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MedKoo Cat#: 529306 | Name: Triciribine phosphate

Description:

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

Triciribine phosphate is a protein kinase B (PKB/Akt) inhibitor potentially for the treatment of ovarian cancer, and breast cancer.

Chemical Structure

Triciribine phosphate
Triciribine phosphate
CAS#61966-08-3

Theoretical Analysis

MedKoo Cat#: 529306

Name: Triciribine phosphate

CAS#: 61966-08-3

Chemical Formula: C13H17N6O7P

Exact Mass: 400.0896

Molecular Weight: 400.28

Elemental Analysis: C, 39.01; H, 4.28; N, 21.00; O, 27.98; P, 7.74

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 #
35943-35-2 61966-08-3
Synonym
VQD-002; VQD 002; VQD002; PTX-200; PTX 200; PTX200; PTX-002; PTX002; PTX 002; NSC-280594; TCN-P; Triciribine phosphate;
IUPAC/Chemical Name
((2R,3S,4R,5R)-5-(3-amino-5-methyl-1,4,5,6,8-pentaazaacenaphthylen-1(5H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl dihydrogen phosphate
InChi Key
URLYINUFLXOMHP-HTVVRFAVSA-N
InChi Code
InChI=1S/C13H17N6O7P/c1-18-11-7-5(10(14)17-18)2-19(12(7)16-4-15-11)13-9(21)8(20)6(26-13)3-25-27(22,23)24/h2,4,6,8-9,13,20-21H,3H2,1H3,(H2,14,17)(H2,22,23,24)/t6-,8-,9-,13-/m1/s1
SMILES Code
NC1=NN(C)C2=C3C(N([C@H]4[C@@H]([C@@H]([C@@H](COP(O)(O)=O)O4)O)O)C=C13)=NC=N2
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 400.28 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: Garrett CR, Coppola D, Wenham RM, Cubitt CL, Neuger AM, Frost TJ, Lush RM, Sullivan DM, Cheng JQ, Sebti SM. Phase I pharmacokinetic and pharmacodynamic study of triciribine phosphate monohydrate, a small-molecule inhibitor of AKT phosphorylation, in adult subjects with solid tumors containing activated AKT. Invest New Drugs. 2011 Dec;29(6):1381-9. doi: 10.1007/s10637-010-9479-2. PubMed PMID: 20644979; PubMed Central PMCID: PMC4612514. 2: Kim R, Yamauchi T, Husain K, Sebti S, Malafa M. Triciribine Phosphate Monohydrate, an AKT Inhibitor, Enhances Gemcitabine Activity in Pancreatic Cancer Cells. Anticancer Res. 2015 Sep;35(9):4599-604. PubMed PMID: 26254348. 3: Sampath D, Malik A, Plunkett W, Nowak B, Williams B, Burton M, Verstovsek S, Faderl S, Garcia-Manero G, List AF, Sebti S, Kantarjian HM, Ravandi F, Lancet JE. Phase I clinical, pharmacokinetic, and pharmacodynamic study of the Akt-inhibitor triciribine phosphate monohydrate in patients with advanced hematologic malignancies. Leuk Res. 2013 Nov;37(11):1461-7. doi: 10.1016/j.leukres.2013.07.034. PubMed PMID: 23993427; PubMed Central PMCID: PMC4205589. 4: Moore EC, Hurlbert RB, Boss GR, Massia SP. Inhibition of two enzymes in de novo purine nucleotide synthesis by triciribine phosphate (TCN-P). Biochem Pharmacol. 1989 Nov 15;38(22):4045-51. PubMed PMID: 2480792. 5: Wotring LL, Crabtree GW, Edwards NL, Parks RE Jr, Townsend LB. Mechanism of activation of triciribine phosphate (TCN-P) as a prodrug form of TCN. Cancer Treat Rep. 1986 Apr;70(4):491-7. PubMed PMID: 3698043. 6: Padilla A, Amiable C, Pochet S, Kaminski PA, Labesse G. Structure of the oncoprotein Rcl bound to three nucleotide analogues. Acta Crystallogr D Biol Crystallogr. 2013 Feb;69(Pt 2):247-55. doi: 10.1107/S0907444912045039. PubMed PMID: 23385460. 7: Berndt N, Yang H, Trinczek B, Betzi S, Zhang Z, Wu B, Lawrence NJ, Pellecchia M, Schönbrunn E, Cheng JQ, Sebti SM. The Akt activation inhibitor TCN-P inhibits Akt phosphorylation by binding to the PH domain of Akt and blocking its recruitment to the plasma membrane. Cell Death Differ. 