Carbapenem antibiotic
Pharmaceutical compound
Imipenem Clinical data Trade names Primaxin, others AHFS /Drugs.com International Drug Names MedlinePlus a686013 License data Pregnancy Routes of Intramuscular ,intravenous ATC code Legal status Legal status Pharmacokinetic dataProtein binding 20% Metabolism Kidney Eliminationhalf-life 38 minutes (children), 60 minutes (adults) Excretion Urine (70%) Identifiers CAS Number PubChem CID DrugBank ChemSpider UNII KEGG ChEBI ChEMBL PDB ligand CompTox Dashboard (EPA) ECHA InfoCard 100.058.831 Chemical and physical data Formula C 12 H 17 N 3 O 4 S Molar mass −1 3D model (JSmol ) InChI=1S/C12H17N3O4S.H2O/c1-6(16)9-7-4-8(20-3-2-14-5-13)10(12(18)19)15(7)11(9)17;/h5-7,9,16H,2-4H2,1H3,(H2,13,14)(H,18,19);1H2/t6-,7-,9-;/m1./s1
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Imipenem , sold under the brand namePrimaxin among others, is a syntheticβ-lactam antibiotic belonging to thecarbapenems chemical class. developed by Merck scientists Burton Christensen, William Leanza, and Kenneth Wildonger in the mid-1970s.[ 1] β-lactamase enzymes produced by many multiple drug-resistant Gram-negative bacteria,[ 2] [ 3] intravenous injection.
Imipenem was patented in 1975 and approved for medical use in 1985.[ 4] thienamycin , which is produced by the bacteriumStreptomyces cattleya [ 5] aerobic andanaerobic ,Gram-positive andGram-negative bacteria .[ 6]
Imipenem is a therapeutic alternative on theWorld Health Organization's List of Essential Medicines .[ 7]
Spectrum of bacterial susceptibility and resistance [ edit ] Acinetobacter anitratus ,Acinetobacter calcoaceticus Actinomyces odontolyticus ,Aeromonas hydrophila Bacteroides distasonis ,Bacteroides uniformis , andClostridium perfringens Acinetobacter baumannii , someAcinetobacter Bacteroides fragilis Enterococcus faecalis Pseudomonas aeruginosa Stenotrophomonas maltophilia [ 8]
Coadministration with cilastatin [ edit ] Imipenem is rapidly degraded by the renal enzymedehydropeptidase 1 when administered alone, and is almost always coadministered withcilastatin to prevent this inactivation.[ 9]
Commonadverse drug reactions are nausea and vomiting. People who are allergic topenicillin and other β-lactam antibiotics should take caution if taking imipenem, as cross-reactivity rates are high. At high doses, imipenem is seizurogenic.[ 10]
^ U.S. patent 4,194,047 ^ Clissold SP, Todd PA, Campoli-Richards DM (March 1987). "Imipenem/cilastatin. A review of its antibacterial activity, pharmacokinetic properties and therapeutic efficacy".Drugs .33 (3):183– 241.doi :10.2165/00003495-198733030-00001 .PMID 3552595 .S2CID 209144637 . ^ Vardakas KZ, Tansarli GS, Rafailidis PI, Falagas ME (December 2012)."Carbapenems versus alternative antibiotics for the treatment of bacteraemia due to Enterobacteriaceae producing extended-spectrum β-lactamases: a systematic review and meta-analysis" .The Journal of Antimicrobial Chemotherapy .67 (12):2793– 803.doi :10.1093/jac/dks301 PMID 22915465 . ^ Fischer J, Ganellin CR (2006).Analogue-based Drug Discovery ISBN 9783527607495 ^ Kahan FM, Kropp H, Sundelof JG, Birnbaum J (December 1983). "Thienamycin: development of imipenen-cilastatin".The Journal of Antimicrobial Chemotherapy . 12 Suppl D:1– 35.doi :10.1093/jac/12.suppl_d.1 .PMID 6365872 . ^ Kesado T, Hashizume T, Asahi Y (June 1980)."Antibacterial activities of a new stabilized thienamycin, N-formimidoyl thienamycin, in comparison with other antibiotics" .Antimicrobial Agents and Chemotherapy .17 (6):912– 7.doi :10.1128/aac.17.6.912 .PMC 283902 PMID 6931548 . ^ World Health Organization (2025).The selection and use of essential medicines, 2025: WHO Model List of Essential Medicines, 24th list . Geneva: World Health Organization.hdl :10665/382243 ^ "Imipenem spectrum of bacterial susceptibility and Resistance" (PDF) . Archived fromthe original (PDF) on 3 March 2016. Retrieved4 May 2012 .^ "Imipenem-Cilastatin" .LiverTox: Clinical and Research Information on Drug-Induced Liver Injury PMID 31644018 . NBK548708. Retrieved19 March 2020 .{{cite book }}:|website= ignored (help )^ Cannon JP, Lee TA, Clark NM, Setlak P, Grim SA (August 2014)."The risk of seizures among the carbapenems: a meta-analysis" .The Journal of Antimicrobial Chemotherapy .69 (8):2043– 55.doi :10.1093/jac/dku111 PMID 24744302 .
