Omadacycline

Identification

Summary

Omadacycline is a tetracycline antibiotic used to treat community acquired bacterial pneumonia.

Brand Names

Nuzyra

Generic Name

Omadacycline

DrugBank Accession Number

DB12455

Background

Omadacycline has been used in trials studying the treatment of Bacterial Pneumonia, Bacterial Infections, Community-Acquired Infections, and Skin Structures and Soft Tissue Infections. Omadacycline represents a significant advance over the well-known tetracycline family, and has been shown to be highly effective in animal models at treating increasingly problematic, clinically prevalent infections caused by gram-positive bacteria, such as methicillin-resistant Staphylococcus aureus (MRSA), and by gram-negative, atypical and anaerobic bacteria, including those resistant to currently available classes of antibiotics and known to cause diseases such as pneumonias, urinary tract infections, skin diseases and blood-borne infections in both the hospital and community settings.

Type

Small Molecule

Groups

Approved, Investigational

Structure

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MOLSDFPDBSMILESInChI

Similar Structures

Structure for Omadacycline (DB12455)

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Weight

Average: 556.66
Monoisotopic: 556.289699644

Chemical Formula

C₂₉H₄₀N₄O₇

Synonyms

• Amadacycline
• Omadacycline

External IDs

• BAY 73-6944

Pharmacology

Indication

Omadacycline is indicated for the treatment of community acquired bacterial pneumonia and acute bacterial skin and skin structure infections caused by omadacycline-susceptible organisms in adults.^Label

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Associated Conditions

• Acute Bacterial Skin and Skin Structure Infection (ABSSSI)
• Community-Acquired Bacterial Pneumonia (CABP)

Contraindications & Blackbox Warnings

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Pharmacodynamics

Omadacycline can be either bacteriostatic or bacteriocidal depending on the organism involved.^1,3 It disrupts bacterial protein synthesis without affecting DNA, RNA, or peptidoglycan synthesis. Omadacycline represents an improvement over existing tetracycline agents as it has not been found to be subject to tetracycline resistance mediated by tetracycline efflux pumps encoded by the tet(K), tet(L), and tet(B) or to ribosomal protection proteins encoded by tet(O) and tet(M).^Label,1,2 Omadacycline is susceptible to RNA mutations which confer resistance to tetracyclines.⁴

Mechanism of action

Omadacycline binds to the primary tetracycline binding site on the bacterial 30s ribosomal subunit with high specificity.⁴ There it acts to block protein synthesis, disrupting many facets of cellular function and resulting in either cell death or stasis.^1,2,3

Target	Actions	Organism
A30S ribosomal protein S3	inhibitor	Escherichia coli (strain K12)
A30S ribosomal protein S7	inhibitor	Escherichia coli (strain K12)
A30S ribosomal protein S8	inhibitor	Escherichia coli (strain K12)
A30S ribosomal protein S19	inhibitor	Escherichia coli (strain K12)
A30S ribosomal protein S14	inhibitor	Escherichia coli (strain K12)
A16S ribosomal RNA	inhibitor	Enteric bacteria and other eubacteria

Absorption

Omadacycline has an mean absolute oral bioavailability of 34.5% and a mean Tmax of2.5 h with oral dosing. With multiple dosing, Omadacycline displays an accumulation factor of 1.5. ^Label Official labeling states that food does not significantly impact rate or extent of absorption, however, conflicting data exists suggesting food may lower the bioavailability of omadacycline taken after eating. ^Label,5 The exposure in alveolar cells and epithelial lining fluid is 25.8 and 1.5 fold higher than plasma exposure after IV administration, suggesting Omadacycline penetrates the lungs to a significant degree.^Label

Volume of distribution

Omadacycline has a mean Vd of 256 L after a single dose and a Vss of 190 L.^Label

Protein binding

Omadacycline exhibits non-linear protein binding and remains 20% bound independent of concentration.^Label

Metabolism

Omadacycline is not known to be metabolized in humans.^Label

Route of elimination

After IV dosing 27% of Omadacycline was eliminated by the kidneys. In oral dosing 14.4% was found to be eliminated by the kidneys and 81.1% in the feces.^Label Neither renal nor hepatic impairment appears to produce a clinically relevant effect elimination.

Half-life

Omadacycline has a mean half life of elimination of 16.2 h. ^Label

Clearance

Omadacycline has a mean systemic clearance of 11.24 L/h and a renal clearance of 2.4-3.3 L/h.^Label

Adverse Effects

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Toxicity

No carcinogenicity studies have been conducted with Omadacycline, however, other tetracycline drugs have shown oncogenicity.^Label Specifically, oxytetracycline increased incidence of adrenal and pituitary tumors and minocycline increased incidence of thyroid tumors.

