MedKoo Biosciences, Inc.
Tel:   +1-919-636-5577    Fax:   +1-919-980-4831    Email:   sales@medkoo.com
Search
Login Register
Search
MedKoo Cat#: 581656 | Name: Alisporivir

Description:

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

Alisporivir is non-immunosuppressive cyclosporin that is a potent inhibitor of hepatitis C virus replication in vitro.

Chemical Structure

Alisporivir
Alisporivir
CAS#254435-95-5

Theoretical Analysis

MedKoo Cat#: 581656

Name: Alisporivir

CAS#: 254435-95-5

Chemical Formula: C63H113N11O12

Exact Mass: 1215.8570

Molecular Weight: 1216.66

Elemental Analysis: C, 62.19; H, 9.36; N, 12.66; O, 15.78

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.
Bulk Inquiry
Related CAS #
No Data
Synonym
Alisporivir; Debio 025; UNII-VBP9099AA6; UNIL 025; DEB025.
IUPAC/Chemical Name
(3S,6S,9S,12R,15S,18S,21S,24S,27R,30S,33S)-25,30-diethyl-33-((1R,2R,E)-1-hydroxy-2-methylhex-4-en-1-yl)-6,9,18-triisobutyl-3,21,24-triisopropyl-1,4,7,10,12,15,19,27,28-nonamethyl-1,4,7,10,13,16,19,22,25,28,31-undecaazacyclotritriacontan-2,5,8,11,14,17,20,23,26,29,32-undecaone
InChi Key
OLROWHGDTNFZBH-XEMWPYQTSA-N
InChi Code
InChI=1S/C63H113N11O12/c1-26-29-30-40(16)52(75)51-56(79)66-44(27-2)59(82)68(20)43(19)58(81)74(28-3)49(38(12)13)55(78)67-48(37(10)11)62(85)69(21)45(31-34(4)5)54(77)64-41(17)53(76)65-42(18)57(80)70(22)46(32-35(6)7)60(83)71(23)47(33-36(8)9)61(84)72(24)50(39(14)15)63(86)73(51)25/h26,29,34-52,75H,27-28,30-33H2,1-25H3,(H,64,77)(H,65,76)(H,66,79)(H,67,78)/b29-26+/t40-,41+,42-,43-,44+,45+,46+,47+,48+,49+,50+,51+,52-/m1/s1
SMILES Code
CC[C@H]1C(=O)N([C@@H](C(=O)N([C@H](C(=O)N[C@H](C(=O)N([C@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N([C@H](C(=O)N([C@H](C(=O)N([C@H](C(=O)N([C@H](C(=O)N1)[C@@H]([C@H](C)C/C=C/C)O)C)C(C)C)C)CC(C)C)C)CC(C)C)C)C)C)CC(C)C)C)C(C)C)C(C)C)CC)C)C
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
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 1,216.66 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: Dujardin M, Bouckaert J, Rucktooa P, Hanoulle X. X-ray structure of alisporivir in complex with cyclophilin A at 1.5 Å resolution. Acta Crystallogr F Struct Biol Commun. 2018 Sep 1;74(Pt 9):583-592. doi: 10.1107/S2053230X18010415. Epub 2018 Sep 3. PubMed PMID: 30198892. 2: de Wilde AH, Pham U, Posthuma CC, Snijder EJ. Cyclophilins and cyclophilin inhibitors in nidovirus replication. Virology. 2018 Sep;522:46-55. doi: 10.1016/j.virol.2018.06.011. Epub 2018 Jul 12. Review. PubMed PMID: 30014857. 3: Nevers Q, Ruiz I, Ahnou N, Donati F, Brillet R, Softic L, Chazal M, Jouvenet N, Fourati S, Baudesson C, Bruscella P, Gelin M, Guichou JF, Pawlotsky JM, Ahmed-Belkacem A. Characterization of the Anti-Hepatitis C Virus Activity of New Nonpeptidic Small-Molecule Cyclophilin Inhibitors with the Potential for Broad Anti-Flaviviridae Activity. Antimicrob Agents Chemother. 2018 Jun 26;62(7). pii: e00126-18. doi: 10.1128/AAC.00126-18. Print 2018 Jul. PubMed PMID: 29760125; PubMed Central PMCID: PMC6021681. 4: Schiavone M, Zulian A, Menazza S, Petronilli V, Argenton F, Merlini L, Sabatelli P, Bernardi P. Alisporivir rescues defective mitochondrial respiration in Duchenne muscular dystrophy. Pharmacol Res. 2017 Nov;125(Pt B):122-131. doi: 10.1016/j.phrs.2017.09.001. Epub 2017 Sep 9. PubMed PMID: 28899790. 