DESCRIPTION

Antibacterials interfering with ... 

• antibacterial interfering with cell-wall biosynthesis (absent in cell wall-less Bacteria and L forms) : bactericidal
  • nicotinic acid derivatives
    • isoniazid / isoniazide (INH) or isonicotinic acid hydrazide (Nydrazid^®, ...) is activated by a mycobacterial peroxidase enzyme and inhibits pyridoxal phosphorylation to vitamin B₆ (Mycobacteria cells contain low levels of such a kinase) : so pyridoxine-dependent reactions are inhibited (e.g. enoyl-ACP reductase of fatty acid synthase (FAS) II, which converts D²-unsaturated to saturated fatty acids on the pathway to mycolic acid biosynthesis). It should be co-administered with vitamin B₆ / pyridoxine to minimize adverse side effects from from pyridoxal kinase inhibition.
    • ethionamide (Trecator-SC^®) inhibits the acetylation of isoniazid in vitro.
    • prothionamide
    • pyrazinamide (PZA) (pyrazine analog of nicotinamide) inhibits mycobacterial fatty acid synthase (FAS) I, involved in mycolic acid biosynthesis.
  • D-ethambutol hydrochloride (Myambutol^®). It blocks arabinosyl transferases involved in synthesis of lipoarabinomannan (LAM) and mycolic acids. It is the only chemotherapeutical effective on Mycobacterium marinum.
  • lipopeptides
    • acid lipopeptides inhibit LTA synthesis
      • daptomycin
  • riminophenazines
    • B663 / clofazimine / clofazamine (Lamprene^®) inhibits Na⁺/K⁺ ATPase and acts as an immunosuppressor
    • B669
  • b-lactams :
    • penicillins : tetrahydrothiazole-containing (penem group) compounds that irreversibly inhibit the transpeptidase activity of penicillin-binding protein (PBP) 3.
      • natural penicillins(Gram +ve Bacteria and Neisseria gonorrhoeae). Resistance to penicillin today occurs in as many as 80% of all strains of Staphylococcus aureus : surprisingly, Streptococcus pyogenes has never fully developed resistance to penicillin !
        Side effect : drug-triggered pemphigus
      • biosynthetic penicillins (a-aryloxyalkylpenicillins)
        • pheneticillin
        • propicillin
        • fenbenicillin
        • chlomethocillin
        • azidocillin (acid-resistant => PO)
      • semisynthetic penicillins (Gram -ve rods). A mold produces the main part of the molecule (6-aminopenicillanic acid) which can be modified chemically by the addition of side shains. Resistant to b-lactamase.
        • dihydropenicillin F
        • a-aminopenicillins
          • amoxicillin
          • ampicillin (Omnipen^®, Polycillin^®, ...) is effective orally (prodrugs : bacampicillin, etacillin, pivampicillin, talampicillin and metampicillin)
          • cyclacillin
          • epicillin
          Side effects : Steven-Johnsons's syndrome
        • anti-Pseudomonas aeruginosa penicillins
          • a-carboxypenicillins (decreased effect on Gram +ve)
            • carbenicillin indanyl sodium (Geocillin^®)
            • carfecillin
            • sulbenicillin
            • ticarcillin (Ticar^®)
          • ureidopenicillins or N-acylpenicillins
            • apalcillin
            • azlocillin
            • furbenicillin
            • guanylureidopenicillin
            • mezlocillin sodium (Mezlin^®)
            • piperacillin (Pipracil^®)
            • pirbenicillin
            • thymoxycillin
        • a-sulphoxypenicillins
          • sulbenicillin
          • suncillin
        • b-lactamase resistant penicillins
          • isoxazolpenicillins
            • cloxacillin
            • dicloxacillin (Pathocil^®, ...)
            • flucloxacillin
            • oxacillin
          • methicillin binds PBP2.
          • nafcillin (Unipen^®, Nallpen^®, ...)
        • 6a-methoxypenicillins (6a-methoxyphenem)
          • temocillin
        • amidinopenicillins
          • mecillinam
          • pivmecillinam
        • amidinopentanoic acids
          • amdinocillin (prodrugs : pivamdinocillin, bacamdinocillin)
      They may cause type I, type II, type III and type IV hypersensitivities.
    • oxacephems (oxacephem group) : effective against Gram +ve and Gram -ve Bacteria, penicillinase-resistant.
      • latamoxef
      • moxalactam