Omadacycline has tested positive for clastogenicity and aneugenicity during in-vitro Chinese hamster ovary cell studies and for mutagenicity in mouse lymphoma cells.^Label Both positive results occurred in the presence of metabolizing enzymes. Omadacycline has tested negative for chromosomal aberration of any kind during in-vitro Chinese hamster V79 cell testing. It has further tested negative during in-vivo micronucleus assays in ICR mice and HanRcc: WIST rats.

Omadacycline reduced sperm counts and sperm-motility in male rats at repeat dosages equivalent to 1.3 times the normal human exposure but produced no effect on fertility parameters.^Label Inhibition of spermatogenesis was noted at repeat dosages equivalent to 6-8 times normal human exposure for a duration greater than 37 days but not at dosages under 2 times normal human exposure or durations of less than 4 weeks. Ovulation and embryonic survival was reduced in female rats at dosages approximating normal human exposure administered before mating through early pregnancy.

Thyroid hyperpigmentation, goitrogenicity, thyroid hyperplasia, and adrenal have been noted in multiple animal studies using other tetracycline drugs.^Label

Pathways

Not Available

Pharmacogenomic Effects/ADRs

Not Available

Interactions

Drug Interactions

This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

• Approved
• Vet approved
• Nutraceutical
• Illicit
• Withdrawn
• Investigational
• Experimental
• All Drugs

Drug	Interaction
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Abemaciclib	The serum concentration of Abemaciclib can be increased when it is combined with Omadacycline.
Abrocitinib	The serum concentration of Omadacycline can be increased when it is combined with Abrocitinib.
Acenocoumarol	Omadacycline may increase the anticoagulant activities of Acenocoumarol.
Acitretin	The risk or severity of pseudotumor cerebri can be increased when Acitretin is combined with Omadacycline.
Adagrasib	The serum concentration of Omadacycline can be increased when it is combined with Adagrasib.
Afatinib	The serum concentration of Omadacycline can be increased when it is combined with Afatinib.
Alitretinoin	The risk or severity of pseudotumor cerebri can be increased when Alitretinoin is combined with Omadacycline.
Almasilate	Almasilate can cause a decrease in the absorption of Omadacycline resulting in a reduced serum concentration and potentially a decrease in efficacy.
Aluminium	Aluminium can cause a decrease in the absorption of Omadacycline resulting in a reduced serum concentration and potentially a decrease in efficacy.
Aluminium phosphate	Aluminium phosphate can cause a decrease in the absorption of Omadacycline resulting in a reduced serum concentration and potentially a decrease in efficacy.

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Food Interactions

• Avoid multivalent ions. Wait at least 4 hours after the omadacycline administration to take multivalent cations (eg. zinc, calcium, magnesium, and iron).
• Take on an empty stomach. Do not eat for 4 hours before and 2 hours after administering omadacycline. Drinking water after administration is acceptable.
• Take separate from antacids. Wait at least 4 hours after omadacycline administration to take antacids.

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Product Ingredients

Ingredient	UNII	CAS	InChI Key
Omadacycline tosylate	5658Y89YCD	1075240-43-5	SETFNHZTVGTBHC-XGLFQKEBSA-N

Brand Name Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
Nuzyra	Tablet, film coated	150 mg/1	Oral	Paratek Pharmaceuticals, Inc.	2019-02-01	Not applicable
Nuzyra	Injection, powder, lyophilized, for solution	100 mg/5mL	Intravenous	Paratek Pharmaceuticals, Inc.	2019-02-01	Not applicable

Categories

ATC Codes

J01AA15 — Omadacycline

• J01AA — Tetracyclines
• J01A — TETRACYCLINES
• J01 — ANTIBACTERIALS FOR SYSTEMIC USE
• J — ANTIINFECTIVES FOR SYSTEMIC USE

J01AA20 — Combinations of tetracyclines

• J01AA — Tetracyclines
• J01A — TETRACYCLINES
• J01 — ANTIBACTERIALS FOR SYSTEMIC USE
• J — ANTIINFECTIVES FOR SYSTEMIC USE

Drug Categories

• Anti-Bacterial Agents
• Antibacterials for Systemic Use
• Antiinfectives for Systemic Use
• Naphthacenes
• P-glycoprotein substrates
• Tetracyclines

Chemical TaxonomyProvided by Classyfire

Description

This compound belongs to the class of organic compounds known as tetracyclines. These are polyketides having an octahydrotetracene-2-carboxamide skeleton, substituted with many hydroxy and other groups.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Tetracyclines

