Dextromethorphan (BioDeep_00000001457)

 

Secondary id: BioDeep_00000397774

human metabolite blood metabolite Chemicals and Drugs


代谢物信息卡片


(1R,9R,10R)-4-methoxy-17-methyl-17-azatetracyclo[7.5.3.0^{1,10}.0^{2,7}]heptadeca-2(7),3,5-triene

化学式: C18H25NO (271.1936)
中文名称: 左美沙芬, 右美沙芬
谱图信息: 最多检出来源 Homo sapiens(blood) 33.89%

分子结构信息

SMILES: CN1CCC23CCCCC2C1CC4=C3C=C(C=C4)OC
InChI: InChI=1S/C18H25NO/c1-19-10-9-18-8-4-3-5-15(18)17(19)11-13-6-7-14(20-2)12-16(13)18/h6-7,12,15,17H,3-5,8-11H2,1-2H3

描述信息

Dextromethorphan is an antitussive drug that is found in many over-the-counter cold and cough preparations, usually in the form of dextromethorphan hydrobromide. Dextromethorphan is a salt of the methyl ether dextrorotatory isomer of levorphanol, a narcotic analgesic. Dextromethorphan occurs as white crystals, is sparingly soluble in water, and freely soluble in alcohol. The drug is dextrorotatory in water (at 20 degrees Celsius, Sodium D-line) with a specific rotation of +27.6 degrees. Following oral administration, dextromethorphan is rapidly absorbed from the gastrointestinal tract, where it enters the bloodstream and crosses the blood-brain barrier. Dextromethorphan shows high affinity binding to several regions of the brain, including the medullary cough center. The first-pass through the hepatic portal vein results in some of the drug being metabolized into an active metabolite of dextromethorphan, dextrorphan, the 3-hydroxy derivative of dextromethorphan. The therapeutic activity of dextromethorphan is believed to be caused by both the drug and this metabolite. Dextromethorphan is predominantly metabolized by the liver, by various hepatic enzymes. Through various pathways, the drug undergoes (O-demethylation (which produces dextrorphan), N-demethylation, and partial conjugation with glucuronic acid and sulfate ions. The inactive metabolite (+)-3-hydroxy-N-methylmorphinan is formed as a product of DXM metabolism by these pathways. One well known metabolic catalyst involved is a specific cytochrome P450 enzyme known as 2D6, or CYP2D6. A significant portion of the population has a functional deficiency in this enzyme (and are known as poor CYP2D6 metabolizers). As CYP2D6 is the primary metabolic pathway in the inactivation of dextromethorphan, the duration of action and effects of dextromethorphan are significantly increased in such poor metabolizers. Deaths and hospitalizations have been reported in recreational use by poor CYP2D6 metabolizers. -- Wikipedia. This compound is an NMDA receptor antagonist (receptors, N-methyl-D-aspartate) and acts as a non-competitive channel blocker. It is also used to study the involvement of glutamate receptors in neurotoxicity. [PubChem]
Dextromethorphan is an antitussive drug that is found in many over-the-counter cold and cough preparations, usually in the form of dextromethorphan hydrobromide. Dextromethorphan is a salt of the methyl ether dextrorotatory isomer of levorphanol, a narcotic analgesic. Dextromethorphan occurs as white crystals, is sparingly soluble in water, and freely soluble in alcohol. The drug is dextrorotatory in water (at 20 degrees Celsius, Sodium D-line) with a specific rotation of +27.6 degrees. Following oral administration, dextromethorphan is rapidly absorbed from the gastrointestinal tract, where it enters the bloodstream and crosses the blood-brain barrier. The first-pass through the hepatic portal vein results in some of the drug being metabolized into an active metabolite of dextromethorphan, dextrorphan, the 3-hydroxy derivative of dextromethorphan. The therapeutic activity of dextromethorphan is believed to be caused by both the drug and this metabolite. Dextromethorphan is predominantly metabolized by the liver, by various hepatic enzymes. Through various pathways, the drug undergoes (O-demethylation (which produces dextrorphan), N-demethylation, and partial conjugation with glucuronic acid and sulfate ions. The inactive metabolite (+)-3-hydroxy-N-methylmorphinan is formed as a product of DXM metabolism by these pathways. One well known metabolic catalyst involved is a specific cytochrome P450 enzyme known as 2D6, or CYP2D6. A significant portion of the population has a functional deficiency in this enzyme (and are known as poor CYP2D6 metabolizers). As CYP2D6 is the primary metabolic pathway in the inactivation of dextromethorphan, the duration of action and effects of dextromethorphan are significantly increased in such poor metabolizers. Deaths and hospitalizations have been reported in recreational use by poor CYP2D6 metabolizers. -- Wikipedia [HMDB]
R - Respiratory system > R05 - Cough and cold preparations > R05D - Cough suppressants, excl. combinations with expectorants > R05DA - Opium alkaloids and derivatives
D018377 - Neurotransmitter Agents > D018683 - Excitatory Amino Acid Agents > D018691 - Excitatory Amino Acid Antagonists
D002492 - Central Nervous System Depressants > D009294 - Narcotics > D053610 - Opiate Alkaloids
C78272 - Agent Affecting Nervous System > C241 - Analgesic Agent > C2199 - Adjuvant Analgesic
C78272 - Agent Affecting Nervous System > C67413 - Opioid Receptor Agonist
D019141 - Respiratory System Agents > D000996 - Antitussive Agents
C78272 - Agent Affecting Nervous System > C241 - Analgesic Agent
D002491 - Central Nervous System Agents