    • cephalosporins (Gram +ve and Gram -ve Bacteria) (from 7-aminocephalosporanic acid). Cephem group. They tend to be resistant to b-lactamases/penicillinases from S. aureus. They bind PBP3.
      • cephalosporin C
      • 1st generation cephalosporins
        • cefacetryl
        • cefadroxil (orally active) (Duricef^®, Ultracef^®)
        • cefalexin / cephalexin (orally active) (Ceforex^®, Keflex^®). Side effect : drug-triggered pemphigus
        • cephaloridine
        • cephalotin (Keflin^®)
        • cephapirin
        • cephatrizin (orally active)
        • cefazolin (Ancef^®, Kefzol^®, Zolicef^®,...)
        • cephradine (orally active)
        • cephtezol
      • 2nd generation cephalosporins (cephamycins)
        • axetil (acetoxyetyl) cefuroxime (Ceftil^®) (b-lactamase resistant)
        • cefachlor (Ceclor^®) (orally active)
        • cefamandole (Mandol^®)
        • cefmetazol
        • cefocinid (Monocid^®)
        • ceforanide (Precef^®)
        • cefotetan (Cefotan^®)
        • cefotiam
        • cefoxitin (Mefoxin^®) (b-lactamase resistant)
        • cefuroxime (Kefurox^®, Zinacef^®)
        • loracarbef (Lorabid^®)
      • 3rd generation cephalosporins
        • cefetamet
        • cefixime (Suprax^®)
        • cefmenoxim
        • cefodizim
        • cefoperazone (Cefobid^®)
        • cefotaxime (Claforan^®)
        • cefpodoxime proxetil (Orelox^®, Vantin^®)
        • cefsulodin
        • ceftazidime (Ceptaz^®, Fortaz^®, Tazidime^®,...)
        • ceftibuten (Cedax^®)
        • ceftizoxime (Cefizox^®)
        • ceftriaxone (Rocephin^®)
        • moxalactam
      • 4th generation cephalosporins (oxacephamycin)
        • cefepime (Maxipime^®)
        • cefetecol
        • cefprirome
      Side effects : Steven-Johnsons's syndrome
    • carbapenems (Gram +ve and Gram -ve Bacteria) (the N atom in the penem group of penicillin is substitued by a C atom => carbopenem group). They arise from modifications of the chemically unstable thienamycin.
      • imipenem / MK 0787 / N-formimidoiyl thienamycin + cilastatin (an inhibitor of dipeptidase I-mediated hydrolysis in proximal renal tubule) (Primaxin^®). As it is a zwitterion it can penetrates the outer membrane in Gram -ve Bacteria. The trans-hydroxyethil side chain differs from the cis-aminoacyl  side chain in penicillins and so this molecule is not a substrate for b-lactamase. It binds PBP a/Ib.
      • meropenem (Merrem IV^®) is a dimethylcarbamoyl pyrodinyl derivative of thienamycin and is not hydrolized by dipeptidase I
      • olivanic acids / olivanates
        • MM4550
        • MM13902
        • MM17880
        • MM22380
        • MM22381
        • MM22382
        • MM22383
    • monocyclic b-lactams / monobactams (aerobic Gram -ve Bacteria)
      • aztreonam (Azactam^®) : penicillinase-resistant, used against Pseudomonas aeruginosa
    • b-lactamase / penicillinase competitive irreversible inhibitors (they are effective only if coupled to a penicillin whose pharmacokinetics is identical) :
      • 6b-iodopenicillanic acid
      • 6b-bromopenicillanic acid
      • olivanic acids / olivanates
      • BRL42715
      • oxapenems
        • clavulanic acid (clavam group) in combination with ...
          • amoxicillin : clavamox (Augmentin^® / Clavucid^®)
          • ticarcillin : co-amoxiclav (Timentin^®)
      • penem sulfones
        • sulbactam, a penicillanic acid sulfone (in combination with ampicillin in Unasyn^®)
        • tazobactam (in combination with piperacillin in TAZ/PIPC or Tazocin^® / Zosyn^®)
  • glycopeptides (heptapeptide-attached sugars) (Gram +ve Bacteria)
    • vancomycin group
      • vancomycin hydrochloride (Lyphocin^®, Vancocin^®, Vancoled^®) inhibits both transglycosylation and transpeptidation reactions during peptidoglycan assembly: it makes 5 hydrogen bonds to the -D-Ala-D-Ala dipeptide terminus of each uncrosslinked peptidoglycan side chain, inhibiting both the transglycosilase and transpeptidase activity of PBPs. Nowadays vancomycin-resistant Enterococci (VRE) and vancomycin-resistant Staphylococcus aureus (VRSA) (MBC > 32 mg/mL) appeared thanks to a plasmid-coded enzyme that creates -D-Ala-D-lactate termini, resulting in the loss of 1 hydrogen bond that significantly reduces the binding constant ! The VanA strains are resistant to both vancomycin and teicoplanin, while the VanB strains are resistant to vancomycin only.
