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MedKoo Cat#: 574490 | Name: Spiramycin adipate
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Spiramycin adipate is an antibiotic that is used to study multidrug resistance of Strenotrophomonas maltophilia.

Chemical Structure

Spiramycin adipate
Spiramycin adipate
CAS#68880-55-7 (adipate)

Theoretical Analysis

MedKoo Cat#: 574490

Name: Spiramycin adipate

CAS#: 68880-55-7 (adipate)

Chemical Formula: C49H84N2O18

Exact Mass: 0.0000

Molecular Weight: 989.21

Elemental Analysis: C, 59.50; H, 8.56; N, 2.83; O, 29.11

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Related CAS #
8025-81-8 (free base) 24916-52-7 (III) 67724-08-7 (Embonate) 68880-55-7 (adipate)
Synonym
Spiramycin adipate; Spiramycin, Hexanedioate (salt); Suanovil
IUPAC/Chemical Name
2-((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-(((5S,6R)-5-(dimethylamino)-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4-hydroxy-5-methoxy-9,16-dimethyl-2-oxooxacyclohexadeca-11,13-dien-7-yl)acetaldehyde adipate
InChi Key
PLQDGTZICFBBSO-DPUAUXBSSA-N
InChi Code
InChI=1S/C43H74N2O14.C6H10O4/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;7-5(8)3-1-2-4-6(9)10/h12-14,16,20,24-32,34-42,47,49-51H,15,17-19,21-23H2,1-11H3;1-4H2,(H,7,8)(H,9,10)/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
SMILES Code
CO[C@H]1[C@@H](CC(O[C@@H](C/C=C/C=C/[C@@H]([C@@H](C[C@@H]([C@@H]1O[C@@H]2O[C@@H]([C@H]([C@H](N(C)C)[C@H]2O)O[C@H]3C[C@@](O)([C@H]([C@@H](O3)C)O)C)C)CC=O)C)OC4CC[C@H](N(C)C)[C@H](O4)C)C)=O)O.OC(CCCCC(O)=O)=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
To be determined
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Spiramycin adipate is effective against gram-positive aerobic pathogens, N. gonorrhoeae, and staphylococci.
In vitro activity:
Spiramycin has potential to be repurposed as a topical anti-inflammatory treatment. In lipopolysaccharide (LPS)-stimulated RAW 264.7 cells, spiramycin reduced levels of inflammatory markers like nitric oxide, IL-1β, and IL-6. It also inhibited the expression of NO synthase and blocked key signaling pathways involved in inflammation. Reference: Molecules. 2022 May 17;27(10):3202. https://pubmed.ncbi.nlm.nih.gov/35630676/
In vivo activity:
Spiramycin has potential in anti-obesity treatment. Spiramycin effectively attenuated high fat diet (HFD)-induced obesity and hepatic steatosis by inhibiting adipogenesis in obese mice. HFD-induced obese mice administered spiramycin had substantial decreases in body weight gain, serum leptin levels, adipose tissue mass, and hepatic lipid accumulation. The decreased levels of GPT and GOT in mice serum indicated that spiramycin attenuated hepatic injury caused by HFD. Reference: PLoS One. 2016 Jul 11;11(7):e0158632. https://pubmed.ncbi.nlm.nih.gov/27398599/

