Doxepin (BioDeep_00000002430)

human metabolite blood metabolite Volatile Flavor Compounds

代谢物信息卡片

dimethyl(3-{9-oxatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,11,13-hexaen-2-ylidene}propyl)amine

化学式: C19H21NO (279.1623056)
中文名称: 多虑平, 多塞平
谱图信息: 最多检出来源 Homo sapiens(blood) 1.35%

Reviewed

Last reviewed on 2024-09-14.

Cite this Page

Doxepin. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/doxepin (retrieved 2024-11-22) (BioDeep RN: BioDeep_00000002430). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: CN(C)CC/C=C\1/c2ccccc2COc2ccccc12
InChI: InChI=1S/C19H21NO/c1-20(2)13-7-11-17-16-9-4-3-8-15(16)14-21-19-12-6-5-10-18(17)19/h3-6,8-12H,7,13-14H2,1-2H3

描述信息

Doxepin hydrochloride is a dibenzoxepin-derivative tricyclic antidepressant (TCA). TCAs are structurally similar to phenothiazines. They contain a tricyclic ring system with an alkyl amine substituent on the central ring. In non-depressed individuals, doxepin does not affect mood or arousal, but may cause sedation. In depressed individuals, doxepin exerts a positive effect on mood. TCAs are potent inhibitors of serotonin and norepinephrine reuptake. Tertiary amine TCAs, such as doxepin and amitriptyline, are more potent inhibitors of serotonin reuptake than secondary amine TCAs, such as nortriptyline and desipramine. TCAs also down-regulate cerebral cortical β-adrenergic receptors and sensitize post-synaptic serotonergic receptors with chronic use. The antidepressant effects of TCAs are thought to be due to an overall increase in serotonergic neurotransmission. TCAs also block histamine H₁ receptors, α₁-adrenergic receptors and muscarinic receptors, which accounts for their sedative, hypotensive and anticholinergic effects (e.g. blurred vision, dry mouth, constipation, urinary retention), respectively. Doxepin has less sedative and anticholinergic effects than amitriptyline. See toxicity section below for a complete listing of side effects. Doxepin may be used to treat depression and insomnia. Unlabeled indications include chronic and neuropathic pain, and anxiety. Doxepin may also be used as a second line agent to treat idiopathic urticaria.
D - Dermatologicals > D04 - Antipruritics, incl. antihistamines, anesthetics, etc. > D04A - Antipruritics, incl. antihistamines, anesthetics, etc.
N - Nervous system > N06 - Psychoanaleptics > N06A - Antidepressants > N06AA - Non-selective monoamine reuptake inhibitors
D002491 - Central Nervous System Agents > D002492 - Central Nervous System Depressants > D006993 - Hypnotics and Sedatives
C78272 - Agent Affecting Nervous System > C265 - Antidepressant Agent > C94727 - Tricyclic Antidepressant
D002491 - Central Nervous System Agents > D011619 - Psychotropic Drugs > D000928 - Antidepressive Agents
D018377 - Neurotransmitter Agents > D018494 - Histamine Agents > D006633 - Histamine Antagonists
EAWAG_UCHEM_ID 3676; CONFIDENCE standard compound
CONFIDENCE standard compound; EAWAG_UCHEM_ID 3676

同义名列表

31 个代谢物同义名

dimethyl(3-{9-oxatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,11,13-hexaen-2-ylidene}propyl)amine; Doxepin hydrochloride, cis-trans isomer mixture (approximately 1:5); 3-Dibenz[b,e]oxepin-11(6H)-ylidene-N,N-dimethyl-1-propanamine; Hydrochloride, doxepin; Doxepin hydrochloride; Novo-doxepin; Novo doxepin; Doxepin beta; Doxepin-RPH; Apo doxepin; Apo-doxepin; Doxepin RPH; ApoDoxepin; Cidoxepin; Prudoxin; Quitaxon; Doxepine; Doneurin; Sinequan; Sinquan; Desidox; Doxepia; doxepin; Deptran; Zonalon; Espadox; Mareen; Aponal; Xepin; Doxepin; Sinequan