        Side effects : histamine-mediate "red-man syndrome" (anaphylactoid reaction). Cross-resistance to glycopeptides can arise from use of avoparcin as growth promoter in animal feeding.
      • oritavancin / LY333328
    • teicoplanin group : N-methylLeu in 1 and Lys in 3 are replaced by substituted phenylGlys
      • teicoplanin (Targocid^®) (less toxic than vancomycin)
      • ristocetin (it also binds to vWF (which in fact is a.k.a. ristocetin cofactor) causing human platelets aggregation)
      • eremomycin
      • BRL 47761
    • ramoplanin (a glycolipodepsipeptide consisting of 17 amino acids cyclized to a macrolactone) inhibits transpeptidase activity of PBPs
  • fosfomycin trometamol (Monural^®, Monuril^®) (broad spectrum) (from Streptomyces gradiae) inhibits PEP transferase
  • bacitracin zinc (AK-Tracin^®) (Gram +ve Bacteria) needs a divalent cation (Mg²⁺, Zn²⁺, Co²⁺, Ni²⁺ or Cu²⁺) to bind the undecaprenol-P-P and preventing it from being dephosphorylated by a membrane pyrophosphatase. It has a high kidney toxicity which precludes its systemic use. It is present in many topical antibiotic preparations, and since it is not absorbed by the gut, it is given to "sterilize" the bowel prior to surgery.
  • D-cycloserine (Seromycin^®) (Gram -ve and Gram +ve Bacteria) (from Streptomyces orchidaceous) enters bacterial cells by means of an active transport system for Gly and can reach a relatively high intracellular concentration inhibiting Ala racemase and D-Ala-D-Ala synthetase. Side effects : as it is fairly toxic it has limited use as a secondary drug for TBC.
  • spirocyclohexene
  • griseofulvin inhibits microtubule formation in mitotic spindle. It may act as a photosensitizer.
• antibacterial interfering with cell membrane integrity : these antibiotics disorganize the structure or inhibit the function of bacterial membranes. However, due to the similarities in phospholipids in eubacterial and eukaryotic membranes, this action is rarely specific enough to permit these compounds to be used systemically.
  • cyclic polypeptides
    • polymyxin. Effective mainly against Gram -ve Bacteria : usage is usually limited to topical usage and is occasionally given for UTIs caused by Pseudomonas strains that are gentamicin-, carbenicillin- and tobramycin-resistant. The balance between effectiveness and damage to the kidney and other organs is dangerously close, and the drug should only be given under close supervision in the hospital.
      • polymixin B sulfate (a mixture of polymixin B₁ and B₂) binds lipid A
      • polymixin E / colistin (bactericidal) from Aerobacillus colistinus
    • tyrothricin
  • polyene : inhibits sterols present in cell wall-less Bacteria, but they are mainly used as antifungal agents.
• antibacterial interfering with protein synthesis
  • impairing 50S subunit => prevents translation => bacteriostatic
    • oligosaccharides
      • evernimomycin / evernimoicin / evernimycin / SCH27899 (Ziradin^®)
    • macrolides (against most Bacteria ; bactericidal for a few Gram +ve Bacteria) : macrocylic (12÷22 carbon atoms) lactones linked through glycoside bonds with amino sugars. Binding to the rRNA 23S (P8 protein ?) in the 50S ribosomal subunit inhibits elongation of the protein by peptidyl transferase or prevents translocation of the ribosome or both.
      • clarithromycin (Biaxin Filmtabs^®, Biaxin XL Filmtabs^®, Biaxin^®) : agonist on MTLR1.
      • dirithromycin
      • fluritromicin
      • midecamicin
      • rokitamycin
      • troleandomicin
      • siomycin / thiostrepton
      • 14 carbons
        • erythromycin base (E-Mycin^®, Ilotycin^®,  ...), estolate (Ilosone^®), gluceptate (Ilotycin Gluceptate^®), ethylsuccinate (E.E.S.^®, ...) or lactobionate (Erythrocyn Lactobionate-I.V.^®) ; Benzamycin^®, Persa-Gel^®, ... in combination with benzoyl peroxide. From Streptomyces erythreus : not effective against Enterobacteriaceae. Bactericidal in vitro at high concentrations.
          Side effect : vomiting due to action as agonist on MTLR1 (33%)
          
