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MedKoo Cat#: 326736 | Name: Ciluprevir

Description:

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

Ciluprevir, also known as BILN 2061, is a potent and selective HCV NS3 protease inhibitor with proven antiviral effect in humans. In vitro sensitivity studies with BILN 2061 showed a decrease in affinity for proteases of genotypes 2 and 3 (K(i), 80 to 90 nM) compared to genotype 1 enzymes (K(i), 1.5 nM). BILN 2061 may be an antiviral agent for individuals infected with non-genotype-1 HCV.

Chemical Structure

Ciluprevir
Ciluprevir
CAS#300832-84-2

Theoretical Analysis

MedKoo Cat#: 326736

Name: Ciluprevir

CAS#: 300832-84-2

Chemical Formula: C40H50N6O8S

Exact Mass: 774.3411

Molecular Weight: 774.93

Elemental Analysis: C, 62.00; H, 6.50; N, 10.85; O, 16.52; S, 4.14

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 #
No Data
Synonym
BILN 2061; BILN-2061; BILN2061; BILN-2061ZW; BILN2061ZW; BILN 2061ZW; Ciluprevir
IUPAC/Chemical Name
(2R,6S,13aS,14aR,16aS,Z)-6-(((cyclopentyloxy)carbonyl)amino)-2-((2-(2-(isopropylamino)thiazol-4-yl)-7-methoxyquinolin-4-yl)oxy)-5,16-dioxo-1,2,3,6,7,8,9,10,11,13a,14,15,16,16a-tetradecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a(5H)-carboxylic acid
InChi Key
PJZPDFUUXKKDNB-KNINVFKUSA-N
InChi Code
InChI=1S/C40H50N6O8S/c1-23(2)41-38-43-32(22-55-38)31-19-34(28-16-15-26(52-3)17-30(28)42-31)53-27-18-33-35(47)45-40(37(49)50)20-24(40)11-7-5-4-6-8-14-29(36(48)46(33)21-27)44-39(51)54-25-12-9-10-13-25/h7,11,15-17,19,22-25,27,29,33H,4-6,8-10,12-14,18,20-21H2,1-3H3,(H,41,43)(H,44,51)(H,45,47)(H,49,50)/b11-7-/t24-,27-,29+,33+,40-/m1/s1
SMILES Code
O=C([C@]([C@]1([H])/C=C\CCCCC[C@@H]2NC(OC3CCCC3)=O)(C1)NC([C@@](C[C@@H](OC4=CC(C5=CSC(NC(C)C)=N5)=NC6=CC(OC)=CC=C46)C7)([H])N7C2=O)=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
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 774.93 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: Busacca CA, Jones PJ, Campbell SJ, Saha AK, Gonnella NC, Senanayake CH. Probing the cation binding modes of macrocyclic HCV protease inhibitor BILN 2061 by multinuclear NMR. J Pharm Biomed Anal. 2012 Nov;70:609-13. doi: 10.1016/j.jpba.2012.06.013. Epub 2012 Jun 15. PubMed PMID: 22766359. 2: Stoltz JH, Stern JO, Huang Q, Seidler RW, Pack FD, Knight BL. A twenty-eight-day mechanistic time course study in the rhesus monkey with hepatitis C virus protease inhibitor BILN 2061. Toxicol Pathol. 2011 Apr;39(3):496-501. doi: 10.1177/0192623311398276. Epub 2011 Mar 25. PubMed PMID: 21441227. 3: Shu C, Zeng X, Hao MH, Wei X, Yee NK, Busacca CA, Han Z, Farina V, Senanayake CH. RCM macrocyclization made practical: an efficient synthesis of HCV protease inhibitor BILN 2061. Org Lett. 2008 Mar 20;10(6):1303-6. doi: 10.1021/ol800183x. Epub 2008 Feb 23. PubMed PMID: 18293994. 4: Vanwolleghem T, Meuleman P, Libbrecht L, Roskams T, De Vos R, Leroux-Roels G. Ultra-rapid cardiotoxicity of the hepatitis C virus protease inhibitor BILN 2061 in the urokinase-type plasminogen activator mouse. Gastroenterology. 2007 Oct;133(4):1144-55. Epub 2007 Jul 10. PubMed PMID: 17919490. 