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MedKoo Cat#: 574034 | Name: Streptogramin B
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Description:

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

Streptogramin B is a macrolide antibiotic that inhibits the growth of Clostridium, Peptostreptococcus, and Propionibacterium bacterial species. Streptogramin B inhibits protein synthesis by interacting with the 50S ribosome. Resistance to streptogramin B is conferred by erythromycin ribosome methylation (erm) genes, which code for methylases that methylate the 50S ribosome, interfering with streptogramin B binding.

Chemical Structure

Streptogramin B
Streptogramin B
CAS#3131-03-1

Theoretical Analysis

MedKoo Cat#: 574034

Name: Streptogramin B

CAS#: 3131-03-1

Chemical Formula: C45H54N8O10

Exact Mass: 866.3963

Molecular Weight: 866.97

Elemental Analysis: C, 62.34; H, 6.28; N, 12.92; O, 18.45

Price and Availability

Size Price Availability Quantity
1mg USD 350.00 2 weeks
5mg USD 700.00 2 weeks
10mg USD 1,000.00 2 weeks
25mg USD 1,500.00 2 weeks
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Synonym
Streptogramin B, Mikamycin IA, Mikamycin B, Ostreogrycin B, Pristinamycin IA, Vernamycin Bα, Virginiamycin B​
IUPAC/Chemical Name
N-((6R,9S,10R,13S,15aS,22S,24aS)-22-(4-(dimethylamino)benzyl)-6-ethyl-10,23-dimethyl-5,8,12,15,17,21,24-heptaoxo-13-phenyldocosahydro-12H-pyrido[2,1-f]pyrrolo[2,1-l][1]oxa[4,7,10,13,16]pentaazacyclononadecin-9-yl)-3-hydroxypicolinamide
InChi Key
YGXCETJZBDTKRY-DZCVGBHJSA-N
InChi Code
InChI=1S/C45H54N8O10/c1-6-31-42(59)52-22-11-14-32(52)43(60)51(5)34(24-27-16-18-29(19-17-27)50(3)4)44(61)53-23-20-30(54)25-33(53)39(56)49-37(28-12-8-7-9-13-28)45(62)63-26(2)36(40(57)47-31)48-41(58)38-35(55)15-10-21-46-38/h7-10,12-13,15-19,21,26,31-34,36-37,55H,6,11,14,20,22-25H2,1-5H3,(H,47,57)(H,48,58)(H,49,56)/t26-,31-,32+,33+,34+,36+,37+/m1/s1
SMILES Code
O=C1C[C@](C(N[C@@H](C2=CC=CC=C2)C(O[C@H](C)[C@H](NC(C3=C(O)C=CC=N3)=O)C4=O)=O)=O)([H])N(C([C@@](CC5=CC=C(N(C)C)C=C5)([H])N(C)C([C@]6([H])CCCN6C([C@H](N4)CC)=O)=O)=O)CC1
Appearance
A crystalline solid
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
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Streptogramin B inhibits the growth of Clostridium, Peptostreptococcus, and Propionibacterium bacterial species (MIC90s = 2, 0.5, and 8 μg/ml, respectively). Streptogramin B inhibits protein synthesis by interacting with the 50S ribosome.
In vitro activity:
Streptogramin B is a macrolide antibiotic that inhibits protein synthesis by interacting with the 50S ribosome. Reference: Antimicrob Agents Chemother. 1999 Dec;43(12):2823-30. https://pubmed.ncbi.nlm.nih.gov/10582867/
In vivo activity:
Macrolide-lincosamide-streptogramin B (MLSB) resistance may spread within the gut microbiota of E. faecalis inoculated chickens under specific and non-specific pressure and even in the absence of any antimicrobial pressure. Depending on the particular antibiotic pressure, different bacterial species seem to be involved in the spread of MLSB resistance. PFGE analysis of MLSB-resistant enterococci revealed four clones, all differing from the challenge strain. All of the MLSB-resistant isolates harboured a plasmid of the same size as pAMβ1. Reference: Vet Microbiol. 2014 Jul 16;171(3-4):388-96. https://pubmed.ncbi.nlm.nih.gov/24467930/
