Cefbuperazone

Cefbuperazone
Clinical data
Trade names	Tomiporan, Keiperazon
AHFS/Drugs.com	International Drug Names
Routes of; administration	IM, IV
ATC code	J01DC13 (WHO) ;
Legal status
Legal status	In general: ℞ (Prescription only);
Identifiers
	IUPAC name (6R,7S)-7-([(2R,3S)-2-[(4-Ethyl-2,3-dioxopiperazine-1-carbonyl)amino]-3-hydroxybutanoyl]amino)-7-methoxy-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;
CAS Number	76610-84-9 ;
PubChem CID	127527;
ChemSpider	113142 ;
UNII	T0785J3X40;
KEGG	D03423 ;
ChEMBL	ChEMBL1908372 ;
CompTox Dashboard (EPA)	DTXSID701024595 ;
Chemical and physical data
Formula	C22H29N9O9S2
Molar mass	627.65 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCN1CCN(C(=O)C1=O)C(=O)N[C@H]([C@H](C)O)C(=O)N[C@]2([C@@H]3N(C2=O)C(=C(CS3)CSC4=NN=NN4C)C(=O)O)OC;
	InChI 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 ; Key:SMSRCGPDNDCXFR-CYWZMYCQSA-N ;
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Cefbuperazone (INN) is a second-generation cephalosporin antibiotic. It was marketed in Japan as Tomiporan by Toyama Chemical and as Keiperazon by Kaken Pharmaceuticals. In clinical research, cefbuperazone was more effective against B. fragiis and less effective against a variety of anaerobic cocci than other, related cephalosporins, with overall antimicrobial activity being comparable to moxalactam.

References

↑ Izumi K, Kawazoe K, Mikamo H, Ito K, Tamaya T (November 1995). "In vivo bacterial regrowth-inhibition effect of cefbuperazone and amikacin in puerperal uterine cavity". Journal of Chemotherapy. 7 (Suppl 4). Florence, Italy: 173–176. PMID 8904147.
↑ US 4754030, Kaplan MA, Lipper RA, "Cefbuperazone crystalline triethylamine salt", published 1988-06-28, issued 1988-06-28, assigned to Bristol Myers Co
↑ "Cefbuperazone". Inxight Drugs. National Center for Advancing Translational Sciences. Retrieved 2026-08-06.
↑ "Cefbuperazone sodium". ChemicalBook. Retrieved 2026-08-06.
↑ Prabhala RH, Thadepalli H, Rao B, Bansal MB, Marshall R (April 1985). "In vitro activity of cefbuperazone, a new cephamycin, against anaerobic bacteria". Antimicrobial Agents and Chemotherapy. 27 (4): 640–642. doi:10.1128/aac.27.4.640. PMC 180111. PMID 4004195.

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[1] Izumi K, Kawazoe K, Mikamo H, Ito K, Tamaya T (November 1995). "In vivo bacterial regrowth-inhibition effect of cefbuperazone and amikacin in puerperal uterine cavity". Journal of Chemotherapy. 7 (Suppl 4). Florence, Italy: 173–176. PMID 8904147.

[2] US 4754030, Kaplan MA, Lipper RA, "Cefbuperazone crystalline triethylamine salt", published 1988-06-28, issued 1988-06-28, assigned to Bristol Myers Co

[3] "Cefbuperazone". Inxight Drugs. National Center for Advancing Translational Sciences. Retrieved 2026-08-06.

[4] "Cefbuperazone sodium". ChemicalBook. Retrieved 2026-08-06.

[5] Prabhala RH, Thadepalli H, Rao B, Bansal MB, Marshall R (April 1985). "In vitro activity of cefbuperazone, a new cephamycin, against anaerobic bacteria". Antimicrobial Agents and Chemotherapy. 27 (4): 640–642. doi:10.1128/aac.27.4.640. PMC 180111. PMID 4004195.