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Revision as of 11:05, 17 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 464126328 of page Alpha-Melanocyte-stimulating_hormone for the Chem/Drugbox validation project (updated: 'ChEMBL', 'CASNo').  Latest revision as of 17:58, 15 September 2024 edit SilverLocust (talk | contribs)Administrators25,050 edits cleanup from move 
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{{short description|Peptide hormone in Homo sapiens}}
{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
{{lowercase title}}
{{Chembox {{Chembox
| Verifiedfields = changed
| ImageFile =
| Watchedfields = changed
⚫ | ImageSize =
| Name = α-Melanocyte-stimulating hormone
⚫ | IUPACName = ''N''-acetyl-<small>L</small>-seryl-<small>L</small>-tyrosyl-<small>L</small>-seryl-<small>L</small>-methionyl-<small>L</small>-α-glutamyl-<small>L</small>-histidyl-<small>D</small>-phenylalanyl-<small>L</small>-arginyl-<small>L</small>-tryptophylglycyl-<small>L</small>-lysyl-<small>L</small>-prolyl-<small>L</small>-valinamide
| verifiedrevid = 477348553
⚫ | OtherNames = Ac-Ser-Tyr-Ser-Met-Glu-His-Phe-Arg-Trp-Gly-Lys-Pro-Val-NH<sub>2</sub>
| ImageFile = α-melanocyte-stimulating_hormone.svg
⚫ | Section1 = {{Chembox Identifiers
⚫ | ImageSize = 300px
| CASNo = <!-- blanked - oldvalue: 581-05-5 -->
⚫ | IUPACName = ''N''-acetyl-<small>L</small>-seryl-<small>L</small>-tyrosyl-<small>L</small>-seryl-<small>L</small>-methionyl-<small>L</small>-α-glutamyl-<small>L</small>-histidyl-<small>L</small>-phenylalanyl-<small>L</small>-arginyl-<small>L</small>-tryptophylglycyl-<small>L</small>-lysyl-<small>L</small>-prolyl-<small>L</small>-valinamide
⚫ | ChEMBL = 385886
⚫ | OtherNames = alpha-MSH, α-melanocortin, α-melanotropin, α-intermedin; Ac-Ser-Tyr-Ser-Met-Glu-His-Phe-Arg-Trp-Gly-Lys-Pro-Val-NH<sub>2</sub>
⚫ | PubChem = 16132636
⚫ | Section1 = {{Chembox Identifiers
⚫ | ChemSpiderID = 17289286
| CASNo_Ref = {{cascite|correct|CAS}}
⚫ | SMILES =
| CASNo = 581-05-5
⚫ | InChI = 1/C77H109N21O19S/c1-42(2)64(65(79)106)97-75(116)61-20-13-30-98(61)76(117)54(18-10-11-28-78)88-62(103)38-85-66(107)57(34-46-36-84-50-17-9-8-16-49(46)50)94-67(108)51(19-12-29-83-77(80)81)89-70(111)55(32-44-14-6-5-7-15-44)92-72(113)58(35-47-37-82-41-86-47)95-68(109)52(25-26-63(104)105)90-69(110)53(27-31-118-4)91-74(115)60(40-100)96-71(112)56(33-45-21-23-48(102)24-22-45)93-73(114)59(39-99)87-43(3)101/h5-9,14-17,21-24,36-37,41-42,51-61,64,84,99-100,102H,10-13,18-20,25-35,38-40,78H2,1-4H3,(H2,79,106)(H,82,86)(H,85,107)(H,87,101)(H,88,103)(H,89,111)(H,90,110)(H,91,115)(H,92,113)(H,93,114)(H,94,108)(H,95,109)(H,96,112)(H,97,116)(H,104,105)(H4,80,81,83)
| UNII_Ref = {{fdacite|correct|FDA}}
⚫ | InChIKey = WHNFPRLDDSXQCL-UHFFFAOYAP
| UNII = OVF025LA77
⚫ | StdInChI = 1S/C77H109N21O19S/c1-42(2)64(65(79)106)97-75(116)61-20-13-30-98(61)76(117)54(18-10-11-28-78)88-62(103)38-85-66(107)57(34-46-36-84-50-17-9-8-16-49(46)50)94-67(108)51(19-12-29-83-77(80)81)89-70(111)55(32-44-14-6-5-7-15-44)92-72(113)58(35-47-37-82-41-86-47)95-68(109)52(25-26-63(104)105)90-69(110)53(27-31-118-4)91-74(115)60(40-100)96-71(112)56(33-45-21-23-48(102)24-22-45)93-73(114)59(39-99)87-43(3)101/h5-9,14-17,21-24,36-37,41-42,51-61,64,84,99-100,102H,10-13,18-20,25-35,38-40,78H2,1-4H3,(H2,79,106)(H,82,86)(H,85,107)(H,87,101)(H,88,103)(H,89,111)(H,90,110)(H,91,115)(H,92,113)(H,93,114)(H,94,108)(H,95,109)(H,96,112)(H,97,116)(H,104,105)(H4,80,81,83)
| ChEMBL_Ref = {{ebicite|correct|EBI}}
⚫ | StdInChIKey = WHNFPRLDDSXQCL-UHFFFAOYSA-N
⚫ | ChEMBL = 214332
| ChEBI = 195325
⚫ | PubChem = 16133793
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
⚫ | ChemSpiderID = 17288804
⚫ | SMILES =
⚫ | InChI = 1/C77H109N21O19S/c1-42(2)64(65(79)106)97-75(116)61-20-13-30-98(61)76(117)54(18-10-11-28-78)88-62(103)38-85-66(107)57(34-46-36-84-50-17-9-8-16-49(46)50)94-67(108)51(19-12-29-83-77(80)81)89-70(111)55(32-44-14-6-5-7-15-44)92-72(113)58(35-47-37-82-41-86-47)95-68(109)52(25-26-63(104)105)90-69(110)53(27-31-118-4)91-74(115)60(40-100)96-71(112)56(33-45-21-23-48(102)24-22-45)93-73(114)59(39-99)87-43(3)101/h5-9,14-17,21-24,36-37,41-42,51-61,64,84,99-100,102H,10-13,18-20,25-35,38-40,78H2,1-4H3,(H2,79,106)(H,82,86)(H,85,107)(H,87,101)(H,88,103)(H,89,111)(H,90,110)(H,91,115)(H,92,113)(H,93,114)(H,94,108)(H,95,109)(H,96,112)(H,97,116)(H,104,105)(H4,80,81,83)
⚫ | InChIKey = WHNFPRLDDSXQCL-UHFFFAOYAP
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
⚫ | StdInChI = 1S/C77H109N21O19S/c1-42(2)64(65(79)106)97-75(116)61-20-13-30-98(61)76(117)54(18-10-11-28-78)88-62(103)38-85-66(107)57(34-46-36-84-50-17-9-8-16-49(46)50)94-67(108)51(19-12-29-83-77(80)81)89-70(111)55(32-44-14-6-5-7-15-44)92-72(113)58(35-47-37-82-41-86-47)95-68(109)52(25-26-63(104)105)90-69(110)53(27-31-118-4)91-74(115)60(40-100)96-71(112)56(33-45-21-23-48(102)24-22-45)93-73(114)59(39-99)87-43(3)101/h5-9,14-17,21-24,36-37,41-42,51-61,64,84,99-100,102H,10-13,18-20,25-35,38-40,78H2,1-4H3,(H2,79,106)(H,82,86)(H,85,107)(H,87,101)(H,88,103)(H,89,111)(H,90,110)(H,91,115)(H,92,113)(H,93,114)(H,94,108)(H,95,109)(H,96,112)(H,97,116)(H,104,105)(H4,80,81,83)
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
⚫ | StdInChIKey = WHNFPRLDDSXQCL-UHFFFAOYSA-N
}} }}
| Section2 = {{Chembox Properties | Section2 = {{Chembox Properties
| Formula = C<sub>77</sub>H<sub>109</sub>N<sub>21</sub>O<sub>19</sub>S | Formula = C<sub>77</sub>H<sub>109</sub>N<sub>21</sub>O<sub>19</sub>S
| MolarMass = 1664.884 g/mol | MolarMass = 1664.884 g/mol
| Appearance = | Appearance =
| Density = | Density =
| MeltingPt = | MeltingPt =
| BoilingPt = | BoilingPt =
| Solubility = | Solubility =
}} }}
| Section3 = {{Chembox Hazards | Section3 = {{Chembox Hazards
| MainHazards = | MainHazards =
| FlashPt = | FlashPt =
| Autoignition = | AutoignitionPt =
}}
| Section5 = {{Chembox Pharmacology
| HalfLife = 20 minutes<ref name="pmid20545686">{{cite journal | author = Langan EA, Nie Z, Rhodes LE | title = Melanotropic peptides: more than just 'Barbie drugs' and 'sun-tan jabs'? | journal = The British Journal of Dermatology | volume = 163 | issue = 3 | pages = 451–5 | year = 2010 | month = September | pmid = 20545686 | doi = 10.1111/j.1365-2133.2010.09891.x | url = http://onlinelibrary.wiley.com/resolve/openurl?genre=article&sid=nlm:pubmed&issn=0007-0963&date=2010&volume=163&issue=3&spage=451}}</ref>
}} }}
}} }}