5: Yee NK, Farina V, Houpis IN, Haddad N, Frutos RP, Gallou F, Wang XJ, Wei X, Simpson RD, Feng X, Fuchs V, Xu Y, Tan J, Zhang L, Xu J, Smith-Keenan LL, Vitous J, Ridges MD, Spinelli EM, Johnson M, Donsbach K, Nicola T, Brenner M, Winter E, Kreye P, Samstag W. Efficient large-scale synthesis of BILN 2061, a potent HCV protease inhibitor, by a convergent approach based on ring-closing metathesis. J Org Chem. 2006 Sep 15;71(19):7133-45. PubMed PMID: 16958506. 6: Haddad N, Tan J, Farina V. Convergent synthesis of the quinolone substructure of BILN 2061 via carbonylative Sonogashira coupling/cyclization. J Org Chem. 2006 Jun 23;71(13):5031-4. PubMed PMID: 16776542. 7: Herrmann E, Zeuzem S, Sarrazin C, Hinrichsen H, Benhamou Y, Manns MP, Reiser M, Reesink H, Calleja JL, Forns X, Steinmann GG, Nehmiz G. Viral kinetics in patients with chronic hepatitis C treated with the serine protease inhibitor BILN 2061. Antivir Ther. 2006;11(3):371-6. PubMed PMID: 16759054. 8: Lin C, Gates CA, Rao BG, Brennan DL, Fulghum JR, Luong YP, Frantz JD, Lin K, Ma S, Wei YY, Perni RB, Kwong AD. In vitro studies of cross-resistance mutations against two hepatitis C virus serine protease inhibitors, VX-950 and BILN 2061. J Biol Chem. 2005 Nov 4;280(44):36784-91. Epub 2005 Aug 8. PubMed PMID: 16087668. 9: Reiser M, Hinrichsen H, Benhamou Y, Reesink HW, Wedemeyer H, Avendano C, Riba N, Yong CL, Nehmiz G, Steinmann GG. Antiviral efficacy of NS3-serine protease inhibitor BILN-2061 in patients with chronic genotype 2 and 3 hepatitis C. Hepatology. 2005 Apr;41(4):832-5. PubMed PMID: 15732092. 10: Hinrichsen H, Benhamou Y, Wedemeyer H, Reiser M, Sentjens RE, Calleja JL, Forns X, Erhardt A, Crönlein J, Chaves RL, Yong CL, Nehmiz G, Steinmann GG. Short-term antiviral efficacy of BILN 2061, a hepatitis C virus serine protease inhibitor, in hepatitis C genotype 1 patients. Gastroenterology. 2004 Nov;127(5):1347-55. PubMed PMID: 15521004. 11: Tsantrizos YS. The design of a potent inhibitor of the hepatitis C virus NS3 protease: BILN 2061--from the NMR tube to the clinic. Biopolymers. 2004;76(4):309-23. PubMed PMID: 15386268. 12: Faucher AM, Bailey MD, Beaulieu PL, Brochu C, Duceppe JS, Ferland JM, Ghiro E, Gorys V, Halmos T, Kawai SH, Poirier M, Simoneau B, Tsantrizos YS, Llinàs-Brunet M. Synthesis of BILN 2061, an HCV NS3 protease inhibitor with proven antiviral effect in humans. Org Lett. 2004 Aug 19;6(17):2901-4. PubMed PMID: 15330643. 13: Thibeault D, Bousquet C, Gingras R, Lagacé L, Maurice R, White PW, Lamarre D. Sensitivity of NS3 serine proteases from hepatitis C virus genotypes 2 and 3 to the inhibitor BILN 2061. J Virol. 2004 Jul;78(14):7352-9. PubMed PMID: 15220408; PubMed Central PMCID: PMC434094. 14: Llinàs-Brunet M, Bailey MD, Bolger G, Brochu C, Faucher AM, Ferland JM, Garneau M, Ghiro E, Gorys V, Grand-Maître C, Halmos T, Lapeyre-Paquette N, Liard F, Poirier M, Rhéaume M, Tsantrizos YS, Lamarre D. Structure-activity study on a novel series of macrocyclic inhibitors of the hepatitis C virus NS3 protease leading to the discovery of BILN 2061. J Med Chem. 2004 Mar 25;47(7):1605-8. PubMed PMID: 15027850. 15: Lin C, Lin K, Luong YP, Rao BG, Wei YY, Brennan DL, Fulghum JR, Hsiao HM, Ma S, Maxwell JP, Cottrell KM, Perni RB, Gates CA, Kwong AD. In vitro resistance studies of hepatitis C virus serine protease inhibitors, VX-950 and BILN 2061: structural analysis indicates different resistance mechanisms. J Biol Chem. 2004 Apr 23;279(17):17508-14. Epub 2004 Feb 6. PubMed PMID: 14766754.