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Details

Stereochemistry ABSOLUTE
Molecular Formula C43H65FN6O10
Molecular Weight 845.0088
Optical Activity UNSPECIFIED
Defined Stereocenters 13 / 13
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SOLITHROMYCIN

SMILES

[H][C@@]12[C@@H](C)C(=O)[C@H](C)C[C@@](C)(OC)[C@H](O[C@@H]3O[C@H](C)C[C@@H]([C@H]3O)N(C)C)[C@@H](C)C(=O)[C@](C)(F)C(=O)O[C@H](CC)[C@@]1(C)OC(=O)N2CCCCN4C=C(N=N4)C5=CC=CC(N)=C5

InChI

InChIKey=IXXFZUPTQVDPPK-ZAWHAJPISA-N
InChI=1S/C43H65FN6O10/c1-12-32-43(8)35(50(40(55)60-43)19-14-13-18-49-23-30(46-47-49)28-16-15-17-29(45)21-28)26(4)33(51)24(2)22-41(6,56-11)37(27(5)36(53)42(7,44)39(54)58-32)59-38-34(52)31(48(9)10)20-25(3)57-38/h15-17,21,23-27,31-32,34-35,37-38,52H,12-14,18-20,22,45H2,1-11H3/t24-,25-,26+,27+,31+,32-,34-,35-,37-,38+,41-,42+,43-/m1/s1

HIDE SMILES / InChI

Molecular Formula C43H65FN6O10
Molecular Weight 845.0088
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 13 / 13
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: Description was created based on several sources, including https://www.drugs.com/history/solithera.html https://www.ncbi.nlm.nih.gov/pubmed/23318809

Solithromycin is a highly potent next-generation macrolide, the first fluoroketolide, which has potent activity against most macrolide-resistant strains. In vitro and in vivo studies have shown potent activity against S. pneumoniae as well as an extended spectrum of activity against CA-MRSA, enterococci, Mycobacterium avium and in animal models of malaria. It is also active against atypical bacteria, such as Legionella, Chlamydophila, Chlamydia, Mycoplasmaand Ureaplasma and against gonococci and other organisms that cause genitourinary tract infections. It is 8-16 times more potent than azithromycin and is active against azithromycin-resistant strains. Its activity against resistant strains is driven by its ability to bind to three sites on the bacterial ribosome, compared to one or two for current macrolides. It binds to the large 50S subunit of the ribosome and inhibits protein biosynthesis. The binding to three ribosomal sites is expected to limit resistance development. On July 2016 Cempra Announces FDA Acceptance of IV and oral formulations of Solithera (solithromycin) New Drug Applications for in the treatment of community-acquired bacterial pneumonia.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Unknown

Approved Use

Unknown
Curative
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
In Vitro Activity of Solithromycin against Bordetella pertussis, an Emerging Respiratory Pathogen.
2016 Dec
Patents

Patents

Sample Use Guides

A single oral dose of 1200 mg solithromycin
Route of Administration: Oral
For 50S subunit formation in S. pneumoniae, the IC50 for assembly inhibition was 15 ng/ml. Solithromycin was found to interfere with 50S ribosomal subunit formation in both methicillin-sensitive and methicillin-resistant strains of Staphylococcus aureus, with IC50s of 65 and 93 ng/ml, respectively
Substance Class Chemical
Created
by admin
on Fri Dec 15 19:12:45 UTC 2023
Edited
by admin
on Fri Dec 15 19:12:45 UTC 2023
Record UNII
9U1ETH79CK
Record Status Validated (UNII)
Record Version
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Name Type Language
SOLITHROMYCIN
INN   USAN   WHO-DD  
USAN   INN  
Official Name English
solithromycin [INN]
Common Name English
SOLITHROMYCIN [USAN]
Common Name English
OP1068
Code English
SOLITHROMYCIN [JAN]
Common Name English
(3AR,4R,7S,9R,10R,11R,13R,15R,15AR)-1-(4-(4-(3-AMINOPHENYL)-1H-1,2,3-TRIAZOL-1-YL)BUTYL)-4-ETHYL-7-FLUORO-11-METHOXY-3A,7,9,11,13,15-HEXAMETHYL-10-((TRIDEOXY-(DIMETHYLAMINO)-
Common Name English
OP-1068
Code English
Solithromycin [WHO-DD]
Common Name English
CEM-101
Code English
CEM101
Code English
Classification Tree Code System Code
NCI_THESAURUS C261
Created by admin on Fri Dec 15 19:12:45 UTC 2023 , Edited by admin on Fri Dec 15 19:12:45 UTC 2023
WHO-ATC J01FA16
Created by admin on Fri Dec 15 19:12:45 UTC 2023 , Edited by admin on Fri Dec 15 19:12:45 UTC 2023
Code System Code Type Description
CAS
760981-83-7
Created by admin on Fri Dec 15 19:12:45 UTC 2023 , Edited by admin on Fri Dec 15 19:12:45 UTC 2023
PRIMARY
USAN
WW-65
Created by admin on Fri Dec 15 19:12:45 UTC 2023 , Edited by admin on Fri Dec 15 19:12:45 UTC 2023
PRIMARY
EPA CompTox
DTXSID501028410
Created by admin on Fri Dec 15 19:12:45 UTC 2023 , Edited by admin on Fri Dec 15 19:12:45 UTC 2023
PRIMARY
DRUG BANK
DB09308
Created by admin on Fri Dec 15 19:12:45 UTC 2023 , Edited by admin on Fri Dec 15 19:12:45 UTC 2023
PRIMARY
SMS_ID
100000169135
Created by admin on Fri Dec 15 19:12:45 UTC 2023 , Edited by admin on Fri Dec 15 19:12:45 UTC 2023
PRIMARY
INN
9358
Created by admin on Fri Dec 15 19:12:45 UTC 2023 , Edited by admin on Fri Dec 15 19:12:45 UTC 2023
PRIMARY
ChEMBL
CHEMBL1240704
Created by admin on Fri Dec 15 19:12:45 UTC 2023 , Edited by admin on Fri Dec 15 19:12:45 UTC 2023
PRIMARY
WIKIPEDIA
SOLITHROMYCIN
Created by admin on Fri Dec 15 19:12:45 UTC 2023 , Edited by admin on Fri Dec 15 19:12:45 UTC 2023
PRIMARY
FDA UNII
9U1ETH79CK
Created by admin on Fri Dec 15 19:12:45 UTC 2023 , Edited by admin on Fri Dec 15 19:12:45 UTC 2023
PRIMARY
NCI_THESAURUS
C152386
Created by admin on Fri Dec 15 19:12:45 UTC 2023 , Edited by admin on Fri Dec 15 19:12:45 UTC 2023
PRIMARY
PUBCHEM
25242512
Created by admin on Fri Dec 15 19:12:45 UTC 2023 , Edited by admin on Fri Dec 15 19:12:45 UTC 2023
PRIMARY
EVMPD
SUB182801
Created by admin on Fri Dec 15 19:12:45 UTC 2023 , Edited by admin on Fri Dec 15 19:12:45 UTC 2023
PRIMARY
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