Accesso libero

Carbamate group as structural motif in drugs: a review of carbamate derivatives used as therapeutic agents

Ana Matošević

Ana Matošević

Institute for Medical Research and Occupational HealthZagreb, Croatia
Cerca questo autore su
Sciendo|Google Scholar
Matošević, Ana
 e 
Anita Bosak

Anita Bosak

Institute for Medical Research and Occupational HealthZagreb, Croatia
Cerca questo autore su
Sciendo|Google Scholar
Bosak, Anita
  
31 dic 2020
Carbamate group as structural motif in drugs: a review of carbamate derivatives used as therapeutic agents's Cover Image
INFORMAZIONI SU QUESTO ARTICOLO
Articolo precedente
Articolo Successivo
Cita
Scarica la copertina
Categoria dell'articolo: Review
Pubblicato online: 31 dic 2020
Pagine: 285 - 299
Ricevuto: 01 lug 2020
Accettato: 01 dic 2020
DOI: https://doi.org/10.2478/aiht-2020-71-3466
Parole chiave
© 2020 Ana Matošević, Anita Bosak, published by Sciendo
This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

Figure 1

Structures of carbamate-based drugs and prodrugs of different application (carbamate group is presented in blue; active substance of prodrugs is presented in red)
Structures of carbamate-based drugs and prodrugs of different application (carbamate group is presented in blue; active substance of prodrugs is presented in red)

Figure 2

Possible resonance structures for the carbamate group (amino group is presented in red, and alkoxy group in blue) (adopted from ref. 14)
Possible resonance structures for the carbamate group (amino group is presented in red, and alkoxy group in blue) (adopted from ref. 14)

Figure 3

Cis and trans conformations of carbamates (adopted from ref. 14)
Cis and trans conformations of carbamates (adopted from ref. 14)

Figure 4

Alkaline hydrolysis of monosubstituted (A) and disubstituted (B) carbamates (adopted from ref. 22)
Alkaline hydrolysis of monosubstituted (A) and disubstituted (B) carbamates (adopted from ref. 22)

Figure 5

Mechanism of action of mitomycin C (adopted from ref. 40)
Mechanism of action of mitomycin C (adopted from ref. 40)

Figure 6

Proposed targets and mechanism of action of felbamate and retigabine in postsynaptic neuron (adopted from refs. 62 and 63)
Proposed targets and mechanism of action of felbamate and retigabine in postsynaptic neuron (adopted from refs. 62 and 63)

Figure 7

A proposed simplified mechanism for AChE inhibition by carbamates. Rapid formation of the covalent enzyme-carbamate intermediates, followed by slow regeneration of a free AChE prevents breaking down of acetylcholine in postsynaptic cleft by AChE (adopted from ref. 81)
A proposed simplified mechanism for AChE inhibition by carbamates. Rapid formation of the covalent enzyme-carbamate intermediates, followed by slow regeneration of a free AChE prevents breaking down of acetylcholine in postsynaptic cleft by AChE (adopted from ref. 81)

Figure 8

Cymserine and its derivatives (carbamate group in blue) (adopted from ref. 82)
Cymserine and its derivatives (carbamate group in blue) (adopted from ref. 82)

Figure 9

Chemical structure of secretase inhibitors tested with potential to be used in treatment of Alzheimer’s disease A – a 16-membered macrocycle compound; B – sulphonamide compound (adopted from ref. 8)
Chemical structure of secretase inhibitors tested with potential to be used in treatment of Alzheimer’s disease A – a 16-membered macrocycle compound; B – sulphonamide compound (adopted from ref. 8)

Figure 10

A simplified illustration of the prodrug concept
A simplified illustration of the prodrug concept

Figure 11

Irinotecan metabolism by carboxylesterases hCE-1 and hCE-2 (adopted from ref. 105)
Irinotecan metabolism by carboxylesterases hCE-1 and hCE-2 (adopted from ref. 105)

Figure 12

Bambuterol metabolism into tertbutaline by cytochrome p450 and butyrylcholinesterase (BChE) (adopted from ref. 106)
Bambuterol metabolism into tertbutaline by cytochrome p450 and butyrylcholinesterase (BChE) (adopted from ref. 106)

Roles of the carbamate moiety in drugs and prodrugs

Drug The role of the carbamate moiety in the drug Reference
Docetaxel prolongs drug action, increases drug potency, improves water solubility 39
Mytomicin C participates in the formation of an alkylating compound during reaction with target 40
Rivastigmine, neostigmine, physostigmine, pyridostigmine key element for interaction with the target 38
Ritonavir, amprenavir, atazanavir, darunavir improves drug bioavailability and potency, engaged in a backbone interaction with protease 8
Ombitasvir, elbasvir, daclatasavir improves drug stability and lipophilicity 41
Febendazole, mebendazole, febantel, albendazole improves aqueous solubility and bioavailability, increases cytotoxicity 42
Mehocarabamol, metaxalone inhibits acetylcholinesterase at synapses in the autonomic nervous system, neuromuscular junction, and central nervous system 43
Felbamate improves drug stability and bioavailability 44, 45
Retigabine major pharmacophore responsible for interacting with residues in the KCNQ2–5 channels 46
Gabapentin enacarbil improves bioavailability 47
Capecitabine improves selectivity and bioavailability 47
Bambuterol delays first-pass metabolism 47
Irinotecan improves aqueous solubility 47
Lingue:
Inglese, Croatian, Slovenian
Frequenza di pubblicazione:
4 volte all'anno
Argomenti della rivista:
Medicina, Scienze medicali di base, Scienze medicali di base, altro
Feed RSS della rivista