
- Volume of distribution
Apparent volume of distribution: about 3-6 L/kg, showing an extensive distribution of the drug into tissues Label.
- Protein binding
7-25% bound to plasma proteins Label.
- Metabolism
Approximately 70 to 80% of the ingested dose of codeine is metabolized in the liver by conjugation with glucuronic acid to codeine-6 glucuronide (C6G) and by O-demethylation to morphine (about 5-10%) and N-demethylation to norcodeine (about 10%) respectively. UDP-glucuronosyltransferase (UGT) 2B7 and 2B4 are the major metabolic enzymes mediating the glucurodination of codeine to the metabolite, codeine 6 glucuronide.
Cytochrome P450 2D6 is the major enzyme responsible for the transformation of codeine to morphine and P450 3A4 is the main enzyme mediating the conversion of codeine to norcodeine. Morphine and norcodeine are then further metabolized by conjugation with glucuronic acid. The glucuronide metabolites of morphine are morphine-3-glucuronide (M3G) and_ morphine-6-glucuronide _(M6G). Morphine and M6G have been proven to have analgesic activity in humans. The analgesic activity of C6G in humans is not known at this time. Norcodeine and M3G are generally not considered to have analgesic properties Label.
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- Route of elimination
About 90% of the total dose of codeine is excreted by the kidneys. Approximately 10% of the drug excreted by the kidneys is unchanged codeine Label.
The majority of the excretion products can be found in the urine within 6 hours of ingestion, and 40-60 % of the codeine is excreted free or conjugated, approximately 5 to 15 percent as free and conjugated morphine, and approximately 10-20% free and conjugated norcodeine 18.
- Half-life
Plasma half-lives of codeine and its metabolites have been reported to be approximately 3 hours Label.
- Clearance
Renal clearance of codeine was 183 +/- 59 ml min-1 in a clinical study 5.
Renal impairment may decrease codeine clearance Label.
- Adverse Effects
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Oral LD50: 427 mg kg-1 (rat) MSDS.
Overdose/toxicity
Symptoms of opioid toxicity may include confusion, somnolence, shallow breathing, constricted pupils, nausea, vomiting, constipation and a lack of appetite. In severe cases, symptoms of circulatory and respiratory depression may ensue, which may be life-threatening or fatal 13, Label.
Teratogenic effects
This drug is classified as a pregnancy Category C drug. There are no adequate and well-controlled studies completed in pregnant women. Codeine should only be used during pregnancy if the potential benefit outweighs the potential risk of the drug to the fetus Label.
Codeine has shown embryolethal and fetotoxic effects in the hamster, rat as well as mouse models at about 2-4 times the maximum recommended human dose Label. Maternally toxic doses that were about 7 times the maximum recommended human dose of 360 mg/day, were associated with evidence of bone resorption and incomplete bone ossification. Codeine did not demonstrate evidence of embrytoxicity or fetotoxicity in the rabbit model at doses up to 2 times the maximum recommended human dose of 360 mg/day based on a body surface area comparison Label.
Nonteratogenic effects
Neonatal codeine withdrawal has been observed in infants born to addicted and non-addicted mothers who ingested codeine-containing medications in the days before delivery. Common symptoms of narcotic withdrawal include irritability, excessive crying, tremors, hyperreflexia, seizures, fever, vomiting, diarrhea, and poor feeding. These signs may be observed shortly following birth and may require specific treatment Label.
Codeine (30 mg/kg) given subcutaneously to pregnant rats during gestation and for 25 days after delivery increased the rate of neonatal mortality at birth. The dose given was 0.8 times the maximum recommended human dose of 360 mg/day Label.
The use in breastfeeding/nursing
Codeine is secreted into human milk. The maternal use of codeine can potentially lead to serious adverse reactions, including death, in nursing infants Label.
- Pathways
Pathway Category Codeine Metabolism Pathway Drug metabolism Codeine Action Pathway Drug action - Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Interacting Gene/Enzyme Allele name Genotype(s) Defining Change(s) Type(s) Description Details Cytochrome P450 2D6 CYP2D6*4 (A;A) A Allele, homozygote Effect Directly Studied Patients with this genotype have reduced metabolism of codeine. Details Cytochrome P450 2D6 CYP2D6*6 (-;-) T deletion, homozygote Effect Directly Studied Patients with this genotype have reduced metabolism of codeine. Details Cytochrome P450 2D6 CYP2D6*5 Not Available Whole gene deletion, homozygote Effect Directly Studied Patients with this genotype have reduced metabolism of codeine. Details Cytochrome P450 2D6 CYP2D6*3 Not Available 2549delA Effect Directly Studied The presence of this polymorphism in CYP2D6 results in non-functioning enzyme variant and may be associated with reduced drug mtabolism or reduced therapeutic response when treated with codeine. Details Cytochrome P450 2D6 CYP2D6*4 Not Available A allele Effect Directly Studied The presence of this polymorphism in CYP2D6 is associated with poor metabolism of codeine. Details Cytochrome P450 2D6 CYP2D6*5 Not Available Whole-gene deletion Effect Directly Studied The presence of this polymorphism in CYP2D6 is associated with poor metabolism of codeine and lack of therapeutic response from codeine. Details