同义名列表

91 个代谢物同义名

(1R,9R,10R)-4-methoxy-17-methyl-17-azatetracyclo[7.5.3.0^{1,10}.0^{2,7}]heptadeca-2(7),3,5-triene; Contac severe cold formula maximum strength; Dextromethorphan hydrobromide oros tablets; Dextromethorphan hydrobromide, monohydrate; Dextromethorphan hydrobromide, (+-)-isomer; Dextromethorphan Hydrobromide Monohydrate; Contac day & night cold/flu day caplets; Contac severe cold formula non-drowsy; Tylenol cough + decongestant liquid; Tylenol cold and flu no drowsiness; Tylenol cold and flu multi-symptom; Robitussin pediatric night relief; Robitussin maximum strength cough; Robitussin pediatric cough & cold; Tylenol flu no drowsiness gelcaps; (-)-3-Methoxy-17-methylmorphinan; Hydrochloride, dextromethorphan; (-)-3-Methoxy-N-methylmorphinan; Hydrobromide, dextromethorphan; L-3-Methoxy-17-methylmorphinan; Dextromethorphan hydrochloride; Bayer select head & chest cold; Contac nighttime cold medicine; Contac jr. non-drowsy formula; Dextromethorphan, (+-)-isomer; Dextromethorphan Hydrobromide; PediaCare cough-cold formula; Dextromethorphan bromhydrate; Bayer select night time cold; Drixoral cough & sore throat; Drixoral cough & congestion; Tylenol cold no drowsiness; Robitussin pediatric cough; D-Methorphan hydrobromide; Ornex severe cold formula; Dextromethorphan bromide; Robitussin cough calmers; Bayer select flu relief; Robitussin cold & cough; Endotussin-NN pediatric; Tussi-organidin DM-S NR; St. joseph cough syrup; Demorphan hydrobromide; Tussi-organidin DM NR; Tylenol cough liquid; Ru-tuss expectorant; Sudafed cough syrup; Levomethorphanum; Dextromethorphan; Dexyromethorphan; delta-Methorphan; Destrometerfano; Tussi-organidin; Chloraseptic DM; Dextrometorphan; Coricidin syrup; Levomethorphane; Drixoral cough; Racemethorphan; Levomethorphan; Prestwick_686; Robitussin DM; Endotussin-NN; DL-methorphan; Robitussin CF; Levometorfano; Dextromorphan; Δ-methorphan; D-Methorphan; L-Methorphan; PediaCare 1; Naldecon-DX; Dimetapp DM; Benylin DM; Orthoxicol; Demorphine; Triaminic; Tussar DM; Demorphan; Cerose-DM; Rondec DM; Methorate; Viro-med; Trind-DM; Dimacol; Cough-X; Romilar; Delsym; Hold; DXM; Dextromethorphan



