{{위키데이터 속성 추적}}
{{Infobox drug
| Verifiedfields    =
| Watchedfields     =
| verifiedrevid     = 718190677
| drug_name         = β-하이드록시 β-메틸뷰티르산
| INN               = none
| IUPAC_name        = 3-hydroxy-3-methylbutanoic acid
| image             = Beta-Hydroxy beta-methylbutyric acid 2.svg
| width             =
| alt               = Structural formula, conjugate acid
| image2            = Beta-Hydroxy beta-methylbutyrate 2.svg
| width2            =
| alt2              = Structural formula, conjugate base
| caption           = Top: β-Hydroxy β-methylbutyric acid<br />Bottom: β-Hydroxy β-methylbutyrate
<!-- Clinical data -->
| pronounce         =
| Drugs.com         =
| MedlinePlus       =
| licence_EU        = <!-- EMA requires brand name -->
| licence_US        = <!-- FDA may use generic name -->
| pregnancy_AU      = <!-- A/B1/B2/B3/C/D/X -->
| pregnancy_AU_comment =
| pregnancy_US      = <!-- A / B / C / D / X / N -->
| pregnancy_US_comment =
| pregnancy_category=
| routes_of_administration = [[경구 투여]]<ref name="ISSN position stand 2013" /><!--This ref refers to "ingestion" of HMB a number of times--> 또는 코로 투여<ref name="Ensure and Juven">{{웹 인용|title=Product Information: Ensure Enlive Advanced Therapeutic Nutrition Shake|publisher=Abbott Nutrition|url=http://static.abbottnutrition.com/cms-prod/abbottnutrition.com/img/Ensure-Enlive-Advanced-Therapeutic-Nutrition-Shake.pdf|access-date=22 August 2016|date=9 August 2016|quote=<br />{{•}}Use under medical supervision.<br />{{•}}HMB + protein for muscle health.|url-status=live|archive-url=https://web.archive.org/web/20161012132214/http://static.abbottnutrition.com/cms-prod/abbottnutrition.com/img/Ensure-Enlive-Advanced-Therapeutic-Nutrition-Shake.pdf|archive-date=12 October 2016}}<br /><br />{{웹 인용|title=Product Information: Juven|publisher=Abbott Nutrition|url=http://static.abbottnutrition.com/cms-prod/abbottnutrition.com/img/Juven.pdf|date=7 May 2016|access-date=22 August 2016|quote=<br />{{•}}Administer orally or as a modular via feeding tube&nbsp;...<br />{{•}}Use under medical supervision.<br />{{•}}Nutravigor® (CaHMB, calcium β-hydroxy-β-methylbutyrate)|url-status=live|archive-url=https://web.archive.org/web/20161012132216/http://static.abbottnutrition.com/cms-prod/abbottnutrition.com/img/Juven.pdf|archive-date=12 October 2016}}</ref>
| legal_AU          = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled-->
| legal_AU_comment  =
| legal_CA          = <!-- OTC, Rx-only, Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_CA_comment  =
| legal_DE          = <!-- Anlage I, II, III or Unscheduled-->
| legal_DE_comment  =
| legal_NZ          = <!-- Class A, B, C -->
| legal_NZ_comment  =
| legal_UK          = <!-- GSL, P, POM, CD, CD Lic, CD POM, CD No Reg POM, CD (Benz) POM, CD (Anab) POM or CD Inv POM / Class A, B, C -->
| legal_UK_comment  =
| legal_US          = Dietary supplement
| legal_US_comment  =
| legal_UN          = Unscheduled
| legal_UN_comment  =
| legal_status      = 
<!-- Pharmacokinetic data -->
| bioavailability   =
| protein_bound     =
| metabolism        =
| metabolites       = [[HMB-CoA]], [[HMG-CoA]], [[메발론산]], [[콜레스테롤]], [[아세틸-CoA]], [[아세토아세트산]], [[β-하이드록시뷰티르산]]
| onset             = {{abbr|HMB-FA|β-hydroxy β-methylbutyric acid}}: 30–60&nbsp;minutes<ref name="ISSN position stand 2013"/><br />{{abbr|HMB-Ca|calcium β-hydroxy β-methylbutyrate monohydrate}}: 1–2&nbsp;hours<ref name="ISSN position stand 2013"/>
