TY  - JOUR
AU  - Vučković, Sonja M.
AU  - Savić-Vujović, Katarina
AU  - Srebro, Dragana
AU  - Ivanović, Milovan
AU  - Došen-Mićović, Ljiljana
AU  - Stojanović, Radan
AU  - Prostran, Milica
PY  - 2012
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/140
AB  - Introduction. Fentanyl belongs to 4-anilidopiperidine class of synthetic opioid analgesics. It is characterized by high potency, rapid onset and short duration of action. A large number of fentanyl analogues have been synthesized so far, both to establish the structure-activity-relationship (SAR) and to find novel, clinically useful analgesic drugs. Objective. In this study, newly synthesized 3-alkyl fentanyl analogues were examined for analgesic activity and compared with fentanyl. Methods. Analgesic activity was assessed by tail-immersion test in rats. Results. The relative potency was: (±)cis-3-methyl fentanyl (8)  gt  (±)trans-3-methyl fentanyl (2) $ (±)cis-3-ethyl fentanyl (1.5)  gt  fentanyl (1) $ (±)trans-3-ethyl fentanyl (0.9)  gt  (±)cis-3-butyl fentanyl (0.064) $ (±)trans-3-butyl fentanyl (0.035)  gt  (±)cis-3-benzyl fentanyl (0.008) $ (±)trans-3-benzyl fentanyl (0.0055). (±)Cis-3-iso-propyl fentanyl, and (±)cis-3-phenethyl fentanyl are inactive in doses up to 5 mg/kg. The duration of action (ED99) was: (±)cis-3-methyl fentanyl (90 min)  gt  (±)trans-3-methyl fentanyl (40 min) # (±)cis-3-ethyl fentanyl (60 min) $ (±)trans-3-ethyl fentanyl (40 min) # fentanyl (50 min) = (±)cis-3-butyl fentanyl (50 min) = (±)trans-3-butyl fentanyl (50 min) = (±)cis-3-benzyl fentanyl (50 min) = (±)trans-3-benzyl fentanyl (50 min). Symbols  gt  and  lt  denotes p lt 0.05. Conclusion. It is concluded that the analgesic potency of 3-alkyl fentanyl analogues is influenced by the steric factor (voluminosity of the group at the position 3 of the piperidine ring and the cis/trans isomerism). Otherwise, with the exception of 3-methyl fentanyl, the duration of action of 3-alkyl fentanyl analogues is not significantly affected by the stereochemistry.
AB  - Uvod. Fentanil pripada grupi sintetskih opioidnih analgetika, 4-anilidopiperidina. Karakteriše ga visoka potentnost, brz početak i kratko trajanje dejstva. Do sada je sintetisan veliki broj analoga fentanila, kako u cilju određivanja odnosa strukture i farmakološke aktivnosti, tako i u cilju pronalaženja novog klinički korisnog analgetika. Cilj rada. U studiji su ispitivana analgetska dejstva novosintetisanih 3-alkil analoga fentanila i poređena sa fentanilom. Metod rada. Merenje analgetskog dejstva ispitivanih jedinjenja vršeno je uz pomoć testa potapanja repa pacova u toplu vodu. Rezultati. Relativna jačina jedinjenja iznosila je: (±)cis-3-metil fentanil (8)  gt  (±)trans-3-metil fentanil (2) $ (±)cis-3-etil fentanil (1,5)  gt  fentanil (1) $ (±)trans-3-etil fentanil (0,9)  gt  (±)cis-3-butil fentanil (0,064) $ (±)trans-3-butil fentanil (0,035)  gt  (±)cis-3-benzil fentanil (0,008) $ (±)trans-3-benzil fentanil (0,0055). (±)Cis-3-izopropil fentanil i (±)cis-3-fenetil fentanil nisu ispoljili dejstvo u dozama do 5 mg/kg. Dužina dejstva (ED99) iznosila je: (±)cis-3-metil fentanil (90 min)  gt  (±)trans-3-metil fentanil (40 min) # (±)cis-3-etil fentanil (60 min) $ (±)trans-3-etil fentanil (40 min) # fentanil (50 min) = (±)cis-3-butil fentanil (50 min) = (±)trans-3-butil fentanil (50 min) = (±)cis-3-benzil fentanil (50 min) = (±)trans-3-benzil fentanil (50 min). Oznake  gt  i  lt  označavaju P lt 0.05. Zaključak Zaključeno je da na analgetsku jačinu 3-alkil analoga fentanila utiče sterni faktor (voluminoznost grupe na položaju 3 piperidinskog prstena i cis/trans izomerizam). Inače, uz izuzetak 3-metil fentanila, stereohemija ne utiče značajno na dužinu dejstva 3-alkil analoga fentanila.
T2  - Engrami
T1  - 3-alkyl fentanyl analogues: Structure-activity-relationship study
T1  - 3-alkil analozi fentanila - studija odnosa strukture i aktivnost
VL  - 34
IS  - 3
SP  - 15
EP  - 26
UR  - https://hdl.handle.net/21.15107/rcub_cherry_140
ER  - 

