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MedKoo Cat#: 565731 | Name: Esafoxolaner

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Esafoxolaner is the S-isomer of Afoxolaner. (INN) is an insecticide and acaricide used in dogs. It is indicated for the treatment and prevention of flea infestations, and the treatment and control of tick infestations in dogs and puppies 8 weeks of age and older, weighing 4 pounds (~1.8 kilograms) of body weight or greater. It is given once a month.

Chemical Structure

Esafoxolaner
Esafoxolaner
CAS#1096103-99-9 (Esafoxolaner)

Theoretical Analysis

MedKoo Cat#: 565731

Name: Esafoxolaner

CAS#: 1096103-99-9 (Esafoxolaner)

Chemical Formula: C26H17ClF9N3O3

Exact Mass: 625.0815

Molecular Weight: 625.88

Elemental Analysis: C, 49.90; H, 2.74; Cl, 5.66; F, 27.32; N, 6.71; O, 7.67

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
1093861-60-9 (Afoxolaner) 1096103-99-9 (Esafoxolaner)
Synonym
Afoxolaner, Nexgard. S)-Afoxolaner; Esafoxolaner;
IUPAC/Chemical Name
S4-[5-[3-Chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-3-yl]-N-[2-oxo-2-(2,2,2-trifluoroethylamino)ethyl]naphthalene-1-carboxamide
InChi Key
OXDDDHGGRFRLEE-QHCPKHFHSA-N
InChi Code
InChI=1S/C26H17ClF9N3O3/c27-15-8-13(7-14(9-15)25(31,32)33)23(26(34,35)36)10-20(39-42-23)18-5-6-19(17-4-2-1-3-16(17)18)22(41)37-11-21(40)38-12-24(28,29)30/h1-9H,10-12H2,(H,37,41)(H,38,40)/t23-/m0/s1
SMILES Code
O=C(C1=C2C=CC=CC2=C(C3=NO[C@](C(F)(F)F)(C4=CC(C(F)(F)F)=CC(Cl)=C4)C3)C=C1)NCC(NCC(F)(F)F)=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 625.88 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Drag M, Saik J, Harriman J, Letendre L, Yoon S, Larsen D. Safety evaluation of orally administered afoxolaner and milbemycin oxime in eight-week-old dogs. J Vet Pharmacol Ther. 2017 Oct;40(5):447-453. doi: 10.1111/jvp.12375. Epub 2016 Nov 27. PubMed PMID: 27891622. 2: Letendre L, Harriman J, Drag M, Mullins A, Malinski T, Rehbein S. The intravenous and oral pharmacokinetics of afoxolaner and milbemycin oxime when used as a combination chewable parasiticide for dogs. J Vet Pharmacol Ther. 2017 Jan;40(1):35-43. doi: 10.1111/jvp.12332. Epub 2016 Sep 7. PubMed PMID: 27604405. 3: Carithers D, Crawford J, de Vos C, Lotriet A, Fourie J. Assessment of afoxolaner efficacy against Otodectes cynotis infestations of dogs. Parasit Vectors. 2016 Dec 9;9(1):635. PubMed PMID: 27938395; PubMed Central PMCID: PMC5148825. 4: Zewe CM, Altet L, Lam ATH, Ferrer L. Afoxolaner and fluralaner treatment do not impact on cutaneous Demodex populations of healthy dogs. Vet Dermatol. 2017 Oct;28(5):468-e107. doi: 10.1111/vde.12453. Epub 2017 May 23. PubMed PMID: 28544307. 5: Beugnet F, Halos L, Larsen D, de Vos C. Efficacy of oral afoxolaner for the treatment of canine generalised demodicosis. Parasite. 2016;23:14. doi: 10.1051/parasite/2016014. Epub 2016 Mar 24. PubMed PMID: 27012161; PubMed Central PMCID: PMC4807374. 6: Fankhauser R, Hamel D, Dorr P, Reinemeyer CR, Crafford D, Bowman DD, Ulrich M, Yoon S, Larsen DL. Efficacy of oral afoxolaner plus milbemycin oxime chewables against induced gastrointestinal nematode infections in dogs. Vet Parasitol. 2016 Jul 30;225:117-22. doi: 10.1016/j.vetpar.2016.06.003. Epub 2016 Jun 3. PubMed PMID: 27369586. 7: Packianathan R, Hodge A, Bruellke N, Davis K, Maeder S. Comparative speed of kill of sarolaner (Simparica(®)) and afoxolaner (NexGard(®)) against induced infestations of Ixodes holocyclus on dogs. Parasit Vectors. 2017 Feb 21;10(1):98. doi: 10.1186/s13071-017-2024-9. PubMed PMID: 28222813; PubMed Central PMCID: PMC5320688. 8: Tielemans E, Lebon W, Dumont P, Taweethavonsawat P, Larsen D, Rehbein S. Efficacy of afoxolaner plus milbemycin oxime chewable tablets (NexGard Spectra(®), Merial) against adult Ancylostoma ceylanicum hookworm, in dogs. Vet Parasitol. 2017 Apr 30;238:87-89. doi: 10.1016/j.vetpar.2017.03.028. Epub 2017 Apr 1. PubMed PMID: 28408213. 