Vanillylmandelic acid (BioDeep_00000265254)
Main id: BioDeep_00000003208
PANOMIX_OTCML-2023
代谢物信息卡片
dl-4-hydroxy-3-methoxymandelic acid
化学式: C9H10O5 (198.052821)
中文名称: DL-4-羟基-3-甲氧基苯乙醇酸, 3-甲氧基-4-羟基扁桃酸
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: COC1=C(C=CC(=C1)C(C(=O)O)O)O
InChI: InChI=1S/C9H10O5/c1-14-7-4-5(2-3-6(7)10)8(11)9(12)13/h2-4,8,10-11H,1H3,(H,12,13)
描述信息
D000890 - Anti-Infective Agents > D000892 - Anti-Infective Agents, Urinary > D008333 - Mandelic Acids
An aromatic ether that is the 3-O-methyl ether of 3,4-dihydroxymandelic acid.
Vanillylmandelic acid is the endproduct of epinephrine and norepinephrine metabolism. Vanillylmandelic acid can be used as an indication of the disorder in neurotransmitter metabolism as well. Vanillylmandelic acid has antioxidant activity towards DPPH radical with an IC50 value of 33 μM[1].
同义名列表
数据库引用编号
19 个数据库交叉引用编号
- ChEBI: CHEBI:20106
- KEGG: C05584
- KEGGdrug: D90829
- PubChem: 1245
- ChEMBL: CHEMBL1256396
- MeSH: Vanilmandelic Acid
- KNApSAcK: C00052427
- CAS: 53587-34-1
- CAS: 2394-20-9
- CAS: 55-10-7
- MoNA: HMDB0000291_ms_ms_493
- MoNA: HMDB0000291_ms_ms_492
- MoNA: HMDB0000291_ms_ms_494
- MetaboLights: MTBLC20106
- PubChem: 7910
- 3DMET: B05077
- NIKKAJI: J27.583B
- RefMet: Vanillylmandelic acid
- medchemexpress: HY-113121
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
- 9606 Homo sapiens: 10.1007/S11306-016-1051-4
- 28511 Pogostemon cablin: 10.1021/JF304466T
- 9606 Homo sapiens: 10.1007/S11306-016-1051-4
- 28511 Pogostemon cablin: 10.1021/JF304466T
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
- Jinmin Li, Xiangyang Liu, Mo Chen, Jiachen Wang, Xinning Wang. Values of serum CA125, NSE and 24-hour urine VMA in diagnosis and prediction of treatment of paediatric neuroblastoma.
International journal of clinical practice.
2021 Dec; 75(12):e14932. doi:
10.1111/ijcp.14932. [PMID: 34606672] - Narae Hwang, Eunbin Chong, Hyeonju Oh, Hee Won Cho, Ji Won Lee, Ki Woong Sung, Soo-Youn Lee. Application of an LC-MS/MS Method for the Simultaneous Quantification of Homovanillic Acid and Vanillylmandelic Acid for the Diagnosis and Follow-Up of Neuroblastoma in 357 Patients.
Molecules (Basel, Switzerland).
2021 Jun; 26(11):. doi:
10.3390/molecules26113470. [PMID: 34200415] - 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] - E A Soler Arias, R H Trigo, D D Miceli, P N Vidal, M F Hernandez Blanco, V A Castillo. Urinary vanillylmandelic acid:creatinine ratio in dogs with pheochromocytoma.
Domestic animal endocrinology.
2021 01; 74(?):106559. doi:
10.1016/j.domaniend.2020.106559. [PMID: 32980593] - Valeriy D Zaytsev, Aleksei A Furletov, Vladimir V Apyari, Alexey V Garshev, Stanislava G Dmitrienko, Yury A Zolotov. Label-free silver triangular nanoplates for spectrophotometric determination of catecholamines and their metabolites.
Mikrochimica acta.
2020 10; 187(11):610. doi:
10.1007/s00604-020-04576-1. [PMID: 33057848] - Meng Wei, Mujie Ye, Kuiran Dong, Rui Dong. Mass screening for neuroblastoma in infants.
Discovery medicine.
2020 Sep; 30(160):63-70. doi:
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Molecular genetics and metabolism.
2020 Sep; 131(1-2):163-170. doi:
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The journal of applied laboratory medicine.
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Pakistan journal of pharmaceutical sciences.
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2018 Sep; 53(9):1761-1765. doi:
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Clinical chemistry and laboratory medicine.
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The Indian journal of medical research.
2018 04; 147(4):384-390. doi:
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Bone.
