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S9132

Sigma-Aldrich

Spiramycin

Synonym(s):

Rovamycin, Formacidine

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About This Item

CAS Number:
8025-81-8
EC Number:
232-429-6
MDL number:
MFCD01314545
UNSPSC Code:
51283208
PubChem Substance ID:
24899826
NACRES:
NA.85

form

powder

optical activity

[α]/D -85 to -80° in water (Specific rotation (dry basis))

potency

≥4100 I.U. per mg (dry basis)

storage condition

(Keep container tightly closed in a dry and well-ventilated place.)

color

white to light yellow

solubility

methanol: soluble

cation traces

heavy metals: ≤20 ppm

antibiotic activity spectrum

Gram-positive bacteria

Mode of action

protein synthesis | interferes

storage temp.

2-8°C

SMILES string

CO[C@H]1[C@H](O)CC(=O)O[C@H](C)C\C=C\C=C\[C@H](OC2CCC(C(C)O2)N(C)C)[C@H](C)C[C@H](CC=O)[C@@H]1OC3OC(C)C(OC4CC(C)(O)C(O)C(C)O4)C(C3O)N(C)C

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+/t24-,25-,26?,27?,28?,29+,30?,31-,32+,34?,35?,36?,37?,38?,39+,40+,41?,42?,43?/m1/s1

InChI key

ACTOXUHEUCPTEW-JMRHEKERSA-N

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General description

Chemical structure: macrolide

Application

Spiramycin is a macrolide antibiotic that is commonly used to treat infections of soft tissues. It has been used to treat bronchopulmonary infections in adults and has been used to study septicemia in mice .

Biochem/physiol Actions

Spiramycin is a 16-membered ring macrolide antibiotic from Streptomyces ambofaciens. It inhibits bacterial protein synthesis at the level of peptidy-tRNA dissociation from ribosomes. It is mainly used against Gram-positive bacteria.

Quality

A mixture of Spiramycin I, II and III.

Other Notes

Keep container tightly closed in a dry and well-ventilated place.

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Acute bronchopulmonary infections: treatment with i.v. spiramycin.
F Vachon and S Kernbaum
Chemotherapia, 6, 282-285 (1987)
O Rolin et al.
Pathologie-biologie, 34(5), 476-478 (1986-05-01)
Experimental septicemia was induced in mice by intraperitoneal injection of 10 to 100 lethal doses of Staphylococcus aureus and Streptococcus pneumoniae. Animals were treated by a mixture of adipic acid and spiramycin (subcutaneous route) or by spiramycin base (oral route)
Ying Liu et al.
Ecotoxicology and environmental safety, 77, 79-87 (2011-11-15)
The influences of spiramycin and amoxicillin on the algal growth, production and release of target microcystins (MCs), MC-LR, MC-RR and MC-YR, in Microcystis aeruginosa were investigated through the seven-day exposure test. Spiramycin were more toxic to M. aeruginosa than amoxicillin
Fatma Karray et al.
Journal of bacteriology, 192(21), 5813-5821 (2010-09-08)
Streptomyces ambofaciens synthesizes the macrolide antibiotic spiramycin. The biosynthetic gene cluster for spiramycin has been characterized for S. ambofaciens. In addition to the regulatory gene srmR (srm22), previously identified (M. Geistlich et al., Mol. Microbiol. 6:2019-2029, 1992), three putative regulatory
Thomas E Rams et al.
Anaerobe, 17(4), 201-205 (2011-04-29)
The occurrence of in vitro resistance to therapeutic concentrations of spiramycin, amoxicillin, and metronidazole was determined for putative periodontal pathogens isolated in the United States. Subgingival plaque specimens from 37 consecutive adults with untreated severe periodontitis were anaerobically cultured, and
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