chfarm 2012 suport ab peptid aminoglicozid amfenicoli
TRANSCRIPT
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ANTIBIOTICE GLICOPEPTIDICE
VANCOMICINA VANCOMYCIN (DCI)
Glicopeptid triciclic cu structurã complexã; Streptococcus orientalis
Produse farmaceutice
VANCOMYCIN HYDROCHLORIDE, VANCOCIN
VANCO-TEVA, VANMIXAN, VANCOLED
EDICIN, LYPHOCIN (flc. pulb sterila inj.)
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TEICOPLANIN
Actinoplanes teichomyetius
Structurã, mec. act., spectrul de activitate antibioticã vancomicina
R.a.: rash cutanat (doze mari); reactii alergice; ototoxicitate scãzutã
TARGOCID – flc. inj.
ANTIBIOTICE GLICOPEPTIDICE
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Bacillus subtilis
complex de polipeptide; remarcabilã omogenitate a structurii ciclice
alb-cenusie; caracter bazic sulfati
Nefrotoxicitate accentuatã
Aplicatii locale: conjunctivite, ulcere corneene, piodermite, eczeme,
plãgi traumatice si chirurgicale infectate
ANTIBIOTICE CU STRUCTURA POLIPEPTIDICA
BACITRACINA
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BACITRACINUM
Forme farmaceutice: unguent, pulbere externa, spray, unguent oftalmic
Bacitracinã + neomicinã (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)
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Acid cis-1,2-epoxipropilfosfonic sare cu trometamina
E. coli, S. aureus, Serratia, Klebsiella, Citrobacter, Enterococcus,
Enterobacter spp.;
inhibitor al sintezei peretelui bacterian
Fosfomycin Tromethamine *
PF: MONUROL : (P) sare disodicã
(O) sare de calciu si cu trometamina
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ANTIBIOTICE AMINOGLICOZIDICE
AMINOZIDE, AMINOCICLITOLI
Streptomyces 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, Shigella
Rezistenta bacterianã
Indice terapeutic mic
R adv: ototoxicitate, nefrotoxicitate, reactii alergice
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AMINOGLICOZIDE - Clasificare
aglicon streptidinic STREPTOMICINE
STREPTOMICINA
DIHIDROSTREPTOMICINA
aglicon dezoxistreptaminic
NEOMICINE (Negamicine)
GENTAMICINE
KANAMICINE
TOBRAMICINE (Brulamicina)
PAROMOMICINA
AMIKACINA
NETILMICINA
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Streptomicina *
Aglicon streptidina
streptobiozamina
L-streptoza
N-metil-L-glucozamina
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AMINOGLICOZIDE cu AGLICON STREPTidiNIC
Streptomycinum (dci):
“streptomycini sulfas” (fr X)
Streptomyces griseus, S. bikinensis
PF: SULFAT DE STREPTOMICINA – flac inj (i.m.)
STREPANCIL
STREVITAL
DIHIDROSTREPTOMICINA
“Dihydrostreptomycini sulfas”
-CHO -CH2-OH
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Relatii structura chimica - actiune
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AMINOGLICOZIDE cu AGLICON DEZOXISTREPTAMINIC
NEOMICINE (NEGAMICINE)
A, B, C: NEOMYCINI SULFAS (FR X)
Streptomyces fradiae
Spectru antimicrobian: streptomicinei (bacil Koch, G-)
Activitate antibioticã mai intensã în mediu alcalin
p.o.: infectii digestive cu germeni sensibili (1-2g/zi)
pregãtirea interventiilor pe colon (4 g/zi 2-3 zile)
Extern: neomicinã+ bacitracinã + polimixinã B sulfat + corticosteroizi
(ung, pulb, sol, spray): inf. dermatologice, oculare, ale urechii interne
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R.a.: frecvent reactii alergice (local);
sdr. de malabsorbtie, disbacteriozã sau candidozã intestinalã (O)
P.F.
NEGAMICIN- cp
Neomicinã + bacitracinã
NEGAMICIN B – ung
NEOBASEPT - pulb
BANEOCIN, BIVACYN, ENBECIN
NEOBACIN, SANTADERM
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Neomicinã + corticosteroizi
NEOPREOL – ung (+prednisolon+unturã de peste)
NIDOFLOR – ung (+ nistatin+triamcinolon acetonid)
FLUMETAZON PIVALAT N – ung, cremã
FLUOCINOLON N – ung, cremã
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
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GENTAMICINE GENTAMYCINI SULFAS (FR X)
i.m./ i.v.:
infectii severe sau complicate (pielonefrite, septicemii, endocardite,
inf. respiratorii, articulare, cutanate) cu germeni sensibili
(Ps. aeruginosa, Enterobacter, Serratia, Proteus, Klebsiella);
+ beta-lactamine (carbenicilina/ ticarcilinã/ benzilpenicilinã)
topic: arsuri infectate, inf. osoase, oculare
Cind.: alergie; tratamente de lungã duratã tulpini rezistente
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P.F.
Sol.inj.
