Pirlimycin

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

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Name
Pirlimycin
Accession Number
DB11537
Type
Small Molecule
Groups
Vet approved
Description

Pirlimycin hydrochloride is an antibiotic belonging to the lincosamide class. Often marketed as Pirsue, this drug is used to treat mastitis in cattle.

Structure
Thumb
Synonyms
Not Available
Product Ingredients
IngredientUNIICASInChI Key
Pirlimycin hydrochloride8S09O559AQ77495-92-2CHAZSEMQYSZBFN-RWMVMHIMSA-N
International/Other Brands
Pirsue
Categories
UNII
LM19JT6G5K
CAS number
79548-73-5
Weight
Average: 410.95
Monoisotopic: 410.164221
Chemical Formula
C17H31ClN2O5S
InChI Key
HBJOXQRURQPDEX-MHXMMLMNSA-N
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
IUPAC Name
(2S,4R)-N-[(1S,2S)-2-chloro-1-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(methylsulfanyl)oxan-2-yl]propyl]-4-ethylpiperidine-2-carboximidic acid
SMILES
[H][C@@](C)(Cl)[C@@]([H])(N=C(O)[C@]1([H])C[C@]([H])(CC)CCN1)[C@@]1([H])O[C@]([H])(SC)[C@]([H])(O)[C@@]([H])(O)[C@@]1([H])O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
Not Available
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe risk or severity of bleeding can be increased when Pirlimycin is combined with (R)-warfarin.
(S)-WarfarinThe risk or severity of bleeding can be increased when Pirlimycin is combined with (S)-Warfarin.
4-hydroxycoumarinThe risk or severity of bleeding can be increased when Pirlimycin is combined with 4-hydroxycoumarin.
AcenocoumarolThe risk or severity of bleeding can be increased when Pirlimycin is combined with Acenocoumarol.
AcepromazineAcepromazine may increase the neurotoxic activities of Pirlimycin.
AceprometazineAceprometazine may increase the neurotoxic activities of Pirlimycin.
AcetophenazineAcetophenazine may increase the neurotoxic activities of Pirlimycin.
Adenovirus type 7 vaccine liveThe therapeutic efficacy of Adenovirus type 7 vaccine live can be decreased when used in combination with Pirlimycin.
AlcuroniumThe risk or severity of neuromuscular blockade can be increased when Pirlimycin is combined with Alcuronium.
AlimemazineAlimemazine may increase the neurotoxic activities of Pirlimycin.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
Not Available

References

General References
  1. Hornish RE, Roof RD, Wiest JR: Pirlimycin residue in bovine liver--a case of reverse metabolism. Analyst. 1998 Dec;123(12):2463-7. [PubMed:10435279]
  2. Thornsberry C, Marler JK, Watts JL, Yancey RJ Jr: Activity of pirlimycin against pathogens from cows with mastitis and recommendations for disk diffusion tests. Antimicrob Agents Chemother. 1993 May;37(5):1122-6. [PubMed:8517701]
  3. Heller DN: Determination of pirlimycin residue in milk by liquid chromatographic analysis of the 9-fluorenylmethyl chloroformate derivative. J AOAC Int. 1997 Sep-Oct;80(5):975-81. [PubMed:9325575]
  4. Shah JA, Weber DJ: High-performance liquid chromatographic assay of pirlimycin in human serum and urine using 9-fluorenylmethylchloroformate. J Chromatogr. 1984 Jul 13;309(1):95-105. [PubMed:6480775]
  5. Oliver SP, Gillespie BE, Ivey SJ, Lewis MJ, Johnson DL, Lamar KC, Moorehead H, Dowlen HH, Chester ST, Hallberg JW: Influence of prepartum pirlimycin hydrochloride or penicillin-novobiocin therapy on mastitis in heifers during early lactation. J Dairy Sci. 2004 Jun;87(6):1727-31. [PubMed:15453485]
  6. Whittem T: Pharmacokinetics and milk discard times of pirlimycin after intramammary infusion: a population approach. J Vet Pharmacol Ther. 1999 Feb;22(1):41-51. [PubMed:10211716]
  7. Kopia GA, Driscoll EM, Yeung KF, Lucchesi BR: Antiarrhythmic and cardiovascular actions of the new antibiotic agent pirlimycin adenylate. Pharmacology. 1983;27(5):255-66. [PubMed:6606809]
  8. Deluyker HA, Van Oye SN, Boucher JF: Factors affecting cure and somatic cell count after pirlimycin treatment of subclinical mastitis in lactating cows. J Dairy Sci. 2005 Feb;88(2):604-14. [PubMed:15653527]
  9. Evans ME, Patterson LS, Stratton CW: In vitro comparison of clindamycin and pirlimycin (U-57930E) activity against Staphylococcus aureus. Antimicrob Agents Chemother. 1982 Aug;22(2):334-5. [PubMed:6927639]
  10. Theis DL: Ion-pairing liquid chromatographic method for the determination of pirlimycin hydrochloride. J Chromatogr. 1987 Jul 31;402:335-43. [PubMed:3654872]
External Links
KEGG Drug
D08391
ChemSpider
138508
ChEMBL
CHEMBL1652611
Wikipedia
Pirlimycin

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.466 mg/mLALOGPS
logP1.65ALOGPS
logP-1.1ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)3.26ChemAxon
pKa (Strongest Basic)8.81ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area114.54 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity101.02 m3·mol-1ChemAxon
Polarizability43.16 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as alpha amino acid amides. These are amide derivatives of alpha amino acids.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Alpha amino acid amides
Alternative Parents
Thioglycosides / Piperidinecarboxamides / Oxanes / Monosaccharides / Monothioacetals / Secondary carboxylic acid amides / Secondary alcohols / Sulfenyl compounds / Polyols / Oxacyclic compounds
show 8 more
Substituents
Alpha-amino acid amide / Glycosyl compound / S-glycosyl compound / 2-piperidinecarboxamide / Piperidinecarboxamide / Monosaccharide / Oxane / Piperidine / Monothioacetal / Secondary carboxylic acid amide
show 25 more
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
Not Available

Drug created on February 26, 2016 10:38 / Updated on June 04, 2019 07:23