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MedKoo Cat#: 330142 | Name: Cenicriviroc Mesylate
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Description:

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

Cenicriviroc, also known as TAK-652 and TBR-652, is an experimental drug candidate for the treatment of HIV infection. It is being developed by Takeda Pharmaceutical and Tobira Therapeutics. Cenicriviroc is an inhibitor of CCR2 and CCR5 receptors, allowing it to function as an entry inhibitor which prevents the virus from entering into a human cell. Inhibition of CCR2 may have an anti-inflammatory effect.

Chemical Structure

Cenicriviroc Mesylate
Cenicriviroc Mesylate
CAS#497223-28-6 (mesylate)

Theoretical Analysis

MedKoo Cat#: 330142

Name: Cenicriviroc Mesylate

CAS#: 497223-28-6 (mesylate)

Chemical Formula: C42H56N4O7S2

Exact Mass: 0.0000

Molecular Weight: 793.05

Elemental Analysis: C, 63.61; H, 7.12; N, 7.06; O, 14.12; S, 8.09

Price and Availability

Size Price Availability Quantity
5mg USD 150.00 Ready to ship
10mg USD 250.00 Ready to ship
25mg USD 450.00 Ready to ship
50mg USD 750.00 Ready to ship
100mg USD 1,350.00 Ready to ship
200mg USD 2,350.00 Ready to ship
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Related CAS #
497223-28-6 (mesylate) 497223-25-3 (free base)
Synonym
Cenicriviroc Mesylate; TAK-652; TAK652; TAK 652; TBR-652; TBR 652; TBR652; Cenicriviroc.
IUPAC/Chemical Name
(S,E)-8-(4-(2-Butoxyethoxy)phenyl)-1-isobutyl-N-(4-(((1-propyl-1H-imidazol-5-yl)methyl)sulfinyl)phenyl)-1,2,3,4-tetrahydrobenzo[b]azocine-5-carboxamide, mesylate
InChi Key
IXPBPUPDRDCRSY-YLZLUMLXSA-N
InChi Code
InChI=1S/C41H52N4O4S.CH4O3S/c1-5-7-22-48-23-24-49-38-15-10-32(11-16-38)33-12-19-40-35(25-33)26-34(9-8-21-44(40)28-31(3)4)41(46)43-36-13-17-39(18-14-36)50(47)29-37-27-42-30-45(37)20-6-2;1-5(2,3)4/h10-19,25-27,30-31H,5-9,20-24,28-29H2,1-4H3,(H,43,46);1H3,(H,2,3,4)/b34-26+;/t50-;/m0./s1
SMILES Code
O=C(/C1=C/C2=CC(C3=CC=C(OCCOCCCC)C=C3)=CC=C2N(CC(C)C)CCC1)NC4=CC=C([S@](CC5=CN=CN5CCC)=O)C=C4.OS(=O)(C)=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
Biological target:
Cenicriviroc Mesylate (TAK-652 Mesylate) is a dual CCR2/CCR5 antagonist, also inhibits both HIV-1 and HIV-2.
In vitro activity:
When VeroE6/TMPRSS2 cells were infected with SARS-CoV-2 and incubated in the absence of compounds for 3 days, the cells were completely destroyed by the virus-induced cytopathic effect (Fig. 1 B). Such cell destruction was not observed for the infected cells in the presence of 20 μM CVC (Cenicriviroc), although some morphological changes were identified (Fig. 1D). In contrast, MRV did not inhibit the virus-induced cell destruction even at 40 μM (Fig. 1F). The EC50s of CVC and MRV were 19 ± 0.2 and >40 μM, respectively, based on the inhibition of virus-induced cell destruction (Table 1 ). Both compounds did not show apparent cytotoxicity at concentrations up to 80 μM. Dose-dependent protection of the infected cells from virus-induced cell destruction was observed for CVC but not for MRV (Fig. 2 ). These results indicate that CVC is a selective inhibitor of SARS-CoV-2 replication. Reference: Antiviral Res. 2020 Oct; 182: 104902. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7392080/
In vivo activity:
In the von Frey test, strong mechanical hypersensitivity was observed 7 days after CCI at both examined time points compared to naive animals (Figures 1B, C). One hour after i.t. administration of cenicriviroc, a significant analgesic effect was observed at all tested doses, and a dose-dependent trend was clearly noticeable (Figure 1C), while 30 min after drug administration, only the two highest doses (Figure 1B) induced analgesia in neuropathic rats. Furthermore, at 7 days after sciatic nerve injury, strong thermal hypersensitivity was evoked, as measured by the cold plate test (Figures 1D, E). Significant attenuation of those painful effects was observed for all tested doses at both 30 min (Figure 1D) and 60 min (Figure 1E) after cenicriviroc administration. Reference: Front Immunol. 2020; 11: 615327. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7779470/
Solvent mg/mL mM
Solubility
DMSO 100.0 126.10
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 793.05 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. Okamoto M, Toyama M, Baba M. The chemokine receptor antagonist cenicriviroc inhibits the replication of SARS-CoV-2 in vitro. Antiviral Res. 2020 Oct;182:104902. doi: 10.1016/j.antiviral.2020.104902. Epub 2020 Jul 30. PMID: 32739404; PMCID: PMC7392080. 2. D'Antoni ML, Mitchell BI, McCurdy S, Byron MM, Ogata-Arakaki D, Chow D, Mehta NN, Boisvert WA, Lefebvre E, Shikuma CM, Ndhlovu LC, Baumer Y. Cenicriviroc inhibits trans-endothelial passage of monocytes and is associated with impaired E-selectin expression. J Leukoc Biol. 2018 Dec;104(6):1241-1252. doi: 10.1002/JLB.5A0817-328RRR. Epub 2018 Aug 8. PMID: 30088682; PMCID: PMC6258344. 3. Kwiatkowski K, Pawlik K, Ciapała K, Piotrowska A, Makuch W, Mika J. Bidirectional Action of Cenicriviroc, a CCR2/CCR5 Antagonist, Results in Alleviation of Pain-Related Behaviors and Potentiation of Opioid Analgesia in Rats With Peripheral Neuropathy. Front Immunol. 2020 Dec 21;11:615327. doi: 10.3389/fimmu.2020.615327. PMID: 33408720; PMCID: PMC7779470. 4. Li M, Lu C, Zhu H, Kang X, Wang F, Shao L, Lu X, Chen W, Xia X. Cenicriviroc ameliorates the severity of graft-versus-host disease through inhibition of CCR5 in a rat model of liver transplantation. Am J Transl Res. 2019 Jun 15;11(6):3438-3449. Erratum in: Am J Transl Res. 2020 Mar 15;12(3):1166. PMID: 31312356; PMCID: PMC6614659.
In vitro protocol:
1. Okamoto M, Toyama M, Baba M. The chemokine receptor antagonist cenicriviroc inhibits the replication of SARS-CoV-2 in vitro. Antiviral Res. 2020 Oct;182:104902. doi: 10.1016/j.antiviral.2020.104902. Epub 2020 Jul 30. PMID: 32739404; PMCID: PMC7392080. 2. D'Antoni ML, Mitchell BI, McCurdy S, Byron MM, Ogata-Arakaki D, Chow D, Mehta NN, Boisvert WA, Lefebvre E, Shikuma CM, Ndhlovu LC, Baumer Y. Cenicriviroc inhibits trans-endothelial passage of monocytes and is associated with impaired E-selectin expression. J Leukoc Biol. 2018 Dec;104(6):1241-1252. doi: 10.1002/JLB.5A0817-328RRR. Epub 2018 Aug 8. PMID: 30088682; PMCID: PMC6258344.
In vivo protocol:
1. Kwiatkowski K, Pawlik K, Ciapała K, Piotrowska A, Makuch W, Mika J. Bidirectional Action of Cenicriviroc, a CCR2/CCR5 Antagonist, Results in Alleviation of Pain-Related Behaviors and Potentiation of Opioid Analgesia in Rats With Peripheral Neuropathy. Front Immunol. 2020 Dec 21;11:615327. doi: 10.3389/fimmu.2020.615327. PMID: 33408720; PMCID: PMC7779470. 2. Li M, Lu C, Zhu H, Kang X, Wang F, Shao L, Lu X, Chen W, Xia X. Cenicriviroc ameliorates the severity of graft-versus-host disease through inhibition of CCR5 in a rat model of liver transplantation. Am J Transl Res. 2019 Jun 15;11(6):3438-3449. Erratum in: Am J Transl Res. 2020 Mar 15;12(3):1166. PMID: 31312356; PMCID: PMC6614659.