2010 Nov;17(11):1795-804. doi: 10.1038/cdd.2010.63. PubMed PMID: 20489726; PubMed Central PMCID: PMC2952662. 8: Gürsel DB, Connell-Albert YS, Tuskan RG, Anastassiadis T, Walrath JC, Hawes JJ, Amlin-Van Schaick JC, Reilly KM. Control of proliferation in astrocytoma cells by the receptor tyrosine kinase/PI3K/AKT signaling axis and the use of PI-103 and TCN as potential anti-astrocytoma therapies. Neuro Oncol. 2011 Jun;13(6):610-21. doi: 10.1093/neuonc/nor035. PubMed PMID: 21636709; PubMed Central PMCID: PMC3107099. 9: Shedden K, Townsend LB, Drach JC, Rosania GR. A rational approach to personalized anticancer therapy: chemoinformatic analysis reveals mechanistic gene-drug associations. Pharm Res. 2003 Jun;20(6):843-7. PubMed PMID: 12817886. 10: Tomillero A, Moral MA. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2009 Mar;31(2):107-46. PubMed PMID: 19455266. 11: Porcari AR, Ptak RG, Borysko KZ, Breitenbach JM, Drach JC, Townsend LB. Synthesis and antiviral activity of 2-substituted analogs of triciribine. Nucleosides Nucleotides Nucleic Acids. 2003 Dec;22(12):2171-93. PubMed PMID: 14714765. 12: Ptak RG, Borysko KZ, Porcari AR, Buthod JL, Holland LE, Shipman C Jr, Townsend LB, Drach JC. Phosphorylation of triciribine is necessary for activity against HIV type 1. AIDS Res Hum Retroviruses. 1998 Oct 10;14(15):1315-22. PubMed PMID: 9788672. 13: Feun LG, Blessing JA, Barrett RJ, Hanjani P. A phase II trial of tricyclic nucleoside phosphate in patients with advanced squamous cell carcinoma of the cervix. A Gynecologic Oncology Group Study. Am J Clin Oncol. 1993 Dec;16(6):506-8. PubMed PMID: 8256767. 14: Kucera LS, Iyer NP, Puckett SH, Buckheit RW Jr, Westbrook L, Toyer BR, White EL, Germany-Decker JM, Shannon WM, Chen RC, et al. Activity of triciribine and triciribine-5'-monophosphate against human immunodeficiency virus types 1 and 2. AIDS Res Hum Retroviruses. 1993 Apr;9(4):307-14. PubMed PMID: 7685612. 15: Townsend LB, Kawasaki AM, VanSickle AP, Wotring LL. The synthesis and biological activity of certain pentaazaacenaphthylenes, hexaazaacenaphthylenes and their corresponding nucleosides. Nucleic Acids Symp Ser. 1986;(17):41-4. PubMed PMID: 3562273. 16: Feun LG, Savaraj N, Bodey GP, Lu K, Yap BS, Ajani JA, Burgess MA, Benjamin RS, McKelvey E, Krakoff I. Phase I study of tricyclic nucleoside phosphate using a five-day continuous infusion schedule. Cancer Res. 1984 Aug;44(8):3608-12. PubMed PMID: 6744283. 17: Basseches PJ, Durski A, Powis G. High-performance liquid chromatographic assay of the antineoplastic agent tricyclic nucleoside 5'-phosphate and its disposition in rabbit. J Chromatogr. 1982 Dec 10;233:227-34. PubMed PMID: 7161335. 18: Schilcher RB, Haas CD, Samson MK, Young JD, Baker LH. Phase I evaluation and clinical pharmacology of tricyclic nucleoside 5'-phosphate using a weekly intravenous regimen. Cancer Res. 1986 Jun;46(6):3147-51. PubMed PMID: 3698029. 19: Powis G, Basseches PJ, Kroschel DM, Richardson RL, O'Connell MJ, Kvols LK. Disposition of tricyclic nucleoside-5'-monophosphate in blood and plasma of patients during phase I and II clinical trials. Cancer Treat Rep. 1986 Mar;70(3):359-62. PubMed PMID: 3955547. 20: Behrens BC, Hamilton TC, Louie KG, Grotzinger KR, McKoy WM, Tsuruo T, Young RC, Ozols RF. Activity of tricyclic nucleoside 5'-phosphate in model systems of human ovarian cancer. Invest New Drugs. 1986;4(4):295-304. PubMed PMID: 3583641.

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