2017 Dec; 105(?):1-10. doi:
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Biomarkers : biochemical indicators of exposure, response, and susceptibility to chemicals.
2017 Dec; 22(8):790-797. doi:
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Environmental health : a global access science source.
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Pediatric neurology.
2017 Oct; 75(?):66-72. doi:
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Pediatrics.
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JAMA.
2017 Jul; 318(4):385-386. doi:
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Journal of cancer research and clinical oncology.
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Experimental gerontology.
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BMC endocrine disorders.
2017 Feb; 17(1):9. doi:
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Brain & development.
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Brain & development.
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Clinical chemistry.
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2016 Jun; 34(6):461-5. doi:
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FASEB journal : official publication of the Federation of American Societies for Experimental Biology.
2016 Feb; 30(2):994-1001. doi:
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American journal of hypertension.
2016 Jan; 29(1):63-72. doi:
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Journal of the renin-angiotensin-aldosterone system : JRAAS.
2015 Dec; 16(4):801-12. doi:
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Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2015 Oct; 1002(?):92-7. doi:
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International journal of hygiene and environmental health.
2015 Jul; 218(5):452-60. doi:
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Brain & development.
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Journal of ethnopharmacology.
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The Journal of pediatrics.
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2014 Jul; 29(7):952-4. doi:
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Clinical biochemistry.
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Amino acids.
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Clinical biochemistry.
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Endocrine journal.
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No to hattatsu = Brain and development.
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Pediatric blood & cancer.
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Clinica chimica acta; international journal of clinical chemistry.
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Medicina clinica.
2013 May; 140(10):453-7. doi:
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Cancer imaging : the official publication of the International Cancer Imaging Society.
2013 Apr; 13(?):155-61. doi:
10.1102/1470-7330.2013.0017. [PMID: 23598367] - J Li, C-H Yang, L-M Li. Diagnosis and treatment of 29 cases of adrenal ganglioneuroma.
European review for medical and pharmacological sciences.
2013 Apr; 17(8):1110-3. doi:
NULL. [PMID: 23661526] - Hajime Mizukami, Shuichi Hara, Masamune Kobayashi, Shinjiro Mori, Fumi Kuriiwa, Tatsushige Fukunaga. An autopsy case of bilateral adrenal pheochromocytoma-associated cerebral hemorrhage.
Legal medicine (Tokyo, Japan).
2013 Mar; 15(2):91-5. doi:
10.1016/j.legalmed.2012.08.007. [PMID: 22981089] - Marcello Monteleone, Attilio Naccarato, Giovanni Sindona, Antonio Tagarelli. A reliable and simple method for the assay of neuroendocrine tumor markers in human urine by solid-phase microextraction-gas chromatography-triple quadrupole mass spectrometry.
Analytica chimica acta.
2013 Jan; 759(?):66-73. doi:
10.1016/j.aca.2012.11.017. [PMID: 23260678] - Meng-Yao Lu, Yen-Lin Liu, Hsiu-Hao Chang, Shiann-Tarng Jou, Yung-Li Yang, Kai-Hsin Lin, Dong-Tsamn Lin, Ya-Ling Lee, Hsinyu Lee, Pei-Yi Wu, Tsai-Yueh Luo, Lie-Hang Shen, Shiu-Feng Huang, Yung-Feng Liao, Wen-Ming Hsu, Kai-Yuan Tzen. Characterization of neuroblastic tumors using 18F-FDOPA PET.
Journal of nuclear medicine : official publication, Society of Nuclear Medicine.
2013 Jan; 54(1):42-9. doi:
10.2967/jnumed.112.102772. [PMID: 23213196] - Prabal Deb, Seerat Pal, Vibha Dutta, Anand Srivastava, Akshay Bhargava, Krishan Kumar Yadav. Adrenal haemangioblastoma presenting as phaeochromocytoma: a rare manifestation of extraneural hemangioblastoma.
Endocrine pathology.
2012 Sep; 23(3):187-90. doi:
10.1007/s12022-012-9207-x. [PMID: 22544391] - Wayne L Furman, Lisa M McGregor, M Beth McCarville, Mihaela Onciu, Andrew M Davidoff, Sandy Kovach, Dana Hawkins, Valerie McPherson, Peter J Houghton, Catherine A Billups, Jianrong Wu, Clinton F Stewart, Victor M Santana. A single-arm pilot phase II study of gefitinib and irinotecan in children with newly diagnosed high-risk neuroblastoma.
Investigational new drugs.
