ChFarm 2012 Suport AB Peptid Aminoglicozid Amfenicoli

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ANTIBIOTICE GLICOPEPTIDICE VANCOMICINAProduse farmaceutice VANCOMYCIN HYDROCHLORIDE, VANCOCIN VANCO-TEVA, VANMIXAN, VANCOLED

VANCOMYCIN (DCI)

Glicopeptid triciclic cu structur complex; Streptococcus orientalis

EDICIN, LYPHOCIN

(flc. pulb sterila inj.)

ANTIBIOTICE GLICOPEPTIDICE TEICOPLANIN

Actinoplanes teichomyetius Structur, mec. act., spectrul de activitate antibiotic vancomicina R.a.: rash cutanat (doze mari); reactii alergice; ototoxicitate sczut TARGOCID flc. inj.

ANTIBIOTICE CU STRUCTURA POLIPEPTIDICA BACITRACINABacillus subtilis

complex de polipeptide; remarcabil omogenitate a structurii ciclicealb-cenusie; caracter bazic sulfati Nefrotoxicitate accentuat Aplicatii locale: conjunctivite, ulcere corneene, piodermite, eczeme, plgi traumatice si chirurgicale infectate

BACITRACINUM Forme farmaceutice: unguent, pulbere externa, spray, unguent oftalmic

Bacitracin + neomicin (negamicin)NEGAMICIN B ung NEOBASEPT pulb BANEOCIN pulb BIVACYN pulb, ung oft, spray ENBECIN ung, spray SANTADERM pulb, ung (OROPIVALONE BACITRACINA compr pt supt (+tixocortol)

Fosfomycin Tromethamine *

Acid cis-1,2-epoxipropilfosfonic sare cu trometaminaE. coli, S. aureus, Serratia, Klebsiella, Citrobacter, Enterococcus, Enterobacter spp.;

inhibitor al sintezei peretelui bacterianPF: MONUROL : (P) sare disodic (O) sare de calciu si cu trometamina

ANTIBIOTICE AMINOGLICOZIDICE AMINOZIDE, AMINOCICLITOLIStreptomyces sp. Structural: aminooze legate glicozidic de un aglicon aminociclitol; de ex. Streptomicina= streptobiozamina + agliconul streptidina Mecanism actiune antimicrobiana: bactericide prin inhibarea sintezei proteice Spectru antimicrobian: Enterobacter, E. coli, Klebsiella, Proteus,

Ps. aeruginosa, Salmonella, Serratia, ShigellaRezistenta bacterian Indice terapeutic mic R adv: ototoxicitate, nefrotoxicitate, reactii alergice

AMINOGLICOZIDE - Clasificare aglicon streptidinic STREPTOMICINE STREPTOMICINA DIHIDROSTREPTOMICINA

aglicon dezoxistreptaminic

NEOMICINE (Negamicine)GENTAMICINE KANAMICINE

TOBRAMICINE (Brulamicina)PAROMOMICINA AMIKACINA NETILMICINA

Streptomicina *

Aglicon streptidina

streptobiozamina

L-streptoza

N-metil-L-glucozamina

AMINOGLICOZIDE cu AGLICON STREPTidiNIC Streptomycinum (dci):

streptomycini sulfas (fr X)Streptomyces griseus, S. bikinensisPF: SULFAT DE STREPTOMICINA flac inj (i.m.) STREPANCIL

STREVITAL

DIHIDROSTREPTOMICINA

Dihydrostreptomycini sulfas-CHO -CH2-OH

Relatii structura chimica - actiune

AMINOGLICOZIDE cu AGLICON DEZOXISTREPTAMINICNEOMICINE (NEGAMICINE) A, B, C: NEOMYCINI SULFAS (FR X) Streptomyces fradiae Spectru antimicrobian: streptomicinei (bacil Koch, G-) Activitate antibiotic mai intens n mediu alcalin p.o.: infectii digestive cu germeni sensibili (1-2g/zi) pregtirea interventiilor pe colon (4 g/zi 2-3 zile)

Extern: neomicin+ bacitracin + polimixin B sulfat + corticosteroizi(ung, pulb, sol, spray): inf. dermatologice, oculare, ale urechii interne

R.a.: frecvent reactii alergice (local); sdr. de malabsorbtie, disbacterioz sau candidoz intestinal (O) P.F.

