Codeine (BioDeep_00000397764)

Main id: BioDeep_00000001452

Secondary id: BioDeep_00000865385

natural product PANOMIX_OTCML-2023


代谢物信息卡片


(-)-codeine

化学式: C18H21NO3 (299.1521356)
中文名称: 可待因
谱图信息: 最多检出来源 Viridiplantae(plant) 1.35%

分子结构信息

SMILES: CN1CCC23C4C1CC5=C2C(=C(C=C5)OC)OC3C(C=C4)O
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

描述信息

R - Respiratory system > R05 - Cough and cold preparations > R05D - Cough suppressants, excl. combinations with expectorants > R05DA - Opium alkaloids and derivatives
A morphinane alkaloid found in the opium poppy, Papaver somniferum var. album; has analgesic, anti-tussive and anti-diarrhoeal properties.
D002491 - Central Nervous System Agents > D002492 - Central Nervous System Depressants > D009294 - Narcotics
D002492 - Central Nervous System Depressants > D009294 - Narcotics > D053610 - Opiate Alkaloids
C78272 - Agent Affecting Nervous System > C67413 - Opioid Receptor Agonist > C1657 - Opiate
D018373 - Peripheral Nervous System Agents > D018689 - Sensory System Agents
D019141 - Respiratory System Agents > D000996 - Antitussive Agents
D002491 - Central Nervous System Agents > D000700 - Analgesics
relative retention time with respect to 9-anthracene Carboxylic Acid is 0.308
relative retention time with respect to 9-anthracene Carboxylic Acid is 0.294
IPB_RECORD: 924; CONFIDENCE confident structure
CONFIDENCE standard compound; EAWAG_UCHEM_ID 2780

