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Revision as of 10:00, 20 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{drugbox}} taken from revid 476697623 of page Spiramycin for the Chem/Drugbox validation project (updated: 'ChEMBL').  Latest revision as of 05:48, 4 January 2025 edit 45.36.135.31 (talk) →Available forms: removed edit error 
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{{Short description|Chemical compound}}
{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}}
{{cs1 config|name-list-style=vanc|display-authors-6}}
{{Drugbox {{Drugbox
| Verifiedfields = changed | Verifiedfields = changed
⚫ | verifiedrevid = 477859140
| Watchedfields = changed
⚫ | IUPAC_name = (4''R'',5''S'',6''R'',7''R'',9''R'',10''R'',11''E'',13''E'',16''R'')-10-<nowiki/>{oxy}-9,16-dimethyl-5-methoxy-2-oxo-7-(2-oxoethyl)oxacyclohexadeca-11,13-dien-6-yl 3,6-dideoxy-4-''O''-(2,6-dideoxy-3-''C''-methyl-α-<small>L</small>-''ribo''-hexopyranosyl)-3-(dimethylamino)-α-<small>D</small>-glucopyranoside
⚫ | verifiedrevid = 401063813
⚫ | IUPAC_name = (4''R'',5''S'',6''R'',7''R'',9''R'',10''R'',11''E'',13''E'',16''R'')-10-{oxy}-9,16-dimethyl-5-methoxy-2-oxo-7-(2-oxoethyl)oxacyclohexadeca-11,13-dien-6-yl 3,6-dideoxy-4-''O''-(2,6-dideoxy-3-''C''-methyl-α-<small>L</small>-''ribo''-hexopyranosyl)-3-(dimethylamino)-α-<small>D</small>-glucopyranoside
| image = Spiramycin I.svg | image = Spiramycin I.svg
| width = 350 | width = 350

<!--Clinical data--> <!--Clinical data-->
| tradename = | tradename =
| .com = {{ .com|CONS|spiramycin}}
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> | pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_US = <!-- A / B / C / D / X --> | pregnancy_US = <!-- A / B / C / D / X -->
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| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C --> | legal_UK = <!-- GSL / P / POM / CD / Class A, B, C -->
| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> | legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
| legal_status = | legal_status = rx only
| routes_of_administration = | routes_of_administration = oral

<!--Pharmacokinetic data--> <!--Pharmacokinetic data-->
| bioavailability = | bioavailability =
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| elimination_half-life = | elimination_half-life =
| excretion = | excretion =

<!--Identifiers--> <!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}} | CAS_number_Ref = {{cascite|correct|??}}
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| ATC_supplemental = {{ATCvet|J51|FA02}} | ATC_supplemental = {{ATCvet|J51|FA02}}
| PubChem = 5356392 | PubChem = 5356392
| DrugBank_Ref = {{ bankcite|correct|drugbank}} | DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = | DrugBank = DB06145
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 4512090 | ChemSpiderID = 4512090
| UNII_Ref = {{fdacite|changed|FDA}} | ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 85260
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 71ODY0V87H | UNII = 71ODY0V87H
| KEGG_Ref = {{keggcite|changed|kegg}} | KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D05908 | KEGG = D05908
| ChEMBL_Ref = {{ebicite|changed|EBI}} | ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = <!-- blanked - oldvalue: 1256397 --> | ChEMBL = 1256397
| NIAID_ChemDB = 007350 | NIAID_ChemDB = 007350

<!--Chemical data--> <!--Chemical data-->
| C=43 | H=74 | N=2 | O=14 | C=43 | H=74 | N=2 | O=14
| molecular_weight = 843.053 g/mol
| smiles = O=CCC4C(OC2OC(C(OC1OC(C)C(O)C(O)(C)C1)C(N(C)C)C2O)C)C(OC)C(O)CC(=O)OC(C)C\C=C\C=C\C(OC3OC(C)C(N(C)C)CC3)C(C)C4 | smiles = O=CCC4C(OC2OC(C(OC1OC(C)C(O)C(O)(C)C1)C(N(C)C)C2O)C)C(OC)C(O)CC(=O)OC(C)C\C=C\C=C\C(OC3OC(C)C(N(C)C)CC3)C(C)C4
| InChI = 1/C43H74N2O14/c1-24-21-29(19-20-46)39(59-42-37(49)36(45(9)10)38(27(4)56-42)58-35-23-43(6,51)41(50)28(5)55-35)40(52-11)31(47)22-33(48)53-25(2)15-13-12-14-16-32(24)57-34-18-17-30(44(7)8)26(3)54-34/h12-14,16,20,24-32,34-42,47,49-51H,15,17-19,21-23H2,1-11H3/b13-12+,16-14+
| InChIKey = ACTOXUHEUCPTEW-OBURPCBNBW
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C43H74N2O14/c1-24-21-29(19-20-46)39(59-42-37(49)36(45(9)10)38(27(4)56-42)58-35-23-43(6,51)41(50)28(5)55-35)40(52-11)31(47)22-33(48)53-25(2)15-13-12-14-16-32(24)57-34-18-17-30(44(7)8)26(3)54-34/h12-14,16,20,24-32,34-42,47,49-51H,15,17-19,21-23H2,1-11H3/b13-12+,16-14+ | StdInChI = 1S/C43H74N2O14/c1-24-21-29(19-20-46)39(59-42-37(49)36(45(9)10)38(27(4)56-42)58-35-23-43(6,51)41(50)28(5)55-35)40(52-11)31(47)22-33(48)53-25(2)15-13-12-14-16-32(24)57-34-18-17-30(44(7)8)26(3)54-34/h12-14,16,20,24-32,34-42,47,49-51H,15,17-19,21-23H2,1-11H3/b13-12+,16-14+
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = ACTOXUHEUCPTEW-OBURPCBNSA-N | StdInChIKey = ACTOXUHEUCPTEW-OBURPCBNSA-N
| synonyms = <small>2-oxy}-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-10-{oxy}-4-hydroxy-5-methoxy-9,16-dimethyl-2-oxo-1-oxacyclohexadeca-11,13-dien-7-yl]acetaldehyde</small>
| solubility = Insoluble in water; Very soluble in acetonitrile and methanol; Almost completely(>99.5) in ethanol. | solubility = Insoluble in water; Very soluble in acetonitrile and methanol; Almost completely(>99.5) in ethanol.
| melting_point = 134
| melting_high = 137
}} }}

