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Tox21_300723

Tox21_300723

Synopsis, Chemistry

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Also known as: 173584-44-6, (s)-indoxacarb, Steward, Insecticide, Provaunt, Advion

Molecular Formula

C₂₂H₁₇ClF₃N₃O₇

Molecular Weight

527.8 g/mol

InChI Key

VBCVPMMZEGZULK-NRFANRHFSA-N

FDA UNII

52H0D26MWR

1 2D Structure

Tox21_300723

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

methyl (4aS)-7-chloro-2-[methoxycarbonyl-[4-(trifluoromethoxy)phenyl]carbamoyl]-3,5-dihydroindeno[1,2-e][1,3,4]oxadiazine-4a-carboxylate

2.1.2 InChI

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

2.1.3 InChI Key

VBCVPMMZEGZULK-NRFANRHFSA-N

2.1.4 Canonical SMILES

COC(=O)C12CC3=C(C1=NN(CO2)C(=O)N(C4=CC=C(C=C4)OC(F)(F)F)C(=O)OC)C=CC(=C3)Cl

2.1.5 Isomeric SMILES

COC(=O)[C@]12CC3=C(C1=NN(CO2)C(=O)N(C4=CC=C(C=C4)OC(F)(F)F)C(=O)OC)C=CC(=C3)Cl

2.2 Other Identifiers

2.2.1 UNII

52H0D26MWR

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Dpx-mp062

2.3.2 Depositor-Supplied Synonyms

1. 173584-44-6

2. (s)-indoxacarb

3. Steward

4. Insecticide

5. Provaunt

6. Advion

7. Avaunt

8. Indoxacarb [iso]

9. 52h0d26mwr

10. 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)-

11. Methyl (4as)-7-chloro-2-[methoxycarbonyl-[4-(trifluoromethoxy)phenyl]carbamoyl]-3,5-dihydroindeno[1,2-e][1,3,4]oxadiazine-4a-carboxylate

12. Chebi:38630

13. Indoxacarb (jan)

14. 174060-41-4

15. Methyl (4as)-7-chloro-2-{(methoxycarbonyl)[4-(trifluoromethoxy)phenyl]carbamoyl}-2,5-dihydroindeno[1,2-e][1,3,4]oxadiazine-4a(3h)-carboxylate

16. Avatar

17. Avent

18. Indoxacarb [jan]

19. (+/-)-indoxacarb;dpx-jw 062; Dpx-mp 062; Tornado; Tornado 10fl

20. Dpx-kn 128

21. Hsdb 7280

22. Dpx-mp 062-381

23. Unii-52h0d26mwr

24. Dpx-mp062

25. Indoxacarb 10 Microg/ml In Cyclohexane

26. (4as)-indoxacarb

27. Activyl

28. Indoxacarb [mi]

29. Indoxacarb [hsdb]

30. (+)-indoxacarb

31. Dsstox_cid_12690

32. Dsstox_rid_79034

33. Dsstox_gsid_32690

34. Indoxacarb, (+)-

35. Schembl22073

36. Dpx-kn128

37. Methyl (s)-7chloro-2,5-dihydro-2-(((methoxycarbonyl)(4-(trifluoromethoxy)phenyl)amino)carbonylindeno(1,2-e)(1,3,4)oxadiazine-4a(3h)-carboxylate

38. Chembl197676

39. Dtxsid1032690

40. Amy20519

41. Tox21_300723

42. Zinc28527855

43. Akos037643748

44. Ncgc00164264-02

45. Ncgc00164264-03

46. Ncgc00254629-01

47. As-35129

48. Indoxacarb (ema Epar: Veterinary)

49. Activyl Tick Plus Component Indoxacarb

50. Cas-173584-44-6

51. Indoxacarb, Pestanal(r), Analytical Standard

52. C18569

53. D06316

54. Indoxacarb Component Of Activyl Tick Plus

55. Q421469

56. (s)-methyl 7-chloro-2-(methoxycarbonyl(4-(trifluoromethoxy)phenyl)carbamoyl)-2,3,4a,5-tetrahydroindeno[1,2-e][1,3,4]oxadiazine-4a-carboxylate