数据库引用编号

33 个数据库交叉引用编号

ChEBI: CHEBI:36691
ChEBI: CHEBI:4710
KEGG: C06971
KEGGdrug: D07875
PubChem: 667477
PubChem: 667468
PubChem: 3158
HMDB: HMDB0015273
Metlin: METLIN2463
DrugBank: DB01142
DrugBank: DB14750
ChEMBL: CHEMBL1628227
ChEMBL: CHEMBL101740
ChEMBL: CHEMBL860
Wikipedia: Doxepin
MeSH: Doxepin
chemspider: 580850
CAS: 1668-19-5
MoNA: EQ367605
MoNA: EQ367603
MoNA: EQ367608
MoNA: EQ367602
MoNA: EQ367601
MoNA: EQ367609
MoNA: EQ367604
MoNA: EQ367606
MoNA: EQ367607
PMhub: MS000002591
PubChem: 9185
PDB-CCD: 5EH
NIKKAJI: J9.508G
RefMet: Doxepin
KNApSAcK: 4710

分类词条

代谢反应

1 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(1)

Doxepin Metabolism Pathway: Doxepin + Hydrogen Ion + NADPH + Oxygen ⟶ (E)-2-hydroxydoxepin + NADP + Water

PharmGKB(0)

1 个相关的物种来源信息

9606 - Homo sapiens: -

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

Huixin Tan, Fenghe Wang, Jiahuan Hu, Xiaoyan Duan, Wanting Bai, Xinbo Wang, Baolian Wang, Yan Su, Jinping Hu. Inhibitory interaction of flavonoids with organic cation transporter 2 and their structure-activity relationships for predicting nephroprotective effects. Journal of applied toxicology : JAT. 2023 Apr; ?(?):. doi: 10.1002/jat.4474. [PMID: 37057715]
Mengqi Zhang, Fengmin Huang, Feiyu Jiang, Meiting Mai, Xiaorou Guo, Ying Zhang, Ying Xu, Hengbing Zu. Clinical efficacy and safety of low-dose doxepin in Chinese patients with generalized anxiety disorder: A before-after study. Medicine. 2022 Oct; 101(42):e31201. doi: 10.1097/md.0000000000031201. [PMID: 36281170]
Binjie Zheng, Lulu Chen, Tiandong Zheng, Liping Hou, Xinyi Huang, Chao Li, Xintong Wang, Qing Fang, Jie Chen, Zhi Tang, Zhenyu Li, Dongsheng Ouyang. A novel solid phase extraction sample preparation method for sensitively determining doxepin and N-nordoxepin in human plasma and its application in a bioequivalence study in healthy Chinese volunteers. Analytical methods : advancing methods and applications. 2022 06; 14(22):2168-2178. doi: 10.1039/d2ay00129b. [PMID: 35608048]
Bridget Myers, Vidhatha Reddy, Stephanie Chan, Quinn Thibodeaux, Nicholas Brownstone, John Koo. Optimizing doxepin therapy in dermatology: introducing blood level monitoring and genotype testing. The Journal of dermatological treatment. 2022 Feb; 33(1):87-93. doi: 10.1080/09546634.2020.1762841. [PMID: 32347140]
Min Young Um, Minseok Yoon, Jaekwang Lee, Jonghoon Jung, Suengmok Cho. A Novel Potent Sleep-Promoting Effect of Turmeric: Turmeric Increases Non-Rapid Eye Movement Sleep in Mice Via Histamine H1Receptor Blockade. Molecular nutrition & food research. 2021 07; 65(14):e2100100. doi: 10.1002/mnfr.202100100. [PMID: 34003596]
Annelies Noorlander, Sebastiaan Wesseling, Ivonne M C M Rietjens, Bennard van Ravenzwaay. Incorporating renal excretion via the OCT2 transporter in physiologically based kinetic modelling to predict in vivo kinetics of mepiquat in rat. Toxicology letters. 2021 Jun; 343(?):34-43. doi: 10.1016/j.toxlet.2021.02.013. [PMID: 33639197]
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]
Shuai Ge, Xiangjun Wang, Yajing Hou, Yuexin Lv, Cheng Wang, Huaizhen He. Repositioning of histamine H1 receptor antagonist: Doxepin inhibits viropexis of SARS-CoV-2 Spike pseudovirus by blocking ACE2. European journal of pharmacology. 2021 Apr; 896(?):173897. doi: 10.1016/j.ejphar.2021.173897. [PMID: 33497607]