@article{
author = "Vučković, Sonja M. and Savić-Vujović, Katarina and Srebro, Dragana and Ivanović, Milovan and Došen-Mićović, Ljiljana and Stojanović, Radan and Prostran, Milica",
year = "2012",
abstract = "Introduction. Fentanyl belongs to 4-anilidopiperidine class of synthetic opioid analgesics. It is characterized by high potency, rapid onset and short duration of action. A large number of fentanyl analogues have been synthesized so far, both to establish the structure-activity-relationship (SAR) and to find novel, clinically useful analgesic drugs. Objective. In this study, newly synthesized 3-alkyl fentanyl analogues were examined for analgesic activity and compared with fentanyl. Methods. Analgesic activity was assessed by tail-immersion test in rats. Results. The relative potency was: (±)cis-3-methyl fentanyl (8)  gt  (±)trans-3-methyl fentanyl (2) $ (±)cis-3-ethyl fentanyl (1.5)  gt  fentanyl (1) $ (±)trans-3-ethyl fentanyl (0.9)  gt  (±)cis-3-butyl fentanyl (0.064) $ (±)trans-3-butyl fentanyl (0.035)  gt  (±)cis-3-benzyl fentanyl (0.008) $ (±)trans-3-benzyl fentanyl (0.0055). (±)Cis-3-iso-propyl fentanyl, and (±)cis-3-phenethyl fentanyl are inactive in doses up to 5 mg/kg. The duration of action (ED99) was: (±)cis-3-methyl fentanyl (90 min)  gt  (±)trans-3-methyl fentanyl (40 min) # (±)cis-3-ethyl fentanyl (60 min) $ (±)trans-3-ethyl fentanyl (40 min) # fentanyl (50 min) = (±)cis-3-butyl fentanyl (50 min) = (±)trans-3-butyl fentanyl (50 min) = (±)cis-3-benzyl fentanyl (50 min) = (±)trans-3-benzyl fentanyl (50 min). Symbols  gt  and  lt  denotes p lt 0.05. Conclusion. It is concluded that the analgesic potency of 3-alkyl fentanyl analogues is influenced by the steric factor (voluminosity of the group at the position 3 of the piperidine ring and the cis/trans isomerism). Otherwise, with the exception of 3-methyl fentanyl, the duration of action of 3-alkyl fentanyl analogues is not significantly affected by the stereochemistry., Uvod. Fentanil pripada grupi sintetskih opioidnih analgetika, 4-anilidopiperidina. Karakteriše ga visoka potentnost, brz početak i kratko trajanje dejstva. Do sada je sintetisan veliki broj analoga fentanila, kako u cilju određivanja odnosa strukture i farmakološke aktivnosti, tako i u cilju pronalaženja novog klinički korisnog analgetika. Cilj rada. U studiji su ispitivana analgetska dejstva novosintetisanih 3-alkil analoga fentanila i poređena sa fentanilom. Metod rada. Merenje analgetskog dejstva ispitivanih jedinjenja vršeno je uz pomoć testa potapanja repa pacova u toplu vodu. Rezultati. Relativna jačina jedinjenja iznosila je: (±)cis-3-metil fentanil (8)  gt  (±)trans-3-metil fentanil (2) $ (±)cis-3-etil fentanil (1,5)  gt  fentanil (1) $ (±)trans-3-etil fentanil (0,9)  gt  (±)cis-3-butil fentanil (0,064) $ (±)trans-3-butil fentanil (0,035)  gt  (±)cis-3-benzil fentanil (0,008) $ (±)trans-3-benzil fentanil (0,0055). (±)Cis-3-izopropil fentanil i (±)cis-3-fenetil fentanil nisu ispoljili dejstvo u dozama do 5 mg/kg. Dužina dejstva (ED99) iznosila je: (±)cis-3-metil fentanil (90 min)  gt  (±)trans-3-metil fentanil (40 min) # (±)cis-3-etil fentanil (60 min) $ (±)trans-3-etil fentanil (40 min) # fentanil (50 min) = (±)cis-3-butil fentanil (50 min) = (±)trans-3-butil fentanil (50 min) = (±)cis-3-benzil fentanil (50 min) = (±)trans-3-benzil fentanil (50 min). Oznake  gt  i  lt  označavaju P lt 0.05. Zaključak Zaključeno je da na analgetsku jačinu 3-alkil analoga fentanila utiče sterni faktor (voluminoznost grupe na položaju 3 piperidinskog prstena i cis/trans izomerizam). Inače, uz izuzetak 3-metil fentanila, stereohemija ne utiče značajno na dužinu dejstva 3-alkil analoga fentanila.",
journal = "Engrami",
title = "3-alkyl fentanyl analogues: Structure-activity-relationship study, 3-alkil analozi fentanila - studija odnosa strukture i aktivnost",
volume = "34",
number = "3",
pages = "15-26",
url = "https://hdl.handle.net/21.15107/rcub_cherry_140"
}

Vučković, S. M., Savić-Vujović, K., Srebro, D., Ivanović, M., Došen-Mićović, L., Stojanović, R.,& Prostran, M.. (2012). 3-alkyl fentanyl analogues: Structure-activity-relationship study. in Engrami, 34(3), 15-26.
https://hdl.handle.net/21.15107/rcub_cherry_140

Vučković SM, Savić-Vujović K, Srebro D, Ivanović M, Došen-Mićović L, Stojanović R, Prostran M. 3-alkyl fentanyl analogues: Structure-activity-relationship study. in Engrami. 2012;34(3):15-26.
https://hdl.handle.net/21.15107/rcub_cherry_140 .

