Amodiaquine (BioDeep_00000001888)

 

Secondary id: BioDeep_00001867811

human metabolite blood metabolite Chemicals and Drugs


代谢物信息卡片


4-[(7-chloroquinolin-4-yl)amino]-2-[(diethylamino)methyl]phenol

化学式: C20H22ClN3O (355.1451)
中文名称: 阿莫地喹
谱图信息: 最多检出来源 Mentha canadensis(plant) 33.96%

分子结构信息

SMILES: CCN(CC)CC1=C(C=CC(=C1)NC2=C3C=CC(=CC3=NC=C2)Cl)O
InChI: InChI=1S/C20H22ClN3O/c1-3-24(4-2)13-14-11-16(6-8-20(14)25)23-18-9-10-22-19-12-15(21)5-7-17(18)19/h5-12,25H,3-4,13H2,1-2H3,(H,22,23)

描述信息

Amodiaquine is only found in individuals that have used or taken this drug. It is a 4-aminoquinoquinoline compound with anti-inflammatory properties. [PubChem]The mechanism of plasmodicidal action of amodiaquine is not completely certain. Like other quinoline derivatives, it is thought to inhibit heme polymerase activity. This results in accumulation of free heme, which is toxic to the parasites. The drug binds the free heme preventing the parasite from converting it to a form less toxic. This drug-heme complex is toxic and disrupts membrane function.
P - Antiparasitic products, insecticides and repellents > P01 - Antiprotozoals > P01B - Antimalarials > P01BA - Aminoquinolines
D000890 - Anti-Infective Agents > D000977 - Antiparasitic Agents > D000981 - Antiprotozoal Agents
C254 - Anti-Infective Agent > C276 - Antiparasitic Agent > C277 - Antiprotozoal Agent

同义名列表

15 个代谢物同义名

4-[(7-chloroquinolin-4-yl)amino]-2-[(diethylamino)methyl]phenol; Roussel brand OF amodiaquine hydrochloride; Hydrochloride, amodiaquine; Amodiaquine hydrochloride; Amodiaquine, ring-closed; Amodiaquine usp24; Amodiaquinum; Amodiaquina; amodiaquine; Flavoquine; Amodiaquin; Amodiachin; Camoquine; Camoquin; Amodiaquine



数据库引用编号

19 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(1)

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)