Cytochrome P450 2D6 CYP2D6*6 (-;T) / (-;-) 1707delT Effect Directly Studied The presence of this polymorphism in CYP2D6 is associated with poor metabolism of codeine. Details Cytochrome P450 2D6 CYP2D6*7 Not Available 2935A>C Effect Inferred Poor drug metabolizer. Lack of efficacy. For individual with two non-functional alleles, alternative drug recommended. Details Cytochrome P450 2D6 CYP2D6*8 Not Available 1758G>T Effect Inferred Poor drug metabolizer. Lack of efficacy. For individual with two non-functional alleles, alternative drug recommended. Details Cytochrome P450 2D6 CYP2D6*11 Not Available 883G>C Effect Inferred Poor drug metabolizer. Lack of efficacy. For individual with two non-functional alleles, alternative drug recommended. Details Cytochrome P450 2D6 CYP2D6*12 Not Available 124G>A Effect Inferred Poor drug metabolizer. Lack of efficacy. For individual with two non-functional alleles, alternative drug recommended. Details Cytochrome P450 2D6 CYP2D6*13 Not Available CYP2D7/2D6 hybrid gene structure Effect Inferred Poor drug metabolizer. Lack of efficacy. For individual with two non-functional alleles, alternative drug recommended. Details Cytochrome P450 2D6 CYP2D6*14A Not Available 1758G>A Effect Inferred Poor drug metabolizer. Lack of efficacy. For individual with two non-functional alleles, alternative drug recommended. Details Cytochrome P450 2D6 CYP2D6*15 Not Available 137insT, 137_138insT Effect Inferred Poor drug metabolizer. Lack of efficacy. For individual with two non-functional alleles, alternative drug recommended. Details Cytochrome P450 2D6 CYP2D6*19 Not Available 2539_2542delAACT Effect Inferred Poor drug metabolizer. Lack of efficacy. For individual with two non-functional alleles, alternative drug recommended. Details Cytochrome P450 2D6 CYP2D6*20 Not Available 1973_1974insG Effect Inferred Poor drug metabolizer. Lack of efficacy. For individual with two non-functional alleles, alternative drug recommended. Details Cytochrome P450 2D6 CYP2D6*21 Not Available 2573insC Effect Inferred Poor drug metabolizer. Lack of efficacy. For individual with two non-functional alleles, alternative drug recommended. Details Cytochrome P450 2D6 CYP2D6*31 Not Available -1770G>A / -1584C>G … show all Effect Inferred Poor drug metabolizer. Lack of efficacy. For individual with two non-functional alleles, alternative drug recommended. Details Cytochrome P450 2D6 CYP2D6*36 Not Available 100C>T / -1426C>T … show all Effect Inferred Poor drug metabolizer. Lack of efficacy. For individual with two non-functional alleles, alternative drug recommended. Details Cytochrome P450 2D6 CYP2D6*38 Not Available 2587_2590delGACT Effect Inferred Poor drug metabolizer. Lack of efficacy. For individual with two non-functional alleles, alternative drug recommended. Details Cytochrome P450 2D6 CYP2D6*40 Not Available 1863_1864ins(TTT CGC CCC)2 Effect Inferred Poor drug metabolizer. Lack of efficacy. For individual with two non-functional alleles, alternative drug recommended. Details Cytochrome P450 2D6 CYP2D6*42 Not Available 3259_3260insGT Effect Inferred Poor drug metabolizer. Lack of efficacy. For individual with two non-functional alleles, alternative drug recommended. Details Cytochrome P450 2D6 CYP2D6*44 Not Available 2950G>C Effect Inferred Poor drug metabolizer. Lack of efficacy. For individual with two non-functional alleles, alternative drug recommended. Details Cytochrome P450 2D6 CYP2D6*47 Not Available 100C>T / -1426C>T … show all Effect Inferred Poor drug metabolizer. Lack of efficacy. For individual with two non-functional alleles, alternative drug recommended. Details Cytochrome P450 2D6 CYP2D6*51 Not Available -1584C>G / -1235A>G … show all Effect Inferred Poor drug metabolizer. Lack of efficacy. For individual with two non-functional alleles, alternative drug recommended. Details Cytochrome P450 2D6 CYP2D6*56 Not Available 3201C>T Effect Inferred Poor drug metabolizer. Lack of efficacy. For individual with two non-functional alleles, alternative drug recommended. Details Cytochrome P450 2D6 CYP2D6*57 Not Available 100C>T / 310G>T … show all Effect Inferred Poor drug metabolizer. Lack of efficacy. For individual with two non-functional alleles, alternative drug recommended. Details Cytochrome P450 2D6 CYP2D6*62 Not Available 4044C>T Effect Inferred Poor drug metabolizer. Lack of efficacy. For individual with two non-functional alleles, alternative drug recommended. Details Cytochrome P450 2D6 CYP2D6*68A Not Available -1426C>T / -1235A>G … show all Effect Inferred Poor drug metabolizer. Lack of efficacy. For individual with two non-functional alleles, alternative drug recommended. Details Cytochrome P450 2D6 CYP2D6*68B Not Available Similar but not identical switch region compared to CYP2D6*68A. Found in tandem arrangement with CYP2D6*4. Effect Inferred Poor drug metabolizer. Lack of efficacy. For individual with two non-functional alleles, alternative drug recommended. Details Cytochrome P450 2D6 CYP2D6*69 Not Available 2988G>A / -1426C>T … show all Effect Inferred Poor drug metabolizer. Lack of efficacy. For individual with two non-functional alleles, alternative drug recommended. Details Cytochrome P450 2D6 CYP2D6*92 Not Available 1995delC Effect Inferred Poor drug metabolizer. Lack of efficacy. For individual with two non-functional alleles, alternative drug recommended. Details Cytochrome P450 2D6 CYP2D6*100 Not Available -1426C>T / -1235A>G … show all Effect Inferred Poor drug metabolizer. Lack of