5-ヒドロキシインドール酢酸 5-hydroxyindole acetic acid

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2013/02/20 16:39:09」(JST)

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5-Hydroxyindoleacetic acid (5-HIAA) is the main metabolite of serotonin in the human body. In chemical analysis of urine samples, 5-HIAA is used to determine serotonin levels in the body.

Clinical significance

5-HIAA is tested by 24-hour urine samples combined with an acidic additive to maintain pH below 3. Certain foods and drugs are known to interfere with the measurement. 5-HIAA levels can vary depending on other complications, including tumors, renal malfunction, and small bowel resection.

Since 5-HIAA is a metabolite of serotonin, testing is most frequently performed for the diagnosis of carcinoid tumors of the enterochromaffin (Kultschitzsky) cells of the small intestine, which release large amounts of serotonin. Values greater than 25 mg per 24 hours (higher if the patient has malabsorption) are strong evidence for carcinoid.

Low levels of 5-HIAA in the cerebrospinal fluid have been associated with aggressive behavior and suicide by violent means, correlating with diminished serotonin levels.^[1]

Elevated serotonin (hyperserotonemia) is one of the most common biological findings in autism^[2] and 5-HIAA may be elevated in patients with autistic spectrum disorders.

Limitations

5-HIAA may be normal with nonmetastatic carcinoid tumor and may be normal even with the carcinoid syndrome, particularly in subjects without diarrhea, because some patients with the carcinoid syndrome excrete nonhydroxylated indolic acids.

Midgut carcinoids are most apt to produce the carcinoid syndrome with 5-HIAA elevation. Patients with renal disease may have falsely low 5-HIAA levels in the urine.
5-HIAA is increased in untreated patients with malabsorption, who have increased urinary tryptophan metabolites. Such patients include those with celiac disease, tropical sprue, Whipple disease, stasis syndrome, and cystic fibrosis. It is increased in those with chronic intestinal obstruction.
Poor correlation exists between 5-HIAA level and the clinical severity of the carcinoid syndrome. 3 recent studies confirm its use as a prognostic factor in this disease.
5-HIAA is the major urinary metabolite of serotonin, a ubiquitous bioactive amine. Serotonin, and consequently 5-HIAA, are produced in excess by most carcinoid tumors, especially those producing the carcinoid syndrome of flushing, hepatomegaly (enlarged liver), diarrhea, bronchospasm, and heart disease. Quantitation of urinary 5-HIAA is the best test for carcinoid, but scrupulous care must be taken that specimen collection and patient preparation have been correct. Carcinoid tumors may cause increased excretion of tryptophan, 5-hydroxytryptophan and histamine as well as serotonin. Serum serotonin assay may detect some carcinoids missed by 5-HIAA assay.

The production and metabolism of serotonin, and thus 5-HIAA, is dependent upon the tissue of origin of the tumor. Tumors from midgut cells, such as ileal carcinoid usually contain and release large quantities of serotonin. These amounts may not be fully reflected in the amount of 5-HIAA in urine, because little is metabolized. Foregut tumors lack the decarboxylase enzyme necessary to convert 5-hydroxytryptophan to serotonin, resulting in minimal to no elevation in urinary 5-HIAA levels. Tumors derived from hindgut cells (rectal carcinoid) rarely produce excess serotonin or 5-HIAA. Of 75 patients with carcinoid tumors, 75% had above normal urinary 5-HIAA excretion and 64% had above normal serotonin excretion.^{[citation needed]}

References

^ Thomas Bronisch: Der Suizid: Ursachen Warnsignale Prävention. 5. Auflage, C.H.Beck, München 2007, ISBN 978-3-406-55967-9, S. 63–65 (German).
^ Burgess, NK; Sweeten, TL; McMahon, WM; Fujinami, RS (2006). "Hyperserotoninemia and altered immunity in autism.". Journal of autism and developmental disorders 36 (5): 697–704. doi:10.1007/s10803-006-0100-7. PMID 16614791.

UpToDate Contents

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1. カルチノイド症候群および腫瘍局在の診断 diagnosis of the carcinoid syndrome and tumor localization
2. 転移性胃腸膵管系神経内分泌腫瘍：症状、予後、画像検査、および生化学的モニタリング metastatic gastroenteropancreatic neuroendocrine tumors presentation prognosis imaging and biochemical monitoring
3. 小腸腫瘍の診断および病期分類 diagnosis and staging of small bowel neoplasms
4. カルチノイド症候群の臨床的特徴 clinical features of the carcinoid syndrome
5. 気管支神経内分泌（カルチノイド）腫瘍：疫学、危険因子、分類、組織学的検査、診断、および病期分類 bronchial neuroendocrine carcinoid tumors epidemiology risk factors classification histology diagnosis and staging

English Journal

Glucagon-like peptide-2 but not imipramine exhibits antidepressant-like effects in ACTH-treated mice.

Iwai T, Ohnuki T, Sasaki-Hamada S, Saitoh A, Sugiyama A, Oka J.SourceLaboratory of Pharmacology, Faculty of Pharmaceutical Sciences, Tokyo University of Science, 2641 Yamazaki, Noda, Chiba, 278-8510, Japan; Department of Neuropsychopharmacology, National Institute of Mental Health, National Center of Neurology and Psychiatry, Tokyo 187-8553, Japan.
Behavioural brain research.Behav Brain Res.2013 Apr 15;243:153-7. doi: 10.1016/j.bbr.2013.01.010. Epub 2013 Jan 16.
We investigated the effectiveness of glucagon-like peptide-2 (GLP-2) against refractory depression in adrenocorticotropic hormone (ACTH)-treated mice as a model of tricyclic antidepressant (TCA)-resistant depression. Chronic ACTH treatment (0.45mg/kg, s.c., 14 days) weakened the antidepressant-like
PMID 23333402

Hereditary catalepsy in mice is associated with the brain dysmorphology and altered stress response.