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 11 ABCB1, CYP2C19, CYP2C8, CYP2C9, CYP2D6, CYP3A4, DHFR, DHPS, G6PD, HNMT, NR4A2
Peripheral membrane protein 2 CYP1B1, G6PD
Endoplasmic reticulum membrane 7 CYP1A2, CYP1B1, CYP2C19, CYP2C8, CYP2C9, CYP2D6, CYP3A4
Nucleus 2 MPO, NR4A2
cytosol 6 DHFR, DHPS, G6PD, GPT, HNMT, SLC22A16
centrosome 1 HNMT
nucleoplasm 3 HNMT, MPO, NR4A2
Cell membrane 6 ABCB1, CD8A, CTLA4, PDCD1, SCN2A, SLC22A16
Multi-pass membrane protein 3 ABCB1, SCN2A, SLC22A16
cell surface 1 ABCB1
glutamatergic synapse 1 SCN2A
Golgi apparatus 1 CTLA4
presynaptic membrane 1 SCN2A
Cytoplasm, cytosol 1 G6PD
Lysosome 1 MPO
plasma membrane 9 ABCB1, CD8A, CTLA4, CYP2C19, CYP2C8, CYP2C9, PDCD1, SCN2A, SLC22A16
Membrane 8 ABCB1, CYP1B1, CYP2D6, CYP3A4, G6PD, PDCD1, SCN2A, SLC22A16
apical plasma membrane 1 ABCB1
axon 1 SCN2A
extracellular exosome 5 ABCB1, G6PD, GPT, HNMT, MPO
endoplasmic reticulum 1 CYP2D6
extracellular space 1 MPO
perinuclear region of cytoplasm 1 CTLA4
intercalated disc 1 SCN2A
mitochondrion 3 CYP1B1, CYP2D6, DHFR
protein-containing complex 1 NR4A2
intracellular membrane-bounded organelle 9 CYP1A2, CYP1B1, CYP2C19, CYP2C8, CYP2C9, CYP2D6, CYP3A4, G6PD, MPO
Microsome membrane 5 CYP1A2, CYP1B1, CYP2C9, CYP2D6, CYP3A4
Single-pass type I membrane protein 2 CD8A, CTLA4
extracellular region 2 CD8A, MPO
cytoplasmic side of plasma membrane 1 G6PD
Single-pass membrane protein 1 CYP2D6
[Isoform 2]: Secreted 1 CD8A
transcription regulator complex 1 NR4A2
centriolar satellite 1 G6PD
external side of plasma membrane 3 CD8A, CTLA4, PDCD1
T-tubule 1 SCN2A
Apical cell membrane 1 ABCB1
secretory granule 1 MPO
nuclear speck 1 NR4A2
receptor complex 1 CD8A
chromatin 1 NR4A2
azurophil granule 1 MPO
plasma membrane raft 1 CD8A
node of Ranvier 1 SCN2A
paranode region of axon 1 SCN2A
azurophil granule lumen 1 MPO
clathrin-coated endocytic vesicle 1 CTLA4
phagocytic vesicle lumen 1 MPO
external side of apical plasma membrane 1 ABCB1
[Isoform 1]: Cell membrane 1 CD8A
voltage-gated sodium channel complex 1 SCN2A
T cell receptor complex 1 CD8A
protein complex involved in cell adhesion 1 CTLA4