efficacy. For individual with two non-functional alleles, alternative drug recommended. Details Cytochrome P450 2D6 CYP2D6*101 Not Available -1426C>T / -1235A>G … show all Effect Inferred Poor drug metabolizer. Lack of efficacy. For individual with two non-functional alleles, alternative drug recommended. Details Cytochrome P450 2D6 CYP2D6*1XN Not Available Normal allele duplicated. ADR Inferred Ultra-rapid drug metabolizer. Risk of toxicity, alternative drug recommended. Details Cytochrome P450 2D6 CYP2D6*2XN Not Available 2850C>T / 4180G>C … show all ADR Inferred Ultra-rapid drug metabolizer. Risk of toxicity, alternative drug recommended. Details Cytochrome P450 2D6 CYP2D6*3 Not Available C allele Effect Inferred Poor drug metabolizer, lower dose requirements Details Cytochrome P450 2D6 CYP2D6*7 Not Available 2935A>C Effect Inferred Poor drug metabolizer, lower dose requirements Details Cytochrome P450 2D6 CYP2D6*8 Not Available 1758G>T Effect Inferred Poor drug metabolizer, lower dose requirements Details Cytochrome P450 2D6 CYP2D6*11 Not Available 883G>C Effect Inferred Poor drug metabolizer, lower dose requirements Details Cytochrome P450 2D6 CYP2D6*12 Not Available 124G>A Effect Inferred Poor drug metabolizer, lower dose requirements Details Cytochrome P450 2D6 CYP2D6*13 Not Available CYP2D7/2D6 hybrid gene structure Effect Inferred Poor drug metabolizer, lower dose requirements Details Cytochrome P450 2D6 CYP2D6*14A Not Available 1758G>A Effect Inferred Poor drug metabolizer, lower dose requirements Details Cytochrome P450 2D6 CYP2D6*15 Not Available 137insT, 137_138insT Effect Inferred Poor drug metabolizer, lower dose requirements Details Cytochrome P450 2D6 CYP2D6*19 Not Available 2539_2542delAACT Effect Inferred Poor drug metabolizer, lower dose requirements Details Cytochrome P450 2D6 CYP2D6*20 Not Available 1973_1974insG Effect Inferred Poor drug metabolizer, lower dose requirements Details Cytochrome P450 2D6 CYP2D6*21 Not Available 2573insC Effect Inferred Poor drug metabolizer, lower dose requirements Details Cytochrome P450 2D6 CYP2D6*31 Not Available -1770G>A / -1584C>G … show all Effect Inferred Poor drug metabolizer, lower dose requirements Details Cytochrome P450 2D6 CYP2D6*36 Not Available 100C>T / -1426C>T … show all Effect Inferred Poor drug metabolizer, lower dose requirements Details Cytochrome P450 2D6 CYP2D6*38 Not Available 2587_2590delGACT Effect Inferred Poor drug metabolizer, lower dose requirements Details Cytochrome P450 2D6 CYP2D6*40 Not Available 1863_1864ins(TTT CGC CCC)2 Effect Inferred Poor drug metabolizer, lower dose requirements Details Cytochrome P450 2D6 CYP2D6*42 Not Available 3259_3260insGT Effect Inferred Poor drug metabolizer, lower dose requirements Details Cytochrome P450 2D6 CYP2D6*44 Not Available 2950G>C Effect Inferred Poor drug metabolizer, lower dose requirements Details Cytochrome P450 2D6 CYP2D6*47 Not Available 100C>T / -1426C>T … show all Effect Inferred Poor drug metabolizer, lower dose requirements Details Cytochrome P450 2D6 CYP2D6*51 Not Available -1584C>G / -1235A>G … show all Effect Inferred Poor drug metabolizer, lower dose requirements Details Cytochrome P450 2D6 CYP2D6*56 Not Available 3201C>T Effect Inferred Poor drug metabolizer, lower dose requirements Details Cytochrome P450 2D6 CYP2D6*57 Not Available 100C>T / 310G>T … show all Effect Inferred Poor drug metabolizer, lower dose requirements Details Cytochrome P450 2D6 CYP2D6*62 Not Available 4044C>T Effect Inferred Poor drug metabolizer, lower dose requirements Details Cytochrome P450 2D6 CYP2D6*68A Not Available -1426C>T / -1235A>G … show all Effect Inferred Poor drug metabolizer, lower dose requirements Details Cytochrome P450 2D6 CYP2D6*68B Not Available Similar but not identical switch region compared to CYP2D6*68A. Found in tandem arrangement with CYP2D6*4. Effect Inferred Poor drug metabolizer, lower dose requirements Details Cytochrome P450 2D6 CYP2D6*69 Not Available 2988G>A / -1426C>T … show all Effect Inferred Poor drug metabolizer, lower dose requirements Details Cytochrome P450 2D6 CYP2D6*92 Not Available 1995delC Effect Inferred Poor drug metabolizer, lower dose requirements Details Cytochrome P450 2D6 CYP2D6*100 Not Available -1426C>T / -1235A>G … show all Effect Inferred Poor drug metabolizer, lower dose requirements Details Cytochrome P450 2D6 CYP2D6*101 Not Available -1426C>T / -1235A>G … show all Effect Inferred Poor drug metabolizer, lower dose requirements Details Cytochrome P450 2D6 CYP2D6*3 Not Available G allele Effect Directly Studied The presence of this polymorphism in CYP2D6 results in non-functioning enzyme variant and may be associated with reduced therapeutic response when treated with codeine. Details Cytochrome P450 2D6 CYP2D6*4 Not Available 3877G>A Effect Directly Studied The presence of this polymorphism in CYP2D6 results in non-functioning enzyme variant and may be associated with reduced therapeutic response when treated with codeine. Details
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of adverse effects can be increased when Codeine is combined with 1,2-Benzodiazepine. Abametapir The serum concentration of Codeine can be increased when it is combined with Abametapir. Abatacept The metabolism of Codeine can be increased when combined with Abatacept. Abiraterone The metabolism of Codeine can be decreased when combined with Abiraterone. Acebutolol The metabolism of Codeine can be decreased when combined with Acebutolol. - Food Interactions
- Avoid alcohol.