同义名列表

2 个代谢物同义名

(-)-codeine; Codeine



数据库引用编号

39 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

4 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

  • PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。



文献列表

  • Winfried Häuser, Patrick Welsch, Lukas Radbruch, Emma Fisher, Rae Frances Bell, R Andrew Moore. Cannabis-based medicines and medical cannabis for adults with cancer pain. The Cochrane database of systematic reviews. 2023 06; 6(?):CD014915. doi: 10.1002/14651858.cd014915.pub2. [PMID: 37283486]
  • Agrataben Vadhel, Sabreen Bashir, Ashiq Hussain Mir, Madhuri Girdhar, Deepak Kumar, Anil Kumar, Aradhana Mohan, Tabarak Malik, Anand Mohan. Opium alkaloids, biosynthesis, pharmacology and association with cancer occurrence. Open biology. 2023 May; 13(5):220355. doi: 10.1098/rsob.220355. [PMID: 37132222]
  • Vedrana Bulat, Robert Likic, Nives Pondeljak, Marija Delas Azdajic. Pholcodine-induced Stevens-Johnson syndrome in a patient with COVID-19. Postgraduate medical journal. 2022 07; 98(1161):499-500. doi: 10.1136/postgradmedj-2021-139892. [PMID: 33879549]
  • Heba Elmansi, Fathalla Belal, Galal Magdy. Determination of pholcodine alone or in combination with ephedrine in human plasma using fluorescence spectroscopy. Scientific reports. 2022 06; 12(1):9372. doi: 10.1038/s41598-022-13194-1. [PMID: 35672340]
  • Vlad Radoi, Gerd Jakobsson, Vinko Palada, Andrej Nikosjkov, Henrik Druid, Lars Terenius, Eva Kosek, Vladana Vukojević. Non-Peptide Opioids Differ in Effects on Mu-Opioid (MOP) and Serotonin 1A (5-HT1A) Receptors Heterodimerization and Cellular Effectors (Ca2+, ERK1/2 and p38) Activation. Molecules (Basel, Switzerland). 2022 Apr; 27(7):. doi: 10.3390/molecules27072350. [PMID: 35408749]
  • Martina Šutovská, Michaela Kocmálová, Jozef Mažerik, Izabela Pawlaczyk-Graja, Roman Gancarz, Peter Capek. Chemical characteristics and significant antitussive effect of the Erigeron canadensis polyphenolic polysaccharide-protein complex. Journal of ethnopharmacology. 2022 Feb; 284(?):114754. doi: 10.1016/j.jep.2021.114754. [PMID: 34662663]
  • Ida Kuhlmann, Amanda Nøddebo Nyrup, Tore Bjerregaard Stage, Mette Marie Hougaard Christensen, Troels Korshøj Bergmann, Per Damkier, Flemming Nielsen, Kurt Højlund, Kim Brøsen. Oral and intravenous pharmacokinetics of metformin with and without oral codeine intake in healthy subjects: A cross-over study. Clinical and translational science. 2021 11; 14(6):2408-2419. doi: 10.1111/cts.13107. [PMID: 34268884]
  • Marie Epain, Nathalie Cartiser, Fabien Bévalot, Laurent Fanton. Toxicological detection of pholcodine in blood, urine and hair in three cases of fatal intoxication. Forensic science international. 2021 Oct; 327(?):110975. doi: 10.1016/j.forsciint.2021.110975. [PMID: 34478894]
  • R E Akhigbe, L O Ajayi, A F Ajayi. Codeine exerts cardiorenal injury via upregulation of adenine deaminase/xanthine oxidase and caspase 3 signaling. Life sciences. 2021 May; 273(?):118717. doi: 10.1016/j.lfs.2020.118717. [PMID: 33159958]
  • Joht Singh Chandan, Dawit Tefra Zemedikun, Rasiah Thayakaran, Nathan Byne, Samir Dhalla, Dionisio Acosta-Mena, Krishna M Gokhale, Tom Thomas, Christopher Sainsbury, Anuradhaa Subramanian, Jennifer Cooper, Astha Anand, Kelvin O Okoth, Jingya Wang, Nicola J Adderley, Thomas Taverner, Alastair K Denniston, Janet Lord, G Neil Thomas, Christopher D Buckley, Karim Raza, Neeraj Bhala, Krishnarajah Nirantharakumar, Shamil Haroon. Nonsteroidal Antiinflammatory Drugs and Susceptibility to COVID-19. Arthritis & rheumatology (Hoboken, N.J.). 2021 05; 73(5):731-739. doi: 10.1002/art.41593. [PMID: 33185016]
  • Adel Ghorani-Azam, Mahdi Balali-Mood, Seyed-Mola Khatami, Ahmad Asoodeh, Zarrin Es'haghi, Bamdad Riahi-Zanjani. Plant Extract and Herbal Products as Potential Source of Sorbent for Analytical Purpose: An Experimental Study of Morphine and Codeine Determination Using HPLC and LC-MSMS. Journal of chromatographic science. 2021 Apr; 59(5):482-489. doi: 10.1093/chromsci/bmaa108. [PMID: 33388745]
