TY  - JOUR
AU  - Vuckovic, S
AU  - Prostran, M
AU  - Ivanović, Milovan
AU  - Ristovic, Z
AU  - Stojanović, R.
PY  - 2000
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/388
AB  - 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 antinociceptive drugs. In this study, the newly synthesized fentanyl analogue 3-carbomethoxy fentanyl (iso-carfentanil) was compared to fentanyl for its antinociceptive activity (tail-immersion test) in rats. It was revealed that the introduction of a 3-carbomethoxy group in the piperidine ring of fentanyl skeleton reduced the potency and shortened the duration of action of the parent compound, i.e., fentanyl. The antinociceptive 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. This is in agreement with SAR studies of other 3-substituted fentanyl analogues. In contrast to potency, the duration of action is not affected by cis/trans isomerism. It is assumed that the time course of action of 3-carbomethoxy fentanyl is influenced by the nature of the carbomethoxy group. Since the potency and the duration of action of this novel antinociceptive compound are interesting from the aspect of SAR studies and have potential promise for clinical application, 3-carbomethoxy fentanyl deserves to be extensively evaluated.
PB  - Japanese Pharmacological Soc, Kyoto
T2  - Japanese Journal of Pharmacology
T1  - Antinociceptive activity of the novel fentanyl analogue iso-carfentanil in rats
VL  - 84
IS  - 2
SP  - 188
EP  - 195
DO  - 10.1254/jjp.84.188
ER  - 

@article{
author = "Vuckovic, S and Prostran, M and Ivanović, Milovan and Ristovic, Z and Stojanović, R.",
year = "2000",
abstract = "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 antinociceptive drugs. In this study, the newly synthesized fentanyl analogue 3-carbomethoxy fentanyl (iso-carfentanil) was compared to fentanyl for its antinociceptive activity (tail-immersion test) in rats. It was revealed that the introduction of a 3-carbomethoxy group in the piperidine ring of fentanyl skeleton reduced the potency and shortened the duration of action of the parent compound, i.e., fentanyl. The antinociceptive 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. This is in agreement with SAR studies of other 3-substituted fentanyl analogues. In contrast to potency, the duration of action is not affected by cis/trans isomerism. It is assumed that the time course of action of 3-carbomethoxy fentanyl is influenced by the nature of the carbomethoxy group. Since the potency and the duration of action of this novel antinociceptive compound are interesting from the aspect of SAR studies and have potential promise for clinical application, 3-carbomethoxy fentanyl deserves to be extensively evaluated.",
publisher = "Japanese Pharmacological Soc, Kyoto",
journal = "Japanese Journal of Pharmacology",
title = "Antinociceptive activity of the novel fentanyl analogue iso-carfentanil in rats",
volume = "84",
number = "2",
pages = "188-195",
doi = "10.1254/jjp.84.188"
}

Vuckovic, S., Prostran, M., Ivanović, M., Ristovic, Z.,& Stojanović, R.. (2000). Antinociceptive activity of the novel fentanyl analogue iso-carfentanil in rats. in Japanese Journal of Pharmacology
Japanese Pharmacological Soc, Kyoto., 84(2), 188-195.
https://doi.org/10.1254/jjp.84.188

Vuckovic S, Prostran M, Ivanović M, Ristovic Z, Stojanović R. Antinociceptive activity of the novel fentanyl analogue iso-carfentanil in rats. in Japanese Journal of Pharmacology. 2000;84(2):188-195.
doi:10.1254/jjp.84.188 .

Vuckovic, S, Prostran, M, Ivanović, Milovan, Ristovic, Z, Stojanović, R., "Antinociceptive activity of the novel fentanyl analogue iso-carfentanil in rats" in Japanese Journal of Pharmacology, 84, no. 2 (2000):188-195,
https://doi.org/10.1254/jjp.84.188 . .