NEGAMICIN- cp

Neomicin + bacitracin NEGAMICIN B ung NEOBASEPT - pulb BANEOCIN, BIVACYN, ENBECIN NEOBACIN, SANTADERM

Neomicin + corticosteroizi NEOPREOL ung (+prednisolon+untur de peste) NIDOFLOR ung (+ nistatin+triamcinolon acetonid)

FLUMETAZON PIVALAT N ung, cremFLUOCINOLON N ung, crem LOCACORTEN with NEOMYCIN MAXITROL suspensie si ung oftalmice ( + Dexametazona) OPHTAMETASONE N = solutie oculara, otica, nazala (+Betametazona) ANTIBIOPTAL colir (+Cloramfenicol) NEOSPORIN - ung oftalmic ( + polimixin B sulfat + bacitracin zinc) PIMAFUCORT, PANDERM, SEPTOZYL DERMESONE N, SYNALAR N

GENTAMICINEi.m./ i.v.:

GENTAMYCINI SULFAS (FR X)

infectii severe sau complicate (pielonefrite, septicemii, endocardite, inf. respiratorii, articulare, cutanate) cu germeni sensibili (Ps. aeruginosa, Enterobacter, Serratia, Proteus, Klebsiella); + beta-lactamine (carbenicilina/ ticarcilin/ benzilpenicilin) topic: arsuri infectate, inf. osoase, oculare

Cind.: alergie; tratamente de lung durat tulpini rezistente

P.F. Sol.inj. GENTAMYCIN, GENTAMICIN, GENTAMED, GARAMYCIN, GENTOGRAM, GEOMYCINE Sol/ ung. oftalmice

GENTOSEPT colirGARASONE colir, ottoguttae (+Betametasone) GENTAGEN, GENTICOL, GENTAMYCIN, GENTAMICIN SULPHATE, OPHTAGRAM Prep. dermatologice (ung., crem) + corticosteroizi FLUOCINOLON G DIPROGENTA (betametazon dipropionat)

KANAMICINE (A)aplicatii locale

KANAMYCINI SULFAS (FR X)

i.m.: util. restrns n inf. grave; nlocuit de gentamicin O: sterilizarea preoperatorie a intestinului Cind.: nefropatii; tratamente de lung durat rezistent microbian

UNGUENT OFTALMIC CU KANAMICINA 1% KANAMICINA SULFAT H ung oftalmic (+hidrocortizon)

UNGUENT OFTALMIC CU KANAMICINA SI HIDROCORTIZONKANAMICINA- flac.inj. KANAMYCIN, KANAMICIN, KANTREX, KANAMYTREX

TOBRAMICINA (BRULAMICINA)6-dezoxikanamicina B BRULAMICIN NEBCIN pulb sterila inj TOBRADEX unguent si suspensie oftalmica (+Dexametazona) TOBREX, TOBRIN

DIBEKACINA

3,4 didezoxi Kanamicina B

DEBEKACYL, ICACINE solutie injectabila

AMIKACINA :

AMIKACINA :AMIKIN, AMIKOZIT, ORLOBIN

SISOMICINA :SISOLLINE solutie injectabila

NETILMICINA :NETROMYCIN sol.inj.

PAROMOMICINAPF: HUMATIN capsule 250 mg HUMACORT ung. (Cloramfenicol+ Paromomicina + Hidrocortizon)

Fortimicina A : ASTROMICINE

ISEPAMICINAISEPACIN-ISEPALLINE sol.inj.

