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MedKoo Cat#: 329853 | Name: Pristinamycin
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Description:

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

Pristinamycin, also known as Virginiamycin antibiotic complex; NSC-246121; Antibiotic 899; Founderguard, is an antibiotic used primarily in the treatment of staphylococcal infections, and to a lesser extent streptococcal infections. Pristinamycin is a mixture of two components that have a synergistic antibacterial action. Pristinamycin IA is a macrolide, and results in pristinamycin's having a similar spectrum of action to erythromycin. Virginiamycin complex contains two streptogramin antibiotics, virginiamycin M1 (75%) and virginiamycin S1 (25%).

Chemical Structure

Pristinamycin
CAS#11006-76-1

Theoretical Analysis

MedKoo Cat#: 329853

Name: Pristinamycin

CAS#: 11006-76-1

Chemical Formula: C71H84N10O17

Exact Mass: 0.0000

Molecular Weight: 1349.51

Elemental Analysis: C, 63.19; H, 6.27; N, 10.38; O, 20.15

Price and Availability

Size Price Availability Quantity
5mg USD 625.00
10mg USD 950.00
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Related CAS #
11006-76-1 21411-53-0 23152-29-6
Synonym
Pristinamycin; Virginiamycin antibiotic complex; NSC-246121; Antibiotic 899; Founderguard; Mikamycin; RP 7293; Stapyocine; Streptogramin;
IUPAC/Chemical Name
N-((6R,9S,10R,13S,15aS,22S,24aS)-22-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 compound with (12Z,6R,7R,8E,13Z,15E,17S)-17-hydroxy-6-isopropyl-7,15-dimethyl-32,33-dihydro-31H-5-oxa-11-aza-1(4,2)-oxazola-3(1,5)-pyrrolacycloicosaphane-8,13,15-triene-2,4,10,19-tetraone (1:1)
InChi Key
MVTQIFVKRXBCHS-YWAQVZITSA-N
InChi Code
InChI=1S/C43H49N7O10.C28H35N3O7/c1-4-29-40(56)49-21-12-17-30(49)41(57)48(3)32(23-26-13-7-5-8-14-26)42(58)50-22-19-28(51)24-31(50)37(53)47-35(27-15-9-6-10-16-27)43(59)60-25(2)34(38(54)45-29)46-39(55)36-33(52)18-11-20-44-36;1-17(2)26-19(4)9-10-24(34)29-11-5-7-18(3)13-20(32)14-21(33)15-25-30-22(16-37-25)27(35)31-12-6-8-23(31)28(36)38-26/h5-11,13-16,18,20,25,29-32,34-35,52H,4,12,17,19,21-24H2,1-3H3,(H,45,54)(H,46,55)(H,47,53);5,7-10,13,16-17,19-20,26,32H,6,11-12,14-15H2,1-4H3,(H,29,34)/b;7-5-,10-9+,18-13+/t25-,29-,30+,31+,32+,34+,35+;19-,20-,26-/m11/s1
SMILES Code
O=C1CCN([C@@]([H])(C1)C(N[C@H](C(O[C@@H]([C@@H](C(N[C@@H](C(N2CCC3)=O)CC)=O)NC(C4=NC=CC=C4O)=O)C)=O)C5=CC=CC=C5)=O)C([C@H](CC6=CC=CC=C6)N(C([C@@]23[H])=O)C)=O.O=C(NC/C=C\C(C)=C\[C@H](C7)O)/C=C/[C@H]([C@H](OC(C8=CCCN8C(C9=COC(CC7=O)=N9)=O)=O)C(C)C)C
Appearance
Solid powder
Purity
>95% (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
>2 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:
Pristinamycin, also known as Virginiamycin antibiotic complex; NSC-246121; Antibiotic 899; Founderguard, is an antibiotic used primarily in the treatment of staphylococcal infections, and to a lesser extent streptococcal infections.
In vitro activity:
TBD
In vivo activity:
TBD

