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Details

Stereochemistry ABSOLUTE
Molecular Formula C22H17ClF3N3O7
Molecular Weight 527.834
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of INDOXACARB

SMILES

COC(=O)N(C(=O)N1CO[C@]2(CC3=CC(Cl)=CC=C3C2=N1)C(=O)OC)C4=CC=C(OC(F)(F)F)C=C4

InChI

InChIKey=VBCVPMMZEGZULK-NRFANRHFSA-N
InChI=1S/C22H17ClF3N3O7/c1-33-18(30)21-10-12-9-13(23)3-8-16(12)17(21)27-28(11-35-21)19(31)29(20(32)34-2)14-4-6-15(7-5-14)36-22(24,25)26/h3-9H,10-11H2,1-2H3/t21-/m0/s1

HIDE SMILES / InChI

Description
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/11159709 | http://www.inchem.org/documents/jmpr/jmpmono/v2005pr13.pdf | http://us.activyl.com/ | http://www.dupont.co.za/products-and-services/crop-protection/fruit-farming/products/steward-wg-indoxacarb-insecticide.html

Indoxacarb is a new oxadiazine insecticide discovered and developed by DuPont. The indoxacarb racemate contains two enantiomers (S : R), designated DPX-KN128 and DPX-KN127, but only the S enantiomer has insecticidal activity. It inhibits insect neuronal voltage-dependent sodium channels. Indoxacarb is an active component of Merck Activyl® used in the treatment of flea and tick in dogs and cats. DuPont™ Steward® WG is a water dispersible granule stomach and contact insecticide powered by Indoxacarb for control of various insect pests on a variety of crops.

CNS Activity

CNS Penetrant
2554
Curator's Comment: Indoxacarb accumulates in the rat brain. No human data available.

Originator

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
 28.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Approved
8429
ACTIVYL

Approved Use

Activyl (indoxacarb as an active component) is a spot-on flea treatment for dogs and cats.

Launch Date

2011
PubMed

PubMed

TitleDatePubMed
The discovery of indoxacarb: oxadiazines as a new class of pyrazoline-type insecticides.
2001 Feb
Indoxacarb, an oxadiazine insecticide, blocks insect neuronal sodium channels.
2001 Jan
Environmental impact on vascular development predicted by high-throughput screening.
2011 Nov
Patents

