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MedKoo Cat#: 524585 | Name: Ceftobiprole free base
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Description:

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

Ceftobiprole (free base) is a cephalosporin prodrug. It is used for the treatment of complicated skin and skin-structure infections (cSSSIs) due to methicillin-resistant Staphylococcus aureus (MRSA) and hospital-acquired pneumonia (HAP). Ceftobiprole is designed to bind the penicillin-resistant targets in Gram-positive bacteria, resulting in potent bactericidal activity against methicillin-resistant MRSA and penicillin-resistant Streptococcus pneumoniae (PRSP).

Chemical Structure

Ceftobiprole free base
CAS#209467-52-7 (free base)

Theoretical Analysis

MedKoo Cat#: 524585

Name: Ceftobiprole free base

CAS#: 209467-52-7 (free base)

Chemical Formula: C20H22N8O6S2

Exact Mass: 534.1104

Molecular Weight: 534.57

Elemental Analysis: C, 44.94; H, 4.15; N, 20.96; O, 17.96; S, 12.00

Price and Availability

Size Price Availability Quantity
5mg USD 350.00 2 Weeks
25mg USD 1,250.00 2 Weeks
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Related CAS #
252188-71-9 (medocaril) 209467-52-7 (free base) 376653-43-9
Synonym
Ceftobiprole; AC1OCFF8; Zeftera; UNII-5T97333YZK; BAL-9141; BAL9141; BAL 9141; Ro 63-9141; Ro63-9141;
IUPAC/Chemical Name
(6R,7R)-7-((Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(hydroxyimino)acetamido)-8-oxo-3-((E)-((R)-2-oxo-[1,3'-bipyrrolidin]-3-ylidene)methyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
InChi Key
VOAZJEPQLGBXGO-SDAWRPRTSA-N
InChi Code
InChI=1S/C20H22N8O6S2/c21-20-24-14(26-36-20)11(25-34)15(29)23-12-17(31)28-13(19(32)33)9(7-35-18(12)28)5-8-2-4-27(16(8)30)10-1-3-22-6-10/h5,10,12,18,22,34H,1-4,6-7H2,(H,23,29)(H,32,33)(H2,21,24,26)/b8-5+,25-11-/t10-,12-,18-/m1/s1
SMILES Code
O=C(C(N12)=C(/C=C3C(N([C@H]4CNCC4)CC/3)=O)CS[C@]2([H])[C@H](NC(/C(C5=NSC(N)=N5)=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
Soluble in DMSO, not in water
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 534.57 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: Méndez R, Latorre A, González-Jiménez P. Ceftobiprole medocaril. Rev Esp Quimioter. 2022 Apr;35 Suppl 1(Suppl 1):25-27. doi: 10.37201/req/s01.05.2022. Epub 2022 Apr 22. PMID: 35488820; PMCID: PMC9106187. 2: Martínez Pérez-Crespo PM, López Cortés LE. Ceftobiprole: a clinical view. Rev Esp Quimioter. 2021 Sep;34 Suppl 1(Suppl1):32-34. doi: 10.37201/req/s01.09.2021. Epub 2021 Sep 30. PMID: 34598421; PMCID: PMC8683001. 3: Hsu WH, Hsu CK, Lai CC. Ceftobiprole medocaril for the treatment of pneumonia. Expert Rev Anti Infect Ther. 2023 Jun;21(6):551-563. doi: 10.1080/14787210.2023.2202851. Epub 2023 Apr 18. PMID: 37042813. 4: Lupia T, Pallotto C, Corcione S, Boglione L, De Rosa FG. Ceftobiprole Perspective: Current and Potential Future Indications. Antibiotics (Basel). 2021 Feb 8;10(2):170. doi: 10.3390/antibiotics10020170. PMID: 33567771; PMCID: PMC7915564. 5: Cillóniz C, Dominedò C, Garcia-Vidal C, Torres A. Ceftobiprole for the treatment of pneumonia. Rev Esp Quimioter. 2019 Sep;32 Suppl 3(Suppl 3):17-23. PMID: 31364337; PMCID: PMC6755349. 