Davercin
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MedKoo CAT#: 530487

CAS#: 55224-05-0

Description: Davercin, also known as Erythromycin Cyclocarbonate, is a bacteriostatic antibiotic macrolide produced by Streptomyces erythreus. It inhibits protein synthesis by binding to 50S ribosomal subunits. This binding process inhibits peptidyl transferase activity and interferes with translocation of amino acids during translation and assembly of proteins.


Price and Availability

Size
Price

25mg
USD 150
1g
USD 2450
Size
Price

100mg
USD 450
2g
USD 3650
Size
Price

200mg
USD 750

Davercin, purity > 98%, is in stock. The same day shipping out after order is received. Note: the estimated shipping out time for order > 2g may be 2 weeks.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 530487
Name: Davercin
CAS#: 55224-05-0
Chemical Formula: C38H65NO14
Exact Mass: 759.4405
Molecular Weight: 759.93
Elemental Analysis: C, 60.06; H, 8.62; N, 1.84; O, 29.47


Synonym: Erythromycin A; Erythromycin A 11,12-carbonate; Erythromycin A cyclic carbonate; Davercin.

IUPAC/Chemical Name: (3aR,4R,7R,8S,9S,10R,11R,13R,15R,15aR)-10-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4-ethyl-11-hydroxy-8-(((2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydro-2H-pyran-2-yl)oxy)-3a,7,9,11,13,15-hexamethyldecahydro-6H-[1,3]dioxolo[4,5-c][1]oxacyclotetradecine-2,6,14(7H)-trione

InChi Key: NKLGIWNNVDPGCA-ZDYKNUMJSA-N

InChi Code: InChI=1S/C38H65NO14/c1-14-25-38(10)32(52-35(44)53-38)20(4)27(40)18(2)16-36(8,45)31(51-34-28(41)24(39(11)12)15-19(3)47-34)21(5)29(22(6)33(43)49-25)50-26-17-37(9,46-13)30(42)23(7)48-26/h18-26,28-32,34,41-42,45H,14-17H2,1-13H3/t18-,19-,20+,21+,22-,23+,24+,25-,26+,28-,29+,30+,31-,32-,34+,36-,37-,38-/m1/s1

SMILES Code: CC[C@H]1OC(=O)[C@H](C)[C@@H](O[C@H]2C[C@@](C)(OC)[C@@H](O)[C@H](C)O2)[C@H](C)[C@@H](O[C@@H]3O[C@H](C)C[C@@H]([C@H]3O)N(C)C)[C@](C)(O)C[C@@H](C)C(=O)[C@H](C)[C@H]4OC(=O)O[C@]14C


Technical Data

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:
>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).

Harmonized System Code:
293490


References

1: Zhang W, Qiu L, Gong A, Yuan X. Isolation and characterization of a high-efficiency erythromycin A-degrading Ochrobactrum sp. strain. Mar Pollut Bull. 2017 Jan 30;114(2):896-902. doi: 10.1016/j.marpolbul.2016.10.076. PubMed PMID: 27863881.

2: Pierattini EC, Francini A, Raffaelli A, Sebastiani L. Morpho-physiological response of Populus alba to erythromycin: A timeline of the health status of the plant. Sci Total Environ. 2016 Nov 1;569-570:540-7. doi: 10.1016/j.scitotenv.2016.06.152. PubMed PMID: 27366984.

3: Chen D, Wu J, Liu W. [Biosynthesis-based production improvement and structure modification of erythromycin A]. Sheng Wu Gong Cheng Xue Bao. 2015 Jun;31(6):939-54. Review. Chinese. PubMed PMID: 26672369.

4: Jiang M, Fang L, Pfeifer BA. Improved heterologous erythromycin A production through expression plasmid re-design. Biotechnol Prog. 2013 Jul-Aug;29(4):862-9. doi: 10.1002/btpr.1759. PubMed PMID: 23804312.

5: Magee TV, Han S, McCurdy SP, Nguyen TT, Granskog K, Marr ES, Maguire BA, Huband MD, Chen JM, Subashi TA, Shanmugasundaram V. Novel 3-O-carbamoyl erythromycin A derivatives (carbamolides) with activity against resistant staphylococcal and streptococcal isolates. Bioorg Med Chem Lett. 2013 Mar 15;23(6):1727-31. doi: 10.1016/j.bmcl.2013.01.067. PubMed PMID: 23414806.

6: Jiang M, Zhang H, Pfeifer BA. The logic, experimental steps, and potential of heterologous natural product biosynthesis featuring the complex antibiotic erythromycin A produced through E. coli. J Vis Exp. 2013 Jan 13;(71):e4346. doi: 10.3791/4346. PubMed PMID: 23354010; PubMed Central PMCID: PMC3582574.

7: Romøren M, Lindbæk M, Nordeng H. Pregnancy outcome after gestational exposure to erythromycin - a population-based register study from Norway. Br J Clin Pharmacol. 2012 Dec;74(6):1053-62. doi: 10.1111/j.1365-2125.2012.04286.x. PubMed PMID: 22463376; PubMed Central PMCID: PMC3522819.

