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MedKoo Cat#: 412501 | Name: Cefbuperazone free acid

Description:

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

Cefbuperazone is a semisynthetic second-generation cephalosporin with antibacterial activity. Cefbuperazone binds to and inactivates penicillin-binding proteins (PBPs) located on the inner membrane of the bacterial cell wall. PBPs are enzymes involved in the terminal stages of assembling the bacterial cell wall and in reshaping the cell wall during growth and division. Inactivation of PBPs interferes with the cross-linkage of peptidoglycan chains necessary for bacterial cell wall strength and rigidity. This results in the weakening of the bacterial cell wall and causes cell lysis.

Chemical Structure

Cefbuperazone free acid
Cefbuperazone free acid
CAS#76610-84-9 (free acid)

Theoretical Analysis

MedKoo Cat#: 412501

Name: Cefbuperazone free acid

CAS#: 76610-84-9 (free acid)

Chemical Formula: C22H29N9O9S2

Exact Mass: 627.1530

Molecular Weight: 627.65

Elemental Analysis: C, 42.10; H, 4.66; N, 20.08; O, 22.94; S, 10.22

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 #
76610-84-9 (free acid) 76648-01-6 (sodium)
Synonym
Cefbuperazone (free acid); Cefbuperazonum; T1982; T-1982; T 1982
IUPAC/Chemical Name
(6R,7S)-7-((2R,3S)-2-(4-ethyl-2,3-dioxopiperazine-1-carboxamido)-3-hydroxybutanamido)-7-methoxy-3-(((1-methyl-1H-tetrazol-5-yl)thio)methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
InChi Key
SMSRCGPDNDCXFR-CYWZMYCQSA-N
InChi Code
InChI=1S/C22H29N9O9S2/c1-5-29-6-7-30(16(35)15(29)34)20(39)23-12(10(2)32)14(33)24-22(40-4)18(38)31-13(17(36)37)11(8-41-19(22)31)9-42-21-25-26-27-28(21)3/h10,12,19,32H,5-9H2,1-4H3,(H,23,39)(H,24,33)(H,36,37)/t10-,12+,19+,22-/m0/s1
SMILES Code
CCN1CCN(C(C1=O)=O)C(N[C@@H](C(N[C@]2([C@H]3SCC(CSc4n(C)nnn4)=C(C(O)=O)N3C2=O)OC)=O)[C@@H](O)C)=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
>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

Preparing Stock Solutions

The following data is based on the product molecular weight 627.65 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: Liu D, Geng T, Wang Y, Ding L. Pharmacokinetic profile of cefbuperazone in healthy Chinese volunteers after single and multiple drip intravenous infusion by HPLC-MS/MS. J Pharm Biomed Anal. 2016 Sep 10;129:28-33. doi: 10.1016/j.jpba.2016.06.029. Epub 2016 Jun 23. PMID: 27394175. 2: Neu HC, Chin NX, Labthavikul P. The activity of cefbuperazone, a 7 alpha- methoxy 7 beta acyl ureido cephalosporin. Chemioterapia. 1985 Dec;4(6):415-23. PMID: 3879464. 3: Prabhala RH, Thadepalli H, Rao B, Bansal MB, Marshall R. In vitro activity of cefbuperazone, a new cephamycin, against anaerobic bacteria. Antimicrob Agents Chemother. 1985 Apr;27(4):640-2. doi: 10.1128/aac.27.4.640. PMID: 4004195; PMCID: PMC180111. 4: Suzuki I, Senda H, Yokota T. In vivo activity of cefbuperazone (T-1982) against various experimental infections in mice. J Antibiot (Tokyo). 1985 Feb;38(2):249-58. doi: 10.7164/antibiotics.38.249. PMID: 3997670. 5: Kameyama J, Tsukamoto M, Asano T, Senda H, Amemiya K, Murakami N, Kaneda N. Experimental studies on the pharmacokinetics and therapeutic effect of cefbuperazone in biliary infection. Curr Med Res Opin. 1989;11(9):577-84. PMID: 2692972. 6: Del Bene VE, Carek PJ, Twitty JA, Burkey LJ. In vitro activity of cefbuperazone compared with that of other new beta-lactam agents against anaerobic gram-negative bacilli and contribution of beta-lactamase to resistance. Antimicrob Agents Chemother. 1985 May;27(5):817-20. doi: 10.1128/aac.27.5.817. PMID: 3874597; PMCID: PMC180158. 7: Kager L, Brismar B, Malmborg AS, Nord CE. Impact of cefbuperazone on the colonic microflora in patients undergoing colorectal surgery. Drugs Exp Clin Res. 1986;12(12):983-6. PMID: 3569009. 8: Inagaki K, Miyamoto Y, Kurata N, Nakane S, Gill MA, Nishida M. Stability of Ranitidine Hydrochloride with Cefazolin Sodium, Cefbuperazone Sodium, Cefoxitin Sodium and Cephalothin Sodium during Simulated Y-Site Administration. Int J Pharm Compd. 2000 Mar-Apr;4(2):150-3. PMID: 23985950. 9: Khan NJ, Bihl JA, Schell RF, LeFrock JL, Weber SJ. Antimicrobial activities of BMY-28142, cefbuperazone, and cefpiramide compared with those of other cephalosporins. Antimicrob Agents Chemother. 1984 Oct;26(4):585-90. doi: 10.1128/aac.26.4.585. PMID: 6549120; PMCID: PMC179970. 10: Shafran SD, Wong J, Chow AW. In vitro activity of Sch 34343 and cefbuperazone against anaerobic bacteria. Antimicrob Agents Chemother. 1985 May;27(5):749-52. doi: 10.1128/aac.27.5.749. PMID: 4015069; PMCID: PMC180146.