Sub Class

Not Available

Direct Parent

Tetracyclines

Alternative Parents

Naphthacenes / Anthracenecarboxylic acids and derivatives / Tetralins / Aryl ketones / Dialkylarylamines / Aralkylamines / Cyclohexenones / Phenols / Tertiary alcohols / Vinylogous acids / Primary carboxylic acid amides / Trialkylamines / Amino acids and derivatives / Enols / Dialkylamines / Polyols / Hydrocarbon derivatives / Organic oxides

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Substituents

Alcohol / Amine / Amino acid or derivatives / Anthracene carboxylic acid or derivatives / Aralkylamine / Aromatic homopolycyclic compound / Aryl ketone / Benzenoid / Carbonyl group / Carboxamide group / Carboxylic acid derivative / Cyclohexenone / Dialkylarylamine / Enol / Hydrocarbon derivative / Ketone / Naphthacene / Organic nitrogen compound / Organic oxide / Organic oxygen compound / Organonitrogen compound / Organooxygen compound / Phenol / Polyol / Primary carboxylic acid amide / Secondary aliphatic amine / Secondary amine / Tertiary alcohol / Tertiary aliphatic amine / Tertiary aliphatic/aromatic amine / Tertiary amine / Tetracene / Tetracycline / Tetralin / Vinylogous acid

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Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

Affected organisms

• Streptococcus pyogenes
• Streptococcus pneumoniae
• Haemophilus influenzae
• Mycoplasma pneumoniae
• Legionella pneumophila
• Staphylococcus aureus
• Enterococcus faecalis
• Staphylococcus lugdunensis
• Streptococcus anginosus
• Streptococcus constellatus
• Enterobacter cloacae
• Klebsiella pneumoniae
• Haemophilus parainfluenzae
• Streptococcus intermedius
• Chlamydophila pneumoniae

Chemical Identifiers

UNII

090IP5RV8F

CAS number

389139-89-3

InChI Key

JEECQCWWSTZDCK-IQZGDKDPSA-N

InChI

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

IUPAC Name

(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

SMILES

[H][C@@]12CC3=C(C=C(CNCC(C)(C)C)C(O)=C3C(=O)C1=C(O)[C@]1(O)C(=O)C(C(N)=O)=C(O)[C@@H](N(C)C)[C@]1([H])C2)N(C)C

References

General References

1. Barber KE, Bell AM, Wingler MJB, Wagner JL, Stover KR: Omadacycline Enters the Ring: A New Antimicrobial Contender. Pharmacotherapy. 2018 Oct 5. doi: 10.1002/phar.2185. [Article]
2. Draper MP, Weir S, Macone A, Donatelli J, Trieber CA, Tanaka SK, Levy SB: Mechanism of action of the novel aminomethylcycline antibiotic omadacycline. Antimicrob Agents Chemother. 2014;58(3):1279-83. doi: 10.1128/AAC.01066-13. Epub 2013 Sep 16. [Article]
3. Tanaka SK, Steenbergen J, Villano S: Discovery, pharmacology, and clinical profile of omadacycline, a novel aminomethylcycline antibiotic. Bioorg Med Chem. 2016 Dec 15;24(24):6409-6419. doi: 10.1016/j.bmc.2016.07.029. Epub 2016 Jul 18. [Article]
4. Heidrich CG, Mitova S, Schedlbauer A, Connell SR, Fucini P, Steenbergen JN, Berens C: The Novel Aminomethylcycline Omadacycline Has High Specificity for the Primary Tetracycline-Binding Site on the Bacterial Ribosome. Antibiotics (Basel). 2016 Sep 22;5(4). pii: antibiotics5040032. doi: 10.3390/antibiotics5040032. [Article]
5. Tzanis E, Manley A, Villano S, Tanaka SK, Bai S, Loh E: Effect of Food on the Bioavailability of Omadacycline in Healthy Participants. J Clin Pharmacol. 2017 Mar;57(3):321-327. doi: 10.1002/jcph.814. Epub 2016 Sep 22. [Article]

External Links

PubChem Compound

54697325

PubChem Substance

347828696

ChemSpider

20131003

RxNav

2059269

ChEMBL

CHEMBL1689772

ZINC

ZINC000004836283

Wikipedia

Omadacycline

FDA label

Download (2.6 MB)

Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count
4	Not Yet Recruiting	Treatment	Microbial Colonization	1
4	Recruiting	Other	Cystic Fibrosis (CF)	1
3	Completed	Treatment	Bacterial Infections / Skin and skin structure infections	2
3	Completed	Treatment	Bacterial Pneumonia / Community Acquired Infections	1
3	Recruiting	Treatment	Bacterial Pneumonia / Community Acquired Pneumonia (CAP)	1
3	Terminated	Treatment	Skin Diseases, Infectious	1
3	Withdrawn	Treatment	Skin and skin structure infections	1
2	Completed	Treatment	Acute Pyelonephritis(APN)	1
2	Completed	Treatment	Bacterial skin infections / Skin Diseases, Infectious	1
2	Completed	Treatment	Cystitis / Uncomplicated Urinary Tract Infections	1

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage Forms

Form	Route	Strength
Injection, powder, lyophilized, for solution	Intravenous	100 mg/5mL
Tablet, film coated	Oral	150 mg/1

Prices

Not Available

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)	Region
US10111890	No	2018-10-30	2037-08-03
US10124014	No	2018-11-13	2029-03-05
US9265740	No	2016-02-23	2029-03-05
US9365500	No	2016-06-14	2021-06-29
US9724358	No	2017-08-08	2029-03-05
US9314475	No	2016-04-19	2031-03-18
US7326696	No	2008-02-05	2023-09-24
US7553828	No	2009-06-30	2023-06-02
US8383610	No	2013-02-26	2030-09-23
US10383884	No	2019-08-20	2037-10-31
US10835542	No	2020-11-17	2037-10-31

Properties

State

Solid

Experimental Properties

Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.213 mg/mL	ALOGPS
logP	0.94	ALOGPS
logP	-2.2	Chemaxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	2.87	Chemaxon
pKa (Strongest Basic)	10.54	Chemaxon
Physiological Charge	1	Chemaxon
Hydrogen Acceptor Count	10	Chemaxon
Hydrogen Donor Count	6	Chemaxon
Polar Surface Area	176.66 Å2	Chemaxon
Rotatable Bond Count	7	Chemaxon
Refractivity	153.93 m3·mol-1	Chemaxon
Polarizability	60.02 Å3	Chemaxon
Number of Rings	4	Chemaxon
Bioavailability	0	Chemaxon
Rule of Five	No	Chemaxon
Ghose Filter	No	Chemaxon
Veber's Rule	No	Chemaxon
MDDR-like Rule	Yes	Chemaxon

Predicted ADMET Features

Not Available

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	Not Available

Targets

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Details1. 30S ribosomal protein S3

Kind

Protein

Organism

Escherichia coli (strain K12)

Pharmacological action

Yes

Actions

Inhibitor

General Function

Structural constituent of ribosome

Specific Function

Binds the lower part of the 30S subunit head. Binds mRNA in the 70S ribosome, positioning it for translation (By similarity).Plays a role in mRNA unwinding by the ribosome, possibly by forming part...

Gene Name

rpsC

Uniprot ID

P0A7V3

Uniprot Name

30S ribosomal protein S3

Molecular Weight

25983.07 Da

References

1. Anokhina MM, Barta A, Nierhaus KH, Spiridonova VA, Kopylov AM: Mapping of the second tetracycline binding site on the ribosomal small subunit of E.coli. Nucleic Acids Res. 2004 May 11;32(8):2594-7. doi: 10.1093/nar/gkh583. Print 2004. [Article]
2. Barber KE, Bell AM, Wingler MJB, Wagner JL, Stover KR: Omadacycline Enters the Ring: A New Antimicrobial Contender. Pharmacotherapy. 2018 Oct 5. doi: 10.1002/phar.2185. [Article]

Details2. 30S ribosomal protein S7

Kind

Protein

Organism

Escherichia coli (strain K12)

Pharmacological action

Yes

Actions

Inhibitor

General Function

Trna binding

Specific Function

One of the primary rRNA binding proteins, it binds directly to 16S rRNA where it nucleates assembly of the head domain of the 30S subunit. Is located at the subunit interface close to the decoding ...

Gene Name

rpsG

Uniprot ID

P02359

Uniprot Name

30S ribosomal protein S7

Molecular Weight

20018.91 Da

References

1. Anokhina MM, Barta A, Nierhaus KH, Spiridonova VA, Kopylov AM: Mapping of the second tetracycline binding site on the ribosomal small subunit of E.coli. Nucleic Acids Res. 2004 May 11;32(8):2594-7. doi: 10.1093/nar/gkh583. Print 2004. [Article]
2. Barber KE, Bell AM, Wingler MJB, Wagner JL, Stover KR: Omadacycline Enters the Ring: A New Antimicrobial Contender. Pharmacotherapy. 2018 Oct 5. doi: 10.1002/phar.2185. [Article]

Details3. 30S ribosomal protein S8

Kind

Protein

Organism

Escherichia coli (strain K12)

Pharmacological action

Yes

Actions

Inhibitor

General Function

Structural constituent of ribosome

Specific Function

One of the primary rRNA binding proteins, it binds directly to 16S rRNA central domain where it helps coordinate assembly of the platform of the 30S subunit.Protein S8 is a translational repressor ...

