OMADACYCLINE TOSYLATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C29H40N4O7.C7H8O3S
Molecular Weight	728.852
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1=CC=C(C=C1)S(O)(=O)=O.[H][C@@]23CC4=C(C=C(CNCC(C)(C)C)C(O)=C4C(=O)C2=C(O)[C@]5(O)C(=O)C(C(N)=O)=C(O)[C@@H](N(C)C)[C@]5([H])C3)N(C)C

InChI

InChIKey=SETFNHZTVGTBHC-XGLFQKEBSA-N

InChI=1S/C29H40N4O7.C7H8O3S/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;1-6-2-4-7(5-3-6)11(8,9)10/h10,13,16,21,31,34,36-37,40H,8-9,11-12H2,1-7H3,(H2,30,39);2-5H,1H3,(H,8,9,10)/t13-,16-,21-,29-;/m0./s1

HIDE SMILES / InChI

Description
Sources: https://www.businesswire.com/news/home/20060309005111/en/Merck-Paratek-Pharmaceuticals-Sign-Collaboration-Agreement-Antibiotic | https://www.drugs.com/monograph/omadacycline-tosylate.html

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 Target ID: CHEMBL2364096 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24041885	Inhibitor 8297		1.96 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Acute bacterial skin and skin structure infections 2 Sources: https://www.drugs.com/monograph/omadacycline-tosylate.html	Curative	Approved 8429	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 2018
Community-acquired bacterial pneumonia 11 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/209816_209817lbl.pdf	Curative	Approved 8429	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 2018
Cystitis 27 Sources: https://clinicaltrials.gov/ct2/show/NCT03425396	Curative	Phase II 1132	Unknown Approved Use Unknown
Acute Pyelonephritis 2 Sources: https://clinicaltrials.gov/ct2/show/NCT03757234	Curative	Phase II 1132	Unknown Approved Use Unknown

C_max

Value	Dose	Analyte	Population
952 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/209816_209817lbl.pdf	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/209816_209817lbl.pdf	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/209816_209817lbl.pdf	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/209816_209817lbl.pdf	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/209816_209817lbl.pdf	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/209816_209817lbl.pdf	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 OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/209816Orig1s000,209817Orig1s000MultidisciplineR.pdf	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 OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/209816Orig1s000,209817Orig1s000MultidisciplineR.pdf	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

Value	Dose	Analyte	Population
11156 ng × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/209816_209817lbl.pdf	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/209816_209817lbl.pdf	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/209816_209817lbl.pdf	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/209816_209817lbl.pdf	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/209816_209817lbl.pdf	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/209816_209817lbl.pdf	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 OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/209816Orig1s000,209817Orig1s000MultidisciplineR.pdf	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 OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/209816Orig1s000,209817Orig1s000MultidisciplineR.pdf	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

T_1/2

Value	Dose	Analyte	Population
15.5 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/209816_209817lbl.pdf	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/209816_209817lbl.pdf	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/209816_209817lbl.pdf	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/209816_209817lbl.pdf	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/209816_209817lbl.pdf	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/209816_209817lbl.pdf	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 OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/209816Orig1s000,209817Orig1s000MultidisciplineR.pdf	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 OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/209816Orig1s000,209817Orig1s000MultidisciplineR.pdf	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

F_unbound

Value	Dose	Analyte	Population
80% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/209816_209817lbl.pdf	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% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/209816_209817lbl.pdf	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% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/209816_209817lbl.pdf	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% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/209816_209817lbl.pdf	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% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/209816_209817lbl.pdf	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% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/209816_209817lbl.pdf	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