Vučković, Sonja M., Savić-Vujović, Katarina, Srebro, Dragana, Ivanović, Milovan, Došen-Mićović, Ljiljana, Stojanović, Radan, Prostran, Milica, "3-alkyl fentanyl analogues: Structure-activity-relationship study" in Engrami, 34, no. 3 (2012):15-26,
https://hdl.handle.net/21.15107/rcub_cherry_140 .

TY  - JOUR
AU  - Sonja, Vuckovic
AU  - Katarina, Savic Vujovic
AU  - Ivanović, Milovan
AU  - Došen-Mićović, Ljiljana
AU  - Todorović, Zoran B.
AU  - Vucetic, C.
AU  - Prostran, M.
PY  - 2012
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/1276
AB  - This study aimed at evaluating the neurotoxicity of fentanyl analogs: (+/-)-cis-3-carbomethoxy fentanyl (C) and (+/-)-trans-3-carbomethoxy fentanyl (T) in rats. C and Tare less potent (2.4-3.1 and 8.4-12.3 times, respectively) than fentanyl (F) in producing both antinociception and morphine-like neurotoxic effects: loss of pinna reflex, Straub tail, impairment of motor coordination, catalepsy, loss of corneal reflex and loss of righting reflex. All of the effects tested were dose-dependent and they were abolished by pretreatment with naloxone, nonselective antagonist of opioid receptors, indicating that they are mediated via opioid receptors. Further, F, C and T exhibited similar relative potencies in producing all tested effects, indicating that similar receptors are involved in producing antinociceptive and neurotoxic effects, most probably of mu type. By using equiantinociceptive doses, C and T produced significantly shorter duration of both antinociception and neurotoxicity than F No significant differences between therapeutic indices for F, C and T were found, indicating that these compounds are equally safe and tolerable in respect to the neurotoxic effects tested. Neurotoxicity testing presented in this paper may be useful in studying the structure-activity relationship of opioid congeners.
AB  - Cilj studije bio je da se ispita neurotoksičnost analoga fentanila: (±)-cis-3-karbometoksi fentanila (C) i (±)-trans-3-karbometoksi fentanil (T) kod pacova. C je oko 2,4-3,1, a T oko 8,4-12,3 puta manje potentan od fentanila u izazivanju antinocicepcije i morfinu-sličnih neurotoksičnih efekata u koje spadaju: refleks ušne školjke, Straub-ov rep, poremećaj motorne koordinacije, katalepsija, gubitak kornealnog refleksa i gubitak refleksa uspravljanja. Svi ispitivani efekti su dozno-zavisni i bivaju poništeni ako se u pretretmanu primeni nalokson, neselektivni antagonist opioidnih receptora, što ukazuje da se efekti odigravaju posredstvom opioidnih receptora. Dalje, F, C i T ispoljavaju sličnu relativnu jačinu u izazivanju ispitivanih efekata, što ukazuje da su slični receptori uključeni u mehanizam antinocicepcije i neurotoksičnih efekata, i to su najverovatnije μ receptori. Kad se primenjuju ekviantinociceptivne doze, C i T izazivaju značajno kraće i antinociceptivno i neurotoksično dejstvo od F. Nisu dokazane značajne razlike u terapijskim indeksima između F, C i T, što ukazuje da su ovi lekovi jednako bezbedni i podnošljivi kad su u pitanju ispitivani neurotoksični efekti. Ispitivanje neurotoksičnosti prikazano u ovom radu može biti korisno u proučavanju odnosa između strukture i aktivnosti hemijski srodnih opioida.
PB  - Veterinary Faculty, Univ Beogradu, Belgrade
T2  - Acta Veterinaria, Beograd
T1  - Neurotoxicity Evaluation of Fentanyl Analogs in Rats
T1  - Ispitivanje neurotoksičnosti analoga fentanila kod pacova
VL  - 62
IS  - 1
SP  - 3
EP  - 15
DO  - 10.2298/AVB1201003V
ER  - 

