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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 of PLEUROMULIN

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
Molecular Formula C22H34O5
Molecular Weight 378.5024
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 8 / 8
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
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

Columbia University|The New York Botanical Garden
1
Curator's Comment: Pleuromutilins were discovered as natural-product antibiotics in 1950.

Approval Year

Unknown
139594
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Chemical studies with pleuromutilin.
1952 Nov
Patents

Patents

9120727
1
WO2007062335A2
1

Sample Use Guides

In Vivo Use Guide
Curator's Comment: Treatment of infected with Streptococcus hemoliticus mice
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
Substance Class Chemical
Created
by admin
on Sat Dec 16 16:59:59 UTC 2023
Edited
by admin
on Sat Dec 16 16:59:59 UTC 2023
Record UNII
3DE4A80MZ1
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PLEUROMULIN
INN  
INN  
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
MI  
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
Created by admin on Sat Dec 16 17:00:01 UTC 2023 , Edited by admin on Sat Dec 16 17:00:01 UTC 2023
PRIMARY
SMS_ID
100000081913
Created by admin on Sat Dec 16 17:00:01 UTC 2023 , Edited by admin on Sat Dec 16 17:00:01 UTC 2023
PRIMARY
INN
3933
Created by admin on Sat Dec 16 17:00:01 UTC 2023 , Edited by admin on Sat Dec 16 17:00:01 UTC 2023
PRIMARY
NCI_THESAURUS
C166672
Created by admin on Sat Dec 16 17:00:01 UTC 2023 , Edited by admin on Sat Dec 16 17:00:01 UTC 2023
PRIMARY
MERCK INDEX
m8920
Created by admin on Sat Dec 16 17:00:01 UTC 2023 , Edited by admin on Sat Dec 16 17:00:01 UTC 2023
PRIMARY Merck Index
WIKIPEDIA
PLEUROMUTILIN
Created by admin on Sat Dec 16 17:00:01 UTC 2023 , Edited by admin on Sat Dec 16 17:00:01 UTC 2023
PRIMARY
ECHA (EC/EINECS)
204-747-5
Created by admin on Sat Dec 16 17:00:01 UTC 2023 , Edited by admin on Sat Dec 16 17:00:01 UTC 2023
PRIMARY
NSC
121145
Created by admin on Sat Dec 16 17:00:01 UTC 2023 , Edited by admin on Sat Dec 16 17:00:01 UTC 2023
PRIMARY
PUBCHEM
9886081
Created by admin on Sat Dec 16 17:00:01 UTC 2023 , Edited by admin on Sat Dec 16 17:00:01 UTC 2023
PRIMARY
FDA UNII
3DE4A80MZ1
Created by admin on Sat Dec 16 17:00:01 UTC 2023 , Edited by admin on Sat Dec 16 17:00:01 UTC 2023
PRIMARY
EVMPD
SUB09958MIG
Created by admin on Sat Dec 16 17:00:01 UTC 2023 , Edited by admin on Sat Dec 16 17:00:01 UTC 2023
PRIMARY
EPA CompTox
DTXSID9048720
Created by admin on Sat Dec 16 17:00:01 UTC 2023 , Edited by admin on Sat Dec 16 17:00:01 UTC 2023
PRIMARY
ChEMBL
CHEMBL2105226
Created by admin on Sat Dec 16 17:00:01 UTC 2023 , Edited by admin on Sat Dec 16 17:00:01 UTC 2023
PRIMARY
Related Record Type Details
Structure of VALNEMULIN HYDROCHLORIDE
PARENT -> IMPURITY
Structure of TIAMULIN FUMARATE
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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