| elimination_half-life = {{abbr|HMB-FA|β-hydroxy β-methylbutyric acid}}: 3&nbsp;hours<ref name="ISSN position stand 2013"/><br />{{abbr|HMB-Ca|calcium β-hydroxy β-methylbutyrate monohydrate}}: 2.5&nbsp;hours<ref name="ISSN position stand 2013"/>
| duration_of_action =
| excretion         = [[콩팥]] (10–40% 배설)<ref name="ISSN position stand 2013">{{저널 인용| vauthors = Wilson JM, Fitschen PJ, Campbell B, Wilson GJ, Zanchi N, Taylor L, Wilborn C, Kalman DS, Stout JR, Hoffman JR, Ziegenfuss TN, Lopez HL, Kreider RB, Smith-Ryan AE, Antonio J | title = International Society of Sports Nutrition Position Stand: beta-hydroxy-beta-methylbutyrate (HMB) | journal = Journal of the International Society of Sports Nutrition | volume = 10 | issue = 1 | pages = 6 | date = February 2013 | pmid = 23374455 | pmc = 3568064 | doi = 10.1186/1550-2783-10-6 | quote = The [International Society of Sports Nutrition] has concluded the following.  1. HMB can be used to enhance recovery by attenuating exercise induced skeletal muscle damage in trained and untrained populations.&nbsp;... 4. Thirty-eight mg·kg·BM<sup>−1</sup> daily of HMB has been demonstrated to enhance skeletal muscle hypertrophy, strength, and power in untrained and trained populations when the appropriate exercise prescription is utilized.&nbsp;... 8. HMB's mechanisms of action include an inhibition and increase of proteolysis and protein synthesis, respectively. 9. Chronic consumption of HMB is safe in both young and old populations. }}</ref><ref name="HMB athletic performance-related effects 2011 review">{{저널 인용| vauthors = Zanchi NE, Gerlinger-Romero F, Guimarães-Ferreira L, de Siqueira Filho MA, Felitti V, Lira FS, Seelaender M, Lancha AH | title = HMB supplementation: clinical and athletic performance-related effects and mechanisms of action | journal = Amino Acids | volume = 40 | issue = 4 | pages = 1015–1025 | date = April 2011 | pmid = 20607321 | doi = 10.1007/s00726-010-0678-0 | s2cid = 11120110 | url = https://repositorio.unal.edu.co/handle/unal/77957 | quote = HMB is a metabolite of the amino acid leucine (Van Koverin and Nissen 1992), an essential amino acid. The first step in HMB metabolism is the reversible transamination of leucine to [α-KIC] that occurs mainly extrahepatically (Block and Buse 1990). Following this enzymatic reaction, [α-KIC] may follow one of two pathways. In the first, HMB is produced from [α-KIC] by the cytosolic enzyme KIC dioxygenase (Sabourin and Bieber 1983). The cytosolic dioxygenase has been characterized extensively and differs from the mitochondrial form in that the dioxygenase enzyme is a cytosolic enzyme, whereas the dehydrogenase enzyme is found exclusively in the mitochondrion (Sabourin and Bieber 1981, 1983). Importantly, this route of HMB formation is direct and completely dependent of liver KIC dioxygenase. Following this pathway, HMB in the cytosol is first converted to cytosolic β-hydroxy-β-methylglutaryl-CoA (HMG-CoA), which can then be directed for cholesterol synthesis (Rudney 1957) (Fig. 1). In fact, numerous biochemical studies have shown that HMB is a precursor of cholesterol (Zabin and Bloch 1951; Nissen et al. 2000).<!--<br /><br /> In the second pathway, after transamination, [α-KIC] in liver generates isovaleryl-CoA through the enzymatic action of branched-chain ketoacid dehydrogenase (BCKD) and after several steps, there is production of HMG-CoA through the enzyme HMG-CoA synthase (Fig. 1). Under normal conditions the majority of KIC is converted into isovaleryl-CoA, in which approximately 5% of leucine is metabolized into HMB (Wilson et al. 2008; Van Koverin and Nissen 1992). However, Nissen and Abumrad (1997) provided evidence that the primary fate of HMB is probably conversion to HMG-CoA in the liver, for cholesterol biosynthesis.--> }}</ref>