@article{
author = "Sonja, Vuckovic and Katarina, Savic Vujovic and Ivanović, Milovan and Došen-Mićović, Ljiljana and Todorović, Zoran B. and Vucetic, C. and Prostran, M.",
year = "2012",
abstract = "This study aimed at evaluating the neurotoxicity of fentanyl analogs: (+/-)-cis-3-carbomethoxy fentanyl (C) and (+/-)-trans-3-carbomethoxy fentanyl (T) in rats. C and Tare less potent (2.4-3.1 and 8.4-12.3 times, respectively) than fentanyl (F) in producing both antinociception and morphine-like neurotoxic effects: loss of pinna reflex, Straub tail, impairment of motor coordination, catalepsy, loss of corneal reflex and loss of righting reflex. All of the effects tested were dose-dependent and they were abolished by pretreatment with naloxone, nonselective antagonist of opioid receptors, indicating that they are mediated via opioid receptors. Further, F, C and T exhibited similar relative potencies in producing all tested effects, indicating that similar receptors are involved in producing antinociceptive and neurotoxic effects, most probably of mu type. By using equiantinociceptive doses, C and T produced significantly shorter duration of both antinociception and neurotoxicity than F No significant differences between therapeutic indices for F, C and T were found, indicating that these compounds are equally safe and tolerable in respect to the neurotoxic effects tested. Neurotoxicity testing presented in this paper may be useful in studying the structure-activity relationship of opioid congeners., Cilj studije bio je da se ispita neurotoksičnost analoga fentanila: (±)-cis-3-karbometoksi fentanila (C) i (±)-trans-3-karbometoksi fentanil (T) kod pacova. C je oko 2,4-3,1, a T oko 8,4-12,3 puta manje potentan od fentanila u izazivanju antinocicepcije i morfinu-sličnih neurotoksičnih efekata u koje spadaju: refleks ušne školjke, Straub-ov rep, poremećaj motorne koordinacije, katalepsija, gubitak kornealnog refleksa i gubitak refleksa uspravljanja. Svi ispitivani efekti su dozno-zavisni i bivaju poništeni ako se u pretretmanu primeni nalokson, neselektivni antagonist opioidnih receptora, što ukazuje da se efekti odigravaju posredstvom opioidnih receptora. Dalje, F, C i T ispoljavaju sličnu relativnu jačinu u izazivanju ispitivanih efekata, što ukazuje da su slični receptori uključeni u mehanizam antinocicepcije i neurotoksičnih efekata, i to su najverovatnije μ receptori. Kad se primenjuju ekviantinociceptivne doze, C i T izazivaju značajno kraće i antinociceptivno i neurotoksično dejstvo od F. Nisu dokazane značajne razlike u terapijskim indeksima između F, C i T, što ukazuje da su ovi lekovi jednako bezbedni i podnošljivi kad su u pitanju ispitivani neurotoksični efekti. Ispitivanje neurotoksičnosti prikazano u ovom radu može biti korisno u proučavanju odnosa između strukture i aktivnosti hemijski srodnih opioida.",
publisher = "Veterinary Faculty, Univ Beogradu, Belgrade",
journal = "Acta Veterinaria, Beograd",
title = "Neurotoxicity Evaluation of Fentanyl Analogs in Rats, Ispitivanje neurotoksičnosti analoga fentanila kod pacova",
volume = "62",
number = "1",
pages = "3-15",
doi = "10.2298/AVB1201003V"
}

Sonja, V., Katarina, S. V., Ivanović, M., Došen-Mićović, L., Todorović, Z. B., Vucetic, C.,& Prostran, M.. (2012). Neurotoxicity Evaluation of Fentanyl Analogs in Rats. in Acta Veterinaria, Beograd
Veterinary Faculty, Univ Beogradu, Belgrade., 62(1), 3-15.
https://doi.org/10.2298/AVB1201003V

Sonja V, Katarina SV, Ivanović M, Došen-Mićović L, Todorović ZB, Vucetic C, Prostran M. Neurotoxicity Evaluation of Fentanyl Analogs in Rats. in Acta Veterinaria, Beograd. 2012;62(1):3-15.
doi:10.2298/AVB1201003V .

Sonja, Vuckovic, Katarina, Savic Vujovic, Ivanović, Milovan, Došen-Mićović, Ljiljana, Todorović, Zoran B., Vucetic, C., Prostran, M., "Neurotoxicity Evaluation of Fentanyl Analogs in Rats" in Acta Veterinaria, Beograd, 62, no. 1 (2012):3-15,
https://doi.org/10.2298/AVB1201003V . .