'''α-Melanocyte-stimulating hormone''' ('''α-MSH''') is an ] ] and ] of the ] family, with a ] ] and the ] Ac-Ser-Tyr-Ser-Met-Glu-His-Phe-Arg-Trp-Gly-Lys-Pro-Val-NH<sub>2</sub>. It is the most important of the ]s (MSHs) (also known as melanotropins) in stimulating ], a process that in ]s (including ]s) is responsible for ] primarily of the ] and ]. It also plays a role in ], ], ], and protection against ] and ].<ref>{{cite journal |title= Protective effect of alpha-melanocyte-stimulating hormone (α-MSH) on the recovery of ischemia/reperfusion (I/R)-induced retinal damage in a rat model |last1=Varga |first1=B. |last2=Gesztelyi |first2=R. |last3=Bombicz |first3=M. |last4=Haines |first4=D. |last5=Szabo |first5=A. M. |last6=Kemeny-Beke |first6=A. |last7=Antal |first7=M. |last8=Vecsernyes |first8=M. |last9=Juhasz |first9=B. |last10=Tosaki |first10=A. |journal=] |volume=50 |issue=3 |pages=558–70 |date=July 2013 | pmid = 23504281 | doi = 10.1007/s12031-013-9998-3 |pmc=3675276}}</ref>