Preparing Stock Solutions

The following data is based on the product molecular weight 989.21 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Yagiz Aghayarov O, Bayar Muluk N, Vejselova Sezer C, Kutlu HM, Cingi C. Evaluation of spiramycin for topical applications: a cell culture study. Eur Rev Med Pharmacol Sci. 2023 Mar;27(2 Suppl):44-50. doi: 10.26355/eurrev_202303_31701. PMID: 36971220. 2. Kang JK, Kang HK, Hyun CG. Anti-Inflammatory Effects of Spiramycin in LPS-Activated RAW 264.7 Macrophages. Molecules. 2022 May 17;27(10):3202. doi: 10.3390/molecules27103202. PMID: 35630676; PMCID: PMC9143090. 3. Kim MO, Ryu HW, Choi JH, Son TH, Oh SR, Lee HS, Yuk HJ, Cho S, Kang JS, Lee CW, Lee J, Lee CK, Hong ST, Lee SU. Anti-Obesity Effects of Spiramycin In Vitro and In Vivo. PLoS One. 2016 Jul 11;11(7):e0158632. doi: 10.1371/journal.pone.0158632. PMID: 27398599; PMCID: PMC4939947. 4. Chew WK, Segarra I, Ambu S, Mak JW. Significant reduction of brain cysts caused by Toxoplasma gondii after treatment with spiramycin coadministered with metronidazole in a mouse model of chronic toxoplasmosis. Antimicrob Agents Chemother. 2012 Apr;56(4):1762-8. doi: 10.1128/AAC.05183-11. Epub 2012 Jan 23. PMID: 22271863; PMCID: PMC3318357.
In vitro protocol:
1. Yagiz Aghayarov O, Bayar Muluk N, Vejselova Sezer C, Kutlu HM, Cingi C. Evaluation of spiramycin for topical applications: a cell culture study. Eur Rev Med Pharmacol Sci. 2023 Mar;27(2 Suppl):44-50. doi: 10.26355/eurrev_202303_31701. PMID: 36971220. 2. Kang JK, Kang HK, Hyun CG. Anti-Inflammatory Effects of Spiramycin in LPS-Activated RAW 264.7 Macrophages. Molecules. 2022 May 17;27(10):3202. doi: 10.3390/molecules27103202. PMID: 35630676; PMCID: PMC9143090.
In vivo protocol:
1. Kim MO, Ryu HW, Choi JH, Son TH, Oh SR, Lee HS, Yuk HJ, Cho S, Kang JS, Lee CW, Lee J, Lee CK, Hong ST, Lee SU. Anti-Obesity Effects of Spiramycin In Vitro and In Vivo. PLoS One. 2016 Jul 11;11(7):e0158632. doi: 10.1371/journal.pone.0158632. PMID: 27398599; PMCID: PMC4939947. 2. Chew WK, Segarra I, Ambu S, Mak JW. Significant reduction of brain cysts caused by Toxoplasma gondii after treatment with spiramycin coadministered with metronidazole in a mouse model of chronic toxoplasmosis. Antimicrob Agents Chemother. 2012 Apr;56(4):1762-8. doi: 10.1128/AAC.05183-11. Epub 2012 Jan 23. PMID: 22271863; PMCID: PMC3318357.
1: Noureldin HAM, Abdel-Aziz AM, Mabrouk MM, Saad AHK, Badr IHA. Green and cost- effective voltammetric assay for spiramycin based on activated glassy carbon electrode and its applications to urine and milk samples. RSC Adv. 2023 Jan 3;13(2):844-852. doi: 10.1039/d2ra06768d. PMID: 36686907; PMCID: PMC9809205. 2: Bengtsson B, Franklin A, Jacobsson S, Luthman J, Horn af Rantzien M. Distribution of penicillin-G and spiramycin to tissue cages and subcutaneous tissue fluid in calves. Res Vet Sci. 1991 May;50(3):301-7. doi: 10.1016/0034-5288(91)90128-b. PMID: 1882137. 3: Dournon E, Rajagopalan P. Comparison of spiramycin and erythromycin in the treatment of experimental guinea pig legionellosis. J Antimicrob Chemother. 1988 Jul;22 Suppl B:69-72. doi: 10.1093/jac/22.supplement_b.69. PMID: 3182448. 4: Vachon F, Kernbaum S. Acute bronchopulmonary infections: treatment with i.v. spiramycin. Chemioterapia. 1987 Aug;6(4):282-5. PMID: 3308147. 5: Rolin O, Bouveret E, Bouanchaud DH. Activité curative de l'adipate de spiramycine utilisé par voie parentérale dans la septicémie expérimentale de la souris. Comparaison avec la spiramycine base administrée par voie orale [Curative activity of spiramycin adipate by parenteral route in experimental septicemia in mice. Comparison with orally administered basic spiramycin]. Pathol Biol (Paris). 1986 May;34(5):476-8. French. PMID: 3534725. 6: Franklin A, Horn af Rantzien M, Obel N, Ostensson K, Aström G. Concentrations of penicillin, streptomycin, and spiramycin in bovine udder tissue liquids. Am J Vet Res. 1986 Apr;47(4):804-7. PMID: 3963581. 7: Mashimo PA, Yamamoto Y, Slots J, Evans RT, Genco RJ. In vitro evaluation of antibiotics in the treatment of periodontal disease. Pharmacol Ther Dent. 1981;6(1-2):45-56. PMID: 6941319. 8: Kishima M, Hashimoto K. In vitro sensitivities to antimicrobial drugs of ureaplasmas isolated from the bovine respiratory tract, genital tract and eye. Res Vet Sci. 1979 Sep;27(2):218-22. PMID: 523809. 9: Kishima M, Hashimoto K, Minato H. Sensitivites in vitro to antimicrobial drugs of bovine mycoplasmas isolated from respiratory and genital tracts. Natl Inst Anim Health Q (Tokyo). 1978 Spring;18(1):18-26. PMID: 652043. 10: BOYD EM, PRICE-JONES MA. The comparative acute oral toxicity of spiramycin adipate in mice, rats, guinea pigs, and rabbits. Antibiot Chemother (Northfield). 1960 May;10:273-84. PMID: 13803536. 11: BOYD EM, PRICE-JONES MA. The acute subcutaneous toxicity of spiramycin adipate in cats. Antibiot Chemother (Northfield). 1959 Jun;9(6):353-7. PMID: 24545267. 12: BOYD EM. The chronic subcutaneous toxicity of spiramycin adipate. Can Med Assoc J. 1958 May 1;78(9):671-4. PMID: 13523506; PMCID: PMC1829879. 13: BOYD EM. The acute subcutaneous toxicity of spiramycin adipate in albino rats. Antibiot Annu. 1957-1958;5:842-51. PMID: 13521902.