Oksibutinin

Oksibutinin
(IUPAC) ime
	4-Dietilaminobut-2-inil 2-cikloheksil-2-hidroksi-2-feniletanoat
Klinički podaci
Robne marke	Ditropan
AHFS/Drugs.com	Monografija
MedlinePlus	a682141
Identifikatori
CAS broj	5633-20-5
ATC kod	G04BD04
PubChem	4634
DrugBank	APRD00427
ChemSpider	4473
UNII	K9P6MC7092
KEGG	D00465
ChEBI	CHEBI:7856
ChEMBL	CHEMBL1231
Hemijski podaci
Formula	C22H31NO3
Mol. masa	357,486 g/mol
SMILES	eMolekuli & PubHem
InChI
	InChI=1S/C22H31NO3/c1-3-23(4-2)17-11-12-18-26-21(24)22(25,19-13-7-5-8-14-19)20-15-9-6-10-16-20/h5,7-8,13-14,20,25H,3-4,6,9-10,15-18H2,1-2H3 ; Key: XIQVNETUBQGFHX-UHFFFAOYSA-N
Farmakokinetički podaci
Vezivanje za proteine plazme	91%-93%
Poluvreme eliminacije	12,4-13,2 sata
Farmakoinformacioni podaci
Trudnoća	?
Pravni status	Rx Only (CA), Rx Only (US)
Način primene	oralno, transdermalno

Oksibutinin (Ditropan, Lirinel XL) je antiholinergijski lek koji se koristi za olakšavanje urinarnih problema, što obuhvata frekventno mokrenje i nesposobnost kontrole urinacije. On deluje putem umanjenja mišićnih spazama bešike.^[7] Oksibutinin je kompetitivni antagonist M1, M2, i M3 podtip muskarinskog acetilholinskog receptora. On isto tako ima direktno spazmolitičko dejstvo na glatke mišiće bešike kao kalcijumski antagonist i lokalni anestetik, mada pri koncentracijama koje su daleko iznad onih koje se koriste u kliničkoj praksi. On je dostupan za oralnu primenu kao generička formulacija i pod brand imenima Ditropan i Lyrinel XL. On je isto tako na tržištu u obliku transdermalnog flaster pod imenom Oksitrol, i kao topikalni gel pod imenom Gelnique.

Oksibutinin je takođe mogući tretman za hiperhidrozu, ili hiperaktivno znojenje.^[8]^[9]^[10]

Stereokemija

Oxybutynin sadrži stereocentar i sastoji se od dva enantiomera. Ovo je racemat, tj. 1: 1 smjesa (R) - i (S) -form:^[11]^[12]

Enantiomeri oksibutinina
CAS-Nummer: 119618-21-2	CAS-Nummer: 119618-22-3

Reference

↑ Li Q, Cheng T, Wang Y, Bryant SH (2010). „PubChem as a public resource for drug discovery.”. Drug Discov Today 15 (23-24): 1052-7. DOI:10.1016/j.drudis.2010.10.003. PMID 20970519. edit
↑ Evan E. Bolton, Yanli Wang, Paul A. Thiessen, Stephen H. Bryant (2008). „Chapter 12 PubChem: Integrated Platform of Small Molecules and Biological Activities”. Annual Reports in Computational Chemistry 4: 217-241. DOI:10.1016/S1574-1400(08)00012-1.
↑ Hettne KM, Williams AJ, van Mulligen EM, Kleinjans J, Tkachenko V, Kors JA. (2010). „Automatic vs. manual curation of a multi-source chemical dictionary: the impact on text mining”. J Cheminform 2 (1): 3. DOI:10.1186/1758-2946-2-3. PMID 20331846. edit
↑ Joanne Wixon, Douglas Kell (2000). „Website Review: The Kyoto Encyclopedia of Genes and Genomes — KEGG”. Yeast 17 (1): 48–55. DOI:10.1002/(SICI)1097-0061(200004)17:1<48::AID-YEA2>3.0.CO;2-H.
↑ Gaulton A, Bellis LJ, Bento AP, Chambers J, Davies M, Hersey A, Light Y, McGlinchey S, Michalovich D, Al-Lazikani B, Overington JP. (2012). „ChEMBL: a large-scale bioactivity database for drug discovery”. Nucleic Acids Res 40 (Database issue): D1100-7. DOI:10.1093/nar/gkr777. PMID 21948594. edit
↑ „Product Information”. Drug Product Database. Pristupljeno 13. 8. 2011. ^{[mrtav link]}
↑ Chapple CR. "Muscarinic receptor antagonists in the treatment of overactive bladder". Urology (55)5, Supp. 1:33-46, 2000.
↑ Tupker RA, Harmsze AM, Deneer VH (2006). „Oxybutynin therapy for generalized hyperhidrosis.”. Arch Dermatol 142 (8): 1065–6. DOI:10.1001/archderm.142.8.1065. PMID 16924061.
↑ Mijnhout GS, Kloosterman H, Simsek S, Strack van Schijndel RJ, Netelenbos JC. (2006). „Oxybutynin: dry days for patients with hyperhidrosis.”. Neth J Med 64 (9): 326–8. PMID 17057269.
↑ Schollhammer M, Misery L. (2007). „Treatment of hyperhidrosis with oxybutynin.”. Arch Dermatol. 143 (4): 544–5. DOI:10.1001/archderm.143.4.544. PMID 17438194.
↑ Kachur JF, et al. R and S enantiomers of oxybutynin: pharmacological effects in guinea pig bladder and intestine, Journal of Pharmacology and Experimental Therapeutics, 247, S. 867–872, 1988; PMID 2849672.
↑ Noronha-Blob L, Kachur JF. Enantiomers of oxybutynin: in vitro pharmacological characterization at M₁, M₂ and M₃ muscarinic receptors and in vivo effects on urinary bladder contraction, mydriasis and salivary secretion in guinea pigs, Journal of Pharmacology and Experimental Therapeutics, 256, S. 562–567, 1991; PMID 1993995.