6: Giacobbe DR, De Rosa FG, Del Bono V, Grossi PA, Pea F, Petrosillo N, Rossolini GM, Tascini C, Tumbarello M, Viale P, Bassetti M. Ceftobiprole: drug evaluation and place in therapy. Expert Rev Anti Infect Ther. 2019 Sep;17(9):689-698. doi: 10.1080/14787210.2019.1667229. Epub 2019 Sep 25. PMID: 31553250. 7: Azanza Perea JR, Sádaba Díaz de Rada B. Ceftobiprole: pharmacokinetics and PK/PD profile. Rev Esp Quimioter. 2019 Sep;32 Suppl 3(Suppl 3):11-16. PMID: 31364336; PMCID: PMC6755345. 8: Falcó V, Burgos J, Almirante B. Ceftobiprole medocaril for the treatment of community-acquired pneumonia. Expert Opin Pharmacother. 2018 Sep;19(13):1503-1509. doi: 10.1080/14656566.2018.1516749. Epub 2018 Sep 10. PMID: 30198789. 9: Scheeren TW. Ceftobiprole medocaril in the treatment of hospital-acquired pneumonia. Future Microbiol. 2015;10(12):1913-28. doi: 10.2217/fmb.15.115. Epub 2015 Nov 17. PMID: 26573022. 10: Ceftobiprole Medocaril: BAL5788, JNJ 30982081, JNJ30982081, RO 65-5788, RO 655788. Drugs R D. 2006;7(5):305-11. doi: 10.2165/00126839-200607050-00003. PMID: 16922591. 11: Grau S. Safety and tolerability of ceftobiprole. Rev Esp Quimioter. 2019 Sep;32 Suppl 3(Suppl 3):34-36. PMID: 31364340; PMCID: PMC6755348. 12: Bassetti M, Mularoni A, Giacobbe DR, Castaldo N, Vena A. New Antibiotics for Hospital-Acquired Pneumonia and Ventilator-Associated Pneumonia. Semin Respir Crit Care Med. 2022 Apr;43(2):280-294. doi: 10.1055/s-0041-1740605. Epub 2022 Jan 27. PMID: 35088403. 13: Liapikou A, Cillóniz C, Torres A. Ceftobiprole for the treatment of pneumonia: a European perspective. Drug Des Devel Ther. 2015 Aug 18;9:4565-72. doi: 10.2147/DDDT.S56616. PMID: 26316697; PMCID: PMC4547641. 14: Zhanel GG, Lam A, Schweizer F, Thomson K, Walkty A, Rubinstein E, Gin AS, Hoban DJ, Noreddin AM, Karlowsky JA. Ceftobiprole: a review of a broad-spectrum and anti-MRSA cephalosporin. Am J Clin Dermatol. 2008;9(4):245-54. doi: 10.2165/00128071-200809040-00004. PMID: 18572975. 15: Syed YY. Ceftobiprole medocaril: a review of its use in patients with hospital- or community-acquired pneumonia. Drugs. 2014 Sep;74(13):1523-42. doi: 10.1007/s40265-014-0273-x. PMID: 25117196. 16: El Solh A. Ceftobiprole: a new broad spectrum cephalosporin. Expert Opin Pharmacother. 2009 Jul;10(10):1675-86. doi: 10.1517/14656560903048967. PMID: 19527192. 17: Del Pozo JL, Patel R. Ceftobiprole medocaril: a new generation beta-lactam. Drugs Today (Barc). 2008 Nov;44(11):801-25. doi: 10.1358/dot.2008.44.11.1264007. PMID: 19180259. 18: Dauner DG, Nelson RE, Taketa DC. Ceftobiprole: A novel, broad-spectrum cephalosporin with activity against methicillin-resistant Staphylococcus aureus. Am J Health Syst Pharm. 2010 Jun 15;67(12):983-93. doi: 10.2146/ajhp090285. PMID: 20516468. 19: Barberán J. Possible clinical indications of ceftobiprole. Rev Esp Quimioter. 2019 Sep;32 Suppl 3(Suppl 3):29-33. PMID: 31364339; PMCID: PMC6755344. 20: Anderson SD, Gums JG. Ceftobiprole: an extended-spectrum anti-methicillin- resistant Staphylococcus aureus cephalosporin. Ann Pharmacother. 2008 Jun;42(6):806-16. doi: 10.1345/aph.1L016. Epub 2008 May 13. PMID: 18477729.