α-MSH is a ] ] of the ]s ] (K<sub>i</sub> = 0.230 nM), ] (K<sub>i</sub> = 31.5 nM), ] (K<sub>i</sub> = 900 nM), and ] (K<sub>i</sub> = 7160 nM), but not ] (which is exclusive for ] (ACTH)).<ref name="SchiöthMutulis1998">{{cite journal|last1=Schiöth|first1=Helgi B|last2=Mutulis|first2=Felikss|last3=Muceniece|first3=Ruta|last4=Prusis|first4=Peteris|last5=Wikberg|first5=Jarl E S|title=Discovery of novel melanocortin4receptor selective MSH analogues|journal=British Journal of Pharmacology|volume=124|issue=1|year=1998|pages=75–82|issn=0007-1188|doi=10.1038/sj.bjp.0701804|pmc=1565364|pmid=9630346}}</ref> Activation of the MC<sub>1</sub> receptor is responsible for its effect on pigmentation, whereas its regulation of appetite, metabolism, and sexual behavior is mediated through both the MC<sub>3</sub> and MC<sub>4</sub> receptors.

It is generated as a ] ] from ACTH (1-13), which is in turn a cleavage product of ] (POMC).

A few ] ]s of α-MSH have been investigated as ] ]s due to their ] effects against ] from the sun. They include ] (melanotan) and ], the former of which has been approved as a treatment to reduce ] in ] in the ].<ref name=Oct2019FDA>{{cite press release |title=FDA approves first treatment to increase pain-free light exposure in patients with a rare disorder|url=https://www.fda.gov/news-events/press-announcements/fda-approves-first-treatment-increase-pain-free-light-exposure-patients-rare-disorder|date=8 October 2019|archive-url=https://web.archive.org/web/20191009122611/https://www.fda.gov/news-events/press-announcements/fda-approves-first-treatment-increase-pain-free-light-exposure-patients-rare-disorder|archive-date=9 October 2019 |url-status=live}}</ref> ], another analogue of α-MSH, is available in the United States not as a photoprotective agent, but for the treatment of ] in premenopausal women.<ref name="MyUser_Https:_August_4_2021c">{{cite web |url=https://www.fda.gov/news-events/press-announcements/fda-approves-new-treatment-hypoactive-sexual-desire-disorder-premenopausal-women |title=FDA approves new treatment for hypoactive sexual desire disorder in premenopausal women |newspaper=Https |date= 24 March 2020|author= |accessdate= August 4, 2021}}</ref> All of these drugs have significantly greater ] than α-MSH, along with improved ]s and distinctive ] profiles.

==See also==
* ]
* ]
* ]

==References==
{{Reflist|2}}

{{Hormones}}
{{Neuropeptides}}
{{Melanocortin receptor modulators}}

{{DEFAULTSORT:Melanocyte-stimulating hormone, α-}}
]
]
]