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MedKoo Cat#: 319588 | Name: Oteseconazole
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Description:

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

Oteseconazole, also known as VT-1161, is a tetrazole antifungal agent potentially for the treatment of candidal vaginal infection. VT-1161 Protects Immunosuppressed Mice from Rhizopus arrhizus var. arrhizus Infection. VT-1161 dosed once daily or once weekly exhibits potent efficacy in treatment of dermatophytosis in a guinea pig model.

Chemical Structure

Oteseconazole
Oteseconazole
CAS#1340593-59-0

Theoretical Analysis

MedKoo Cat#: 319588

Name: Oteseconazole

CAS#: 1340593-59-0

Chemical Formula: C23H16F7N5O2

Exact Mass: 527.1192

Molecular Weight: 527.40

Elemental Analysis: C, 52.38; H, 3.06; F, 25.22; N, 13.28; O, 6.07

Price and Availability

Size Price Availability Quantity
1mg USD 75.00 Ready to ship
5mg USD 250.00 Ready to ship
10mg USD 450.00 Ready to ship
25mg USD 750.00 Ready to ship
50mg USD 1,250.00 Ready to ship
100mg USD 2,250.00 Ready to ship
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Related CAS #
No Data
Synonym
Oteseconazole; VT-1161; VT 1161; VT1161.
IUPAC/Chemical Name
(R)-2-(2,4-difluorophenyl)-1,1-difluoro-3-(1H-tetrazol-1-yl)-1-(5-(4-(2,2,2-trifluoroethoxy)phenyl)pyridin-2-yl)propan-2-ol
InChi Key
IDUYJRXRDSPPRC-NRFANRHFSA-N
InChi Code
InChI=1S/C23H16F7N5O2/c24-16-4-7-18(19(25)9-16)21(36,11-35-13-32-33-34-35)23(29,30)20-8-3-15(10-31-20)14-1-5-17(6-2-14)37-12-22(26,27)28/h1-10,13,36H,11-12H2/t21-/m0/s1
SMILES Code
FC(F)(COC1=CC=C(C=C1)C2=CN=C(C=C2)C(F)(F)[C@@](O)(C3=CC=C(C=C3F)F)CN4N=NN=C4)F
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, not in water
Shelf Life
>2 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
Product Data
Product Data
Certificate of Analysis
View CoA: current batch, Lot#S24S09C10
Safety Data Sheet (SDS)
View Safety Data Sheet (SDS)
Instruction
View handling instruction
Biological target:
Oteseconazole (VT-1161) is an orally active anti-fungal agent, potently binds to and inhibits Candida albicans CYP51 (Kd, <39 nM).
In vitro activity:
VT-1161 produced a type II binding spectrum with Candida albicans CYP51, characteristic of heme iron coordination. In reconstitution assays, VT-1161 inhibited Candida albicans CYP51 activity in a tight-binding fashion with a potency similar to that of the pharmaceutical azoles but failed to inhibit the human enzyme at the highest concentration tested (50 μM). In addition, VT-1161 (MIC = 0.002 μg ml(-1)) had a more pronounced fungal sterol disruption profile (increased levels of methylated sterols and decreased levels of ergosterol) than the known CYP51 inhibitor voriconazole (MIC = 0.004 μg ml(-1)). Reference: Antimicrob Agents Chemother. 2014 Dec;58(12):7121-7. https://pubmed.ncbi.nlm.nih.gov/25224009/
In vivo activity:
In pharmacokinetic studies supporting testing in a guinea pig model of dermatophytosis, VT-1161 plasma concentrations following single oral doses were dose proportional and persisted at or above the MIC values for at least 48 h, indicating potential in vivo efficacy with once-daily and possibly once-weekly dosing. Subsequently, in a guinea pig dermatophytosis model utilizing Trichophyton mentagrophytes and at oral doses of 5, 10, or 25 mg/kg of body weight once daily or 70 mg/kg once weekly, VT-1161 was statistically superior to untreated controls in fungal burden reduction (P < 0.001) and improvement in clinical scores (P < 0.001). Reference: Antimicrob Agents Chemother. 2015 Apr;59(4):1992-7. https://pubmed.ncbi.nlm.nih.gov/25605358/
Solvent mg/mL mM
Solubility
DMSO 250.0 474.02
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 527.40 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
Formulation protocol:
1. Break TJ, Desai JV, Natarajan M, Ferre EMN, Henderson C, Zelazny AM, Siebenlist U, Hoekstra WJ, Schotzinger RJ, Garvey EP, Lionakis MS. VT-1161 protects mice against oropharyngeal candidiasis caused by fluconazole-susceptible and -resistant Candida albicans. J Antimicrob Chemother. 2018 Jan 1;73(1):151-155. doi: 10.1093/jac/dkx352. PMID: 29040636; PMCID: PMC5890729. 2. Warrilow AG, Hull CM, Parker JE, Garvey EP, Hoekstra WJ, Moore WR, Schotzinger RJ, Kelly DE, Kelly SL. The clinical candidate VT-1161 is a highly potent inhibitor of Candida albicans CYP51 but fails to bind the human enzyme. Antimicrob Agents Chemother. 2014 Dec;58(12):7121-7. doi: 10.1128/AAC.03707-14. Epub 2014 Sep 15. PMID: 25224009; PMCID: PMC4249504. 3. Gebremariam T, Alkhazraji S, Lin L, Wiederhold NP, Garvey EP, Hoekstra WJ, Schotzinger RJ, Patterson TF, Filler SG, Ibrahim AS. Prophylactic Treatment with VT-1161 Protects Immunosuppressed Mice from Rhizopus arrhizus var. arrhizus Infection. Antimicrob Agents Chemother. 2017 Aug 24;61(9):e00390-17. doi: 10.1128/AAC.00390-17. PMID: 28652241; PMCID: PMC5571349. 4. Garvey EP, Hoekstra WJ, Moore WR, Schotzinger RJ, Long L, Ghannoum MA. VT-1161 dosed once daily or once weekly exhibits potent efficacy in treatment of dermatophytosis in a guinea pig model. Antimicrob Agents Chemother. 2015 Apr;59(4):1992-7. doi: 10.1128/AAC.04902-14. Epub 2015 Jan 20. PMID: 25605358; PMCID: PMC4356789.
In vitro protocol:
1. Break TJ, Desai JV, Natarajan M, Ferre EMN, Henderson C, Zelazny AM, Siebenlist U, Hoekstra WJ, Schotzinger RJ, Garvey EP, Lionakis MS. VT-1161 protects mice against oropharyngeal candidiasis caused by fluconazole-susceptible and -resistant Candida albicans. J Antimicrob Chemother. 2018 Jan 1;73(1):151-155. doi: 10.1093/jac/dkx352. PMID: 29040636; PMCID: PMC5890729. 2. Warrilow AG, Hull CM, Parker JE, Garvey EP, Hoekstra WJ, Moore WR, Schotzinger RJ, Kelly DE, Kelly SL. The clinical candidate VT-1161 is a highly potent inhibitor of Candida albicans CYP51 but fails to bind the human enzyme. Antimicrob Agents Chemother. 2014 Dec;58(12):7121-7. doi: 10.1128/AAC.03707-14. Epub 2014 Sep 15. PMID: 25224009; PMCID: PMC4249504.
In vivo protocol:
