Sulfanilamid

Vikipediya, ochiq ensiklopediya

Sulfanilamid (shuningdek, sulfanilamid deb ataladi) sulfanilamid antibakterial preparatlar hisoblanadi. Kimyoviy jihatdan bu sulfanilamid guruhi bilan hosil qilingan anilindan tashkil topgan organik birikma hisoblanadi. Kukunli sulfanilamid Ittifoqchilar tomonidan Ikkinchi Jahon urushida infeksiyani kamaytirish uchun ishlatilgan va oldingi urushlarga nisbatan o'lim ko'rsatkichlarining keskin kamayishiga hissa qo'shgan.[1][2] Sulfanilamid kamdan-kam hollarda tizimli ravishda toksikligi va bu maqsadda samaraliroq sulfanilamidlar mavjudligi sababli qo'llaniladi. Zamonaviy antibiotiklar jang maydonida sulfanilamidni almashtirdi; ammo, sulfanilamid bugungi kunda topikal preparatlar shaklida, birinchi navbatda , vaginal achitqi infektsiyalarini, asosan Candida albicans sabab bo'lgan vulvovaginitni davolash uchun qo'llaniladi.[3][4][5][6]

"Sulfanilamidlar" atamasi ba'zan ushbu funksional guruhlarni o'z ichiga olgan molekulalar oilasini tavsiflash uchun ham ishlatiladi. Bunga misollar kiradi:

Ta'sir mexanizmi[tahrir | manbasini tahrirlash]

Sulfanilamid antibiotik sifatida sulfanilamid para -aminobenzoy kislotasi (PABK) ishtirokidagi fermentativ reaktsiyalarni raqobatbardosh ravishda ingibitsiya qilish (ya'ni substrat analogi sifatida harakat qilish) orqali ishlaydi.[7][8] Xususan, u digidropteroat sintaza fermentini raqobatbardosh tarzda ingibotlik qiladi.[4][9] PABK, purinlar va pirimidinlerin sintezida koenzim vazifasini bajaradigan foliy kislotasini ishlab chiqaradigan enzimatik reaktsiyalarda kerak. Sutemizuvchilar o'zlarining foliy kislotasini sintez qilmaydilar, shuning uchun bakteriyalarni tanlab o'ldiradigan PABK ingibitorlariga ta'sir qilmaydi.[10]

Biroq, bu ta'sirni timidin, purinlar, metionin va serin kabi bir uglerodli uzatish reaksiyalarining yakuniy mahsulotlarini qo'shish orqali qaytarish mumkin. PABK sulfanilamidlarning ta'sirini ham bartaraf qilishi mumkin.[4][11][10]

Tarixi[tahrir | manbasini tahrirlash]

Sulfanilamid birinchi marta 1908-yilda avstriyalik kimyogar Pol Yozef Yakob Gelmo (1879–1961)[12][13] tomonidan Venadagi Technische Hochschule doktorlik dissertatsiyasining bir qismi sifatida tayyorlangan.[14] U 1909-yilda patentlangan.[15]

1935-yilda Prontosil prodrugini sinovdan o'tkazishga rahbarlik qilgan Gerxard Domagk[16] va Paster institutida Ernest Fourneau laboratoriyasida Federiko Nitti va Daniel Bovet bilan birga Jak Trefouel va Teres Trefouel sulfani faol shaklda aniqladilar.[17] Odatda sulfanilamidning kimyoterapevtik agent sifatida kashf etilishi bilan bog'liq. Domagk bu ishi uchun Nobel mukofotiga sazovor bo'ldi.[18]

1937-yilda dietilen glikolda erigan sulfanilamiddan tashkil topgan Elixir sulfanilamid preparati o'tkir buyrak etishmovchiligi natijasida 100 dan ortiq odamni zaharladi va o'ldirdi, bu esa AQShda giyohvand moddalarni tekshirish bo'yicha yangi qoidalarni keltirib chiqardi. 1938-yilda oziq-ovqat, dori-darmonlar va kosmetika qonuni qabul qilindi. Muammo sulfanilamid emas, chunki sulfanilamid o'sha paytda tabletka va kukun shaklida keng va xavfsiz ishlatilgan.[19]

Kimyoviy va fizik xossalari[tahrir | manbasini tahrirlash]

Sulfanilamid - sarg'ish-oq yoki oq kristall yoki mayda kukun. Uning zichligi 1,08 g/sm 3, erish nuqtasi 164,5-166,5°C. Sulfanilamidning 0,5% li suvli eritmasining pH qiymati 5,8 dan 6,1 gacha bo'lib, u l max 255 va 312 nm ga ega hisoblanadi.[4]

Eruvchanlik: bir gramm sulfanilamid taxminan 37 ml spirt yoki 5 ml asetonda eriydi. Xloroform, efir yoki benzolda amalda umuman erimaydi.[4]

Qo'llash mumkin bo'lmagan holatlar[tahrir | manbasini tahrirlash]

Sulfanilamid sulfanilamidlarga yuqori sezuvchanligi ma'lum bo'lganlarda, emizikli onalarda, homiladorlik davrida va 2 oylikdan kichik bo'lgan chaqaloqlarda qo'llash mumkin emas.[4]

Salbiy ta'sirlari[tahrir | manbasini tahrirlash]

Bugungi kunda sulfanilamid deyarli faqat topikal vaginal preparatlarda qo'llanilganligi sababli, salbiy ta'sirlar odatda yuqori sezuvchanlik yoki mahalliy teri reaktsiyalari bilan cheklangan. Agar so'rilsa, sulfanilamidlar bilan tez-tez uchraydigan tizimli nojo'ya ta'sirlar paydo bo'lishi mumkin.[4]

Farmakokinetikasi[tahrir | manbasini tahrirlash]