TY  - JOUR
AU  - Dzoljic, E
AU  - Nesic, Z
AU  - Stojanović, R.
AU  - Todorović, Zoran B.
AU  - Vuckovic, S
AU  - Delic, D
AU  - Ivanović, Milovan
AU  - Prostran, M
PY  - 2005
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/744
AB  - Levels of nitric oxide (NO) in the rats frontal cortex were continuously monitored before and after intraperitoneal administration of an antiepileptic drug-pentobarbital (20 and 40 mg/kg) or convulsant drug - pentylenetetrazol (50 mg/kg). Pentobarbital decreased the levels of NO in a dose dependent manner However, NO levels had a tendency to increase following the administration of pentylenetetrazol. It is suggested that central NO participates in the modulation of neuronal excitability, supporting the idea that NO is an important excitatory factor involved in the regulation of seizure susceptibility. Also, our results on anaesthetized rats suggests that endogenous NO may be involved in the mechanism of action of antiepileptic and analeptic drugs and this further suggest that NO levels in the human brain may decrease during antiepileptic therapy and increase during epileptic attacks or administration of excitatory drugs. The aim of the present study was to determine the possible role of NO levels in the brain during neuronal excitability and seizures.
AB  - Nivo azot oksida (NO) u frontalnom korteksu pacova meren je kontinuirano kako pre, tako i nakon intraperitonealne primene antiepileptika pentobarbitala (u dozi od 20 i 40 mg/kg) ili konvulzivnog agensa pentilenetetrazola (u dozi od 50 mg/kg). Rezultati ovih eksperimenta su ukazali da pentobarbital smanjuje nivo NO u frontalnom korteksu pacova, dok koncentracija NO ima tendeciju rasta nakon primene pentilenetetrazola. Osim toga, dokazano je da endogeni NO ima važnu ekscitatornu ulogu u centralnim mehanizmima nastanka epilepsije. Takođe, naši rezultati su ukazali da kod anestetisanih životinja endogeni nivo NO ima uticaja na dejstvo kako antikonvulzivnih, tako i prokonvulzivnih lekova. Nivo NO u mozgu pacova je bio snižen tokom terapije antiepilepticima, a povišen tokom epileptičkih napada ili primene lekova iz grupe centralnih stimulansa.
PB  - De Gruyter Open Ltd, Warsaw
T2  - Acta Veterinaria, Beograd
T1  - Different effects of pentobarbital and pentylenetetrazol on nitric oxide levels in rat frontal cortex
T1  - Uticaj pentobarbitala i pentilenetetrazola na nivo azot oksida u frontalnom korteksu pacova
VL  - 55
IS  - 5-6
SP  - 367
EP  - 374
DO  - 10.2298/AVB0506367D
ER  - 

@article{
author = "Dzoljic, E and Nesic, Z and Stojanović, R. and Todorović, Zoran B. and Vuckovic, S and Delic, D and Ivanović, Milovan and Prostran, M",
year = "2005",
abstract = "Levels of nitric oxide (NO) in the rats frontal cortex were continuously monitored before and after intraperitoneal administration of an antiepileptic drug-pentobarbital (20 and 40 mg/kg) or convulsant drug - pentylenetetrazol (50 mg/kg). Pentobarbital decreased the levels of NO in a dose dependent manner However, NO levels had a tendency to increase following the administration of pentylenetetrazol. It is suggested that central NO participates in the modulation of neuronal excitability, supporting the idea that NO is an important excitatory factor involved in the regulation of seizure susceptibility. Also, our results on anaesthetized rats suggests that endogenous NO may be involved in the mechanism of action of antiepileptic and analeptic drugs and this further suggest that NO levels in the human brain may decrease during antiepileptic therapy and increase during epileptic attacks or administration of excitatory drugs. The aim of the present study was to determine the possible role of NO levels in the brain during neuronal excitability and seizures., Nivo azot oksida (NO) u frontalnom korteksu pacova meren je kontinuirano kako pre, tako i nakon intraperitonealne primene antiepileptika pentobarbitala (u dozi od 20 i 40 mg/kg) ili konvulzivnog agensa pentilenetetrazola (u dozi od 50 mg/kg). Rezultati ovih eksperimenta su ukazali da pentobarbital smanjuje nivo NO u frontalnom korteksu pacova, dok koncentracija NO ima tendeciju rasta nakon primene pentilenetetrazola. Osim toga, dokazano je da endogeni NO ima važnu ekscitatornu ulogu u centralnim mehanizmima nastanka epilepsije. Takođe, naši rezultati su ukazali da kod anestetisanih životinja endogeni nivo NO ima uticaja na dejstvo kako antikonvulzivnih, tako i prokonvulzivnih lekova. Nivo NO u mozgu pacova je bio snižen tokom terapije antiepilepticima, a povišen tokom epileptičkih napada ili primene lekova iz grupe centralnih stimulansa.",
publisher = "De Gruyter Open Ltd, Warsaw",
journal = "Acta Veterinaria, Beograd",
title = "Different effects of pentobarbital and pentylenetetrazol on nitric oxide levels in rat frontal cortex, Uticaj pentobarbitala i pentilenetetrazola na nivo azot oksida u frontalnom korteksu pacova",
volume = "55",
number = "5-6",
pages = "367-374",
doi = "10.2298/AVB0506367D"
}

Dzoljic, E., Nesic, Z., Stojanović, R., Todorović, Z. B., Vuckovic, S., Delic, D., Ivanović, M.,& Prostran, M.. (2005). Different effects of pentobarbital and pentylenetetrazol on nitric oxide levels in rat frontal cortex. in Acta Veterinaria, Beograd
De Gruyter Open Ltd, Warsaw., 55(5-6), 367-374.
https://doi.org/10.2298/AVB0506367D

Dzoljic E, Nesic Z, Stojanović R, Todorović ZB, Vuckovic S, Delic D, Ivanović M, Prostran M. Different effects of pentobarbital and pentylenetetrazol on nitric oxide levels in rat frontal cortex. in Acta Veterinaria, Beograd. 2005;55(5-6):367-374.
doi:10.2298/AVB0506367D .

Dzoljic, E, Nesic, Z, Stojanović, R., Todorović, Zoran B., Vuckovic, S, Delic, D, Ivanović, Milovan, Prostran, M, "Different effects of pentobarbital and pentylenetetrazol on nitric oxide levels in rat frontal cortex" in Acta Veterinaria, Beograd, 55, no. 5-6 (2005):367-374,
https://doi.org/10.2298/AVB0506367D . .