Preparing Stock Solutions

The following data is based on the product molecular weight 1,349.51 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:
TBD
In vitro protocol:
TBD
In vivo protocol:
TBD
1: Mast Y, Guezguez J, Handel F, Schinko E. A Complex Signaling Cascade Governs Pristinamycin Biosynthesis in Streptomyces pristinaespiralis. Appl Environ Microbiol. 2015 Oct;81(19):6621-36. doi: 10.1128/AEM.00728-15. Epub 2015 Jul 17. PubMed PMID: 26187956; PubMed Central PMCID: PMC4561715. 2: Cooper EC, Curtis N, Cranswick N, Gwee A. Pristinamycin: old drug, new tricks? J Antimicrob Chemother. 2014 Sep;69(9):2319-25. doi: 10.1093/jac/dku167. Epub 2014 Jun 2. Review. PubMed PMID: 24891428. 3: Tian J, Yang J, Li L, Ruan L, Wei W, Zheng G, Zhao W, Chen J, Jiang W, Ge M, Lu Y. The complete genome sequence of a high pristinamycin-producing strain Streptomyces pristinaespiralis HCCB10218. J Biotechnol. 2015 Nov 20;214:45-6. doi: 10.1016/j.jbiotec.2015.09.010. Epub 2015 Sep 14. PubMed PMID: 26376468. 4: Guiboux AL, Dautriche A, Rocher F, Bruel M, Sgro C; les centres régionaux de pharmacovigilance. [Pristinamycin/Vitamin k antagonists drug interaction: a French pharmacovigilance database study]. Therapie. 2014 Sep-Oct;69(5):391-4. doi: 10.2515/therapie/2014033. Epub 2014 Jul 23. French. PubMed PMID: 25047671. 5: Viel S, Garnier L, Joly E, Rouzaire P, Nosbaum A, Pralong P, Faudel A, Rioufol C, Bienvenu F, Bienvenu J, Berard F. The basophil activation test: a sensitive test in the diagnosis of allergic immediate hypersensitivity to pristinamycin. Int Arch Allergy Immunol. 2015;167(2):94-8. doi: 10.1159/000435812. Epub 2015 Jul 22. PubMed PMID: 26202178. 6: Wang W, Tian J, Li L, Ge M, Zhu H, Zheng G, Huang H, Ruan L, Jiang W, Lu Y. Identification of two novel regulatory genes involved in pristinamycin biosynthesis and elucidation of the mechanism for AtrA-p-mediated regulation in Streptomyces pristinaespiralis. Appl Microbiol Biotechnol. 2015 Sep;99(17):7151-64. doi: 10.1007/s00253-015-6638-6. Epub 2015 May 10. PubMed PMID: 25957493. 7: Teng JC, Lingaratnam SM, Trubiano JA, Thursky KA, Slavin MA, Worth LJ. Oral pristinamycin for the treatment of resistant Gram-positive infections in patients with cancer: Evaluation of clinical outcomes. Int J Antimicrob Agents. 2016 May;47(5):391-6. doi: 10.1016/j.ijantimicag.2016.01.017. Epub 2016 Mar 12. PubMed PMID: 27089829. 8: Zhao Y, Feng R, Zheng G, Tian J, Ruan L, Ge M, Jiang W, Lu Y. Involvement of the TetR-Type Regulator PaaR in the Regulation of Pristinamycin I Biosynthesis through an Effect on Precursor Supply in Streptomyces pristinaespiralis. J Bacteriol. 2015 Jun 15;197(12):2062-71. doi: 10.1128/JB.00045-15. Epub 2015 Apr 13. PubMed PMID: 25868645; PubMed Central PMCID: PMC4438209. 9: Schmutz JL, Trechot P. [Skin rash mimicking pityriasis rosea Gibert secondary to pristinamycin therapy]. Ann Dermatol Venereol. 2014 Apr;141(4):325-6. doi: 10.1016/j.annder.2014.01.001. Epub 2014 Feb 7. French. PubMed PMID: 24703654. 