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

Details

Stereochemistry ABSOLUTE
Molecular Formula C29H40N4O7
Molecular Weight 556.6516
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of OMADACYCLINE

SMILES

CC(C)(C)CNCc1cc(c2C[C@@]3([H])C[C@@]4([H])[C@@]([H])(C(=C(C(=O)[C@]4(C(=C3C(=O)c2c1O)O)O)C(=N)O)O)N(C)C)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
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

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
1.96 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
NUZYRA

Approved Use

NUZYRA is a tetracycline class antibacterial indicated for the treatment of adult patients with the following infections caused by susceptible microorganisms: - Community-acquired bacterial pneumonia (CABP) - Acute bacterial skin and skin structure infections (ABSSSI)

Launch Date

1.53835196E12
Curative
NUZYRA

Approved Use

NUZYRA is a tetracycline class antibacterial indicated for the treatment of adult patients with the following infections caused by susceptible microorganisms: - Community-acquired bacterial pneumonia (CABP) - Acute bacterial skin and skin structure infections (ABSSSI)

Launch Date

1.53835196E12
Curative
Unknown

Approved Use

Unknown
Curative
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
952 ng/mL
300 mg 1 times / day steady-state, oral
dose: 300 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
OMADACYCLINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
2120 ng/mL
100 mg 1 times / day steady-state, intravenous
dose: 100 mg
route of administration: Intravenous
experiment type: STEADY-STATE
co-administered:
OMADACYCLINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
1077 ng/mL
450 mg 1 times / day steady-state, oral
dose: 450 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
OMADACYCLINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
874 ng/mL
450 mg single, oral
dose: 450 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
OMADACYCLINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
1507 ng/mL
100 mg single, intravenous
dose: 100 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
OMADACYCLINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
548 ng/mL
300 mg single, oral
dose: 300 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
OMADACYCLINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
640.84 ng/mL
300 mg single, oral
dose: 300 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
OMADACYCLINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
271.1 ng/mL
300 mg single, oral
dose: 300 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
OMADACYCLINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: HIGH-FAT
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
11156 ng × h/mL
300 mg 1 times / day steady-state, oral
dose: 300 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
OMADACYCLINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
12140 ng × h/mL
100 mg 1 times / day steady-state, intravenous
dose: 100 mg
route of administration: Intravenous
experiment type: STEADY-STATE
co-administered:
OMADACYCLINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
13367 ng × h/mL
450 mg 1 times / day steady-state, oral
dose: 450 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
OMADACYCLINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
8977 ng × h/mL
450 mg single, oral
dose: 450 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
OMADACYCLINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
93.58 ng × h/mL
100 mg single, intravenous
dose: 100 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
OMADACYCLINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
9399 ng × h/mL
300 mg single, oral
dose: 300 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
OMADACYCLINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
10158.6 ng × h/mL
300 mg single, oral
dose: 300 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
OMADACYCLINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
4028.85 ng × h/mL
300 mg single, oral
dose: 300 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
OMADACYCLINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: HIGH-FAT
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
15.5 h
300 mg 1 times / day steady-state, oral
dose: 300 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
OMADACYCLINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
16 h
100 mg 1 times / day steady-state, intravenous
dose: 100 mg
route of administration: Intravenous
experiment type: STEADY-STATE
co-administered:
OMADACYCLINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
19.83 h
450 mg 1 times / day steady-state, oral
dose: 450 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
OMADACYCLINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
13.45 h
450 mg single, oral
dose: 450 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
OMADACYCLINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
16.2 h
100 mg single, intravenous
dose: 100 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
OMADACYCLINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
14.96 h
300 mg single, oral
dose: 300 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
OMADACYCLINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
13.81 h
300 mg single, oral
dose: 300 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
OMADACYCLINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
13.5 h
300 mg single, oral
dose: 300 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
OMADACYCLINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: HIGH-FAT
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
80%
300 mg 1 times / day steady-state, oral
dose: 300 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
OMADACYCLINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
80%
100 mg 1 times / day steady-state, intravenous
dose: 100 mg
route of administration: Intravenous
experiment type: STEADY-STATE
co-administered:
OMADACYCLINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
80%
450 mg 1 times / day steady-state, oral
dose: 450 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
OMADACYCLINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
80%
450 mg single, oral
dose: 450 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
OMADACYCLINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
80%
100 mg single, intravenous
dose: 100 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
OMADACYCLINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
80%
300 mg single, oral
dose: 300 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
OMADACYCLINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
600 mg 1 times / day steady, oral
Highest studied dose
Dose: 600 mg, 1 times / day
Route: oral
Route: steady
Dose: 600 mg, 1 times / day
Sources:
healthy, mean age 35.6 years
n = 24
Health Status: healthy
Age Group: mean age 35.6 years
Sex: M+F
Population Size: 24
Sources:
Disc. AE: Lipase increased...
Other AEs: Nausea, Vomiting...
AEs leading to
discontinuation/dose reduction:
Lipase increased (grade 1-3, 4.2%)
Other AEs:
Nausea (grade 1-2, 16.7%)
Vomiting (grade 1-2, 4.2%)
Diarrhea (grade 1-2, 8.3%)
Dizziness (grade 1-2, 4.2%)
ALT increased (grade 1-2, 4.2%)
Sources:
600 mg 1 times / day steady, oral
MTD|Highest studied dose
healthy, mean age 35.6 years
n = 24
DLT: Lipase increased...
Other AEs: Nausea, Vomiting...
Dose limiting toxicities:
Lipase increased (4.2%)
Other AEs:
Nausea (grade 1-2, 16.7%)
Vomiting (grade 1-2, 4.2%)
Diarrhea (grade 1-2, 8.3%)
Dizziness (grade 1-2, 4.2%)
ALT increased (grade 1-2, 4.2%)
Sources:
300 mg 1 times / day steady, oral
Studied dose
healthy, mean age 35.6 years
n = 26
Disc. AE: Vomiting, Nausea...
Other AEs: Dizziness, Vomiting...
AEs leading to
discontinuation/dose reduction:
Vomiting (3.8%)
Nausea (3.8%)
Other AEs:
Dizziness (grade 1-2, 7.7%)
Vomiting (grade 1-2, 7.7%)
Nausea (grade 1-2, 7.7%)
Sources:
100 mg 1 times / day steady, intravenous
Studied dose
healthy, mean age 38 years
n = 42
Other AEs: Headache, Nausea...
600 mg 1 times / day single, intravenous
Highest studied dose
healthy, young
n = 2
DLT: ALT increased...
400 mg 1 times / day single, intravenous
MTD
Dose: 400 mg, 1 times / day
Route: intravenous
Route: single
Dose: 400 mg, 1 times / day
Sources:
healthy, young
Other AEs: Elevated liver enzymes...
AEs

