omadacycline 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | PK/Tox | Related Drugs | BioActivity |

Stem definitionDrug idCAS RN
antibiotics, protein-synthesis inhibitors, tetracycline derivatives 5299 389139-89-3

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • omadacycline
  • omadacycline tosylate
  • nuzyra
  • PTK 0796
  • amadacycline
  • BAY 73-6944
  • BAY 73-7388
  • MK-2764
  • neopentyl aminomethylminocycline
  • ZL 2401
Omadacycline is an aminomethylcycline antibacterial within the tetracycline class of antibacterial drugs. Omadacycline binds to the 30S ribosomal subunit and blocks protein synthesis. Omadacycline is active in vitro against Gram positive bacteria expressing tetracycline resistance active efflux pumps (tetK and tet L) and ribosomal protection proteins (tet M). In general, omadacycline is considered bacteriostatic; however, omadacycline has demonstrated bactericidal activity against some isolates of S. pneumoniae and H. influenzae.
  • Molecular weight: 556.66
  • Formula: C29H40N4O7
  • CLOGP: 1.22
  • LIPINSKI: 3
  • HAC: 11
  • HDO: 6
  • TPSA: 176.66
  • ALOGS: -3.42
  • ROTB: 7
  • Status: ONP
    • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
0.30 g O
0.10 g P

ADMET properties:

PropertyValueReference
Vd (Volume of distribution) 2.70 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 2.34 mL/min/kg Lombardo F, Berellini G, Obach RS
t_half (Half-life) 15 hours Lombardo F, Berellini G, Obach RS
S (Water solubility) 100 mg/mL Bocci G, Oprea TI, Benet LZ
BDDCS (Biopharmaceutical Drug Disposition Classification System) 3 Bocci G, Oprea TI, Benet LZ
BA (Bioavailability) 34.50 %

Predicted pharmacokinetic/toxicological properties (PK-AZ):

PropertyDescriptionValueUnitConfidenceSimilarity
kinase-safety-class ACVR2A,ACVR2B,ACVRL1,AKT2,AKT3,AURKA,AXL,BRAF,BTK,CAMK2B,CAMK2D,CDK2,CDK4,CDK5,CDK9,DDR1,DYRK1B,EGFR,EIF2AK3,EPHB4,ERBB2,FLT3,GRK2,GRK3,GSK3B,IKBKB,ITK,JAK1,JAK2,JAK3,KDR,KIT,MAP2K6,MAP3K14,MAP3K21,MAP3K7,MAP4K1,MAPK10,MAPK7,MAPK9,MAPKAPK2,MAPKAPK5,MARK4,NTRK2,PDK1,PDK2,PDK4,PDPK1,PIK3CA,PIK3CB,PIM2,PLK1,PLK2,PLK3,PRKCD,PRKDC,SIK2,SIK3,STK33,SYK,TEK,TGFBR1,TTK,ULK1,ZAP70 65
kinase-selectivity-class AXL,BRAF,CDK4,CDK9,EIF2AK3,EPHB4,GRK2,MAP2K6,MAP3K7,MAPK7,SIK2,STK33,SYK,TEK 14
pfas-class PFAS structural alert (1 = True, 0 = False) 0
pld-class Phospholipidosis risk class (1 = positive, 0 = negative) 1 Moderate 0.68

Approvals:

DateAgencyCompanyOrphan
Oct. 2, 2018 FDA PARATEK PHARMS INC

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Off label use 135.33 41.72 106 945 1102146 89525250
Tooth discolouration 62.49 41.72 11 1040 1187 90626209
Aspartate aminotransferase increased 55.60 41.72 26 1025 102911 90524485
Nausea 54.44 41.72 65 986 1110251 89517145
Alanine aminotransferase increased 46.30 41.72 24 1027 118314 90509082

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Hepatic function abnormal 84.31 42.94 33 786 51534 42568982
Off label use 73.69 42.94 74 745 638261 41982255
Incorrect dose administered 62.94 42.94 27 792 52947 42567569
Mycobacterium abscessus infection 48.88 42.94 9 810 751 42619765

FDA Adverse Event Reporting System (Geriatric)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Off label use 155.60 38.11 143 1426 1500042 109087688
Hepatic function abnormal 96.38 38.11 39 1530 89256 110498474
Incorrect dose administered 74.60 38.11 34 1535 103607 110484123
Aspartate aminotransferase increased 63.37 38.11 35 1534 159901 110427829
Electrocardiogram QT prolonged 60.77 38.11 30 1539 108930 110478800
Alanine aminotransferase increased 48.61 38.11 31 1538 183742 110403988
Incorrect product administration duration 48.49 38.11 16 1553 20482 110567248
Skin hyperpigmentation 38.56 38.11 11 1558 8685 110579045

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC J01AA15 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIBACTERIALS FOR SYSTEMIC USE
TETRACYCLINES
Tetracyclines
FDA CS M0021223 Tetracyclines
FDA EPC N0000175938 Tetracycline-class Antibacterial
CHEBI has role CHEBI:33282 antibacterial agent
CHEBI has role CHEBI:35441 antiinfective agent

Related Drugs by ATC class:

J01AA Tetracyclines 13 drugs
chlortetracyclineclomocyclinedemeclocyclinedoxycyclinelymecyclinemetacyclineminocyclineoxytetracyclinepenimepicyclinerolitetracyclinesarecyclinetetracycline show all 13 →

Drug Use | Suggest Off label Use Form| |View source of the data|

DiseaseRelationSNOMED_IDDOID
Bacterial pneumonia indication 53084003 DOID:874
Bacterial infection of skin indication 128936008




🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 3.13 acidic
pKa2 6.89 acidic
pKa3 11.34 acidic
pKa4 11.96 acidic
pKa5 13.08 acidic
pKa6 10.7 Basic
pKa7 9.41 Basic
pKa8 5.81 Basic

Orange Book patent data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent use
EQ 150MG BASE NUZYRA PARATEK PHARMS N209816 Oct. 2, 2018 RX TABLET ORAL 10124014 March 5, 2029 TREATMENT OF BACTERIAL SKIN AND SKIN STRUCTURE INFECTION
EQ 150MG BASE NUZYRA PARATEK PHARMS N209816 Oct. 2, 2018 RX TABLET ORAL 9724358 March 5, 2029 TREATMENT OF BACTERIAL SKIN AND SKIN STRUCTURE INFECTIONS
EQ 100MG BASE/VIAL NUZYRA PARATEK PHARMS N209817 Oct. 2, 2018 RX POWDER INTRAVENOUS 10124014 March 5, 2029 TREATMENT OF BACTERIAL SKIN AND SKIN STRUCTURE INFECTION
EQ 100MG BASE/VIAL NUZYRA PARATEK PHARMS N209817 Oct. 2, 2018 RX POWDER INTRAVENOUS 9724358 March 5, 2029 TREATMENT OF BACTERIAL SKIN AND SKIN STRUCTURE INFECTIONS
EQ 150MG BASE NUZYRA PARATEK PHARMS N209816 Oct. 2, 2018 RX TABLET ORAL 9265740 Oct. 24, 2030 TREATMENT OF BACTERIAL SKIN AND SKIN STRUCTURE INFECTIONS
EQ 150MG BASE NUZYRA PARATEK PHARMS N209816 Oct. 2, 2018 RX TABLET ORAL 10111890 Aug. 3, 2037 TREATMENT OF SUBJECTS HAVING BACTERIAL SKIN OR SKIN STRUCTURE INFECTION
EQ 150MG BASE NUZYRA PARATEK PHARMS N209816 Oct. 2, 2018 RX TABLET ORAL 10383884 Oct. 31, 2037 TREATMENT OF COMMUNITY ACQUIRED BACTERIAL PNEUMONIA
EQ 150MG BASE NUZYRA PARATEK PHARMS N209816 Oct. 2, 2018 RX TABLET ORAL 10835542 Oct. 31, 2037 TREATMENT OF COMMUNITY ACQUIRED BACTERIAL PNEUMONIA
EQ 100MG BASE/VIAL NUZYRA PARATEK PHARMS N209817 Oct. 2, 2018 RX POWDER INTRAVENOUS 10383884 Oct. 31, 2037 TREATMENT OF COMMUNITY ACQUIRED BACTERIAL PNEUMONIA
EQ 100MG BASE/VIAL NUZYRA PARATEK PHARMS N209817 Oct. 2, 2018 RX POWDER INTRAVENOUS 10835542 Oct. 31, 2037 TREATMENT OF COMMUNITY ACQUIRED BACTERIAL PNEUMONIA

Orange Book exclusivity data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRouteExclusivity dateDescription
EQ 150MG BASE NUZYRA PARATEK PHARMS N209816 Oct. 2, 2018 RX TABLET ORAL Oct. 2, 2023 NEW CHEMICAL ENTITY
EQ 100MG BASE/VIAL NUZYRA PARATEK PHARMS N209817 Oct. 2, 2018 RX POWDER INTRAVENOUS Oct. 2, 2023 NEW CHEMICAL ENTITY
EQ 150MG BASE NUZYRA PARATEK PHARMS N209816 Oct. 2, 2018 RX TABLET ORAL Oct. 2, 2028 GENERATING ANTIBIOTIC INCENTIVES NOW
EQ 100MG BASE/VIAL NUZYRA PARATEK PHARMS N209817 Oct. 2, 2018 RX POWDER INTRAVENOUS Oct. 2, 2028 GENERATING ANTIBIOTIC INCENTIVES NOW
EQ 150MG BASE NUZYRA PARATEK PHARMS N209816 Oct. 2, 2018 RX TABLET ORAL May 13, 2029 ADDITION OF INFORMATION TO THE LABELING FROM A CLINICAL STUDY
EQ 100MG BASE/VIAL NUZYRA PARATEK PHARMS N209817 Oct. 2, 2018 RX POWDER INTRAVENOUS May 13, 2029 ADDITION OF INFORMATION TO THE LABELING FROM A CLINICAL STUDY

Bioactivity Summary:

None

External reference:

IDSource
090IP5RV8F UNII
1075240-43-5 SECONDARY_CAS_RN
4038061 VANDF
C2983838 UMLSCUI
U3B PDB_CHEM_ID
CHEMBL1689772 ChEMBL_ID
54697325 PUBCHEM_CID
DB12455 DRUGBANK_ID
CHEMBL2103854 ChEMBL_ID
D09647 KEGG_DRUG
9186 INN_ID
C000591640 MESH_SUPPLEMENTAL_RECORD_UI
C545884 MESH_SUPPLEMENTAL_RECORD_UI
10839 IUPHAR_LIGAND_ID
781644002 SNOMEDCT_US
781654003 SNOMEDCT_US
CHEBI:750496 CHEBI
294191 MMSL
35300 MMSL
d09004 MMSL
017788 NDDF
017789 NDDF
2059268 RXNORM

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
NUZYRA HUMAN PRESCRIPTION DRUG LABEL 1 71715-001 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 100 mg INTRAVENOUS NDA 34 sections
NUZYRA HUMAN PRESCRIPTION DRUG LABEL 1 71715-002 TABLET, FILM COATED 150 mg ORAL NDA 34 sections