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.^[1]^[2] It was marketed in Japan as Tomiporan by Toyama Chemical and as Keiperazon by Kaken Pharmaceuticals.^[3]^[4] 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.^[5]

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.

[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.

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