'''Spiramycin''' is a ] antibiotic and antiparasitic. It is used to treat ] and various other infections of soft tissues.

Although used in Europe, Canada and Mexico,<ref>{{cite web | url = https://www.drugs.com/cons/spiramycin.html | title = Spiramycin advanced consumer information | work = Drugs.com}}</ref> spiramycin is still considered an experimental drug in the United States, but can sometimes be obtained by special permission from the FDA for toxoplasmosis in the first trimester of pregnancy.<ref name = "MayoClinic_Toxoplasmosis" />
Spiramycin has been used in Europe since the year 2000 under the ] "Rovamycine", produced by Rhone-Poulenc Rorer, Sanofi and Famar Lyon, France and Eczacıbaşı İlaç, Turkey. It also goes under the name Rovamycine in Canada (distributed by ]), where it is mostly marketed to dentists for mouth infections.{{cn|date=March 2023}} Spiramycin has been studied as a virulence inhibitor in '']''.<ref>{{cite journal | vauthors = Calcagnile M, Jeguirim I, Tredici SM, Damiano F, Alifano P | title = Spiramycin Disarms <i>Pseudomonas aeruginosa</i> without Inhibiting Growth | journal = Antibiotics | volume = 12 | issue = 3 | pages = 499 | date = March 2023 | pmid = 36978366 | pmc = 10044227 | doi = 10.3390/antibiotics12030499 | doi-access = free }}</ref>

== Medical uses ==

=== Available forms ===

It is available for parenteral and oral administration.{{cn|date=March 2023}} Another treatment option (typically used after 16w gestation) are a combination of ] and ] (given with ]).<ref name = "MayoClinic_Toxoplasmosis">{{cite web | url = http://www.mayoclinic.com/health/toxoplasmosis/DS00510/DSECTION=8 | title = Toxoplasmosis | work = MayoClinic.com }}</ref>

== Pharmacology ==

=== Pharmacodynamics ===

The antibiotic action involves inhibition of protein synthesis in the bacterial cell during translocation. Resistance to spiramycin can develop by several mechanisms and its prevalence is to a considerable extent proportional to the frequency of prescription in a given area. The antibacterial spectrum comprises Gram-positive cocci and rods, Gram-negative cocci and also Legionellae, mycoplasmas, chlamydiae, some types of spirochetes, Toxoplasma gondii and Cryptosporidium species. Enterobacteria, pseudomonads and pathogenic moulds are resistant. Its action is mainly bacteriostatic, on highly sensitive strains it exerts a bactericide action. As compared with erythromycin, it is in vitro weight for weight 5 to 20 less effective, an equipotential therapeutic dose is, however, only double. This difference between the effectiveness in vitro and in vivo is explained above all by the great affinity of spiramycin to tissues where it achieves concentrations many times higher than serum levels. An important part is played also by the slow release of the antibiotic from the tissue compartment, the marked action on microbes in sub-inhibition concentrations and the relatively long persisting post-antibiotic effect. Its great advantage is the exceptionally favourable tolerance-gastrointestinal and general.

== Chemistry ==

Spiramycin is a 16-membered ring macrolide.<ref name ="toku-e">{{Cite web|url=https://www.toku-e.com/product/spiramycin/|title=Spiramycin|website=www.toku-e.com|access-date=2019-02-28}}</ref><ref name = "Parker_2022">{{cite report | work = Name Abstract | title = Streptomyces ambofaciens Pinnert-Sindico 1954 (Approved Lists 1980) emend. Nouioui et al. 2018. | publisher = NamesforLife, LLC | date = 18 August 2022 | doi = 10.1601/nm.6849 | veditors = Parker CT, Mannor K, Garrity GM | vauthors = Parker CT, Garrity GM }}</ref>

== History ==

It was isolated in 1954 as a product of ''Streptomyces ambofaciens'' by PINNERT-SINDICO.<ref name ="toku-e" /><ref name = "Parker_2022" /> As a preparation for oral administration it has been used since 1955, in 1987 also the parenteral form was introduced into practice.

==References==
{{Reflist}}

{{Macrolides, lincosamides and streptogramins}}

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