数据库引用编号

27 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(8)

BioCyc(0)

PlantCyc(0)

代谢反应

70 个相关的代谢反应过程信息。

Reactome(70)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

1 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。

亚细胞结构定位 关联基因列表
Cytoplasm 9 ABCB1, CASP3, CYP1A1, CYP2A6, CYP2B6, CYP2C19, CYP2C8, CYP2C9, CYP2D7
Peripheral membrane protein 2 CYP1A1, CYP2B6
Endosome membrane 1 SLC6A4
Endoplasmic reticulum membrane 7 CYP1A1, CYP2A6, CYP2B6, CYP2C19, CYP2C8, CYP2C9, CYP3A5
Nucleus 1 CASP3
cytosol 3 AVP, CASP3, GPT
dendrite 3 AVP, DRD2, HTR1A
nucleoplasm 1 CASP3
Cell membrane 7 ABCB1, DRD2, GRID1, HTR1A, OPRD1, SLC6A4, TNF
Multi-pass membrane protein 7 ABCB1, CYP2D7, DRD2, GRID1, HTR1A, OPRD1, SLC6A4
Golgi apparatus membrane 1 DRD2
Synapse 3 DRD2, HTR1A, SLC6A4
cell surface 2 ABCB1, TNF
glutamatergic synapse 3 CASP3, DRD2, GRID1
Golgi membrane 2 DRD2, INS
mitochondrial inner membrane 1 CYP1A1
neuronal cell body 2 CASP3, TNF
presynaptic membrane 3 DRD2, OPRD1, SLC6A4
Presynapse 1 SLC6A4
acrosomal vesicle 1 DRD2
plasma membrane 10 ABCB1, CYP2C19, CYP2C8, CYP2C9, DRD2, GRID1, HTR1A, OPRD1, SLC6A4, TNF
synaptic vesicle membrane 2 DRD2, OPRD1
Membrane 6 ABCB1, CYP2A6, CYP2D7, CYP3A5, OPRD1, SLC6A4
apical plasma membrane 1 ABCB1
axon 1 DRD2
extracellular exosome 3 ABCB1, GPT, GRID1
extracellular space 4 AVP, IL6, INS, TNF
mitochondrion 2 CYP1A1, CYP2D7
intracellular membrane-bounded organelle 8 CYP1A1, CYP2A6, CYP2B6, CYP2C19, CYP2C8, CYP2C9, CYP2D7, CYP3A5
Microsome membrane 4 CYP1A1, CYP2B6, CYP2C9, CYP3A5
postsynaptic density 1 CASP3
Secreted 3 AVP, IL6, INS
extracellular region 4 AVP, IL6, INS, TNF
ciliary membrane 1 DRD2
external side of plasma membrane 1 TNF
dendritic spine 1 DRD2
perikaryon 1 DRD2
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
postsynaptic membrane 3 DRD2, GRID1, SLC6A4
Apical cell membrane 1 ABCB1
Mitochondrion inner membrane 1 CYP1A1
Membrane raft 2 SLC6A4, TNF
Cell junction, focal adhesion 1 SLC6A4
focal adhesion 1 SLC6A4
GABA-ergic synapse 2 DRD2, GRID1
secretory granule 1 AVP
lateral plasma membrane 1 DRD2
Postsynaptic cell membrane 1 GRID1
Cell projection, neuron projection 1 SLC6A4
neuron projection 2 OPRD1, SLC6A4
cilium 1 DRD2
phagocytic cup 1 TNF
non-motile cilium 1 DRD2
sperm flagellum 1 DRD2
Endomembrane system 1 SLC6A4
endosome lumen 1 INS
Cell projection, dendrite 1 HTR1A
secretory granule lumen 1 INS
Golgi lumen 1 INS
endoplasmic reticulum lumen 2 IL6, INS
axon terminus 2 DRD2, OPRD1
endocytic vesicle 1 DRD2
transport vesicle 1 INS
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
postsynaptic density membrane 2 GRID1, OPRD1
neuronal dense core vesicle 2 AVP, OPRD1
clathrin-coated endocytic vesicle membrane 1 AVP
cytoplasmic microtubule 1 CYP2A6
external side of apical plasma membrane 1 ABCB1
death-inducing signaling complex 1 CASP3
dopaminergic synapse 1 DRD2
dendrite membrane 1 OPRD1
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
interleukin-6 receptor complex 1 IL6
G protein-coupled receptor complex 1 DRD2
serotonergic synapse 1 SLC6A4
spine apparatus 1 OPRD1
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