TY  - JOUR
AU  - Vuckovic, S
AU  - Ivanović, Milovan
AU  - Prostran, M
AU  - Todorović, Zoran B.
AU  - Ristovic, Z
AU  - Micovic, I
AU  - Beleslin, D.
PY  - 1998
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/403
AB  - The influence of higher environmental temperature (HET=30+/-1 degrees C) on fentanyl-induced behavior was studied in unrestrained rats. Subacute exposure (3 days) of rats to HET significantly (P  lt 0.01) increased the cataleptic effect of fentanyl citrate (0.5 mg/kg), in comparison to the corresponding exposure to normal environmental temperature (NET=22+/-1 degrees C). Also, the hyperthermic response of rats to a low dose of fentanyl citrate (0.2-0.5 mg/kg) was significantly (P lt 0.01) potentiated, and the hypothermic response to a high dose of fentanyl citrate (1.5 mg/kg) was significantly (P  lt 0.05) attenuated after exposure to HET. Fentanyl-induced hyperexcitability, loss of righting reflex, loss of corneal reflex and analgesia were not significantly affected by HET. This study provides the first evidence on the influence of environmental temperature on drug-induced catalepsy. MET-induced potentiation of the cataleptic response to fentanyl could be the result of an interference with behavioral thermoregulation.
PB  - Japanese Pharmacological Soc, Kyoto
T2  - Japanese Journal of Pharmacology
T1  - Higher environmental temperature potentiates cataleptic effect of fentanyl in rats
VL  - 78
IS  - 4
SP  - 523
EP  - 527
DO  - 10.1254/jjp.78.523
ER  - 

@article{
author = "Vuckovic, S and Ivanović, Milovan and Prostran, M and Todorović, Zoran B. and Ristovic, Z and Micovic, I and Beleslin, D.",
year = "1998",
abstract = "The influence of higher environmental temperature (HET=30+/-1 degrees C) on fentanyl-induced behavior was studied in unrestrained rats. Subacute exposure (3 days) of rats to HET significantly (P  lt 0.01) increased the cataleptic effect of fentanyl citrate (0.5 mg/kg), in comparison to the corresponding exposure to normal environmental temperature (NET=22+/-1 degrees C). Also, the hyperthermic response of rats to a low dose of fentanyl citrate (0.2-0.5 mg/kg) was significantly (P lt 0.01) potentiated, and the hypothermic response to a high dose of fentanyl citrate (1.5 mg/kg) was significantly (P  lt 0.05) attenuated after exposure to HET. Fentanyl-induced hyperexcitability, loss of righting reflex, loss of corneal reflex and analgesia were not significantly affected by HET. This study provides the first evidence on the influence of environmental temperature on drug-induced catalepsy. MET-induced potentiation of the cataleptic response to fentanyl could be the result of an interference with behavioral thermoregulation.",
publisher = "Japanese Pharmacological Soc, Kyoto",
journal = "Japanese Journal of Pharmacology",
title = "Higher environmental temperature potentiates cataleptic effect of fentanyl in rats",
volume = "78",
number = "4",
pages = "523-527",
doi = "10.1254/jjp.78.523"
}

Vuckovic, S., Ivanović, M., Prostran, M., Todorović, Z. B., Ristovic, Z., Micovic, I.,& Beleslin, D.. (1998). Higher environmental temperature potentiates cataleptic effect of fentanyl in rats. in Japanese Journal of Pharmacology
Japanese Pharmacological Soc, Kyoto., 78(4), 523-527.
https://doi.org/10.1254/jjp.78.523

Vuckovic S, Ivanović M, Prostran M, Todorović ZB, Ristovic Z, Micovic I, Beleslin D. Higher environmental temperature potentiates cataleptic effect of fentanyl in rats. in Japanese Journal of Pharmacology. 1998;78(4):523-527.
doi:10.1254/jjp.78.523 .

Vuckovic, S, Ivanović, Milovan, Prostran, M, Todorović, Zoran B., Ristovic, Z, Micovic, I, Beleslin, D., "Higher environmental temperature potentiates cataleptic effect of fentanyl in rats" in Japanese Journal of Pharmacology, 78, no. 4 (1998):523-527,
https://doi.org/10.1254/jjp.78.523 . .