Neospiramycin

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

MedKoo CAT#: 598656

CAS#: 4617-99-6

Description: Neospiramycin is a major metabolite of Spiramycin I.

Chemical Structure

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Neospiramycin
CAS# 4617-99-6
Instruction

Theoretical Analysis

MedKoo Cat#: 598656
Name: Neospiramycin
CAS#: 4617-99-6
Chemical Formula: C39H66N2O12
Exact Mass: 754.46
Molecular Weight: 754.950
Elemental Analysis: C, 62.05; H, 8.81; N, 3.71; O, 25.43

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

Synonym: Neospiramycin;

IUPAC/Chemical Name: (4R,5S,6S,7R,9R,10R,11E,13Z,16S)-6-(((2S,3R,4R,5S,6S)-4-(dimethylamino)-3,5-dihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-10-(((2S,5S,6S)-5-(dimethylamino)-6-methyltetrahydro-2H-pyran-2-yl)oxy)-5-methoxy-9,16-dimethyl-2-oxo-7-(2-oxoethyl)oxacyclohexadeca-11,13-dien-4-yl propionate

InChi Key: BRCNXLAKVWKNPR-ZFZFMVAKSA-N

InChi Code: InChI=1S/C39H66N2O12/c1-11-31(43)51-30-22-32(44)48-24(3)15-13-12-14-16-29(52-33-18-17-28(40(6)7)25(4)49-33)23(2)21-27(19-20-42)37(38(30)47-10)53-39-36(46)34(41(8)9)35(45)26(5)50-39/h12-14,16,20,23-30,33-39,45-46H,11,15,17-19,21-22H2,1-10H3/b13-12-,16-14+/t23-,24+,25+,26+,27+,28+,29+,30-,33-,34-,35-,36-,37+,38+,39+/m1/s1

SMILES Code: CN([C@@H]1[C@H](O)[C@H](C)O[C@H]([C@@H]1O)O[C@@H]2[C@H]([C@H](OC(CC)=O)CC(O[C@H](C/C=C\C=C\[C@H](O[C@@H]3CC[C@H](N(C)C)[C@H](C)O3)[C@H](C)C[C@@H]2CC=O)C)=O)OC)C

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: Soluble in DMSO

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: 2934.99.03.00

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 754.95 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:
In vitro protocol:
In vivo protocol:

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1: Renard L, Henry P, Sanders P, Laurentie M, Delmas JM. Determination of spiramycin and neospiramycin in plasma and milk of lactating cows by reversed-phase high-performance liquid chromatography. J Chromatogr B Biomed Appl. 1994 Jul 1;657(1):219-26. PubMed PMID: 7952072.

2: Gratzl R, Sodeck G, Platzer P, Jäger W, Graf J, Pollak A, Thalhammer T. Treatment of toxoplasmosis in pregnancy: concentrations of spiramycin and neospiramycin in maternal serum and amniotic fluid. Eur J Clin Microbiol Infect Dis. 2002 Jan;21(1):12-6. PubMed PMID: 11913495.

3: Wang J, Leung D. Determination of spiramycin and neospiramycin antibiotic residues in raw milk using LC/ESI-MS/MS and solid-phase extraction. J Sep Sci. 2009 Feb;32(4):681-8. doi: 10.1002/jssc.200800599. PubMed PMID: 19165836.

4: Sano H, Inoue M, Yamashita K, Okachi R, Omura S. Chemical modification of spiramycins. I. Synthesis of the acetal derivatives of neospiramycin I. J Antibiot (Tokyo). 1983 Oct;36(10):1336-44. PubMed PMID: 6643282.

5: Sano H, Inoue M, Omura S. Chemical modification of spiramycins. II. Synthesis and antimicrobial activity of 4'-deoxy derivatives of neospiramycin I and their 12-(Z)-isomers. J Antibiot (Tokyo). 1984 Jul;37(7):738-49. PubMed PMID: 6469868.

