NAV

Pirlimycin

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

Identification

Generic Name
Pirlimycin
DrugBank Accession Number
DB11537
Background

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

Type
Small Molecule
Groups
Vet approved
Structure
3D
Similar Structures
Weight
Average: 410.95
Monoisotopic: 410.164221
Chemical Formula
C17H31ClN2O5S
Synonyms
  • Pirlimycin
  • Pirlimycina
  • Pirlimycine
  • Pirlimycinum
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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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

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
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interactions in your software
AcenocoumarolThe risk or severity of bleeding can be increased when Pirlimycin is combined with Acenocoumarol.
AcetophenazineAcetophenazine may increase the neurotoxic activities of Pirlimycin.
AlimemazineAlimemazine may increase the neurotoxic activities of Pirlimycin.
AmbroxolThe risk or severity of methemoglobinemia can be increased when Pirlimycin is combined with Ambroxol.
AmisulprideAmisulpride may increase the neurotoxic activities of Pirlimycin.
Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Pirlimycin hydrochloride8S09O559AQ77495-92-2CHAZSEMQYSZBFN-RWMVMHIMSA-N
International/Other Brands
Pirsue

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
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
2-piperidinecarboxamide / Alcohol / Aliphatic heteromonocyclic compound / Alkyl chloride / Alkyl halide / Alpha-amino acid amide / Amine / Azacycle / Carbonyl group / Carboxamide group
show 25 more
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
LM19JT6G5K
CAS number
79548-73-5
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-carboxamide
SMILES
[H][C@@](NC(=O)[C@@H]1C[C@H](CC)CCN1)([C@H](C)Cl)[C@@]1([H])O[C@H](SC)[C@H](O)[C@@H](O)[C@H]1O

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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  10. Theis DL: Ion-pairing liquid chromatographic method for the determination of pirlimycin hydrochloride. J Chromatogr. 1987 Jul 31;402:335-43. [Article]
KEGG Drug
D08391
ChemSpider
138508
RxNav
1367292
ChEMBL
CHEMBL1652611
ZINC
ZINC000005651187
Wikipedia
Pirlimycin

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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 Solubility3.53 mg/mLALOGPS
logP1.55ALOGPS
logP0.58Chemaxon
logS-2.1ALOGPS
pKa (Strongest Acidic)12.41Chemaxon
pKa (Strongest Basic)8.88Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count6Chemaxon
Hydrogen Donor Count5Chemaxon
Polar Surface Area111.05 Å2Chemaxon
Rotatable Bond Count6Chemaxon
Refractivity100.5 m3·mol-1Chemaxon
Polarizability42.35 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
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/MSsplash10-03di-0400900000-1841948f5e5f1f33ff1b
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-0017900000-6dc6830f299758d86d52
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-0933100000-bfae658b3c09a93c8e02
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-6966600000-72c3264695f364c8aeb0
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-9400000000-7e53b59bff07f3b38ce5
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-9752000000-97d06131faf6a4b01838
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-172.96135
predicted
DeepCCS 1.0 (2019)
[M+H]+174.87895
predicted
DeepCCS 1.0 (2019)
[M+Na]+181.06163
predicted
DeepCCS 1.0 (2019)

Drug created at February 26, 2016 17:38 / Updated at February 21, 2021 18:53