Efrotomycin

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

MedKoo CAT#: 584757

CAS#: 56592-32-6

Description: Efrotomycin is an antibiotic from Streptomyces lactamdurans.

Chemical Structure

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Efrotomycin
CAS# 56592-32-6
Instruction

Theoretical Analysis

MedKoo Cat#: 584757
Name: Efrotomycin
CAS#: 56592-32-6
Chemical Formula: C59H88N2O20
Exact Mass: 1,144.59
Molecular Weight: 1,145.347
Elemental Analysis: C, 61.87; H, 7.74; N, 2.45; O, 27.94

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: Efrotomycin; FR 02A; FR-02A; FR02A; MK-621; MK 621; MK621;

IUPAC/Chemical Name: (alphaS,2R,3R,4R,6S)-4-((6-Deoxy-4-O-(6-deoxy-2,4-di-O-methyl-alpha-L-mannopyranosyl)-3-O-methyl-beta-D-allopyranosyl)oxy)-N-((2E,4E,6S,7R)-7-((2S,3S,4R,5R)-5-((1E,3E,5E)-6-(1,2-dihydro-4-hydroxy-1-methyl-2-oxonicotinoyl)-1,3,5-heptatrienyl)tetrahydro-3,4-dihydroxy-2-furyl)-6-methoxy-5-methyl-2,4-octadienyl)-alpha-ethyltetrahydro-2,3-dihydroxy-5,5-dimethyl-6-((1E,3Z)-1,3-pentadienyl)-2H-pyran-2-acetamide

InChi Key: ASOJLQIBBYOFDE-SBHXXGSWSA-N

InChi Code: InChI=1S/C59H88N2O20/c1-15-17-19-27-39-58(8,9)53(80-56-45(67)50(74-13)49(35(7)76-56)79-57-51(75-14)44(66)48(73-12)34(6)77-57)52(68)59(71,81-39)36(16-2)54(69)60-29-23-22-25-32(4)46(72-11)33(5)47-43(65)42(64)38(78-47)26-21-18-20-24-31(3)41(63)40-37(62)28-30-61(10)55(40)70/h15,17-28,30,33-36,38-39,42-53,56-57,62,64-68,71H,16,29H2,1-14H3,(H,60,69)/b17-15-,20-18+,23-22+,26-21+,27-19+,31-24+,32-25+/t33-,34+,35-,36-,38-,39+,42+,43+,44-,45-,46-,47+,48+,49-,50+,51-,52-,53+,56+,57+,59-/m1/s1

SMILES Code: O=C(NC/C=C/C=C(C)/[C@@H](OC)[C@H]([C@@H]1O[C@H](/C=C/C=C/C=C(C(C2=C(O)C=CN(C)C2=O)=O)\C)[C@H](O)[C@@H]1O)C)[C@@H](CC)[C@]3(O)[C@H](O)[C@H](O[C@H]4[C@@H]([C@@H]([C@@H]([C@@H](C)O4)O[C@H]5[C@@H]([C@@H]([C@H]([C@H](C)O5)OC)O)OC)OC)O)C(C)(C)[C@H](/C=C/C=C\C)O3

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: 2934.99.9001

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 1,145.35 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: Landini P, Bandera M, Goldstein BP, Ripamonti F, Soffientini A, Islam K, Denaro M. Inhibition of bacterial protein synthesis by elongation-factor-Tu-binding antibiotics MDL 62,879 and efrotomycin. Biochem J. 1992 May 1;283 ( Pt 3):649-52. PubMed PMID: 1590753; PubMed Central PMCID: PMC1130934.

2: Nielsen JB, Kaplan L. A resting cell system for efrotomycin biosynthesis. J Antibiot (Tokyo). 1989 Jun;42(6):944-51. PubMed PMID: 2737954.

3: Foster AG, Baker DH, Cline TR, Cromwell GL, Veum TL, Alva-Valdes R, Ericsson GF. Effect of efrotomycin on gain and feed efficiency for pigs from weaning until market weight. J Anim Sci. 1987 Oct;65(4):877-80. PubMed PMID: 3667459.

4: Jacks TM, Frazier EG, Abruzzo GK, Graham AC, Fromtling RA. Lack of cross-resistance between efrotomycin and antibacterial agents used in the therapy of human and animal infections. Methods Find Exp Clin Pharmacol. 1989 Nov;11(11):697-701. PubMed PMID: 2695724.

