Synonym
Spiramycin Free Base; HSDB7027; HSDB-7027; HSDB 7027
IUPAC/Chemical Name
2-[(4R,5S,6S,7R,9R,10R,11E,13E,16R)-6-{[(2S,3R,4R,5S,6R)-5-{[(2S,5S,6S)-4,5-dihydroxy-4,6-dimethyloxan-2-yl]oxy}-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-10-{[(2R,5S,6R)-5-(dimethylamino)-6-methyloxan-2-yl]oxy}-4-hydroxy-5-methoxy-9,16-dimethyl-2-oxo-1-oxacyclohexadeca-11,13-dien-7-yl]acetaldehyde
InChi Key
ACTOXUHEUCPTEW-AQKFJFIXSA-N
InChi Code
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
SMILES Code
O=CC[C@@H]1[C@H](O[C@@H]2O[C@H](C)[C@@H](O[C@@H]3O[C@@H](C)[C@H](O)C(C)(O)C3)[C@H](N(C)C)[C@H]2O)[C@@H](OC)[C@H](O)CC(O[C@H](C)C/C=C/C=C/[C@H](O[C@@H]4O[C@H](C)[C@@H](N(C)C)CC4)[C@H](C)C1)=O
Purity
>90% (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
>2 years if stored properly
Drug Formulation
To be determined
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
Biological target:
Spiramycin is a macrolide antibiotic with activity against bacteria and Toxoplasma gondii activities. Spiramycin also has antiparasitic effects.
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
843.07
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.
| 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: Rubinstein E, Keller N. Spiramycin renaissance. J Antimicrob Chemother. 1998 Nov;42(5):572-6. doi: 10.1093/jac/42.5.572. PMID: 9848439.
2: Vacek V. Spiramycin [Spiramycin]. Cas Lek Cesk. 1994 Jan 17;133(2):56-60. Czech. PMID: 8131182.
3: Chen Z, Dou X, Zhang Y, Yang M, Wei D. Rapid thermal-acid hydrolysis of spiramycin by silicotungstic acid under microwave irradiation. Environ Pollut. 2019 Jun;249:36-44. doi: 10.1016/j.envpol.2019.02.074. Epub 2019 Feb 25. PMID: 30878860.
4: SPIRAMYCIN. Can Med Assoc J. 1958 May 1;78(9):713-4. PMID: 13523517; PMCID: PMC1829884.
5: SPIRAMYCIN. Br Med J. 1956 Mar 17;1(4967):621. PMID: 13293407.
6: Poveda-Montoyo I, Álvarez-Chinchilla PJ, García Del Pozo MC, Encabo B, Silvestre JF. Spiramycin-related cutaneous eruption confirmed by patch testing. Contact Dermatitis. 2018 Mar;78(3):233-234. doi: 10.1111/cod.12914. PMID: 29430709.
7: Brook I. Pharmacodynamics and pharmacokinetics of spiramycin and their clinical significance. Clin Pharmacokinet. 1998 Apr;34(4):303-10. doi: 10.2165/00003088-199834040-00003. PMID: 9571302.
8: Yang W, Ok YS, Dou X, Zhang Y, Yang M, Wei D, Xu P. Effectively remediating spiramycin from production wastewater through hydrolyzing its functional groups using solid superacid TiO2/SO4. Environ Res. 2019 Aug;175:393-401. doi: 10.1016/j.envres.2019.05.037. Epub 2019 May 25. PMID: 31154229.
9: 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.
10: Awad M, Tian Z, Gao Y, Yang M, Zhang Y. Pretreatment of spiramycin fermentation residue using hyperthermophilic digestion: quick startup and performance. Water Sci Technol. 2018 Dec;78(9):1823-1832. doi: 10.2166/wst.2018.256. PMID: 30566086.
