Spiramycin Chemical Properties

Melting point:

126-128 °C

Boiling point:

914℃

alpha 

D20 -80° (methanol)

refractive index 

81 ° (C=2, 10% AcOH)

Flash point:

>110°(230°F)

storage temp. 

2-8°C

solubility 

ethanol: 50 mg/mL, clear to slightly hazy, light-yellow

form 

powder

color 

white to light yellow

optical activity

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

Water Solubility 

Soluble in methanol. Slightly soluble in water

Merck 

14,8752

CAS DataBase Reference

8025-81-8

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-24/25

WGK Germany 

1

RTECS 

WG9400000

F 

10

HS Code 

29419090

Hazardous Substances Data

8025-81-8(Hazardous Substances Data)

Toxicity

LD50 in rats (mg/kg): 9400 orally; 1000 s.c.; 170 i.v. (Sous)

MSDS

• Language:English Provider:SigmaAldrich

Spiramycin Usage And Synthesis

Description

Spiramycin was found in the culture broth of Streptomyces ambofaciens by Rhone Poulenc in 1954 and its acetate was synthesized by Kyowa Hakko Kogyo Co. in 1965. This antibiotic consists of three closely related macrolide components, I, II, and III, whose ratio is 2 : 1 : 1. Spiramycin shows almost the same antimicrobial spectrum and activity as the other macrolides, but its acetate, acetylspiramycin, has much better pharmacokinetic properties and activity in vivo.

Chemical Properties

An antibiotic substance.

Originator

Rovamycine,Specia,France,1972

Uses

antibacterial

Uses

vitamin A

Uses

Spiramycin I (foromacidin A) is the major analogue of a complex of 16-membered macrocyclic lactones produced by S. ambofaciens and S. spiramyceticus that have broad spectrum antibiotic activity. Spiramycins are unusual among the macrocyclic lactones in that they contain two basic sugars. Spiramycin complex has been used in both human and animal health but its use has not been widespread.

Manufacturing Process

The process for producing spiramycin comprises inoculating an aqueous nutrient medium with a culture of the NRRL No. 2420, allowing aerobic fermentation to take place and separating from the culture medium the spiramycin thus formed. The culture medium also contains the antibiotic substance known as Congocidin which, however, does not possess the same useful properties as spiramycin and which can be isolated in crystalline form. The separation of the two antibiotic substances is readily achieved.

brand name

Rovamycin (Rhone-Poulenc Rorer).

Therapeutic Function

Antibacterial

Antimicrobial activity

Enterobacteriaceae are resistant. Spiramycin is also active against anaerobic species: Actinomyces israelii (MIC 2–4 mg/L), Cl. perfringens (MIC 2–8 mg/L) and Bacteroides spp. (MIC 4–14 mg/L). It is also active against Tox. gondii.

Hazard

Poison; moderately toxic; teratogen; muta- gen; can cause hypermotility, diarrhea, nausea, or vomiting.

Pharmaceutical Applications

A fermentation product of Streptomyces ambofaciens, composed of several closely related compounds. Spiramycin 1 is the major component (c. 63%); spiramycins 2 and 3 are the acetate and monopropionate esters, respectively. It is available for oral administration and as spiramycin adipate for intravenous infusion. Spiramycins are relatively stable in acid conditions. A derivative, acetylspiramycin, is available in Japan.

Pharmacokinetics

Oral absorption: Variable
Cmax 1 g oral： 2.8 mg/L after 2 h
Plasma half-life：4–8h
Volume of distribution ：383 L
Plasma protein binding ：15%
In healthy volunteers given 2 g orally followed by 1 g every 6 h, peak plasma levels were 1.0–6.7 mg/L. After 1 g orally the AUC was 10.8 mg.h/L, with an apparent elimination halflife of 2.8 h. It is widely distributed in the tissues. It does not reach the CSF. Levels 12 h after a dose of 1 g were 0.25 mg/L in serum, 5.3 mg/L in bone and 6.9 mg/L in pus. Levels of 10.6 mg/L have been found 4 h after dosing in saliva, and concentrations at least equal to those in the serum are seen in bronchial secretions. A concentration of 27 mg/g was found in prostate tissues after repeated dosage. Only 5–15% is recovered from the urine. Most is metabolized, but significant quantities are eliminated via the bile, in which concentrations up to 40 times those in the serum may be found.

Side effects

Spiramycin is generally well tolerated, the most common adverse reactions being gastrointestinal disturbances, notably abdominal pain, nausea and vomiting, rashes and sensitization following contact.

Spiramycin(8025-81-8)Related Product Information

• SPIRAMYCIN BASE
• spiramycin ii,Spiramycin B (7CI, 8CI),Spiramycin II (6CI),spiramycin
• Alvespimycin
• SPIRAMYCIN EMBONATE
• Spiramycin, hexanedioate (1:1) (salt) ,SPIRAMYCIN ADIPATE,SPIRAMYCIN HEXANEDIOATE
• Spiramycin U
• SPIRAMYCIN III,Spiramycin C
• Spiramycin I-d3,Spiramycin A-d,Spiramycin A-d3
• SPIRAMYCIN I STANDARD,Spiramycin A,SPIRAMYCIN I
• Spiramycin
• Speramycin EP
• spiramycin I 3-hydroxyl acylase
• SPIRAMYCIN A MIXTURE OF SPIR
• Spiramycin/SpiramycinEmbonate/SpiramycinAdipate
• Spiramycin, 4,4'-methylenebis[3-hydroxy-2-naphthalenecarboxylate] (ester)