Spiramycin

Spiramycin
Clinical data
Routes of
administration		oral
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Identifiers
  • (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
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
NIAID ChemDB
E numberE710 (antibiotics) Edit this at Wikidata
CompTox Dashboard (EPA)
ECHA InfoCard100.029.476 Edit this at Wikidata
Chemical and physical data
FormulaC43H74N2O14
Molar mass843.065 g·mol−1
3D model (JSmol)
Melting point134 to 137 °C (273 to 279 °F)
Solubility in waterInsoluble in water; Very soluble in acetonitrile and methanol; Almost completely(>99.5) in ethanol. mg/mL (20 °C)
  • 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=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+ checkY
  • Key:ACTOXUHEUCPTEW-OBURPCBNSA-N checkY
 ☒NcheckY (what is this?)  (verify)

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]

  1. ^ "Spiramycin advanced consumer information". Drugs.com.
  2. ^ Cite error: The named reference MayoClinic_Toxoplasmosis was invoked but never defined (see the help page).
  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.