1. Gebremariam T, Alkhazraji S, Lin L, Wiederhold NP, Garvey EP, Hoekstra WJ, Schotzinger RJ, Patterson TF, Filler SG, Ibrahim AS. Prophylactic Treatment with VT-1161 Protects Immunosuppressed Mice from Rhizopus arrhizus var. arrhizus Infection. Antimicrob Agents Chemother. 2017 Aug 24;61(9):e00390-17. doi: 10.1128/AAC.00390-17. PMID: 28652241; PMCID: PMC5571349. 2. Garvey EP, Hoekstra WJ, Moore WR, Schotzinger RJ, Long L, Ghannoum MA. VT-1161 dosed once daily or once weekly exhibits potent efficacy in treatment of dermatophytosis in a guinea pig model. Antimicrob Agents Chemother. 2015 Apr;59(4):1992-7. doi: 10.1128/AAC.04902-14. Epub 2015 Jan 20. PMID: 25605358; PMCID: PMC4356789.
1: Sivasankar S, Boppe A, Grobusch MP, Jeyaraj S. Evaluation of MMV Pandemic Response Box compounds to identify potent compounds against clinically relevant bacterial and fungal clinical isolates in vitro. New Microbes New Infect. 2024 Jun 20;60-61:101444. doi: 10.1016/j.nmni.2024.101444. PMID: 39040124; PMCID: PMC11261442. 2: Gupta AK, Talukder M, Shemer A, Galili E. Safety and efficacy of new generation azole antifungals in the management of recalcitrant superficial fungal infections and onychomycosis. Expert Rev Anti Infect Ther. 2024 Jun;22(6):399-412. doi: 10.1080/14787210.2024.2362911. Epub 2024 Jun 12. PMID: 38841996. 3: Yu J, Wang Y, Ragueneau-Majlessi I. Risk of Enzyme- and Transporter-mediated Drug Interactions With Drugs Approved by the US Food and Drug Administration in 2022: A Detailed Analysis of In Vitro and Clinical Data Available in New Drug Application Reviews. Clin Ther. 2024 Jun;46(6):499-508. doi: 10.1016/j.clinthera.2024.04.008. Epub 2024 May 10. PMID: 38734524. 4: Kriegl L, Egger M, Boyer J, Hoenigl M, Krause R. New treatment options for critically important WHO fungal priority pathogens. Clin Microbiol Infect. 2024 Mar 9:S1198-743X(24)00118-6. doi: 10.1016/j.cmi.2024.03.006. Epub ahead of print. PMID: 38461942. 5: Herrick EJ, Patel P, Hashmi MF. Antifungal Ergosterol Synthesis Inhibitors. 2024 Mar 1. In: StatPearls [Internet]. Treasure Island (FL): StatPearls Publishing; 2024 Jan–. PMID: 31869062. 6: Hsu AJ, Hanisch BR, Fisher BT, Huppler AR. Pipeline of Novel Antifungals for Invasive Fungal Disease in Transplant Recipients: A Pediatric Perspective. J Pediatric Infect Dis Soc. 2024 Feb 28;13(Supplement_1):S68-S79. doi: 10.1093/jpids/piad115. PMID: 38417087. 7: Dey D, Kumar A. Unveiling the potential of recently FDA-approved drugs as quorum sensing inhibitors against P. Aeruginosa using high-performance computational techniques. J Biomol Struct Dyn. 2024 Jan 17:1-18. doi: 10.1080/07391102.2024.2304682. Epub ahead of print. PMID: 38230441. 8: Wang X, Chen L, Ruan H, Xiong Z, Wang W, Qiu J, Song W, Zhang C, Xue F, Qin T, Zhang B, An R, Luo X, Wang W, Zhang S, Cai Y, Kang J, Deng H, Fan S, Cui M, Wang S, Luo X, Su Z, Shu J, Wang Q, Wang F, Bai J, Liao Q. Oteseconazole versus fluconazole for the treatment of severe vulvovaginal candidiasis: a multicenter, randomized, double-blinded, phase 3 trial. Antimicrob Agents Chemother. 