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Pirlimycin Hydrochloride

PubChem CID
20055247
Structure
Pirlimycin Hydrochloride_small.png
Pirlimycin Hydrochloride_3D_Structure.png
Molecular Formula
Synonyms
  • Pirlimycin HCl
  • Pirlimycin hydrochloride hydrate
  • Pirlimycin Hydrochloride
  • 77495-92-2
  • UNII-8S09O559AQ
Molecular Weight
465.4 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2007-12-05
  • Modify:
    2025-01-18
Description
Pirlimycin Hydrochloride is the hydrochloride salt form of pirlimycin, a derivative of clindamycin with a 6-membered ring replacing clindamycin's 5-membered ring. Compared to clindimycin, pirlimycin has increased activity against gram-positive bacteria, including Staphylococcus aureus and coagulase negative species of Staphylococcus and Streptococcus. This agent is primarily used in the treatment of mastitis in cattle.
PIRLIMYCIN HYDROCHLORIDE is a small molecule drug that was first approved in 2001.
See also: Pirlimycin (has active moiety).

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Pirlimycin Hydrochloride.png

1.2 3D Conformer

3D Conformer of Parent

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2S,4R)-N-[(1S,2S)-2-chloro-1-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl]propyl]-4-ethylpiperidine-2-carboxamide;hydrate;hydrochloride
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

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
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

CHAZSEMQYSZBFN-RWMVMHIMSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

CC[C@@H]1CCN[C@@H](C1)C(=O)N[C@@H]([C@@H]2[C@@H]([C@@H]([C@H]([C@H](O2)SC)O)O)O)[C@H](C)Cl.O.Cl
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C17H34Cl2N2O6S
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

77495-92-2

2.3.2 UNII

2.3.3 ChEMBL ID

2.3.4 KEGG ID

2.3.5 NCI Thesaurus Code

2.3.6 Wikidata

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • cis-4-ethyl-L-picecolic acid amide of 7-deoxy-7(S)chloromethylthio lincosaminide hydrochloride
  • pirlimycin
  • pirlimycin monohydrochloride monohydrate, (2S-cis)-isomer
  • pirlimycin monohydrochloride, (2R-cis)-isomer
  • U 57930E
  • U-57930E

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
465.4 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
7
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
8
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
6
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
464.1514634 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
464.1514634 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
137 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
28
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
474
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
9
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
3
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

3.2 Chemical Classes

3.2.1 Drugs

3.2.1.1 Animal Drugs
Veterinary drugs -> Antibacterials for intramammary use -> Veterinary pharmacotherapeutic group -> EMA Drug Category
Active Ingredients (Pirlimycin Hydrochloride) -> FDA Greenbook

5 Chemical Vendors

6 Drug and Medication Information

6.1 Drug Indication

For the treatment of subclinical mastitis in lactating cows due to Gram-positive cocci susceptible to pirlimycin including staphylococcal organisms such as Staphylococcus aureus, both penicillinase-positive and penicillinase-negative, and coagulase-negative staphylococci; streptococcal organisms including Streptococcus agalactiae, Streptococcus dysgalactiae and Streptococcus uberis.

6.2 FDA Green Book

6.3 EMA Drug Information

Medicine
Category
Veterinary drugs
Active Substance
pirlimycin
INN/Common name
pirlimycin
Pharmacotherapeutic Classes
Antibacterials for intramammary use
Status
This medicine is authorized for use in the European Union
Company
Zoetis Belgium SA
Market Date
2001-01-29

7 Food Additives and Ingredients

7.1 Food Additive Classes

JECFA Functional Classes
Veterinary Drug -> ANTIMICROBIAL_AGENT;

7.2 Evaluations of the Joint FAO / WHO Expert Committee on Food Additives - JECFA

Chemical Name
PIRSUE STERILE SOLUTION
Evaluation Year
2004
ADI
0–8 µg/kg bw/d
Comments
The Committee noted that pirlimycin belongs to the class of lincosamide antibiotics that are known to be associated with perturbation of the gastrointestinal microflora following administration in humans. The ADI based on MIC data was considered to be extremely conservative considering the findings in a hamster model of pseudomembranous colitis and in humans. Therefore, the Committee established a microbiological ADI of 0–8 µg/kg bw/d on the basis of the NOEL for gastrointestinal effects in humans of 50 mg (0.83 mg/kg bw for a 60-kg adult) and a safety factor of 100, rounded to one significant figure.
Tox Monograph

8 Pharmacology and Biochemistry

8.1 ATC Code

QJ51FF90

9 Use and Manufacturing

9.1 Uses

9.1.1 Use Classification

Veterinary drugs -> Antibacterials for intramammary use -> Veterinary pharmacotherapeutic group -> EMA Drug Category
Animal Drugs -> FDA Approved Animal Drug Products (Green Book) -> Active Ingredients
Veterinary Drug -> ANTIMICROBIAL_AGENT; -> JECFA Functional Classes

10 Literature

10.1 Consolidated References

10.2 NLM Curated PubMed Citations

10.3 Springer Nature References

10.4 Chemical Co-Occurrences in Literature

10.5 Chemical-Gene Co-Occurrences in Literature

10.6 Chemical-Disease Co-Occurrences in Literature

11 Patents

11.1 Depositor-Supplied Patent Identifiers

11.2 WIPO PATENTSCOPE

11.3 FDA Green Book Patents

12 Classification

12.1 MeSH Tree

12.2 NCI Thesaurus Tree

12.3 KEGG: Drug Groups

12.4 KEGG : Antimicrobials

12.5 ChemIDplus

12.6 MolGenie Organic Chemistry Ontology

13 Information Sources

  1. ChEMBL
    LICENSE
    Access to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/).
    http://www.ebi.ac.uk/Information/termsofuse.html
  2. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  3. FDA Global Substance Registration System (GSRS)
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  4. European Medicines Agency (EMA)
    LICENSE
    Information on the European Medicines Agency's (EMA) website is subject to a disclaimer and copyright and limited reproduction notices.
    https://www.ema.europa.eu/en/about-us/legal-notice
  5. FDA Approved Animal Drug Products (Green Book)
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  6. Joint FAO/WHO Expert Committee on Food Additives (JECFA)
    LICENSE
    Permission from WHO is not required for the use of WHO materials issued under the Creative Commons Attribution-NonCommercial-ShareAlike 3.0 Intergovernmental Organization (CC BY-NC-SA 3.0 IGO) licence.
    https://www.who.int/about/policies/publishing/copyright
  7. KEGG
    LICENSE
    Academic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial license
    https://www.kegg.jp/kegg/legal.html
  8. NCI Thesaurus (NCIt)
    LICENSE
    Unless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute as the source.
    https://www.cancer.gov/policies/copyright-reuse
  9. Open Targets
    LICENSE
    Datasets generated by the Open Targets Platform are freely available for download.
    https://platform-docs.opentargets.org/licence
  10. Springer Nature
  11. Wikidata
    pirlimycin hydrochloride hydrate
    https://www.wikidata.org/wiki/Q27270945
  12. PubChem
  13. Medical Subject Headings (MeSH)
    LICENSE
    Works produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.
    https://www.nlm.nih.gov/copyright.html
  14. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  15. PATENTSCOPE (WIPO)
CONTENTS