- Take with food. Food reduces irritation.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Codeine hydrobromide dihydrate Not Available Not Available YYPNRUMYXOJKDO-NLMNJOOOSA-N Codeine hydrochloride 406LPJ779Q 1422-07-7 NUXLENPAZQNFAM-FFHNEAJVSA-N Codeine monohydrate Q830PW7520 6059-47-8 WRRSFOZOETZUPG-FFHNEAJVSA-N Codeine phosphate 2X585M1M3T 52-28-8 WUXLCJZUUHIXFY-FFHNEAJVSA-N Codeine phosphate hemihydrate GSL05Y1MN6 41444-62-6 DKSZLDSPXIWGFO-BLOJGBSASA-N Codeine sulfate 11QV9BS0CB 6854-40-6 BOLDZXRCJAJADM-AAXBYHQXSA-N Codeine sulfate anhydrous AVW5HY4N2E 1420-53-7 BCXHDORHMMZBBZ-DORFAMGDSA-N - Product Images
- International/Other Brands
- Actacode (Sigma) / Bisoltus (Boehringer Ingelheim) / Bromophar (Qualiphar) / Bronchicum (Sanofi-Aventis) / Bronchodine (Pharmacobel) / Codant (Antigen) / Codedrill (Pierre Fabre) / Codein (Cristália) / Codeisan (Belmac) / Coderpina (Frycia Centro América) / Codicalm (Welti) / Codicept / Codinex (Pinewood) / Coducept / Cougel (Hwang's) / Coutan (Mey See) / Dinco (Center) / Farmacod (Farmacom) / Galcodine (Thornton & Ross) / Pectoral (Siphat) / Tussoret (MaxMedic)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Codeine 15 Tablet 15 mg Oral Laboratoire Riva Inc. 1994-12-31 Not applicable Canada 
Codeine 30 Tablet 30 mg Oral Laboratoire Riva Inc. 1994-12-31 Not applicable Canada Codeine Contin 100mg Controlled Release Tab Tablet, extended release 100 mg Oral Purdue Pharma 1995-12-31 Not applicable Canada Codeine Contin 150mg Controlled Release Tab Tablet, extended release 150 mg Oral Purdue Pharma 1995-12-31 Not applicable Canada Codeine Contin 200mg Controlled Release Tab Tablet, extended release 200 mg Oral Purdue Pharma 1995-12-31 Not applicable Canada - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Codeine Sulfate Tablet 15 mg/1 Oral Lannett Company, Inc. 2014-06-13 Not applicable US 
Codeine Sulfate Tablet 60 mg/1 Oral Lannett Company, Inc. 2014-06-13 Not applicable US Codeine Sulfate Tablet 30 mg/1 Oral Lannett Company, Inc. 2014-06-13 Not applicable US PMS-codeine Tablet 30 mg Oral Pharmascience Inc 2001-12-16 2019-04-04 Canada PMS-codeine Tablet 15 mg Oral Pharmascience Inc 2001-11-16 2019-04-04 Canada - Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image COLINCTUS 10 MIXTURE 10 mg/5 ml Elixir 10 mg/5ml Oral DRUG HOUSES OF AUSTRALIA PTE. LTD. 1989-06-22 Not applicable Singapore 
Linctus Tussis Rubra 10mg/5ml Elixir 10 mg/5ml Oral EURO ASIA MEDICO PTE. LTD. 1992-04-03 Not applicable Singapore SP-CODIN LINCTUS 9 mg/5 ml Elixir 9 mg/5ml Oral LUEN WAH MEDICAL COMPANY (SINGAPORE) PRIVATE LIMITED 1999-03-25 Not applicable Singapore - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image (extra Strength) Acetaminophen, Caffeine & 8mg Codeine Phosphate Caplets Codeine phosphate (8 mg) + Acetaminophen (500 mg) + Caffeine (15 mg) Tablet Oral Stanley Pharmaceuticals, A Division Of Vita Health Products Inc. 1998-07-22 2002-07-31 Canada 222 Tablets Codeine phosphate (8 mg) + Acetylsalicylic acid (375 mg) + Caffeine citrate (30 mg) Tablet Oral Mcneil Consumer Healthcare Division Of Johnson & Johnson Inc 1951-12-31 2015-08-17 Canada 282 Mep Tab Codeine phosphate (15 mg) + Acetylsalicylic acid (350 mg) + Caffeine citrate (30 mg) + Meprobamate (200 mg) Tablet Oral Merck Frosst Canada & Cie, Merck Frosst Canada & Co. 1959-12-31 1998-08-14 Canada 282 Tab Codeine phosphate (15 mg) + Acetylsalicylic acid (375 mg) + Caffeine citrate (30 mg) Tablet Oral Merck Frosst Canada & Cie, Merck Frosst Canada & Co. 1951-12-31 1998-04-21 Canada 282 Tablets Codeine phosphate (15 mg) + Acetylsalicylic acid (375 mg) + Caffeine citrate (30 mg) Tablet Oral Pendopharm Division Of Pharmascience Inc 1998-11-01 2021-05-11 Canada - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Airacof Codeine phosphate hemihydrate (7.5 mg/5mL) + Diphenhydramine hydrochloride (12.5 mg/5mL) + Phenylephrine hydrochloride (7.5 mg/5mL) Liquid Oral Centurion Labs 2010-01-08 2016-05-02 US Chlorpheniramine and Codeine Codeine phosphate hemihydrate (10 mg/5mL) + Chlorpheniramine maleate (2 mg/5mL) Liquid Oral Breckenridge Pharmaceutical, Inc. 2009-10-01 2011-02-28 US Codeine Phosphate and Pseudoephedrine Hydrochloride Codeine phosphate hemihydrate (10 mg/5mL) + Pseudoephedrine hydrochloride (30 mg/5mL) Syrup Oral Breckenridge Pharmaceutical, Inc. 2009-12-01 2011-11-30 US Codeine Phosphate Guaifenesin Codeine phosphate hemihydrate (10 mg/5mL) + Guaifenesin (200 mg/5mL) Liquid Oral Kylemore Pharmaceuticals, LLC 2010-01-01 2012-11-30 US Codeine Sulfate Codeine sulfate (30 mg/1) Tablet Oral Glenmark Generics, Inc. USA 2006-07-01 2011-08-31 US
Categories
- ATC Codes
- N02AA79 — Codeine, combinations with psycholepticsR05DA04 — Codeine
- R05DA — Opium alkaloids and derivatives
- R05D — COUGH SUPPRESSANTS, EXCL. COMBINATIONS WITH EXPECTORANTS
- R05 — COUGH AND COLD PREPARATIONS
- R — RESPIRATORY SYSTEM
- N02AJ — Opioids in combination with non-opioid analgesics
- N02A — OPIOIDS
- N02 — ANALGESICS
- N — NERVOUS SYSTEM
- N02AJ — Opioids in combination with non-opioid analgesics
- N02A — OPIOIDS
- N02 — ANALGESICS
- N — NERVOUS SYSTEM
- Drug Categories
- Alkaloids
- Analgesics
- Antitussive Agents
- Central Nervous System Agents
- Central Nervous System Depressants
- Cough and Cold Preparations
- Cytochrome P-450 CYP2D6 Substrates
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 Substrates
- Heterocyclic Compounds, Fused-Ring
- Morphinans
- Morphine Derivatives
- Narcotics
- Natural Opium Alkaloids
- Nervous System
- OAT1/SLC22A6 inhibitors
- OCT1 inhibitors
- OCT1 substrates
- Opiate Agonists
- Opiate Alkaloids
- Opioid Agonist
- Opioids
- Opium Alkaloids and Derivatives
- Phenanthrenes
- Respiratory System Agents
- Sensory System Agents
- Serotonergic Drugs Shown to Increase Risk of Serotonin Syndrome
- UGT2B7 substrates
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as morphinans. These are polycyclic compounds with a four-ring skeleton with three condensed six-member rings forming a partially hydrogenated phenanthrene moiety, one of which is aromatic while the two others are alicyclic.
