MedKoo Biosciences, Inc.
Tel:   +1-919-636-5577    Fax:   +1-919-980-4831    Email:   sales@medkoo.com
Search
Login Register
Search
MedKoo Cat#: 573304 | Name: Atevirdine free base
Featured New

Description:

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

Atevirdine, also known as U-87201, is a non-nucleoside reverse transcriptase inhibitor that has been studied for the treatment of HIV. Atevirdine has been shown to have significant anti-HIV RT activity in vitro, it inhibits HIV-1 replication in infected peripheral blood leukocyte cultures at a 50% inhibitory concentration of 1 nM and a concentration which is cytotoxic to 50% of cells of 100 μM and also inhibits completely the formation of syncytia in human T-cell leukemia virus type III-infected MT-2 cells at 2 μM.

Chemical Structure

Atevirdine free base
Atevirdine free base
CAS#136816-75-6 (free base)

Theoretical Analysis

MedKoo Cat#: 573304

Name: Atevirdine free base

CAS#: 136816-75-6 (free base)

Chemical Formula: C21H25N5O2

Exact Mass: 379.2008

Molecular Weight: 379.46

Elemental Analysis: C, 66.47; H, 6.64; N, 18.46; O, 8.43

Price and Availability

Size Price Availability Quantity
25mg USD 250.00 2 Weeks
50mg USD 450.00 2 Weeks
100mg USD 750.00 2 Weeks
200mg USD 1,350.00 2 Weeks
1g USD 3,950.00 2 Weeks
Bulk Inquiry
Buy Now
Add to Cart
Related CAS #
136816-75-6 (free base) 136816-66-5 (HCl) 138540-32-6 (mesylate)
Synonym
Atevirdine; U-87201E; U 87201E U87201E; U 87201; U-87201; U87201;
IUPAC/Chemical Name
Piperazine, 1-(3-(ethylamino)-2-pyridinyl)-4-((5-methoxy-1H-indol-2-yl)carbonyl)-
InChi Key
UCPOMLWZWRTIAA-UHFFFAOYSA-N
InChi Code
1S/C21H25N5O2/c1-3-22-18-5-4-8-23-20(18)25-9-11-26(12-10-25)21(27)19-14-15-13-16(28-2)6-7-17(15)24-19/h4-8,13-14,22,24H,3,9-12H2,1-2H3
SMILES Code
CCNc1cccnc1N2CCN(CC2)C(=O)c3cc4cc(OC)ccc4[nH]3
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 379.46 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: Galal SA, Abd El-All AS, Abdallah MM, El-Diwani HI. Synthesis of potent antitumor and antiviral benzofuran derivatives. Bioorg Med Chem Lett. 2009 May 1;19(9):2420-8. doi: 10.1016/j.bmcl.2009.03.069. Epub 2009 Mar 21. PMID: 19345581. 2: Morse GD, Reichman RC, Fischl MA, Para M, Leedom J, Powderly W, Demeter LM, Resnick L, Bassiakos Y, Timpone J, Cox S, Batts D. Concentration-targeted phase I trials of atevirdine mesylate in patients with HIV infection: dosage requirements and pharmacokinetic studies. The ACTG 187 and 199 study teams. Antiviral Res. 2000 Jan;45(1):47-58. doi: 10.1016/s0166-3542(99)00073-x. PMID: 10774589. 3: Demeter LM, Meehan PM, Morse G, Fischl MA, Para M, Powderly W, Leedom J, Holden-Wiltse J, Greisberger C, Wood K, Timpone J Jr, Wathen LK, Nevin T, Resnick L, Batts DH, Reichman RC. Phase I study of atevirdine mesylate (U-87201E) monotherapy in HIV-1-infected patients. J Acquir Immune Defic Syndr Hum Retrovirol. 1998 Oct 1;19(2):135-44. doi: 10.1097/00042560-199810010-00006. PMID: 9768622. 4: Chang M, Sood VK, Wilson GJ, Kloosterman DA, Sanders PE, Schuette MR, Judy RW, Voorman RL, Maio SM, Slatter JG. Absorption, distribution, metabolism, and excretion of atevirdine in the rat. Drug Metab Dispos. 1998 Oct;26(10):1008-18. PMID: 9763407. 5: Szeto ER, Freund J, Brew BJ, Loder A, Griffiths MR. Cerebral perfusion scanning in treating AIDS dementia: a pilot study. J Nucl Med. 1998 Feb;39(2):298-302. PMID: 9476939. 6: Been-Tiktak AM, de Haas CJ, de Graaf L, Boucher CA, Verhoef J, Borleffs JC, Nottet HS, Schuurman R. In-vitro selection of HIV-1 variants resistant to non- nucleoside reverse transcriptase inhibitors in monocyte-derived macrophages. J Antimicrob Chemother. 1997 Dec;40(6):847-53. doi: 10.1093/jac/40.6.847. PMID: 9462437. 7: Howard GM, Schwende FJ. Sensitive reversed-phase high-performance liquid chromatographic method for the determination of atevirdine and its N-desethyl metabolite in human saliva or cerebrospinal fluid using solid-phase extraction. J Chromatogr B Biomed Sci Appl. 1997 Jun 6;693(2):431-6. doi: 10.1016/s0378-4347(97)00090-x. PMID: 9210449. 