5: Darland G, Arison B, Kaplan L. The biosynthetic origin of the pyridone ring of efrotomycin. J Ind Microbiol. 1991 Nov;8(4):265-71. PubMed PMID: 1367801.

6: Jefson MR, Bordner J, Reese CP, Whipple EB. UK-69,753, a novel member of the efrotomycin family of antibiotics. II. Structure determination and biological activity. J Antibiot (Tokyo). 1989 Nov;42(11):1610-8. PubMed PMID: 2584145.

7: Carvalho MG, Teixeira LM, Facklam RR. Use of tests for acidification of methyl-alpha-D-glucopyranoside and susceptibility to efrotomycin for differentiation of strains of Enterococcus and some related genera. J Clin Microbiol. 1998 Jun;36(6):1584-7. PubMed PMID: 9620381; PubMed Central PMCID: PMC104881.

8: Chartrain M, Hunt G, Horn L, Kirpekar A, Mathre D, Powell A, Wassel L, Nielsen J, Buckland B, Greasham R. Biochemical and physiological characterization of the efrotomycin fermentation. J Ind Microbiol. 1991 Jun;7(4):293-9. PubMed PMID: 1367328.

9: Newsom SW, Matthews J, Rampling AM. Susceptibility of Clostridium difficile strains to new antibiotics: quinolones, efrotomycin, teicoplanin and imipenem. J Antimicrob Chemother. 1985 May;15(5):648-9. PubMed PMID: 3159714.

10: Dewey RS, Arison BH, Hannah J, Shih DH, Albers-Schönberg G. The structure of efrotomycin. J Antibiot (Tokyo). 1985 Dec;38(12):1691-8. PubMed PMID: 4093333.

11: Frost BM, Valiant ME, Dulaney EL. Antibacterial activity of heneicomycin. J Antibiot (Tokyo). 1979 Jun;32(6):626-9. PubMed PMID: 468738.

12: Landini P, Bandera M, Soffientini A, Goldstein BP. Sensitivity of elongation factor Tu (EF-Tu) from different bacterial species to the antibiotics efrotomycin, pulvomycin and MDL 62879. J Gen Microbiol. 1993 Apr;139(4):769-74. PubMed PMID: 8515234.

13: Stutz MW, Johnson SL, Judith FR, Miller BM. In vitro and in vivo evaluations of the antibiotic efrotomycin. Poult Sci. 1983 Aug;62(8):1612-8. PubMed PMID: 6314312.

14: Frost BM, Valiant ME, Dulaney EL. Synergism between efrotomycin and bottromycin. J Antibiot (Tokyo). 1979 Oct;32(10):1046-9. PubMed PMID: 528364.

15: Pacey MS, Jefson MR, Huang LH, Cullen WP, Maeda H, Tone J, Nishiyama S, Kaneda K, Ishiguro M. UK-69,753, a novel member of the efrotomycin family of antibiotics. I. Taxonomy of the producing organism, fermentation and isolation. J Antibiot (Tokyo). 1989 Oct;42(10):1453-9. PubMed PMID: 2808132.

16: Frost BM, Valiant ME, Weissberger B, Dulaney EL. Antibacterial activity of efrotomycin. J Antibiot (Tokyo). 1976 Oct;29(10):1083-91. PubMed PMID: 994327.

17: Maeda H, Bordner J, Cullen W, Huang L, Jefson M, Kaneda K, Niki K, Nishiyama S, Tone J, Whipple E. [UK-69,753, a new antibiotic related to efrotomycin and factumycin (A40A)]. Jpn J Antibiot. 1988 May;41(5):604. Japanese. PubMed PMID: 3216485.

18: Jacks TM, Frazier E, Judith FR, Olson G. Effect of efrotomycin in feed on the quantity, duration, and prevalence of shedding and antibacterial susceptibility of Salmonella typhimurium in experimentally infected swine. Am J Vet Res. 1988 Nov;49(11):1832-5. PubMed PMID: 3073676.

19: Feighner SD, Dashkevicz MP. Subtherapeutic levels of antibiotics in poultry feeds and their effects on weight gain, feed efficiency, and bacterial cholyltaurine hydrolase activity. Appl Environ Microbiol. 1987 Feb;53(2):331-6. PubMed PMID: 3566269; PubMed Central PMCID: PMC203661.

20: Kempf AJ, Wilson KE, Hensens OD, Monaghan RL, Zimmerman SB, Dulaney EL. L-681,217, a new and novel member of the efrotomycin family of antibiotics. J Antibiot (Tokyo). 1986 Oct;39(10):1361-7. PubMed PMID: 3781906.