- Kingdom
- Organic compounds
- Super Class
- Alkaloids and derivatives
- Class
- Morphinans
- Sub Class
- Not Available
- Direct Parent
- Morphinans
- Alternative Parents
- Phenanthrenes and derivatives / Tetralins / Coumarans / Anisoles / Aralkylamines / Alkyl aryl ethers / Piperidines / Trialkylamines / Secondary alcohols / Oxacyclic compounds show 3 more
- Substituents
- Alcohol / Alkyl aryl ether / Amine / Anisole / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Coumaran / Ether show 15 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- morphinane alkaloid, organic heteropentacyclic compound (CHEBI:16714) / Isoquinoline alkaloids (C06174)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- UX6OWY2V7J
- CAS number
- 76-57-3
- InChI Key
- OROGSEYTTFOCAN-DNJOTXNNSA-N
- InChI
- 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
- IUPAC Name
- (1S,5R,13R,14S,17R)-10-methoxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0^{1,13}.0^{5,17}.0^{7,18}]octadeca-7(18),8,10,15-tetraen-14-ol
- SMILES
- [H][C@]12C=C[C@H](O)[C@@H]3OC4=C5C(C[C@H]1N(C)CC[C@@]235)=CC=C4OC
References
- Synthesis Reference
Nagaraj R. Ayyangar, Anil R. Choudhary, Uttam R. Kalkote, Vasant K. Sharma, "Process for the preparation of codeine from morphine." U.S. Patent US4764615, issued May, 1912.
US4764615- General References
- Schroeder K, Fahey T: Over-the-counter medications for acute cough in children and adults in ambulatory settings. Cochrane Database Syst Rev. 2004 Oct 18;(4):CD001831. [Article]
- Vree TB, van Dongen RT, Koopman-Kimenai PM: Codeine analgesia is due to codeine-6-glucuronide, not morphine. Int J Clin Pract. 2000 Jul-Aug;54(6):395-8. [Article]
- Srinivasan V, Wielbo D, Tebbett IR: Analgesic effects of codeine-6-glucuronide after intravenous administration. Eur J Pain. 1997;1(3):185-90. [Article]
- Bhandari M, Bhandari A, Bhandari A: Recent updates on codeine. Pharm Methods. 2011 Jan;2(1):3-8. doi: 10.4103/2229-4708.81082. [Article]
- Chen ZR, Somogyi AA, Reynolds G, Bochner F: Disposition and metabolism of codeine after single and chronic doses in one poor and seven extensive metabolisers. Br J Clin Pharmacol. 1991 Apr;31(4):381-90. [Article]
- Takahama K, Wakuda I, Fukushima H, Isohama Y, Kai H, Miyata T: Differential effect of codeine on coughs caused by mechanical stimulation of two different sites in the airway of guinea pigs. Eur J Pharmacol. 1997 Jun 18;329(1):93-7. [Article]
- Straube C, Derry S, Jackson KC, Wiffen PJ, Bell RF, Strassels S, Straube S: Codeine, alone and with paracetamol (acetaminophen), for cancer pain. Cochrane Database Syst Rev. 2014 Sep 19;(9):CD006601. doi: 10.1002/14651858.CD006601.pub4. [Article]
- Boom M, Niesters M, Sarton E, Aarts L, Smith TW, Dahan A: Non-analgesic effects of opioids: opioid-induced respiratory depression. Curr Pharm Des. 2012;18(37):5994-6004. doi: 10.2174/138161212803582469. [Article]
- Prommer E: Role of codeine in palliative care. J Opioid Manag. 2011 Sep-Oct;7(5):401-6. [Article]
- Lotsch J: Opioid metabolites. J Pain Symptom Manage. 2005 May;29(5 Suppl):S10-24. doi: 10.1016/j.jpainsymman.2005.01.004. [Article]
- Al-Hasani R, Bruchas MR: Molecular mechanisms of opioid receptor-dependent signaling and behavior. Anesthesiology. 2011 Dec;115(6):1363-81. doi: 10.1097/ALN.0b013e318238bba6. [Article]
- Pan HL, Wu ZZ, Zhou HY, Chen SR, Zhang HM, Li DP: Modulation of pain transmission by G-protein-coupled receptors. Pharmacol Ther. 2008 Jan;117(1):141-61. doi: 10.1016/j.pharmthera.2007.09.003. Epub 2007 Sep 22. [Article]
- Codeine phosphate tablets, 30mg [Link]
- DailyMed: Codeine and promethazine syrup [Link]
- Codittusin, DailyMed [Link]
- FDA Approved Drug Products: CODEINE SULFATE tablets, for oral use CII (Jan 2024) [Link]
- FDA Approved Drug Products: Butalbital, Acetaminophen, Caffeine, and Codeine Phosphate Capsules for oral use, CIII (Jan 2024) [Link]
- EPAR, Codeine [File]
- Codeine, MedSafe NZ document [File]
- External Links
- Human Metabolome Database
- HMDB0004995
- KEGG Drug
- D03580
- KEGG Compound
- C06174
- PubChem Compound
- 5284371
- PubChem Substance
- 46507764
- ChemSpider
- 4447447
- BindingDB
- 50105098
- 1545976
- ChEBI
- 16714
- ChEMBL
- CHEMBL485
- ZINC
- ZINC000003806721
- Therapeutic Targets Database
- DAP000213
- PharmGKB
- PA449088
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Codeine
- FDA label
- Download (138 KB)
- MSDS
- Download (52.5 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Completed Not Available Cleft Palate Repair 1 4 Completed Other Esophageal Motility Disorders 1 4 Completed Supportive Care Pain / Unspecified Adult Solid Tumor, Protocol Specific 1 4 Completed Supportive Care Parathyroid Adenomas / Parathyroid Diseases / Parathyroid Hyperplasia / Thyroid Cancer / Thyroid Gland Diseases / Thyroid Goitre / Thyroid Neoplasm / Thyroid Nodules 1 4 Completed Supportive Care Post-operative Pain Management 1
Pharmacoeconomics
- Manufacturers
- Roxane laboratories inc
- Packagers
- Actavis Group
- Aidarex Pharmacuticals LLC
- Amarin Pharmaceuticals
- Amerisource Health Services Corp.