Solvent mg/mL mM
Solubility
DMSO 33.3 38.44
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 866.97 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. Goudarzi M, Tayebi Z, Fazeli M, Miri M, Nasiri MJ. Molecular Characterization, Drug Resistance and Virulence Analysis of Constitutive and Inducible Clindamycin Resistance Staphylococcus aureus Strains Recovered from Clinical Samples, Tehran - Iran. Infect Drug Resist. 2020 Apr 22;13:1155-1162. doi: 10.2147/IDR.S251450. PMID: 32368106; PMCID: PMC7183778. 2. Roberts MC, Sutcliffe J, Courvalin P, Jensen LB, Rood J, Seppala H. Nomenclature for macrolide and macrolide-lincosamide-streptogramin B resistance determinants. Antimicrob Agents Chemother. 1999 Dec;43(12):2823-30. doi: 10.1128/AAC.43.12.2823. PMID: 10582867; PMCID: PMC89572. 3. Stainton SM, Abdelraouf K, Utley L, Pucci MJ, Lister T, Nicolau DP. Assessment of the In Vivo Activity of SPR741 in Combination with Azithromycin against Multidrug-Resistant Enterobacteriaceae Isolates in the Neutropenic Murine Thigh Infection Model. Antimicrob Agents Chemother. 2018 Jun 26;62(7):e00239-18. doi: 10.1128/AAC.00239-18. PMID: 29914941; PMCID: PMC6021673. 4. Marosevic D, Cervinkova D, Vlkova H, Videnska P, Babak V, Jaglic Z. In vivo spread of macrolide-lincosamide-streptogramin B (MLSB) resistance--a model study in chickens. Vet Microbiol. 2014 Jul 16;171(3-4):388-96. doi: 10.1016/j.vetmic.2013.12.017. Epub 2014 Jan 3. PMID: 24467930.
In vitro protocol:
1. Goudarzi M, Tayebi Z, Fazeli M, Miri M, Nasiri MJ. Molecular Characterization, Drug Resistance and Virulence Analysis of Constitutive and Inducible Clindamycin Resistance Staphylococcus aureus Strains Recovered from Clinical Samples, Tehran - Iran. Infect Drug Resist. 2020 Apr 22;13:1155-1162. doi: 10.2147/IDR.S251450. PMID: 32368106; PMCID: PMC7183778. 2. Roberts MC, Sutcliffe J, Courvalin P, Jensen LB, Rood J, Seppala H. Nomenclature for macrolide and macrolide-lincosamide-streptogramin B resistance determinants. Antimicrob Agents Chemother. 1999 Dec;43(12):2823-30. doi: 10.1128/AAC.43.12.2823. PMID: 10582867; PMCID: PMC89572.
In vivo protocol:
1. Stainton SM, Abdelraouf K, Utley L, Pucci MJ, Lister T, Nicolau DP. Assessment of the In Vivo Activity of SPR741 in Combination with Azithromycin against Multidrug-Resistant Enterobacteriaceae Isolates in the Neutropenic Murine Thigh Infection Model. Antimicrob Agents Chemother. 2018 Jun 26;62(7):e00239-18. doi: 10.1128/AAC.00239-18. PMID: 29914941; PMCID: PMC6021673. 2. Marosevic D, Cervinkova D, Vlkova H, Videnska P, Babak V, Jaglic Z. In vivo spread of macrolide-lincosamide-streptogramin B (MLSB) resistance--a model study in chickens. Vet Microbiol. 2014 Jul 16;171(3-4):388-96. doi: 10.1016/j.vetmic.2013.12.017. Epub 2014 Jan 3. PMID: 24467930.
