PIRLIMYCIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C17H31ClN2O5S
Molecular Weight	410.956
Optical Activity	UNSPECIFIED
Defined Stereocenters	9 / 9
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC[C@@H]1CCN[C@@H](C1)C(=O)N[C@H]([C@H](C)Cl)[C@H]2O[C@H](SC)[C@H](O)[C@@H](O)[C@H]2O

InChI

InChIKey=HBJOXQRURQPDEX-MHXMMLMNSA-N

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

HIDE SMILES / InChI

Molecular Formula	C17H31ClN2O5S
Molecular Weight	410.956
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	9 / 9
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://ec.europa.eu/health/documents/community-register/2012/20121024124731/anx_124731_en.pdf | https://web.archive.org/web/20171115071729/https://www.fda.gov/downloads/AnimalVeterinary/Products/ApprovedAnimalDrugProducts/FOIADrugSummaries/ucm116138.pdf

Pirlimycin is an antibiotic which was approved in the US and Europe for the treatment of subclinical mastitis in lactating dairy cattle associated with common mastitis pathogens, mostly Gram-positive bacterias. The drug exerts its action by binding to the 50S ribosomal subunit, therefore hindering the aminoacyl-tRNA binding and inhibiting the peptidyltransferase reaction, which interferes with protein synthesis within the bacteria.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Bacterial 70S ribosome 180 Target ID: CHEMBL2363135 Sources: https://ec.europa.eu/health/documents/community-register/2012/20121024124731/anx_124731_en.pdf	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Sub-clinical mastitis 5 Sources: https://web.archive.org/web/20171115071729/https://www.fda.gov/downloads/AnimalVeterinary/Products/ApprovedAnimalDrugProducts/FOIADrugSummaries/ucm116138.pdf	Curative		Approved 8583	PIRSUE Approved Use PIRSUE Sterile Solution (pirlimycin hydrochloride) is indicated for the treatment of clinical and subclinical mastitis in lactating dairy cattle associated with Staphylococcus species such as Staphylococcus aureus and Streptococcus species such as Streptococcus agalactiae, Streptococcus dysgalactiae, and Streptococcus uberis. Launch Date 1993

AUC

Value	Dose	Co-administered	Analyte	Population
2592 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6480775/	500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered:		PIRLIMYCIN serum	Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN
44.5 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6480775/	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:		PIRLIMYCIN serum	Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN

PubMed

Title	Date	PubMed
Effect of lactation therapy on Staphylococcus aureus transmission dynamics in two commercial dairy herds.	2013-02-11	23398676
Quantum mechanical studies of lincosamides.	2012-06	22116607
Effect of precalving intramammary treatment with pirlimycin in nulliparous Holstein heifers.	2007-10	17955903
Purification of lincosaminide O-nucleotidyltransferase from Streptomyces coelicolor Müller.	1991-08	1655688
Susceptibility of bacteria to serum lysis or phagocytosis following growth in subinhibitory levels of lincosaminide or spectinomycin related antibiotics.	1986-07	2944862
In vitro activity of U-57930E against anaerobic bacteria and its comparison with clindamycin, ampicillin, carbenicillin and tetracycline.	1983-01	6678915
In vitro activity of pipecolic acid amide of clindamycin (U-57930E) on anaerobic bacteria compared with those of clindamycin, cefoxitin, and chloramphenicol.	1982-08	6927289
In vitro activity of U-57930E, a new clindamycin analog, against aerobic gram-positive bacteria.	1982-06	7114838

Patents

Sample Use Guides

In Vivo Use Guide

Infuse the contents of one syringe (1 syringe contains pirlimycin hydrochloride equivalent to 50 mg pirlimycin (5 mg/ml)) into each affected quarter by intramammary infusion. Repeat this treatment once, after a 24-hour interval.

Route of Administration: Other

In Vitro Use Guide

Subcultures (0.15 ml) from the clear wells inoculated onto blood agar plates were examined after 24 and 48 h of incubation with pirlimycin at 37C. MIC50 values were 0.5 ug/ml (Staphylococcus aureus, methicillin susceptible); 2 ug/ml (Staphylococcus aureus, methicillin resistant); 1 ug/ml (Staphylococcus sp.); 0.25 ug/ml (Streptococcus pyogenes); 0.5 ug/ml (Streptococcus agalactiae); 0.25 ug/ml (Streptococcus pneumoniae, penicillin susceptible); 0.5 ug/ml (Streptococcus viridans).

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:24:59 GMT 2025` Edited by `admin` on `Mon Mar 31 18:24:59 GMT 2025`
Record UNII	LM19JT6G5K
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PIRSUE

Preferred Name

English

PIRLIMYCIN

Official Name

English

METHYL 7-CHLORO-6,7,8-TRIDEOXY-6-CIS-4-ETHYL-L-PIPECOLAMIDO)-1-THIO-L-THREO-.ALPHA.-D-GALACTO-OCTOPYRANOSIDE

Common Name

English

L-THREO-.ALPHA.-D-GALACTO-OCTOPYRANOSIDE, METHYL 7-CHLORO-6,7,8-TRIDEOXY-6-(((4-ETHYL-2-PIPERIDINYL)CARBONYL)AMINO)-1-THIO-

Common Name

English

PIRLIMYCIN [MI]

Common Name

English

pirlimycin [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C82922