Вигабатрин

Вигабатрин
Klinički podaci
Prodajno ime	Sabril, Sabrilan, Sabrilex
Drugs.com	Monografija
Način primene	Oralno
Farmakokinetički podaci
Poluvreme eliminacije	7,5 ± 2,1 h
Izlučivanje	Renalno (80%)
Identifikatori
CAS број	60643-86-9
ATC kod	N03AG04 (WHO)
PubChem	CID 5665
DrugBank	DB01080
ChemSpider	5463
KEGG	C07500
ChEMBL	CHEMBL89598
Hemijski podaci
Formula	C6H11NO2
Molarna masa	129,157
	SMILES NC(CCC(O)=O)C=C; ;
	InChI InChI=1S/C6H11NO2/c1-2-5(7)3-4-6(8)9/h2,5H,1,3-4,7H2,(H,8,9) ; Key:PJDFLNIOAUIZSL-UHFFFAOYSA-N ;

Vigabatrin je organsko jedinjenje, koje sadrži 6 atoma ugljenika i ima molekulsku masu od 129,157 Da.^[1]^[2]^[3]^[4]^[5]^[6]^[7]^[8]^[9]

Osobine

Osobina	Vrednost
Broj akceptora vodonika	3
Broj donora vodonika	2
Broj rotacionih veza	4
Particioni koeficijent^[10] (ALogP)	-2,4
Rastvorljivost^[11] (logS, log(mol/L))	-0,9
Polarna površina^[12] (PSA, Å²)	63,3

Reference

^ Gram, L.; Larsson, O. M.; Johnsen, A.; Schousboe, A. (1989). „Experimental studies of the influence of vigabatrin on the GABA system”. British Journal of Clinical Pharmacology. 27 (Suppl 1): 13S—17S. PMC 1379673 . PMID 2757904. doi:10.1111/j.1365-2125.1989.tb03455.x.
^ Browne, T. R. (1998). „Pharmacokinetics of antiepileptic drugs”. Neurology. 51 (5 Suppl 4): S2—7. PMID 9818917. S2CID 39231047. doi:10.1212/wnl.51.5_suppl_4.s2.
^ Lindberger, M.; Luhr, O.; Johannessen, S. I.; Larsson, S.; Tomson, T. (2003). „Serum concentrations and effects of gabapentin and vigabatrin: Observations from a dose titration study”. Therapeutic Drug Monitoring. 25 (4): 457—462. PMID 12883229. S2CID 35834401. doi:10.1097/00007691-200308000-00007.
^ Zwanzger, P.; Baghai, T. C.; Schuele, C.; Ströhle, A.; Padberg, F.; Kathmann, N.; Schwarz, M.; Möller, H. J.; Rupprecht, R. (2001). „Vigabatrin decreases cholecystokinin-tetrapeptide (CCK-4) induced panic in healthy volunteers”. Neuropsychopharmacology : Official Publication of the American College of Neuropsychopharmacology. 25 (5): 699—703. PMID 11682253. S2CID 25547476. doi:10.1016/S0893-133X(01)00266-4.
^ Tulloch, J. K.; Carr, R. R.; Ensom, M. H. (2012). „A systematic review of the pharmacokinetics of antiepileptic drugs in neonates with refractory seizures”. The Journal of Pediatric Pharmacology and Therapeutics : JPPT : The Official Journal of Ppag. 17 (1): 31—44. PMC 3428186 . PMID 23118657. doi:10.5863/1551-6776-17.1.31.
^ Clayton, L. M.; Stern, W. M.; Newman, W. D.; Sander, J. W.; Acheson, J.; Sisodiya, S. M. (2013). „Evolution of visual field loss over ten years in individuals taking vigabatrin”. Epilepsy Research. 105 (3): 262—271. PMID 23541931. S2CID 12150292. doi:10.1016/j.eplepsyres.2013.02.014.
^ Hawker, D. D.; Silverman, R. B. (2012). „Synthesis and evaluation of novel heteroaromatic substrates of GABA aminotransferase”. Bioorganic & Medicinal Chemistry. 20 (19): 5763—5773. PMC 3448830 . PMID 22944334. doi:10.1016/j.bmc.2012.08.009.
^ Knox, C.; Law, V.; Jewison, T.; Liu, P.; Ly, S.; Frolkis, A.; Pon, A.; Banco, K.; Mak, C.; Neveu, V.; Djoumbou, Y.; Eisner, R.; Guo, A. C.; Wishart, D. S. (2011). „DrugBank 3.0: A comprehensive resource for 'omics' research on drugs”. Nucleic Acids Research. 39 (Database issue): D1035—41. PMC 3013709 . PMID 21059682. doi:10.1093/nar/gkq1126. Текст „noedit” игнорисан (помоћ)
^ Wishart, D. S.; Knox, C.; Guo, A. C.; Cheng, D.; Shrivastava, S.; Tzur, D.; Gautam, B.; Hassanali, M. (2008). „DrugBank: A knowledgebase for drugs, drug actions and drug targets”. Nucleic Acids Research. 36 (Database issue): D901—6. PMC 2238889 . PMID 18048412. doi:10.1093/nar/gkm958. Текст „noedit” игнорисан (помоћ)
^ Ghose, Arup K.; Viswanadhan, Vellarkad N.; Wendoloski, John J. (1998). „Prediction of Hydrophobic (Lipophilic) Properties of Small Organic Molecules Using Fragmental Methods: An Analysis of ALOGP and CLOGP Methods”. The Journal of Physical Chemistry A. 102 (21): 3762—3772. Bibcode:1998JPCA..102.3762G. doi:10.1021/jp980230o. Текст „noedit” игнорисан (помоћ)
^ Tetko, I. V.; Tanchuk, V. Y.; Kasheva, T. N.; Villa, A. E. (2001). „Estimation of aqueous solubility of chemical compounds using E-state indices”. Journal of Chemical Information and Computer Sciences. 41 (6): 1488—1493. PMID 11749573. doi:10.1021/ci000392t. Текст „noedit” игнорисан (помоћ)
^ Ertl, P.; Rohde, B.; Selzer, P. (2000). „Fast calculation of molecular polar surface area as a sum of fragment-based contributions and its application to the prediction of drug transport properties”. Journal of Medicinal Chemistry. 43 (20): 3714—3717. PMID 11020286. doi:10.1021/jm000942e. Текст „noedit” игнорисан (помоћ)