TY  - JOUR
AU  - Vučković, Sonja M.
AU  - Prostran, Milica Š.
AU  - Ivanović, Milovan
AU  - Todorović, Zoran B.
AU  - Stojanović, Radan M.
AU  - Nešić, Zorica I.
AU  - Matić, Ivana
AU  - Milovanović, Slobodan R.
PY  - 2004
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/134
T2  - Vojnosanitetski pregled
T1  - Opioid analgesics [Opioidni analgetici.]
T1  - Opioidni analgetici
VL  - 61
IS  - 4
SP  - 413
EP  - 421
DO  - 10.2298/VSP0404413V
ER  - 

@article{
author = "Vučković, Sonja M. and Prostran, Milica Š. and Ivanović, Milovan and Todorović, Zoran B. and Stojanović, Radan M. and Nešić, Zorica I. and Matić, Ivana and Milovanović, Slobodan R.",
year = "2004",
journal = "Vojnosanitetski pregled",
title = "Opioid analgesics [Opioidni analgetici.], Opioidni analgetici",
volume = "61",
number = "4",
pages = "413-421",
doi = "10.2298/VSP0404413V"
}

Vučković, S. M., Prostran, M. Š., Ivanović, M., Todorović, Z. B., Stojanović, R. M., Nešić, Z. I., Matić, I.,& Milovanović, S. R.. (2004). Opioid analgesics [Opioidni analgetici.]. in Vojnosanitetski pregled, 61(4), 413-421.
https://doi.org/10.2298/VSP0404413V

Vučković SM, Prostran MŠ, Ivanović M, Todorović ZB, Stojanović RM, Nešić ZI, Matić I, Milovanović SR. Opioid analgesics [Opioidni analgetici.]. in Vojnosanitetski pregled. 2004;61(4):413-421.
doi:10.2298/VSP0404413V .

Vučković, Sonja M., Prostran, Milica Š., Ivanović, Milovan, Todorović, Zoran B., Stojanović, Radan M., Nešić, Zorica I., Matić, Ivana, Milovanović, Slobodan R., "Opioid analgesics [Opioidni analgetici.]" in Vojnosanitetski pregled, 61, no. 4 (2004):413-421,
https://doi.org/10.2298/VSP0404413V . .

TY  - CONF
AU  - Vučković, Sonja M.
AU  - Prostran, Milica Š.
AU  - Ivanović, Milovan
AU  - Todorović, Zoran B.
AU  - Stojanović, Radan M.
AU  - Nešić, Zorica I.
PY  - 2002
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/131
C3  - Arhiv za farmaciju
T1  - Analgesic and hyperthermic effects of 3-carbomethoxy fentanyl and 3-butyl fentanyl in rats: Structure-activity relationship
T1  - Analgetički i hipertermni efekti 3-karbometoksi fentanila u pacova: odnos strukture i farmakološke aktivnosti
VL  - 52
IS  - 4
SP  - 626
EP  - 627
UR  - https://hdl.handle.net/21.15107/rcub_cherry_131
ER  - 

@conference{
author = "Vučković, Sonja M. and Prostran, Milica Š. and Ivanović, Milovan and Todorović, Zoran B. and Stojanović, Radan M. and Nešić, Zorica I.",
year = "2002",
journal = "Arhiv za farmaciju",
title = "Analgesic and hyperthermic effects of 3-carbomethoxy fentanyl and 3-butyl fentanyl in rats: Structure-activity relationship, Analgetički i hipertermni efekti 3-karbometoksi fentanila u pacova: odnos strukture i farmakološke aktivnosti",
volume = "52",
number = "4",
pages = "626-627",
url = "https://hdl.handle.net/21.15107/rcub_cherry_131"
}

Vučković, S. M., Prostran, M. Š., Ivanović, M., Todorović, Z. B., Stojanović, R. M.,& Nešić, Z. I.. (2002). Analgesic and hyperthermic effects of 3-carbomethoxy fentanyl and 3-butyl fentanyl in rats: Structure-activity relationship. in Arhiv za farmaciju, 52(4), 626-627.
https://hdl.handle.net/21.15107/rcub_cherry_131

Vučković SM, Prostran MŠ, Ivanović M, Todorović ZB, Stojanović RM, Nešić ZI. Analgesic and hyperthermic effects of 3-carbomethoxy fentanyl and 3-butyl fentanyl in rats: Structure-activity relationship. in Arhiv za farmaciju. 2002;52(4):626-627.
https://hdl.handle.net/21.15107/rcub_cherry_131 .

Vučković, Sonja M., Prostran, Milica Š., Ivanović, Milovan, Todorović, Zoran B., Stojanović, Radan M., Nešić, Zorica I., "Analgesic and hyperthermic effects of 3-carbomethoxy fentanyl and 3-butyl fentanyl in rats: Structure-activity relationship" in Arhiv za farmaciju, 52, no. 4 (2002):626-627,
https://hdl.handle.net/21.15107/rcub_cherry_131 .

