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Details

Stereochemistry ABSOLUTE
Molecular Formula C29H40N4O7
Molecular Weight 556.6505
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of OMADACYCLINE

SMILES

CN(C)[C@H]1[C@@H]2C[C@@H]3CC4=C(C=C(CNCC(C)(C)C)C(O)=C4C(=O)C3=C(O)[C@]2(O)C(=O)C(C(N)=O)=C1O)N(C)C

InChI

InChIKey=JEECQCWWSTZDCK-IQZGDKDPSA-N
InChI=1S/C29H40N4O7/c1-28(2,3)12-31-11-14-10-17(32(4)5)15-8-13-9-16-21(33(6)7)24(36)20(27(30)39)26(38)29(16,40)25(37)18(13)23(35)19(15)22(14)34/h10,13,16,21,31,34,36-37,40H,8-9,11-12H2,1-7H3,(H2,30,39)/t13-,16-,21-,29-/m0/s1

HIDE SMILES / InChI

Molecular Formula C29H40N4O7
Molecular Weight 556.6505
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Omadacycline is a tetracyclin-derivative antibiotic, originated in Tufts University, and later co-developed by Merck and Paratek Pharmaceuticals. The drug was approved for treatment of community-acquired pneumonia, and for treatment of acute bacterial skin and skin structure infections. Omadacycline tosylate is available as tablets and in injectable form.

CNS Activity

Originator

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
1.96 µM [IC50]
Conditions
PubMed

PubMed

TitleDatePubMed
Mechanism of action of the novel aminomethylcycline antibiotic omadacycline.
2014
Omadacycline for Community-Acquired Bacterial Pneumonia.
2019 Feb 7
Omadacycline for Acute Bacterial Skin and Skin-Structure Infections.
2019 Feb 7
Patents

Patents

Sample Use Guides

In Vivo Use Guide
For the treatment of acute bacterial skin and skin structure infections (ABSSSI), omadacycline could be administered intravenously or orally. Loading dose for intravenous administration is 200 mg by intravenous infusion over 60 minutes or 100 mg by intravenous infusion over 30 minutes twice on day 1. Loading dose for oral administration is 450 mg orally once daily. Maintenance dose is 100 mg by intravenous infusion over 30 minutes once daily or 300 mg orally once daily. For treatment of community-acquired pneumonia, the drug is administered intravenously according to the same schedule as ABSSSI.
Route of Administration: oral; intravenous
In Vitro Use Guide
Susceptibility testing was performed according to the M7-A5 CLSI-recommended microdilution method. Cation-adjusted Mueller-Hinton broth (MHB) was used. To prepare the inoculum, organisms were grown to a 0.5 McFarland standard, which was measured with a Microscan turbidity meter. Microplates were incubated at 35°C for 18 to 24 h as specified by CLSI M07-08. Omadacycline is active against strains expressing either efflux or ribosomal mechanisms of tetracycline resistance. S. pneumoniae PBS382 MIC is below 0.06 ug/ml.
Substance Class Chemical
Created
by admin
on Tue Mar 06 17:04:33 UTC 2018
Edited
by admin
on Tue Mar 06 17:04:33 UTC 2018
Record UNII
090IP5RV8F
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
OMADACYCLINE
INN   USAN   WHO-DD  
USAN   INN  
Official Name English
OMADACYCLINE [INN]
Common Name English
OMADACYCLINE [WHO-DD]
Common Name English
2-NAPHTHACENECARBOXAMIDE, 4,7-BIS(DIMETHYLAMINO)-9-(((2,2-DIMETHYLPROPYL)AMINO)METHYL)-1,4,4A,5,5A,6,11,12A-OCTAHYDRO-3,10,12,12A-TETRAHYDROXY-1,11-DIOXO-, (4S,4AS,5AR,12AS)-
Common Name English
AMADACYCLINE
Common Name English
(4S,4AS,5AR,12AS)-4,7-BIS(DIMETHYLAMINO)-9-(((2,2-DIMETHYLPROPYL)AMINO)METHYL)-3,10,12,12A- TETRAHYDROXY-1,11-DIOXO-1,4,4A,5,5A,6,11,12A-OCTAHYDROTETRACENE-2-CARBOXAMIDE
Common Name English
BAY 73-6944
Code English
OMADACYCLINE [USAN]
Common Name English
Code System Code Type Description
PUBCHEM
54697325
Created by admin on Tue Mar 06 17:04:33 UTC 2018 , Edited by admin on Tue Mar 06 17:04:33 UTC 2018
PRIMARY SWITZERF
EVMPD
SUB181298
Created by admin on Tue Mar 06 17:04:33 UTC 2018 , Edited by admin on Tue Mar 06 17:04:33 UTC 2018
PRIMARY
CAS
389139-89-3
Created by admin on Tue Mar 06 17:04:33 UTC 2018 , Edited by admin on Tue Mar 06 17:04:33 UTC 2018
PRIMARY
ChEMBL
CHEMBL1689772
Created by admin on Tue Mar 06 17:04:33 UTC 2018 , Edited by admin on Tue Mar 06 17:04:33 UTC 2018
PRIMARY
INN
9186
Created by admin on Tue Mar 06 17:04:33 UTC 2018 , Edited by admin on Tue Mar 06 17:04:33 UTC 2018
PRIMARY
NCI_THESAURUS
C90688
Created by admin on Tue Mar 06 17:04:33 UTC 2018 , Edited by admin on Tue Mar 06 17:04:33 UTC 2018
PRIMARY
Related Record Type Details
ACTIVE MOIETY