Tikhonova MA, Kulikov AV, Bazovkina DV, Kulikova EA, Tsybko AS, Bazhenova EY, Naumenko VS, Akulov AE, Moshkin MP, Popova NK.SourceInstitute of Cytology and Genetics, Siberian Branch of the Russian Academy of Sciences, Novosibirsk, Russia. Electronic address: mar-a-tikh@mail.ru.
Behavioural brain research.Behav Brain Res.2013 Apr 15;243:53-60. doi: 10.1016/j.bbr.2012.12.057. Epub 2013 Jan 4.
Catalepsy is a passive defensive strategy in response to threatening stimuli. In exaggerated forms it is associated with brain dysfunctions. The study was aimed to examine (1) possible association of the hereditary catalepsy with neuroanatomical characteristics and (2) sensitivity of the catalepsy e
PMID 23295395

Japanese Journal

Regional differences in serotonin content in the nucleus of the solitary tract of male rats after hypovolemia produced by polyethylene glycol

Curtis J. Thomas,Anderson Michael B.,Curtis Kathleen S.
The journal of physiological sciences 63(1), 39-46, 2013-01
NAID 40019538826

カルチノイド腫瘍(神経内分泌腫瘍)の診断と治療 (内分泌腺腫瘍--基礎・臨床研究のアップデート) -- (カルチノイド腫瘍(神経内分泌腫瘍))

平田結喜緒
日本臨床 69(-), 648-651, 2011-03
NAID 40018749454

Related Pictures

★リンクテーブル★

リンク元	「セロトニン」「5-ヒドロキシインドール酢酸」「5-hydroxyindole acetic acid」「5-hydroxyindole-acetic acid」「5-hydroxyindoleacetic acid」
拡張検索	「尿中5-HIAA」「5-HIAA試験」
関連記事	「HIAA」「HI」

「セロトニン」

5-Hydroxyindoleacetic acid
	IUPAC name 2-(5-Hydroxy-1H-indol-3-yl)acetic acid
Identifiers
CAS number	54-16-0
PubChem	1826
ChemSpider	1760
KEGG	C05635
MeSH	Hydroxyindoleacetic+Acid
ChEBI	CHEBI:27823
ChEMBL	CHEMBL395915
Jmol-3D images	Image 1
	SMILES c1cc2c(cc1O)c(c[nH]2)CC(=O)O ;
	InChI InChI=1S/C10H9NO3/c12-7-1-2-9-8(4-7)6(5-11-9)3-10(13)14/h1-2,4-5,11-12H,3H2,(H,13,14) ; Key: DUUGKQCEGZLZNO-UHFFFAOYSA-N InChI=1/C10H9NO3/c12-7-1-2-9-8(4-7)6(5-11-9)3-10(13)14/h1-2,4-5,11-12H,3H2,(H,13,14); Key: DUUGKQCEGZLZNO-UHFFFAOYAY ;
Properties
Molecular formula	C10H9NO3
Molar mass	191.18 g mol−1
	(verify) (what is: /?); Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
	Infobox references

　　[★]

英: serotonin, 5-HT, 5-hydroxytryptamine
関: 神経伝達物質、セロトニン受容体、セロトニン作動性ニューロン、5-ヒドロキシインドール酢酸 5-HIAA

トリプトファンから生合成される。
生合成：(1)トリプトファンの5位にヒドロキシ基付加　→　(2)脱炭酸
酵素は、芳香族アミノ酸デカルボキシラーゼ(補酵素はピリドキサル5'-リン酸(PLP))
脳や神経で起こる。

生合成
　トリプトファン　　 　　　　　　 →　　　　　　5-ヒドロキシトリプトファン
　　　　　　　　　トリプトファン5-モノオキシゲナーゼ

　　　　　　　　　　　　　　　　　　　　　　　　　　　　　　　   　　　OH
　　　　　　　　           ／＼　　　   　　　　　　　       　 ／＼／
　-OOC-CH(NH3+)-CH2----|○｜　→　-OOC-CH(NH3+)-CH2----| ○|
　　　　　　　      ||    |  |　　     　　　　　　   ||    |　 ｜
　　 　　　　 　      ＼ ／ ＼／　　　   　　　　　　     ＼ ／ ＼／
　　　 　　 　          NH　　　　　　          　　　　　　NH
　　　　　　　　　　+                              +
　　　　テトラヒドロビオプテリン　　　　　ジヒドロビオプテリン
　　　　　　　　　　+
　　　　　　　　　　O2

　5-ヒドロキシトリプトファン　　 →　　　　　　セロトニン
　　　　　　　　　芳香族アミノ酸デカルボキシラーゼ

　　　　　　　　　　　　　　　　　　　　　　　　　　　　　　　　OH
　　　　　　　　           ／＼　　　   　　　　      　 ／＼／
　-OOC-CH(NH3+)-CH2----|○ |　→　H2N-CH2-CH2----| ○|
　　　　　　　      ||    |  ｜ 　    　　　   ||    |   |
　　 　　　　 　      ＼ ／ ＼／　　　   　　　     ＼ ／＼／
　　　 　　 　          NH　　　　　　        　　　　NH