9: Cvejić D, Schneider C, Neethling W, Hellmann K, Liebenberg J, Navarro C. The sustained speed of kill of ticks (Rhipicephalus sanguineus) and fleas (Ctenocephalides felis felis) on dogs by a spot-on combination of fipronil and permethrin (Effitix(®)) compared with oral afoxolaner (NexGard(®)). Vet Parasitol. 2017 Aug 30;243:52-57. doi: 10.1016/j.vetpar.2017.06.011. Epub 2017 Jun 10. PubMed PMID: 28807310. 10: Rehbein S, Dorr P, Bowman DD, Crafford D, Kusi I, Postoli R, Yoon S, Chester ST, Dollhofer D, Visser M, Larsen DL. Efficacy of afoxolaner plus milbemycin oxime chewable tablets against naturally acquired intestinal nematodes in dogs. Vet Parasitol. 2016 Feb 15;217:29-35. doi: 10.1016/j.vetpar.2015.12.032. Epub 2016 Jan 2. PubMed PMID: 26827857. 11: Machado MA, Campos DR, Lopes NL, Barbieri Bastos IP, Botelho CB, Correia TR, Scott FB, Fernandes JI. Efficacy of afoxolaner in the treatment of otodectic mange in naturally infested cats. Vet Parasitol. 2018 May 30;256:29-31. doi: 10.1016/j.vetpar.2018.04.013. Epub 2018 Apr 27. PubMed PMID: 29887026. 12: Drag M, Saik J, Harriman J, Larsen D. Safety evaluation of orally administered afoxolaner in 8-week-old dogs. Vet Parasitol. 2014 Apr 2;201(3-4):198-203. doi: 10.1016/j.vetpar.2014.02.022. Epub 2014 Mar 13. PubMed PMID: 24629431. 13: Liebenberg J, Fourie J, Lebon W, Larsen D, Halos L, Beugnet F. Assessment of the insecticidal activity of afoxolaner against Aedes aegypti in dogs treated with NexGard(®). Parasite. 2017;24:39. doi: 10.1051/parasite/2017042. Epub 2017 Oct 23. PubMed PMID: 29063828; PubMed Central PMCID: PMC5654328. 14: Shoop WL, Hartline EJ, Gould BR, Waddell ME, McDowell RG, Kinney JB, Lahm GP, Long JK, Xu M, Wagerle T, Jones GS, Dietrich RF, Cordova D, Schroeder ME, Rhoades DF, Benner EA, Confalone PN. Discovery and mode of action of afoxolaner, a new isoxazoline parasiticide for dogs. Vet Parasitol. 2014 Apr 2;201(3-4):179-89. doi: 10.1016/j.vetpar.2014.02.020. Epub 2014 Mar 14. PubMed PMID: 24631502. 15: Dryden MW, Canfield MS, Kalosy K, Smith A, Crevoiserat L, McGrady JC, Foley KM, Green K, Tebaldi C, Smith V, Bennett T, Heaney K, Math L, Royal C, Sun F. Evaluation of fluralaner and afoxolaner treatments to control flea populations, reduce pruritus and minimize dermatologic lesions in naturally infested dogs in private residences in west central Florida USA. Parasit Vectors. 2016 Jun 28;9(1):365. doi: 10.1186/s13071-016-1654-7. PubMed PMID: 27352607; PubMed Central PMCID: PMC4924230. 16: Padivitage N, Kumar S, Rustum A. Development and Validation of a Reversed-Phase Chiral HPLC Method to Determine the Chiral Purity of Bulk Batches of (S)-Enantiomer in Afoxolaner. J AOAC Int. 2017 Jan 1;100(1):65-73. doi: 10.5740/jaoacint.16-0096. Epub 2016 Oct 13. PubMed PMID: 27743445. 17: Letendre L, Huang R, Kvaternick V, Harriman J, Drag M, Soll M. The intravenous and oral pharmacokinetics of afoxolaner used as a monthly chewable antiparasitic for dogs. Vet Parasitol. 2014 Apr 2;201(3-4):190-7. doi: 10.1016/j.vetpar.2014.02.021. Epub 2014 Mar 29. PubMed PMID: 24685320. 18: Otranto D. NEXGARD®. Afoxolaner, a new oral insecticide-acaricide to control fleas and ticks in dogs. Editorial. Vet Parasitol. 2014 Apr 2;201(3-4):177-8. doi: 10.1016/j.vetpar.2014.02.029. Epub 2014 Mar 12. PubMed PMID: 24629430. 19: Six RH, Young DR, Myers MR, Mahabir SP. Comparative speed of kill of sarolaner (Simparica) and afoxolaner (NexGard against induced infestations of Ixodes scapularis on dogs. Parasit Vectors. 2016 Feb 15;9:79. doi: 10.1186/s13071-016-1307-x. PubMed PMID: 26876891; PubMed Central PMCID: PMC4753652. 20: Zhuang J, Kumar S, Rustum A. Development and Validation of a Normal Phase Chiral HPLC Method for Analysis of Afoxolaner Using a Chiralpak® AD-3 Column. J Chromatogr Sci. 2016 Nov;54(10):1813-1819. Epub 2016 Oct 7. PubMed PMID: 27908928.