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MedKoo Cat#: 329201 | Name: Cefbuperazone Sodium

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 Sodium
Cefbuperazone Sodium
CAS#76648-01-6 (sodium)

Theoretical Analysis

MedKoo Cat#: 329201

Name: Cefbuperazone Sodium

CAS#: 76648-01-6 (sodium)

Chemical Formula: C22H28N9NaO9S2

Exact Mass: 0.0000

Molecular Weight: 649.63

Elemental Analysis: C, 40.68; H, 4.34; N, 19.41; Na, 3.54; O, 22.17; S, 9.87

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Related CAS #
76610-84-9 (free acid) 76648-01-6 (sodium)
Synonym
Cefbuperazone Sodium; BMY-25182; T-1982; BMY 25182; T 1982; BMY25182; T1982; Keiperazon
IUPAC/Chemical Name
sodium (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-carboxylate
InChi Key
WNJOIIXGSLBJAS-FDVIUCIPSA-M
InChi Code
InChI=1S/C22H29N9O9S2.Na/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);/q;+1/p-1/t10-,12+,19+,22-;/m0./s1
SMILES Code
O=C([C@@H]([C@H](C)O)NC(N1CCN(C(C1=O)=O)CC)=O)N[C@@]2(OC)[C@@H](SCC(CSC3=NN=NN3C)=C4C([O-])=O)N4C2=O.[Na+]
Appearance
Solid powder
Purity
>95% (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
Related CAS# 76648-01-6(Cefbuperazone Sodium) 76610-84-9(Cefbuperazone)

Preparing Stock Solutions

The following data is based on the product molecular weight 649.63 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. PubMed PMID: 27394175. 2: 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. PubMed PMID: 23985950. 3: Kumae T, Saburi Y, Nasu M, Misumi J, Kawata N. Effects of cefbuperazone on the chemiluminescence of human neutrophils. Chemotherapy. 1989;35(4):260-6. PubMed PMID: 2766868. 4: Ji CX, Cui YT, Yang DL, Guo C. (2S,3R)-2-[(4-Ethyl-2,3-dioxopiperazin-1-yl)carbonyl-amino]-3-hydroxy-butyric acid monohydrate. Acta Crystallogr Sect E Struct Rep Online. 2008 Jun 19;64(Pt 7):o1292. doi: 10.1107/S1600536808017832. PubMed PMID: 21202922; PubMed Central PMCID: PMC2961655. 5: Okamoto M, Nakane A, Minagawa T. Host resistance to an intragastric infection with Listeria monocytogenes in mice depends on cellular immunity and intestinal bacterial flora. Infect Immun. 1994 Aug;62(8):3080-5. PubMed PMID: 8039875; PubMed Central PMCID: PMC302930. 6: Saikawa I, Takai A, Nakashima Y, Ikegami T, Hayakawa H, Noguchi M, Yamauchi H, Shimizu H. [Studies on absorption, distribution and excretion of 14C labelled sodium 7 beta-[(2R, 3S)-2-(4-ethyl-2,3-dioxo-1-piperazinecarboxamido)-3-hydroxybutanamido]-7-methoxy- 3-[(1-methyl-1H-tetrazol-5-YL)thiomethyl]-3-cephem-4-carboxylate (14C-T-1982) in mice and rats]. Jpn J Antibiot. 1982 Sep;35(9):2163-73. Japanese. PubMed PMID: 7143717. 7: Saikawa I, Nakashima Y, Tai M, Sakai H, Takakura I, Ikegami T, Hayakawa H, Shugimoto Y, Yamafuji T, Miyaura T, et al. [Pharmacological study of beta-lactam antibiotics (15). Metabolism of sodium 7 beta-[(2R,3S)-2-(4-ethyl-2,3-dioxo-1-piperazinecarboxamido)-3- hydroxybutanamido]-7 alpha-methoxy-3- [1-methyl-1H-tetrazol-5-yl) thiomethyl]-3-cephem-4-carboxylate (T-1982)]. Yakugaku Zasshi. 1983 Apr;103(4):414-25. Japanese. PubMed PMID: 6415264. 8: Takano S, Tai M, Sakai H, Takakura I, Ochiai H, Sugimoto Y, Fukuoka Y, Saikawa I. [Studies on beta-lactam antibiotics for medicinal purpose. XIV. Stability and degradation pattern of sodium 7 beta-[(2R, 3S)-2-(4-ethyl-2, 3-dioxo-1-piperazinecarboxamido)-3-hydroxybutanamido]-7 alpha-methoxy-3-[(1-methyl-1H-tetrazol-5-yl)thiomethyl]-3-cephem-4- carboxylate (T-1982) in aqueous solution]. Yakugaku Zasshi. 1983 Jan;103(1):62-72. Japanese. PubMed PMID: 6864450. 9: Saikawa I, Takai A, Nakashima Y, Ikegami T, Hayakawa H, Noguchi M, Yamauchi H, Shimizu H. [The whole body autoradiographic studies on the distribution of 14C-labelled sodium 7 beta-[(2R, 3S)-2-(4-ethyl-2, 3-dioxo-1-piperazine-carboxamido)-3-hydroxybutanamido]-7 alpha-methoxy-3-[(1-methyl-1H-tetrazol-5-yl)thiomethyl]-3-cephem-4-carboxylate (14C-T-1982) in mice]. Jpn J Antibiot. 1982 Sep;35(9):2159-62. Japanese. PubMed PMID: 7143716. 10: Tai M, Fukuoka Y, Yotsuji A, Kumano K, Takahata M, Mikami H, Yasuda T, Saikawa I, Mitsuhashi S. In vitro and in vivo antibacterial activity of T-1982, a new semisynthetic cephamycin antibiotic. Antimicrob Agents Chemother. 1982 Nov;22(5):728-34. PubMed PMID: 6983861; PubMed Central PMCID: PMC185653.

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