Literatura

Hardman JG, Limbird LE, Gilman AG (2001). Goodman & Gilman's The Pharmacological Basis of Therapeutics (10. изд.). New York: McGraw-Hill. ISBN 0071354697. doi:10.1036/0071422803.
Thomas L. Lemke; David A. Williams, ур. (2007). Foye's Principles of Medicinal Chemistry (6. изд.). Baltimore: Lippincott Willams & Wilkins. ISBN 0781768799.

Spoljašnje veze

Vigabatrin

Molimo Vas, obratite pažnju na važno upozorenje
u vezi sa temama iz oblasti medicine (zdravlja).

[1] Gram, L.; Larsson, O. M.; Johnsen, A.; Schousboe, A. (1989). „Experimental studies of the influence of vigabatrin on the GABA system”. British Journal of Clinical Pharmacology. 27 (Suppl 1): 13S—17S. PMC 1379673 . PMID 2757904. doi:10.1111/j.1365-2125.1989.tb03455.x.

[2] Browne, T. R. (1998). „Pharmacokinetics of antiepileptic drugs”. Neurology. 51 (5 Suppl 4): S2—7. PMID 9818917. S2CID 39231047. doi:10.1212/wnl.51.5_suppl_4.s2.

[3] Lindberger, M.; Luhr, O.; Johannessen, S. I.; Larsson, S.; Tomson, T. (2003). „Serum concentrations and effects of gabapentin and vigabatrin: Observations from a dose titration study”. Therapeutic Drug Monitoring. 25 (4): 457—462. PMID 12883229. S2CID 35834401. doi:10.1097/00007691-200308000-00007.