- Amneal Pharmaceuticals
- Apotheca Inc.
- A-S Medication Solutions LLC
- Athlon Pharmaceuticals Inc.
- Barr Pharmaceuticals
- BASF Corp.
- Blansett Pharmacal Co. Inc.
- Blenheim Pharmacal
- Breckenridge Pharmaceuticals
- Bryant Ranch Prepack
- C.O. Truxton Inc.
- Cardinal Health
- Carlisle Laboratories Inc.
- Centurion Labs
- Century Pharmaceuticals Inc.
- Cerovene Inc.
- Comprehensive Consultant Services Inc.
- Corepharma LLC
- Coupler Enterprises Inc.
- D.M. Graham Laboratories Inc.
- DAVA Pharmaceuticals
- Direct Dispensing Inc.
- Dispensing Solutions
- Diversified Healthcare Services Inc.
- Duramed
- Eon Labs
- Glenmark Generics Ltd.
- Golden State Medical Supply Inc.
- Great Southern Laboratories
- H and H Laboratories
- H.J. Harkins Co. Inc.
- Heartland Repack Services LLC
- Hi Tech Pharmacal Co. Inc.
- Hospira Inc.
- Innoviant Pharmacy Inc.
- Ivax Pharmaceuticals
- Janssen-Ortho Inc.
- Jerome Stevens Pharmaceuticals Inc.
- Kaiser Foundation Hospital
- Keltman Pharmaceuticals Inc.
- Lake Erie Medical and Surgical Supply
- Lannett Co. Inc.
- Lehigh Valley Technologies Inc.
- Liberty Pharmaceuticals
- Major Pharmaceuticals
- Mallinckrodt Inc.
- Mckesson Corp.
- MCR American Pharmaceuticals Inc.
- Medvantx Inc.
- Mikart Inc.
- Murfreesboro Pharmaceutical Nursing Supply
- Mutual Pharmaceutical Co.
- Nexgen Pharma Inc.
- Novartis AG
- Nucare Pharmaceuticals Inc.
- Ortho-McNeil-Janssen Pharmaceuticals Inc.
- Palmetto Pharmaceuticals Inc.
- Patient First Corp.
- PCA LLC
- PD-Rx Pharmaceuticals Inc.
- Pharmaceutical Association
- Pharmedix
- Pharmpak Inc.
- Physicians Total Care Inc.
- Poly Pharmaceuticals Inc.
- Preferred Pharmaceuticals Inc.
- Prepackage Specialists
- Prepak Systems Inc.
- Qualitest
- Ranbaxy Laboratories
- Rebel Distributors Corp.
- Redpharm Drug
- Remedy Repack
- Roxane Labs
- Sandhills Packaging Inc.
- SJ Pharmaceuticals LLC
- Southwood Pharmaceuticals
- St Mary's Medical Park Pharmacy
- Stanley Pharmaceuticals Ltd.
- Stat Rx Usa
- Talbert Medical Management Corp.
- Teva Pharmaceutical Industries Ltd.
- TG United Inc.
- UDL Laboratories
- United Research Laboratories Inc.
- Va Cmop Dallas
- Valeant Ltd.
- Vascondor Inc.
- Veratex Corp.
- Vintage Pharmaceuticals Inc.
- Watson Pharmaceuticals
- West-Ward Pharmaceuticals
- Wockhardt Ltd.
- Dosage Forms
Form Route Strength Tablet Oral Solution Oral Tablet, coated Oral Syrup Oral 10 mg/5ml Syrup Oral Solution Oral 24 mg/mL Capsule Oral Elixir Oral 4 mg/5ml Tablet, effervescent Oral Tablet, effervescent Solution Oral 16 MG/ML Tablet, extended release Oral Tablet, extended release Oral 100 mg Tablet, extended release Oral 150 mg Tablet, extended release Oral 200 mg Tablet, extended release Oral 50 mg Tablet Oral Solution Intramuscular; Subcutaneous 30 mg / 1 mL Solution Intramuscular; Subcutaneous 60 mg / 1 mL Liquid Intramuscular; Subcutaneous 30 mg / 1 mL Syrup Oral 25 mg / 5 mL Syrup Oral 5 mg / mL Tablet Oral 15 mg Tablet Oral 60 mg Solution Oral 15 mg/2.5mL Solution Oral 30 mg/5mL Tablet Oral 15 mg/1 Tablet Oral 30 mg/1 Tablet Oral 60 mg/1 Solution Oral 1 MG Tablet Oral 50 mg/1 Suspension, extended release Oral Capsule Oral 30 mg/1 Capsule, extended release Oral Capsule, extended release Oral 30 mg Elixir Oral 10 mg/5ml Elixir Oral 9 mg/5ml Syrup Syrup Oral 9 mg/5ml Solution / drops Oral Suppository Rectal 180 mg Suppository Rectal 360 mg Tablet, film coated Oral Solution Oral 10 mg / 5 mL Suppository Rectal Tablet Oral 9 mg Tablet Oral 8 mg Granule, effervescent Oral Liquid Oral 10 mg / mL Tablet Oral 30 mg Syrup Oral Capsule, liquid filled Oral Liquid Oral Elixir Oral 9 mg/5ml Elixir Oral 10.0 mg/5ml Granule Oral Elixir Oral Kit Oral Solution Oral 22.1 mg/g Solution Oral 2.5 mg/mL Syrup Oral 135 mg/5ml Elixir Oral 10 mg/5ml Suspension Oral - Prices
Unit description Cost Unit Codeine phosphate powder 8.25USD g Codeine Phosphate 30 mg/ml 1.31USD ml Codeine sulfate 60 mg tablet 0.86USD tablet Codeine sulfate 30 mg tablet 0.76USD tablet Codeine ph 30 mg/ml syringe 0.54USD ml Codeine ph 15 mg/ml syringe 0.49USD ml Codeine sulfate 15 mg tablet 0.43USD tablet Ratio-Codeine 30 mg Tablet 0.09USD tablet Ratio-Codeine 15 mg Tablet 0.07USD tablet Ratio-Codeine 5 mg/ml Syrup 0.03USD ml DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US8062667 No 2011-11-22 2029-03-29 US US8790700 No 2014-07-29 2027-03-15 US US9066942 No 2015-06-30 2032-01-03 US US6383471 No 2002-05-07 2019-04-06 US US6248363 No 2001-06-19 2019-11-23 US US9107921 No 2015-08-18 2032-01-03 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 154-156 MSDS boiling point (°C) 250 http://www.chm.bris.ac.uk/webprojects2002/winder/information.htm water solubility soluble in water http://www.mhra.gov.uk/home/groups/par/documents/websiteresources/con126132.pdf logP 1.39 https://www.agilent.com/cs/library/applications/5990-9625EN.pdf logS -1.52 ADMET & DMPK 1(4) (2013) 48-62; doi: 10.5599/admet.1.4.24 pKa 8.2 http://www.inchem.org/documents/pims/pharm/codeine.htm - Predicted Properties