Dose	Population	Adverse 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: https://pubmed.ncbi.nlm.nih.gov/29180524/	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: https://pubmed.ncbi.nlm.nih.gov/29180524/	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: https://pubmed.ncbi.nlm.nih.gov/29180524/
600 mg 1 times / day steady, oral MTD\|Highest studied dose Dose: 600 mg, 1 times / day Route: oral Route: steady Dose: 600 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/209816Orig1s000,209817Orig1s000MultidisciplineR.pdf https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/209816Orig1s000,209817Orig1s000OtherR.pdf	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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/209816Orig1s000,209817Orig1s000MultidisciplineR.pdf https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/209816Orig1s000,209817Orig1s000OtherR.pdf	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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/209816Orig1s000,209817Orig1s000MultidisciplineR.pdf https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/209816Orig1s000,209817Orig1s000OtherR.pdf
300 mg 1 times / day steady, oral Studied dose Dose: 300 mg, 1 times / day Route: oral Route: steady Dose: 300 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/209816Orig1s000,209817Orig1s000MultidisciplineR.pdf https://pubmed.ncbi.nlm.nih.gov/29180524/	healthy, mean age 35.6 years n = 26 Health Status: healthy Age Group: mean age 35.6 years Sex: M+F Population Size: 26 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/209816Orig1s000,209817Orig1s000MultidisciplineR.pdf https://pubmed.ncbi.nlm.nih.gov/29180524/	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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/209816Orig1s000,209817Orig1s000MultidisciplineR.pdf https://pubmed.ncbi.nlm.nih.gov/29180524/
100 mg 1 times / day steady, intravenous Studied dose Dose: 100 mg, 1 times / day Route: intravenous Route: steady Dose: 100 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/209816Orig1s000,209817Orig1s000MultidisciplineR.pdf https://pubmed.ncbi.nlm.nih.gov/28696233/	healthy, mean age 38 years n = 42 Health Status: healthy Age Group: mean age 38 years Sex: M+F Population Size: 42 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/209816Orig1s000,209817Orig1s000MultidisciplineR.pdf https://pubmed.ncbi.nlm.nih.gov/28696233/	Other AEs: Headache, Nausea... Other AEs: Headache (grade 1-2, 11.9%) Nausea (grade 1-2, 2.4%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/209816Orig1s000,209817Orig1s000MultidisciplineR.pdf https://pubmed.ncbi.nlm.nih.gov/28696233/
600 mg 1 times / day single, intravenous Highest studied dose Dose: 600 mg, 1 times / day Route: intravenous Route: single Dose: 600 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/209816Orig1s000,209817Orig1s000MultidisciplineR.pdf https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/209816Orig1s000,209817Orig1s000OtherR.pdf	healthy, young n = 2 Health Status: healthy Age Group: young Sex: M Population Size: 2 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/209816Orig1s000,209817Orig1s000MultidisciplineR.pdf https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/209816Orig1s000,209817Orig1s000OtherR.pdf	DLT: ALT increased... Dose limiting toxicities: ALT increased (grade 2) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/209816Orig1s000,209817Orig1s000MultidisciplineR.pdf https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/209816Orig1s000,209817Orig1s000OtherR.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/209816Orig1s000,209817Orig1s000OtherR.pdf	healthy, young Health Status: healthy Age Group: young Sex: M Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/209816Orig1s000,209817Orig1s000OtherR.pdf	Other AEs: Elevated liver enzymes... Other AEs: Elevated liver enzymes (grade 2) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/209816Orig1s000,209817Orig1s000OtherR.pdf

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
	inhibitor 1767 inducer 389	inhibitor 1852	inhibitor 1612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A1 110 CYP1A2 1524 CYP2A6 707 CYP2B6 810 CYP2C8 911 CYP2C19 1478 CYP2E1 882 CYP3A4/5 278 BCRP 699 MRP2 383 OAT1 599 OAT3 642 OCT2 647 OATP1B1 788 OATP1B3 706	CYP 270 UGT1A1 418 FMO 35 BCRP 561 MRP2 205 OAT1 326 OAT3 339 OCT2 355 P-gp 1537 OATP1B1 406 OATP1B3 350	CYP2C19 293 CYP1A2 701 CYP2B6 547 CYP1B1 51 CYP2C8 168 UGT1A1 69

Drug as perpetrator

Target	Modality	Activity	Clinical evidence
BCRP 773	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/209816Orig1s000,209817Orig1s000MultidisciplineR.pdf#page=90 Page: 90.0	no
CYP1A1 218	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/209816Orig1s000,209817Orig1s000MultidisciplineR.pdf#page=90 Page: 90.0	no
CYP1A2 1692	inducer 1573 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/209816Orig1s000,209817Orig1s000MultidisciplineR.pdf#page=90 Page: 90.0	no
CYP1A2 1692	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/209816Orig1s000,209817Orig1s000MultidisciplineR.pdf#page=85 Page: 85.0	no
CYP1B1 67	inducer 1573 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/209816Orig1s000,209817Orig1s000MultidisciplineR.pdf#page=90 Page: 90.0	no
CYP2A6 739	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/209816Orig1s000,209817Orig1s000MultidisciplineR.pdf#page=90 Page: 90.0	no
CYP2B6 1001	inducer 1573 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/209816Orig1s000,209817Orig1s000MultidisciplineR.pdf#page=90 Page: 90.0	no
CYP2B6 1001	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/209816Orig1s000,209817Orig1s000MultidisciplineR.pdf#page=90 Page: 90.0	no
CYP2C19 1553	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/209816Orig1s000,209817Orig1s000MultidisciplineR.pdf#page=90 Page: 90.0	no
CYP2C8 965	inducer 1573 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/209816Orig1s000,209817Orig1s000MultidisciplineR.pdf#page=90 Page: 90.0	no
CYP2C8 965	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/209816Orig1s000,209817Orig1s000MultidisciplineR.pdf#page=90 Page: 90.0	no
CYP2C9 1819	inducer 1573 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/209816Orig1s000,209817Orig1s000MultidisciplineR.pdf#page=90 Page: 90.0	no
CYP2C9 1819	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/209816Orig1s000,209817Orig1s000MultidisciplineR.pdf#page=90 Page: 90.0	no
CYP2D6 1891	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/209816Orig1s000,209817Orig1s000MultidisciplineR.pdf#page=90 Page: 90.0	no
CYP2E1 970	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/209816Orig1s000,209817Orig1s000MultidisciplineR.pdf#page=90 Page: 90.0	no
CYP3A4/5 335	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/209816Orig1s000,209817Orig1s000MultidisciplineR.pdf#page=90 Page: 90.0	no
MRP2 475	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/209816Orig1s000,209817Orig1s000MultidisciplineR.pdf#page=90 Page: 90.0	no
OAT1 603	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/209816Orig1s000,209817Orig1s000MultidisciplineR.pdf#page=90 Page: 90.0	no
OAT3 644	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/209816Orig1s000,209817Orig1s000MultidisciplineR.pdf#page=90 Page: 90.0	no
OATP1B1 803	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/209816Orig1s000,209817Orig1s000MultidisciplineR.pdf#page=90 Page: 90.0	no
OATP1B3 715	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/209816Orig1s000,209817Orig1s000MultidisciplineR.pdf#page=90 Page: 90.0	no
OCT2 648	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/209816Orig1s000,209817Orig1s000MultidisciplineR.pdf#page=90 Page: 90.0	no
UGT1A1 254	inducer 1573 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/209816Orig1s000,209817Orig1s000MultidisciplineR.pdf#page=90 Page: 90.0	no
CYP2C19 1553	inducer 1573 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/209816Orig1s000,209817Orig1s000MultidisciplineR.pdf#page=90 Page: 90.0	weak	unlikely Comment: shown to be a weak inducer of CYP2C19 at a concentration 5 -fold higher than Cmax Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/209816Orig1s000,209817Orig1s000MultidisciplineR.pdf#page=90 Page: 90.0