文献列表

  • Stephan Chalon, M Farouk Chughlay, Nada Abla, Andre Marie Tchouatieu, Amina Haouala, Ben Hutter, Ulrike Lorch, Fiona Macintyre. Unanticipated CNS Safety Signal in a Placebo-Controlled, Randomized Trial of Co-Administered Atovaquone-Proguanil and Amodiaquine. Clinical pharmacology and therapeutics. 2022 04; 111(4):867-877. doi: 10.1002/cpt.2404. [PMID: 34453327]
  • Jingqi Qian, Mian Wang, Zhaoxiang Wang, Rui Feng, Jiaqi Zhang, Chencheng Ye, Man Zhang, Baomin Wang, Liwang Cui. Development of single- and multiplex immunoassays for rapid detection and quantitation of amodiaquine in ACT drugs and rat serum. Analytical and bioanalytical chemistry. 2022 Feb; 414(4):1631-1640. doi: 10.1007/s00216-021-03787-6. [PMID: 34846541]
  • Abdullahi Tsanni. African scientists race to test COVID drugs - but face major hurdles. Nature. 2021 11; 599(7883):25-27. doi: 10.1038/d41586-021-02995-5. [PMID: 34732862]
  • Karnrawee Kaewkhao, Joel Tarning, Daniel Blessborn. High-throughput quantitation method for amodiaquine and desethylamodiaquine in plasma using supported liquid extraction technology. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2021 Aug; 1179(?):122887. doi: 10.1016/j.jchromb.2021.122887. [PMID: 34364298]
  • Aida N Kawuma, Stephen I Walimbwa, Goonaseelan Colin Pillai, Saye Khoo, Mohammed Lamorde, Roeland E Wasmann, Paolo Denti. Dolutegravir pharmacokinetics during co-administration with either artemether/lumefantrine or artesunate/amodiaquine. The Journal of antimicrobial chemotherapy. 2021 04; 76(5):1269-1272. doi: 10.1093/jac/dkab022. [PMID: 33550391]
  • Neils Ben Quashie, Nancy Odurowah Duah-Quashie. Treatment of COVID-19 with Chloroquine: Implication for Malaria Chemotherapy Using ACTs in Disease Endemic Countries. Journal of tropical pediatrics. 2021 01; 67(1):. doi: 10.1093/tropej/fmaa089. [PMID: 33367880]
  • Yujeong Choi, Eun Goo Lee, Gibbeum Lee, Mi Gyeong Jeong, Hyo Kyeong Kim, Ji-Hyun Oh, Sung Won Kwon, Eun Sook Hwang. Amodiaquine promotes testosterone production and de novo synthesis of cholesterol and triglycerides in Leydig cells. Journal of lipid research. 2021; 62(?):100152. doi: 10.1016/j.jlr.2021.100152. [PMID: 34808194]
  • Mathieu Gendrot, Isabelle Duflot, Manon Boxberger, Océane Delandre, Priscilla Jardot, Marion Le Bideau, Julien Andreani, Isabelle Fonta, Joel Mosnier, Clara Rolland, Sébastien Hutter, Bernard La Scola, Bruno Pradines. Antimalarial artemisinin-based combination therapies (ACT) and COVID-19 in Africa: In vitro inhibition of SARS-CoV-2 replication by mefloquine-artesunate. International journal of infectious diseases : IJID : official publication of the International Society for Infectious Diseases. 2020 Oct; 99(?):437-440. doi: 10.1016/j.ijid.2020.08.032. [PMID: 32805422]
  • Jun Mo Kang, Hyun Seob Lee, Junghyun Kim, Dong Ho Yang, Hye Yun Jeong, Yu Ho Lee, Dong Jin Kim, Seon Hwa Park, MinJi Sung, Jaehee Kim, Hyun Ju An, Sang Ho Lee, So Young Lee. Beneficial Effect of Chloroquine and Amodiaquine on Type 1 Diabetic Tubulopathy by Attenuating Mitochondrial Nox4 and Endoplasmic Reticulum Stress. Journal of Korean medical science. 2020 Sep; 35(36):e305. doi: 10.3346/jkms.2020.35.e305. [PMID: 32924342]
