DANOFLOXACIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C19H20FN3O3
Molecular Weight	357.3788
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN1C[C@@H]2C[C@H]1CN2C3=CC4=C(C=C3F)C(=O)C(=CN4C5CC5)C(O)=O

InChI

InChIKey=QMLVECGLEOSESV-RYUDHWBXSA-N

InChI=1S/C19H20FN3O3/c1-21-7-12-4-11(21)8-22(12)17-6-16-13(5-15(17)20)18(24)14(19(25)26)9-23(16)10-2-3-10/h5-6,9-12H,2-4,7-8H2,1H3,(H,25,26)/t11-,12-/m0/s1

HIDE SMILES / InChI

Description
Sources: https://www.fda.gov/downloads/AnimalVeterinary/Products/ApprovedAnimalDrugProducts/FOIADrugSummaries/UCM292024.pdf | https://dailymed.nlm.nih.gov/dailymed/archives/fdaDrugInfo.cfm?archiveid=95982

Danofloxacin is a quinolone antibacterial agent for veterinary medicine. The drug is approved by FDA for the treatment of bovine infectious respiratory disease under the name Advocin (mesylate salt). Danofloxacin exerts its action by inhibiting bacterial DNA gyrase.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Bacterial DNA gyrase 66 Target ID: CHEMBL2311224 Sources: https://www.genome.jp/dbget-bin/www_bget?dr:D03646\|https://www.ncbi.nlm.nih.gov/pubmed/8726041\|https://www.ncbi.nlm.nih.gov/pubmed/26078016	Inhibitor 8504
Bacterial DNA gyrase 66 Target ID: CHEMBL2311224 Sources: https://dailymed.nlm.nih.gov/dailymed/archives/fdaDrugInfo.cfm?archiveid=95982	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Bovine infectious respiratory disease 2 Sources: https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=d22c22fc-d530-423c-8d78-ca95fe195ba1&type=display	Curative		Approved 8583	ADVOCIN Approved Use For the treatment of bovine respiratory disease (BRD) associated with Mannheimia haemolytica and Pasteurella multocida and for the control of BRD in beef cattle at high risk of developing BRD associated with Mannheimia haemolytica and Pasteurella multocida. Launch Date 2011

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252 inducer 1087	inhibitor 2438	inhibitor 2507	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2A6 879 CYP1A2 2153 CYP2E1 1060 CYP2C19 2057 CYP19A1 429	BCRP 697 MRP2 252 P-gp 2052

Drug as perpetrator

Target	Modality	Activity
CYP19A1 430	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/71335#section=BioAssay-Results Page: 110.0	inconclusive
CYP1A2 2333	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzMzU2IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDE1NzU0OCJ9fQ==	no [IC50 >10 uM]
CYP2A6 911	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw1MjgyIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDE1NzU0OCJ9fQ==	no [IC50 >10 uM]
CYP2C19 2141	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNjIyIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDE1NzU0OCJ9fQ==	no [IC50 >10 uM]
CYP2C9 2497	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzMzk3IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDE1NzU0OCJ9fQ==	no [IC50 >10 uM]
CYP2D6 2546	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwyODkiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMMTU3NTQ4In19	no [IC50 >10 uM]
CYP2E1 1146	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw1MjgxIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDE1NzU0OCJ9fQ==	no [IC50 >10 uM]
CYP3A4 2633	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNDAiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMMTU3NTQ4In19	no [IC50 >10 uM]
CYP3A4 2633	inducer 1966 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/71335#section=BioAssay-Results Page: 137.0	no

Drug as victim

Target	Modality	Activity
BCRP 697	substrate 4014 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7138090/	yes
MRP2 252	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/17211460/	yes
P-gp 2052	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/17211460/	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwyNDAiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMMTU3NTQ4In19

PubMed

Title	Date	PubMed
Determination of the Mutant Selection Window and Evaluation of the Killing of Mycoplasma gallisepticum by Danofloxacin, Doxycycline, Tilmicosin, Tylvalosin and Valnemulin.	2017	28052123
Toxic effects of methylmercury, arsanilic acid and danofloxacin on the differentiation of mouse embryonic stem cells into neural cells.	2014	24136205
Effect of Danofloxacin on Reactive Oxygen Species Production, Lipid Peroxidation and Antioxidant Enzyme Activities in Kidney Tubular Epithelial Cell Line, LLC-PK1.	2013-12	23855763
Pharmacokinetics of danofloxacin after single dose intravenous, intramuscular and subcutaneous administration to loggerhead turtles Caretta caretta.	2008-12-22	19244975
Danofloxacin-mesylate is a substrate for ATP-dependent efflux transporters.	2007-02	17211460
Pharmacokinetic and pharmacodynamic profiles of danofloxacin administered by two dosing regimens in calves infected with Mannheimia (Pasteurella) haemolytica.	2002-09	12183261
Pharmacokinetics of enrofloxacin and danofloxacin in plasma, inflammatory exudate, and bronchial secretions of calves following subcutaneous administration.	1999-08	10428924

Patents

Sample Use Guides

In Vivo Use Guide

Administered by subcutaneous injection at either 8 mg per kilogram of body weight once or 6 mg per kilogram of body weight with treatment repeated once approximately 48 hours following the first injection.

Route of Administration: Other

In Vitro Use Guide

Danofloxacin minimum inhibitory concentration values (MIC90) were 0.06 ug/mL for both Mannheimia haemolytica and Pasteurella multocida.

Name

Type

Language

DANOFLOXACIN

Official Name

English

A180

Preferred Name

English

1-CYCLOPROPYL-6-FLUORO-1,4-DIHYDRO-7-((1S,4S)-5-METHYL-2,5-DIAZABICYCLO(2.2.1)HEPT-2-YL)-4-OXO-3-QUINOLINECARBOXYLIC ACID

Systematic Name

English

DANOFLOXACIN [GREEN BOOK]

Common Name

English

DANOFLOXACIN [MI]

Common Name

English

3-QUINOLINECARBOXYLIC ACID, 1-CYCLOPROPYL-6-FLUORO-1,4-DIHYDRO-7-(5-METHYL-2,5-DIAZABICYCLO(2.2.1)HEPT-2-YL)-4-OXO-, (1S)-

Common Name

English

danofloxacin [INN]

Common Name

English

ADVOCIN

Brand Name

English

Classification Tree Code System Code

CFR

21 CFR 556.169