GENTAMYCIN, GENTAMICIN, GENTAMED,
GARAMYCIN, GENTOGRAM, GEOMYCINE
Sol/ ung. oftalmice
GENTOSEPT – colir
GARASONE – colir, ottoguttae (+Betametasone)
GENTAGEN, GENTICOL, GENTAMYCIN,
GENTAMICIN SULPHATE, OPHTAGRAM
Prep. dermatologice (ung., cremã) + corticosteroizi
FLUOCINOLON G
DIPROGENTA (betametazon dipropionat)
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KANAMICINE (A) KANAMYCINI SULFAS (FR X)
aplicatii locale
i.m.: util. restrânsã în inf. grave; înlocuitã de gentamicinã
O: sterilizarea preoperatorie a intestinului
Cind.: nefropatii; tratamente de lungã duratãrezistentã microbianã
UNGUENT OFTALMIC CU KANAMICINA 1%
KANAMICINA SULFAT H – ung oftalmic (+hidrocortizon)
UNGUENT OFTALMIC CU KANAMICINA SI HIDROCORTIZON
KANAMICINA- flac.inj.
KANAMYCIN, KANAMICIN, KANTREX, KANAMYTREX
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TOBRAMICINA (BRULAMICINA)
6-dezoxikanamicina B
BRULAMICIN
NEBCIN – pulb sterila inj
TOBRADEX – unguent si suspensie oftalmica (+Dexametazona)
TOBREX, TOBRIN
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DIBEKACINA 3,4 – didezoxi Kanamicina B
DEBEKACYL, ICACINE – solutie injectabila
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AMIKACINA :
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AMIKACINA :
AMIKIN, AMIKOZIT, ORLOBIN
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SISOMICINA :
SISOLLINE – solutie injectabila
NETILMICINA :
NETROMYCIN – sol.inj.
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PAROMOMICINA
PF: HUMATIN – capsule 250 mg
HUMACORT ung. (Cloramfenicol+ Paromomicina + Hidrocortizon)
Fortimicina A : ASTROMICINE
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ISEPAMICINA
ISEPACIN-ISEPALLINE – sol.inj.
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SPECTINOMICINA. SPECTINOMYCIN (DCI)
Streptomyces spectabilis; Aminociclitol
KIRIN flac inj. (doza terap. 2 g Spectinomicin)
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AMFENICOLI/ FENICOLI / ANTIBIOTICE ARILALCHILICE
CHLORAMPHENICOLUM * (FR X)
FR X: 2,2-dicloro-N-[(1R, 2R)-1-hidroxi-2-hidroximetil-1-[(4-nitrofenil)-etil]-acetamida
(+) eritro-cloramfenicol si (+) treo-cloramfenicol;
D-(-)-treo-cloramfenicol= activitate antibiotica maxima
D-(-)-treo-cloramfenicol
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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
Rickettsii
Bactericid: Salmonella typhi, S. paratyphi , Haemophilus influenzae,
Neisseria meningitidis, Streptococcus pneumoniae,
Virusuri mari, spirochete
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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)
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Optimizarea unor proprietati biofarmaceutice
ale Cloramfenicolului
1. Optimizarea gustului amar Esteri cu acizi grasi la grupa alcoolica primara
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•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-CH3
•PALMITOIL GLICOLAT DE CLORAMFENICOL (n=14)
•STEAROIL GLICOLAT DE CLORAMFENICOL (n=16)
R : -CO-CH2-O-CO-(CH2)n-CH3
stabilitatea, conc. serice
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2. Optimizarea solubilitatii in apa Esteri hidrosolubili cu acizi
dicarboxilici
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Analogi structurali ai cloramfenicolului
THIAMPHENICOLUM NO2 -SO2-CH3
THIOPHENICOL
enantiomerul D-(-)-treo activ;
spectru de activitate identic cu cel al Cloramfenicolului
mai solubil, mai putin toxic decit Cloramfenicolul
absenta R.A. anemie aplastica
intensitatea actiunii < Cloramfenicolul; durata de actiune > Cloramfenicolul
(O) 1-1,5 g/zi: infectii cai biliare ; digestive, respiratorii
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Relatii structura chimica – activitate
in seria derivatilor cloramfenicolului
Gruparefunctionala
Modularestructurala
Consecinte /Activitate, toxicitate
-NO2
paraCH3-CO- Cetofenicol A; T
CH3-SO2- Tiamfenicol A; durata actiune
Alte grupari(OH, OR, COOH, NH2, NH-R, NR2, CO-NH2, CN, X, Ar, alchil)
A/ inactivi
Alte pozitii pe nucleularomatic
A
Nucleulbenzenic
Ciclohexil, naftil, ciclopentil, chinolil, furil
A
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Gruparefunctionala
Modularestructurala
Consecinte /Activitate, toxicitate
Ar-1CH-OH Ar-1C=O Cloramfenicona
antifungic
C2-NH-COCHCl2 substituire inactivare
-CO-CH2-N=N+=NAzidamfenicol
Hidrosolubilitatea(colir)
C2-NH-COCHBr2
Bromamfenicol A
CH2-OH esterificare Pro-drug-uri (in vivo, hidroliza enzimatica)
Cloramfenicol
Oxidare, reducere, eliminare
Inactivare