コデイン

Also known as Codicept®, methylmorphine, morphine 3-methyl ether, morphine monomethyl ether, morphine-3-methyl ether, O(3)-methylmorphine, l-codeine, codeine anhydrous

Codeine is an opiate and prodrug of morphine mainly used to treat pain, coughing, and diarrhea. It is commonly used as a recreational drug. It is found naturally in the sap of the opium poppy, Papaver somniferum. It is typically used to treat mild to moderate degrees of pain. Greater benefit may occur when combined with paracetamol (acetaminophen) as codeine/paracetamol or a nonsteroidal anti-inflammatory drug (NSAID) such as aspirin or ibuprofen. Evidence does not support its use for acute cough suppression in children. In Europe, it is not recommended as a cough medicine for those under 12 y

OverviewAI-generated

Codeine is a chemical compound with the formula C₁₈H₂₁NO₃. Its IUPAC name is (4R,4aR,7S,7aR,12bS)-9-methoxy-3-methyl-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-ol. The substance has a mass of 299.152 and a weight of 299.4. It carries a defined daily dose of 0.1.

Chemical properties include an xlogp of 1.1 and a tpsa of 41.9. The molecule contains one hydrogen bond donor and four hydrogen bond acceptors, with a charge of 0. It is referenced by 1,577 other encyclopedia articles.

Synthesized by Vinony from 19 facts across 4 sources: Wikidata, PubChem, PubMed, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.

Key facts

Drug.image: Codeine Structure.svg
Drug.image_class: skin-invert-image
Drug.width: 175
Drug.alt: Skeletal formula
Drug.image2: Codeine molecule ball.png
Drug.image_class2: bg-transparent
Drug.alt2: Ball-and-stick model
Drug.MedlinePlus: a682065
Drug.DailyMedID: Codeine
Drug.pregnancy_AU: A
Drug.dependency_liability: High
Drug.addiction_liability: High
Drug.routes_of_administration: By mouth, rectal, subcutaneous, intramuscular
Drug.ATC_prefix: R05
Drug.ATC_suffix: DA04
Drug.ATC_supplemental: Combinations: , , , ,
Drug.legal_AU: S8
Drug.legal_AU_comment: / S4 (Prescription only)

via Wikipedia infobox

Chemical data

Formula: C18H21NO3
Molecular weight: 299.4 g/mol
IUPAC name: (4R,4aR,7S,7aR,12bS)-9-methoxy-3-methyl-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-ol
SMILES: CN1CC[C@]23[C@@H]4[C@H]1CC5=C2C(=C(C=C5)OC)O[C@H]3[C@H](C=C4)O
InChIKey: OROGSEYTTFOCAN-DNJOTXNNSA-N
XLogP: 1.1
Polar surface area: 41.9 Å²
H-bond donors: 1
H-bond acceptors: 4
Formal charge: 0

via PubChem

Research

11,315 papers

A Review of Analytical Methods for Codeine Determination.ReviewMolecules (Basel, Switzerland) · 2021Pratiwi R, Noviana E, Fauziati R et al.DOI: 10.3390/molecules26040800
Codeine, cough and upper respiratory infection.ReviewPulmonary pharmacology · 1996Eccles RDOI: 10.1006/pulp.1996.0038
Concise Total Synthesis of (-)-Codeine.The Journal of organic chemistry · 2024Mondal A, Pal S, Khatua A et al.DOI: 10.1021/acs.joc.4c01452
Codeine sensitivity.British medical journal · 1951MACKENZIE GKDOI: 10.1136/bmj.1.4701.281
Identifying and treating codeine dependence: a systematic review.The Medical journal of Australia · 2018Nielsen S, MacDonald T, Johnson JLDOI: 10.5694/mja17.00749
Codeine analgesia is due to codeine-6-glucuronide, not morphine.ReviewInternational journal of clinical practice · 2000Vree TB, van Dongen RT, Koopman-Kimenai PM
A software tool to adjust codeine dose based on CYP2D6 gene-pair polymorphisms and drug-drug interactions.ReviewThe pharmacogenomics journal · 2023Saab Y, Nakad ZDOI: 10.1038/s41397-023-00318-7
The pharmacogenetics of codeine hypoalgesia.ReviewPharmacogenetics · 1995Sindrup SH, Brøsen KDOI: 10.1097/00008571-199512000-00001

via PubMed

Wikidata facts

Has part: carbon
Mass: 299.152
Has use: medication

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found in taxon: Papaver armeniacum
chemical formula: C₁₈H₂₁NO₃
Commons category: Codeine
canonical SMILES: CN1CCC23C4C1CC5=C2C(=C(C=C5)OC)OC3C(C=C4)O
isomeric SMILES: CN1CC[C@]23[C@@H]4[C@H]1CC5=C2C(=C(C=C5)OC)O[C@H]3[C@H](C=C4)O
World Health Organisation international non-proprietary name: codeine
defined daily dose: 0.1
subject has role: essential medicine
medical condition treated: cough
significant drug interaction: primidone
stereoisomer of: Isocodeine

Sources (6)

via Wikidata · CC0

Article · 日本語

コデイン（英: Codeine）またはメチルモルヒネは鎮痛、鎮咳、および下痢止めの作用のある、μ受容体アゴニストのオピオイドである。塩の形態の硫酸コデインもしくはリン酸コデインとして製品化されている。リン酸コデインは鎮痛剤（疼痛の緩和ケア）や下痢止めとして用いられるが、コデインを還元して製造したジヒドロコデインを鎮咳薬（咳止め薬）として風邪薬に配合するのが一般的である。コデインは1832年にアヘンから単離された。プロドラッグであり、代謝産物の約10%がモルヒネとなる。コデインは世界保健機関(WHO)の必須医薬品に定められている。WHO方式がん性痛治療法では、第2段階の弱オピオイドの第1選択薬に指定されている。日本の処方箋医薬品としては、劇薬に区分される。乱用されやすく、国際条約である麻薬に関する単一条約が、コデインをスケジュールII薬物に指定している。

Abstract from DBpedia / Wikipedia · CC BY-SA

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コデイン