1: Tacke F. Cenicriviroc for the treatment of non-alcoholic steatohepatitis and liver fibrosis. Expert Opin Investig Drugs. 2018 Mar;27(3):301-311. doi: 10.1080/13543784.2018.1442436. Epub 2018 Feb 22. PMID: 29448843. 2: Sumida Y, Yoneda M. Current and future pharmacological therapies for NAFLD/NASH. J Gastroenterol. 2018 Mar;53(3):362-376. doi: 10.1007/s00535-017-1415-1. Epub 2017 Dec 16. PMID: 29247356; PMCID: PMC5847174. 3: Ratziu V, Sanyal A, Harrison SA, Wong VW, Francque S, Goodman Z, Aithal GP, Kowdley KV, Seyedkazemi S, Fischer L, Loomba R, Abdelmalek MF, Tacke F. Cenicriviroc Treatment for Adults With Nonalcoholic Steatohepatitis and Fibrosis: Final Analysis of the Phase 2b CENTAUR Study. Hepatology. 2020 Sep;72(3):892-905. doi: 10.1002/hep.31108. Epub 2020 Jul 21. PMID: 31943293. 4: Fraile JM, Palliyil S, Barelle C, Porter AJ, Kovaleva M. Non-Alcoholic Steatohepatitis (NASH) - A Review of a Crowded Clinical Landscape, Driven by a Complex Disease. Drug Des Devel Ther. 2021 Sep 22;15:3997-4009. doi: 10.2147/DDDT.S315724. PMID: 34588764; PMCID: PMC8473845. 5: Diaz Soto MP, Lim JK. Evaluating the Therapeutic Potential of Cenicriviroc in the Treatment of Nonalcoholic Steatohepatitis with Fibrosis: A Brief Report on Emerging Data. Hepat Med. 2020 Aug 13;12:115-123. doi: 10.2147/HMER.S230613. PMID: 32884369; PMCID: PMC7434517. 6: Attia SL, Softic S, Mouzaki M. Evolving Role for Pharmacotherapy in NAFLD/NASH. Clin Transl Sci. 2021 Jan;14(1):11-19. doi: 10.1111/cts.12839. Epub 2020 Aug 25. PMID: 32583961; PMCID: PMC7877845. 7: Files DC, Tacke F, O'Sullivan A, Dorr P, Ferguson WG, Powderly WG. Rationale of using the dual chemokine receptor CCR2/CCR5 inhibitor cenicriviroc for the treatment of COVID-19. PLoS Pathog. 2022 Jun 24;18(6):e1010547. doi: 10.1371/journal.ppat.1010547. PMID: 35749425; PMCID: PMC9231801. 8: D'Antoni ML, Mitchell BI, McCurdy S, Byron MM, Ogata-Arakaki D, Chow D, Mehta NN, Boisvert WA, Lefebvre E, Shikuma CM, Ndhlovu LC, Baumer Y. Cenicriviroc inhibits trans-endothelial passage of monocytes and is associated with impaired E-selectin expression. J Leukoc Biol. 2018 Dec;104(6):1241-1252. doi: 10.1002/JLB.5A0817-328RRR. Epub 2018 Aug 8. PMID: 30088682; PMCID: PMC6258344. 9: Neokosmidis G, Tziomalos K. Role of cenicriviroc in the management of nonalcoholic fatty liver disease. World J Gastroenterol. 2018 Dec 28;24(48):5415-5417. doi: 10.3748/wjg.v24.i48.5415. PMID: 30622370; PMCID: PMC6319130. 10: O'Halloran JA, Ko ER, Anstrom KJ, Kedar E, McCarthy MW, Panettieri RA Jr, Maillo M, Nunez PS, Lachiewicz AM, Gonzalez C, Smith PB, de Tai SM, Khan A, Lora AJM, Salathe M, Capo G, Gonzalez DR, Patterson TF, Palma C, Ariza H, Lima MP, Blamoun J, Nannini EC, Sprinz E, Mykietiuk A, Alicic R, Rauseo AM, Wolfe CR, Witting B, Wang JP, Parra-Rodriguez L, Der T, Willsey K, Wen J, Silverstein A, O'Brien SM, Al-Khalidi HR, Maldonado MA, Melsheimer R, Ferguson WG, McNulty SE, Zakroysky P, Halabi S, Benjamin DK Jr, Butler S, Atkinson JC, Adam SJ, Chang S, LaVange L, Proschan M, Bozzette SA, Powderly WG; ACTIV-1 IM Study Group Members. Abatacept, Cenicriviroc, or Infliximab for Treatment of Adults Hospitalized With COVID-19 Pneumonia: A Randomized Clinical Trial. JAMA. 2023 Jul 25;330(4):328-339. doi: 10.1001/jama.2023.11043. PMID: 37428480; PMCID: PMC10334296. 