        • oleandomycin : agonist on MTLR1.
        • roxithromycin
      • 15 carbons
        • azithromycin (Zithromax^®) : agonist on MTLR1.
      • 16 carbons
        • josamycin
        • miocamycin
        • rosaramycin
        • spiramycin
      Cross-resistance to macrolides can arise from use of tylosin and virginiamycin as additives in animal feeding.
    • ketolides (a 3-keto group replaces L-cladinose group of macrolides)
      • telithromycin
    • lincosamides
      • lincomycin hydrocloride
      • clindamycin (Cleocin^®) pediatric (Cleocin Pediatric^®), topical (Cleocin T^®) or topical phosphate (Cleocin Phosphate^®, Actiza^®) is 7-chloro-7-deoxylincomycin, effective against Gram +ve Bacteria and Gram -ve Neisseria, Hemophilus influenzae, Bacteroides spp.). Velac^® in combination with tretinoin.
      Cross-resistance to lincosamides can arise from use of tylosin and virginiamycin as additives in animal feeding.
    • streptogramins bind 50S impairing both early peptide chain elongation and late peptide chain extrusion => bacteriostatic. They are a mix of :
      • A (macrolide)
        • dalfopristin
      • B (cyclic peptide)
        • quinupristin
      • pristinamycin = quinupristin + dalfopristin (Q/D) (Synercid^®) : they are semisynthetic derivatives of pristinamycins.
      Cross-resistance to streptogramins can arise from use of tylosin and virginiamycin as additives in animal feeding.
    • fusidic acid (against Gram +ve Bacteria; bactericidal in vitro at high concentrations) (from Fusidium coccineum) inhibits EF-G
    • ramycin inhibits EF-G
    • viomycin
    • phenicols : effective against Gram +ve and Gram -ve cocchi and Salmonella typhi
      • chloramphenicol (currently it is produced entirely by chemical synthesis) (AK-Chlor^®, Chloromycetin^®, Chloroptic^®, Ocu-Chlor^®) inhibits the bacterial enzyme peptidyl transferase in the 50S subunit. Since mitochondria probably originated from prokaryotic cells and have 70S ribosomes, they are subject to inhibition. The eukaryotic cells most likely to be inhibited by chloramphenicol are those undergoing rapid multiplication, thereby rapidly multiplying mitochondria. Such cells include the blood forming cells of the bone marrow, the inhibition of which could present as dose-related acquired aplastic anemia in 1:50,000. In newborns it may cause gray-baby syndrome due to inadequate glucuronidation with drug accumulation. Now it is seldom used in human medicine except in life-threatening situations (e.g. typhoid fever). R plasmid encoded resistance gene = CAT (chloramphenicol acetyltransferase). The only antimicrobial whose enteric absorption (palmitate) is better than parenteral absorption (succinate).
      • tiamphenicol
  • impairing 30S subunit => wrong translation => toxic alterated proteins => bactericidal
    • tetracyclines (bacteriostatic) : products of the aromatic poliketide biosynthetic pathway in Streptomyces, act by binding the 30S subunit and blocking the binding of aminoacyl tRNA to the A site on the ribosome. As most Bacteria possess an active transport system for tetracycline that allows intracellular accumulation of the antibiotic at concentrations 50 times as great as that in the medium, a blood level which is harmless to animal tissues can halt protein synthesis in invading Bacteria.
      • chlortetracycline (Aureomycin^®)
      • demeclocycline (Declomycin^®)
      • doxycyclin (Doryx^®, Vibramycin^®, ...) does not cause the photosensitizing reaction that may occur with conventional tetracycline. Divalent cations, gluten products, and calcium do not materially interfere with its absorption. Since doxycycline is a highly lipid-soluble antimicrobial, a loading dose is necessary for optimal results. Therefore, for moderate or severe infections, the usual dose, given intravenously or orally, should be doubled for 72 hours and then reduced to the usual dose (ie, 200 mg every 12 hours reduced to 100 mg every 12 hours). The entire dose (intravenous or oral) may be given once daily. Doxycycline should be taken with food and should not be given to pregnant patients or young children
      • lymecycline (Tetralysal^®)
      • meclocycline
      • minocycline (Minocin^®, ...) is 10-folds more lipid-soluble than conventional tetracycline whereas doxycycline is only 5-folds more lipid-soluble. The clinical importance of this characteristic is that minocycline has particularly good tissue penetration and excellent CNS penetration. It is effective also against MRSA. Food and divalent cations interfere minimally or not at all with oral absorption, and photosensitizing reactions are rare. Because of its high lipid-solubility, the drug is maintained in high concentrations in middle ear fluid; thus, it has been implicated in vestibular side effects. It should not be given to pregnant patients or young children.
      • oxytetracycline (Terramycin^®, ...)
      • rolitetracycline
      • tetracycline (Achromycin^®, ...)
      Some newly discovered members of the tetracycline family (e.g. chelocardin) have been shown to act by inserting into the bacterial membrane, not by inhibiting protein synthesis.
      Side effects : renal toxicity (75%), hepatotoxicity, neurotoxicity, arterial hypertension, hirsutism, gingival hyperplasia, GI toxicity, Steven-Johnsons's syndrome
    • glycylcyclines are tetracycline derivatives
      • tigecycline / GAR936
    • aminoglycosides (against Gram -ve Bacteria and just a little Gram +ve Bacteria). They bind to the S12 (a.k.a. P10) protein in the 30S subunit of the bacterial ribosome blocking the binding of initiator N-fMet- tRNA^Met to the ribosome and preventing the normal dissociation of ribosomes into their subunits, leaving them mainly in their 70S form, impairing polysomes formation. The difference in spelling (-micin or -mycin) reflects the isolation from Streptomyces spp. or Micromonospora spp., respectively. They can be classified according to their aminocyclitol :
      • streptidin-containing