2012 Aug; 30(4):1660-70. doi:
10.1007/s10637-011-9724-3. [PMID: 21796439] - Sarah Garnier, Olivier Maillet, Stéphanie Haouy, Magalie Saguintaah, Isabelle Serre, René-Benoit Galifer, Dominique Forgues, Marie-Pierre Guibal, Hossein Allal, Edith Sabatier, Nicolas Kalfa. Prenatal intrarenal neuroblastoma mimicking a mesoblastic nephroma: a case report.
Journal of pediatric surgery.
2012 Aug; 47(8):e21-3. doi:
10.1016/j.jpedsurg.2012.03.090. [PMID: 22901938] - Prabir Kumar Jash, Collin Roy, Kabita Chatterjee. Melanotic neuro-ectodermal tumour of infancy.
Journal of the Indian Medical Association.
2012 Aug; 110(8):578, 583. doi:
NULL. [PMID: 23741827] - P Maskey, G K Shrestha, B R Luitel, D K Gupta, Sidarth, P R Chalise, U K Sharma, P R Gyawali, B R Joshi. Phaeochromocytoma in Nepal--a single centre experience.
Kathmandu University medical journal (KUMJ).
2012 Jul; 10(39):52-5. doi:
10.3126/kumj.v10i3.8020. [PMID: 23434963] - Carlo Scapolla, Giuliana Cangemi, Sebastiano Barco, Laura Barbagallo, Daniela Bugnone, Angelo Maffia, Giovanni Melioli, Aldo Profumo, Umberto Benatti, Gianluca Damonte. Identification and structural characterization by LC-ESI-IONTRAP and LC-ESI-TOF of some metabolic conjugation products of homovanillic acid in urine of neuroblastoma patients.
Journal of mass spectrometry : JMS.
2012 Jul; 47(7):816-24. doi:
10.1002/jms.3016. [PMID: 22791248] - Sujatha Udupa, M Usha, R N Visweswara, M G Desai. Left-sided giant adrenal myelolipoma secreting catecholamine.
Indian journal of pathology & microbiology.
2012 Jul; 55(3):389-91. doi:
10.4103/0377-4929.101755. [PMID: 23032842] - Deepraj Bhandarkar, Avinash Katara, Gaurav Mittal, Phulrenu Chauhan, Manoj Chadha. Laparoscopic management of renal hilar pheochromocytomas.
Surgical laparoscopy, endoscopy & percutaneous techniques.
2012 Jun; 22(3):e148-51. doi:
10.1097/sle.0b013e318248be1c. [PMID: 22678338] - Yong Yang, Zhi-tao Wei, Jin-shan Lu, Qiang Zu, Haiyi Wang, Xu Zhang. Transurethral partial cystectomy with 2 μm thulium continuous wave laser in the treatment of bladder pheochromocytoma.
Journal of endourology.
2012 Jun; 26(6):686-90. doi:
10.1089/end.2011.0005. [PMID: 22007839] - Jin Wook Yi, Eun Mee Oh, Kyu Eun Lee, June Young Choi, Do Hoon Koo, Kyung Joo Kim, Kyeong-Cheon Jung, Seong-Yeon Kim, Yeo-Kyu Youn. An exclusively dopamine secreting paraganglioma in the retroperitoneum: a first clinical case in Korea.
Journal of the Korean Surgical Society.
2012 Jun; 82(6):389-93. doi:
10.4174/jkss.2012.82.6.389. [PMID: 22708103] - Eishin Ogawa, Hiroko Kodama. Effects of disulfiram treatment in patients with Menkes disease and occipital horn syndrome.
Journal of trace elements in medicine and biology : organ of the Society for Minerals and Trace Elements (GMS).
2012 Jun; 26(2-3):102-4. doi:
10.1016/j.jtemb.2012.04.017. [PMID: 22575542] - Lanyun Fang, Yan Lv, Xuefei Sheng, Shanshan Yao. Sensitive, rapid and easy analysis of three catecholamine metabolites in human urine and serum by liquid chromatography tandem mass spectrometry.
Journal of chromatographic science.
2012 May; 50(5):450-6. doi:
10.1093/chromsci/bms068. [PMID: 22511488] - Sunil Kumar Kota, Siva Krishna Kota, Sandip Panda, Kirtikumar D Modi. Pheochromocytoma: an uncommon presentation of an asymptomatic and biochemically silent adrenal incidentaloma.
The Malaysian journal of medical sciences : MJMS.
2012 Apr; 19(2):86-91. doi:
. [PMID: 22973143] - Kai Li, Kuiran Dong, Jiechun Gao, Wei Yao, Xianmin Xiao, Shan Zheng. Neuroblastoma management in Chinese children.
