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MedKoo Cat#: 571033 | Name: Cephamycin C

Description:

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

Cephamycin C (CepC) is a nontoxic β-lactam antibiotic that belongs to the cephalosporin class of drugs produced by Streptomyces clavuligerus. This compound stands out from other cephalosporins for its greater resistance to β-lactamases, which are enzymes produced by pathogenic microorganisms that present a major mechanism of bacterial resistance to β-lactam antibiotics. Cephamycin C is a more stable compound than other β-lactam compounds such as penicillin and clavulanic acid.

Chemical Structure

Cephamycin C
CAS#38429-35-5

Theoretical Analysis

MedKoo Cat#: 571033

Name: Cephamycin C

CAS#: 38429-35-5

Chemical Formula: C16H22N4O9S

Exact Mass: 446.1107

Molecular Weight: 446.43

Elemental Analysis: C, 43.05; H, 4.97; N, 12.55; O, 32.25; S, 7.18

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
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Synonym
Cephamycin C; A 16886B; A16886B, A-16886B
IUPAC/Chemical Name
5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 3-(((aminocarbonyl)oxy)methyl)-7-((5-amino-5-carboxy-1-oxopentyl)amino)-7-methoxy-8-oxo-
InChi Key
LXWBXEWUSAABOA-UHFFFAOYSA-N
InChi Code
InChI=1S/C16H22N4O9S/c1-28-16(19-9(21)4-2-3-8(17)11(22)23)13(26)20-10(12(24)25)7(5-29-15(18)27)6-30-14(16)20/h8,14H,2-6,17H2,1H3,(H2,18,27)(H,19,21)(H,22,23)(H,24,25)
SMILES Code
O=C(C(N12)=C(COC(N)=O)CSC2C(OC)(NC(CCCC(N)C(O)=O)=O)C1=O)O
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).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 446.43 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
1: Martínez-Burgo Y, Álvarez-Álvarez R, Pérez-Redondo R, Liras P. Heterologous expression of Streptomyces clavuligerus ATCC 27064 cephamycin C gene cluster. J Biotechnol. 2014 Sep 30;186:21-9. doi: 10.1016/j.jbiotec.2014.06.002. Epub 2014 Jun 26. PubMed PMID: 24975573. 2: Brites LM, Oliveira LM, Barboza M. Kinetic study on cephamycin C degradation. Appl Biochem Biotechnol. 2013 Dec;171(8):2121-8. doi: 10.1007/s12010-013-0502-x. Epub 2013 Sep 12. PubMed PMID: 24026415. 3: Alvarez-Álvarez R, Rodríguez-García A, Santamarta I, Pérez-Redondo R, Prieto-Domínguez A, Martínez-Burgo Y, Liras P. Transcriptomic analysis of Streptomyces clavuligerus ΔccaR::tsr: effects of the cephamycin C-clavulanic acid cluster regulator CcaR on global regulation. Microb Biotechnol. 2014 May;7(3):221-31. doi: 10.1111/1751-7915.12109. Epub 2014 Jan 22. PubMed PMID: 24450885; PubMed Central PMCID: PMC3992018. 4: Leite CA, Cavallieri AP, Araujo ML. Enhancing effect of lysine combined with other compounds on cephamycin C production in Streptomyces clavuligerus. BMC Microbiol. 2013 Dec 20;13:296. doi: 10.1186/1471-2180-13-296. PubMed PMID: 24359569; PubMed Central PMCID: PMC3880171. 5: Neto Ade B, Bustamante MC, Oliveira JH, Granato AC, Bellão C, Badino AC, Barboza M, Hokka CO. Preliminary studies for cephamycin C purification technique. Appl Biochem Biotechnol. 2012 Jan;166(1):208-21. doi: 10.1007/s12010-011-9417-6. Epub 2011 Nov 5. Erratum in: Appl Biochem Biotechnol. 2012 Jan;166(1):258. PubMed PMID: 22057909. 6: Kurt A, Álvarez-Álvarez R, Liras P, Özcengiz G. Role of the cmcH-ccaR intergenic region and ccaR overexpression in cephamycin C biosynthesis in Streptomyces clavuligerus. Appl Microbiol Biotechnol. 2013 Jul;97(13):5869-80. doi: 10.1007/s00253-013-4721-4. Epub 2013 Jan 30. PubMed PMID: 23361841. 