U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C59H88N2O20
Molecular Weight 1145.3314
Optical Activity UNSPECIFIED
Defined Stereocenters 21 / 21
E/Z Centers 7
Charge 0

SHOW SMILES / InChI
Structure of EFROTOMYCIN

SMILES

[H][C@]1(O[C@H](\C=C\C=C\C=C(/C)C(=O)C2=C(O)C=CN(C)C2=O)[C@H](O)[C@@H]1O)[C@H](C)[C@H](OC)C(\C)=C\C=C\CNC(=O)[C@@H](CC)[C@@]3(O)O[C@@H](\C=C\C=C/C)C(C)(C)[C@@H](O[C@]4([H])O[C@H](C)[C@@H](O[C@]5([H])O[C@@H](C)[C@H](OC)[C@@H](O)[C@H]5OC)[C@@H](OC)[C@H]4O)[C@H]3O

InChI

InChIKey=ASOJLQIBBYOFDE-SBHXXGSWSA-N
InChI=1S/C59H88N2O20/c1-15-17-19-27-39-58(8,9)53(80-56-45(67)50(74-13)49(35(7)76-56)79-57-51(75-14)44(66)48(73-12)34(6)77-57)52(68)59(71,81-39)36(16-2)54(69)60-29-23-22-25-32(4)46(72-11)33(5)47-43(65)42(64)38(78-47)26-21-18-20-24-31(3)41(63)40-37(62)28-30-61(10)55(40)70/h15,17-28,30,33-36,38-39,42-53,56-57,62,64-68,71H,16,29H2,1-14H3,(H,60,69)/b17-15-,20-18+,23-22+,26-21+,27-19+,31-24+,32-25+/t33-,34+,35-,36-,38-,39+,42+,43+,44-,45-,46-,47+,48+,49-,50+,51-,52-,53+,56+,57+,59-/m1/s1

HIDE SMILES / InChI
Efrotomycin (ET) is an antibiotic obtained by the incubation of Nocardia lacamduranns, and composed of 4 components: Efrotomycin A1, Efrotomycin A2, Efrotomycin B1, and Efrotomycin B2. Although its antibacterial spectrum is narrow, ET has an antibacterial effect on part of the Grampositive bacteria and on treponema, and has a growth promoting effect on pigs etc. ET is a pure-grade antibiotic that was designated as a feed additive. Under the brand name Producil Efrotomycin was indicated for increased rate of weight gain when incorporated into complete swine feeds at 3.6 to 14.5 g/ton. This antibiotic is a potent inhibitor of bacterial protein synthesis by interfering with peptide transfer reactions associated with the elongation factor Tu.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P0CE47
Gene ID: 947838.0
Gene Symbol: tufA
Target Organism: Escherichia coli (strain K12)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Producil

Approved Use

For increased rate of weight gain when incorporated into complete swine feeds at 3.6 to 14.5 g/ton. Feed Efficiency: For improved feed efficiency when incorporated into complete swine feeds at 3.6 g/ton.

Launch Date

1992
PubMed

PubMed

TitleDatePubMed
Screening for new compounds with antiherpes activity.
1984 Oct
Patents

Sample Use Guides

Pigs: Dosage: Form: A free-flowing, non-dusty, granular premix containing 32 grams of efrotomycin activity per kilogram intended for incorporation in swine rations. Route of administration: Orally as an additive to swine feeds. Recommended dosage: The effective range for efrotomycin use in swine is 4 to 16 ppm (3.6 to 14.5 g/ton) inclusive for increases in average daily gain and 4 ppm (3.6 g/ton) for improvements in feed efficiency. Blend Producil into complete swine feeds at 4 oz - 16 oz per ton to supply 3.6 g - 14.5 g efrotomycin per ton of feed.
Route of Administration: Oral
In Vitro Use Guide
Efrotomycin (MIC50 = 0.125, MIC90 = 0.25 ug/ml) was highly active against C. difficile.
Name Type Language
EFROTOMYCIN
GREEN BOOK   INN   MI   USAN  
INN   USAN  
Official Name English
EFROTOMYCIN [MI]
Common Name English
PRODUCIL
Brand Name English
MOCIMYCIN, 31-O-(6-DEOXY-4-O-(6-DEOXY-2,4-DI-O-METHYL-.ALPHA.-L-MANNOPYRANOSYL)-3-O-METHYL-.BETA.-D-ALLOPYRANOSYL)-1-METHYL-
Common Name English
EFROTOMYCIN [GREEN BOOK]
Common Name English
efrotomycin [INN]
Common Name English
MK-621
Code English
EFROTOMYCIN [USAN]
Common Name English
Classification Tree Code System Code
CFR 21 CFR 558.235
Created by admin on Fri Dec 15 16:14:35 GMT 2023 , Edited by admin on Fri Dec 15 16:14:35 GMT 2023
NCI_THESAURUS C258
Created by admin on Fri Dec 15 16:14:35 GMT 2023 , Edited by admin on Fri Dec 15 16:14:35 GMT 2023
Code System Code Type Description
NCI_THESAURUS
C83686
Created by admin on Fri Dec 15 16:14:35 GMT 2023 , Edited by admin on Fri Dec 15 16:14:35 GMT 2023
PRIMARY
CAS
56592-32-6
Created by admin on Fri Dec 15 16:14:35 GMT 2023 , Edited by admin on Fri Dec 15 16:14:35 GMT 2023
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USAN
W-69
Created by admin on Fri Dec 15 16:14:35 GMT 2023 , Edited by admin on Fri Dec 15 16:14:35 GMT 2023
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PUBCHEM
135564847
Created by admin on Fri Dec 15 16:14:35 GMT 2023 , Edited by admin on Fri Dec 15 16:14:35 GMT 2023
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ChEMBL
CHEMBL2106443
Created by admin on Fri Dec 15 16:14:35 GMT 2023 , Edited by admin on Fri Dec 15 16:14:35 GMT 2023
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EVMPD
SUB06472MIG
Created by admin on Fri Dec 15 16:14:35 GMT 2023 , Edited by admin on Fri Dec 15 16:14:35 GMT 2023
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FDA UNII
5BPJ82Q45X
Created by admin on Fri Dec 15 16:14:35 GMT 2023 , Edited by admin on Fri Dec 15 16:14:35 GMT 2023
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MESH
C012954
Created by admin on Fri Dec 15 16:14:35 GMT 2023 , Edited by admin on Fri Dec 15 16:14:35 GMT 2023
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DRUG BANK
DB11401
Created by admin on Fri Dec 15 16:14:35 GMT 2023 , Edited by admin on Fri Dec 15 16:14:35 GMT 2023
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MERCK INDEX
m4842
Created by admin on Fri Dec 15 16:14:35 GMT 2023 , Edited by admin on Fri Dec 15 16:14:35 GMT 2023
PRIMARY Merck Index
INN
5687
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EPA CompTox
DTXSID501318259
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SMS_ID
100000080537
Created by admin on Fri Dec 15 16:14:35 GMT 2023 , Edited by admin on Fri Dec 15 16:14:35 GMT 2023
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