Drug General Information (ID: D0295)
  Drug Name
Ceftolozane
  Drug Type Small molecule
  Drug Synonymous
CEFTOLOZANE; 689293-68-3; UNII-37A4IES95Q; Ceftolozane sulfate; 37A4IES95Q; CXA-101; (6R,7R)-3-[[3-amino-4-(2-aminoethylcarbamoylamino)-2-methylpyrazol-1-ium-1-yl]methyl]-7-[[(2Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(2-carboxypropan-2-yloxyimino)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate; Ceftolozane [USAN:INN]; ceftolozano; ceftolozanum; (6R,7R)-3-([3-Amino-4-(2-aminoethylcarbamoylamino)-2-methylpyrazol-1-ium-1-yl]methyl)-7-([(2Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(2-carboxypropan-2-yloxyimino)acetyl]amino)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate; Ceftolozane (USAN); SCHEMBL14663407; CHEBI:134719; DB09050; D10097; (6R,7R)-3-((5-Amino-4-(((2-aminoethyl)carbamoyl)amino)-1-methyl-1H-pyrazol-2-ium-2- yl)methyl)-7-(((2Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-((1-carboxy-1- methylethoxy)imino)acetyl)amino)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2- carboxylate; (6R,7R)-3-[(5-amino-4-{[(2-aminoethyl)carbamoyl]amino}-1-methyl-1H-pyrazol-2-ium-2-yl)methyl]-7-{[(2Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-{[(2-carboxypropan-2-yl)oxy]imino}acetyl]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate; (6R,7R)-7-((Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(((2-carboxypropan-2-yl)oxy)imino)acetamido)-3-((3-amino-4-(3-(2-aminoethyl)ureido)-2-methyl-1H-pyrazol-2-ium-1-yl)methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate; 5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 3-((4-((((2- aminoethyl)amino)carbonyl)amino)-2,3-dihydro-3-imino-2-methyl-1H-pyrazol-1- yl)methyl)-7-(((2Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-((1-carboxy-1- methylethoxy)imino)acetyl)amino)-8-oxo-, (6R,7R)-; 7-{[(2Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-{[(2-carboxypropan-2-yl)oxy]imino}acetyl]amino}-3-[ (5-amino-4-{[(2-aminoethyl)carbamoyl]amino}-1-methyl-1H-pyrazol-2-ium-2-yl)methyl]-3,4-didehydrocepham-4-carboxylate
    Click to Show/Hide
  Therapeutic Class Cephalosporins/Beta-Lactamase Inhibitors
  Structure Could Not Find 2D Structure
3D Structure 2D Structure
  Formula C23H30N12O8S2
  InChI InChI=1S/C23H30N12O8S2/c1-23(2,20(40)41)43-31-11(15-30-21(26)45-32-15)16(36)29-12-17(37)35-13(19(38)39)9(8-44-18(12)35)6-34-7-10(14(25)33(34)3)28-22(42)27-5-4-24/h7,12,18,25H,4-6,8,24H2,1-3H3,(H7,26,27,28,29,30,32,36,38,39,40,41,42)/b31-11-/t12-,18-/m1/s1
  InChIKey JHFNIHVVXRKLEF-DCZLAGFPSA-N
  Canonical SMILES CC(C)(C(=O)O)O/N=C(/C1=NSC(=N1)N)\\C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)C[N+]4=CC(=C(N4C)N)NC(=O)NCCN)C(=O)[O-]
  External Link
Pubchem ID 53234134

Drug-Drug Interaction Network
  Sunburst Graph
AM001  Affected gastrointestinal absorption
AM003  Affected organization distribution
AM005  Affected excretion pathways
AM006  Pharmacodynamic additive effects
AM007  Pharmacodynamic antagonistic effects
BM002  Altered intestinal flora
BM014  Interference of cell/tissue uptake
BM031  Increased renal excretion (Unspecific)
BM050  Increased risk of bleeding
BM072  Increased risk of nephrotoxicity
BM100  Antagonize the effect of vaccine/toxoid
BM107  Attenuated pharmacological effects (Unspecific)
  Relation Graph
 Full list of drugs interacting with Ceftolozane
      Affected gastrointestinal absorption
   Altered intestinal flora Drug Num:  2
Drug ID
 