  • Fabrice A Somé, Thomas Bazié, Hanna Y Ehrlich, Justin Goodwin, Aine Lehane, Catherine Neya, Kabré Zachari, Martina Wade, Jean-Marie Ouattara, Brian D Foy, Roch K Dabiré, Sunil Parikh, Jean-Bosco Ouédraogo. Investigating selected host and parasite factors potentially impacting upon seasonal malaria chemoprevention in Bama, Burkina Faso. Malaria journal. 2020 Jul; 19(1):238. doi: 10.1186/s12936-020-03311-8. [PMID: 32631416]
  • Aleksandr Ianevski, Rouan Yao, Mona Høysæter Fenstad, Svetlana Biza, Eva Zusinaite, Tuuli Reisberg, Hilde Lysvand, Kirsti Løseth, Veslemøy Malm Landsem, Janne Fossum Malmring, Valentyn Oksenych, Sten Even Erlandsen, Per Arne Aas, Lars Hagen, Caroline H Pettersen, Tanel Tenson, Jan Egil Afset, Svein Arne Nordbø, Magnar Bjørås, Denis E Kainov. Potential Antiviral Options against SARS-CoV-2 Infection. Viruses. 2020 06; 12(6):. doi: 10.3390/v12060642. [PMID: 32545799]
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  • Mohamed Hagar, Hoda A Ahmed, Ghadah Aljohani, Omaima A Alhaddad. Investigation of Some Antiviral N-Heterocycles as COVID 19 Drug: Molecular Docking and DFT Calculations. International journal of molecular sciences. 2020 May; 21(11):. doi: 10.3390/ijms21113922. [PMID: 32486229]
  • Gergő Dargó, Dávid Bajusz, Kristóf Simon, Judit Müller, György T Balogh. Human Serum Albumin Binding in a Vial: A Novel UV-pH Titration Method To Assist Drug Design. Journal of medicinal chemistry. 2020 02; 63(4):1763-1774. doi: 10.1021/acs.jmedchem.0c00046. [PMID: 31995375]
  • Chu Xuan Anh, Marina Chavchich, Geoffrey W Birrell, Karin Van Breda, Thomas Travers, Kerryn Rowcliffe, Anton R Lord, G Dennis Shanks, Michael D Edstein. Pharmacokinetics and Ex Vivo Antimalarial Activity of Artesunate-Amodiaquine plus Methylene Blue in Healthy Volunteers. Antimicrobial agents and chemotherapy. 2020 02; 64(3):. doi: 10.1128/aac.01441-19. [PMID: 31907186]
  • Awodayo O Adepiti, Babatunde A Adeagbo, Ayorinde Adehin, Oluseye O Bolaji, Anthony A Elujoba. Influence of MAMA decoction, an Herbal Antimalarial, on the Pharmacokinetics of Amodiaquine in Mice. European journal of drug metabolism and pharmacokinetics. 2020 Feb; 45(1):81-88. doi: 10.1007/s13318-019-00583-7. [PMID: 31642009]
  • Lisa Evans DeWald, Joshua C Johnson, Dawn M Gerhardt, Lisa M Torzewski, Elena Postnikova, Anna N Honko, Krisztina Janosko, Louis Huzella, William E Dowling, Ann E Eakin, Blaire L Osborn, Janet Gahagen, Liang Tang, Carol E Green, Jon C Mirsalis, Michael R Holbrook, Peter B Jahrling, Julie Dyall, Lisa E Hensley. In Vivo Activity of Amodiaquine against Ebola Virus Infection. Scientific reports. 2019 12; 9(1):20199. doi: 10.1038/s41598-019-56481-0. [PMID: 31882748]
  • Abdel Jelil Njouendou, Chi Anizette Kien, Mathias E Esum, Manuel Ritter, Winston Patrick Chounna Ndongmo, Fanny Fri Fombad, Narcisse Victor T Gandjui, Flobert Njiokou, Peter Enyong, Kenneth Pfarr, Joseph Turner, Laura E Layland, Achim Hoerauf, Samuel Wanji. In vitro maintenance of Mansonella perstans microfilariae and its relevance for drug screening. Experimental parasitology. 2019 Nov; 206(?):107769. doi: 10.1016/j.exppara.2019.107769. [PMID: 31580876]
  • James S Lee, Neill K J Adhikari, Henry Y Kwon, Koren Teo, Reed Siemieniuk, François Lamontagne, Adrienne Chan, Sharmistha Mishra, Srinivas Murthy, Peter Kiiza, Jan Hajek, Elhadj I Bah, Marie-Claire Lamah, Raymond Kao, Robert A Fowler. Anti-Ebola therapy for patients with Ebola virus disease: a systematic review. BMC infectious diseases. 2019 May; 19(1):376. doi: 10.1186/s12879-019-3980-9. [PMID: 31046707]