        • streptomycin : restricted spectrum, but effective even against Mycobacterium tuberculosis
      • 2-deoxystreptamine-containing
        • gentamicin sulfate (Gentalyn^®, Garamycin^®, Genoptic^®, Gent-AK^®, Gentacidin^®, ...) : broad spectrum
        • only topical PO use before GI tract surgery (no if hemorrhages are suspected !) : very toxic when administered IV !
          • kanamycin sulfate (Kantrex^®) : restricted spectrum, but if given IV it is effective even against Staphyloccous aureus
          • intermediate spectrum
            • neomycin sulfate (Mycifradin^®; Neosporin G.U. Irrigant^® in combination with polymixin B)
            • paramomicin : effective even against Staphyloccous aureus
      • broad spectrum
        • amikacin (Amikin^®)
        • netilmicin (Netromycin^®) : semisynthetic
        • sisomicin
        • tobramycin (Aktob^®, Tobral^®, Tobrex^®, Nebcin^®)
      • bekanamycin
      • framicetin (topical use)
      • isepamicin
      • ribostamicin
      • bacteriostatic
        • kasugamicin
        • spectinomycin
      Resistance genes : aminoglycoside acetylases (AAC), adenylylases (AAD), and phosphorylases (APH).
      Side effects :
      • reversible kidney failure lasting up to 20 days after suspension (evaluate [Ala-aminopeptidase]_urine]
      • damage to the vestibulocochleary (auditory) nerves => permanent deafness and/or temporaneous dizziness lasting 2-6 months.
    • oxazolidinones inhibit the bacterial pre-translational initiation complex formation => bacteriostatic
      • linezolid (Zyvox^®)
      • AZD2563
  • mupirocin (Bactroban^®) inhibits Ile-tRNA synthetase
  • puromycin
  • sparsomicin
  • pulvomicin
  • kirromicin
  • methenamine mandelate and hippurate (Urex^®, Hiprex^®) : the compound decomposes in water at acidic pH according to the following reaction :
    NH₄(CH₂)₆ + 6H₂O + 4H⁺ => 4NH₄⁺ + 6HCHO
  • nitrofurans
    • nifurfolin
    • nifuroxazide
    • nifuroxima
    • nifurzide
    • nitrofurantoin (Furadantin^®, Macrobid^®, ...)
• antibacterial interfering with DNA replication and repair
  • clofazimine (Lamprene^®) preferentially binds to GC-rich mycobacterial DNA.
  • metronidazole / 1-(2-hydroxyethyl)-2-methyl-5-nitroimidazole (bactericidal) (Flagyl^®, Metrocream^®, Metrogel^®, Noritate^®, Protostat^®)
  • quinolones (bactericidal against Gram -ve Bacteria) at low doses inhibit the religation of the doubly cleaved DNA whose 5' ends are tethered on 2 Tyr residues in type II bacterial topoisomerases [both DNA gyrase (1 Tyr per GyrA subunit in the active (GyrA)₂(GyrB)₂ tetramer) and topoisomerase IV], while at high doses (e.g. those present in urine) inhibit N-methyltransferase.
    • 1^st generation quinolones : urinary antiseptic, uneffective against Pseudomonas aeruginosa
      • nalidixic acid (Neggram^®). Side effects : Steven-Johnsons's syndrome
      • oxolinic acid
      • piromidic acid
    • 2^nd generation quinolones : urinary antiseptic, effective even against Pseudomonas aeruginosa
      • cinoxacin (Cinobac^®)
      • flumequine
      • novobiocin binds the B subunit of DNA gyrase inhibiting ATP hydrolysis
      • pipemidic acid
      • rosoxacin
    • 3^rd generation / 6-fluoroquinolones (FQ) : systemic distribution (expecially used against bacterial respiratory and UTIs, prostatitis, osteomyelitis, and Salmonella typhi).
      • broad spectrum
        • enoxacin (Penetrex^®)
        • norfloxacin (Chibroxin^®, Noroxin^®, Utinor^®)
      • very broad spectrum
        • ciprofloxacin (Ciloxan^®, Cipro^®, Ciproxin^®) : PO
        • ofloxacin (Floxin^®, Ocuflox^®, Tarivid^®)
      • long-acting (1 / die) and broad spectrum
        • fleroxacin
        • lomefloxacin (Maxaquin^®)
        • pefloxacin
        • temafloxacin
        • uvofloxacin
      • clinafloxacin
      • difloxacin
      • gatifloxacin (Tequin^®)
      • grepafloxacin (Raxar^®)
      • levofloxacin (Levaquin^®)
      • moxifloxacin (Alelox^®)
      • rufloxacin
      • sparfloxacin (Zagam^®)
      • tosufloxacin
      • trovafloxacin (Trovan^®)
      Side effects :
      • fluoride causes cartilage alterations (use is forbidden during pregnancy and in children) => bilateral acute or chronic Achilles calcaneal tendinitis => tendon rupture, more common in patients over 60 years of age. The latency period between the start of treatment and the appearance of the first symptoms range from 1 to 510 days with a median of 6 days. Most patients recover within 2 months after cessation of therapy, but 26% have not yet recovered at followup.
      • relapse in patients who suffered juvenile epilepsy
      • photosensitivity (use sunglasses)
      • neurologic impairment
      • nausea and vomiting
• antibacterial interfering with transcription
  • ansamycins (bactericidal) inhibit RNA polymerase
    • rifamycins (RIF)
      • rifampin (Rifadin^®, Rimactane^®) is a semisynthetic derivative of rifamycin B active against Gram +ve Bacteria, Mycobacterium tuberculosis and some Gram -ve Bacteria. Rifampicin acts quite specifically against the b subunit of the bacterial RNA polymerase and apparently blocks the entry of the first nucleotide which is necessary to activate the polymerase. It is effective orally and crosses the blood-brain barrier, so it is useful for treatment of bacterial meningitis. Side effect : drug-triggered pemphigus
      • rifabutin (Mycobutin^®)
      • rifapentine
    • streptoovaricins
• xenobiotics interfering with intermediate metabolism (anti-metabolites or growth factor analogs)
  • inhibitors of dihydropteroate synthetase required for the synthesis of tetrahydrofolic acid (THF) as they are structurally similar to p-aminobenzoic acid (PABA).
    • sulfones
      • dapsone / 4,4'-diaminodiphenylsulfone
      • sulfoxone
      Side effects : Steven-Johnsons's syndrome
    • sulfonamides (bacteriostatic). They were introduced as chemotherapeutic agents by Domagk, Mietsch and Klarer in 1935, who showed that one of these compounds (the substituted sulfanilamide
      
