Amenamevir | ASP2151 | CAS#841301-32-4 | herpes virus helicase-primase inhibitor

MedKoo Cat#: 319848 | Name: Amenamevir

Description:

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

Amenamevir, also known as ASP2151, is a herpes virus helicase-primase inhibitor. ASP2151 had significantly better anti-HSV activity against herpes simplex keratitis than valacyclovir and acyclovir after systemic or topical use.

Chemical Structure

Amenamevir

CAS#841301-32-4

Theoretical Analysis

MedKoo Cat#: 319848

Name: Amenamevir

CAS#: 841301-32-4

Chemical Formula: C24H26N4O5S

Exact Mass: 482.1624

Molecular Weight: 482.56

Elemental Analysis: C, 59.74; H, 5.43; N, 11.61; O, 16.58; S, 6.64

Price and Availability

Size	Price	Availability
10mg	USD 90.00	Ready to ship
25mg	USD 150.00	Ready to ship
50mg	USD 250.00	Ready to ship
100mg	USD 450.00	Ready to ship
200mg	USD 750.00	Ready to ship
500mg	USD 1,650.00	Ready to ship
1g	USD 2,950.00	Ready to ship
2g	USD 5,250.00	Ready to ship

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Related CAS #

No Data

Synonym

ASP2151; ASP-2151; ASP 2151; Amenamevir

IUPAC/Chemical Name

N-(2-((4-(1,2,4-oxadiazol-3-yl)phenyl)amino)-2-oxoethyl)-N-(2,6-dimethylphenyl)tetrahydro-2H-thiopyran-4-carboxamide 1,1-dioxide

InChi Key

MNHNIVNAFBSLLX-UHFFFAOYSA-N

InChi Code

InChI=1S/C24H26N4O5S/c1-16-4-3-5-17(2)22(16)28(24(30)19-10-12-34(31,32)13-11-19)14-21(29)26-20-8-6-18(7-9-20)23-25-15-33-27-23/h3-9,15,19H,10-14H2,1-2H3,(H,26,29)

SMILES Code

O=C(C(CC1)CCS1(=O)=O)N(C2=C(C)C=CC=C2C)CC(NC3=CC=C(C4=NOC=N4)C=C3)=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

Certificate of Analysis

View CoA: current batch, Lot#A9T10K14

QC Data

View QC data: current batch, Lot#A9T10K14

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Amenamevir is a helicase-primase inhibitor which has antiviral activity against HSVs with an EC50 of 14 ng/mL.

In vitro activity:

The inhibitory activity of ASP2151 against helicase–primase complex was assayed using the recombinant UL5–UL52–UL8 complex of HSV-1 strain KOS. HSV helicase–primase complex has multiple enzymatic activities, namely DNA helicase and ssDNA-dependent ATPase activity catalysed by the UL5 helicase subunit and primase activity catalysed by the UL52 primase subunit. Results showed that ASP2151 inhibited the DNA helicase activity of the complex at concentrations of ≥0.1 μM (Figure 1b). Similarly, the ssDNA-dependent ATPase activity was inhibited in a concentration-dependent manner with a mean IC50 value of 0.078 µM [n = 3, standard error (SE) 0.016 μM]. Interestingly, ASP2151 also inhibited the primase activity at concentrations of ≥0.03 µM (Figure 1c). Reference: J Antimicrob Chemother. 2010 Aug;65(8):1733-41. https://academic.oup.com/jac/article/65/8/1733/741947

In vivo activity:

To investigate the antiviral effect of amenamevir, a VZV (herpes zoster virus) and HSV (herpes simplex virus) helicase-primase inhibitor, in severe infection conditions, mouse models of severe HSV-1 infection were developed by immunosuppression or multidermatomal infection. Mice with cyclosporin-induced immunosuppression and HSV-1 infection via inoculation of a dorsolateral area of skin were orally treated with amenamevir (10-100 mg/kg/day) for different durations (2-5 days). Immunosuppressed mice maintained high skin HSV-1 titers in the absence of treatment. Amenamevir successfully reduced HSV-1 titers at all tested doses in immunosuppressed mice, but required a longer treatment period to avoid a rebound in viral titers due to immunosuppression. Reference: Biochem Pharmacol. 2018 Dec;158:201-206. https://www.sciencedirect.com/science/article/abs/pii/S0006295218304519?via%3Dihub

	Solvent	mg/mL	mM
Solubility
	DMF:PBS (pH 7.2) (1:20)	0.0	0.08
	DMF	2.0	4.14

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 482.56 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. Katsumata K, Chono K, Suzuki H. Antiviral efficacy of the helicase-primase inhibitor amenamevir in murine models of severe herpesvirus infection. Biochem Pharmacol. 2018 Dec;158:201-206. doi: 10.1016/j.bcp.2018.10.024. Epub 2018 Oct 24. PMID: 30365949. 2. Chono K, Katsumata K, Kontani T, Kobayashi M, Sudo K, Yokota T, Konno K, Shimizu Y, Suzuki H. ASP2151, a novel helicase-primase inhibitor, possesses antiviral activity against varicella-zoster virus and herpes simplex virus types 1 and 2. J Antimicrob Chemother. 2010 Aug;65(8):1733-41. doi: 10.1093/jac/dkq198. Epub 2010 Jun 9. PMID: 20534624.