Drug Name
Formula Pubchem ID Severity Level Interaction Detail REF
D1094
 
Mycophenolate mofetil
 
C23H31NO7
 
5281078 
Moderate    Inter Info   
[21], [22]
D1095
 
Mycophenolic acid
 
C17H20O6
 
446541 
Moderate    Inter Info   
[21], [22]
      Affected organization distribution
   Interference of cell/tissue uptake Drug Num:  1
Drug ID
 
Drug Name
Formula Pubchem ID Severity Level Interaction Detail REF
D1817
 
Indium In-111 oxyquinoline
 
C27H18InN3O3
 
16685037 
Moderate    Inter Info   
[14]
      Affected excretion pathways
   Increased renal excretion (Unspecific) Drug Num:  4
Drug ID
 
Drug Name
Formula Pubchem ID Severity Level Interaction Detail REF
D0217
 
Bumetanide
 
C17H20N2O5S
 
2471 
Moderate    Inter Info   
[11], [12], [13]
D0613
 
Etacrynic acid
 
C13H12Cl2O4
 
3278 
Moderate    Inter Info   
[11], [12], [13]
D0704
 
Furosemide
 
C12H11ClN2O5S
 
3440 
Moderate    Inter Info   
[11], [12], [13]
D1611
 
Torasemide
 
C16H20N4O3S
 
41781 
Moderate    Inter Info   
[11], [12], [13]
      Pharmacodynamic additive effects
   Increased risk of bleeding Drug Num:  3
Drug ID
 
Drug Name
Formula Pubchem ID Severity Level Interaction Detail REF
D0087
 
Anisindione
 
C16H12O3
 
2197 
Moderate    Inter Info   
[8], [9], [10]
D0481
 
Dicoumarol
 
C19H12O6
 
54676038 
Moderate    Inter Info   
[8], [9], [10]
D1711
 
Warfarin
 
C19H16O4
 
54678486 
Moderate    Inter Info   
[8], [9], [10]
   Increased risk of nephrotoxicity Drug Num:  9
Drug ID
 
Drug Name
Formula Pubchem ID Severity Level Interaction Detail REF
D0056
 
Amikacin
 
C22H43N5O13
 
37768 
Moderate    Inter Info   
[5], [6], [7]
D0057
 
Amikacin (liposome)
 
C22H43N5O13
 
37768 
Moderate    Inter Info   
[5], [6], [7]
D1304
 
Plazomicin
 
C25H48N6O10
 
42613186 
Moderate    Inter Info   
[5], [6], [7]
D0718
 
Gentamicin
 
C21H43N5O7
 
3467 
Moderate    Inter Info   
[5], [6], [7]
D0876
 
Kanamycin
 
C18H36N4O11
 
6032 
Moderate    Inter Info   
[5], [6], [7]
D1120
 
Neomycin
 
C23H46N6O13
 
8378 
Moderate    Inter Info   
[5], [6], [7]
D1126
 
Netilmicin
 
C21H41N5O7
 
441306 
Moderate    Inter Info   
[5], [6], [7]
D1507
 
Streptomycin
 
C21H39N7O12
 
19649 
Moderate    Inter Info   
[5], [6], [7]
D1597
 
Tobramycin
 
C18H37N5O9
 
36294 
Moderate    Inter Info   
[5], [6], [7]
      Pharmacodynamic antagonistic effects
   Antagonize the effect of vaccine/toxoid Drug Num:  2
Drug ID
 
Drug Name
Formula Pubchem ID Severity Level Interaction Detail REF
D1914
 
Typhoid vaccine (live)
 
NA
 
NA
Major    Inter Info   
[1], [2], [3]
D1693
 
Vibrio cholerae CVD 103-HgR strain live antigen (live)
 
NA
 
NA
Major    Inter Info   
[4]
   Attenuated pharmacological effects (Unspecific) Drug Num:  3
Drug ID
 