      derived from the intracellular degradation of the bacterial stain 4-sulfonamide-2',4'-diaminobenzol or red Prontosil
      
      ) had the effect of curing mice with infections caused by b-hemolytic Streptococcus spp.. Chemical modifications of the compound sulfanilamide gave compounds with even higher and broader antibacterial activity. Bacteria which are almost always sensitive to the sulfonamides include Gram +ve Streptococci (b-hemolytic Streptococci and Streptococcus pneumoniae (even if some Streptococci can assume folate from the environment, bypassing the synthesis blockage)) and Gram -ve Bacteria (E. coli, Neisseria meningitidis). They cross the blood-brain barrier.
      • rapidly absorbed and rapidly eliminated sulfonamides
        • sulfisoxazole diolamine (Gantrisin^®, ...; Pediazole^® in combination with erythromycin ethylsuccinate for otitis media; ? in combination with phenazopyridine for UTIs)
        • sulfamethoxazole
        • sulfadiazine
      • hydrophylic (poorly absorbed) sulfonamides => intestinal antisepticals
        • phtalylsulfacetamide
        • phtalylsulfathiazole
        • sulfasalazine (Azaline^®, Azulfidine^®)
        • sulfoguanidine
      • sulfonamides for topical use
        • sulfacetamide (AK-Sulf^®, Bleph-10^®, Cetamide^®, Isopto Cetamide^®, Klaron^®, Sebizon^®, Sodium Sulamyd^®, Sulf-10^®, ... ; Sulfacet-R^® in combination with sulfur)
        • silver sulfadiazine (Silvadene^®, ...)
        • mafenide (a-amino-p-toluene-sulfonamide) acetate (Sulfamylon^®)
      • long-acting sulfonamides
        • sulfadoxine (Fansidar^® in combination with pyrimethamine)
      • sulfamazole
      • sulfamazone
      • sulfametopirazine
      • sulfametoxypiridazine
      • sulfametrol
      • succinylsulfathiazole
      Side effects : renal and hepatic toxicity (they may cause kernicterus in newborns by displacing bilirubin from plasma proteins in the face of increased bilirubin production from fetal erythrocyte turnover, decreased bilirubin conjugation, acidosis, and decreased blood-brain barrier), agranulocytosis, thrombocytopenia, acquired aplastic anemia, hemolytic anemia in G6PD^- patients, GI toxicity, Steven-Johnsons's syndrome => Lyell's syndrome.
    • p-aminosalicylic acid (PAS) competes with p-aminobenzoic acid (PABA)
      Bacteriostatic effects on Mycobacterium tuberculosis.
    • 2,4-diaminopirimidines
      • bromodiprim
      • pyrimethamine
      • tetroxyprim
  • trimethoprim (TMP) (Trimplex^®, Proloprim^®, ...) (bacteriostatic) inhibits bacterial DHF reductase. It is often administered together with bacteriostatic sulfamethoxazole as co-trimoxazole / cotrimoxazole / TMP/SMX (Bactrim^®, Cotrim^®, Septra^®, ...), becoming bactericidal against Gram -ve Bacteria.
  • albomycin is an analog of ferrichrome, made by some Fungi.
  • adicillin
  • fusafungine
  • magnesium oxide nanoparticles sprays
  • phenazopyridine hydrochloride (Pyridium^®, ...) is an analgesic rather than an antiseptic
  • capreomycin (Capastat sulfate^®) consists of 4 cyclic peptides - capremoycins IA, IB, IIA, and IIB - used against Mycobacterium spp.
  • photodynamic therapy by associating the photosensitizer to polyLys.