Property Value Source Water Solubility 0.577 mg/mL ALOGPS logP 1.2 ALOGPS logP 1.34 Chemaxon logS -2.7 ALOGPS pKa (Strongest Acidic) 13.78 Chemaxon pKa (Strongest Basic) 9.19 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 41.93 Å2 Chemaxon Rotatable Bond Count 1 Chemaxon Refractivity 84.6 m3·mol-1 Chemaxon Polarizability 31.95 Å3 Chemaxon Number of Rings 5 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9966 Blood Brain Barrier + 0.9979 Caco-2 permeable + 0.8867 P-glycoprotein substrate Substrate 0.8631 P-glycoprotein inhibitor I Inhibitor 0.5435 P-glycoprotein inhibitor II Non-inhibitor 0.8724 Renal organic cation transporter Inhibitor 0.638 CYP450 2C9 substrate Non-substrate 0.7698 CYP450 2D6 substrate Substrate 0.9274 CYP450 3A4 substrate Substrate 0.7796 CYP450 1A2 substrate Non-inhibitor 0.6494 CYP450 2C9 inhibitor Non-inhibitor 0.8866 CYP450 2D6 inhibitor Inhibitor 0.6978 CYP450 2C19 inhibitor Non-inhibitor 0.8256 CYP450 3A4 inhibitor Non-inhibitor 0.8899 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.747 Ames test Non AMES toxic 0.9133 Carcinogenicity Non-carcinogens 0.9567 Biodegradation Not ready biodegradable 0.9935 Rat acute toxicity 2.8450 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8556 hERG inhibition (predictor II) Non-inhibitor 0.8615
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 174.847793 predictedDarkChem Lite v0.1.0 [M-H]- 175.160093 predictedDarkChem Lite v0.1.0 [M-H]- 174.739793 predictedDarkChem Lite v0.1.0 [M-H]- 174.61856 predictedDeepCCS 1.0 (2019) [M+H]+ 174.899893 predictedDarkChem Lite v0.1.0 [M+H]+ 175.225793 predictedDarkChem Lite v0.1.0 [M+H]+ 175.147793 predictedDarkChem Lite v0.1.0 [M+H]+ 177.01411 predictedDeepCCS 1.0 (2019) [M+Na]+ 174.999293 predictedDarkChem Lite v0.1.0 [M+Na]+ 175.306393 predictedDarkChem Lite v0.1.0 [M+Na]+ 175.051793 predictedDarkChem Lite v0.1.0 [M+Na]+ 184.3921 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- AgonistRegulator
- General Function
- Voltage-gated calcium channel activity
- Specific Function
- Receptor for endogenous opioids such as beta-endorphin and endomorphin. Receptor for natural and synthetic opioids including morphine, heroin, DAMGO, fentanyl, etorphine, buprenorphin and methadone...
- Gene Name
- OPRM1
- Uniprot ID
- P35372
- Uniprot Name
- Mu-type opioid receptor
- Molecular Weight
- 44778.855 Da
References
- Takahama K, Shirasaki T: Central and peripheral mechanisms of narcotic antitussives: codeine-sensitive and -resistant coughs. Cough. 2007 Jul 9;3:8. [Article]
- Raffa RB: A novel approach to the pharmacology of analgesics. Am J Med. 1996 Jul 31;101(1A):40S-46S. doi: 10.1016/s0002-9343(96)00137-4. [Article]
- Codeine FDA label [File]
- EPAR, Codeine [File]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- Curator comments
- This target action is based on in vitro data.
- General Function
- Opioid receptor activity
- Specific Function
- G-protein coupled opioid receptor that functions as receptor for endogenous alpha-neoendorphins and dynorphins, but has low affinity for beta-endorphins. Also functions as receptor for various synt...
- Gene Name
- OPRK1
- Uniprot ID
- P41145
- Uniprot Name
- Kappa-type opioid receptor
- Molecular Weight
- 42644.665 Da
References
- Mignat C, Wille U, Ziegler A: Affinity profiles of morphine, codeine, dihydrocodeine and their glucuronides at opioid receptor subtypes. Life Sci. 1995;56(10):793-9. [Article]
- Schmidt H, Vormfelde Sv, Klinder K, Gundert-Remy U, Gleiter CH, Skopp G, Aderjan R, Fuhr U: Affinities of dihydrocodeine and its metabolites to opioid receptors. Pharmacol Toxicol. 2002 Aug;91(2):57-63. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- Opioid receptor activity
- Specific Function
- G-protein coupled receptor that functions as receptor for endogenous enkephalins and for a subset of other opioids. Ligand binding causes a conformation change that triggers signaling via guanine n...