6: Juhel-Gaugain M, Anger B, Laurentie M. Multiresidue chromatographic method for the determination of macrolide residues in muscle by high-performance liquid chromatography with UV detection. J AOAC Int. 1999 Sep-Oct;82(5):1046-53. PubMed PMID: 10513006.

7: Sanders P, Guillot P, Dagorn M, Moulin G, Delépine B, Mourot D. Pharmacokinetics and tissue residues of spiramycin in cattle after intramuscular administration of multiple doses. Am J Vet Res. 1994 Mar;55(3):358-62. PubMed PMID: 8192258.

8: Omura S, Sano H, Sunazuka T. Structure activity relationships of spiramycins. J Antimicrob Chemother. 1985 Jul;16 Suppl A:1-11. PubMed PMID: 3902764.

9: Zhang H, Zhang Y, Yang M, Liu M. Evaluation of residual antibacterial potency in antibiotic production wastewater using a real-time quantitative method. Environ Sci Process Impacts. 2015 Nov;17(11):1923-9. doi: 10.1039/c5em00228a. PubMed PMID: 26395288.

10: Poras H, Kunesch G, Barrière JC, Berthaud N, Andremont A. Synthesis and in vitro antibacterial activity of catechol-spiramycin conjugates. J Antibiot (Tokyo). 1998 Aug;51(8):786-94. PubMed PMID: 9766470.

11: Dickson LC. Performance characterization of a quantitative liquid chromatography-tandem mass spectrometric method for 12 macrolide and lincosamide antibiotics in salmon, shrimp and tilapia. J Chromatogr B Analyt Technol Biomed Life Sci. 2014 Sep 15;967:203-10. doi: 10.1016/j.jchromb.2014.07.031. Epub 2014 Jul 27. PubMed PMID: 25125397.

12: Kitao C, Ikeda H, Hamada H, Omura S. Bioconversion and biosynthesis of 16-membered macrolide antibiotics. XIII. Regulation of spiramycin I 3-hydroxyl acylase formation by glucose, butyrate, and cerulenin. J Antibiot (Tokyo). 1979 Jun;32(6):593-9. PubMed PMID: 468735.

13: Dickson LC, O'Byrne C, Chan W. A quantitative method for residues of macrolide antibiotics in porcine kidney by liquid chromatography/tandem mass spectrometry. J AOAC Int. 2012 Mar-Apr;95(2):567-75. PubMed PMID: 22649946.

14: Sanders P, Delépine B. Confirmatory analysis for spiramycin residue in bovine muscle by liquid chromatography/particle beam mass spectrometry. Biol Mass Spectrom. 1994 Jun;23(6):369-75. PubMed PMID: 8038231.

15: Li SY, Nelson DS. Acetylspiramycin and the immune system. I. Effects of acetylspiramycin on phagocytosis by mouse macrophages in vitro and in vivo. Int J Immunopharmacol. 1985;7(6):881-8. PubMed PMID: 4077347.

16: Maher HM, Youssef RM, Khalil RH, El-Bahr SM. Simultaneous multiresidue determination of metronidazole and spiramycin in fish muscle using high performance liquid chromatography with UV detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2008 Dec 15;876(2):175-81. doi: 10.1016/j.jchromb.2008.10.033. Epub 2008 Nov 1. PubMed PMID: 19013111.

17: Horie M, Takegami H, Toya K, Kikuchi Y, Nakazawa H. [Determination of spiramycin and tilmicosin in meat and fish by LC/MS]. Shokuhin Eiseigaku Zasshi. 2003 Jun;44(3):150-4. Japanese. PubMed PMID: 12968469.

18: Liu L, Roets E, Busson R, Vankeerberghen A, Janssen G, Hoogmartens J. Two novel spiramycins obtained from commercial samples: isolation and elucidation of structure. J Antibiot (Tokyo). 1996 Apr;49(4):398-401. PubMed PMID: 8642006.