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Revision as of 16:10, 6 December 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,081 edits Saving copy of the {{drugbox}} taken from revid 456611913 of page Spectinomycin for the Chem/Drugbox validation project (updated: 'DrugBank').  Latest revision as of 14:54, 12 January 2025 edit Arthurfragoso (talk | contribs)Extended confirmed users, Template editors4,591 edits dark mode fix 
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{{Short description|Antibiotic}}
{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}}
{{Drugbox {{Drugbox
| Verifiedfields = changed | Verifiedfields = changed
| verifiedrevid = 401063336 | verifiedrevid = 464405974
| IUPAC_name = (1''R'',3''S'',5''R'',8''R'',10''R'',11''S'',12''S'',13''R'',14''S'')-8,12,14-trihydroxy-5-methyl-11,13-''bis''(methylamino)-2,4,9-trioxatricyclotetradecan-7-one | IUPAC_name = (1''R'',3''S'',5''R'',8''R'',10''S'',11''S'',12''S'',13''R'',14''S'')-8,12,14-trihydroxy-5-methyl-11,13-''bis''(methylamino)-2,4,9-trioxatricyclotetradecan-7-one
| image = Spectinomycin.svg | image = Spectinomycin.svg
| image_class = skin-invert-image


<!--Clinical data--> <!--Clinical data-->
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| Drugs.com = {{drugs.com|monograph|spectinomycin-hydrochloride}} | Drugs.com = {{drugs.com|monograph|spectinomycin-hydrochloride}}
| pregnancy_US = B | pregnancy_US = B
| legal_status = not available in US | legal_US_comment = not available
| routes_of_administration = | routes_of_administration = ]


<!--Pharmacokinetic data--> <!--Pharmacokinetic data-->
| bioavailability = | bioavailability =
| protein_bound = | protein_bound =
| metabolism = | metabolism =


<!--Identifiers--> <!--Identifiers-->
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| PubChem = 15541 | PubChem = 15541
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB00919 | DrugBank = DB00919
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 14785 | ChemSpiderID = 14785
| UNII_Ref = {{fdacite|changed|FDA}} | UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 93AKI1U6QF | UNII = 93AKI1U6QF
| KEGG_Ref = {{keggcite|changed|kegg}} | KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D08526 | KEGG = D08526
| ChEMBL_Ref = {{ebicite|changed|EBI}} | ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 9215
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 1167 | ChEMBL = 1167


<!--Chemical data--> <!--Chemical data-->
| C=14 | H=24 | N=2 | O=7 | C=14 | H=24 | N=2 | O=7
| molecular_weight = 332.35 g/mol
| smiles = O=C12(O3(NC)(O)(NC)(O)3O2O(C1)C)O | smiles = O=C12(O3(NC)(O)(NC)(O)3O2O(C1)C)O
| InChI = 1/C14H24N2O7/c1-5-4-6(17)14(20)13(21-5)22-12-10(19)7(15-2)9(18)8(16-3)11(12)23-14/h5,7-13,15-16,18-20H,4H2,1-3H3/t5-,7-,8+,9+,10+,11-,12-,13+,14+/m1/s1
| InChIKey = UNFWWIHTNXNPBV-WXKVUWSEBO
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C14H24N2O7/c1-5-4-6(17)14(20)13(21-5)22-12-10(19)7(15-2)9(18)8(16-3)11(12)23-14/h5,7-13,15-16,18-20H,4H2,1-3H3/t5-,7-,8+,9+,10+,11-,12-,13+,14+/m1/s1 | StdInChI = 1S/C14H24N2O7/c1-5-4-6(17)14(20)13(21-5)22-12-10(19)7(15-2)9(18)8(16-3)11(12)23-14/h5,7-13,15-16,18-20H,4H2,1-3H3/t5-,7-,8+,9+,10+,11-,12-,13+,14+/m1/s1
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = UNFWWIHTNXNPBV-WXKVUWSESA-N | StdInChIKey = UNFWWIHTNXNPBV-WXKVUWSESA-N
| synonyms = <small>(2''R'',4a''R'',5a''R'',6''S'',7''S'',8''R'',9''S'',9a''R'',10a''S'')-4a,7,9-trihydroxy-2-methyl-6,8-''bis''(methylamino)decahydro-4''H''-pyranobenzodioxin-4-one</small> | synonyms = <small>(2''R'',4a''R'',5a''R'',6''S'',7''S'',8''R'',9''S'',9a''R'',10a''S'')-4a,7,9-trihydroxy-2-methyl-6,8-''bis''(methylamino)decahydro-4''H''-pyranobenzodioxin-4-one</small> , SPT/SPE/SC/SP<ref>{{cite web |title=Antibiotic abbreviations list |url=https://microbiologie-clinique.com/antibiotic-family-abbreviation.html |access-date=22 June 2023}}</ref>
| melting_point = 184
| melting_high = 194
}} }}
<!-- Definition and medical uses -->
'''Spectinomycin''', sold under the tradename '''Trobicin''' among others, is an ] useful for the treatment of ]s.<ref name=AHFS2015>{{cite web|title=Spectinomycin Hydrochloride|url=https://www.drugs.com/monograph/spectinomycin-hydrochloride.html|publisher=The American Society of Health-System Pharmacists|access-date=Sep 6, 2015|url-status=live|archive-url=https://web.archive.org/web/20150924003846/http://www.drugs.com/monograph/spectinomycin-hydrochloride.html|archive-date=2015-09-24}}</ref> It is given by injection into a muscle.<ref name=AHFS2015/>