- Gene Name
- OPRD1
- Uniprot ID
- P41143
- Uniprot Name
- Delta-type opioid receptor
- Molecular Weight
- 40368.235 Da
References
- Mignat C, Wille U, Ziegler A: Affinity profiles of morphine, codeine, dihydrocodeine and their glucuronides at opioid receptor subtypes. Life Sci. 1995;56(10):793-9. [Article]
- Schmidt H, Vormfelde Sv, Klinder K, Gundert-Remy U, Gleiter CH, Skopp G, Aderjan R, Fuhr U: Affinities of dihydrocodeine and its metabolites to opioid receptors. Pharmacol Toxicol. 2002 Aug;91(2):57-63. [Article]
- ChemBL resource, opioid receptors [Link]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Steroid hydroxylase activity
- Specific Function
- Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
- Gene Name
- CYP2D6
- Uniprot ID
- P10635
- Uniprot Name
- Cytochrome P450 2D6
- Molecular Weight
- 55768.94 Da
References
- Zhou SF: Polymorphism of human cytochrome P450 2D6 and its clinical significance: Part I. Clin Pharmacokinet. 2009;48(11):689-723. doi: 10.2165/11318030-000000000-00000. [Article]
- Yue QY, Sawe J: Different effects of inhibitors on the O- and N-demethylation of codeine in human liver microsomes. Eur J Clin Pharmacol. 1997;52(1):41-7. [Article]
- Flockhart Table of Drug Interactions [Link]
- Codeine FDA label [File]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Vitamin d3 25-hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- Williams JA, Hyland R, Jones BC, Smith DA, Hurst S, Goosen TC, Peterkin V, Koup JR, Ball SE: Drug-drug interactions for UDP-glucuronosyltransferase substrates: a pharmacokinetic explanation for typically observed low exposure (AUCi/AUC) ratios. Drug Metab Dispos. 2004 Nov;32(11):1201-8. doi: 10.1124/dmd.104.000794. Epub 2004 Aug 10. [Article]
- Yue QY, Sawe J: Different effects of inhibitors on the O- and N-demethylation of codeine in human liver microsomes. Eur J Clin Pharmacol. 1997;52(1):41-7. [Article]
- Codeine FDA label [File]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Glucuronosyltransferase activity
- Specific Function
- UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.Its unique specificity for 3,4-catechol estrogens and estriol su...
- Gene Name
- UGT2B7
- Uniprot ID
- P16662
- Uniprot Name
- UDP-glucuronosyltransferase 2B7
- Molecular Weight
- 60694.12 Da
References
- Coffman BL, Rios GR, King CD, Tephly TR: Human UGT2B7 catalyzes morphine glucuronidation. Drug Metab Dispos. 1997 Jan;25(1):1-4. [Article]
- Raungrut P, Uchaipichat V, Elliot DJ, Janchawee B, Somogyi AA, Miners JO: In vitro-in vivo extrapolation predicts drug-drug interactions arising from inhibition of codeine glucuronidation by dextropropoxyphene, fluconazole, ketoconazole, and methadone in humans. J Pharmacol Exp Ther. 2010 Aug;334(2):609-18. doi: 10.1124/jpet.110.167916. Epub 2010 May 18. [Article]
- Codeine FDA label [File]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Glucuronosyltransferase activity
- Specific Function
- UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme is active on polyhydroxylated estrogens (such as...
- Gene Name
- UGT2B4
- Uniprot ID
- P06133
- Uniprot Name
- UDP-glucuronosyltransferase 2B4
- Molecular Weight
- 60512.035 Da
References
- Raungrut P, Uchaipichat V, Elliot DJ, Janchawee B, Somogyi AA, Miners JO: In vitro-in vivo extrapolation predicts drug-drug interactions arising from inhibition of codeine glucuronidation by dextropropoxyphene, fluconazole, ketoconazole, and methadone in humans. J Pharmacol Exp Ther. 2010 Aug;334(2):609-18. doi: 10.1124/jpet.110.167916. Epub 2010 May 18. [Article]
- Gelston EA, Coller JK, Lopatko OV, James HM, Schmidt H, White JM, Somogyi AA: Methadone inhibits CYP2D6 and UGT2B7/2B4 in vivo: a study using codeine in methadone- and buprenorphine-maintained subjects. Br J Clin Pharmacol. 2012 May;73(5):786-94. doi: 10.1111/j.1365-2125.2011.04145.x. [Article]
- Codeine FDA label [File]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- General Function
- Secondary active organic cation transmembrane transporter activity
- Specific Function
- Translocates a broad array of organic cations with various structures and molecular weights including the model compounds 1-methyl-4-phenylpyridinium (MPP), tetraethylammonium (TEA), N-1-methylnico...
- Gene Name
- SLC22A1
- Uniprot ID
- O15245
- Uniprot Name
- Solute carrier family 22 member 1
- Molecular Weight
- 61153.345 Da
References
- Tzvetkov MV, dos Santos Pereira JN, Meineke I, Saadatmand AR, Stingl JC, Brockmoller J: Morphine is a substrate of the organic cation transporter OCT1 and polymorphisms in OCT1 gene affect morphine pharmacokinetics after codeine administration. Biochem Pharmacol. 2013 Sep 1;86(5):666-78. doi: 10.1016/j.bcp.2013.06.019. Epub 2013 Jul 5. [Article]
- Dujic T, Zhou K, Donnelly LA, Tavendale R, Palmer CN, Pearson ER: Association of Organic Cation Transporter 1 With Intolerance to Metformin in Type 2 Diabetes: A GoDARTS Study. Diabetes. 2015 May;64(5):1786-93. doi: 10.2337/db14-1388. Epub 2014 Dec 15. [Article]
- Venkatasubramanian R, Fukuda T, Niu J, Mizuno T, Chidambaran V, Vinks AA, Sadhasivam S: ABCC3 and OCT1 genotypes influence pharmacokinetics of morphine in children. Pharmacogenomics. 2014 Jul;15(10):1297-309. doi: 10.2217/pgs.14.99. [Article]
Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:55