{{Short description|Chemical compound}} {{Use dmy dates|date=December 2024}} {{cs1 config |name-list-style=vanc |display-authors=6}} {{Infobox drug | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 408712002 | image = Pirlimycin structure.svg | image_class = skin-invert-image | alt = Structural formula | image2 = Pirlimycin molecule spacefill.png | image_class2 = bg-transparent | alt2 = Space-filling model of pirlimycin molecule
<!-- Clinical data --> | pronounce = | tradename = Pirsue | Drugs.com = | MedlinePlus = | DailyMedID = <!-- DailyMed may use generic or brand name (generic name preferred) --> | pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> | pregnancy_AU_comment = | pregnancy_category = | routes_of_administration = Intramammary | class = | ATCvet = yes | ATC_prefix = J51 | ATC_suffix = FF90 | ATC_supplemental =
<!-- Legal status --> | legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled --> | legal_AU_comment = | legal_BR = <!-- OTC, A1, A2, A3, B1, B2, C1, C2, C3, C5, D1, D2, E, F1, F2, F3, F4 --> | legal_BR_comment = | legal_CA = <!-- OTC, Rx-only, Schedule I, II, III, IV, V, VI, VII, VIII --> | legal_CA_comment = | legal_DE = <!-- Anlage I, II, III or Unscheduled --> | legal_DE_comment = | legal_NZ = <!-- Class A, B, C --> | legal_NZ_comment = | legal_UK = <!-- GSL, P, POM, CD, CD Lic, CD POM, CD No Reg POM, CD (Benz) POM, CD (Anab) POM or CD Inv POM / Class A, B, C --> | legal_UK_comment = | legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> | legal_US_comment = | legal_EU = Rx-only | legal_EU_comment = <ref name="Pirsue EPAR">{{cite web | title=Pirsue EPAR | website=European Medicines Agency (EMA) | date=29 January 2001 | url=https://www.ema.europa.eu/en/medicines/veterinary/EPAR/pirsue | access-date=26 December 2024}}</ref><ref>{{cite web | title=Pirsue PI | website=Union Register of medicinal products | date=31 January 2001 | url=https://ec.europa.eu/health/documents/community-register/html/v027.htm | access-date=26 December 2024}}</ref> | legal_UN = <!-- N I, II, III, IV / P I, II, III, IV --> | legal_UN_comment = | legal_status = <!-- For countries not listed above -->
<!-- Pharmacokinetic data --> | bioavailability = | protein_bound = | metabolism = | metabolites = | onset = | elimination_half-life = | duration_of_action = | excretion =
<!-- Identifiers --> | CAS_number_Ref = {{cascite|correct|??}} | CAS_number = 79548-73-5 | CAS_supplemental = | PubChem = | IUPHAR_ligand = | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank = | ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} | ChemSpiderID = 138508 | UNII_Ref = {{fdacite|changed|FDA}} | UNII = LM19JT6G5K | UNII2 = 8S09O559AQ | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = D08391 | KEGG2 = D05501 | ChEBI = | ChEMBL_Ref = {{ebicite|changed|EBI}} | ChEMBL = 1652611 | ChEMBL2 = 3989899 | NIAID_ChemDB = | PDB_ligand = | synonyms =
<!-- Chemical and physical data --> | IUPAC_name = Methyl (2''S''-''cis'')-7-chloro-6,7,8-trideoxy-6<nowiki>[[</nowiki>(4-ethyl-2-piperidinyl)carbonyl]amino]-1-thio-<small>L</small>-threo-α-<small>D</small>-galacto-octopyranoside | C=17 | H=31 | Cl=1 | N=2 | O=5 | S=1 | SMILES = CC[C@@H]1CCN[C@@H](C1)C(=O)N[C@@H]([C@@H]2[C@@H]([C@@H]([C@H]([C@H](O2)SC)O)O)O)[C@H](C)Cl | StdInChI_Ref = {{stdinchicite|changed|chemspider}} | StdInChI = 1S/C17H31ClN2O5S/c1-4-9-5-6-19-10(7-9)16(24)20-11(8(2)18)15-13(22)12(21)14(23)17(25-15)26-3/h8-15,17,19,21-23H,4-7H2,1-3H3,(H,20,24)/t8-,9+,10-,11+,12-,13+,14+,15+,17+/m0/s1 | StdInChI_comment = | StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} | StdInChIKey = HBJOXQRURQPDEX-MHXMMLMNSA-N | StdInChIKey2 = CHAZSEMQYSZBFN-RWMVMHIMSA-N | density = | density_notes = | melting_point = | melting_high = | melting_notes = | boiling_point = | boiling_notes = | solubility = | sol_units = | specific_rotation = }}
'''Pirlimycin''', sold under the brand name '''Pirsue''', is used in the treatment of mastitis in cattle.<ref name="Pirsue EPAR" /><ref name="Thornsberry_1993">{{cite journal | vauthors = Thornsberry C, Marler JK, Watts JL, Yancey RJ | title = Activity of pirlimycin against pathogens from cows with mastitis and recommendations for disk diffusion tests | journal = Antimicrobial Agents and Chemotherapy | volume = 37 | issue = 5 | pages = 1122–6 | date = May 1993 | pmid = 8517701 | pmc = 187914 | doi = 10.1128/AAC.37.5.1122 }}</ref><ref>{{cite book | vauthors = Hogeveen H |title=Mastitis in dairy production: current knowledge and future solutions |date=2005 |publisher=Wageningen Academic Publishers |location=Wageningen |isbn=978-90-76998-70-1 |page=55 |url=https://books.google.com/books?id=9hOA_wWF9iEC&dq=Pirlimycin&pg=PA55}}</ref> It is used as the salt pirlimycin hydrochloride and it belongs to the lincosamide class of antimicrobials.<ref name="Pirsue EPAR" /> __TOC__
==Activity== Pirlimycin is active against Gram-positive bacteria, specifically ''Staphylococcus aureus'' and coagulase negative species of ''Staphylococcus'' and ''Streptococcus''. It has no activity against Gram-negative bacteria.<ref>{{Cite web |url=http://www.usp.org/pdf/EN/veterinary/pirlimycin.pdf |title=USP: Pirlimycin |access-date=2009-06-28 |archive-url=https://web.archive.org/web/20090509031543/http://www.usp.org/pdf/EN/veterinary/pirlimycin.pdf |archive-date=2009-05-09 |url-status=dead }}</ref>
==Mechanism of action== It is bacteriostatic and acts by inhibiting bacterial protein synthesis via binding with the 50S subunit of the ribosome.{{cn|date=January 2023}}
==References== {{Reflist}}
{{Protein synthesis inhibitor antibiotics}} {{Portal bar | Medicine}} {{Authority control}}
Category:Lincosamides Category:Veterinary drugs Category:Organochlorides
{{antibiotic-stub}}