PIRLIMYCIN HYDROCHLORIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C17H31ClN2O5S.ClH.H2O
Molecular Weight	465.433
Optical Activity	UNSPECIFIED
Defined Stereocenters	9 / 9
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O.Cl.[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=CHAZSEMQYSZBFN-RWMVMHIMSA-N

InChI=1S/C17H31ClN2O5S.ClH.H2O/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);1H;1H2/t8-,9+,10-,11+,12-,13+,14+,15+,17+;;/m0../s1

HIDE SMILES / InChI

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 pipecolic acid amide of clindamycin (U-57930E) on anaerobic bacteria compared with those of clindamycin, cefoxitin, and chloramphenicol.	1982 Aug	6927289
In vitro activity of U-57930E, a new clindamycin analog, against aerobic gram-positive bacteria.	1982 Jun	7114838
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).

Name

Type

Language

PIRLIMYCIN HYDROCHLORIDE

Official Name

English

PIRLIMYCIN HYDROCHLORIDE [GREEN BOOK]

Common Name

English

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

Common Name

English

PIRLIMYCIN HCL

Common Name

English

PIRLIMYCIN HYDROCHLORIDE [USAN]

Common Name

English

PIRLIMYCIN HYDROCHLORIDE HYDRATE [JAN]

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-, MONOHYDROCHLORIDE, MONOHYDRATE, (2S-CIS)-

Common Name

English

U-57,930E

Code

English

U-57930E

Code

English

PIRLIMYCIN HYDROCHLORIDE MONOHYDRATE

Common Name

English

PIRLIMYCIN HYDROCHLORIDE [MART.]

Common Name

English

PIRLIMYCIN HYDROCHLORIDE HYDRATE

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C82922