Drug Name
Formula Pubchem ID Severity Level Interaction Detail REF
D0313
 
Chloramphenicol
 
C11H12Cl2N2O5
 
5959 
Moderate    Inter Info   
[15], [16], [17]
D0606
 
Estradiol
 
C18H24O2
 
5757 
Moderate    Inter Info   
[18], [19], [20]
D0619
 
Ethinylestradiol
 
C20H24O2
 
5991 
Moderate    Inter Info   
[18], [19], [20]
References
1 Cerner Multum, Inc. "UK Summary of Product Characteristics.".
2 UK government "Typhoid.".
3 American Medical Association, Division of Drugs and Toxicology "Drug evaluations annual 1994." Chicago, IL: American Medical Association (1994).
4 Product Information. Vaxchora (cholera vaccine, live). PaxVax, Miami, FL.
5 Engle JE, Drago J, Carlin B, Schoolwerth AC "Letter: Reversible acute renal failure after cephalothin." Ann Intern Med 83 (1975): 232-3. [PMID: 1147461]
6 Kabins SA, Cohen S "Cephalothin serum levels in the azotemic patient." Antimicrob Agents Chemother 10 (1964): 207-14. [PMID: 14287932]
7 Yasuhara H, Kobayashi S, Sakamoto K, Kamijo K "Pharmacokinetics of amikacin and cephalothin in bedridden elderly patients." J Clin Pharmacol 22 (1982): 403-9. [PMID: 7130429]
8 Product Information. Suprax (cefixime). Lupin Pharmaceuticals Inc, Baltimore, MD.
9 Wood T, Johnson K, Naylor S, Weinshilboum R "Cefazolin administration and 2-methyl-1,3,4-thiadiazole-5-thiol in humantissue: possible relationship to hypoprothrombinemia." Drug Metab Dispos 30 (2002): 1123-1128
10 Natelson EA, Brown CH, 3d Bradshaw MW, Alfrey CP, Jr Williams TW, Jr "Influence of cephalosporin antibiotics on blood coagulation and platelet function." Antimicrob Agents Chemother 9 (1976): 91-3
11 Chrysos G, Gargalianos P, Lelekis M, Stefanou J, Kosmidis J "Pharmacokinetic interactions of ceftazidime and frusemide." J Chemother 7 Suppl (1995): 107-10. [PMID: 8904125]
12 Dodds MG, Foord RD "Enhancement by potent diuretics of renal tubular necrosis induced by cephaloridine." Br J Pharmacol 40 (1970): 227-36. [PMID: 5492895]
13 Norrby R, Stenqvist K, Elgefors B "Interaction between cephaloridine and furosemide in man." Scand J Infect Dis 8 (1976): 209-12. [PMID: 968459]
14 Product Information. Indium Oxyquinoline In-111 (indium oxyquinoline In-111). GE Healthcare, Princeton, NJ.
15 Agencia Espaola de Medicamentos y Productos Sanitarios Healthcare "Centro de informacion online de medicamentos de la AEMPS - CIMA."
16 Asmar BI, Prainito M, Dajani AS "Antagonistic effect of chloramphenicol in combination with cefotaxime or ceftriaxone." Antimicrob Agents Chemother 32 (1988): 1375-8
17 Brown TH, Alford RH "Antagonism by chloramphenicol of broad-spectrum beta-lactam antibiotics against Klebsiella pneumoniae." Antimicrob Agents Chemother 25 (1984): 405-7
18 Back DJ, Breckenridge AM, Crawford FE, MacIver M, Orne ML, Rowe PH "Interindividual variation and drug interactions with hormonal steroid contraceptives." Drugs 21 (1981): 46-61. [PMID: 7009137]
19 Barnett ML "Inhibition of oral contraceptive effectiveness by concurrent antibiotic administration." J Periodontol 56 (1985): 18-20. [PMID: 3882930]
20 King VJ "OC failure rates and oral antibiotics." J Fam Pract 45 (1997): 104-5. [PMID: 9267366]
21 Product Information. CellCept (mycophenolate mofetil). Roche Laboratories, Nutley, NJ.
22 Product Information. Myfortic (mycophenolic acid). Novartis Pharmaceuticals, East Hanover, NJ.