8: Been-Tiktak AM, Williams I, Vrehen HM, Richens J, Aldam D, van Loon AM, Loveday C, Boucher CA, Ward P, Weller IV, Borleffs JC. Safety, tolerance, and efficacy of atevirdine in asymptomatic human immunodeficiency virus-infected individuals. Antimicrob Agents Chemother. 1996 Nov;40(11):2664-8. doi: 10.1128/AAC.40.11.2664. PMID: 8913487; PMCID: PMC163598. 9: Brew BJ, Dunbar N, Druett JA, Freund J, Ward P. Pilot study of the efficacy of atevirdine in the treatment of AIDS dementia complex. AIDS. 1996 Oct;10(12):1357-60. doi: 10.1097/00002030-199610000-00007. PMID: 8902064. 10: Romero DL, Olmsted RA, Poel TJ, Morge RA, Biles C, Keiser BJ, Kopta LA, Friis JM, Hosley JD, Stefanski KJ, Wishka DG, Evans DB, Morris J, Stehle RG, Sharma SK, Yagi Y, Voorman RL, Adams WJ, Tarpley WG, Thomas RC. Targeting delavirdine/atevirdine resistant HIV-1: identification of (alkylamino)piperidine-containing bis(heteroaryl)piperazines as broad spectrum HIV-1 reverse transcriptase inhibitors. J Med Chem. 1996 Sep 13;39(19):3769-89. doi: 10.1021/jm960158n. PMID: 8809165. 11: Morse GD, Fischl MA, Shelton MJ, Borin MT, Driver MR, DeRemer M, Lee K, Wajszczuk CP. Didanosine reduces atevirdine absorption in subjects with human immunodeficiency virus infections. Antimicrob Agents Chemother. 1996 Mar;40(3):767-71. doi: 10.1128/AAC.40.3.767. PMID: 8851608; PMCID: PMC163195. 12: Been-Tiktak AM, Vrehen HM, Schneider MM, van der Feltz M, Branger T, Ward P, Cox SR, Harry JD, Borleffs JC. Safety, tolerance, and pharmacokinetics of atevirdine mesylate (U-87201E) in asymptomatic human immunodeficiency virus- infected patients. Antimicrob Agents Chemother. 1995 Mar;39(3):602-7. doi: 10.1128/AAC.39.3.602. PMID: 7793859; PMCID: PMC162591. 13: Reichman RC, Morse GD, Demeter LM, Resnick L, Bassiakos Y, Fischl M, Para M, Powderly W, Leedom J, Greisberger C, et al. Phase I study of atevirdine, a nonnucleoside reverse transcriptase inhibitor, in combination with zidovudine for human immunodeficiency virus type 1 infection. ACTG 199 Study Team. J Infect Dis. 1995 Feb;171(2):297-304. doi: 10.1093/infdis/171.2.297. PMID: 7531207. 14: Roberts S, Bawdon R, Sobhi S, Dax J, Gilstrap L 3rd, Wimberly D. The maternal-fetal transfer of bisheteroypiperazine (U-87201-E) in the ex vivo human placenta. Am J Obstet Gynecol. 1995 Jan;172(1 Pt 1):88-91. doi: 10.1016/0002-9378(95)90089-6. PMID: 7531400. 15: Rosser LM, O'Donnell AM, Lee KM, Morse GD. In vitro protein-binding characteristics of atevirdine and its N-dealkylated metabolite. Antiviral Res. 1994 Dec;25(3-4):193-200. doi: 10.1016/0166-3542(94)90003-5. PMID: 7535991. 16: Romero DL, Morge RA, Biles C, Berrios-Pena N, May PD, Palmer JR, Johnson PD, Smith HW, Busso M, Tan CK, et al. Discovery, synthesis, and bioactivity of bis(heteroaryl)piperazines. 1. A novel class of non-nucleoside HIV-1 reverse transcriptase inhibitors. J Med Chem. 1994 Apr 1;37(7):999-1014. doi: 10.1021/jm00033a018. PMID: 7512142. 17: Nottet HS, Oteman MH, Visser MR, Verhoef J. Anti-human immunodeficiency virus type 1 activities of novel non-nucleoside reverse transcriptase inhibitors. J Antimicrob Chemother. 1994 Feb;33(2):366-8. doi: 10.1093/jac/33.2.366. PMID: 7514164. 18: Campbell TB, Young RK, Eron JJ, D'Aquila RT, Tarpley WG, Kuritzkes DR. Inhibition of human immunodeficiency virus type 1 replication in vitro by the bisheteroarylpiperazine atevirdine (U-87201E) in combination with zidovudine or didanosine. J Infect Dis. 1993 Aug;168(2):318-26. doi: 10.1093/infdis/168.2.318. PMID: 7687641. 19: Dueweke TJ, Pushkarskaya T, Poppe SM, Swaney SM, Zhao JQ, Chen IS, Stevenson M, Tarpley WG. A mutation in reverse transcriptase of bis(heteroaryl)piperazine- resistant human immunodeficiency virus type 1 that confers increased sensitivity to other nonnucleoside inhibitors. Proc Natl Acad Sci U S A. 1993 May 15;90(10):4713-7. doi: 10.1073/pnas.90.10.4713. PMID: 7685109; PMCID: PMC46583. 20: Althaus IW, Chou JJ, Gonzales AJ, Deibel MR, Chou KC, Kezdy FJ, Romero DL, Aristoff PA, Tarpley WG, Reusser F. Steady-state kinetic studies with the non- nucleoside HIV-1 reverse transcriptase inhibitor U-87201E. J Biol Chem. 1993 Mar 25;268(9):6119-24. PMID: 7681060.