文献列表

  • Rakshit S Tanna, James T Nguyen, Deena L Hadi, Matthew E Layton, John R White, Nadja B Cech, Nicholas H Oberlies, Allan E Rettie, Kenneth E Thummel, Mary F Paine. Clinical Assessment of the Drug Interaction Potential of the Psychotropic Natural Product Kratom. Clinical pharmacology and therapeutics. 2023 Mar; ?(?):. doi: 10.1002/cpt.2891. [PMID: 36924284]
  • Shu-Juan Xu, Hao Guo, Long Jin, Zi-Xin Liu, Gao-Jie Xin, Yue You, Wei Hao, Jian-Hua Fu, Jian-Xun Liu. [Effect of Jinzhen Oral Liquid on cough after lipopolysaccharide-induced infection in rats and mechanism]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2022 Sep; 47(17):4707-4714. doi: 10.19540/j.cnki.cjcmm.20220119.701. [PMID: 36164878]
  • Seok Hwee Koo, Gaik Hong Soon, Alain Pruvost, Henri Benech, Tiing Leong Ang, Edmund Jon Deoon Lee, Daphne Shih Wen Ang. Evaluation of a six-probe cocktail (caffeine, tolbutamide, omeprazole, dextromethorphan, midazolam, and digoxin) approach to estimate hepatic drug detoxification capability and dosage requirements after a single oral dosing in healthy Chinese volunteers. Naunyn-Schmiedeberg's archives of pharmacology. 2022 07; 395(7):815-826. doi: 10.1007/s00210-022-02235-1. [PMID: 35394133]
  • Sara Shum, Aprajita Yadav, Emily Fay, Sue Moreni, Jennie Mao, Lindsay Czuba, Celine Wang, Nina Isoherranen, Mary F Hebert. Infant Dextromethorphan and Dextrorphan Exposure via Breast Milk From Mothers Who Are CYP2D6 Extensive Metabolizers. Journal of clinical pharmacology. 2022 06; 62(6):747-755. doi: 10.1002/jcph.2012. [PMID: 34889461]
  • Indrani Sarkar, Arnab Sen. In silico screening predicts common cold drug Dextromethorphan along with Prednisolone and Dexamethasone can be effective against novel Coronavirus disease (COVID-19). Journal of biomolecular structure & dynamics. 2022 05; 40(8):3706-3710. doi: 10.1080/07391102.2020.1850528. [PMID: 33225870]
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  • Yu-Hua Shi, Qin-Wei Huang, She-Min Zhu, Yue-Mei Zhou, Li-Jiang Zhang, Wen-Kang Huang, Jin-Jin Shao, Jian-Liang Zhou, Wen-Ting Zhang. Chemical profiling of Fritillariae thunbergii Miq prepared by different processing methods reveals two new quality markers: Zhebeininoside and imperialine-3-β-D-glucoside. Journal of ethnopharmacology. 2022 Jan; 283(?):114670. doi: 10.1016/j.jep.2021.114670. [PMID: 34653522]
  • En-Shao Liu, Nai-Ching Chen, Tzu-Ming Jao, Chien-Liang Chen. Dextromethorphan Reduces Oxidative Stress and Inhibits Uremic Artery Calcification. International journal of molecular sciences. 2021 Nov; 22(22):. doi: 10.3390/ijms222212277. [PMID: 34830159]
  • Tae Woo Jung, Eui Jin Hwang, Do Hyeon Pyun, Tae Jin Kim, Hyun Jung Lee, A M Abd El-Aty, Joon Seok Bang, Hyoung-Chun Kim, Ji Hoon Jeong. 3-hydroxymorphinan enhances mitochondrial biogenesis and adipocyte browning through AMPK-dependent pathway. Biochemical and biophysical research communications. 2021 11; 577(?):17-23. doi: 10.1016/j.bbrc.2021.08.083. [PMID: 34487960]