Ionotropic
GABAA Tooltip γ-Aminobutyric acid A receptor Positive modulators (abridged; seehere for a full list): α-EMTBL Alcohols (e.g.,drinking alcohol ,2M2B )Anabolic steroids Avermectins (e.g.,ivermectin )Barbiturates (e.g.,phenobarbital )Benzodiazepines (e.g.,diazepam )Bromide compounds (e.g.,potassium bromide )Carbamates (e.g.,meprobamate )Carbamazepine Chloralose Chlormezanone Clomethiazole Dihydroergolines (e.g.,ergoloid (dihydroergotoxine) )Etazepine Etifoxine Fenamates (e.g.,mefenamic acid )Flavonoids (e.g.,apigenin ,hispidulin )Fluoxetine Flupirtine Imidazoles (e.g.,etomidate )Kava constituents (e.g.,kavain )Lanthanum Loreclezole Monastrol Neuroactive steroids (e.g.,allopregnanolone ,cholesterol ,THDOC )Niacin Niacinamide Nonbenzodiazepines (e.g.,β-carbolines (e.g.,abecarnil ),cyclopyrrolones (e.g.,zopiclone ),imidazopyridines (e.g.,zolpidem ),pyrazolopyrimidines (e.g.,zaleplon ))Norfluoxetine Petrichloral Phenols (e.g.,propofol )Phenytoin Piperidinediones (e.g.,glutethimide )Propanidid Pyrazolopyridines (e.g.,etazolate )Quinazolinones (e.g.,methaqualone )Retigabine (ezogabine) ROD-188 Skullcap constituents (e.g.,baicalin )Stiripentol Sulfonylalkanes (e.g.,sulfonmethane (sulfonal) )Topiramate Valerian constituents (e.g.,valerenic acid )Volatiles /gases (e.g.,chloral hydrate ,chloroform ,diethyl ether ,paraldehyde ,sevoflurane )Negative modulators: 1,3M1B 3M2B 11-Ketoprogesterone 17-Phenylandrostenol α3IA α5IA (LS-193,268) β-CCB β-CCE β-CCM β-CCP β-EMGBL Anabolic steroids Amiloride Anisatin β-Lactams (e.g.,penicillins ,cephalosporins ,carbapenems )Basmisanil Bemegride Bicyclic phosphates (TBPS ,TBPO ,IPTBO )BIDN Bilobalide Bupropion CHEB Chlorophenylsilatrane Cicutoxin Cloflubicyne Cyclothiazide DHEA DHEA-S Dieldrin (+)-DMBB DMCM DMPC EBOB Etbicyphat FG-7142 (ZK-31906) Fiproles (e.g.,fipronil )Flavonoids (e.g.,amentoflavone ,oroxylin A )Flumazenil Fluoroquinolones (e.g.,ciprofloxacin )Flurothyl Furosemide Golexanolone Iomazenil (123 I) IPTBO Isopregnanolone (sepranolone) L-655,708 Laudanosine Lindane MaxiPost Morphine Morphine-3-glucuronide MRK-016 Naloxone Naltrexone Nicardipine Nonsteroidal antiandrogens (e.g.,apalutamide ,bicalutamide ,enzalutamide ,flutamide ,nilutamide )Oenanthotoxin Pentylenetetrazol (pentetrazol) Phenylsilatrane Picrotoxin (i.e.,picrotin ,picrotoxinin anddihydropicrotoxinin )Pregnenolone sulfate Propybicyphat PWZ-029 Radequinil Ro 15-4513 Ro 19-4603 RO4882224 RO4938581 Sarmazenil SCS Suritozole TB-21007 TBOB TBPS TCS-1105 Terbequinil TETS Thujone U-93631 Zinc ZK-93426 GABAA -ρ Tooltip γ-Aminobutyric acid A-rho receptor
Metabotropic
GABAB Tooltip γ-Aminobutyric acid B receptor