Kichik miqdordagi sulfanilamid mahalliy qo'llashdan keyin yoki vaginal krem yoki sham shaklida (qin shilliq qavati orqali) so'riladi. U boshqa sulfanilamidlar kabi atsetillanish orqali metabollanadi va siydik bilan chiqariladi.[4]

Yana qarang[tahrir | manbasini tahrirlash]

  • Sulfanilamid (tibbiyot)
  • Natsistlarning inson tajribasi - Sulfanilamid tajribalari
  • Eliksir sulfanilamid

Havolalar[tahrir | manbasini tahrirlash]

  • Sulfanilamides at the US National Library of Medicine Medical Subject Headings (MeSH)

Manbalar[tahrir | manbasini tahrirlash]

  1. ↑ Steinert. „The Use of Sulfanilamide in World War II“. The History of WWII Medicine (2000). 2016-yil 7-iyunda asl nusxadan arxivlangan.
  2. ↑ „Class 9 Items: Drugs, Chemicals and Biological Stains Sulfa Drugs“. Library of Congress Web Archives. 2013-yil 4-dekabrda asl nusxadan arxivlangan. Qaraldi: 2014-yil 13-iyun.
  3. ↑ „Sulfanilamide“. PubChem. National Center for Biotechnology Information (NCBI), U.S. National Library of Medicine.
  4. ↑ 4,0 4,1 4,2 4,3 4,4 4,5 4,6 4,7 Scholar, Eric (2007-01-01), Enna, S. J.; Bylund, David B. (muh.), „Sulfanilamide“, xPharm: The Comprehensive Pharmacology Reference (inglizcha), New York: Elsevier: 1–5, doi:10.1016/b978-008055232-3.62694-7, ISBN 978-0-08-055232-3, qaraldi: 2021-10-02 Manba xatosi: Invalid <ref> tag; name ":0" defined multiple times with different content
  5. ↑ „US FDA Label: AVC (sulfanilamide) Vaginal Cream 15%“. United States Food & Drug Administration. Qaraldi: 2021-yil 3-oktyabr.
  6. ↑ „Drugs@FDA: FDA-Approved Drugs“. www.accessdata.fda.gov. Qaraldi: 2021-yil 2-oktyabr.
  7. ↑ "Sulfa drug screening in yeast: fifteen sulfa drugs compete with p-aminobenzoate in Saccharomyces cerevisiae". FEMS Microbiology Letters 199 (2): 181–4. May 2001. doi:10.1111/j.1574-6968.2001.tb10671.x. PMID 11377864. 
  8. ↑ Kent, Michael. Advanced Biology. Oxford University Press, 2000 — 46 bet. ISBN 978-0-19-914195-1. 
  9. ↑ Sharma, Satyavan; Anand, Nitya (1997-01-01), Sharma, Satyavan; Anand, Nitya (muh.), „Chapter 18 - Antifolates“, Pharmacochemistry Library, Approaches to Design and Synthesis of Antiparasitic Drugs (inglizcha), Elsevier, 25: 439–454, doi:10.1016/s0165-7208(97)80040-2, ISBN 9780444894762, qaraldi: 2021-10-02
  10. ↑ 10,0 10,1 Brunton, Laurence L.. Goodman & Gilman's the pharmacological basis of therapeutics, 13th, New York: McGraw Hill Education, 2018. ISBN 978-1-259-58473-2. OCLC 993810322.  Manba xatosi: Invalid <ref> tag; name ":1" defined multiple times with different content
  11. ↑ Wormser, Gary P.; Chambers, Henry F. (2001-02-01). "The Antimicrobial Drugs, Second Edition by Eric Scholar and William Pratt New York: Oxford University Press, 2000. 607 pp., illustrated. $98.50 (cloth); $69.50 (paper)". Clinical Infectious Diseases 32 (3): 521. doi:10.1086/318515. ISSN 1058-4838. https://doi.org/10.1086/318515. 
  12. ↑ Gelmo, P. (1908). "Über Sulfamide der p-Amidobenzolsulfonsäure" (en). Journal für Praktische Chemie 77 (1): 369–382. doi:10.1002/prac.19080770129. ISSN 1521-3897. https://onlinelibrary.wiley.com/doi/abs/10.1002/prac.19080770129. 
  13. ↑ „Paul Gelmo“. Encyclopedia.com.
  14. ↑ Gelmo, Paul (May 14, 1908). "Über Sulfamide der p-Amidobenzolsulfonsäure". Journal für Praktische Chemie 77: 369–382. doi:10.1002/prac.19080770129. http://gallica.bnf.fr/ark:/12148/bpt6k90849c/f378.image. 
  15. ↑ On May 18, 1909, Deutsches Reich Patentschrift number 226,239 for sulfanilamide was awarded to Heinrich Hörlein of the Bayer corporation.
  16. ↑ "Ein Beitrag zur Chemotherapie der bakteriellen Infektionen". Deutsche Medizinische Wochenschrift 61 (7): 250. February 15, 1935. doi:10.1055/s-0028-1129486. 
  17. ↑ "Activité du p-aminophénylsulfamide sur l'infection streptococcique expérimentale de la souris et du lapin". C. R. Soc. Biol. 120: 756. November 23, 1935. 
  18. ↑ Bovet, Daniel „Les étapes de la découverte de la sulfamidochrysoïdine dans les laboratoires de recherche de la firme Bayer à Wuppertal-Elberfeld (1927–1932)“,. Une chimie qui guérit : Histoire de la découverte des sulfamides, Médecine et Société (fr). Paris: Payot, 1988 — 307 bet. 
  19. ↑ Ballentine. „Sulfanilamide Disaster“. fda.gov. FDA. Qaraldi: 2022-yil 5-may. 
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