Journal of investigative surgery : the official journal of the Academy of Surgical Research.
2012 Apr; 25(2):86-92. doi:
10.3109/08941939.2011.605203. [PMID: 22439835] - V P Singh, Manjeet Singh, Mridul Malhotra, Ashok Kumar, A K Agarwal. Extra-adrenal phaeochromocytoma-a case report of refractory hypertension.
Indian heart journal.
2012 Mar; 64(2):203-5. doi:
10.1016/s0019-4832(12)60063-7. [PMID: 22572502] - Han-Chih Hencher Lee, Chi-Kong Lai, Kin-Cheong Eric Yau, Tak-Shing Siu, Chloe Miu Mak, Yuet-Ping Yuen, Kwok-Yin Chan, Sidney Tam, Ching-Wan Lam, Albert Yan-Wo Chan. Non-invasive urinary screening for aromatic L-amino acid decarboxylase deficiency in high-prevalence areas: a pilot study.
Clinica chimica acta; international journal of clinical chemistry.
2012 Jan; 413(1-2):126-30. doi:
10.1016/j.cca.2011.09.008. [PMID: 21963339] - Ming-Mu Hsieh, En-Ping Lin, Shiou-Wen Huang. On-line concentration and separation of cationic and anionic neurochemicals by capillary electrophoresis with UV absorption detection.
Talanta.
2012 Jan; 88(?):638-45. doi:
10.1016/j.talanta.2011.11.050. [PMID: 22265552] - B Padilla-Fernández, P Antúnez-Plaza, M F Lorenzo-Gómez, M Rodríguez-González, A Martín-Rodríguez, J M Silva-Abuín. Paraganglioma of prostatic origin.
Clinical medicine insights. Case reports.
2012; 5(?):69-75. doi:
10.4137/ccrep.s9742. [PMID: 22661903] - R Krishnappa, S B Chikaraddi, H N Arun, V Deshmane. Pheochromocytoma in Indian patients: a retrospective study.
Indian journal of cancer.
2012 Jan; 49(1):188-93. doi:
10.4103/0019-509x.98951. [PMID: 22842187] - A Le, L Shang, T Xiao, R Zhuo, Z Wang. Pheochromocytoma in ectopic pregnancy: a case report.
Clinical and experimental obstetrics & gynecology.
2012; 39(4):553-5. doi:
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Zhurnal nevrologii i psikhiatrii imeni S.S. Korsakova.
2012; 112(2 Pt 2):34-40. doi:
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International journal of molecular sciences.
2012; 13(1):1126-53. doi:
10.3390/ijms13011126. [PMID: 22312308] - Balasaheb Siraskar, Jakob Völkl, Mohamed Siyabeldin E Ahmed, Michael Hierlmeier, Shuchen Gu, Evi Schmid, Christina Leibrock, Michael Föller, Undine E Lang, Florian Lang. Enhanced catecholamine release in mice expressing PKB/SGK-resistant GSK3.
Pflugers Archiv : European journal of physiology.
2011 Dec; 462(6):811-9. doi:
10.1007/s00424-011-1006-6. [PMID: 21922189] - Helle-Brit Fiebrich, Johan R de Jong, Ido P Kema, Klaas Pieter Koopmans, Wim Sluiter, Rudi A J O Dierckx, Annemiek M Walenkamp, Thera P Links, Adrienne H Brouwers, Elisabeth G E de Vries. Total 18F-dopa PET tumour uptake reflects metabolic endocrine tumour activity in patients with a carcinoid tumour.
European journal of nuclear medicine and molecular imaging.
2011 Oct; 38(10):1854-61. doi:
10.1007/s00259-011-1862-5. [PMID: 21698413] - Altaf H Shera, Aejaz A Baba, Iftikhar H Bakshi, Iqbal A Lone. Recurrent malignant juxtaglomerular cell tumor: A rare cause of malignant hypertension in a child.
Journal of Indian Association of Pediatric Surgeons.
2011 Oct; 16(4):152-4. doi:
10.4103/0971-9261.86876. [PMID: 22121315] - Ranjit Chaudhary, Abhijeet Deshmukh, Kulwant Singh, Rakesh Biswas. Laparoscopic resection of a large (11 cm) adrenal phaeochromocytoma.
BMJ case reports.
