Misplaced Pages

:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Galactosamine: Difference between pages - Misplaced Pages

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
(Difference between pages)
Page 1
Page 2
Content deleted Content addedVisualWikitext
Revision as of 14:49, 17 November 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 456609432 of page Galactosamine for the Chem/Drugbox validation project (updated: 'ChEMBL', 'CASNo').  Latest revision as of 04:42, 22 February 2023 edit GünniX (talk | contribs)Extended confirmed users311,108 editsm brackets fixed 
Line 1: Line 1:
{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
{{chembox {{chembox
| Verifiedfields = changed | Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 400097576 | verifiedrevid = 461116190
| reference = <ref>''Merck Index'', 11th Edition, '''4240'''.</ref> | Reference = <ref>''Merck Index'', 11th Edition, '''4240'''.</ref>
| ImageFile = galactosamine.png | ImageFile = galactosamine.png
| ImageFile1 = alpha-D-galactosamine.png | ImageFile1 = D-(+)-Galactosamine Structural Formulae V.1.svg
| ImageSize = 150px | ImageSize =
| ImageSize1 = 150px | ImageSize1 =
| IUPACName = 2-Amino-2-deoxy-D-galactose | IUPACName = 2-Amino-2-deoxy-D-galactose
| OtherNames = α-D-galactosamine | OtherNames = α-D-galactosamine
| Section1 = {{Chembox Identifiers |Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 22576 | ChemSpiderID = 22576
| ChEMBL_Ref = {{ebicite|changed|EBI}} | ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = <!-- blanked - oldvalue: 207280 --> | ChEMBL = 207280
| InChI = 1/C6H13NO5/c7-3-5(10)4(9)2(1-8)12-6(3)11/h2-6,8-11H,1,7H2/t2-,3-,4+,5-,6?/m1/s1 | InChI = 1/C6H13NO5/c7-3-5(10)4(9)2(1-8)12-6(3)11/h2-6,8-11H,1,7H2/t2-,3-,4+,5-,6?/m1/s1
| InChIKey = MSWZFWKMSRAUBD-GASJEMHNBA | InChIKey = MSWZFWKMSRAUBD-GASJEMHNBA
Line 21: Line 21:
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = MSWZFWKMSRAUBD-GASJEMHNSA-N | StdInChIKey = MSWZFWKMSRAUBD-GASJEMHNSA-N
| CASNo_Ref = {{cascite|correct|??}} | CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = <!-- blanked - oldvalue: 7535-00-4 --> | CASNo = 7535-00-4
| UNII_Ref = {{fdacite|correct|FDA}}
⚫ | PubChem = 24154
| UNII = 4Y6R29688W
⚫ | ChEBI_Ref = {{ebicite|changed|EBI}}
⚫ | PubChem = 24154
⚫ | ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 60312 | ChEBI = 60312
| SMILES = O1(O)(OC(O)1N)CO | SMILES = O1(O)(OC(O)1N)CO
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| C=6 | H=13 | N=1 | O=5
| Formula = C<sub>6</sub>H<sub>13</sub>NO<sub>5</sub>
| Appearance =
| MolarMass = 179.171 g/mol
| Appearance = | Density =
| Density = | MeltingPtC = 180
| MeltingPt = 180 °C (HCl salt) | MeltingPt_notes = (HCl salt)
| BoilingPt = | BoilingPt =
| Solubility = | Solubility =
⚫ }}
⚫ | Section3 = {{Chembox Hazards
⚫ | MainHazards =
⚫ | FlashPt =
| Autoignition =
}} }}
⚫ |Section3={{Chembox Hazards
⚫ | MainHazards =
⚫ | FlashPt =
| AutoignitionPt =
⚫ }}
}} }}

'''Galactosamine''' is a ] derived from ] with the molecular formula C<sub>6</sub>H<sub>13</sub>NO<sub>5</sub>. This ] is a constituent of some ] ]s such as ] (FSH) and ] (LH).

Precursors such as ] (UDP), UDP-''N''-acetyl-<small>D</small>-glucosamine, or ] are used to synthesize galactosamine in the human body. A derivative of this compound is ].<ref name=":0"/>

Galactosamine is a ], or liver-damaging, agent that is sometimes used in ]s of ].

== Hepatotoxicity ==
Galactosamine is used to induce hepatitis in rodent liver for research purposes. The result of using galactosamine to induce hepatitis is a disease model in which there is ] and inflammation of the liver. This type of tissue damage triggered by galactosamine resembles drug-induced liver disease in humans.<ref name=":1">{{Cite journal |last1=Das |first1=Joydeep |last2=Ghosh |first2=Jyotirmoy |last3=Roy |first3=Anandita |last4=Sil |first4=Parames C. |date=April 2012 |title=Mangiferin exerts hepatoprotective activity against D-galactosamine induced acute toxicity and oxidative/nitrosative stress via Nrf2–NFκB pathways |url=https://linkinghub.elsevier.com/retrieve/pii/S0041008X12000269 |journal=Toxicology and Applied Pharmacology |language=en |volume=260 |issue=1 |pages=35–47 |doi=10.1016/j.taap.2012.01.015|pmid=22310181 }}</ref>

=== Mechanism of hepatotoxicity ===
The proposed mechanism behind galactosamine-induced hepatitis is depletion of the energy source of ]s. In the ] galactosamine is metabolized into galactosamine-1-phosphate (by ]) and UDP-galactosamine (by UDP-galactose ]). It is hypothesized that this leads to UDP-galactosamine accumulation within cells, and ] (UTP), UDP, and ] (UMP) decrease.<ref name=":0">{{Citation |last=Apte |first=U. |title=Galactosamine |date=2014 |url=https://linkinghub.elsevier.com/retrieve/pii/B9780123864543003158 |encyclopedia=Encyclopedia of Toxicology |pages=689–690 |publisher=Elsevier |language=en |doi=10.1016/b978-0-12-386454-3.00315-8 |isbn=978-0-12-386455-0 |access-date=2022-12-08}}</ref> The depletion of high-energy molecules such as UTP leads to a disruption in hepatocyte metabolism. Additionally, other derivatives of uridine such as UDP-glucose are depleted and this interferes with ] in the cell.

Another recent hypothesis states that overexpression of pro-inflammatory cytokines (such as ] (TNFα) and ]-dependent ] (iNOS) over expression play a role in galactosamine-induced damage to liver cells.<ref name=":1" />

==See also==
* ]
* ]

==References==
{{More citations needed|date=March 2012}}
{{Reflist}}

==External links==
* {{MeshName|Galactosamine}}

]