PLEUROMULIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C22H34O5
Molecular Weight	378.5024
Optical Activity	UNSPECIFIED
Defined Stereocenters	8 / 8
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]12C(=O)CC[C@]13CC[C@@H](C)[C@@]2(C)[C@@H](C[C@@](C)(C=C)[C@@H](O)[C@@H]3C)OC(=O)CO

InChI

InChIKey=ZRZNJUXESFHSIO-BKUNHTPHSA-N

InChI=1S/C22H34O5/c1-6-20(4)11-16(27-17(25)12-23)21(5)13(2)7-9-22(14(3)19(20)26)10-8-15(24)18(21)22/h6,13-14,16,18-19,23,26H,1,7-12H2,2-5H3/t13-,14+,16-,18+,19+,20-,21+,22+/m1/s1

HIDE SMILES / InChI

Description
Sources: http://www.ncbi.nlm.nih.gov/pubmed/16589015
Curator's Comment: Description was created based on several sources, including: https://www.ncbi.nlm.nih.gov/pubmed/22191527;

Pleuromulin (pleuromulitin) is a natural antibiotic isolated from Basidiomycete Pleurotus. Pleuromulitin exhibits activity mainly against gram-positive bacteria including S. aureus, Klebasiella pneumoniae and Bacillus Subtilis. Pleuromulin is an organic compound which is not reported to be used in as a drug however its derivatives have been used in treatment of infections. The first pleuromulitin that was approved in 1979 for use in veterinary medicine was semi-synthetic derivative tiamulin. Semisynthetic pleuromutilin retapamulin (ALTABAX, GlaxoSmithKline) was the first approved for topical use in humans in 2007. Another derivative of pleuromulin, Lefamulin has been successfully tested in phase 1 clinical trial for systemic use in patients (Nabriva Therapeutics AG).

Originator

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
Chemical studies with pleuromutilin.	1952 Nov	12999825

Patents

Sample Use Guides

In Vivo Use Guide

as a single dose (at 50 mg./kg) or as three doses per day (25 mg/kg or 50 mg/kg) for as long as the mice survived

Route of Administration: Other

In Vitro Use Guide

At 0.25 - 2 ug/ml pleuromulin was bacteriostatic for S. aureus, at 4 ug/ml was bacterisidal

Name

Type

Language

PLEUROMULIN

Official Name

English

GLYCOLIC ACID, 8-ESTER WITH OCTAHYDRO-5,8-DIHYDROXY-4,6,9,10-TETRAMETHYL-6-VINYL-3A,9-PROPANO-3AH-CYCLOPENTACYCLOOCTEN-1(4H)-ONE

Common Name

English

PLEUROMUTILIN

Common Name

English

ACETIC ACID, HYDROXY-, (3AS,4R,5S,6S,8R,9R,9AR,10R)-6-ETHENYLDECAHYDRO-5-HYDROXY-4,6,9,10-TETRAMETHYL-1-OXO-3A,9-PROPANO-3AH-CYCLOPENTACYCLOOCTEN-8-YL ESTER

Common Name

English

DROSOPHILIN B

Common Name

English

PLEUROMUTILIN [MI]

Common Name

English

NSC-121145

Code

English

GLYCOLIC ACID 8-ESTER WITH OCTAHYDRO-5,8-DIHYDROXY-4,6,9,10-TETRAMETHYL-6-VINYL-3A,9-PROPANO-3AH-CYCLOPENTACYCLOOCTEN-1(4H)-ONE

Common Name

English

MUTILIN 14-GLYCOLATE

Common Name

English

(3aS,4R,5S,6S,8R,9R,9aR,10R)6-ethenyl-5-hydroxy-4,6,9,10-tetramethyl-1-oxodecahydro-3a,9-propano-3aH-cyclopenta[8]annulen-8-yl 2-hydroxyacetate

Systematic Name

English

PLEUROMUTILIN [USP IMPURITY]

Common Name

English

14-DEOXY-14-((HYDROXYACETYL)OXY)MUTILIN

Common Name

English

(+)-PLEUROMUTILIN

Common Name

English

ACETIC ACID, 2-HYDROXY-, (3AS,4R,5S,6S,8R,9R,9AR,10R)-6-ETHENYLDECAHYDRO-5-HYDROXY-4,6,9,10-TETRAMETHYL-1-OXO-3A,9-PROPANO-3AH-CYCLOPENTACYCLOOCTEN-8-YL ESTER

Common Name

English

ANTIBIOTIC A 40104C

Common Name

English

BC-757

Code

English

pleuromulin [INN]

Common Name

English

VALNEMULIN HYDROCHLORIDE IMPURITY E [EP IMPURITY]

Common Name

English

ACETIC ACID, HYDROXY-, 6-ETHENYLDECAHYDRO-5-HYDROXY-4,6,9,10-TETRAMETHYL-1-OXO-3A,9-PROPANO-3AH-CYCLOPENTACYCLOOCTEN-8-YL ESTER, (3AS-(3A.ALPHA.,4.BETA.,5.ALPHA.,6.ALPHA.,8.BETA.,9.ALPHA.,9A.BETA.,10S*))-

Common Name

English

Code System Code Type Description

CAS

125-65-5