Patents

JP2011506567A
10
JP2012500824A
79

Sample Use Guides

In Vivo Use Guide
Activyl is a spot-on flea treatment for dogs and cats. Active Ingredients Activyl contains 195 mg of indoxacarb and 354 mg of isopropyl alcohol per mL. DOGS: The recommended dose for dogs is 15 - 66 mg indoxacarb/kg bodyweight, equivalent to 0.077 - 0.34 mL/kg bodyweight. CATS: The recommended dose for cats is 25 - 166.6 mg indoxacarb/kg bodyweight, equivalent to 0.128 - 0.85 mL/kg bodyweight.
Route of Administration: Topical
In Vitro Use Guide
Parasite eggs, Ascaris suum eggs were incubated with 5% indoxacarb at 20℃ for 6 weeks, and microscopically evaluated the egg survival and development on a weekly basis.
Name Type Language
INDOXACARB
HSDB   ISO   JAN   MI  
Common Name English
METHYL (4AS)-7-CHLORO-2,5-DIHYDRO-2-(((METHOXYCARBONYL)(4-(TRIFLUOROMETHOXY)PHENYL)AMINO)CARBONYL)INDENO(1,2-E)(1,3,4)OXADIAZINE-4A(3H)-CARBOXYLATE
Common Name English
INDOXACARB [JAN]
Common Name English
STEWARD
Brand Name English
INDOXACARB [ISO]
Common Name English
ADVION
Brand Name English
INDOXACARB [HSDB]
Common Name English
INDOXACARB, (+)-
Common Name English
ACTIVYL
Brand Name English
INDENO(1,2-E)(1,3,4)OXADIAZINE-4A(3H)-CARBOXYLIC ACID, 7-CHLORO-2,5-DIHYDRO-2-(((METHOXYCARBONYL)(4-(TRIFLUOROMETHOXY)PHENYL)AMINO)CARBONYL)-, METHYL ESTER, (4AS)-
Systematic Name English
ACTIVYL TICK PLUS COMPONENT INDOXACARB
Common Name English
INDOXACARB (EMA EPAR: VETERINARY)
Common Name English
PROVAUNT
Brand Name English
INDOXACARB COMPONENT OF ACTIVYL TICK PLUS
Common Name English
DPX-KN128
Code English
INDOXACARB [MI]
Common Name English
(+)-INDOXACARB
Common Name English
AVAUNT
Brand Name English
Classification Tree Code System Code
EMA VETERINARY ASSESSMENT REPORTS ACTIVYL (AUTHORIZED)
Created by admin on Fri Dec 15 18:22:11 GMT 2023 , Edited by admin on Fri Dec 15 18:22:11 GMT 2023
EPA PESTICIDE CODE 67710
Created by admin on Fri Dec 15 18:22:11 GMT 2023 , Edited by admin on Fri Dec 15 18:22:11 GMT 2023
EMA VETERINARY ASSESSMENT REPORTS ACTIVYL TICK PLUS (AUTHORIZED)
Created by admin on Fri Dec 15 18:22:11 GMT 2023 , Edited by admin on Fri Dec 15 18:22:11 GMT 2023
WHO-VATC QP53AX27
Created by admin on Fri Dec 15 18:22:11 GMT 2023 , Edited by admin on Fri Dec 15 18:22:11 GMT 2023
EMA VETERINARY ASSESSMENT REPORTS ACTIVYL (AUTHORIZED)
Created by admin on Fri Dec 15 18:22:11 GMT 2023 , Edited by admin on Fri Dec 15 18:22:11 GMT 2023
Code System Code Type Description
CAS
173584-44-6
Created by admin on Fri Dec 15 18:22:11 GMT 2023 , Edited by admin on Fri Dec 15 18:22:11 GMT 2023
PRIMARY
SMS_ID
300000023782
Created by admin on Fri Dec 15 18:22:11 GMT 2023 , Edited by admin on Fri Dec 15 18:22:11 GMT 2023
PRIMARY
EPA CompTox
DTXSID1032690
Created by admin on Fri Dec 15 18:22:11 GMT 2023 , Edited by admin on Fri Dec 15 18:22:11 GMT 2023
PRIMARY
CHEBI
38630
Created by admin on Fri Dec 15 18:22:11 GMT 2023 , Edited by admin on Fri Dec 15 18:22:11 GMT 2023
PRIMARY
WIKIPEDIA
INDOXACARB
Created by admin on Fri Dec 15 18:22:11 GMT 2023 , Edited by admin on Fri Dec 15 18:22:11 GMT 2023
PRIMARY
ALANWOOD
indoxacarb
Created by admin on Fri Dec 15 18:22:11 GMT 2023 , Edited by admin on Fri Dec 15 18:22:11 GMT 2023
PRIMARY
MESH
C401104
Created by admin on Fri Dec 15 18:22:11 GMT 2023 , Edited by admin on Fri Dec 15 18:22:11 GMT 2023
PRIMARY
FDA UNII
52H0D26MWR
Created by admin on Fri Dec 15 18:22:11 GMT 2023 , Edited by admin on Fri Dec 15 18:22:11 GMT 2023
PRIMARY
PUBCHEM
107720
Created by admin on Fri Dec 15 18:22:11 GMT 2023 , Edited by admin on Fri Dec 15 18:22:11 GMT 2023
PRIMARY
MERCK INDEX
m6282
Created by admin on Fri Dec 15 18:22:11 GMT 2023 , Edited by admin on Fri Dec 15 18:22:11 GMT 2023
PRIMARY Merck Index
HSDB
7280
Created by admin on Fri Dec 15 18:22:11 GMT 2023 , Edited by admin on Fri Dec 15 18:22:11 GMT 2023
PRIMARY
ACTIVE MOIETY
Structure of INDOXACARB
NIH
NCATS
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