Oteseconazole
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MedKoo CAT#: 319588

CAS#: 1340593-59-0

Description: 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

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Oteseconazole
CAS# 1340593-59-0

Theoretical Analysis

MedKoo Cat#: 319588
Name: Oteseconazole
CAS#: 1340593-59-0
Chemical Formula: C23H16F7N5O2
Exact Mass: 527.12
Molecular Weight: 527.403
Elemental Analysis: C, 52.38; H, 3.06; F, 25.22; N, 13.28; O, 6.07

Price and Availability

Size Price Availability Quantity
10mg USD 450 2 Weeks
25mg USD 750 2 Weeks
50mg USD 1250 2 Weeks
100mg USD 2250 2 Weeks
200mg USD 3850 2 Weeks
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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:
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/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 250.0 474.02

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.

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1: Gupta AK, Studholme C. Novel investigational therapies for onychomycosis: an update. Expert Opin Investig Drugs. 2016;25(3):297-305. doi: 10.1517/13543784.2016.1142529. Review. PubMed PMID: 26765142.

2: Hoekstra WJ, Hargrove TY, Wawrzak Z, da Gama Jaen Batista D, da Silva CF, Nefertiti AS, Rachakonda G, Schotzinger RJ, Villalta F, Soeiro Mde N, Lepesheva GI. Clinical Candidate VT-1161's Antiparasitic Effect In Vitro, Activity in a Murine Model of Chagas Disease, and Structural Characterization in Complex with the Target Enzyme CYP51 from Trypanosoma cruzi. Antimicrob Agents Chemother. 2015 Dec 7;60(2):1058-66. doi: 10.1128/AAC.02287-15. PubMed PMID: 26643331; PubMed Central PMCID: PMC4750653.

3: Gebremariam T, Wiederhold NP, Fothergill AW, Garvey EP, Hoekstra WJ, Schotzinger RJ, Patterson TF, Filler SG, Ibrahim AS. VT-1161 Protects Immunosuppressed Mice from Rhizopus arrhizus var. arrhizus Infection. Antimicrob Agents Chemother. 2015 Dec;59(12):7815-7. doi: 10.1128/AAC.01437-15. PubMed PMID: 26369977; PubMed Central PMCID: PMC4649228.

4: Shubitz LF, Trinh HT, Galgiani JN, Lewis ML, Fothergill AW, Wiederhold NP, Barker BM, Lewis ER, Doyle AL, Hoekstra WJ, Schotzinger RJ, Garvey EP. Evaluation of VT-1161 for Treatment of Coccidioidomycosis in Murine Infection Models. Antimicrob Agents Chemother. 2015 Dec;59(12):7249-54. doi: 10.1128/AAC.00593-15. PubMed PMID: 26369964; PubMed Central PMCID: PMC4649211.

5: Garvey EP, Hoekstra WJ, Schotzinger RJ, Sobel JD, Lilly EA, Fidel PL Jr. Efficacy of the clinical agent VT-1161 against fluconazole-sensitive and -resistant Candida albicans in a murine model of vaginal candidiasis. Antimicrob Agents Chemother. 2015 Sep;59(9):5567-73. doi: 10.1128/AAC.00185-15. PubMed PMID: 26124165; PubMed Central PMCID: PMC4538529.

6: 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. PubMed PMID: 25605358; PubMed Central PMCID: PMC4356789.

7: Moriyama B, Gordon LA, McCarthy M, Henning SA, Walsh TJ, Penzak SR. Emerging drugs and vaccines for candidemia. Mycoses. 2014 Dec;57(12):718-33. doi: 10.1111/myc.12265. Review. PubMed PMID: 25294098; PubMed Central PMCID: PMC4269330.

8: 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. PubMed PMID: 25224009; PubMed Central PMCID: PMC4249504.

9: Hoekstra WJ, Garvey EP, Moore WR, Rafferty SW, Yates CM, Schotzinger RJ. Design and optimization of highly-selective fungal CYP51 inhibitors. Bioorg Med Chem Lett. 2014 Aug 1;24(15):3455-8. doi: 10.1016/j.bmcl.2014.05.068. PubMed PMID: 24948565.

10: Walker K. Interscience Conference on Antimicrobial Agents and Chemotherapy - 50th Annual Meeting - Research on Promising New Agents: Part 2. IDrugs. 2010 Nov;13(11):746-8. PubMed PMID: 21046516.