  • Tirivashe Elton Chiwunze, Venkata Narayana Palakollu, Atal A S Gill, Francis Kayamba, Neeta Bachheti Thapliyal, Rajshekhar Karpoormath. A highly dispersed multi-walled carbon nanotubes and poly(methyl orange) based electrochemical sensor for the determination of an anti-malarial drug: Amodiaquine. Materials science & engineering. C, Materials for biological applications. 2019 Apr; 97(?):285-292. doi: 10.1016/j.msec.2018.12.018. [PMID: 30678913]
  • Jérôme Munyangi, Lucile Cornet-Vernet, Michel Idumbo, Chen Lu, Pierre Lutgen, Christian Perronne, Nadège Ngombe, Jacques Bianga, Bavon Mupenda, Paul Lalukala, Guy Mergeai, Dieudonné Mumba, Melissa Towler, Pamela Weathers. Artemisia annua and Artemisia afra tea infusions vs. artesunate-amodiaquine (ASAQ) in treating Plasmodium falciparum malaria in a large scale, double blind, randomized clinical trial. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2019 Apr; 57(?):49-56. doi: 10.1016/j.phymed.2018.12.002. [PMID: 30668322]
  • Stephen I Walimbwa, Mohammed Lamorde, Catriona Waitt, Julian Kaboggoza, Laura Else, Pauline Byakika-Kibwika, Alieu Amara, Joshua Gini, Markus Winterberg, Justin Chiong, Joel Tarning, Saye H Khoo. Drug Interactions between Dolutegravir and Artemether-Lumefantrine or Artesunate-Amodiaquine. Antimicrobial agents and chemotherapy. 2019 02; 63(2):. doi: 10.1128/aac.01310-18. [PMID: 30420479]
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  • Ali Mohamed Ali, Melissa A Penny, Thomas A Smith, Lesley Workman, Philip Sasi, George O Adjei, Francesca Aweeka, Jean-René Kiechel, Vincent Jullien, Marcus J Rijken, Rose McGready, Julia Mwesigwa, Kim Kristensen, Kasia Stepniewska, Joel Tarning, Karen I Barnes, Paolo Denti. Population Pharmacokinetics of the Antimalarial Amodiaquine: a Pooled Analysis To Optimize Dosing. Antimicrobial agents and chemotherapy. 2018 10; 62(10):. doi: 10.1128/aac.02193-17. [PMID: 30038039]
  • Nguyen Ngoc Quang, Marina Chavchich, Chu Xuan Anh, Geoffrey W Birrell, Karin van Breda, Thomas Travers, Kerryn Rowcliffe, Michael D Edstein. Comparison of the Pharmacokinetics and Ex Vivo Antimalarial Activities of Artesunate-Amodiaquine and Artemisinin-Piperaquine in Healthy Volunteers for Preselection Malaria Therapy. The American journal of tropical medicine and hygiene. 2018 07; 99(1):65-72. doi: 10.4269/ajtmh.17-0434. [PMID: 29741150]
  • Hoe-Yune Jung, Bobae Kim, Hye Guk Ryu, Yosep Ji, Soyoung Park, Seung Hee Choi, Dohyun Lee, In-Kyu Lee, Munki Kim, You Jeong Lee, Woojin Song, Young Hee Lee, Hyung Jin Choi, Chang-Kee Hyun, Wilhelm H Holzapfel, Kyong-Tai Kim. Amodiaquine improves insulin resistance and lipid metabolism in diabetic model mice. Diabetes, obesity & metabolism. 2018 07; 20(7):1688-1701. doi: 10.1111/dom.13284. [PMID: 29516607]
  • Hye Yun Jeong, Jun Mo Kang, Hak Hoon Jun, Dong-Jin Kim, Seon Hwa Park, Min Ji Sung, Jin Hyung Heo, Dong Ho Yang, Sang Ho Lee, So-Young Lee. Chloroquine and amodiaquine enhance AMPK phosphorylation and improve mitochondrial fragmentation in diabetic tubulopathy. Scientific reports. 2018 06; 8(1):8774. doi: 10.1038/s41598-018-26858-8. [PMID: 29884802]
