Spiramycin

Names

[ Name ]:
Spiramycin

[Synonym ]:
[(4R,5S,6S,7R,9R,10R,11E,13E,16R)-6-{[(2S,3R,4R,5S,6R)-5-{[(2S,4R,5S,6S)-4,5-Dihydroxy-4,6-dimethyltetrahydro-2H-pyran-2-yl]oxy}-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy}-10-{[(2R,5S,6S)-5-(dimethylamino)-6-methyltetrahydro-2H-pyran-2-yl]oxy}-4-hydroxy-5-methoxy-9,16-dimethyl-2-oxooxacyclohexadeca-11,13-dien-7-yl]acetaldehyde (non-preferred name)
Leucomycin
Foromacidin
Provamycin
[(4R,5S,6S,7R,9R,10R,11E,13E,16R)-6-{[(2S,3R,4R,5S,6R)-5-{[(2S,4R,5S,6S)-4,5-Dihydroxy-4,6-dimethyltetrahydro-2H-pyran-2-yl]oxy}-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy}-10-{[(2R,5S,6S)-5-(dimethylamino)-6-methyltetrahydro-2H-pyran-2-yl]oxy}-4-hydroxy-5-methoxy-9,16-dimethyl-2-oxooxacyclohexadeca-11,13-dien-7-yl]acetaldehyde
Spiramycin I
Rovamycin

Biological Activity

[Description]:

Spiramycin is a clinically important 16-member macrolide antibiotic produced by Streptomyces ambofaciens.

[Related Catalog]:

Signaling Pathways >> Anti-infection >> Bacterial

Research Areas >> Infection

[Target]

Bacterial[1]

[References]

[1]. Nguyen HC, et al. Post-PKS tailoring steps of the spiramycin macrolactone ring in Streptomyces ambofaciens. Antimicrob Agents Chemother. 2013 Aug;57(8):3836-42.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
913.7±65.0 °C at 760 mmHg

[ Molecular Formula ]:
C₄₃H₇₄N₂O₁₄

[ Molecular Weight ]:
843.053

[ Flash Point ]:
506.4±34.3 °C

[ Exact Mass ]:
842.513977

[ LogP ]:
3.06

[ Vapour Pressure ]:
0.0±0.6 mmHg at 25°C

[ Index of Refraction ]:
1.550

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
Xi

[ Risk Phrases ]:
36/37/38

[ Safety Phrases ]:
26-36-24/25

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
1

[ RTECS ]:
WG9400000

[ HS Code ]:
29419090

Articles

Regulation of the biosynthesis of the macrolide antibiotic spiramycin in Streptomyces ambofaciens.

J. Bacteriol. 192(21) , 5813-21, (2010)

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 srm...

A spicamycin derivative (KRN5500) provides neuropathic pain relief in patients with advanced cancer: a placebo-controlled, proof-of-concept trial.

J. Pain Symptom Manage. 43(4) , 679-93, (2012)

Neuropathic pain in patients with cancer can be difficult to treat effectively.The purpose of the study was to determine safety and efficacy of KRN5500, a novel, spicamycin-derived, nonopioid analgesi...

Influences of two antibiotic contaminants on the production, release and toxicity of microcystins

Ecotoxicol. Environ. Saf. 77 , 79-87, (2012)

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 s...

Related Compounds

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