  • Gerd Jakobsson, Michael T Truver, Sonja A Wrobel, Henrik Gréen, Robert Kronstrand. Heroin-Related Compounds and Metabolic Ratios in Postmortem Samples Using LC-MS-MS. Journal of analytical toxicology. 2021 Mar; 45(3):215-225. doi: 10.1093/jat/bkaa157. [PMID: 33031535]
  • S R Gretler, C J Finno, P H Kass, H K Knych. Functional phenotyping of the CYP2D6 probe drug codeine in the horse. BMC veterinary research. 2021 Feb; 17(1):77. doi: 10.1186/s12917-021-02788-y. [PMID: 33581736]
  • Hany Ibrahim, Abdallah M Hamdy, Hanan A Merey, Ahmed S Saad. Simultaneous Determination of Paracetamol, Propyphenazone and Caffeine in Presence of Paracetamol Impurities Using Dual-Mode Gradient HPLC and TLC Densitometry Methods. Journal of chromatographic science. 2021 Jan; 59(2):140-147. doi: 10.1093/chromsci/bmaa088. [PMID: 33221830]
  • Hang Gao, Yaxun Liu, Wei Ke, Kai Liu, Liuyang Ni, Tao Tao. [Simultaneous determination of four opioids in urine by solid-phase extraction and derivatization coupled with gas chromatography-mass spectrometry]. Se pu = Chinese journal of chromatography. 2020 Nov; 38(11):1348-1354. doi: 10.3724/sp.j.1123.2020.06002. [PMID: 34213107]
  • Ahmed I Al-Asmari. Postmortem Liver and Kidney Tissue Concentrations of Heroin Biomarkers and Their Metabolites in Heroin-Related Fatalities*†. Journal of forensic sciences. 2020 Nov; 65(6):2087-2093. doi: 10.1111/1556-4029.14537. [PMID: 33460103]
  • D Silveira. Co-codamol okay. British dental journal. 2020 10; 229(7):398. doi: 10.1038/s41415-020-2239-6. [PMID: 33037336]
  • Sophie R Gretler, Carrie J Finno, Daniel S McKemie, Philip H Kass, Heather K Knych. Metabolism, pharmacokinetics and selected pharmacodynamic effects of codeine following a single oral administration to horses. Veterinary anaesthesia and analgesia. 2020 Sep; 47(5):694-704. doi: 10.1016/j.vaa.2020.04.004. [PMID: 32654915]
  • Steven C Budsberg, Stephanie A Kleine, Megan M Norton, Gabriella S Sandberg, Mark G Papich. Comparison of the effects on lameness of orally administered acetaminophen-codeine and carprofen in dogs with experimentally induced synovitis. American journal of veterinary research. 2020 Aug; 81(8):627-634. doi: 10.2460/ajvr.81.8.627. [PMID: 32701001]
  • Yichao Wang, Yue Yu, Guoxiang Sun, Yong Guo. Quality evaluation of powdered poppy capsule extractive by systematic quantified fingerprint method combined with quantitative analysis of multi-components by single marker method. Journal of pharmaceutical and biomedical analysis. 2020 Jun; 185(?):113247. doi: 10.1016/j.jpba.2020.113247. [PMID: 32193042]
  • Atyeh Rahimi, Saeed Nojavan, Hadi Tabani. Inside gel electromembrane extraction: A novel green methodology for the extraction of morphine and codeine from human biological fluids. Journal of pharmaceutical and biomedical analysis. 2020 May; 184(?):113175. doi: 10.1016/j.jpba.2020.113175. [PMID: 32097772]
  • Shalaka A Shetge, Michael P Dzakovich, Jessica L Cooperstone, Daria Kleinmeier, Benjamin W Redan. Concentrations of the Opium Alkaloids Morphine, Codeine, and Thebaine in Poppy Seeds are Reduced after Thermal and Washing Treatments but are Not Affected when Incorporated in a Model Baked Product. Journal of agricultural and food chemistry. 2020 May; 68(18):5241-5248. doi: 10.1021/acs.jafc.0c01681. [PMID: 32302121]
  • A F Ajayi, R E Akhigbe. Assessment of sexual behaviour and fertility indices in male rabbits following chronic codeine use. Andrology. 2020 03; 8(2):509-515. doi: 10.1111/andr.12717. [PMID: 31627249]
  • Ahmed I Al-Asmari. Postmortem Fluid Concentrations of Heroin Biomarkers and Their Metabolites. Journal of forensic sciences. 2020 Mar; 65(2):570-579. doi: 10.1111/1556-4029.14200. [PMID: 31566759]
  • Yao-Te Yen, Yin-Jue Chang, Pin-Jung Lai, Chi-Lun Chang, Ting-Yueh Chen, San-Chong Chyueh. A Study of Opiate, Opiate Metabolites and Antihistamines in Urine after Consumption of Cold Syrups by LC-MS/MS. Molecules (Basel, Switzerland). 2020 Feb; 25(4):. doi: 10.3390/molecules25040972. [PMID: 32098143]
  • Ali Farahani, Hassan Sereshti. An integrated microfluidic device for solid-phase extraction and spectrophotometric detection of opium alkaloids in urine samples. Analytical and bioanalytical chemistry. 2020 Jan; 412(1):129-138. doi: 10.1007/s00216-019-02214-1. [PMID: 31773230]
