OMADACYCLINE

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

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

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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

Primary Target	Pharmacology	Condition	Potency
70S ribosome 16	Inhibitor 8,504		1.96 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Acute bacterial skin and skin structure infections 2	Curative	Approved 8,583	NUZYRA
Community-acquired bacterial pneumonia 11	Curative	Approved 8,583	NUZYRA
Cystitis 27	Curative	Phase II 1,147	Unknown
Acute Pyelonephritis 2	Curative	Phase II 1,147	Unknown

C_max

Value	Dose	Analyte	Population
1507 ng/mL	100 mg single, intravenous	OMADACYCLINE plasma	Homo sapiens
2120 ng/mL	100 mg 1 times / day steady-state, intravenous	OMADACYCLINE plasma	Homo sapiens
548 ng/mL	300 mg single, oral	OMADACYCLINE plasma	Homo sapiens
952 ng/mL	300 mg 1 times / day steady-state, oral	OMADACYCLINE plasma	Homo sapiens
874 ng/mL	450 mg single, oral	OMADACYCLINE plasma	Homo sapiens
1077 ng/mL	450 mg 1 times / day steady-state, oral	OMADACYCLINE plasma	Homo sapiens
640.84 ng/mL	300 mg single, oral	OMADACYCLINE plasma	Homo sapiens
271.1 ng/mL	300 mg single, oral	OMADACYCLINE plasma	Homo sapiens

AUC

Value	Dose	Analyte	Population
93.58 ng × h/mL	100 mg single, intravenous	OMADACYCLINE plasma	Homo sapiens
12140 ng × h/mL	100 mg 1 times / day steady-state, intravenous	OMADACYCLINE plasma	Homo sapiens
9399 ng × h/mL	300 mg single, oral	OMADACYCLINE plasma	Homo sapiens
11156 ng × h/mL	300 mg 1 times / day steady-state, oral	OMADACYCLINE plasma	Homo sapiens
8977 ng × h/mL	450 mg single, oral	OMADACYCLINE plasma	Homo sapiens
13367 ng × h/mL	450 mg 1 times / day steady-state, oral	OMADACYCLINE plasma	Homo sapiens
10158.6 ng × h/mL	300 mg single, oral	OMADACYCLINE plasma	Homo sapiens
4028.85 ng × h/mL	300 mg single, oral	OMADACYCLINE plasma	Homo sapiens

T_1/2

Value	Dose	Analyte	Population
16.2 h	100 mg single, intravenous	OMADACYCLINE plasma	Homo sapiens
16 h	100 mg 1 times / day steady-state, intravenous	OMADACYCLINE plasma	Homo sapiens
14.96 h	300 mg single, oral	OMADACYCLINE plasma	Homo sapiens
15.5 h	300 mg 1 times / day steady-state, oral	OMADACYCLINE plasma	Homo sapiens
13.45 h	450 mg single, oral	OMADACYCLINE plasma	Homo sapiens
19.83 h	450 mg 1 times / day steady-state, oral	OMADACYCLINE plasma	Homo sapiens
13.81 h	300 mg single, oral	OMADACYCLINE plasma	Homo sapiens
13.5 h	300 mg single, oral	OMADACYCLINE plasma	Homo sapiens

F_unbound

Value	Dose	Analyte	Population
80%	100 mg single, intravenous	OMADACYCLINE plasma	Homo sapiens
80%	100 mg 1 times / day steady-state, intravenous	OMADACYCLINE plasma	Homo sapiens
80%	300 mg single, oral	OMADACYCLINE plasma	Homo sapiens
80%	300 mg 1 times / day steady-state, oral	OMADACYCLINE plasma	Homo sapiens
80%	450 mg single, oral	OMADACYCLINE plasma	Homo sapiens
80%	450 mg 1 times / day steady-state, oral	OMADACYCLINE plasma	Homo sapiens

Doses

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Dose	Population	Adverse events
600 mg 1 times / day steady, oral Highest studied dose	healthy, mean age 35.6 years	Disc. AE: Lipase increased... Other AEs: Nausea, Vomiting...
600 mg 1 times / day steady, oral MTD\|Highest studied dose	healthy, mean age 35.6 years	DLT: Lipase increased... Other AEs: Nausea, Vomiting...
300 mg 1 times / day steady, oral Studied dose	healthy, mean age 35.6 years	Disc. AE: Vomiting, Nausea... Other AEs: Dizziness, Vomiting...
100 mg 1 times / day steady, intravenous Studied dose	healthy, mean age 38 years	Other AEs: Headache, Nausea...
600 mg 1 times / day single, intravenous Highest studied dose	healthy, young	DLT: ALT increased...

