Pirlimycin

Chemical compound

Pharmaceutical compound

Pirlimycin
Clinical data
Structural formula
Space-filling model of pirlimycin molecule
Trade names	Pirsue
Routes of administration	Intramammary
ATCvet code	QJ51FF90 (WHO )
Legal status
Legal status	EU: Rx-only^[1]^[2]
Identifiers
IUPAC name Methyl (2S-cis)-7-chloro-6,7,8-trideoxy-6[[(4-ethyl-2-piperidinyl)carbonyl]amino]-1-thio-L-threo-α-D-galacto-octopyranoside
CAS Number	79548-73-5 ^checkY
ChemSpider	138508 ^☒N
UNII	LM19JT6G5K 8S09O559AQ
KEGG	D08391 ^checkY D05501
ChEMBL	ChEMBL1652611 ^☒N ChEMBL3989899
CompTox Dashboard (EPA)	DTXSID30904249 Edit this at Wikidata
Chemical and physical data
Formula	C₁₇H₃₁ClN₂O₅S
Molar mass	410.95 g·mol⁻¹
3D model (JSmol)	Interactive image
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
InChI InChI=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^☒N Key:HBJOXQRURQPDEX-MHXMMLMNSA-N^☒N Key:CHAZSEMQYSZBFN-RWMVMHIMSA-N
^☒NcheckY (what is this?) (verify)

Pirlimycin, sold under the brand name Pirsue, is used in the treatment of mastitis in cattle.^[1]^[3]^[4] It is used as the salt pirlimycin hydrochloride and it belongs to the lincosamide class of antimicrobials.^[1]

Activity

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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.^[5]

Mechanism of action

[edit ]

It is bacteriostatic and acts by inhibiting bacterial protein synthesis via binding with the 50S subunit of the ribosome.^{[citation needed ]}

References

[edit ]

^ ^a ^b ^c "Pirsue EPAR". European Medicines Agency (EMA). 29 January 2001. Retrieved 26 December 2024.
^ "Pirsue PI". Union Register of medicinal products. 31 January 2001. Retrieved 26 December 2024.
^ Thornsberry C, Marler JK, Watts JL, Yancey RJ (May 1993). "Activity of pirlimycin against pathogens from cows with mastitis and recommendations for disk diffusion tests". Antimicrobial Agents and Chemotherapy. 37 (5): 1122–6. doi:10.1128/AAC.37.5.1122. PMC 187914 . PMID 8517701.
^ Hogeveen H (2005). Mastitis in dairy production: current knowledge and future solutions. Wageningen: Wageningen Academic Publishers. p. 55. ISBN 978-90-76998-70-1.
^ "USP: Pirlimycin" (PDF). Archived from the original (PDF) on 9 May 2009. Retrieved 28 June 2009.

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Antibacterials that inhibit protein synthesis (J01A, J01B, J01F, J01G, QJ01XQ)

30S

Aminoglycosides
(initiation inhibitors)

-mycin (Streptomyces )	Streptomycin ^# Dihydrostreptomycin Neomycin ^# Framycetin Paromomycin ^# Ribostamycin Kanamycin Amikacin ^# Arbekacin Bekanamycin Dibekacin Tobramycin (+loteprednol) Spectinomycin ^# Hygromycin B Totomycin Apramycin Nourseothricin
-micin (Micromonospora )	Gentamicin ^# Netilmicin Sisomicin Micronomicin Plazomicin ^# Isepamicin Verdamicin Astromicin
other	Butirosin

Tetracycline antibiotics
(tRNA binding)

Tetracyclines	Doxycycline ^# Chlortetracycline Clomocycline Demeclocycline Eravacycline Lymecycline Meclocycline ^‡ Metacycline Minocycline Omadacycline Oxytetracycline Penimepicycline Rolitetracycline Sarecycline Tetracycline ^#
Glycylcyclines	Tigecycline

50S

Oxazolidinone
(initiation inhibitors)

Peptidyl transferase

Amphenicols	Chloramphenicol ^# Azidamfenicol Thiamphenicol Florfenicol

MLS (transpeptidation/translocation)

Macrolides	Boromycin Carbomycin Carrimycin Clarithromycin ^# Dirithromycin Erythromycin ^# Flurithromycin Josamycin Kitasamycin Midecamycin Miocamycin Nafithromycin Oleandomycin Rokitamycin Roxithromycin Spiramycin Tildipirosin Tilmicosin Troleandomycin Tylosin Tylvalosin
Azalides	Azithromycin ^# Gamithromycin Tulathromycin
Ketolides	Telithromycin ^‡ Cethromycin Solithromycin ^†
Lincosamides	Clindamycin ^# Lincomycin Pirlimycin
Oxepanoprolinamides	Cresomycin Iboxamycin
Streptogramins	Pristinamycin (IA, IIA, IIB) NXL103 (Flopristin, Linopristin) Quinupristin/dalfopristin (Dalfopristin, Quinupristin) Streptogramin A Streptogramin B Virginiamycin (S1)

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

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