  • Miki Ota, Makiko Shimizu, Yusuke Kamiya, Chie Emoto, Tsuyoshi Fukuda, Hiroshi Yamazaki. Adult and infant pharmacokinetic profiling of dihydrocodeine using physiologically based pharmacokinetic modeling. Biopharmaceutics & drug disposition. 2019 Nov; 40(9):350-357. doi: 10.1002/bdd.2209. [PMID: 31691978]
  • Mehran Dastmalchi, Limei Chang, Rongji Chen, Lisa Yu, Xue Chen, Jillian M Hagel, Peter J Facchini. Purine Permease-Type Benzylisoquinoline Alkaloid Transporters in Opium Poppy. Plant physiology. 2019 11; 181(3):916-933. doi: 10.1104/pp.19.00565. [PMID: 31467164]
  • Meena K Yadav, Anu Kumar, Michael D Short, Bhanu Nidumolu, Christopher P Saint. Aquatic Phytotoxicity to Lemna minor of Three Commonly Used Drugs of Addiction in Australia. Bulletin of environmental contamination and toxicology. 2019 Nov; 103(5):710-716. doi: 10.1007/s00128-019-02708-9. [PMID: 31482305]
  • Ahmad Pourahadi, Ali Farahani, Saied Saeed Hosseiny Davarani, Saeed Nojavan, Camellia Tashakori. Developing a miniaturized setup for in-tube simultaneous determination of three alkaloids using electromembrane extraction in combination with ultraviolet spectrophotometry. Journal of separation science. 2019 Oct; 42(19):3126-3133. doi: 10.1002/jssc.201900276. [PMID: 31347772]
  • Chetan Shende, Carl Brouillette, Stuart Farquharson. Detection of codeine and fentanyl in saliva, blood plasma and whole blood in 5-minutes using a SERS flow-separation strip. The Analyst. 2019 Sep; 144(18):5449-5454. doi: 10.1039/c9an01087d. [PMID: 31424465]
  • Chee-Yuen Gan, Zafarina Zainuddin, Hayati Muhamad Noh, Rozaiha Rahmat, Fazilah Mohd Akir, Nur Hana Mahad, Nor Farhana Mohd Fazil, Ruslaini Nasir, Marzuki Isahak, Hasan Abu Samad. Profiling of morphine and codeine in urine after the ingestion of curry containing poppy seed as an evidence for opiates defence in Malaysia. Forensic science international. 2019 Sep; 302(?):109865. doi: 10.1016/j.forsciint.2019.06.023. [PMID: 31279278]
  • Amanda Spring de Almeida, Flávia Karine Rigo, Samira Dal-Toé De Prá, Alessandra Marcone Milioli, Diéssica Padilha Dalenogare, Gabriele Cheiran Pereira, Camila Dos Santos Ritter, Diulle Spat Peres, Caren Tatiane de David Antoniazzi, Carolina Stein, Rafael Noal Moresco, Sara Marchesan Oliveira, Gabriela Trevisan. Characterization of Cancer-Induced Nociception in a Murine Model of Breast Carcinoma. Cellular and molecular neurobiology. 2019 Jul; 39(5):605-617. doi: 10.1007/s10571-019-00666-8. [PMID: 30850915]
  • Jessica Winborn, Sarah Kerrigan. Analysis of Desomorphine in Urine Using Liquid Chromatography-Tandem Mass Spectrometry. Journal of analytical toxicology. 2019 Jun; 43(5):340-345. doi: 10.1093/jat/bky103. [PMID: 30590627]
  • Helen Radford, Karen H Simpson, Suzanne Rogerson, Mark I Johnson. A Single Site Population Study to Investigate CYP2D6 Phenotype of Patients with Persistent Non-Malignant Pain. Medicina (Kaunas, Lithuania). 2019 May; 55(6):. doi: 10.3390/medicina55060220. [PMID: 31141989]
  • Michael Böttcher, Stefan Lierheimer, Andreas Peschel, Olof Beck. Detection of heroin intake in patients in substitution treatment using oral fluid as specimen for drug testing. Drug and alcohol dependence. 2019 05; 198(?):136-139. doi: 10.1016/j.drugalcdep.2019.02.011. [PMID: 30927716]
  • Hossein Abdolmohammad-Zadeh, Abbasali Zamani, Zahra Shamsi. Preconcentration of morphine and codeine using a magnetite/reduced graphene oxide/silver nano-composite and their determination by high-performance liquid chromatography. Journal of chromatography. A. 2019 Apr; 1590(?):2-9. doi: 10.1016/j.chroma.2018.12.064. [PMID: 30606455]
  • Abbas Mohammadpour, Mahmood Dehghani Ashkezari, Behrokh Farahmand, Mohammad Shokrzadeh. Demographic Characteristics and Functional Performance of the Kidneys and Hearts of Patients with Acute Tramadol Toxicity. Drug research. 2019 Apr; 69(4):207-210. doi: 10.1055/a-0646-3918. [PMID: 29996175]