[4] Zwanzger, P.; Baghai, T. C.; Schuele, C.; Ströhle, A.; Padberg, F.; Kathmann, N.; Schwarz, M.; Möller, H. J.; Rupprecht, R. (2001). „Vigabatrin decreases cholecystokinin-tetrapeptide (CCK-4) induced panic in healthy volunteers”. Neuropsychopharmacology : Official Publication of the American College of Neuropsychopharmacology. 25 (5): 699—703. PMID 11682253. S2CID 25547476. doi:10.1016/S0893-133X(01)00266-4.

[5] Tulloch, J. K.; Carr, R. R.; Ensom, M. H. (2012). „A systematic review of the pharmacokinetics of antiepileptic drugs in neonates with refractory seizures”. The Journal of Pediatric Pharmacology and Therapeutics : JPPT : The Official Journal of Ppag. 17 (1): 31—44. PMC 3428186 . PMID 23118657. doi:10.5863/1551-6776-17.1.31.

[6] Clayton, L. M.; Stern, W. M.; Newman, W. D.; Sander, J. W.; Acheson, J.; Sisodiya, S. M. (2013). „Evolution of visual field loss over ten years in individuals taking vigabatrin”. Epilepsy Research. 105 (3): 262—271. PMID 23541931. S2CID 12150292. doi:10.1016/j.eplepsyres.2013.02.014.

[7] Hawker, D. D.; Silverman, R. B. (2012). „Synthesis and evaluation of novel heteroaromatic substrates of GABA aminotransferase”. Bioorganic & Medicinal Chemistry. 20 (19): 5763—5773. PMC 3448830 . PMID 22944334. doi:10.1016/j.bmc.2012.08.009.

[8] Knox, C.; Law, V.; Jewison, T.; Liu, P.; Ly, S.; Frolkis, A.; Pon, A.; Banco, K.; Mak, C.; Neveu, V.; Djoumbou, Y.; Eisner, R.; Guo, A. C.; Wishart, D. S. (2011). „DrugBank 3.0: A comprehensive resource for 'omics' research on drugs”. Nucleic Acids Research. 39 (Database issue): D1035—41. PMC 3013709 . PMID 21059682. doi:10.1093/nar/gkq1126. Текст „noedit” игнорисан (помоћ)

[9] Wishart, D. S.; Knox, C.; Guo, A. C.; Cheng, D.; Shrivastava, S.; Tzur, D.; Gautam, B.; Hassanali, M. (2008). „DrugBank: A knowledgebase for drugs, drug actions and drug targets”. Nucleic Acids Research. 36 (Database issue): D901—6. PMC 2238889 . PMID 18048412. doi:10.1093/nar/gkm958. Текст „noedit” игнорисан (помоћ)

[10] Ghose, Arup K.; Viswanadhan, Vellarkad N.; Wendoloski, John J. (1998). „Prediction of Hydrophobic (Lipophilic) Properties of Small Organic Molecules Using Fragmental Methods: An Analysis of ALOGP and CLOGP Methods”. The Journal of Physical Chemistry A. 102 (21): 3762—3772. Bibcode:1998JPCA..102.3762G. doi:10.1021/jp980230o. Текст „noedit” игнорисан (помоћ)

[11] Tetko, I. V.; Tanchuk, V. Y.; Kasheva, T. N.; Villa, A. E. (2001). „Estimation of aqueous solubility of chemical compounds using E-state indices”. Journal of Chemical Information and Computer Sciences. 41 (6): 1488—1493. PMID 11749573. doi:10.1021/ci000392t. Текст „noedit” игнорисан (помоћ)

[12] Ertl, P.; Rohde, B.; Selzer, P. (2000). „Fast calculation of molecular polar surface area as a sum of fragment-based contributions and its application to the prediction of drug transport properties”. Journal of Medicinal Chemistry. 43 (20): 3714—3717. PMID 11020286. doi:10.1021/jm000942e. Текст „noedit” игнорисан (помоћ)

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