10: Jin QC, Shen N, Yin H, Yang Y, Jin ZH. [DNA shuffling of ptr resistance gene leads to improved pristinamycin production in Streptomyces pristinaespiralis]. Mol Biol (Mosk). 2015 Mar-Apr;49(2):289-96. Russian. PubMed PMID: 26065256. 11: Valour F, Boibieux A, Karsenty J, Vallat MP, Braun E, Perpoint T, Biron F, Laurent F, Lustig S, Chidiac C, Ferry T; Lyon Bone and Joint Infection Study Group. Pristinamycin in the treatment of MSSA bone and joint infection. J Antimicrob Chemother. 2016 Apr;71(4):1063-70. doi: 10.1093/jac/dkv457. Epub 2016 Jan 21. PubMed PMID: 26801082. 12: Li L, Zhao Y, Ruan L, Yang S, Ge M, Jiang W, Lu Y. A stepwise increase in pristinamycin II biosynthesis by Streptomyces pristinaespiralis through combinatorial metabolic engineering. Metab Eng. 2015 May;29:12-25. doi: 10.1016/j.ymben.2015.02.001. Epub 2015 Feb 20. PubMed PMID: 25708513. 13: Mallikarjuna Rao N, Gowrisankar D. Development and Validation of a Stability-Indicating RP-HPLC Method for the Assay of Pristinamycin in Bulk and Tablet Dosage Form. Sci Pharm. 2016 Apr-Jun;84(2):279-87. doi: 10.3797/scipharm.1506-01. Epub 2015 Jul 22. PubMed PMID: 27222604; PubMed Central PMCID: PMC4871181. 14: Zhang LJ, Jin ZH, Chen XG, Jin QC, Feng MG. Glycine feeding improves pristinamycin production during fermentation including resin for in situ separation. Bioprocess Biosyst Eng. 2012 May;35(4):513-7. doi: 10.1007/s00449-011-0624-x. Epub 2011 Sep 25. PubMed PMID: 21947672. 15: Jin Q, Jin Z, Zhang L, Yao S, Li F. Probing the molecular mechanisms for pristinamycin yield enhancement in Streptomyces pristinaespiralis. Curr Microbiol. 2012 Dec;65(6):792-8. doi: 10.1007/s00284-012-0233-1. Epub 2012 Sep 19. PubMed PMID: 22991052. 16: Mezghani Maalej S, Malbruny B, Leclercq R, Hammami A. Emergence of Staphylococcus aureus strains resistant to pristinamycin in Sfax (Tunisia). Pathol Biol (Paris). 2012 Dec;60(6):e71-4. doi: 10.1016/j.patbio.2011.10.012. Epub 2012 Jan 20. PubMed PMID: 22265593. 17: Catho G, Ader F, Chidiac C, Ferry T. Acute generalised exanthematous pustulosis due to pristinamycin. BMJ Case Rep. 2013 Mar 6;2013. pii: bcr2013008594. doi: 10.1136/bcr-2013-008594. PubMed PMID: 23470673; PubMed Central PMCID: PMC3618774. 18: Mast Y, Weber T, Gölz M, Ort-Winklbauer R, Gondran A, Wohlleben W, Schinko E. Characterization of the 'pristinamycin supercluster' of Streptomyces pristinaespiralis. Microb Biotechnol. 2011 Mar;4(2):192-206. doi: 10.1111/j.1751-7915.2010.00213.x. Epub 2010 Oct 15. PubMed PMID: 21342465; PubMed Central PMCID: PMC3818860. 19: Dun J, Zhao Y, Zheng G, Zhu H, Ruan L, Wang W, Ge M, Jiang W, Lu Y. PapR6, a putative atypical response regulator, functions as a pathway-specific activator of pristinamycin II biosynthesis in Streptomyces pristinaespiralis. J Bacteriol. 2015 Feb;197(3):441-50. doi: 10.1128/JB.02312-14. Epub 2014 Nov 17. PubMed PMID: 25404695; PubMed Central PMCID: PMC4285971. 20: Schmutz JL, Trechot P. [Pristinamycin and anaphylactic reaction]. Ann Dermatol Venereol. 2011 Oct;138(10):720. doi: 10.1016/j.annder.2011.05.011. Epub 2011 Jun 30. Review. French. PubMed PMID: 21978517.