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Imipenem/cilastatin

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Revision as of 10:07, 19 January 2011 by Beetstra (talk | contribs) (Script assisted update of identifiers from ChemSpider, CommonChemistry and FDA for the Chem/Drugbox validation project - Updated: ChEMBL.)(diff) ← Previous revision | Latest revision (diff) | Newer revision → (diff) Pharmaceutical compound
Imipenem/cilastatin
Combination of
ImipenemCarbapenem antibiotic
CilastatinDehydropeptidase inhibitor
Clinical data
Routes of
administration
Intravenous, intramuscular
ATC code
Legal status
Legal status
Identifiers
CAS Number
PubChem CID
ChemSpider
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
3D model (JSmol)
SMILES
  • O.O(C)2C(=O)N1C(=C(/C12)SCCNC=N)\C(O)=O.OC(=O)(N)CSCCCC\C=C(/NC(=O)1CC1(C)C)C(O)=O
InChI
  • InChI=1S/C16H26N2O5S.C12H17N3O4S.H2O/c1-16(2)8-10(16)13(19)18-12(15(22)23)6-4-3-5-7-24-9-11(17)14(20)21;1-6(16)9-7-4-8(20-3-2-14-5-13)10(12(18)19)15(7)11(9)17;/h6,10-11H,3-5,7-9,17H2,1-2H3,(H,18,19)(H,20,21)(H,22,23);5-7,9,16H,2-4H2,1H3,(H2,13,14)(H,18,19);1H2/b12-6-;;/t10-,11+;6-,7-,9-;/m11./s1
  • Key:DAYDLKPFBFPKHL-KJWPAVRRSA-N
  (verify)

Imipenem/cilastatin (Primaxin) is a broad spectrum beta-lactam antibiotic containing equal quantities of imipenem and cilastatin. It is related to the penicillin/cephalosporin family of antibiotics but is classified as belonging to the carbapenem class.

Mechanism

It has the ability to kill a wide variety of bacteria. It works by interfering with their ability to form cell walls, and therefore the bacteria break up and die.

  • Doripenem, the active cardiac agent, is rapidly degraded by the renal enzyme dehydropeptidase if administered alone (making it less effective); the metabolites can cause kidney damage.
  • Administration. Primaxin FDA label, Food and Drug Administration. Oct 2006.</ref> It may be less likely to cause an allergic reaction in people who have had an allergic reaction to a penicillin in the past. It is particularly effective against Enterobacter species.

Marketing

Imipenem/cilastatin is marketed by Merck & Co. under the trade names Primaxin , Tienam and Zienam. The combination is also marketed by Ranbaxy Laboratories in India under the brand name Cilanem and by Nucleus as Thilia. Imipenem/cilastatin is marketed by Highnoon Laboratories Ltd. in Pakistan under the trade name Prepenem. Prepenem was launched by Highnoon in May 2007 and was the first generic brand after the research brand Tienam.

References

Antibacterials active on the cell wall and envelope (J01C-J01D)
β-lactams
(inhibit synthesis
of peptidoglycan
layer of bacterial
cell wall by binding
to and inhibiting
PBPs, a group of
D-alanyl-D-alanine
transpeptidases
)
Penicillins (Penams)
Narrow
spectrum
β-lactamase sensitive
(1st generation)
β-lactamase resistant
(2nd generation)
Extended
spectrum
Aminopenicillins (3rd generation)
Carboxypenicillins (4th generation)
Ureidopenicillins (4th generation)
Other
Carbapenems / Penems
Cephems
Cephalosporins
Cephamycins
Carbacephems
1st generation
2nd generation
3rd generation
4th generation
5th generation
Siderophore
Veterinary
Monobactams
β-lactamase inhibitors
Combinations
Polypeptides
Lipopeptides
Other
  • Inhibits PG elongation and crosslinking: Ramoplanin
Intracellular
Other
Category: