Presatovir | GS-5806 | CAS#1353625-73-6

MedKoo Cat#: 319648 | Name: Presatovir

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Description:

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

Presatovir, aslo known as GS-5806, is a potent and orally active antiviral fusion inhibitor, and is potential useful for the treatment of respiratory syncytial virus (RSV) infections. GS-5806 Inhibits a Broad Range of Respiratory Syncytial Virus Clinical Isolates by Blocking the Virus-Cell Fusion Process. GS-5806 inhibits pre- to postfusion conformational changes of the respiratory syncytial virus fusion protein.

Chemical Structure

Presatovir

CAS#1353625-73-6

Theoretical Analysis

MedKoo Cat#: 319648

Name: Presatovir

CAS#: 1353625-73-6

Chemical Formula: C24H30ClN7O3S

Exact Mass: 531.1819

Molecular Weight: 532.06

Elemental Analysis: C, 54.18; H, 5.68; Cl, 6.66; N, 18.43; O, 9.02; S, 6.03

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 800.00	2 Weeks

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Synonym

GS-5806; GS5806; GS 5806; Presatovir

IUPAC/Chemical Name

N-(2-((S)-2-(5-((S)-3-aminopyrrolidin-1-yl)-6-methylpyrazolo[1,5-a]pyrimidin-2-yl)piperidine-1-carbonyl)-4-chlorophenyl)methanesulfonamide

InChi Key

GOFXWTVKPWJNGD-UWJYYQICSA-N

InChi Code

InChI=1S/C24H30ClN7O3S/c1-15-13-32-22(27-23(15)30-10-8-17(26)14-30)12-20(28-32)21-5-3-4-9-31(21)24(33)18-11-16(25)6-7-19(18)29-36(2,34)35/h6-7,11-13,17,21,29H,3-5,8-10,14,26H2,1-2H3/t17-,21-/m0/s1

SMILES Code

CS(=O)(NC1=CC=C(Cl)C=C1C(N2[C@H](C3=NN4C=C(C)C(N5C[C@@H](N)CC5)=NC4=C3)CCCC2)=O)=O

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

Product Data

Instruction

View handling instruction

Biological target:

Presatovir (GS-5806) is an orally bioavailable RSV fusion inhibitor with a mean EC50 value of 0.43 nM.

In vitro activity:

GS-5806, discovered via chemical optimization of a hit from a high-throughput antiviral-screening campaign, selectively inhibits a diverse set of 75 RSV subtype A and B clinical isolates (mean 50% effective concentration [EC50] = 0.43 nM). In summary, GS-5806 is a potent and selective RSV fusion inhibitor with antiviral activity against a diverse set of RSV clinical isolates. Reference: Antimicrob Agents Chemother. 2015 Dec 14;60(3):1264-73. https://pubmed.ncbi.nlm.nih.gov/26666922/

In vivo activity:

TBD

Preparing Stock Solutions

The following data is based on the product molecular weight 532.06 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.

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. Perron M, Stray K, Kinkade A, Theodore D, Lee G, Eisenberg E, Sangi M, Gilbert BE, Jordan R, Piedra PA, Toms GL, Mackman R, Cihlar T. GS-5806 Inhibits a Broad Range of Respiratory Syncytial Virus Clinical Isolates by Blocking the Virus-Cell Fusion Process. Antimicrob Agents Chemother. 2015 Dec 14;60(3):1264-73. doi: 10.1128/AAC.01497-15. PMID: 26666922; PMCID: PMC4776015. 2. Samuel D, Xing W, Niedziela-Majka A, Wong JS, Hung M, Brendza KM, Perron M, Jordan R, Sperandio D, Liu X, Mackman R, Sakowicz R. GS-5806 inhibits pre- to postfusion conformational changes of the respiratory syncytial virus fusion protein. Antimicrob Agents Chemother. 2015 Nov;59(11):7109-12. doi: 10.1128/AAC.00761-15. Epub 2015 Aug 31. PMID: 26324264; PMCID: PMC4604407.

In vitro protocol:

In vivo protocol:

TBD

1: Gottlieb J, Torres F, Haddad T, Dhillon G, Dilling DF, Knoop C, Rampolla R, Walia R, Ahya V, Kessler R, Budev M, Neurohr C, Glanville AR, Jordan R, Porter D, McKevitt M, German P, Guo Y, Chien JW, Watkins TR, Zamora MR. A randomized controlled trial of presatovir for respiratory syncytial virus after lung transplant. J Heart Lung Transplant. 2023 Jul;42(7):908-916. doi: 10.1016/j.healun.2023.01.013. Epub 2023 Feb 7. PMID: 36964084. 2: Behera SK, Mahapatra N, Tripathy CS, Pati S. Drug repurposing for identification of potential inhibitors against SARS-CoV-2 spike receptor-binding domain: An in silico approach. Indian J Med Res. 2021 Jan & Feb;153(1 & 2):132-143. doi: 10.4103/ijmr.IJMR_1132_20. PMID: 33818470; PMCID: PMC8184087. 3: Yamaguchi-Sasaki T, Tamura Y, Ogata Y, Kawaguchi T, Kurosaka J, Sugaya Y, Iwakiri K, Busujima T, Takahashi R, Ueda-Yonemoto N, Tanigawa E, Abe-Kumasaka T, Sugiyama H, Kanuma K. Design and Synthesis of 2-(1-Alkylaminoalkyl)pyrazolo[1,5-a]pyrimidines as New Respiratory Syncytial Virus Fusion Protein Inhibitors. Chem Pharm Bull (Tokyo). 2020;68(4):345-362. doi: 10.1248/cpb.c19-00895. PMID: 32238652. 4: Porter DP, Guo Y, Perry J, Gossage DL, Watkins TR, Chien JW, Jordan R. Assessment of Drug Resistance during Phase 2b Clinical Trials of Presatovir in Adults Naturally Infected with Respiratory Syncytial Virus. Antimicrob Agents Chemother. 2020 Aug 20;64(9):e02312-19. doi: 10.1128/AAC.02312-19. PMID: 32071058; PMCID: PMC7449164. 5: Stray K, Perron M, Porter DP, Anderson F, Lewis SA, Perry J, Miller M, Cihlar T, DeVincenzo J, Chien JW, Jordan R. Drug Resistance Assessment Following Administration of Respiratory Syncytial Virus (RSV) Fusion Inhibitor Presatovir to Participants Experimentally Infected With RSV. J Infect Dis. 2020 Oct 1;222(9):1468-1477. doi: 10.1093/infdis/jiaa028. PMID: 31971597. 6: Marty FM, Chemaly RF, Mullane KM, Lee DG, Hirsch HH, Small CB, Bergeron A, Shoham S, Ljungman P, Waghmare A, Blanchard E, Kim YJ, McKevitt M, Porter DP, Jordan R, Guo Y, German P, Boeckh M, Watkins TR, Chien JW, Dadwal SS. A Phase 2b, Randomized, Double-blind, Placebo-Controlled Multicenter Study Evaluating Antiviral Effects, Pharmacokinetics, Safety, and Tolerability of Presatovir in Hematopoietic Cell Transplant Recipients with Respiratory Syncytial Virus Infection of the Lower Respiratory Tract. Clin Infect Dis. 2020 Dec 31;71(11):2787-2795. doi: 10.1093/cid/ciz1167. PMID: 31915807; PMCID: PMC7108198. 7: Chemaly RF, Dadwal SS, Bergeron A, Ljungman P, Kim YJ, Cheng GS, Pipavath SN, Limaye AP, Blanchard E, Winston DJ, Stiff PJ, Zuckerman T, Lachance S, Rahav G, Small CB, Mullane KM, Patron RL, Lee DG, Hirsch HH, Waghmare A, McKevitt M, Jordan R, Guo Y, German P, Porter DP, Gossage DL, Watkins TR, Marty FM, Chien JW, Boeckh M. A Phase 2, Randomized, Double-blind, Placebo-Controlled Trial of Presatovir for the Treatment of Respiratory Syncytial Virus Upper Respiratory Tract Infection in Hematopoietic-Cell Transplant Recipients. Clin Infect Dis. 2020 Dec 31;71(11):2777-2786. doi: 10.1093/cid/ciz1166. PMID: 31793991; PMCID: PMC7108134. 