<!-- Identifiers -->
| CAS_number        = 625-08-1
| CAS_supplemental  =
| CAS_number_Ref    = {{cascite|correct|}}
| ATC_prefix        = none
| PubChem           = 69362
| IUPHAR_ligand     =
| DrugBank          =
| DrugBank_Ref      =
| ChemSpiderID      = 62571
| ChemSpiderID_Ref  = {{chemspidercite|correct|chemspider}}
| UNII              = 3F752311CD
| UNII_Ref          = {{fdacite|correct|FDA}}
| KEGG              = C20827
| KEGG_Ref          = {{keggcite|correct|kegg}}
| ChEBI             = 37084
| ChEBI_Ref         = {{ebicite|correct|}}
| ChEMBL            =
| NIAID_ChemDB      =
| synonyms          = [[짝산]] 형태:<br />β-하이드록시아이소발레르산<br />3-하이드록시아이소발레르산<br />[[짝염기]] 형태:<br />하이드록시메틸뷰티르산
<!-- Chemical data -->
| C=5 | H=10 | O=3
| SMILES            = CC(C)(CC(=O)O)O
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C5H10O3/c1-5(2,8)3-4(6)7/h8H,3H2,1-2H3,(H,6,7)
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = AXFYFNCPONWUHW-UHFFFAOYSA-N
| density           = ~1.1
| density_notes     = at 20&nbsp;°C<ref name="HMB MSDS">{{웹 인용|title=Safety data sheet: 3-Hydroxy-3-methyl butyric acid|url=http://www.alfachina.cn/AlfaAesarApp/getpdf?contentId=EN_US_MSDS_42722|publisher=Alfa Aesar|access-date=9 November 2016|date=23 March 2005|url-status=live|archive-url=https://web.archive.org/web/20160917215449/http://www.alfachina.cn/AlfaAesarApp/getpdf?contentId=EN_US_MSDS_42722|archive-date=17 September 2016}}</ref>
| solubility        =
| melting_point     = −80
| melting_high      =
| melting_notes     = (glass)<ref name = "Coffman_1958">{{저널 인용| vauthors = Coffman DD, Cramer R, Mochel WE | title = Syntheses by Free-radical Reactions. V. A New Synthesis of Carboxylic Acids | journal = Journal of the American Chemical Society | date = June 1958 | volume = 80 | issue = 11 | pages = 2882–2887 | doi = 10.1021/ja01544a072 }}</ref>
| boiling_point     = 128
| boiling_notes     = at 7&nbsp;[[수은주 밀리미터|mmHg]]<ref name="HMB MSDS">{{웹 인용|title=Safety data sheet: 3-Hydroxy-3-methyl butyric acid|url=http://www.alfachina.cn/AlfaAesarApp/getpdf?contentId=EN_US_MSDS_42722|publisher=Alfa Aesar|access-date=9 November 2016|date=23 March 2005|url-status=live|archive-url=https://web.archive.org/web/20160917215449/http://www.alfachina.cn/AlfaAesarApp/getpdf?contentId=EN_US_MSDS_42722|archive-date=17 September 2016}}</ref><ref name="ChemSpider">{{백과사전 인용| title=3-OH-isovaleric acid | url=http://www.chemspider.com/Chemical-Structure.62571.html | work=ChemSpider | date=2015 | publisher=Royal Society of Chemistry | access-date=10 August 2016 | quote=Experimental Boiling Point:&nbsp;... 128&nbsp;°C / 7&nbsp;mm&nbsp;...<br />Experimental solubility:<br />Soluble in water | url-status=live | archive-url=https://web.archive.org/web/20160811095753/http://www.chemspider.com/Chemical-Structure.62571.html | archive-date=11 August 2016 }}</ref>
}}