  • T Huertas, C Jurado, M Salguero, T Soriano, J Gamero. Stability studies in biological fluids during post-analysis custody. Opiate compounds derived from heroin consumption. Forensic science international. 2019 Apr; 297(?):326-334. doi: 10.1016/j.forsciint.2019.02.016. [PMID: 30852416]
  • Mehran Dastmalchi, Xue Chen, Jillian M Hagel, Limei Chang, Rongji Chen, Sukanya Ramasamy, Sam Yeaman, Peter J Facchini. Neopinone isomerase is involved in codeine and morphine biosynthesis in opium poppy. Nature chemical biology. 2019 04; 15(4):384-390. doi: 10.1038/s41589-019-0247-0. [PMID: 30886433]
  • Fabian Picht, Olof Beck, Michael Böttcher. Evaluation of an on-site test device for the heroin metabolite 6-acetylmorphine in urine. Drug testing and analysis. 2019 Mar; 11(3):536-540. doi: 10.1002/dta.2559. [PMID: 30569568]
  • Amir Nili-Ahmadabadi, Zahra Borzouee, Davoud Ahmadimoghaddam, Farzin Firozian, Dara Dastan. The occurrence of acetaminophen/codeine as an adulterant in herbal analgesic supplements in Hamadan, Iran: A pilot study. Complementary therapies in medicine. 2019 Feb; 42(?):223-225. doi: 10.1016/j.ctim.2018.11.018. [PMID: 30670245]
  • Jessica Winborn, Sarah Kerrigan. Quantitative analysis of desomorphine in blood and urine using solid phase extraction and gas chromatography-mass spectrometry. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2019 Feb; 1106-1107(?):43-49. doi: 10.1016/j.jchromb.2018.12.022. [PMID: 30640162]
  • Mark A Cervinski, Paul J Jannetto. A Question of Opioid Diversion or Compliance. Clinical chemistry. 2019 02; 65(2):236-240. doi: 10.1373/clinchem.2018.294140. [PMID: 30692135]
  • Hiroshi Yamazaki. [Message from the President of the Japanese Society for the Study of Xenobiotics]. Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan. 2019; 139(3):415-417. doi: 10.1248/yakushi.18-00186-5. [PMID: 30828021]
  • Alexander Fenwick, Alison Woodworth, Min Yu. An Unexpected Result of Meconium Drug Testing. Clinical chemistry. 2018 11; 64(11):1671-1672. doi: 10.1373/clinchem.2018.293209. [PMID: 30377181]
  • Cecilie Hasselø Thaulow, Åse Marit Leere Øiestad, Sidsel Rogde, Jannike Mørch Andersen, Gudrun Høiseth, Marte Handal, Jørg Mørland, Vigdis Vindenes. Can measurements of heroin metabolites in post-mortem matrices other than peripheral blood indicate if death was rapid or delayed?. Forensic science international. 2018 Sep; 290(?):121-128. doi: 10.1016/j.forsciint.2018.06.041. [PMID: 30015276]
  • Yeung-Ae Park, Greg Harris, Dov A Degen. Renal recovery in a dialysis-dependent patient with end-stage kidney disease secondary to analgesic nephropathy. Nephrology (Carlton, Vic.). 2018 07; 23(7):705-706. doi: 10.1111/nep.13171. [PMID: 30133974]
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  • Janelle O Poyant, Robert Albright, Jeremy Clain, Govind Pandompatam, Erin F Barreto. Extracorporeal elimination of butalbital in acute aspirin-butalbital-caffeine-codeine (Fiorinal with Codeine) poisoning. Clinical toxicology (Philadelphia, Pa.). 2018 06; 56(6):439-441. doi: 10.1080/15563650.2017.1400554. [PMID: 29124988]
  • Antonella Sorrentino, Silvia Trotta, Anna Pia Colucci, Lucia Aventaggiato, Andrea Marzullo, Biagio Solarino. Lethal endomyocarditis caused by chronic 'Krokodil' intoxication. Forensic science, medicine, and pathology. 2018 06; 14(2):229-235. doi: 10.1007/s12024-018-9967-9. [PMID: 29556967]
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  • Foroozan Hasanpour, Masoumeh Taei, Somayeh Tahmasebi. Ultra-sensitive electrochemical sensing of acetaminophen and codeine in biological fluids using CuO/CuFe2O4 nanoparticles as a novel electrocatalyst. Journal of food and drug analysis. 2018 04; 26(2):879-886. doi: 10.1016/j.jfda.2017.10.001. [PMID: 29567260]
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  • Abdu Subaihi, Howbeer Muhamadali, Shaun T Mutter, Ewan Blanch, David I Ellis, Royston Goodacre. Quantitative detection of codeine in human plasma using surface-enhanced Raman scattering via adaptation of the isotopic labelling principle. The Analyst. 2017 Mar; 142(7):1099-1105. doi: 10.1039/c7an00193b. [PMID: 28272603]
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