1: Cinthi M, Coccitto SN, Simoni S, D'Achille G, Zeni G, Mazzariol A, Pocognoli A, Di Lodovico S, Di Giulio M, Morroni G, Mingoia M, Vignaroli C, Brenciani A, Giovanetti E. Molecular Characterization of Enterococcus faecium Clinical Isolates Harbouring erm (T) from an Italian Hospital. Curr Microbiol. 2024 Oct 29;81(12):431. doi: 10.1007/s00284-024-03968-3. PMID: 39472351. 2: Tercero-Guerrero D, Blanco JL, Hernández M, Torre-Fuentes L, Alvarez J, García ME. Whole-genome sequencing of toxigenic Clostridioides difficile reveals multidrug resistance and virulence genes in strains of environmental and animal origin. BMC Vet Res. 2024 Oct 21;20(1):479. doi: 10.1186/s12917-024-04332-0. PMID: 39434132; PMCID: PMC11492571. 3: Xie N, Ma T, Gao Y, Fu J, Tan C, Wang Z, Wang Z, Krüger-Haker H, Feßler AT, Wu C, Shen J, Schwarz S, Wang Y. Two novel plasmids harbouring the multiresistance gene cfr in porcine Staphylococcus equorum. J Glob Antimicrob Resist. 2024 Oct 1;39:170-174. doi: 10.1016/j.jgar.2024.09.004. Epub ahead of print. PMID: 39362467. 4: Liu Y, Zhang Q, Shi Y, Hao Z, Zhan X. Anthropogenic activities significantly interfered distribution and co-occurrence patterns of antibiotic resistance genes in a small rural watershed in Southwest China. Ecotoxicol Environ Saf. 2024 Oct 15;285:117118. doi: 10.1016/j.ecoenv.2024.117118. Epub 2024 Oct 1. PMID: 39357373. 5: Firouzjaei MD, Halaji M, Yaghoubi S, Hendizadeh P, Salehi M, Mohammadi M, Pournajaf A. Inducible clindamycin-resistant and biofilm formation in the Staphylococcus aureus isolated from healthcare worker's anterior nasal carriage. BMC Res Notes. 2024 Sep 9;17(1):252. doi: 10.1186/s13104-024-06926-1. PMID: 39252055; PMCID: PMC11384700. 6: Smith AM, Ramudzulu M, Munk P, Avot BJP, Esterhuyse KCM, van Blerk N, Kwenda S, Sekwadi P. Metagenomics analysis of sewage for surveillance of antimicrobial resistance in South Africa. PLoS One. 2024 Aug 26;19(8):e0309409. doi: 10.1371/journal.pone.0309409. PMID: 39186711; PMCID: PMC11346938. 7: Aljohani A, Clarke D, Byrne M, Fleming G. The bacterial microbiome and resistome of house dust mites in Irish homes. Sci Rep. 2024 Aug 23;14(1):19621. doi: 10.1038/s41598-024-70686-y. PMID: 39179632; PMCID: PMC11343766. 8: Bujňáková D, Karahutová L. Molecular characteristics and antibiotic resistance of Staphylococcus aureus and Staphylococcus haemolyticus isolated from bovine mastitis. Res Vet Sci. 2024 Sep;177:105365. doi: 10.1016/j.rvsc.2024.105365. Epub 2024 Jul 22. PMID: 39053094. 9: Ma CX, Li Y, Liu WT, Li Y, Zhao F, Lian XT, Ding J, Liu SM, Liu XP, Fan BZ, Liu LY, Xue F, Li J, Zhang JR, Xue Z, Pei XT, Lin JZ, Liang JH. Synthetic macrolides overcoming MLSBK-resistant pathogens. Cell Discov. 2024 Jul 11;10(1):75. doi: 10.1038/s41421-024-00702-y. PMID: 38992047; PMCID: PMC11239830. 10: Hamdy A, Marciniak T, Alseqely M, Ziebuhr W, Abouelmagd E, Abouelfetouh A. Phenotypic and genotypic characterization of commensal staphylococci isolated from young volunteers in Alexandria, Egypt. Sci Rep. 2024 Jun 27;14(1):14850. doi: 10.1038/s41598-024-60924-8. PMID: 38937465; PMCID: PMC11211488. 