'''β-하이드록시 β-메틸뷰티르산'''({{llang|en|β-hydroxy β-methylbutyric acid}}, '''HMB''')은 인체에서 [[천연물|자연적으로 생성되는 물질]]로, [[식이 보충제]]로 사용되며 [[상처 치유]]를 촉진하고 [[암]]이나 [[HIV]]/[[AIDS]]로 인한 [[근위축증|근육 소모]]가 있는 사람들에게 영양 지원을 제공하기 위한 특정 [[의료 식품]]의 성분으로 사용된다.<ref name="ISSN position stand 2013">{{저널 인용| vauthors = Wilson JM, Fitschen PJ, Campbell B, Wilson GJ, Zanchi N, Taylor L, Wilborn C, Kalman DS, Stout JR, Hoffman JR, Ziegenfuss TN, Lopez HL, Kreider RB, Smith-Ryan AE, Antonio J | title = International Society of Sports Nutrition Position Stand: beta-hydroxy-beta-methylbutyrate (HMB) | journal = Journal of the International Society of Sports Nutrition | volume = 10 | issue = 1 | pages = 6 | date = February 2013 | pmid = 23374455 | pmc = 3568064 | doi = 10.1186/1550-2783-10-6 | quote = The [International Society of Sports Nutrition] has concluded the following.  1. HMB can be used to enhance recovery by attenuating exercise induced skeletal muscle damage in trained and untrained populations.&nbsp;... 4. Thirty-eight mg·kg·BM<sup>−1</sup> daily of HMB has been demonstrated to enhance skeletal muscle hypertrophy, strength, and power in untrained and trained populations when the appropriate exercise prescription is utilized.&nbsp;... 8. HMB's mechanisms of action include an inhibition and increase of proteolysis and protein synthesis, respectively. 9. Chronic consumption of HMB is safe in both young and old populations. }}</ref><ref name="Iowa State University">{{웹 인용|vauthors=Linn J|title=Proteins in Human Health and Performance|url=http://www.fshn.hs.iastate.edu/proteins-in-human-health-and-performance/|archive-url=https://web.archive.org/web/20160827191643/http://www.fshn.hs.iastate.edu/proteins-in-human-health-and-performance/|archive-date=27 August 2016|publisher=Iowa State University|access-date=31 July 2016|date=13 May 2013|quote=Dr. Nissen and his collaborator Dr. Naji N. Abumrad, Professor and Chair, Department of Surgery, Vanderbilt University, discovered beta-hydroxy-beta-methylbutyrate (HMB) and its beneficial effects on human health and performance. HMB is currently marketed nationally by Abbott Laboratories as Revigor™, which is a component of Ensure® Muscle Health, and Juven®, which is a nutritional beverage that is clinically shown to promote healing after injury or surgery.|url-status=dead}}</ref><ref name="Medical foods">{{저널 인용| vauthors = Khamsi R | title = Rethinking the formula | journal = Nature Medicine | volume = 19 | issue = 5 | pages = 525–529 | date = May 2013 | pmid = 23652097 | doi = 10.1038/nm0513-525 | s2cid = 205379191 | quote = The questions about what defines a medical food will likely grow as the market does—and that market now extends far beyond PKU and other inherited metabolic disorders.&nbsp;... Abbott Nutrition's Juven provides nutrients to people with HIV or AIDS experiencing excessive weight loss due to disease | doi-access = free }}</ref><ref name="PR Newswire">{{웹 인용|title=JUVEN Added to Abbott Laboratories' Nutritional Product Line for People With Cancer, HIV/AIDS and Wounds/Pressure Ulcers|url=http://www.prnewswire.com/news-releases/juven-added-to-abbott-laboratories-nutritional-product-line-for-people-with-cancer-hivaids-and-woundspressure-ulcers-72059102.html|website=PR Newswire|publisher=Abbott Laboratories|access-date=11 December 2016|date=12 March 2004|url-status=dead|archive-url=https://web.archive.org/web/20161220105220/http://www.prnewswire.com/news-releases/juven-added-to-abbott-laboratories-nutritional-product-line-for-people-with-cancer-hivaids-and-woundspressure-ulcers-72059102.html|archive-date=20 December 2016}}</ref> 건강한 성인의 경우 HMB를 보충하면 [[근육]] 크기, 근력 및 제지방량이 증가하고 운동으로 인한 [[골격근]] 손상이 감소하며 유산소 운동 능력이 향상되고 운동 회복이 빨라지는 것으로 나타났다.

== 같이 보기 ==
* [[β-하이드록시 β-메틸뷰티릴-CoA]]

== 각주 ==
{{각주}}

{{아미노산 대사 중간생성물들}}
{{스테로이드 대사 중간생성물들}}
{{식사 보충물}}

[[분류:아미노산 유도체]]
[[분류:생체분자]]
[[분류:식이 보충제]]
[[분류:사람의 대사산물]]
[[분류:베타-하이드록시산]]
[[분류:생리학]]
[[분류:재활의학]]
[[분류:의료식품]]
[[분류:근육 질환]]
[[분류:경기력 향상 약물]]