In vitro protocol:

1. Chono K, Katsumata K, Kontani T, Kobayashi M, Sudo K, Yokota T, Konno K, Shimizu Y, Suzuki H. ASP2151, a novel helicase-primase inhibitor, possesses antiviral activity against varicella-zoster virus and herpes simplex virus types 1 and 2. J Antimicrob Chemother. 2010 Aug;65(8):1733-41. doi: 10.1093/jac/dkq198. Epub 2010 Jun 9. PMID: 20534624.

In vivo protocol:

1: Shiraki K, Yasumoto S, Toyama N, Fukuda H. Amenamevir, a Helicase-Primase Inhibitor, for the Optimal Treatment of Herpes Zoster. Viruses. 2021 Aug 5;13(8):1547. doi: 10.3390/v13081547. PMID: 34452412; PMCID: PMC8402822. 2: Shoji N, Tanese K, Sasaki A, Horiuchi T, Utsuno Y, Fukuda K, Hoshino Y, Noda S, Minami H, Asakura W; Amenamevir Review Team. Pharmaceuticals and Medical Device Agency approval summary: Amenamevir for the treatment of herpes zoster. J Dermatol. 2020 Jul;47(7):683-688. doi: 10.1111/1346-8138.15393. Epub 2020 May 18. PMID: 32424854. 3: Shiraki K. Helicase-primase inhibitor amenamevir for herpesvirus infection: Towards practical application for treating herpes zoster. Drugs Today (Barc). 2017 Nov;53(11):573-584. doi: 10.1358/dot.2017.53.11.2724803. PMID: 29451274. 4: Umemoto Y, Tanaka S, Kambayashi A, Sugimoto K, Kashiwagura Y, Namiki N, Uchida S. Gummi Formulations Comprising Amenamevir Solid Dispersions with Polyvinyl Alcohol. Chem Pharm Bull (Tokyo). 2021;69(9):862-871. doi: 10.1248/cpb.c21-00278. PMID: 34470950. 5: Kawashima M, Miyachi Y. A 1-Year Survey of Zoster-Associated Pain after Amenamevir Treatment. Dermatol Ther (Heidelb). 2022 May;12(5):1239-1252. doi: 10.1007/s13555-022-00727-9. Epub 2022 May 2. PMID: 35501661; PMCID: PMC9110593. 6: Andrei G, Snoeck R. Advances and Perspectives in the Management of Varicella- Zoster Virus Infections. Molecules. 2021 Feb 20;26(4):1132. doi: 10.3390/molecules26041132. PMID: 33672709; PMCID: PMC7924330. 7: Kawashima M, Imafuku S, Fujio K, Komazaki H. Single-Dose, Patient-Initiated Amenamevir Therapy for Recurrent Genital Herpes: A Phase 3, Randomized, Double- Blind, Placebo-Controlled Study. Open Forum Infect Dis. 2022 Sep 22;9(10):ofac494. doi: 10.1093/ofid/ofac494. PMID: 36267254; PMCID: PMC9578154. 8: Adeloye T, Sahgal O, Puri A, Warrington S, Endo T, Dennison J, Johnston A. Amenamevir: Studies of Potential CYP3A-Mediated Pharmacokinetic Interactions With Midazolam, Cyclosporine, and Ritonavir in Healthy Volunteers. Clin Pharmacol Drug Dev. 2018 Nov;7(8):844-859. doi: 10.1002/cpdd.586. Epub 2018 Jul 25. PMID: 30044899; PMCID: PMC6585933. 9: Sadowski LA, Upadhyay R, Greeley ZW, Margulies BJ. Current Drugs to Treat Infections with Herpes Simplex Viruses-1 and -2. Viruses. 2021 Jun 25;13(7):1228. doi: 10.3390/v13071228. PMID: 34202050; PMCID: PMC8310346. 10: Kusawake T, Keirns JJ, Kowalski D, den Adel M, Groenendaal-van de Meent D, Takada A, Ohtsu Y, Katashima M. Pharmacokinetics and Safety of Amenamevir in Healthy Subjects: Analysis of Four Randomized Phase 1 Studies. Adv Ther. 2017 Dec;34(12):2625-2637. doi: 10.1007/s12325-017-0642-4. Epub 2017 Nov 13. PMID: 29134426; PMCID: PMC5709458. 