2024 Jan 10;68(1):e0077823. doi: 10.1128/aac.00778-23. Epub 2023 Dec 14. PMID: 38095426; PMCID: PMC10869335. 9: Siddiqui T, Kumar KA, Iqbal A, Doultani PR, Ashraf T, Eqbal F, Siddiqui SI. "Efficacy and safety of oteseconazole in recurrent vulvovaginal candidiasis (RVVC) - A systematic review and meta-analysis". Heliyon. 2023 Oct 20;9(11):e20495. doi: 10.1016/j.heliyon.2023.e20495. PMID: 37920530; PMCID: PMC10618760. 10: Lanier C, Melton TC. Oteseconazole for the Treatment of Recurrent Vulvovaginal Candidiasis: A Drug Review. Ann Pharmacother. 2024 Jun;58(6):636-644. doi: 10.1177/10600280231195649. Epub 2023 Aug 31. PMID: 37650387. 11: Satora M, Grunwald A, Zaremba B, Frankowska K, Żak K, Tarkowski R, Kułak K. Treatment of Vulvovaginal Candidiasis-An Overview of Guidelines and the Latest Treatment Methods. J Clin Med. 2023 Aug 18;12(16):5376. doi: 10.3390/jcm12165376. PMID: 37629418; PMCID: PMC10455317. 12: Friedman DZP, Schwartz IS. Emerging Diagnostics and Therapeutics for Invasive Fungal Infections. Infect Dis Clin North Am. 2023 Sep;37(3):593-616. doi: 10.1016/j.idc.2023.05.001. PMID: 37532392. 13: Ordaya EE, Clement J, Vergidis P. The Role of Novel Antifungals in the Management of Candidiasis: A Clinical Perspective. Mycopathologia. 2023 Dec;188(6):937-948. doi: 10.1007/s11046-023-00759-5. Epub 2023 Jul 20. PMID: 37470902; PMCID: PMC10687117. 14: Vandecruys P, Baldewijns S, Sillen M, Van Genechten W, Van Dijck P. Oteseconazole: a long-awaited diversification of the antifungal arsenal to manage recurrent vulvovaginal candidiasis (RVVC). Expert Rev Anti Infect Ther. 2023 Jul-Dec;21(8):799-812. doi: 10.1080/14787210.2023.2233696. Epub 2023 Jul 24. PMID: 37449774. 15: Koh XQ, Pan JY. Recalcitrant cutaneous fungal infections-A growing problem. Australas J Dermatol. 2023 Aug;64(3):315-321. doi: 10.1111/ajd.14115. Epub 2023 Jun 30. PMID: 37387447. 16: Gupta AK, Venkataraman M, Bamimore MA. Relative impact of traditional vs. newer oral antifungals for dermatophyte toenail onychomycosis: a network meta- analysis study. Br J Dermatol. 2023 Jul 7;189(1):12-22. doi: 10.1093/bjd/ljad070. PMID: 37253047. 17: Abuelizz HA, Bakheit AH, Al-Agamy MH, Rashid H, Mostafa GAE, Al-Salahi R. Benzo[g]quinazolines as antifungal against candidiasis: Screening, molecular docking, and QSAR investigations. Saudi Pharm J. 2023 Jun;31(6):815-823. doi: 10.1016/j.jsps.2023.04.012. Epub 2023 Apr 15. PMID: 37228321; PMCID: PMC10203769. 18: Lamoth F. Novel Therapeutic Approaches to Invasive Candidiasis: Considerations for the Clinician. Infect Drug Resist. 2023 Feb 22;16:1087-1097. doi: 10.2147/IDR.S375625. PMID: 36855391; PMCID: PMC9968438. 19: De SK. Oteseconazole: First Approved Orally Bioavailable and Selective CYP51 Inhibitor for the Treatment of Patients with Recurrent Vulvovaginal Candidiasis. Curr Med Chem. 2023;30(37):4170-4175. doi: 10.2174/0929867330666230220130024. PMID: 36803759. 20: Sobel JD. New Antifungals for Vulvovaginal Candidiasis: What Is Their Role? Clin Infect Dis. 2023 Mar 4;76(5):783-785. doi: 10.1093/cid/ciad002. PMID: 36610791.