AEs

AESignificanceDosePopulation
Nausea grade 1-2, 16.7%
600 mg 1 times / day steady, oral
Highest studied dose
Dose: 600 mg, 1 times / day
Route: oral
Route: steady
Dose: 600 mg, 1 times / day
Sources:
healthy, mean age 35.6 years
n = 24
Health Status: healthy
Age Group: mean age 35.6 years
Sex: M+F
Population Size: 24
Sources:
ALT increased grade 1-2, 4.2%
600 mg 1 times / day steady, oral
Highest studied dose
Dose: 600 mg, 1 times / day
Route: oral
Route: steady
Dose: 600 mg, 1 times / day
Sources:
healthy, mean age 35.6 years
n = 24
Health Status: healthy
Age Group: mean age 35.6 years
Sex: M+F
Population Size: 24
Sources:
Dizziness grade 1-2, 4.2%
600 mg 1 times / day steady, oral
Highest studied dose
Dose: 600 mg, 1 times / day
Route: oral
Route: steady
Dose: 600 mg, 1 times / day
Sources:
healthy, mean age 35.6 years
n = 24
Health Status: healthy
Age Group: mean age 35.6 years
Sex: M+F
Population Size: 24
Sources:
Vomiting grade 1-2, 4.2%
600 mg 1 times / day steady, oral
Highest studied dose
Dose: 600 mg, 1 times / day
Route: oral
Route: steady
Dose: 600 mg, 1 times / day
Sources:
healthy, mean age 35.6 years
n = 24
Health Status: healthy
Age Group: mean age 35.6 years
Sex: M+F
Population Size: 24
Sources:
Diarrhea grade 1-2, 8.3%
600 mg 1 times / day steady, oral
Highest studied dose
Dose: 600 mg, 1 times / day
Route: oral
Route: steady
Dose: 600 mg, 1 times / day
Sources:
healthy, mean age 35.6 years
n = 24
Health Status: healthy
Age Group: mean age 35.6 years
Sex: M+F
Population Size: 24
Sources:
Lipase increased grade 1-3, 4.2%
Disc. AE
600 mg 1 times / day steady, oral
Highest studied dose
Dose: 600 mg, 1 times / day
Route: oral
Route: steady
Dose: 600 mg, 1 times / day
Sources:
healthy, mean age 35.6 years
n = 24
Health Status: healthy
Age Group: mean age 35.6 years
Sex: M+F
Population Size: 24
Sources:
Lipase increased 4.2%
DLT
600 mg 1 times / day steady, oral
MTD|Highest studied dose
healthy, mean age 35.6 years
n = 24
Nausea grade 1-2, 16.7%
600 mg 1 times / day steady, oral
MTD|Highest studied dose
healthy, mean age 35.6 years
n = 24
ALT increased grade 1-2, 4.2%
600 mg 1 times / day steady, oral
MTD|Highest studied dose
healthy, mean age 35.6 years
n = 24
Dizziness grade 1-2, 4.2%
600 mg 1 times / day steady, oral
MTD|Highest studied dose
healthy, mean age 35.6 years
n = 24
Vomiting grade 1-2, 4.2%
600 mg 1 times / day steady, oral
MTD|Highest studied dose
healthy, mean age 35.6 years
n = 24
Diarrhea grade 1-2, 8.3%
600 mg 1 times / day steady, oral
MTD|Highest studied dose
healthy, mean age 35.6 years
n = 24
Nausea 3.8%
Disc. AE
300 mg 1 times / day steady, oral
Studied dose
healthy, mean age 35.6 years
n = 26
Vomiting 3.8%
Disc. AE
300 mg 1 times / day steady, oral
Studied dose
healthy, mean age 35.6 years
n = 26
Dizziness grade 1-2, 7.7%
300 mg 1 times / day steady, oral
Studied dose
healthy, mean age 35.6 years
n = 26
Nausea grade 1-2, 7.7%
300 mg 1 times / day steady, oral
Studied dose
healthy, mean age 35.6 years
n = 26
Vomiting grade 1-2, 7.7%
300 mg 1 times / day steady, oral
Studied dose
healthy, mean age 35.6 years
n = 26
Headache grade 1-2, 11.9%
100 mg 1 times / day steady, intravenous
Studied dose
healthy, mean age 38 years
n = 42
Nausea grade 1-2, 2.4%
100 mg 1 times / day steady, intravenous
Studied dose
healthy, mean age 38 years
n = 42
ALT increased grade 2
DLT
600 mg 1 times / day single, intravenous
Highest studied dose
healthy, young
n = 2
Elevated liver enzymes grade 2
400 mg 1 times / day single, intravenous
MTD
Dose: 400 mg, 1 times / day
Route: intravenous
Route: single
Dose: 400 mg, 1 times / day
Sources:
healthy, young
Overview

