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MedKoo Cat#: 528217 | Name: Trovirdine hydrochloride

Description:

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

Trovirdine hydrochloride, also known as LY-300046 and PETT-1, is a reverse transcriptase inhibitor potentially for the treatment of HIV infection. Trovirdine inhibited HIV-1 RT with an IC50 of 0.007 microM when employing heteropolymeric primer/template (oligo-DNA/ribosomal RNA) and dGTP as substrate. Enzyme kinetic studies showed that inhibition of RT by trovirdine was non-competitive with regard to deoxynucleoside triphosphates and uncompetitive with respect to varied primer/template under steady-state conditions. The amino acid changes Leu100, Tyr181 and Tyr188 gave rise to 25-, 147- and 12-fold decrease in inhibition by trovirdine.

Chemical Structure

Trovirdine hydrochloride
Trovirdine hydrochloride
CAS#148311-89-1 (HCl)

Theoretical Analysis

MedKoo Cat#: 528217

Name: Trovirdine hydrochloride

CAS#: 148311-89-1 (HCl)

Chemical Formula: C13H14BrClN4S

Exact Mass:

Molecular Weight: 373.70

Elemental Analysis: C, 41.78; H, 3.78; Br, 21.38; Cl, 9.49; N, 14.99; S, 8.58

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 #
148311-89-1 (HCl) 149488-17-5 (free)
Synonym
Trovirdine hydrochloride; LY-300046; LY 300046; LY300046; LY-300082; LY 300082; LY300082; PETT-1; PETT 1; PETT1
IUPAC/Chemical Name
1-(5-bromopyridin-2-yl)-3-(2-(pyridin-2-yl)ethyl)thiourea hydrochloride
InChi Key
IUQKLSJRANLIKE-UHFFFAOYSA-N
InChi Code
InChI=1S/C13H13BrN4S.ClH/c14-10-4-5-12(17-9-10)18-13(19)16-8-6-11-3-1-2-7-15-11;/h1-5,7,9H,6,8H2,(H2,16,17,18,19);1H
SMILES Code
S=C(NCCC1=NC=CC=C1)NC2=NC=C(Br)C=C2.[H]Cl
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 373.70 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: Gavriliu D, Fossey C, Ciurea A, Delbederi Z, Sugeac E, Ladurée D, Schmidt S, Laumond G, Aubertin AM. Synthesis and anti-HIV activity of [d4U]-[trovirdine analogue] and [d4T]-[trovirdine analogue] heterodimers as inhibitors of HIV-1 reverse transcriptase. Nucleosides Nucleotides Nucleic Acids. 2002;21(8-9):505-33. PubMed PMID: 12484448. 2: Sugeac E, Fossey C, Ladurée D, Schmidt S, Laumond G, Aubertin AM. Synthesis and anti-HIV activity of some heterodimers [NRTI]-glycyl-succinyl-[trovirdine analogue] of known HIV-1 reverse transcriptase inhibitors. J Enzyme Inhib Med Chem. 2003 Apr;18(2):175-86. PubMed PMID: 12943202. 3: Zhang H, Vrang L, Bäckbro K, Lind P, Sahlberg C, Unge T, Oberg B. Inhibition of human immunodeficiency virus type 1 wild-type and mutant reverse transcriptases by the phenyl ethyl thiazolyl thiourea derivatives trovirdine and MSC-127. Antiviral Res. 1995 Dec;28(4):331-42. PubMed PMID: 8669892. 4: Uckun FM, Mao C, Pendergrass S, Maher D, Zhu D, Tuel-Ahlgren L, Venkatachalam TK. N-[2-(1-cyclohexenyl)ethyl]-N'-[2-(5-bromopyridyl)]-thiourea and N'-[2-(1-cyclohexenyl)ethyl]-N'-[2-(5-chloropyridyl)]-thiourea as potent inhibitors of multidrug-resistant human immunodeficiency virus-1. Bioorg Med Chem Lett. 1999 Sep 20;9(18):2721-6. PubMed PMID: 10509923. 5: Mehanna AS, Belani JD, Kelley CJ, Pallansc LA. Design, synthesis and biological evaluation of a series of thioamides as non-nucleoside reverse transcriptase inhibitors. Med Chem. 2007 Nov;3(6):513-9. PubMed PMID: 18045200. 6: Ladurée D, Sugeac E, Fossey C, Schmidt S, Laumond G, Aubertin AM. Synthesis of certain heterodimers expected as HIV-1 reverse transcriptase inhibitors. Nucleosides Nucleotides Nucleic Acids. 2003 May-Aug;22(5-8):873-5. PubMed PMID: 14565300. 7: Uckun FM, Mao C, Pendergrass S, Maher D, Zhu D, Tuel-Ahlgren L, Venkatachalam TK. N-[2-(4-methylphenyl)ethyl]-N'-[2-(5-bromopyridyl)]-thiourea as a potent inhibitor of NNRTI-resistant and multidrug-resistant human immunodeficiency virus type 1. Antivir Chem Chemother. 