TY  - JOUR
AU  - Vučković, Sonja M.
AU  - Prostran, Milica
AU  - Ivanović, Milovan
AU  - Todorović, Zoran B.
AU  - Stojanović, Radan
AU  - Nešić, Zorica
AU  - Matić, Ivana
PY  - 2001
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/139
AB  - Fentanyl, the prototype of the 4-anilidopiperidine class of synthetic opioid analgesics, is widely and successfully used to supplement general anesthesia or to treat postoperative and cancer pain. However, like other m agonists, fentanyl produces serious adverse effects including respiratory depression, muscle rigidity and on prolonged use, tolerance and addiction. In order to discover an analgesic with the improved pharmacodynamic and pharmacokinetic profile, extensive efforts during last four decades have been devoted to synthesis of a large number of fentanyl analogues and establishing the structure-activity-relationship (SAR) of the 4-anilidopiperidine class of analgesics. The objective of SAR studies is to approach the ideal analgesic profile focusing mainly on potency, safety and duration of action. As a result of such efforts, several congeners of fentanyl: alfentanil, sufentanil and remifentanil were discovered and have found clinical use as anesthesia adjuncts. Several other compounds are still under extensive evaluation in animals nowadays, while some of them are proposed as a useful tools in studying the opioid receptors. An interesting SAR obtained with some newly synthesized 3-alkyl fentanyl analogues, as well as 3-carbomethoxy fentanyl (iso-carfentanil) is presented and discussed in this paper. The analgesic potency of 3-carbomethoxy fentanyl is influenced mainly by the steric factor (voluminosity of the carbomethoxy group and the cis/trans isomerism), while the chemical nature of the group is probably irrelevant. In contrast to potency, the duration of action of 3-carbomethoxy fentanyl is most likely influenced by the nature of the carbomethoxy group. Since the potency and the duration of action of this novel analgesic compound are interesting from the aspect of SAR studies, and have potential promise for clinical use, 3-carbomethoxy fentanyl deserves to be extensively evaluated.
AB  - Fentanil, predstavnik grupe sintetičkih opioidnih analgetika (4-anilidopiperidina), ima široku primenu kao dodatak opštoj anesteziji, u terapiji postoperativnog bola, kao i bola uzrokovanog karcinomima. Medjutim, kao i drugi m agonisti opioidnih receptora, fentanil prouzrokuje ozbiljne neželjene efekate kao što su depresija disanja, rigiditet skeletne muskulature, a posle duže primene dolazi do pojave tolerancije i zavisnosti. Tokom poslednje četiri decenije uloženi su značajni napori da se sintetiše veliki broj analoga fentanila, kao i da se ustanovi odnos hemijske strukture i farmakološke aktivnosti (SAR) grupe analgetika koji pripadaju 4-anilidopiperidinima, a sve to u cilju pronalaženja analgetika sa boljim farmakodinamskim i farmakokinetičkim profilom dejstva. Cilj SAR studija je da se što više približimo profilu idealnog analgetika sa akcentom uglavnom na jačini, bezbednosti i dužini dejstva. Kao rezultat svih ovih napora, otkriveno je nekoliko jedinjenja srodnih fentanilu koji su našli kliničku primenu u anesteziji: alfentanil, sufentanil i remifentanil. U toku je detaljno ispitivanje nekoliko drugih jedinjenja u eksperimen­tima na životinjama, dok su neka od njih predložena kao korisni ligandi u receptorskim studijama. Interesantni rezultati dobijeni u SAR studijama sa nekoliko novosintetisanih 3-alkil analoga fentanila, kao i 3-karbometoksi fentanila (izo-karfentanila) prikazani su i diskutovani u ovom radu. Analgetička jačina 3-karbometoksi fentanila zavisi uglavnom od sternih faktora (voluminoznost karbometoksi grupe i cis/trans izomerija), dok je uticaj hemijske prirode same karbometoksi grupe verovatno nebitan. Za razliku od jačine, dužina trajanja dejstva 3-karbometoksi fentanila najverovatnije je uslovljena prirodom karbometoksi grupe. Budući da su jačina i dužina dejstva ove nove supstance sa analgetičkim dejstvom interesantni sa aspekta SAR studija, kao i da dosadašnji rezultati obećavaju da bi mogla potencijalno biti primenjivana u klinici, 3-karbometoksi fentanil zaslužuje opsežnije ispitivanje.
T2  - Engrami
T1  - Opioid analgesics: Structure-activity study of the fentanyl analogues
T1  - Opioidni analgetici - studija odnosa strukture i farmakološke aktivnosti analoga fentanila
VL  - 23
IS  - 3-4
SP  - 31
EP  - 49
UR  - https://hdl.handle.net/21.15107/rcub_cherry_139
ER  - 

