Spiramycin: Difference between revisions

Spiramycin
Clinical data
Routes of; administration	oral
ATC code	J01FA02 (WHO) QJ51FA02 (WHO);
Legal status
Legal status	In general: ℞ (Prescription only);
Identifiers
	IUPAC name (4R,5S,6R,7R,9R,10R,11E,13E,16R)-10-{[(2R,5S,6R)-5-(dimethylamino)-6-methyltetrahydro-2H-pyran-2-yl]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-L-ribo-hexopyranosyl)-3-(dimethylamino)-α-D-glucopyranoside;
CAS Number	8025-81-8 ;
PubChem CID	5356392;
ChemSpider	4512090 ;
UNII	71ODY0V87H;
KEGG	D05908 ;
ChEBI	CHEBI:85260 ;
ChEMBL	ChEMBL1256397 ;
NIAID ChemDB	007350;
E number	E710 (antibiotics)
CompTox Dashboard (EPA)	DTXSID6045402 ;
ECHA InfoCard	100.029.476
Chemical and physical data
Formula	C43H74N2O14
Molar mass	843.065 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	134 to 137 °C (273 to 279 °F)
Solubility in water	Insoluble in water; Very soluble in acetonitrile and methanol; Almost completely(>99.5) in ethanol. mg/mL (20 °C)
	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 InChI=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+ ; Key:ACTOXUHEUCPTEW-OBURPCBNSA-N ;
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Spiramycin is a macrolide antibiotic and antiparasitic. It is used to treat toxoplasmosis and various other infections of soft tissues.

Although used in Europe, Canada and Mexico,^[1] 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.^[2] Spiramycin has been used in Europe since the year 2000 under the trade name "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 OdanLaboratories), where it is mostly marketed to dentists for mouth infections.^{[citation needed]} Spiramycin has been studied as a virulence inhibitor in Pseudomonas aeruginosa.^[3]

Medical uses

Available forms

It is available for parenteral and oral administration.^{[citation needed]} Another treatment option (typically used after 16w gestation) are a combination of pyrimethamine and sulfadiazine (given with leucovorin).^[2] Spiramycin

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.^[4]^[5]

History

It was isolated in 1954 as a product of Streptomyces ambofaciens by PINNERT-SINDICO.^[4]^[5] As a preparation for oral administration it has been used since 1955, in 1987 also the parenteral form was introduced into practice.

References

^ "Spiramycin advanced consumer information". Drugs.com.
^ ^a ^b "Toxoplasmosis". MayoClinic.com.
^ Calcagnile M, Jeguirim I, Tredici SM, Damiano F, Alifano P (March 2023). "Spiramycin Disarms Pseudomonas aeruginosa without Inhibiting Growth". Antibiotics. 12 (3): 499. doi:10.3390/antibiotics12030499. PMC 10044227. PMID 36978366.
^ ^a ^b "Spiramycin". www.toku-e.com. Retrieved 2019-02-28.
^ ^a ^b Parker CT, Garrity GM (18 August 2022). Parker CT, Mannor K, Garrity GM (eds.). Streptomyces ambofaciens Pinnert-Sindico 1954 (Approved Lists 1980) emend. Nouioui et al. 2018. Name Abstract (Report). NamesforLife, LLC. doi:10.1601/nm.6849 (inactive 2024-04-17).{{cite report}}: CS1 maint: DOI inactive as of April 2024 (link)

[1] "Spiramycin advanced consumer information". Drugs.com.

[MayoClinic_Toxoplasmosis-2] "Toxoplasmosis". MayoClinic.com.

[3] Calcagnile M, Jeguirim I, Tredici SM, Damiano F, Alifano P (March 2023). "Spiramycin Disarms Pseudomonas aeruginosa without Inhibiting Growth". Antibiotics. 12 (3): 499. doi:10.3390/antibiotics12030499. PMC 10044227. PMID 36978366.

[toku-e-4] "Spiramycin". www.toku-e.com. Retrieved 2019-02-28.

[Parker_2022-5] Parker CT, Garrity GM (18 August 2022). Parker CT, Mannor K, Garrity GM (eds.). Streptomyces ambofaciens Pinnert-Sindico 1954 (Approved Lists 1980) emend. Nouioui et al. 2018. Name Abstract (Report). NamesforLife, LLC. doi:10.1601/nm.6849 (inactive 2024-04-17).{{cite report}}: CS1 maint: DOI inactive as of April 2024 (link)

[1]

[2]

[3]

[4]

[5]