11: Dennison J, Puri A, Warrington S, Endo T, Adeloye T, Johnston A. Amenamevir: Studies of Potential CYP2C8- and CYP2B6-Mediated Pharmacokinetic Interactions With Montelukast and Bupropion in Healthy Volunteers. Clin Pharmacol Drug Dev. 2018 Nov;7(8):860-870. doi: 10.1002/cpdd.578. Epub 2018 Jun 5. PMID: 29870591; PMCID: PMC6221039. 12: Itoh K, Mitsuke Y, Wakahara M, Yoshioka T, Otsuki N, Suzuki Y, Kiriba C, Kuwata A, Sakamaki I, Iwasaki H, Tsutani H. Aseptic Meningitis after Amenamevir Treatment for Herpes Zoster in the First Branch of the Trigeminal Nerve. Intern Med. 2022 Sep 15;61(18):2809-2811. doi: 10.2169/internalmedicine.8581-21. Epub 2022 Feb 26. PMID: 35228415; PMCID: PMC9556230. 13: Kawashima M, Nemoto O, Honda M, Watanabe D, Nakayama J, Imafuku S, Kato T, Katsuramaki T; study investigators. Amenamevir, a novel helicase-primase inhibitor, for treatment of herpes zoster: A randomized, double-blind, valaciclovir-controlled phase 3 study. J Dermatol. 2017 Nov;44(11):1219-1227. doi: 10.1111/1346-8138.13948. Epub 2017 Jul 5. PMID: 28681394; PMCID: PMC5697646. 14: Shiraki K, Takemoto M, Daikoku T. Emergence of varicella-zoster virus resistance to acyclovir: epidemiology, prevention, and treatment. Expert Rev Anti Infect Ther. 2021 Nov;19(11):1415-1425. doi: 10.1080/14787210.2021.1917992. Epub 2021 Apr 28. PMID: 33853490. 15: Kobayashi H, Yoshida Y, Komoshita T, Suma H, Hosokawa Y, Hirose Y, Sugimoto T, Mokuda S, Hirata S, Sugiyama E. The Efficacy of Amenamevir for the Treatment of Disseminated Herpes Zoster Complicated with Probable Varicella-zoster Pneumonia in an Immunocompromised Patient. Intern Med. 2022 Jun 1;61(11):1785-1788. doi: 10.2169/internalmedicine.8104-21. Epub 2021 Nov 13. PMID: 34776482; PMCID: PMC9259304. 16: Shiraki K, Tan L, Daikoku T, Takemoto M, Sato N, Yoshida Y. Viral ribonucleotide reductase attenuates the anti-herpes activity of acyclovir in contrast to amenamevir. Antiviral Res. 2020 Aug;180:104829. doi: 10.1016/j.antiviral.2020.104829. Epub 2020 Jun 20. PMID: 32569704. 17: Sato Y, Suenaga T, Kobayashi M, Miyazaki N, Suzuki T, Ishioka K, Suzutani T. Characteristics of Helicase-Primase Inhibitor Amenamevir-Resistant Herpes Simplex Virus. Antimicrob Agents Chemother. 2021 Sep 17;65(10):e0049421. doi: 10.1128/AAC.00494-21. Epub 2021 Jul 6. PMID: 34228537; PMCID: PMC8448106. 18: Onaka T, Shiraki K, Yonezawa A. Improvement of acyclovir-resistant herpes zoster infection by amenamevir. J Dermatol. 2021 Sep;48(9):e478-e479. doi: 10.1111/1346-8138.16027. Epub 2021 Jun 16. PMID: 34137062. 19: Kusawake T, den Adel M, Groenendaal-van de Meent D, Garcia-Hernandez A, Takada A, Kato K, Ohtsu Y, Katashima M. Pharmacokinetic Evaluation of the Interactions of Amenamevir (ASP2151) with Ketoconazole, Rifampicin, Midazolam, and Warfarin in Healthy Adults. Adv Ther. 2017 Nov;34(11):2466-2480. doi: 10.1007/s12325-017-0634-4. Epub 2017 Oct 26. PMID: 29076107; PMCID: PMC5702381. 20: Kato K, den Adel M, Groenendaal-van de Meent D, Ohtsu Y, Takada A, Katashima M. An Open-Label, Single-Dose, Human Mass Balance Study of Amenamevir in Healthy Male Adults. Clin Pharmacol Drug Dev. 2019 Jul;8(5):595-602. doi: 10.1002/cpdd.630. Epub 2018 Nov 9. PMID: 30412362; PMCID: PMC6619336.