8: Brüning J, Trepte TK, Bats JW, Schmidt MU. Erythromycin A dimethyl sulfoxide disolvate 1.43-hydrate. Acta Crystallogr Sect E Struct Rep Online. 2012 Mar 1;68(Pt 3):o700-1. doi: 10.1107/S1600536812005223. PubMed PMID: 22412590; PubMed Central PMCID: PMC3295479.

9: Zhang H, Skalina K, Jiang M, Pfeifer BA. Improved E. coli erythromycin A production through the application of metabolic and bioprocess engineering. Biotechnol Prog. 2012 Jan-Feb;28(1):292-6. doi: 10.1002/btpr.702. PubMed PMID: 21905273.

10: Wu J, Zhang Q, Deng W, Qian J, Zhang S, Liu W. Toward improvement of erythromycin A production in an industrial Saccharopolyspora erythraea strain via facilitation of genetic manipulation with an artificial attB site for specific recombination. Appl Environ Microbiol. 2011 Nov;77(21):7508-16. doi: 10.1128/AEM.06034-11. PubMed PMID: 21841022; PubMed Central PMCID: PMC3209160.

11: Sugawara A, Sueki A, Hirose T, Nagai K, Gouda H, Hirono S, Shima H, Akagawa KS, Omura S, Sunazuka T. Novel 12-membered non-antibiotic macrolides from erythromycin A; EM900 series as novel leads for anti-inflammatory and/or immunomodulatory agents. Bioorg Med Chem Lett. 2011 Jun 1;21(11):3373-6. doi: 10.1016/j.bmcl.2011.04.004. PubMed PMID: 21524580.

12: Ma X, Ma S. Significant breakthroughs in search for anti-infectious agents derived from erythromycin A. Curr Med Chem. 2011;18(13):1993-2015. Review. PubMed PMID: 21517774.

13: Zhang L, Jiao B, Yang X, Liu L, Ma S. Synthesis and antibacterial activity of new 4″-O-carbamates of 11,12-cyclic carbonate erythromycin A 6,9-imino ether. J Antibiot (Tokyo). 2011 Mar;64(3):243-7. doi: 10.1038/ja.2010.166. Erratum in: J Antibiot (Tokyo). 2012 Feb;65(2):115. PubMed PMID: 21245870.

14: Zhang H, Wang Y, Wu J, Skalina K, Pfeifer BA. Complete biosynthesis of erythromycin A and designed analogs using E. coli as a heterologous host. Chem Biol. 2010 Nov 24;17(11):1232-40. doi: 10.1016/j.chembiol.2010.09.013. PubMed PMID: 21095573.

15: Luiz DB, Genena AK, Virmond E, José HJ, Moreira RF, Gebhardt W, Schröder HF. Identification of degradation products of erythromycin A arising from ozone and advanced oxidation process treatment. Water Environ Res. 2010 Sep-Oct;82(9):797-805. PubMed PMID: 20942335.

16: Qi Y, Jiao B, Ma X, Cui W, Ma S. Synthesis and antibacterial activity of novel 4''-O-carbamoyl erythromycin-A derivatives. Arch Pharm (Weinheim). 2010 Aug;343(8):458-64. doi: 10.1002/ardp.200900288. PubMed PMID: 20803622.

17: Shiina I, Katoh T, Nagai S, Hashizume M. Evaluation of the efficiency of the macrolactonization using MNBA in the synthesis of erythromycin A aglycon. Chem Rec. 2009;9(6):305-20. doi: 10.1002/tcr.200900017. Erratum in: Chem Rec. 2010 Apr 26;10(2) doi: 10.1002/tcr.201090004. PubMed PMID: 20041452.

18: Namikawa H, Sunazuka T, Kitamura Y, Suzuki T, Hamasaki Y, Yamazaki S, Omura S, Hatamochi A. Effect of erythromycin A and its new derivative EM201 on type I collagen production by cultured dermal fibroblasts. Arch Dermatol Res. 2010 Jul;302(5):341-8. doi: 10.1007/s00403-009-0977-z. PubMed PMID: 19578864.

19: Zou X, Hang HF, Chu J, Zhuang YP, Zhang SL. Enhancement of erythromycin A production with feeding available nitrogen sources in erythromycin biosynthesis phase. Bioresour Technol. 2009 Jul;100(13):3358-65. doi: 10.1016/j.biortech.2009.01.064. PubMed PMID: 19268575.

20: Pandey D, Haq W, Katti SB. New acylides: synthesis of 3-O-[gamma-(4-oxo-2-aryl-thiazolidin-3-yl)butyryl]erythromycin A derivatives. Beilstein J Org Chem. 2008;4:14. doi: 10.3762/bjoc.4.14. PubMed PMID: 18941486; PubMed Central PMCID: PMC2486485.