SPECTINOMICINA. SPECTINOMYCIN (DCI)Streptomyces spectabilis; Aminociclitol

KIRIN flac inj. (doza terap. 2 g Spectinomicin)

AMFENICOLI/ FENICOLI / ANTIBIOTICE ARILALCHILICE CHLORAMPHENICOLUM * (FR X)

FR X: 2,2-dicloro-N-[(1R, 2R)-1-hidroxi-2-hidroximetil1-[(4-nitrofenil)-etil]-acetamida (+) eritro-cloramfenicol si (+) treo-cloramfenicol; D-(-)-treo-cloramfenicol= activitate antibiotica maxima

D-(-)-treo-cloramfenicol

CHLORAMPHENICOLUM (FR X) Spectru antimicrobian larg Bacteriostatic: b. aerobe Gram-pozitive si Gram-negative (stafilococi, streptococi; Bacillus anthracis, Clostridii; E coli) anaerobi i.c. (Bacillus fragilis) Chlamydia, Mycoplasma

RickettsiiBactericid: Salmonella typhi, S. paratyphi , Haemophilus influenzae, Neisseria meningitidis, Streptococcus pneumoniae, Virusuri mari, spirochete

Produse farmaceutice:CLORAMFENICOL draj. 125 mg, 250 mg CLORAMFENICOL HEMISUCCINAT flac. inj. 1 g BERLICETIN compr. 250 mg SIFICETINA colir 0,4% BETABIOPTAL colir (+Betametazona) ANTIBIOPTAL colir (+Neomicina) SOLUTIE AURICULARA CU CLORAMFENICOL SI FLUOCINOLON TRICOMICON ovule (Cloramfenicol+ Metronidazol + Nistatin) HUMACORT ung. (Cloramfenicol+ Paromomicina + Hidrocortizon)

Optimizarea unor proprietati biofarmaceutice ale Cloramfenicolului1. Optimizarea gustului amar Esteri cu acizi grasi la grupa alcoolica primara

PALMITAT DE CLORAMFENICOL R: -CO-(CH2)14-CH3 CLORAMFENICOL PALMITAT suspensie orala biodisponibilitate optima: pulbere amorfa 1-5 mm; cristale aciculare < 10 mm STEARAT DE CLORAMFENICOL

R: -CO-(CH2)16-CH3PALMITOIL GLICOLAT DE CLORAMFENICOL (n=14) STEAROIL GLICOLAT DE CLORAMFENICOL (n=16) R : -CO-CH2-O-CO-(CH2)n-CH3 stabilitatea, conc. serice

2. Optimizarea solubilitatii in apa Esteri hidrosolubili cu acizi dicarboxilici

Analogi structurali ai cloramfenicolului THIAMPHENICOLUM THIOPHENICOL NO2 -SO2-CH3

enantiomerul D-(-)-treo activ; spectru de activitate identic cu cel al Cloramfenicolului

mai solubil, mai putin toxic decit Cloramfenicolulabsenta R.A. anemie aplastica intensitatea actiunii < Cloramfenicolul; durata de actiune > Cloramfenicolul (O) 1-1,5 g/zi: infectii cai biliare ; digestive, respiratorii

Relatii structura chimica activitate

in seria derivatilor cloramfenicoluluiGrupare functionala -NO2 Modulare structurala CH3-COCetofenicol Consecinte / Activitate, toxicitate A; T

paraCH3-SO2Tiamfenicol A; durata actiune A/ inactivi Alte grupari (OH, OR, COOH, NH2, NH-R, NR2, CO-NH2, CN, X, Ar, alchil) Alte pozitii pe nucleul aromatic Nucleul benzenic Ciclohexil, naftil, ciclopentil, chinolil, furil

A

A

Grupare functionala Ar-1CH-OH

Modulare structurala Ar-1C=O Cloramfenicona substituire -CO-CH2-N=N+=N Azidamfenicol C2-NH-COCHBr2 Bromamfenicol

Consecinte / Activitate, toxicitate antifungic

C2-NH-COCHCl2

inactivare Hidrosolubilitatea (colir) A

CH2-OH

esterificare

Pro-drug-uri (in vivo, hidroliza enzimatica) Cloramfenicol

Oxidare, reducere, eliminare

Inactivare

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