Acetilcistein

Acetilcistein
	2-Acetamido-3-sulfanilpropanoinska kiselina
Identifikacija
CAS registarski broj	7218-04-4 , 616-91-1 R , 26117-28-2 S
PubChem	581, ; 12035 R, ; 94364 S
ChemSpider	561 , 11540 R , 85162 S
UNII	WYQ7N0BPYC
EINECS broj	230-609-9
DrugBank	DB06151
KEGG	D00221
MeSH	Acetylcysteine
ChEBI	28939
ChEMBL	CHEMBL600
RTECS registarski broj toksičnosti	HA1660000 R
ATC code	R05CB01,S01XA08, V03AB23
Bajlštajn	1724426 R
Gmelin Referenca	142554 R
Jmol-3D slike	Slika 1
SMILES
	CC(=O)NC(CS)C(O)=O
InChI
	InChI=1S/C5H9NO3S/c1-3(7)6-4(2-10)5(8)9/h4,10H,2H2,1H3,(H,6,7)(H,8,9) ; Kod: PWKSKIMOESPYIA-UHFFFAOYSA-N
Svojstva
Molekulska formula	C5H9NO3S
Molarna masa	163.19 g mol−1
Agregatno stanje	Beli, neprozirni kristali
Tačka topljenja	106-108 °C, 379-381 K, 223-226 °F
log P	−0,696
pKa	3,252
Baznost (pKb)	10,745
Farmakologija
Bioraspoloživost	6–10% (oralno); <3% (inhalaciono);
Načini upotrebe	Inhalaciono; Intravenozno; Oralno;
Metabolizam	Hepatčki
Vreme polu-uklanjanja iz organizma	5,6 sati (odrasli); 11 sati (novorođenčad);
Ekskrecija	Renal
Licenca	US
Legalni status	Prescription Only (S4)(AU) ; ℞-only(SAD)
Kategorija; trudnoće
Opasnost
S-oznake	S22, S24/25
LD50	5,050 mg kg−1 (oralno, pacov)
Srodna jedinjenja
Srodna alkanske kiseline	Glicilglicin; Iminodisirćetna kiselina; Nitrilotrisirćetna kiselina; N-Oksalilglicin; Tiopronin; Bucilamin; Oksalildiaminopropionska kiselina;
Srodna jedinjenja	N-Acetilglicinamid
	(šta je ovo?) (verifikuj) ; Ukoliko nije drugačije napomenuto, podaci se odnose na standardno stanje (25 °C, 100 kPa) materijala
	Infobox references

Acetilcystein (N-acetil-L-cistein, NAC), je lek koji se koristi za lečenje predoziranja paracetamolom (acetaminofenpm) i za razvodnjavanje guste sluzi kod obolelih od bronhopulmonarnih bolesti, poput zapaljenja pluća i bronhitisa.^[7] Može se primeniti intravenski, preko usta, ili inhalacijom.^[7] Koristi se i kao dodatak hrani.^[8]^[9]

Druge upotrebe uključuju sulfatno snabdevanje kod oboljenja kao što su autizam, gde cistein i srodne sumporne amino kiseline mogu da budu iscrpljene.^[10]

Acetilcistein je derivat cisteina; jedna acetil grupa je vezana za atom azota. Ovo jedinjenje je u prodaji kao dijetetski suplement za koji se smatra da deluje kao antioksidans i da štiti jetru. On se koristi kao lek za kašalj jer raskida disulfidne veze u sluzi i utečnjava je, te se lakše iskašljava. To svojstvo je takođe koristno u redukovanju abnormalno guste sluzi kod obolelih od cistične i pulmonarne fibroze.

Reference

↑ „L-Cysteine, N-acetyl- - Compound Summary”. PubChem Compound. USA: National Center for Biotechnology Information. 25 March 2005. Identification. Pristupljeno 9 January 2012.
↑ 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
↑ ^7,0 ^7,1 „Acetylcysteine”. The American Society of Health-System Pharmacists. Arhivirano iz originala na datum 23 September 2015. Pristupljeno 22 Aug 2015.
↑ Talbott, Shawn M. (2012) (en). A Guide to Understanding Dietary Supplements. Routledge. str. 469. ISBN 9781136805707. Arhivirano iz originala na datum 8 September 2017.
↑ „Cysteine” (en). University of Maryland Medical Center. Arhivirano iz originala na datum 2017-07-01. Pristupljeno 23 June 2017.
↑ Geier, David A.; Geier, Mark R. (2006). „A Clinical and Laboratory Evaluation of Methionine Cycle-Transsulfuration and Androgen Pathway Markers in Children with Autistic Disorders”. Hormone Research 66 (4): 182–8. DOI:10.1159/000094467. PMID 16825783.

Literatura

Stanislaus, Romesh; Gilg, Anne G; Singh, Avtar K; Singh, Inderjit (2005). „N-acetyl-L-cysteine ameliorates the inflammatory disease process in experimental autoimmune encephalomyelitis in Lewis rats.”. Journal of Autoimmune Diseases 2 (1): 4. DOI:10.1186/1740-2557-2-4. PMC 1097751. PMID 15869713.

Vanjske veze

CIMS India database "[1]^{[mrtav link]}"
N-acetylcysteine replenishes glutathione in HIV infection. "[2] Arhivirano 2012-03-07 na Wayback Machine-u"
British National Formulary 55, March 2008; ISBN 978-0-85369-776-3
U.S. National Library of Medicine: Drug Information Portal - Acetylcysteine
Research based information on Acetylcysteine as a nutritional supplement Arhivirano 2013-06-08 na Wayback Machine-u

[1] „L-Cysteine, N-acetyl- - Compound Summary”. PubChem Compound. USA: National Center for Biotechnology Information. 25 March 2005. Identification. Pristupljeno 9 January 2012.

[2] 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

[3] 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.

[4] 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

[5] 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.

[6] 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

[AHFS2015-7] 7,0 ^7,1 „Acetylcysteine”. The American Society of Health-System Pharmacists. Arhivirano iz originala na datum 23 September 2015. Pristupljeno 22 Aug 2015.

[8] Talbott, Shawn M. (2012) (en). A Guide to Understanding Dietary Supplements. Routledge. str. 469. ISBN 9781136805707. Arhivirano iz originala na datum 8 September 2017.

[9] „Cysteine” (en). University of Maryland Medical Center. Arhivirano iz originala na datum 2017-07-01. Pristupljeno 23 June 2017.

[pm1-10] Geier, David A.; Geier, Mark R. (2006). „A Clinical and Laboratory Evaluation of Methionine Cycle-Transsulfuration and Androgen Pathway Markers in Children with Autistic Disorders”. Hormone Research 66 (4): 182–8. DOI:10.1159/000094467. PMID 16825783.

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