Overview

Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
weak
unlikely
Comment: shown to be a weak inducer of CYP2C19 at a concentration 5 -fold higher than Cmax
Page: 90.0
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
likely
weak (co-administration study)
Comment: Verapamil dosing increased the omadacycline AUC by approximately 18% and the Cmax by 14%
Page: 90.0
no
no
no
no
no
no
no
no
no
no
Tox targets
PubMed

PubMed

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

Patents

Sample Use Guides

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: Other
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.
Name Type Language
OMADACYCLINE
INN   USAN   WHO-DD  
USAN   INN  
Official Name English
OMADACYCLINE [MI]
Common 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
Classification Tree Code System Code
NCI_THESAURUS C258
Created by admin on Sat Jun 26 10:33:57 UTC 2021 , Edited by admin on Sat Jun 26 10:33:57 UTC 2021
Code System Code Type Description
PUBCHEM
54697325
Created by admin on Sat Jun 26 10:33:57 UTC 2021 , Edited by admin on Sat Jun 26 10:33:57 UTC 2021
PRIMARY
EVMPD
SUB181298
Created by admin on Sat Jun 26 10:33:57 UTC 2021 , Edited by admin on Sat Jun 26 10:33:57 UTC 2021
PRIMARY
CAS
389139-89-3
Created by admin on Sat Jun 26 10:33:57 UTC 2021 , Edited by admin on Sat Jun 26 10:33:57 UTC 2021
PRIMARY
ChEMBL
CHEMBL1689772
Created by admin on Sat Jun 26 10:33:57 UTC 2021 , Edited by admin on Sat Jun 26 10:33:57 UTC 2021
PRIMARY
LACTMED
Omadacycline
Created by admin on Sat Jun 26 10:33:57 UTC 2021 , Edited by admin on Sat Jun 26 10:33:57 UTC 2021
PRIMARY
DRUG CENTRAL
5299
Created by admin on Sat Jun 26 10:33:57 UTC 2021 , Edited by admin on Sat Jun 26 10:33:57 UTC 2021
PRIMARY
FDA UNII
090IP5RV8F
Created by admin on Sat Jun 26 10:33:57 UTC 2021 , Edited by admin on Sat Jun 26 10:33:57 UTC 2021
PRIMARY
INN
9186
Created by admin on Sat Jun 26 10:33:57 UTC 2021 , Edited by admin on Sat Jun 26 10:33:57 UTC 2021
PRIMARY
RXCUI
2059269
Created by admin on Sat Jun 26 10:33:57 UTC 2021 , Edited by admin on Sat Jun 26 10:33:57 UTC 2021
PRIMARY
NCI_THESAURUS
C90688
Created by admin on Sat Jun 26 10:33:57 UTC 2021 , Edited by admin on Sat Jun 26 10:33:57 UTC 2021
PRIMARY
MERCK INDEX
M12098
Created by admin on Sat Jun 26 10:33:57 UTC 2021 , Edited by admin on Sat Jun 26 10:33:57 UTC 2021
PRIMARY
DRUG BANK
DB12455
Created by admin on Sat Jun 26 10:33:57 UTC 2021 , Edited by admin on Sat Jun 26 10:33:57 UTC 2021
PRIMARY