  • Alassane Dicko, Michelle E Roh, Halimatou Diawara, Almahamoudou Mahamar, Harouna M Soumare, Kjerstin Lanke, John Bradley, Koualy Sanogo, Daouda T Kone, Kalifa Diarra, Sekouba Keita, Djibrilla Issiaka, Sekou F Traore, Charles McCulloch, Will J R Stone, Jimee Hwang, Olaf Müller, Joelle M Brown, Vinay Srinivasan, Chris Drakeley, Roly Gosling, Ingrid Chen, Teun Bousema. Efficacy and safety of primaquine and methylene blue for prevention of Plasmodium falciparum transmission in Mali: a phase 2, single-blind, randomised controlled trial. The Lancet. Infectious diseases. 2018 06; 18(6):627-639. doi: 10.1016/s1473-3099(18)30044-6. [PMID: 29422384]
  • Sarah M Tindall, Cindy Vallières, Dev H Lakhani, Farida Islahudin, Kang-Nee Ting, Simon V Avery. Heterologous Expression of a Novel Drug Transporter from the Malaria Parasite Alters Resistance to Quinoline Antimalarials. Scientific reports. 2018 02; 8(1):2464. doi: 10.1038/s41598-018-20816-0. [PMID: 29410428]
  • Tae Hee Kim, Hyo Kyeong Kim, Eun Sook Hwang. Novel anti-adipogenic activity of anti-malarial amodiaquine through suppression of PPARγ activity. Archives of pharmacal research. 2017 Nov; 40(11):1336-1343. doi: 10.1007/s12272-017-0965-3. [PMID: 29071567]
  • Ahmed A Albassam, Reginald F Frye, John S Markowitz. The effect of milk thistle (Silybum marianum) and its main flavonolignans on CYP2C8 enzyme activity in human liver microsomes. Chemico-biological interactions. 2017 Jun; 271(?):24-29. doi: 10.1016/j.cbi.2017.04.025. [PMID: 28457856]
  • Awodayo O Adepiti, Ezekiel O Iwalewa. Evaluation of the combination of Uvaria chamae (P. Beauv.) and amodiaquine in murine malaria. Journal of ethnopharmacology. 2016 Dec; 193(?):30-35. doi: 10.1016/j.jep.2016.07.035. [PMID: 27416806]
  • Awodayo O Adepiti, Anthony A Elujoba, Oluseye O Bolaji. Evaluation of herbal antimalarial MAMA decoction-amodiaquine combination in murine malaria model. Pharmaceutical biology. 2016 Oct; 54(10):2298-303. doi: 10.3109/13880209.2016.1155626. [PMID: 27057621]
  • Feng Liu, Ping Cai, Imir Metushi, Jinze Li, Tetsuya Nakayawa, Libia Vega, Jack Uetrecht. Exploring an animal model of amodiaquine-induced liver injury in rats and mice. Journal of immunotoxicology. 2016 09; 13(5):694-712. doi: 10.3109/1547691x.2016.1166167. [PMID: 27416278]
  • Dhiraj M Rathod, Keyur R Patel, Hiren N Mistri, Arvind G Jangid, Pranav S Shrivastav, Mallika Sanyal. Application of an LC-MS/MS method for reliable determination of amodiaquine, N-desethylamodiaquine, artesunate and dihydroartemisinin in human plasma for a bioequivalence study in healthy Indian subjects. Journal of pharmaceutical and biomedical analysis. 2016 May; 124(?):67-78. doi: 10.1016/j.jpba.2016.02.021. [PMID: 26930583]
  • Lawrence G Febir, Kwaku Poku Asante, Samuel Afari-Asiedu, Livesy N Abokyi, Anthony Kwarteng, Bernhards Ogutu, Margaret Gyapong, Seth Owusu-Agyei. Seeking treatment for uncomplicated malaria: experiences from the Kintampo districts of Ghana. Malaria journal. 2016 Feb; 15(?):108. doi: 10.1186/s12936-016-1151-7. [PMID: 26896962]
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  • Kimberly K Scarsi, Fatai A Fehintola, Qing Ma, Francesca T Aweeka, Kristin M Darin, Gene D Morse, Ibrahim Temitope Akinola, Waheed A Adedeji, Niklas Lindegardh, Joel Tarning, Oladosu Ojengbede, Isaac F Adewole, Babafemi Taiwo, Robert L Murphy, Olusegun O Akinyinka, Sunil Parikh. Disposition of amodiaquine and desethylamodiaquine in HIV-infected Nigerian subjects on nevirapine-containing antiretroviral therapy. The Journal of antimicrobial chemotherapy. 2014 May; 69(5):1370-6. doi: 10.1093/jac/dkt513. [PMID: 24446424]
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