  • Xiaoshu Dai, Michael D Karol, Matthew Hitron, Marjie L Hard, Matthew T Goulet, Colleen F McLaughlin, Scott J Brantley. Napabucasin Drug-Drug Interaction Potential, Safety, Tolerability, and Pharmacokinetics Following Oral Dosing in Healthy Adult Volunteers. Clinical pharmacology in drug development. 2021 08; 10(8):824-839. doi: 10.1002/cpdd.961. [PMID: 34107166]
  • A David Rodrigues, Madelé van Dyk, Michael J Sorich, Alia Fahmy, Zivile Useckaite, Lauren A Newman, Asha J Kapetas, Reham Mounzer, Linda S Wood, Jillian G Johnson, Andrew Rowland. Exploring the Use of Serum-Derived Small Extracellular Vesicles as Liquid Biopsy to Study the Induction of Hepatic Cytochromes P450 and Organic Anion Transporting Polypeptides. Clinical pharmacology and therapeutics. 2021 07; 110(1):248-258. doi: 10.1002/cpt.2244. [PMID: 33792897]
  • Pierre Baumann, Gilles Bertschy, Fritz Ramseier, Rico Nil. Plasma Concentrations and Cardiovascular Effects of Citalopram Enantiomers After Oral Versus Infusion Citalopram Therapy in Dextromethorphan-Mephenytoin-Phenotyped Patients With Major Depression. Therapeutic drug monitoring. 2021 06; 43(3):436-442. doi: 10.1097/ftd.0000000000000824. [PMID: 33060488]
  • Mark J Henderson, Kathleen A Trychta, Shyh-Ming Yang, Susanne Bäck, Adam Yasgar, Emily S Wires, Carina Danchik, Xiaokang Yan, Hideaki Yano, Lei Shi, Kuo-Jen Wu, Amy Q Wang, Dingyin Tao, Gergely Zahoránszky-Kőhalmi, Xin Hu, Xin Xu, David Maloney, Alexey V Zakharov, Ganesha Rai, Fumihiko Urano, Mikko Airavaara, Oksana Gavrilova, Ajit Jadhav, Yun Wang, Anton Simeonov, Brandon K Harvey. A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome. Cell reports. 2021 04; 35(4):109040. doi: 10.1016/j.celrep.2021.109040. [PMID: 33910017]
  • Youyi Peng, Qiang Zhang, William J Welsh. Novel Sigma 1 Receptor Antagonists as Potential Therapeutics for Pain Management. Journal of medicinal chemistry. 2021 01; 64(1):890-904. doi: 10.1021/acs.jmedchem.0c01964. [PMID: 33372782]
  • Motoyasu Miura, Shimako Tanaka, Shinya Uchida, Chiaki Kamiya, Naoki Katayama, Akio Hakamata, Keiichi Odagiri, Naoki Inui, Junichi Kawakami, Hiroshi Watanabe, Noriyuki Namiki. Prediction of the Area under the Curve Using Limited-Point Blood Sampling in a Cocktail Study to Assess Multiple CYP Activities. Biological & pharmaceutical bulletin. 2021; 44(6):762-770. doi: 10.1248/bpb.b20-00691. [PMID: 34078808]
  • Rakshit S Tanna, Dan-Dan Tian, Nadja B Cech, Nicholas H Oberlies, Allan E Rettie, Kenneth E Thummel, Mary F Paine. Refined Prediction of Pharmacokinetic Kratom-Drug Interactions: Time-Dependent Inhibition Considerations. The Journal of pharmacology and experimental therapeutics. 2021 01; 376(1):64-73. doi: 10.1124/jpet.120.000270. [PMID: 33093187]
  • Preeti Pandey, Kartikay Prasad, Amresh Prakash, Vijay Kumar. Insights into the biased activity of dextromethorphan and haloperidol towards SARS-CoV-2 NSP6: in silico binding mechanistic analysis. Journal of molecular medicine (Berlin, Germany). 2020 12; 98(12):1659-1673. doi: 10.1007/s00109-020-01980-1. [PMID: 32965508]
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