11: Cachetas D, Vaz-Moreira I, Pereira V, Manaia CM. Towards the definition of an antibiotic resistome signature in wastewater and downstream environments. Environ Pollut. 2024 Sep 15;357:124424. doi: 10.1016/j.envpol.2024.124424. Epub 2024 Jun 21. PMID: 38909773. 12: K S, Karabasanavar N, C B, G K S, P S G, Waghe P, A M K, Fairoze MN. Milk supply chain as a reservoir of antimicrobial-resistant Staphylococcus species. J Biosci. 2024;49:60. PMID: 38817159. 13: Zalewska M, Błażejewska A, Szadziul M, Ciuchciński K, Popowska M. Effect of composting and storage on the microbiome and resistome of cattle manure from a commercial dairy farm in Poland. Environ Sci Pollut Res Int. 2024 May;31(21):30819-30835. doi: 10.1007/s11356-024-33276-z. Epub 2024 Apr 15. PMID: 38616224; PMCID: PMC11096248. 14: Watson E, Hamilton S, Silva N, Moss S, Watkins C, Baily J, Forster T, Hall AJ, Dagleish MP. Variations in antimicrobial resistance genes present in the rectal faeces of seals in Scottish and Liverpool Bay coastal waters. Environ Pollut. 2024 May 15;349:123936. doi: 10.1016/j.envpol.2024.123936. Epub 2024 Apr 6. PMID: 38588972. 15: Daw Elbait G, Daou M, Abuoudah M, Elmekawy A, Hasan SW, Everett DB, Alsafar H, Henschel A, Yousef AF. Comparison of qPCR and metagenomic sequencing methods for quantifying antibiotic resistance genes in wastewater. PLoS One. 2024 Apr 5;19(4):e0298325. doi: 10.1371/journal.pone.0298325. PMID: 38578803; PMCID: PMC10997137. 16: Haley BJ, Kim SW, Van Kessel JA. Escherichia coli Isolated from Bovine Sources Encoding the Fosfomycin Resistance Gene fosA7.5. Foodborne Pathog Dis. 2024 Mar 27. doi: 10.1089/fpd.2023.0132. Epub ahead of print. PMID: 38536098. 17: Yao T, Ye L, Wang S, Lu J, Li H, Yu G. Effects of cadmium exposure on gut microbiota and antibiotic resistance genes in Haliotis diversicolor abalone. Chemosphere. 2024 Mar;352:141507. doi: 10.1016/j.chemosphere.2024.141507. Epub 2024 Feb 20. PMID: 38387663. 18: Kositanont U, Changkaew K, Phatcharaharikarn M, Songngamsuk T, Changkwanyeun R, Yasawong M. Draft genome sequence data of the multidrug-resistant bacterium Staphylococcus haemolyticus 010503B isolated from an aerosol sample in a hospital waiting area in Thailand. Data Brief. 2024 Feb 6;53:110154. doi: 10.1016/j.dib.2024.110154. PMID: 38375149; PMCID: PMC10875221. 19: Shields KE, Ranava D, Tan Y, Zhang D, Yap MF. Epitranscriptional m6A modification of rRNA negatively impacts translation and host colonization in Staphylococcus aureus. PLoS Pathog. 2024 Jan 22;20(1):e1011968. doi: 10.1371/journal.ppat.1011968. PMID: 38252661; PMCID: PMC10833563. 20: El-Banna TE, Sonbol FI, Kamer AMA, Badr SAMM. Genetic diversity of macrolides resistant Staphylococcus aureus clinical isolates and the potential synergistic effect of vitamins, C and K3. BMC Microbiol. 2024 Jan 20;24(1):30. doi: 10.1186/s12866-023-03169-1. PMID: 38245680; PMCID: PMC10799532.