7: Leite CA, Cavallieri AP, Baptista AS, Araujo ML. Dissociation of cephamycin C and clavulanic acid biosynthesis by 1,3-diaminopropane in Streptomyces clavuligerus. FEMS Microbiol Lett. 2016 Jan;363(1):fnv215. doi: 10.1093/femsle/fnv215. Epub 2015 Nov 11. PubMed PMID: 26564965. 8: Kagliwal LD, Survase SA, Singhal RS. A novel medium for the production of cephamycin C by Nocardia lactamdurans using solid-state fermentation. Bioresour Technol. 2009 May;100(9):2600-6. doi: 10.1016/j.biortech.2008.11.046. Epub 2009 Jan 19. PubMed PMID: 19155173. 9: Jin W, Kim HK, Kim JY, Kang SG, Lee SH, Lee KJ. Cephamycin C production is regulated by relA and rsh genes in Streptomyces clavuligerus ATCC27064. J Biotechnol. 2004 Oct 19;114(1-2):81-7. PubMed PMID: 15464601. 10: Park YS, Momose I, Tsunoda K, Okabe M. Enhancement of cephamycin C production using soybean oil as the sole carbon source. Appl Microbiol Biotechnol. 1994 Feb;40(6):773-9. PubMed PMID: 7764568. 11: Bussari B, Saudagar PS, Shaligram NS, Survase SA, Singhal RS. Production of cephamycin C by Streptomyces clavuligerus NT4 using solid-state fermentation. J Ind Microbiol Biotechnol. 2008 Jan;35(1):49-58. Epub 2007 Oct 17. PubMed PMID: 17940818. 12: Jacks TM, Schleim KD, Judith FR, Miller BM. Cephamycin C treatment of induced enterotoxigenic colibacillosis (scours) in calves and piglets. Antimicrob Agents Chemother. 1980 Sep;18(3):397-402. PubMed PMID: 6999985; PubMed Central PMCID: PMC284013. 13: Coque JJ, Enguita FJ, Martín JF, Liras P. A two-protein component 7 alpha-cephem-methoxylase encoded by two genes of the cephamycin C cluster converts cephalosporin C to 7-methoxycephalosporin C. J Bacteriol. 1995 Apr;177(8):2230-5. PubMed PMID: 7721717; PubMed Central PMCID: PMC176873. 14: Alexander DC, Anders CL, Lee L, Jensen SE. pcd mutants of Streptomyces clavuligerus still produce cephamycin C. J Bacteriol. 2007 Aug;189(16):5867-74. Epub 2007 Jun 15. PubMed PMID: 17573474; PubMed Central PMCID: PMC1952048. 15: Liras P. Biosynthesis and molecular genetics of cephamycins. Cephamycins produced by actinomycetes. Antonie Van Leeuwenhoek. 1999 Jan-Feb;75(1-2):109-24. Review. PubMed PMID: 10422584. 16: Khaoua S, Lebrihi A, Germain P, Lefebvre G. Cephamycin C biosynthesis in Streptomyces cattleya: nitrogen source regulation. Appl Microbiol Biotechnol. 1991 May;35(2):253-7. PubMed PMID: 1367371. 17: Özcengiz G, Okay S, Ünsaldı E, Taşkın B, Liras P, Piret J. Homologous expression of aspartokinase (ask) gene in Streptomyces clavuligerus and its hom-deleted mutant: effects on cephamycin C production. Bioeng Bugs. 2010 May-Jun;1(3):191-7. doi: 10.4161/bbug.1.3.11244. Epub 2010 Jan 11. PubMed PMID: 21326925; PubMed Central PMCID: PMC3026424. 18: Jacks TM, Welter CJ, Fitzgerald GR, Miller BM. Cephamycin C treatment of induced swine salmonellosis. Antimicrob Agents Chemother. 1981 Apr;19(4):562-6. PubMed PMID: 7247378; PubMed Central PMCID: PMC181477. 19: Miller AK, Celozzi E, Kong Y, Pelak BA, Kropp H, Stapley EO, Hendlin D. Cephamycins, a new family of beta-lactam antibiotics. IV. In vivo studies. Antimicrob Agents Chemother. 1972 Oct;2(4):287-90. PubMed PMID: 4670502; PubMed Central PMCID: PMC444308. 20: Gomez-Escribano JP, Martín JF, Hesketh A, Bibb MJ, Liras P. Streptomyces clavuligerus relA-null mutants overproduce clavulanic acid and cephamycin C: negative regulation of secondary metabolism by (p)ppGpp. Microbiology. 2008 Mar;154(Pt 3):744-55. doi: 10.1099/mic.0.2007/011890-0. PubMed PMID: 18310021.