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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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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)
Acute bronchopulmonary infections: treatment with i.v. spiramycin.
F Vachon and S Kernbaum
Chemotherapia, 6, 282-285 (1987)
Ying Liu et al.
Ecotoxicology and environmental safety, 86, 23-30 (2012-09-29)
Cyanobacteria may interact with antibiotic contaminants in aquatic environments, but the interaction effects and mechanisms remain unclear. In the present study, aqueous culture of Microcystis aeruginosa was exposed to 50ng/l-1μg/l of spiramycin and amoxicillin for seven days. The influences of
Wai Kit Chew et al.
Antimicrobial agents and chemotherapy, 56(4), 1762-1768 (2012-01-25)
Toxoplasma gondii is a parasite that generates latent cysts in the brain; reactivation of these cysts may lead to fatal toxoplasmic encephalitis, for which treatment remains unsuccessful. We assessed spiramycin pharmacokinetics coadministered with metronidazole, the eradication of brain cysts and
G Gasparini et al.
International journal of immunopathology and pharmacology, 23(2), 619-626 (2010-07-22)
Bisphosphonate-related osteonecrosis of the jaw (BRONJ) consists of an exposure of the jaw bone that persists for over 8 weeks in patients with positive history for bisphosphonates. Symptomatology is characterized by dull and ceaseless pain, and in advanced stages, the
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