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MedKoo Cat#: 326855 | Name: Tecovirimat

Description:

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

Tecovirimat, also known as ST-246 and SIGA-246, is a p37 envelope protein inhibitor for the treatment of smallpox infection. Tecovirimat is an antiviral with activity against orthopoxviruses such as smallpox and is currently undergoing clinical trials. It works by blocking cellular transmission of the virus, thus preventing the disease.

Chemical Structure

Tecovirimat
Tecovirimat
CAS#869572-92-9

Theoretical Analysis

MedKoo Cat#: 326855

Name: Tecovirimat

CAS#: 869572-92-9

Chemical Formula: C19H15F3N2O3

Exact Mass: 376.1035

Molecular Weight: 376.34

Elemental Analysis: C, 60.64; H, 4.02; F, 15.14; N, 7.44; O, 12.75

Price and Availability

This product was removed for the commercial reasons.
Related CAS #
1162664-19-8 (hydrate) 869572-92-9
Synonym
SIGA-246; SIGA246; SIGA 246; ST-246; ST 246; ST246; Tecovirimat; TPOXX.
IUPAC/Chemical Name
4-trifluoromethyl-N-(3,3a,4,4a,5,5a,6,6a-octahydro-1,3-dioxo-4,6-ethenocycloprop(f)isoindol-2(1H)-yl)-benzamide
InChi Key
CSKDFZIMJXRJGH-UHFFFAOYSA-N
InChi Code
InChI=1S/C19H15F3N2O3/c20-19(21,22)9-3-1-8(2-4-9)16(25)23-24-17(26)14-10-5-6-11(13-7-12(10)13)15(14)18(24)27/h1-6,10-15H,7H2,(H,23,25)
SMILES Code
O=C(NN(C(C1C2C(C3)C3C(C=C2)C41)=O)C4=O)C5=CC=C(C(F)(F)F)C=C5
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
>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

Preparing Stock Solutions

The following data is based on the product molecular weight 376.34 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: Russo AT, Berhanu A, Bigger CB, Prigge J, Silvera PM, Grosenbach DW, Hruby D. Co-administration of tecovirimat and ACAM2000™ in non-human primates: Effect of tecovirimat treatment on ACAM2000 immunogenicity and efficacy versus lethal monkeypox virus challenge. Vaccine. 2019 Oct 30. pii: S0264-410X(19)31429-X. doi: 10.1016/j.vaccine.2019.10.049. [Epub ahead of print] PubMed PMID: 31677948. 2: Lindholm DA, Fisher RD, Montgomery JR, Davidson W, Yu PA, Yu YC, Burgado J, Wilkins K, Petersen BW, Okulicz JF. Preemptive Tecovirimat Use in an Active Duty Service Member Who Presented With Acute Myeloid Leukemia After Smallpox Vaccination. Clin Infect Dis. 2019 Nov 27;69(12):2205-2207. doi: 10.1093/cid/ciz286. PubMed PMID: 30959520. 3: Chan-Tack KM, Harrington PR, Choi SY, Myers L, O'Rear J, Seo S, McMillan D, Ghantous H, Birnkrant D, Sherwat AI. Assessing a drug for an eradicated human disease: US Food and Drug Administration review of tecovirimat for the treatment of smallpox. Lancet Infect Dis. 2019 Jun;19(6):e221-e224. doi: 10.1016/S1473-3099(18)30788-6. Epub 2019 Mar 7. Review. PubMed PMID: 30853252. 4: Laudisoit A, Tepage F, Colebunders R. Oral Tecovirimat for the Treatment of Smallpox. N Engl J Med. 2018 Nov 22;379(21):2084-2085. doi: 10.1056/NEJMc1811044. PubMed PMID: 30462945. 5: Hoy SM. Tecovirimat: First Global Approval. Drugs. 2018 Sep;78(13):1377-1382. doi: 10.1007/s40265-018-0967-6. Review. PubMed PMID: 30120738. 6: Russo AT, Grosenbach DW, Brasel TL, Baker RO, Cawthon AG, Reynolds E, Bailey T, Kuehl PJ, Sugita V, Agans K, Hruby DE. Effects of Treatment Delay on Efficacy of Tecovirimat Following Lethal Aerosol Monkeypox Virus Challenge in Cynomolgus Macaques. J Infect Dis. 2018 Sep 22;218(9):1490-1499. doi: 10.1093/infdis/jiy326. PubMed PMID: 29982575; PubMed Central PMCID: PMC6151088. 7: Grosenbach DW, Honeychurch K, Rose EA, Chinsangaram J, Frimm A, Maiti B, Lovejoy C, Meara I, Long P, Hruby DE. Oral Tecovirimat for the Treatment of Smallpox. N Engl J Med. 2018 Jul 5;379(1):44-53. doi: 10.1056/NEJMoa1705688. PubMed PMID: 29972742; PubMed Central PMCID: PMC6086581. 8: Berhanu A, Prigge JT, Silvera PM, Honeychurch KM, Hruby DE, Grosenbach DW. Treatment with the smallpox antiviral tecovirimat (ST-246) alone or in combination with ACAM2000 vaccination is effective as a postsymptomatic therapy for monkeypox virus infection. Antimicrob Agents Chemother. 2015 Jul;59(7):4296-300. doi: 10.1128/AAC.00208-15. Epub 2015 Apr 20. PubMed PMID: 25896687; PubMed Central PMCID: PMC4468657. 9: Mucker EM, Goff AJ, Shamblin JD, Grosenbach DW, Damon IK, Mehal JM, Holman RC, Carroll D, Gallardo N, Olson VA, Clemmons CJ, Hudson P, Hruby DE. Efficacy of tecovirimat (ST-246) in nonhuman primates infected with variola virus (Smallpox). Antimicrob Agents Chemother. 2013 Dec;57(12):6246-53. doi: 10.1128/AAC.00977-13. Epub 2013 Oct 7. PubMed PMID: 24100494; PubMed Central PMCID: PMC3837858. 10: Bolken TC, Hruby DE. Tecovirimat for smallpox infections. Drugs Today (Barc). 2010 Feb;46(2):109-17. doi: 10.1358/dot.2010.46.2.1437244. PubMed PMID: 20393639. 11: Duraffour S, Andrei G, Snoeck R. Tecovirimat, a p37 envelope protein inhibitor for the treatment of smallpox infection. IDrugs. 2010 Mar;13(3):181-91. Review. PubMed PMID: 20191435. 12: Molecule of the month. Tecovirimat. Drug News Perspect. 2008 Nov;21(9):517. PubMed PMID: 19180269.