Spoljašnje veze

	Portal Medicina
	Portal Hemija

[1] Li Q, Cheng T, Wang Y, Bryant SH (2010). „PubChem as a public resource for drug discovery.”. Drug Discov Today 15 (23-24): 1052-7. DOI:10.1016/j.drudis.2010.10.003. PMID 20970519. edit

[2] Evan E. Bolton, Yanli Wang, Paul A. Thiessen, Stephen H. Bryant (2008). „Chapter 12 PubChem: Integrated Platform of Small Molecules and Biological Activities”. Annual Reports in Computational Chemistry 4: 217-241. DOI:10.1016/S1574-1400(08)00012-1.

[3] Hettne KM, Williams AJ, van Mulligen EM, Kleinjans J, Tkachenko V, Kors JA. (2010). „Automatic vs. manual curation of a multi-source chemical dictionary: the impact on text mining”. J Cheminform 2 (1): 3. DOI:10.1186/1758-2946-2-3. PMID 20331846. edit

[4] Joanne Wixon, Douglas Kell (2000). „Website Review: The Kyoto Encyclopedia of Genes and Genomes — KEGG”. Yeast 17 (1): 48–55. DOI:10.1002/(SICI)1097-0061(200004)17:1<48::AID-YEA2>3.0.CO;2-H.

[5] Gaulton A, Bellis LJ, Bento AP, Chambers J, Davies M, Hersey A, Light Y, McGlinchey S, Michalovich D, Al-Lazikani B, Overington JP. (2012). „ChEMBL: a large-scale bioactivity database for drug discovery”. Nucleic Acids Res 40 (Database issue): D1100-7. DOI:10.1093/nar/gkr777. PMID 21948594. edit

[6] „Product Information”. Drug Product Database. Pristupljeno 13. 8. 2011. ^{[mrtav link]}

[7] Chapple CR. "Muscarinic receptor antagonists in the treatment of overactive bladder". Urology (55)5, Supp. 1:33-46, 2000.

[8] Tupker RA, Harmsze AM, Deneer VH (2006). „Oxybutynin therapy for generalized hyperhidrosis.”. Arch Dermatol 142 (8): 1065–6. DOI:10.1001/archderm.142.8.1065. PMID 16924061.

[9] Mijnhout GS, Kloosterman H, Simsek S, Strack van Schijndel RJ, Netelenbos JC. (2006). „Oxybutynin: dry days for patients with hyperhidrosis.”. Neth J Med 64 (9): 326–8. PMID 17057269.

[10] Schollhammer M, Misery L. (2007). „Treatment of hyperhidrosis with oxybutynin.”. Arch Dermatol. 143 (4): 544–5. DOI:10.1001/archderm.143.4.544. PMID 17438194.

[11] Kachur JF, et al. R and S enantiomers of oxybutynin: pharmacological effects in guinea pig bladder and intestine, Journal of Pharmacology and Experimental Therapeutics, 247, S. 867–872, 1988; PMID 2849672.

[12] Noronha-Blob L, Kachur JF. Enantiomers of oxybutynin: in vitro pharmacological characterization at M₁, M₂ and M₃ muscarinic receptors and in vivo effects on urinary bladder contraction, mydriasis and salivary secretion in guinea pigs, Journal of Pharmacology and Experimental Therapeutics, 256, S. 562–567, 1991; PMID 1993995.

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