Drug as victim

Target	Modality	Activity	Clinical evidence
P-gp 1537	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/209816Orig1s000,209817Orig1s000MultidisciplineR.pdf#page=90 Page: 90.0	likely	weak (co-administration study) Comment: Verapamil dosing increased the omadacycline AUC by approximately 18% and the Cmax by 14% Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/209816Orig1s000,209817Orig1s000MultidisciplineR.pdf#page=90 Page: 90.0
BCRP 561	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/209816Orig1s000,209817Orig1s000MultidisciplineR.pdf#page=90 Page: 90.0	no
CYP 270	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/209816Orig1s000,209817Orig1s000MultidisciplineR.pdf#page=51 Page: 51.0	no
FMO 35	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/209816Orig1s000,209817Orig1s000MultidisciplineR.pdf#page=51 Page: 51.0	no
MRP2 205	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/209816Orig1s000,209817Orig1s000MultidisciplineR.pdf#page=90 Page: 90.0	no
OAT1 326	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/209816Orig1s000,209817Orig1s000MultidisciplineR.pdf#page=90 Page: 90.0	no
OAT3 339	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/209816Orig1s000,209817Orig1s000MultidisciplineR.pdf#page=90 Page: 90.0	no
OATP1B1 406	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/209816Orig1s000,209817Orig1s000MultidisciplineR.pdf#page=90 Page: 90.0	no
OATP1B3 350	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/209816Orig1s000,209817Orig1s000MultidisciplineR.pdf#page=90 Page: 90.0	no
OCT2 355	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/209816Orig1s000,209817Orig1s000MultidisciplineR.pdf#page=90 Page: 90.0	no
UGT1A1 418	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/209816Orig1s000,209817Orig1s000MultidisciplineR.pdf#page=51 Page: 51.0	no

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1647	inhibitor 1626 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/209816Orig1s000,209817Orig1s000MultidisciplineR.pdf#page=45 Page: 45;347

Sourcing

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
Chem Scene	CS-1338	http://www.chemscene.com/389139-89-3.html
Chemspace	CSSS00025757005	https://chem-space.com/CSSS00025757005
Excenen	EX-A4252	https://www.excenen.com/searchresultlist.php?id=EX-A4252
Lab Network	LN01342729	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01342729
MedChem Express	HY-14865	https://www.medchemexpress.com/omadacycline.html
MolPort	MolPort-046-418-167	https://www.molport.com/shop/molecule-link/MolPort-046-418-167
MuseChem	I008447	https://www.musechem.com/product/I008447.html
Smolecule	S538061	http://www.smolecule.com/products/s538061
THE BioTek	bt-277374	https://www.thebiotek.com/product/inhibitors/bt-277374
eNovation Chemicals	D666957	https://www.enovationchem.com/ProductDetails.asp?ProductID=D666957

PubMed

Title	Date	PubMed
Mechanism of action of the novel aminomethylcycline antibiotic omadacycline.	2014	24041885
Omadacycline for Acute Bacterial Skin and Skin-Structure Infections.	2019 Feb 7	30726689
Omadacycline for Community-Acquired Bacterial Pneumonia.	2019 Feb 7	30726692

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.

Name

Type

Language

OMADACYCLINE TOSYLATE

Official Name

English

OMADACYCLINE TOSYLATE [MI]

Common Name

English

PTK-0796

Code

English

OMADACYCLINE TOSILATE

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)-, 4-METHYLBENZENESULFONATE (1:1)

Common Name

English

Omadacycline tosilate [WHO-DD]

Common Name

English

OMADACYCLINE TOSYLATE [ORANGE BOOK]

Common Name

English

PTK 0796

Code

English

NUZYRA

Brand Name

English

OMADACYCLINE TOSYLATE [USAN]

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 MONO(4-METHYBENZENESULFONATE) (SALT)

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C258