2011 Sep; 2011(?):. doi:
10.1136/bcr.08.2011.4575. [PMID: 22679235] - Takayuki Sumiyoshi, Yosuke Shimizu, Takahiro Inoue, Kazutoshi Okubo, Jun Watanabe, Tomomi Kamba, Koji Yoshimura, Akihiro Kanematsu, Eijiro Nakamura, Hiroyuki Nishiyama, Toshiyuki Kamoto, Shinji Sumiyoshi, Osamu Ogawa. [A case of renal cell carcinoma associated with paraganglioma].
Hinyokika kiyo. Acta urologica Japonica.
2011 Aug; 57(8):429-33. doi:
NULL. [PMID: 21894079] - Runhua Hou, Ann M Leathersich, Brenda Temke Ruud. Pheochromocytoma presenting with arterial and intracardiac thrombus in a 47-year-old woman: a case report.
Journal of medical case reports.
2011 Jul; 5(?):310. doi:
10.1186/1752-1947-5-310. [PMID: 21752274] - Laura Zinnamosca, Luigi Petramala, Dario Cotesta, Cristiano Marinelli, Mauro Schina, Rosario Cianci, Sandra Giustini, Susanna Sciomer, Emanuela Anastasi, Stefano Calvieri, Giorgio De Toma, Claudio Letizia. Neurofibromatosis type 1 (NF1) and pheochromocytoma: prevalence, clinical and cardiovascular aspects.
Archives of dermatological research.
2011 Jul; 303(5):317-25. doi:
10.1007/s00403-010-1090-z. [PMID: 21042801] - D Fraser Davidson, Philip J Hammond, Dermot Murphy, Robert Carachi. Age-related medical decision limits for urinary free (unconjugated) metadrenalines, catecholamines and metabolites in random urine specimens from children.
Annals of clinical biochemistry.
2011 Jul; 48(Pt 4):358-66. doi:
10.1258/acb.2011.011023. [PMID: 21670092] - Sushruta Koppula, Dong Kug Choi. Cuminum cyminum extract attenuates scopolamine-induced memory loss and stress-induced urinary biochemical changes in rats: a noninvasive biochemical approach.
Pharmaceutical biology.
2011 Jul; 49(7):702-8. doi:
10.3109/13880209.2010.541923. [PMID: 21639683] - Kazufumi Yoshihara, Tetsuya Hiramoto, Nobuyuki Sudo, Chiharu Kubo. Profile of mood states and stress-related biochemical indices in long-term yoga practitioners.
BioPsychoSocial medicine.
2011 Jun; 5(1):6. doi:
10.1186/1751-0759-5-6. [PMID: 21635790] - Jae-Hyeong Park, Kyu Seop Kim, Ji-Young Sul, Sung Kyun Shin, Jun Hyung Kim, Jae-Hwan Lee, Si Wan Choi, Jin-Ok Jeong, In-Whan Seong. Prevalence and patterns of left ventricular dysfunction in patients with pheochromocytoma.
Journal of cardiovascular ultrasound.
2011 Jun; 19(2):76-82. doi:
10.4250/jcu.2011.19.2.76. [PMID: 21860721] - Giovanni Maria Poggi, Giuliana Fognani, Daniela Cuzzubbo, Antonio Liguori, Massimo Resti, Ivana Pela. Neuroblastoma presenting with acute kidney injury, hyponatremic-hypertensive-like syndrome and nephrotic proteinuria in a 10-month-old child.
Case reports in oncology.
2011 May; 4(2):400-5. doi:
10.1159/000331211. [PMID: 21941489] - Alireza Hosseinnezhad, Robert M Black, Narothama Reddy Aeddula, Deep Adhikari, Nitin Trivedi. Glucagon-induced pheochromocytoma crisis.
Endocrine practice : official journal of the American College of Endocrinology and the American Association of Clinical Endocrinologists.
2011 May; 17(3):e51-4. doi:
10.4158/ep10388.cr. [PMID: 21324811] - Laura Zinnamosca, Luigi Petramala, Dario Cotesta, Maria Luisa Lefons, Cristiano Marinelli, Piero Chirletti, Cesare Greco, Claudio Letizia. [Adrenal pheochromocytoma associated with 'tako-tsubo' syndrome].
Recenti progressi in medicina.
2011 May; 102(5):202-6. doi:
10.1701/659.7669. [PMID: 21607004] - Inmaculada Navarro, Mercedes Molina, Miguel Civera, Juan F Ascaso, José T Real, Rafael Carmena. [Catecholamine-induced cardiomyopathy triggered by pheochromocytoma].
Endocrinologia y nutricion : organo de la Sociedad Espanola de Endocrinologia y Nutricion.
2011 Apr; 58(4):204-6. doi:
10.1016/j.endonu.2010.11.005. [PMID: 21393076]