@article{
author = "Vučković, Sonja M. and Prostran, Milica and Ivanović, Milovan and Todorović, Zoran B. and Stojanović, Radan and Nešić, Zorica and Matić, Ivana",
year = "2001",
abstract = "Fentanyl, the prototype of the 4-anilidopiperidine class of synthetic opioid analgesics, is widely and successfully used to supplement general anesthesia or to treat postoperative and cancer pain. However, like other m agonists, fentanyl produces serious adverse effects including respiratory depression, muscle rigidity and on prolonged use, tolerance and addiction. In order to discover an analgesic with the improved pharmacodynamic and pharmacokinetic profile, extensive efforts during last four decades have been devoted to synthesis of a large number of fentanyl analogues and establishing the structure-activity-relationship (SAR) of the 4-anilidopiperidine class of analgesics. The objective of SAR studies is to approach the ideal analgesic profile focusing mainly on potency, safety and duration of action. As a result of such efforts, several congeners of fentanyl: alfentanil, sufentanil and remifentanil were discovered and have found clinical use as anesthesia adjuncts. Several other compounds are still under extensive evaluation in animals nowadays, while some of them are proposed as a useful tools in studying the opioid receptors. An interesting SAR obtained with some newly synthesized 3-alkyl fentanyl analogues, as well as 3-carbomethoxy fentanyl (iso-carfentanil) is presented and discussed in this paper. The analgesic potency of 3-carbomethoxy fentanyl is influenced mainly by the steric factor (voluminosity of the carbomethoxy group and the cis/trans isomerism), while the chemical nature of the group is probably irrelevant. In contrast to potency, the duration of action of 3-carbomethoxy fentanyl is most likely influenced by the nature of the carbomethoxy group. Since the potency and the duration of action of this novel analgesic compound are interesting from the aspect of SAR studies, and have potential promise for clinical use, 3-carbomethoxy fentanyl deserves to be extensively evaluated., Fentanil, predstavnik grupe sintetičkih opioidnih analgetika (4-anilidopiperidina), ima široku primenu kao dodatak opštoj anesteziji, u terapiji postoperativnog bola, kao i bola uzrokovanog karcinomima. Medjutim, kao i drugi m agonisti opioidnih receptora, fentanil prouzrokuje ozbiljne neželjene efekate kao što su depresija disanja, rigiditet skeletne muskulature, a posle duže primene dolazi do pojave tolerancije i zavisnosti. Tokom poslednje četiri decenije uloženi su značajni napori da se sintetiše veliki broj analoga fentanila, kao i da se ustanovi odnos hemijske strukture i farmakološke aktivnosti (SAR) grupe analgetika koji pripadaju 4-anilidopiperidinima, a sve to u cilju pronalaženja analgetika sa boljim farmakodinamskim i farmakokinetičkim profilom dejstva. Cilj SAR studija je da se što više približimo profilu idealnog analgetika sa akcentom uglavnom na jačini, bezbednosti i dužini dejstva. Kao rezultat svih ovih napora, otkriveno je nekoliko jedinjenja srodnih fentanilu koji su našli kliničku primenu u anesteziji: alfentanil, sufentanil i remifentanil. U toku je detaljno ispitivanje nekoliko drugih jedinjenja u eksperimen­tima na životinjama, dok su neka od njih predložena kao korisni ligandi u receptorskim studijama. Interesantni rezultati dobijeni u SAR studijama sa nekoliko novosintetisanih 3-alkil analoga fentanila, kao i 3-karbometoksi fentanila (izo-karfentanila) prikazani su i diskutovani u ovom radu. Analgetička jačina 3-karbometoksi fentanila zavisi uglavnom od sternih faktora (voluminoznost karbometoksi grupe i cis/trans izomerija), dok je uticaj hemijske prirode same karbometoksi grupe verovatno nebitan. Za razliku od jačine, dužina trajanja dejstva 3-karbometoksi fentanila najverovatnije je uslovljena prirodom karbometoksi grupe. Budući da su jačina i dužina dejstva ove nove supstance sa analgetičkim dejstvom interesantni sa aspekta SAR studija, kao i da dosadašnji rezultati obećavaju da bi mogla potencijalno biti primenjivana u klinici, 3-karbometoksi fentanil zaslužuje opsežnije ispitivanje.",
journal = "Engrami",
title = "Opioid analgesics: Structure-activity study of the fentanyl analogues, Opioidni analgetici - studija odnosa strukture i farmakološke aktivnosti analoga fentanila",
volume = "23",
number = "3-4",
pages = "31-49",
url = "https://hdl.handle.net/21.15107/rcub_cherry_139"
}

Vučković, S. M., Prostran, M., Ivanović, M., Todorović, Z. B., Stojanović, R., Nešić, Z.,& Matić, I.. (2001). Opioid analgesics: Structure-activity study of the fentanyl analogues. in Engrami, 23(3-4), 31-49.
https://hdl.handle.net/21.15107/rcub_cherry_139

Vučković SM, Prostran M, Ivanović M, Todorović ZB, Stojanović R, Nešić Z, Matić I. Opioid analgesics: Structure-activity study of the fentanyl analogues. in Engrami. 2001;23(3-4):31-49.
https://hdl.handle.net/21.15107/rcub_cherry_139 .

Vučković, Sonja M., Prostran, Milica, Ivanović, Milovan, Todorović, Zoran B., Stojanović, Radan, Nešić, Zorica, Matić, Ivana, "Opioid analgesics: Structure-activity study of the fentanyl analogues" in Engrami, 23, no. 3-4 (2001):31-49,
https://hdl.handle.net/21.15107/rcub_cherry_139 .