Gene Name

rpsH

Uniprot ID

P0A7W7

Uniprot Name

30S ribosomal protein S8

Molecular Weight

14126.435 Da

References

1. Anokhina MM, Barta A, Nierhaus KH, Spiridonova VA, Kopylov AM: Mapping of the second tetracycline binding site on the ribosomal small subunit of E.coli. Nucleic Acids Res. 2004 May 11;32(8):2594-7. doi: 10.1093/nar/gkh583. Print 2004. [Article]
2. Barber KE, Bell AM, Wingler MJB, Wagner JL, Stover KR: Omadacycline Enters the Ring: A New Antimicrobial Contender. Pharmacotherapy. 2018 Oct 5. doi: 10.1002/phar.2185. [Article]

Details4. 30S ribosomal protein S19

Kind

Protein

Organism

Escherichia coli (strain K12)

Pharmacological action

Yes

Actions

Inhibitor

General Function

Trna binding

Specific Function

In the E.coli 70S ribosome in the initiation state (PubMed:12809609) it has been modeled to contact the 23S rRNA of the 50S subunit forming part of bridge B1a; this bridge is broken in the model wi...

Gene Name

rpsS

Uniprot ID

P0A7U3

Uniprot Name

30S ribosomal protein S19

Molecular Weight

10430.235 Da

References

1. Anokhina MM, Barta A, Nierhaus KH, Spiridonova VA, Kopylov AM: Mapping of the second tetracycline binding site on the ribosomal small subunit of E.coli. Nucleic Acids Res. 2004 May 11;32(8):2594-7. doi: 10.1093/nar/gkh583. Print 2004. [Article]
2. Barber KE, Bell AM, Wingler MJB, Wagner JL, Stover KR: Omadacycline Enters the Ring: A New Antimicrobial Contender. Pharmacotherapy. 2018 Oct 5. doi: 10.1002/phar.2185. [Article]

Details5. 30S ribosomal protein S14

Kind

Protein

Organism

Escherichia coli (strain K12)

Pharmacological action

Yes

Actions

Inhibitor

General Function

Structural constituent of ribosome

Specific Function

Binds 16S rRNA, required for the assembly of 30S particles and may also be responsible for determining the conformation of the 16S rRNA at the A site.

Gene Name

rpsN

Uniprot ID

P0AG59

Uniprot Name

30S ribosomal protein S14

Molecular Weight

11580.36 Da

References

1. Anokhina MM, Barta A, Nierhaus KH, Spiridonova VA, Kopylov AM: Mapping of the second tetracycline binding site on the ribosomal small subunit of E.coli. Nucleic Acids Res. 2004 May 11;32(8):2594-7. doi: 10.1093/nar/gkh583. Print 2004. [Article]
2. Barber KE, Bell AM, Wingler MJB, Wagner JL, Stover KR: Omadacycline Enters the Ring: A New Antimicrobial Contender. Pharmacotherapy. 2018 Oct 5. doi: 10.1002/phar.2185. [Article]

Details6. 16S ribosomal RNA

Kind

Nucleotide

Organism

Enteric bacteria and other eubacteria

Pharmacological action

Yes

Actions

Inhibitor

In prokaryotes, the 16S rRNA is essential for recognizing the 5' end of mRNA and hence positioning it correctly on the ribosome. The 16S rRNA has a characteristic secondary structure in which half of the nucleotides are base-paired. The 16S rRNA sequence has been highly conserved and is often used for evolutionary and species comparative analysis.

References

1. Anokhina MM, Barta A, Nierhaus KH, Spiridonova VA, Kopylov AM: Mapping of the second tetracycline binding site on the ribosomal small subunit of E.coli. Nucleic Acids Res. 2004 May 11;32(8):2594-7. doi: 10.1093/nar/gkh583. Print 2004. [Article]
2. Barber KE, Bell AM, Wingler MJB, Wagner JL, Stover KR: Omadacycline Enters the Ring: A New Antimicrobial Contender. Pharmacotherapy. 2018 Oct 5. doi: 10.1002/phar.2185. [Article]

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Drug created at October 20, 2016 22:27 / Updated at February 21, 2021 18:53