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MedKoo Cat#: 414251 | Name: RWJ-54428

Description:

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

RWJ-54428 is a new cephalosporin active against gram-positive bacteria, including methicillin-resistant Staphylococcus aureus (MRSA).

Chemical Structure

RWJ-54428
RWJ-54428
CAS#189448-35-9

Theoretical Analysis

MedKoo Cat#: 414251

Name: RWJ-54428

CAS#: 189448-35-9

Chemical Formula: C20H20ClN7O5S4

Exact Mass: 601.0097

Molecular Weight: 602.11

Elemental Analysis: C, 39.90; H, 3.35; Cl, 5.89; N, 16.28; O, 13.29; S, 21.30

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 #
No Data
Synonym
RWJ-54428; RWJ 54428; RWJ54428; MC02479; MC-02479; MC 02479
IUPAC/Chemical Name
5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7-(((2-amino-5-chloro-4-thiazolyl)(hydroxyimino)acetyl)amino)-3-((3-(((2-aminoethyl)thio)methyl)-4-pyridinyl)thio)-8-oxo-, (6R-(6alpha,7beta(Z)))-
InChi Key
LTUWUNMGTLOPNC-RLQAYIIJSA-N
InChi Code
InChI=1S/C20H20ClN7O5S4/c21-15-11(26-20(23)37-15)12(27-33)16(29)25-13-17(30)28-14(19(31)32)10(7-35-18(13)28)36-9-1-3-24-5-8(9)6-34-4-2-22/h1,3,5,13,18,33H,2,4,6-7,22H2,(H2,23,26)(H,25,29)(H,31,32)/b27-12-/t13-,18-/m1/s1
SMILES Code
O=C(C(N12)=C(SC3=C(CSCCN)C=NC=C3)CS[C@]2([H])[C@H](NC(/C(C4=C(Cl)SC(N)=N4)=N\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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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 602.11 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: Shahid M, Sobia F, Singh A, Malik A, Khan HM, Jonas D, Hawkey PM. Beta- lactams and beta-lactamase-inhibitors in current- or potential-clinical practice: a comprehensive update. Crit Rev Microbiol. 2009;35(2):81-108. doi: 10.1080/10408410902733979. PMID: 19514910. 2: Griffith DC, Rodriguez D, Corcoran E, Dudley MN. Pharmacodynamics of RWJ-54428 against Staphylococcus aureus, Streptococcus pneumoniae, and Enterococcus faecalis in a neutropenic mouse thigh infection model. Antimicrob Agents Chemother. 2008 Jan;52(1):244-7. doi: 10.1128/AAC.00776-07. Epub 2007 Oct 22. PMID: 17954697; PMCID: PMC2223871. 3: Hoffman-Roberts HL, C Babcock E, Mitropoulos IF. Investigational new drugs for the treatment of resistant pneumococcal infections. Expert Opin Investig Drugs. 2005 Aug;14(8):973-95. doi: 10.1517/13543784.14.8.973. PMID: 16050791. 4: Bozdogan B, Esel D, Whitener C, Browne FA, Appelbaum PC. Antibacterial susceptibility of a vancomycin-resistant Staphylococcus aureus strain isolated at the Hershey Medical Center. J Antimicrob Chemother. 2003 Nov;52(5):864-8. doi: 10.1093/jac/dkg457. Epub 2003 Oct 16. PMID: 14563898. 5: Abbanat D, Macielag M, Bush K. Novel antibacterial agents for the treatment of serious Gram-positive infections. Expert Opin Investig Drugs. 2003 Mar;12(3):379-99. doi: 10.1517/13543784.12.3.379. PMID: 12605562. 6: Malouin F, Blais J, Chamberland S, Hoang M, Park C, Chan C, Mathias K, Hakem S, Dupree K, Liu E, Nguyen T, Dudley MN. RWJ-54428 (MC-02,479), a new cephalosporin with high affinity for penicillin-binding proteins, including PBP 2a, and stability to staphylococcal beta-lactamases. Antimicrob Agents Chemother. 2003 Feb;47(2):658-64. doi: 10.1128/AAC.47.2.658-664.2003. PMID: 12543674; PMCID: PMC151748. 7: Hoellman DB, Kelly LM, Jacobs MR, Appelbaum PC. In vitro anti-anaerobic activity of the cephalosporin derivative RWJ 54428, compared to seven other compounds. Clin Microbiol Infect. 2002 Dec;8(12):814-22. doi: 10.1046/j.1469-0691.2002.00475.x. PMID: 12519357. 8: Griffith DC, Harford L, Williams R, Lee VJ, Dudley MN. In vivo antibacterial activity of RWJ-54428, a new cephalosporin with activity against gram-positive bacteria. Antimicrob Agents Chemother. 2003 Jan;47(1):43-7. doi: 10.1128/AAC.47.1.43-47.2003. PMID: 12499167; PMCID: PMC149000. 9: Swenson JM, Tenover FC. In vitro activity of a new cephalosporin, RWJ-54428, against streptococci, enterococci and staphylococci, including glycopeptide- intermediate Staphylococcus aureus. J Antimicrob Chemother. 2002 May;49(5):845-50. doi: 10.1093/jac/dkf020. PMID: 12003982. 10: Johnson AP, Warner M, Carter M, Livermore DM. In vitro activity of cephalosporin RWJ-54428 (MC-02479) against multidrug-resistant gram-positive cocci. Antimicrob Agents Chemother. 2002 Feb;46(2):321-6. doi: 10.1128/AAC.46.2.321-326.2002. PMID: 11796337; PMCID: PMC127043. 11: Chamberland S, Blais J, Hoang M, Dinh C, Cotter D, Bond E, Gannon C, Park C, Malouin F, Dudley MN. In vitro activities of RWJ-54428 (MC-02,479) against multiresistant gram-positive bacteria. Antimicrob Agents Chemother. 2001 May;45(5):1422-30. doi: 10.1128/AAC.45.5.1422-1430.2001. PMID: 11302805; PMCID: PMC90483. 12: Hecker SJ, Glinka TW, Cho A, Zhang ZJ, Price ME, Chamberland S, Griffith D, Lee VJ. Discovery of RWJ-54428 (MC-02,479), a new cephalosporin active against resistant gram-positive bacteria. J Antibiot (Tokyo). 2000 Nov;53(11):1272-81. doi: 10.7164/antibiotics.53.1272. PMID: 11213288. 13: Cho A, Glinka TW, Ludwikow M, Fan AT, Wang M, Hecker SJ. New anti-MRSA cephalosporins with a basic aminopyridine at the C-7 position. Bioorg Med Chem Lett. 2001 Jan 22;11(2):137-40. doi: 10.1016/s0960-894x(00)00603-x. PMID: 11206444. 14: Glinka TW, Cho A, Zhang ZJ, Ludwikow M, Griffith D, Huie K, Hecker SJ, Dudley MN, Lee VJ, Chamberland S. SAR studies of anti-MRSA non-zwitterionic 3-heteroarylthiocephems. J Antibiot (Tokyo). 2000 Oct;53(10):1045-52. doi: 10.7164/antibiotics.53.1045. PMID: 11132949. 15: Lee VJ, Hecker SJ. Antibiotic resistance versus small molecules, the chemical evolution. Med Res Rev. 1999 Nov;19(6):521-42. doi: 10.1002/(sici)1098-1128(199911)19:6<521::aid-med4>3.0.co;2-9. PMID: 10557368.

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