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

[H][C@@](NC(=O)[C@@H]1C[C@H](CC)CCN1)([C@H](C)Cl)[C@@]2([H])O[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 179 Target ID: CHEMBL2363135 Sources: https://ec.europa.eu/health/documents/community-register/2012/20121024124731/anx_124731_en.pdf	Inhibitor 8297

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 8429	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

PubMed

Title	Date	PubMed
In vitro activity of U-57930E against anaerobic bacteria and its comparison with clindamycin, ampicillin, carbenicillin and tetracycline.	1983 Jan	6678915
Susceptibility of bacteria to serum lysis or phagocytosis following growth in subinhibitory levels of lincosaminide or spectinomycin related antibiotics.	1986 Jul	2944862
Purification of lincosaminide O-nucleotidyltransferase from Streptomyces coelicolor Müller.	1991 Aug	1655688
Effect of precalving intramammary treatment with pirlimycin in nulliparous Holstein heifers.	2007 Oct	17955903
Quantum mechanical studies of lincosamides.	2012 Jun	22116607
Effect of lactation therapy on Staphylococcus aureus transmission dynamics in two commercial dairy herds.	2013 Feb 11	23398676

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 `Fri Dec 15 16:19:13 GMT 2023` Edited by `admin` on `Fri Dec 15 16:19:13 GMT 2023`
Record UNII	LM19JT6G5K
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

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

PIRSUE

Brand 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