Simeprevir sodium | TMC435 | CAS#923604-59-5 | 1241946-89-3

MedKoo Cat#: 314237 | Name: Simeprevir sodium

Description:

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

Simeprevir, also known as TMC43, is a drug for the treatment and cure of hepatitis C. In the United States, simeprevir is approved by the Food and Drug Administration for use in combination with peginterferon-alfa and ribavirin for hepatitis C and hepatitis B. Simeprevir has been approved in Japan for the treatment of chronic hepatitis C infection, genotype 1.

Chemical Structure

Simeprevir sodium

CAS#1241946-89-3 (sodium)

Theoretical Analysis

MedKoo Cat#: 314237

Name: Simeprevir sodium

CAS#: 1241946-89-3 (sodium)

Chemical Formula: C38H46N5NaO7S2

Exact Mass: 0.0000

Molecular Weight: 771.92

Elemental Analysis: C, 59.13; H, 6.01; N, 9.07; Na, 2.98; O, 14.51; S, 8.31

Price and Availability

Size	Price	Availability
25mg	USD 90.00	Ready to ship
50mg	USD 150.00	Ready to ship
100mg	USD 250.00	Ready to ship
200mg	USD 450.00	Ready to ship
500mg	USD 950.00	Ready to ship
1g	USD 1,650.00	Ready to ship
2g	USD 2,950.00	Ready to ship
5g	USD 6,450.00	Ready to ship

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Related CAS #

923604-59-5 (free base) 1241946-89-3 (sodium)

Synonym

TMC435; TMC 435; TMC435; Simeprevir; Olysio.

IUPAC/Chemical Name

sodium (cyclopropylsulfonyl)((2R,3aR,11aS,12aR,14aR,Z)-2-((2-(4-isopropylthiazol-2-yl)-7-methoxy-8-methylquinolin-4-yl)oxy)-5-methyl-4,14-dioxo-1,2,3,3a,4,5,6,7,8,9,11a,12,12a,13,14,14a-hexadecahydrocyclopenta[c]cyclopropa[g][1,6]diazacyclotetradecine-12a-carbonyl)amide

InChi Key

LLXQGDWGCCKOQP-MVZLLIIPSA-M

InChi Code

InChI=1S/C38H47N5O7S2.Na/c1-21(2)30-20-51-35(40-30)29-18-32(26-13-14-31(49-5)22(3)33(26)39-29)50-24-16-27-28(17-24)36(45)43(4)15-9-7-6-8-10-23-19-38(23,41-34(27)44)37(46)42-52(47,48)25-11-12-25;/h8,10,13-14,18,20-21,23-25,27-28H,6-7,9,11-12,15-17,19H2,1-5H3,(H2,41,42,44,46);/q;+1/p-1/b10-8-;/t23-,24-,27-,28-,38-;/m1./s1

SMILES Code

O=C([N-]S(=O)(C1CC1)=O)[C@]23NC([C@@](C[C@@H](OC4=CC(C5=NC(C(C)C)=CS5)=NC6=C(C)C(OC)=CC=C46)C7)([H])[C@]7([H])C(N(C)CCCC/C=C\[C@]2([H])C3)=O)=O.[Na+]

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

Related CAS# 1241946-89-3 (Simeprevir sodium) 923604-59-5 (Simeprevir)

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#X7P04R20

QC Data

View QC data: current batch, Lot#X7P04R20

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Simeprevir is a potent NS3/4A protease inhibitor.

In vitro activity:

Simeprevir demonstrated genotoxic effects in HepG2 cells; the highest concentration of simeprevir exhibited cytotoxicity. Simeprevir increased micronuclei frequency at higher concentrations. Combinations with ribavirin showed significant results for both simeprevir and sofosbuvir. Interestingly, the combination index indicated antagonism, suggesting a reduction in the genotoxic effects of ribavirin when combined with sofosbuvir or simeprevir. Reference: An Acad Bras Cienc. 2021 Sep 24;93(4):e20200632. https://pubmed.ncbi.nlm.nih.gov/34586319/

In vivo activity:

The results of this study imply that simeprevir does not inhibit SARS-CoV-2 in vivo. In a transgenic hACE2 mouse model of SARS-CoV-2 infection, intraperitoneal administration of simeprevir for 3 consecutive days failed to suppress viral replication. Reference: Int J Antimicrob Agents. 2022 Jan;59(1):106499. https://pubmed.ncbi.nlm.nih.gov/34929295/

	Solvent	mg/mL	mM
Solubility
	DMSO	30.0	38.86
	DMSO:PBS (pH 7.2) (1:2)	0.3	0.43
	DMF	30.0	38.86

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 771.92 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. Librelotto CS, Souza AP, Álvares-DA-Silva MR, Simon D, Dihl RR. Evaluation of the genetic toxicity of sofosbuvir and simeprevir with and without ribavirin in a human-derived liver cell line. An Acad Bras Cienc. 2021 Sep 24;93(4):e20200632. doi: 10.1590/0001-3765202120200632. PMID: 34586319. 2. Murai K, Shimakami T, Welsch C, Shirasaki T, Liu F, Kitabayashi J, Tanaka S, Funaki M, Omura H, Nishikawa T, Sumiyadorj A, Honda M, Kaneko S. Unexpected Replication Boost by Simeprevir for Simeprevir-Resistant Variants in Genotype 1a Hepatitis C Virus. Antimicrob Agents Chemother. 2018 Jun 26;62(7):e02601-17. doi: 10.1128/AAC.02601-17. PMID: 29661883; PMCID: PMC6021633. 3. Li Y, She P, Xu L, Liu Y, Liu S, Li Z, Yang Y, Li L, Hussain Z, Wu Y. Anti-hepatitis C virus drug simeprevir: a promising antimicrobial agent against MRSA. Appl Microbiol Biotechnol. 2022 Apr;106(7):2689-2702. doi: 10.1007/s00253-022-11878-2. Epub 2022 Mar 26. PMID: 35338386. 4. Muturi E, Hong W, Li J, Yang W, He J, Wei H, Yang H. Effects of simeprevir on the replication of SARS-CoV-2 in vitro and in transgenic hACE2 mice. Int J Antimicrob Agents. 2022 Jan;59(1):106499. doi: 10.1016/j.ijantimicag.2021.106499. Epub 2021 Dec 17. PMID: 34929295; PMCID: PMC8679493.

In vitro protocol:

In vivo protocol:

1. Li Y, She P, Xu L, Liu Y, Liu S, Li Z, Yang Y, Li L, Hussain Z, Wu Y. Anti-hepatitis C virus drug simeprevir: a promising antimicrobial agent against MRSA. Appl Microbiol Biotechnol. 2022 Apr;106(7):2689-2702. doi: 10.1007/s00253-022-11878-2. Epub 2022 Mar 26. PMID: 35338386. 2. Muturi E, Hong W, Li J, Yang W, He J, Wei H, Yang H. Effects of simeprevir on the replication of SARS-CoV-2 in vitro and in transgenic hACE2 mice. Int J Antimicrob Agents. 2022 Jan;59(1):106499. doi: 10.1016/j.ijantimicag.2021.106499. Epub 2021 Dec 17. PMID: 34929295; PMCID: PMC8679493.

1: Kanda T, Nakamoto S, Wu S, Yokosuka O. New treatments for genotype 1 chronic hepatitis C - focus on simeprevir. Ther Clin Risk Manag. 2014 May 24;10:387-94. doi: 10.2147/TCRM.S50170. eCollection 2014. Review. PubMed PMID: 24920913; PubMed Central PMCID: PMC4043814. 2: Gaetano JN. Benefit-risk assessment of new and emerging treatments for hepatitis C: focus on simeprevir and sofosbuvir. Drug Healthc Patient Saf. 2014 Mar 31;6:37-45. doi: 10.2147/DHPS.S43304. eCollection 2014. Review. PubMed PMID: 24729731; PubMed Central PMCID: PMC3976205. 3: You DM, Pockros PJ. Simeprevir for the treatment of chronic hepatitis C. Expert Opin Pharmacother. 2013 Dec;14(18):2581-9. doi: 10.1517/14656566.2013.850074. Epub 2013 Oct 19. Review. PubMed PMID: 24138198.