Simeprevir sodium
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MedKoo CAT#: 314237

CAS#: 1241946-89-3 (sodium)

Description: 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

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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: 0.00
Molecular Weight: 771.924
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 Quantity
25mg USD 90 Ready to ship
50mg USD 150 Ready to ship
100mg USD 250 Ready to ship
200mg USD 450 Ready to ship
500mg USD 950 Ready to ship
1g USD 1650 Ready to ship
2g USD 2950 Ready to ship
5g USD 6450 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)

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/

Solubility Data

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

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.

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
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: 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.
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.

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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.