2000 Mar;11(2):135-40. PubMed PMID: 10819437. 8: El-Essawy A, El-Sayed WA, El-Kafrawy SA, Morshedy AS, Abdel-Rahman AH. Anti-hepatitis B virus activity of new 1,2,4-triazol-2-yl- and 1,3,4-oxadiazol-2-yl-2-pyridinone derivatives. Z Naturforsch C. 2008 Sep-Oct;63(9-10):667-74. PubMed PMID: 19040105. 9: Uckun FM, Pendergrass S, Maher D, Zhu D, Tuel-Ahlgren L, Mao C, Venkatachalam TK. N'-[2-(2-thiophene)ethyl]-N'-[2-(5-bromopyridyl)] thiourea as a potent inhibitor of NNI-resistant and multidrug-resistant human immunodeficiency virus-1. Bioorg Med Chem Lett. 1999 Dec 20;9(24):3411-6. PubMed PMID: 10617082. 10: Mao C, Vig R, Venkatachalam TK, Sudbeck EA, Uckun FM. Structure-based design of N-[2-(1-piperidinylethyl)]-N'-[2-(5-bromopyridyl)]-thiourea and N-[2-(1-piperazinylethyl)]-N'-[2-(5-bromopyridyl)]-thiourea as potent non-nucleoside inhibitors of HIV-1 reverse transcriptase. Bioorg Med Chem Lett. 1998 Aug 18;8(16):2213-8. PubMed PMID: 9873515. 11: Venkatachalam TK, Sudbeck EA, Mao C, Uckun FM. Stereochemistry of halopyridyl and thiazolyl thiourea compounds is a major determinant of their potency as nonnucleoside inhibitors of HIV-1 reverse transcriptase. Bioorg Med Chem Lett. 2000 Sep 18;10(18):2071-4. PubMed PMID: 10999473. 12: Mao C, Sudbeck EA, Venkatachalam TK, Uckun FM. Rational design of N-[2-(2,5-dimethoxyphenylethyl)]-N'-[2-(5-bromopyridyl)]-thiourea (HI-236) as a potent non-nucleoside inhibitor of drug-resistant human immunodeficiency virus. Bioorg Med Chem Lett. 1999 Jun 7;9(11):1593-8. PubMed PMID: 10386942. 13: D'Cruz OJ, Uckun FM. Novel derivatives of phenethyl-5-bromopyridylthiourea and dihydroalkoxybenzyloxopyrimidine are dual-function spermicides with potent anti-human immunodeficiency virus activity. Biol Reprod. 1999 Jun;60(6):1419-28. PubMed PMID: 10330101. 14: Mao C, Sudbeck EA, Venkatachalam TK, Uckun FM. Structure-based design of non-nucleoside reverse transcriptase inhibitors of drug-resistant human immunodeficiency virus. Antivir Chem Chemother. 1999 Sep;10(5):233-40. PubMed PMID: 10574178. 15: Cantrell AS, Engelhardt P, Högberg M, Jaskunas SR, Johansson NG, Jordan CL, Kangasmetsä J, Kinnick MD, Lind P, Morin JM Jr, Muesing MA, Noreén R, Oberg B, Pranc P, Sahlberg C, Ternansky RJ, Vasileff RT, Vrang L, West SJ, Zhang H. Phenethylthiazolylthiourea (PETT) compounds as a new class of HIV-1 reverse transcriptase inhibitors. 2. Synthesis and further structure-activity relationship studies of PETT analogs. J Med Chem. 1996 Oct 11;39(21):4261-74. PubMed PMID: 8863804. 16: Vig R, Mao C, Venkatachalam TK, Tuel-Ahlgren L, Sudbeck EA, Uckun FM. Rational design and synthesis of phenethyl-5-bromopyridyl thiourea derivatives as potent non-nucleoside inhibitors of HIV reserve transcriptase. Bioorg Med Chem. 1998 Oct;6(10):1789-97. PubMed PMID: 9839009. 17: De Clercq E. Perspectives of non-nucleoside reverse transcriptase inhibitors (NNRTIs) in the therapy of HIV-1 infection. Farmaco. 1999 Jan-Feb;54(1-2):26-45. Review. PubMed PMID: 10321027. 18: Ahgren C, Backro K, Bell FW, Cantrell AS, Clemens M, Colacino JM, Deeter JB, Engelhardt JA, Hogberg M, Jaskunas SR, et al. The PETT series, a new class of potent nonnucleoside inhibitors of human immunodeficiency virus type 1 reverse transcriptase. Antimicrob Agents Chemother. 1995 Jun;39(6):1329-35. PubMed PMID: 7574525; PubMed Central PMCID: PMC162736. 19: Uberla K, Stahl-Hennig C, Böttiger D, Mätz-Rensing K, Kaup FJ, Li J, Haseltine WA, Fleckenstein B, Hunsmann G, Oberg B, et al. Animal model for the therapy of acquired immunodeficiency syndrome with reverse transcriptase inhibitors. Proc Natl Acad Sci U S A. 1995 Aug 29;92(18):8210-4. PubMed PMID: 7545297; PubMed Central PMCID: PMC41126.