<!-- Side effects -->
Common side effects include pain at the area of injection, rash, nausea, fever, and trouble sleeping.<ref name=AHFS2015/> Severe ]s may occasionally occur.<ref name=AHFS2015/> It is generally safe to use during pregnancy.<ref name=AHFS2015/> It may be used by those who are allergic to ] or ]s.<ref name=AHFS2015/> It is in the ] class of drugs and works by stopping the making of protein by certain bacteria.<ref name=AHFS2015/>

<!-- Society and culture -->
Spectinomycin was discovered in 1961.<ref name=CDC2009>{{cite book|title=Textbook of Drug Design and Discovery, Fourth Edition|date=2009|publisher=CRC Press|isbn=9781439882405|page=438|url=https://books.google.com/books?id=YLPMBQAAQBAJ&pg=PA438|url-status=live|archive-url=https://web.archive.org/web/20151003225200/https://books.google.ca/books?id=YLPMBQAAQBAJ&pg=PA438|archive-date=2015-10-03}}</ref> It is on the ].<ref name="WHO21st">{{cite book | vauthors = ((World Health Organization)) | title = World Health Organization model list of essential medicines: 21st list 2019 | year = 2019 | hdl = 10665/325771 | author-link = World Health Organization | publisher = World Health Organization | location = Geneva | id = WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO | hdl-access=free }}</ref> It is not available in the United States for human use.<ref name=AHFS2015/> It is made from the ] '']''.<ref name=AHFS2015/>

==Medical uses==
It is given by ] to treat ], especially in patients who are allergic to ]s.

This antibiotic is no longer available in the United States for human use, but is still available for veterinary use.

==Side effects==
Side effects include ], ], stomach ache, and ].

==Mechanism of action==
Spectinomycin binds to the ] subunit of the bacterial ] and interrupts protein synthesis.
One form of resistance has emerged in the ] in '']''.<ref name="pmid17371823">{{cite journal |vauthors=Kehrenberg C, Schwarz S |title=Mutations in 16S rRNA and ribosomal protein S5 associated with high-level spectinomycin resistance in Pasteurella multocida |journal=Antimicrob. Agents Chemother. |volume=51 |issue=6 |pages=2244–6 |date=June 2007 |pmid=17371823 |pmc=1891365 |doi=10.1128/AAC.00229-07 }}</ref>

==Biosynthetic mechanism==
]

Biosynthesis of spectinomycin begins similarly to the aminoglycosides, with the formation of an ] ring. The difference is the initial modification that forms the inositol ring of spectinomycin. The process begins with a ] (1a), which is oxidized by ] to form a ] at C2 (2a). This ketone is then formed into a primary ] group through ] (PLP) and glutamine transamination (3a). This process is repeated again at C4 to form a second primary amine (4a). Once these two amines are present, the glucose ring is ready to be ] through two ] molecules (5a). With this methylation, the glucose ring is finally ready to be converted into an inositol ring through inositol cyclase (6a). This can then be hydrolyzed to get rid of the phosphate group, making the inositol ring necessary for spectinomycin (7a).

While all this happens, an alternate pathway is occurring creating the sugar functional group from a similar starting product. In this pathway, ] is used as the starting product (1b). This is converted into a ] through TDP synthase (2b). TDP glucose then has the hydroxyl removed from C6 through a hydratase enzyme (3b), which is then reduced through NADH at C4 creating a new product (4b). With this ketone present, PLP and glutamine can come in to convert it to a primary amine (5b) which can then be removed through a deaminase (6b). This conversion to 6b is also accompanied by a double reduction at C4 and C3 through two more NADH molecules, giving the final product necessary to form the aminoglycoside. With this, products 7a and 6b can come together, removing the TDP functional group and combining with the sugar molecule to form the aminoglycoside spectinomycin.<ref>{{cite book |last=Dewick |first=Paul M. |date=4 Feb 2009 |title=Medicinal Natural Products: A Biosynthetic Approach, 3rd Edition |url=https://archive.org/details/medicinalnatural00dewi_880 |url-access=limited |location=Wiley Online Library |publisher=Wiley |pages=–508 |isbn=9780470741689 |doi=10.1002/9780470742761 }}</ref>

===Nature===
It is in ] class, closely related to the ]. Spectinomycin is industrially produced by fermentation of the ] '']''. Spectinomycin is produced in nature by many organisms including cyanobacteria and various plant species.{{cn|date=January 2022}} It is present in the ] or ] of many plastids as the spc ], which is usually two to 10 genes long. The difference in size may be due to the elimination of obsolete genes or the takeover of its function by nuclear genes. Spectinomycin is mainly produced by organisms as a ] against predators.

==History==
Spectinomycin was discovered 1961.<ref name=CDC2009/> A disruption in the supply occurred in 2001.<ref name="pmid11575327">{{cite journal |title=From the Centers for Disease Control and Prevention. Update on spectinomycin availability in the United States |journal=JAMA |volume=286 |issue=11 |pages=1308–9 |date=September 2001 |pmid=11575327 |doi= 10.1001/jama.286.11.1308|doi-access=free }}</ref>

==References==
{{reflist}}

{{Other antibacterials}}
{{Portal bar|Medicine}}

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