Narjes Saheb Sharif-Askari, Fatemeh Saheb Sharif-Askari, Bushra Mdkhana, Saba Al Heialy, Elaref Ratemi, Malak Alghamdi, Salah Abusnana, Tarek Kashour, Qutayba Hamid, Rabih Halwani. Effect of common medications on the expression of SARS-CoV-2 entry receptors in liver tissue. Archives of toxicology. 2020 12; 94(12):4037-4041. doi: 10.1007/s00204-020-02869-1. [PMID: 32808185]
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Hossein Salar Amoli, Yadollah Yamini, Hossein Darmani. Polyoxomolybdate368 /polyaniline nanocomposite as a novel fiber for solid-phase microextraction of antidepressant drugs in biological samples. Journal of separation science. 2020 Jul; 43(13):2636-2645. doi: 10.1002/jssc.201901152. [PMID: 32277789]
Zhenzhen Chen, Xiangyang Liu, Yanjin Luo, Junpei Wang, Yuhong Meng, Lei Sun, Yongsheng Chang, Qinghua Cui, Jichun Yang. Repurposing Doxepin to Ameliorate Steatosis and Hyperglycemia by Activating FAM3A Signaling Pathway. Diabetes. 2020 06; 69(6):1126-1139. doi: 10.2337/db19-1038. [PMID: 32312868]
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Sonia Bahrani, Mehrorang Ghaedi, Maryam Arabi. Construction of molecularly imprinted nanoparticles by employing ultrasound waves for selective determination of doxepin from human plasma samples: Modeling and optimization. Biomedical chromatography : BMC. 2019 Dec; 33(12):e4675. doi: 10.1002/bmc.4675. [PMID: 31378955]
Xingxing Meng, Zhenghui Gu, Xiaoping Xie, Yuting Su, Xi Zhang, Hongzhe Ma, Yibin Guo, Xincheng Liu, Yaoping Cheng, Yaoming Chang, Junxiang Bao. Acid sphingomyelinase mediates the noise-induced liver disorder in mice. Clinical and experimental pharmacology & physiology. 2019 06; 46(6):556-566. doi: 10.1111/1440-1681.13083. [PMID: 30854677]
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Christopher L Drake, Heith Durrence, Philip Cheng, Thomas Roth, Vivek Pillai, Edward L Peterson, Meeta Singh, Kieulinh Michelle Tran. Arousability and Fall Risk During Forced Awakenings From Nocturnal Sleep Among Healthy Males Following Administration of Zolpidem 10 mg and Doxepin 6 mg: A Randomized, Placebo-Controlled, Four-Way Crossover Trial. Sleep. 2017 07; 40(7):. doi: 10.1093/sleep/zsx086. [PMID: 28575467]
Maryam Shamsayei, Yadollah Yamini, Hamid Asiabi. Polythiophene/graphene oxide nanostructured electrodeposited coating for on-line electrochemically controlled in-tube solid-phase microextraction. Journal of chromatography. A. 2016 Dec; 1475(?):8-17. doi: 10.1016/j.chroma.2016.11.003. [PMID: 27836227]
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Yang Ye, Cunzhi Liu, Xuewei Liu, Shuming Huang. Ovariectomy changes the response to antidepressant drugs in tail suspension test in mice. Gynecological endocrinology : the official journal of the International Society of Gynecological Endocrinology. 2016 Dec; 32(12):986-990. doi: 10.1080/09513590.2016.1197197. [PMID: 27345718]
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Hirotoshi Sato, Chihiro Ito, Kotaro Hiraoka, Manabu Tashiro, Katsuhiko Shibuya, Yoshihito Funaki, Takeo Yoshikawa, Ren Iwata, Hiroo Matsuoka, Kazuhiko Yanai. Histamine H1 receptor occupancy by the new-generation antipsychotics olanzapine and quetiapine: a positron emission tomography study in healthy volunteers. Psychopharmacology. 2015 Oct; 232(19):3497-505. doi: 10.1007/s00213-015-4002-2. [PMID: 26146015]
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