5: de Wilde AH, Falzarano D, Zevenhoven-Dobbe JC, Beugeling C, Fett C, Martellaro C, Posthuma CC, Feldmann H, Perlman S, Snijder EJ. Alisporivir inhibits MERS- and SARS-coronavirus replication in cell culture, but not SARS-coronavirus infection in a mouse model. Virus Res. 2017 Jan 15;228:7-13. doi: 10.1016/j.virusres.2016.11.011. Epub 2016 Nov 10. PubMed PMID: 27840112. 6: Chiramel AI, Banadyga L, Dougherty JD, Falzarano D, Martellaro C, Brees D, Taylor RT, Ebihara H, Best SM. Alisporivir Has Limited Antiviral Effects Against Ebola Virus Strains Makona and Mayinga. J Infect Dis. 2016 Oct 15;214(suppl 3):S355-S359. Epub 2016 Aug 10. PubMed PMID: 27511894; PubMed Central PMCID: PMC5050471. 7: Chatterji U, Bobardt M, Schaffer L, Wood M, Gallay PA. Cyclophilin Inhibitors Remodel the Endoplasmic Reticulum of HCV-Infected Cells in a Unique Pattern Rendering Cells Impervious to a Reinfection. PLoS One. 2016 Jul 21;11(7):e0159511. doi: 10.1371/journal.pone.0159511. eCollection 2016. PubMed PMID: 27442520; PubMed Central PMCID: PMC4956074. 8: Cuypers L, Snoeck J, Kerremans L, Libin P, Crabbé R, Van Dooren S, Vuagniaux G, Vandamme AM. HCV1b genome evolution under selective pressure of the cyclophilin inhibitor alisporivir during the DEB-025-HCV-203 phase II clinical trial. Infect Genet Evol. 2016 Oct;44:169-181. doi: 10.1016/j.meegid.2016.06.050. Epub 2016 Jun 30. PubMed PMID: 27374748. 9: Šileikytė J, Forte M. Shutting down the pore: The search for small molecule inhibitors of the mitochondrial permeability transition. Biochim Biophys Acta. 2016 Aug;1857(8):1197-1202. doi: 10.1016/j.bbabio.2016.02.016. Epub 2016 Feb 26. Review. PubMed PMID: 26924772; PubMed Central PMCID: PMC4893955. 10: Esser-Nobis K, Schmidt J, Nitschke K, Neumann-Haefelin C, Thimme R, Lohmann V. The cyclophilin-inhibitor alisporivir stimulates antigen presentation thereby promoting antigen-specific CD8(+) T cell activation. J Hepatol. 2016 Jun;64(6):1305-14. doi: 10.1016/j.jhep.2016.02.027. Epub 2016 Feb 26. PubMed PMID: 26921685. 11: Bo Q, Orsenigo R, Wang J, Griffel L, Brass C. Glucose abnormalities in Asian patients with chronic hepatitis C. Drug Des Devel Ther. 2015 Nov 9;9:6009-17. doi: 10.2147/DDDT.S92060. eCollection 2015. PubMed PMID: 26609222; PubMed Central PMCID: PMC4644176. 12: Gallay PA, Bobardt MD, Chatterji U, Trepanier DJ, Ure D, Ordonez C, Foster R. The Novel Cyclophilin Inhibitor CPI-431-32 Concurrently Blocks HCV and HIV-1 Infections via a Similar Mechanism of Action. PLoS One. 2015 Aug 11;10(8):e0134707. doi: 10.1371/journal.pone.0134707. eCollection 2015. PubMed PMID: 26263487; PubMed Central PMCID: PMC4532424. 13: Zeuzem S, Flisiak R, Vierling JM, Mazur W, Mazzella G, Thongsawat S, Abdurakhmanov D, Van Kính N, Calistru P, Heo J, Stanciu C, Gould M, Makara M, Hsu SJ, Buggisch P, Samuel D, Mutimer D, Nault B, Merz M, Bao W, Griffel LH, Brass C, Naoumov NV; ESSENTIAL II Study Group. Randomised clinical trial: alisporivir combined with peginterferon and ribavirin in treatment-naïve patients with chronic HCV genotype 1 infection (ESSENTIAL II). Aliment Pharmacol Ther. 2015 Oct;42(7):829-44. doi: 10.1111/apt.13342. Epub 2015 Aug 4. PubMed PMID: 26238707. 14: Pawlotsky JM, Flisiak R, Sarin SK, Rasenack J, Piratvisuth T, Chuang WL, Peng CY, Foster GR, Shah S, Wedemeyer H, Hézode C, Zhang W, Wong KA, Li B, Avila C, Naoumov NV; VITAL-1 study team. Alisporivir plus ribavirin, interferon free or in combination with pegylated interferon, for hepatitis C virus genotype 2 or 3 infection. Hepatology. 2015 Oct;62(4):1013-23. doi: 10.1002/hep.27960. Epub 2015 Aug 10. PubMed PMID: 26118427. 15: Nelson DR, Cooper JN, Lalezari JP, Lawitz E, Pockros PJ, Gitlin N, Freilich BF, Younes ZH, Harlan W, Ghalib R, Oguchi G, Thuluvath PJ, Ortiz-Lasanta G, Rabinovitz M, Bernstein D, Bennett M, Hawkins T, Ravendhran N, Sheikh AM, Varunok P, Kowdley KV, Hennicken D, McPhee F, Rana K, Hughes EA; ALLY-3 Study Team. All-oral 12-week treatment with daclatasvir plus sofosbuvir in patients with hepatitis C virus genotype 3 infection: ALLY-3 phase III study. Hepatology. 2015 Apr;61(4):1127-35. doi: 10.1002/hep.27726. Epub 2015 Mar 10. PubMed PMID: 25614962; PubMed Central PMCID: PMC4409820. 16: Barve A, Kovacs SJ, Ke J, Crabbe R, Grosgurin P, Menetrey A, Nicolas-Métral V, Dabovic K, Dole K, Zhang J, Praestgaard J, Sunkara G, Stein D. The effects of CYP3A4 induction and inhibition on the pharmacokinetics of alisporivir in humans. Clin Pharmacol Drug Dev. 2015 Jan;4(1):25-32. doi: 10.1002/cpdd.114. Epub 2014 May 26. PubMed PMID: 27128001. 17: Buti M, Flisiak R, Kao JH, Chuang WL, Streinu-Cercel A, Tabak F, Calistru P, Goeser T, Rasenack J, Horban A, Davis GL, Alberti A, Mazzella G, Pol S, Orsenigo R, Brass C. Alisporivir with peginterferon/ribavirin in patients with chronic hepatitis C genotype 1 infection who failed to respond to or relapsed after prior interferon-based therapy: FUNDAMENTAL, a Phase II trial. J Viral Hepat. 2015 Jul;22(7):596-606. doi: 10.1111/jvh.12360. Epub 2014 Nov 21. PubMed PMID: 25412795. 18: Cunningham ME, Javaid A, Waters J, Davidson-Wright J, Wong JL, Jones M, Foster GR. Development and validation of a "capture-fusion" model to study drug sensitivity of patient-derived hepatitis C. Hepatology. 2015 Apr;61(4):1192-204. doi: 10.1002/hep.27570. Epub 2015 Feb 13. PubMed PMID: 25330450. 19: Fu J, Tjandra M, Becker C, Bednarczyk D, Capparelli M, Elling R, Hanna I, Fujimoto R, Furegati M, Karur S, Kasprzyk T, Knapp M, Leung K, Li X, Lu P, Mergo W, Miault C, Ng S, Parker D, Peng Y, Roggo S, Rivkin A, Simmons RL, Wang M, Wiedmann B, Weiss AH, Xiao L, Xie L, Xu W, Yifru A, Yang S, Zhou B, Sweeney ZK. Potent nonimmunosuppressive cyclophilin inhibitors with improved pharmaceutical properties and decreased transporter inhibition. J Med Chem. 2014 Oct 23;57(20):8503-16. doi: 10.1021/jm500862r. Epub 2014 Oct 13. PubMed PMID: 25310383. 20: Phillips S, Chokshi S, Chatterji U, Riva A, Bobardt M, Williams R, Gallay P, Naoumov NV. Alisporivir inhibition of hepatocyte cyclophilins reduces HBV replication and hepatitis B surface antigen production. Gastroenterology. 2015 Feb;148(2):403-14.e7. doi: 10.1053/j.gastro.2014.10.004. Epub 2014 Oct 8. PubMed PMID: 25305505.