CLASSIFICATION

BY FUNCTION

• INHIBITING CELL WALL BIOSYNTHESIS
• DISORGANIZING CELL MEMBRANE INTEGRITY
• PREVENTING PROTEIN SYNTHESIS
• INTERFERING DNA REPRODUCTION AND REPAIR
• BINDING HEREDITARY TRANSCRIPTION
• ANTI-METABOLITE

SUB-CATEGORIES

• INHIBITING CELL WALL BIOSYNTHESIS
• Bacitracin
• beta-Lactams
• D-Cycloserine
• D-Ethambutol
• Fosfomycin
• Glycopeptides
• Griseofulvin
• Lipopeptides
• Nicotinic Acid Derivatives
• Riminophenazines
• Spirocyclohexenes

• DISORGANIZING CELL MEMBRANE INTEGRITY
• Cyclic Polypeptides
• Polyenes

• PREVENTING PROTEIN SYNTHESIS
• Aminoglycosides
• Fusidic Acid
• Glycylcyclines
• Kirromicin
• Lincosamides
• Macrolides
• Methenamine
• Mupirocin
• Nitrofurans
• Oligosaccharides
• Oxazolidinones
• Phenicols
• Pulvomicin
• Puromycin
• Ramycin
• Sparsomicin
• Streptogramins
• Tetracyclines
• Viomycin

• INTERFERING DNA REPRODUCTION AND REPAIR
• Clofazimine
• Metronidazoles
• Quinolones
• Fluoroquinolones

• BINDING HEREDITARY TRANSCRIPTION
• Rifamycins
• Streptoovaricins

• ANTI-METABOLITE
• Adicillin
• Albomycin
• Capreomycin
• Fusafungine
• Inhibitors of Dihydropteroate Synthetase
• Magnesium Oxide Nanoparticles
• Phenazopyridine Hydrochloride
• Photodynamic Therapy
• Trimethoprim