8: Beigel JH, Nam HH, Adams PL, Krafft A, Ince WL, El-Kamary SS, Sims AC. Advances in respiratory virus therapeutics - A meeting report from the 6th isirv Antiviral Group conference. Antiviral Res. 2019 Jul;167:45-67. doi: 10.1016/j.antiviral.2019.04.006. Epub 2019 Apr 8. PMID: 30974127; PMCID: PMC7132446. 9: German P, Xin Y, Chien JW, Weng W, Mackman R, Lewis SA, Meng A, Ling J, Mathias A. Phase 1 First-in-Human, Single- and Multiple-Ascending Dose, and Food Effect Studies to Assess the Safety, Tolerability, and Pharmacokinetics of Presatovir for the Treatment of Respiratory Syncytial Virus Infection. J Clin Pharmacol. 2018 Aug;58(8):1025-1034. doi: 10.1002/jcph.1112. Epub 2018 Apr 17. PMID: 29663420. 10: Xin Y, Weng W, Murray BP, Eisenberg EJ, Chien JW, Ling J, Silverman JA. The Drug-Drug Interaction Profile of Presatovir. J Clin Pharmacol. 2018 Jun;58(6):771-780. doi: 10.1002/jcph.1073. Epub 2018 Feb 7. PMID: 29412463. 11: Perron M, Stray K, Kinkade A, Theodore D, Lee G, Eisenberg E, Sangi M, Gilbert BE, Jordan R, Piedra PA, Toms GL, Mackman R, Cihlar T. GS-5806 Inhibits a Broad Range of Respiratory Syncytial Virus Clinical Isolates by Blocking the Virus-Cell Fusion Process. Antimicrob Agents Chemother. 2015 Dec 14;60(3):1264-73. doi: 10.1128/AAC.01497-15. PMID: 26666922; PMCID: PMC4776015. 12: Samuel D, Xing W, Niedziela-Majka A, Wong JS, Hung M, Brendza KM, Perron M, Jordan R, Sperandio D, Liu X, Mackman R, Sakowicz R. GS-5806 inhibits pre- to postfusion conformational changes of the respiratory syncytial virus fusion protein. Antimicrob Agents Chemother. 2015 Nov;59(11):7109-12. doi: 10.1128/AAC.00761-15. Epub 2015 Aug 31. PMID: 26324264; PMCID: PMC4604407. 13: Jordan R, Shao M, Mackman RL, Perron M, Cihlar T, Lewis SA, Eisenberg EJ, Carey A, Strickley RG, Chien JW, Anderson ML, McEligot HA, Behrens NE, Gershwin LJ. Antiviral Efficacy of a Respiratory Syncytial Virus (RSV) Fusion Inhibitor in a Bovine Model of RSV Infection. Antimicrob Agents Chemother. 2015 Aug;59(8):4889-900. doi: 10.1128/AAC.00487-15. Epub 2015 Jun 8. PMID: 26055364; PMCID: PMC4505261. 14: De Clercq E. Chemotherapy of respiratory syncytial virus infections: the final breakthrough. Int J Antimicrob Agents. 2015 Mar;45(3):234-7. doi: 10.1016/j.ijantimicag.2014.12.025. Epub 2015 Feb 2. PMID: 25684638. 15: Mackman RL, Sangi M, Sperandio D, Parrish JP, Eisenberg E, Perron M, Hui H, Zhang L, Siegel D, Yang H, Saunders O, Boojamra C, Lee G, Samuel D, Babaoglu K, Carey A, Gilbert BE, Piedra PA, Strickley R, Iwata Q, Hayes J, Stray K, Kinkade A, Theodore D, Jordan R, Desai M, Cihlar T. Discovery of an oral respiratory syncytial virus (RSV) fusion inhibitor (GS-5806) and clinical proof of concept in a human RSV challenge study. J Med Chem. 2015 Feb 26;58(4):1630-43. doi: 10.1021/jm5017768. Epub 2015 Jan 27. PMID: 25574686. 16: Wright PF. Progress in the prevention and treatment of RSV infection. N Engl J Med. 2014 Aug 21;371(8):776-7. doi: 10.1056/NEJMe1407467. PMID: 25140965. 17: DeVincenzo JP, Whitley RJ, Mackman RL, Scaglioni-Weinlich C, Harrison L, Farrell E, McBride S, Lambkin-Williams R, Jordan R, Xin Y, Ramanathan S, O'Riordan T, Lewis SA, Li X, Toback SL, Lin SL, Chien JW. Oral GS-5806 activity in a respiratory syncytial virus challenge study. N Engl J Med. 2014 Aug 21;371(8):711-22. doi: 10.1056/NEJMoa1401184. PMID: 25140957.