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AEs

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AE	Significance	Dose	Population
Nausea	grade 1-2, 16.7%	600 mg 1 times / day steady, oral Highest studied dose	healthy, mean age 35.6 years
ALT increased	grade 1-2, 4.2%	600 mg 1 times / day steady, oral Highest studied dose	healthy, mean age 35.6 years
Dizziness	grade 1-2, 4.2%	600 mg 1 times / day steady, oral Highest studied dose	healthy, mean age 35.6 years
Vomiting	grade 1-2, 4.2%	600 mg 1 times / day steady, oral Highest studied dose	healthy, mean age 35.6 years
Diarrhea	grade 1-2, 8.3%	600 mg 1 times / day steady, oral Highest studied dose	healthy, mean age 35.6 years

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG
	inhibitor 2,438 inducer 440	inhibitor 2,507	inhibitor 2,217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A1 132 CYP1A2 2,153 CYP2A6 879 CYP2B6 926 CYP2C8 1,057 CYP2C19 2,057 CYP2E1 1,060 CYP3A4/5 296 BCRP 910 MRP2 499 OAT1 725 OAT3 747 OCT2 779 OATP1B1 1,079 OATP1B3 961	CYP 303 UGT1A1 479 FMO 34 BCRP 697 MRP2 252 OAT1 395 OAT3 391 OCT2 434 P-gp 2,052 OATP1B1 503 OATP1B3 435	CYP2C19 329 CYP1A2 832 CYP2B6 669 CYP1B1 71 CYP2C8 198 UGT1A1 78

Drug as perpetrator

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Target	Modality	Activity
BCRP 985	inhibitor 4,027	no
CYP1A1 272	inhibitor 4,027	no
CYP1A2 2,333	inducer 1,966	no
CYP1A2 2,333	inhibitor 4,027	no
CYP1B1 93	inducer 1,966	no

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Drug as victim

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Target	Modality	Activity	Clinical evidence
P-gp 2,052	substrate 4,014	likely	weak (co-administration study)
BCRP 697	substrate 4,014	no
CYP 303	substrate 4,014	no
FMO 34	substrate 4,014	no
MRP2 252	substrate 4,014	no

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Tox targets

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Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2,263	inhibitor 2,237

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
Achemtek	0101-001954	http://www.achemtek.com/389139-83-3
Achemtek	0102-013437	http://www.achemtek.com/389139-89-3
ApexBio Technology	A3172	http://www.apexbt.com/amadacycline-methanesulfonate.html
Aurum Pharmatech LLC	W-5819	http://www.Aurumpharmatech.com/Product/ProductDetails/W_5819
BioChemPartner	BCP12946	http://www.biochempartner.com/389139-89-3-BCP12946

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PubMed

Title	Date	PubMed
Mechanism of action of the novel aminomethylcycline antibiotic omadacycline.	2014	24041885

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: Other

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.

Show entries

Name

Type

Language

OMADACYCLINE

Official Name

English

BAY 73-6944

Preferred Name

English

Omadacycline [WHO-DD]

Common Name

English

OMADACYCLINE [MI]

Common Name

English

omadacycline [INN]

Common Name

English

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Classification Tree

Code System

Code

Designated

FDA ORPHAN DRUG

741020

Anti-Infective Agent

NCI_THESAURUS

C258

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Code System

Code

Type

Description

EPA CompTox

DTXSID201027687

PRIMARY

SMS_ID

100000166996

PRIMARY

PUBCHEM

54697325

PRIMARY

EVMPD

SUB181298

PRIMARY

CAS

389139-89-3

PRIMARY

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ACTIVE MOIETY


					090IP5RV8F

OMADACYCLINE

SALT/SOLVATE (PARENT)


					5658Y89YCD

OMADACYCLINE TOSYLATE

SMILES

InChI

CNS Activity

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Funbound

Doses

AEs

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Tox targets

Sourcing

PubMed

Patents

Sample Use Guides

C_max

T_1/2

F_unbound

Drug as perpetrator