57. Indeno[1,2-e][1,3,4]oxadiazine-4a(3h)-carboxylicacid,7-chloro-2,5-dihydro-2-[[(methoxycarbonyl)[4-(trifluoromethoxy)phenyl]amino]carbonyl]-,methyl Ester

58. 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

59. Pesticide3_indoxacarb_c22h17clf3n3o7_methyl (4as)-7-chloro-2-{(methoxycarbonyl)[4-(trifluoromethoxy)phenyl]carbamoyl}-2,5-dihydroindeno[1,2-e][1,3,4]oxadiazine-4a(3h)-carboxylate

2.4 Create Date

2005-08-08

3 Chemical and Physical Properties

Molecular Formula	C₂₂H₁₇ClF₃N₃O₇
Molecular Weight	527.8 g/mol
XLogP3	4.8
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	11
Rotatable Bond Count	5
Exact Mass	527.0707121 g/mol
Monoisotopic Mass	527.0707121 g/mol
Topological Polar Surface Area	107 Å²
Heavy Atom Count	36
Formal Charge	0
Complexity	912
Isotope Atom Count	0
Defined Atom Stereocenter Count	1
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

Treatment and prevention of flea infestation.

For dogs and cats: Treatment and prevention of flea infestation.

The veterinary medicinal product can be used as part of a treatment strategy for flea-allergy dermatitis. Developing stages of fleas in the pet's immediate surroundings are killed following contact with Activyl-treated pets.

5 Pharmacology and Biochemistry

5.1 ATC Code

QP53AX27

5.2 Metabolism/Metabolites

Metabolism in rats after oral dosing was studied using both DPX-JW062 and DPX-MP062. Most of the dose was excreted within 96 hr. Extensive metabolism to numerous minor metabolites occurs. In urine, metabolites were cleaved products (indane or trifluoromethoxyphenyl ring products), whilst in feces, major metabolites retained both these moieties. Major metabolic reactions included hydroxylation of the indane ring, hydrolysis of the carboxymethyl group from the amino nitrogen, and opening of the oxadiazine ring, which gave rise to cleaved products.

Tomlin CDS, ed. Indoxacarb (173584-44-6). In: The e-Pesticide Manual, 13th Edition Version 3.0 (2003-04). Surrey UK, British Crop Protection Council.

5.3 Mechanism of Action

... Indoxacarb inhibits sodium channels and certain subtypes of nicotinic receptors.

PMID:12370061 Narahashi T; Mini Rev Med Chem 2 (4): 419-32 (2002)

The effects of the oxadiazine insecticide indoxacarb and its N-decarbomethoxylated metabolite (DCJW) on tetrodotoxin-resistant (TTX-R) voltage-gated sodium channels in rat dorsal ganglion neurons were studied using the whole-cell patch clamp technique. Indoxacarb and DCJW suppressed the peak amplitude of action potentials, and DCJW exhibited a faster time course and higher potency than indoxacarb in the blocking effects. In voltage-clamp experiments, indoxacarb and DCJW suppressed TTX-R sodium currents in a time-dependent manner without a steady-state level of suppression. IC50 values for indoxacarb and DCJW on TTX-R sodium currents were estimated to be 10.7 and 0.8 microM after 25 min of bath application, respectively. DCJW was about 10 times more potent than indoxacarb in blocking TTX-R sodium currents. Although the suppressive effects of indoxacarb were partially reversible after washout with drug-free external solution, no recovery of sodium current was observed in DCJW treated neurons after prolonged washout. In current-voltage relationships, both indoxacarb and DCJW blocked the sodium currents to the same degree in the entire range of membrane potentials. The sodium conductance-voltage curve was not shifted along the voltage axis by indoxacarb and DCJW at 10 microM. In contrast, the steady-state inactivation curves were shifted in the hyperpolarizing direction by indoxacarb as well as by DCJW. Based on these results, it was concluded that indoxacarb and DCJW potently blocked the TTX-R sodium channel in rat DRG neurons with hyperpolarizing shifts of the steady-state inactivation curves, suggesting preferential association of the insecticides to the inactivated state of sodium channels. The small structural variation between indoxacarb and DCJW resulted in clear differences in potency for blocking sodium channels and reversibility after washout.

PMID:12974351 Tsurubuchi Y, Kono Y; Pest Manag Sci 59 (9): 999-1006 (2003)