@@ Line 1: / Line 1: @@
+{{Short description|Chemical compound}}
+{{cs1 config|name-list-style=vanc|display-authors-6}}
 {{Drugbox
 | 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/>{[(2''R'',5''S'',6''R'')-5-(dimethylamino)-6-methyltetrahydro-2''H''-pyran-2-yl]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-{[(2''R'',5''S'',6''R'')-5-(dimethylamino)-6-methyltetrahydro-2''H''-pyran-2-yl]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
 | width = 350
 <!--Clinical data-->
 | tradename =
-|      .com = {{     .com|CONS|spiramycin}}
 | pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
 | pregnancy_US = <!-- A / B            / C / D / X -->
@@ Line 17: / Line 16: @@
 | legal_UK = <!-- GSL         / P       / POM / CD / Class A, B, C -->
 | 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-->
 | bioavailability =
@@ Line 26: / Line 24: @@
 | elimination_half-life =
 | excretion =
 <!--Identifiers-->
 | CAS_number_Ref = {{cascite|correct|??}}
@@ Line 34: / Line 31: @@
 | ATC_supplemental =  {{ATCvet|J51|FA02}}
 | PubChem = 5356392
-| DrugBank_Ref = {{    bankcite|correct|drugbank}}
+| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
 | DrugBank =
 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
 | ChemSpiderID = 4512090
-| UNII_Ref = {{fdacite|changed|FDA}}
+| ChEBI_Ref = {{ebicite|changed|EBI}}
+| ChEBI = 85260
+| UNII_Ref = {{fdacite|correct|FDA}}
 | UNII = 71ODY0V87H
-| KEGG_Ref = {{keggcite|changed|kegg}}
+| KEGG_Ref = {{keggcite|correct|kegg}}
 | KEGG = D05908
 | ChEMBL_Ref = {{ebicite|changed|EBI}}
 | ChEMBL = 1256397
 | NIAID_ChemDB = 007350
 <!--Chemical data-->
 | 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
-| 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 = 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 = ACTOXUHEUCPTEW-OBURPCBNSA-N
-| synonyms = <small>2-[(4''R'',5''S'',6''S'',7''R'',9''R'',10''R'',11''E'',13''E'',16''R'')-6-{[(2''S'',3''R'',4''R'',5''S'',6''R'')-5-{[(2''S'',5''S'',6''S'')-4,5-dihydroxy-4,6-dimethyloxan-2-yl]oxy}-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-10-{[(2''R'',5''S'',6''R'')-5-(dimethylamino)-6-methyloxan-2-yl]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.
+| melting_point = 134
+| melting_high = 137
 }}
+'''Spiramycin''' is a [[macrolide]] antibiotic and antiparasitic. It is used to treat [[toxoplasmosis]] and various other infections of soft tissues.
-'''Spiramycin''' is a [[macrolide]] antibiotic. It is used to treat [[toxoplasmosis]]. Although used in Europe, Canada and Mexico<ref>[http://www.drugs.com/cons/spiramycin.html Spiramycin advanced consumer information | Drugs.com<!-- Bot generated title -->]</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>[http://www.mayoclinic.com/health/toxoplasmosis/DS00510/DSECTION=8 Toxoplasmosis] at MayoClinic.com</ref>
+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 [[trade name]] "Rovamycine", produced by Rhone-Poulenc Rorer and Famar Lyon, France and Eczacibasi Ilae, Turkey.
+Spiramycin has been used in Europe since the year 2000 under the [[trade name]] "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 [[OdanLaboratories]]), where it is mostly marketed to dentists for mouth infections.{{cn|date=March 2023}} Spiramycin has been studied as a virulence inhibitor in ''[[Pseudomonas aeruginosa]]''.<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 ==
-Spiramycin is a 16-membered ring macrolide (antibiotic). It was discovered in 1952 as a product of ''Streptomyces ambofaciens''. As a preparation for oral administration it has been used since 1955, in 1987 also the parenteral form was introduced into practice. The antibacterial 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 sp., 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. It is available for parenteral and oral administration
+=== 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 [[pyrimethamine]] and [[sulfadiazine]] (given with [[leucovorin]]).<ref name = "MayoClinic_Toxoplasmosis">{{cite web | url = http://www.mayoclinic.com/health/toxoplasmosis/DS00510/DSECTION=8 | title = Toxoplasmosis | work = MayoClinic.com }}</ref> Spiramycin
+== 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 | doi-broken-date = 2024-04-17 }}</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==
@@ Line 72: / Line 87: @@
 [[Category:Macrolide antibiotics]]
+[[Category:Secondary alcohols]]
+[[Category:Aldehydes]]
-{{Link GA|es}}
+[[Category:Dimethylamino compounds]]
-[[de:Spiramycin]]
+[[Category:Conjugated dienes]]
-[[dv:ސްޕައިރަމައިސިން]]
-[[es:Espiramicina]]
-[[fa:اسپیرامایسین]]
-[[fr:Spiramycine]]
-[[pl:Spiramycyna]]
-[[ru:Спирамицин]]