LIST

CLASS

RODUCT

CAS RN

PENICILLINS

CEPHALOSPORINS

1ST GENERATION

Cefacetrile

10206-21-0

Cefacetrile sodium

23239-41-0

66592-87-8

119922-85-9

50370-12-2

Cefalexin

15686-71-2

Cefalexin Monohydrate

23325-78-2

Pivcefalexin Hydrochloride

27726-31-4

Pivcefalexin

63836-75-9

Cefaloglycin

3577-01-3

Cefaloglycin Hydrate

22202-75-1

Deacetylcefaloglycin

3890-34-4

Cefalonium

5575-21-3

Cefaloridine

50-59-9

Cefalotin Sodium

58-71-9

Cefalotin

153-61-7

24356-60-3

21593-23-7

Cefatrizine

51627-14-6

Cefazaflur sodium

52123-49-6

Cefazaflur

Cefazedone

56187-47-4

Cefazedone sodium

63521-15-3

27164-46-1

Cefazolin delta-3-methyl ester

117929-10-9

25953-19-9

Cefradine

38821-53-3

Cefroxadine dihydrate

95615-72-8

Cefroxadine

Ceftezole sodium

41136-22-5

Ceftezole

2ND GENERATION

Cefaclor

53994-73-3

Cefaclor Monohydrate

70356-03-5

58648-57-0

42540-40-9

30034-03-8

34444-01-4

Oxacefamandole

62504-53-4

Carbacefamandole

62284-44-0

Cefonicid sodium

61270-78-8

Cefonicid

Ceforanide

Cefotiam

Cefotiam hexetil

95761-91-4

Cefotiam hexetil hydrochloride

95789-30-3

Cefotiam hydrochloride

66309-69-1

55268-75-2

Cefuroxime axetil

64544-07-6

Cefuroxime lysine

65527-51-7

Cefuroxime pivoxetil

100680-33-9

Cefuroxime sodium

56238-63-2

Cefuzonam

Cefuzonam sodium

82219-81-6

3RD GENERATION

Cefcapene

135889-00-8

Cefcapene pivoxil

105889-45-0

Cefcapene Pivoxil Hydrochloride

147816-23-7

Cefcapene Pivoxil Hydrochloride Monohydrate

Cefdaloxime

80195-36-4

Cefdaloxime Pivoxil

Cefdinir

Cefditoren

104145-95-1

Cefditoren Sodium

Cefditoren Pivoxil

117467-28-4

Cefetamet Pivoxil hydrochloride

111696-23-2

Cefetamet Pivoxyl

65243-33-6

Cefetamet

79350-37-1

214265-67-5

Cefmenoxime Hemihydrochloride

75738-58-8

Cefmenoxime

Cefodizime Disodium

86329-79-5

Cefodizime

Cefoperazone A

73240-07-0

Cefoperazone

Cefotaxime S-oxide

69132-42-9

Benzathine cefotaxime

127627-69-4

Desacetylcefotaxime

66340-28-1

85287-61-2

84880-03-5

Cefpiramide sodium

74849-93-7

Cefpiramide

Cefpodoxime proxetil

87239-81-4

Cefsulodin

78439-02-2

72558-82-8

78439-06-2

Cefteram

82547-58-8

Cefteram pivaloyloxymethyl ester

82547-81-7

Ceftibuten

trans-Ceftibuten

97519-40-9

Ceftiofur

80370-57-6

Ceftiofur hydrochloride

103980-44-5

Ceftiofur sodium

104010-37-9

Desfuroylceftiofur

120882-22-6

Ceftiolene

Ceftizoxime alapivoxil

135821-54-4

Ceftizoxime sodium

68401-82-1

Ceftriaxone disodium hemiheptahydrate

104376-79-6

4TH GENERATION

Cefclidine

Cefepime dihydrochloride

107648-80-6

Cefepime hydrochloride

123171-59-5

Cefepime L-arginine dihydrochloride

143892-90-4

Cefepime

Cefluprenam

116853-25-9

Cefoselis

Cefozopran

Cefpirome sulfate

98753-19-6

Cefpirome

Cefquinome

Cefaclomezine

22561-27-9

Cefaloram

859-07-4

Cefaparole

51627-20-4

Cefcanel

41952-52-7

Cefcanel daloxate

97275-40-6

Cefedrolor

57847-69-5

Cefempidone

103238-57-9

Cefetrizole

65307-12-2

Cefivitril

66474-36-0

Cefmatilen

140128-74-1

Cefmepidium Chloride

107452-79-9

Cefovecin

234096-34-5

Cefovecin sodium

141195-77-9

Cefoxazole

36920-48-6

Cefrotil

52231-20-6

Cefsumide

54818-11-0

Ceftioxide

71048-88-9

Ceftobiprole

209467-52-7

Ceftobiprole Medocaril

376653-43-9

Cefuracetime

39685-31-9

CARBACEPHEMS

76470-66-1

Loracarbef monohydrate

121961-22-6

CEPHAMYCINS

Cefbuperazone sodium

76648-01-6

Cefminox sodium

75498-96-3

69712-56-7

Cefotetan disodium

74356-00-6

33564-30-6

35607-66-0

ORAL CEPHEMS

Cefaclor

53994-73-3

Cefaclor hydrate

70356-03-5

Cefadroxil Monohydrate

Cefadroxil

Cefalexin

Cefaloglycine

Cefatrizine

Cefdaloxime

80195-36-4

Cefdaloxime Pivoxil

Cefdinir

Cefditoren Pivoxil

117467-28-4

Cefditoren

104145-95-1

Cefetamet

Cefetamet Pivoxil

Cefixime

Cefotiam Hexetil Hydrochloride

Cefotiam Hydrochloride

Cefotiam Hexetil

Cefotiam

Cefpodoxime Proxetil

Cefpodoxime

Cefcapene pivoxil

105889-45-0

Cefcapene

135889-00-8

Cefprozil

Cefprozil Monohydrate

Cefradine

Cefroxadine

Cefteram Pivoxil

Ceftibuten

Cefuroxime

55268-75-2

Cefuroxime Axetil

64544-07-6

76470-66-1

Loracarbef monohydrate

121961-22-6

OXACEPHEMS

Flomoxef

Flomoxef Sodium

92823-03-5

Moxalactam disodium

64953-12-4

Latamoxef

CARBAPENEMS

Imipenem / Cilastatin

Imipenem anhydrous

Imipenem

Meropenem

Meropenem trihydrate

Panipenem

Panipenem / betamipron

78110-38-0

58001-44-8

POLYPEPTIDES

GLYCOPEPTIDE

TETRACYCLINES

Doxycycline

Methacycline Hydrochloride

Minocycline

Oxytetracycline

CHLORAMPHENICOLS

AMINOGLYCOSIDES

Amikacin

Arbekacin

Astromicin

Bekanamycin

Dibekacin

Gentamicin

Isepamicin

Kanamycin

Lividomycin

Micronomicin

Netilmicin

Paromomycin

Ribostamycin

Sisomicin

MACROLIDES

Kitasamycin)

Rokitamycin

Roxithromycin

Clarithromycin

FLUOROQUINOLONES

Flumequine

Ciprofloxacin

Enoxacin

Fleroxacin

Levofloxacin

Lomefloxacin

Nadifloxacin

Norfloxacin

Ofloxacin

Pefloxacin

Rufloxacin

Balofloxacin

Gatifloxacin

Grepafloxacin

Pazufloxacin

Sparfloxacin

Temafloxacin

Tosufloxacin

Clinafloxacin

Gemifloxacin

Moxifloxacin

Sitafloxacin

Trovafloxacin

Prulifloxacin

Danofloxacin

Difloxacin

Enrofloxacin

Marbofloxacin

Sarafloxacin

SULFONAMIDE

Mafenide Acetate

Mafenide

Sulfacetamide

Sulfadiazine Silver

Sulfadoxine

Sulfamazone

Sulfamethoxazole

152-47-6

Sulfametrol

Sulfisoxazole

Sulfisoxazole Diolamine

Coumermycin

Enramycin

Fosfomycin

Kasugamycin

Novobiocin

Rifampicin

Spectinomycin