11: Miao M, De Clercq E, Li G. Clinical significance of chemokine receptor antagonists. Expert Opin Drug Metab Toxicol. 2020 Jan;16(1):11-30. doi: 10.1080/17425255.2020.1711884. Epub 2020 Jan 17. PMID: 31903790. 12: Visseaux B, Charpentier C, Collin G, Bertine M, Peytavin G, Damond F, Matheron S, Lefebvre E, Brun-Vézinet F, Descamps D; ANRS CO5 HIV-2 Cohort. Cenicriviroc, a Novel CCR5 (R5) and CCR2 Antagonist, Shows In Vitro Activity against R5 Tropic HIV-2 Clinical Isolates. PLoS One. 2015 Aug 6;10(8):e0134904. doi: 10.1371/journal.pone.0134904. PMID: 26247470; PMCID: PMC4527700. 13: Krenkel O, Puengel T, Govaere O, Abdallah AT, Mossanen JC, Kohlhepp M, Liepelt A, Lefebvre E, Luedde T, Hellerbrand C, Weiskirchen R, Longerich T, Costa IG, Anstee QM, Trautwein C, Tacke F. Therapeutic inhibition of inflammatory monocyte recruitment reduces steatohepatitis and liver fibrosis. Hepatology. 2018 Apr;67(4):1270-1283. doi: 10.1002/hep.29544. Epub 2018 Feb 19. PMID: 28940700. 14: Qian T, Fujiwara N, Koneru B, Ono A, Kubota N, Jajoriya AK, Tung MG, Crouchet E, Song WM, Marquez CA, Panda G, Hoshida A, Raman I, Li QZ, Lewis C, Yopp A, Rich NE, Singal AG, Nakagawa S, Goossens N, Higashi T, Koh AP, Bian CB, Hoshida H, Tabrizian P, Gunasekaran G, Florman S, Schwarz ME, Hiotis SP, Nakahara T, Aikata H, Murakami E, Beppu T, Baba H, Rew Warren, Bhatia S, Kobayashi M, Kumada H, Fobar AJ, Parikh ND, Marrero JA, Rwema SH, Nair V, Patel M, Kim-Schulze S, Corey K, O'Leary JG, Klintmalm GB, Thomas DL, Dibas M, Rodriguez G, Zhang B, Friedman SL, Baumert TF, Fuchs BC, Chayama K, Zhu S, Chung RT, Hoshida Y. Molecular Signature Predictive of Long-Term Liver Fibrosis Progression to Inform Antifibrotic Drug Development. Gastroenterology. 2022 Apr;162(4):1210-1225. doi: 10.1053/j.gastro.2021.12.250. Epub 2021 Dec 22. Erratum in: Gastroenterology. 2022 Aug;163(2):536. PMID: 34951993; PMCID: PMC8934284. 15: Tacke F, Weiskirchen R. Non-alcoholic fatty liver disease (NAFLD)/non- alcoholic steatohepatitis (NASH)-related liver fibrosis: mechanisms, treatment and prevention. Ann Transl Med. 2021 Apr;9(8):729. doi: 10.21037/atm-20-4354. PMID: 33987427; PMCID: PMC8106094. 16: Kwiatkowski K, Pawlik K, Ciapała K, Piotrowska A, Makuch W, Mika J. Bidirectional Action of Cenicriviroc, a CCR2/CCR5 Antagonist, Results in Alleviation of Pain-Related Behaviors and Potentiation of Opioid Analgesia in Rats With Peripheral Neuropathy. Front Immunol. 2020 Dec 21;11:615327. doi: 10.3389/fimmu.2020.615327. PMID: 33408720; PMCID: PMC7779470. 17: Shen B, Lu LG. Efficacy and safety of drugs for nonalcoholic steatohepatitis. J Dig Dis. 2021 Feb;22(2):72-82. doi: 10.1111/1751-2980.12967. PMID: 33385317. 18: Ambade A, Lowe P, Kodys K, Catalano D, Gyongyosi B, Cho Y, Iracheta-Vellve A, Adejumo A, Saha B, Calenda C, Mehta J, Lefebvre E, Vig P, Szabo G. Pharmacological Inhibition of CCR2/5 Signaling Prevents and Reverses Alcohol- Induced Liver Damage, Steatosis, and Inflammation in Mice. Hepatology. 2019 Mar;69(3):1105-1121. doi: 10.1002/hep.30249. Epub 2019 Feb 12. PMID: 30179264; PMCID: PMC6393202. 19: Anstee QM, Neuschwander-Tetri BA, Wai-Sun Wong V, Abdelmalek MF, Rodriguez- Araujo G, Landgren H, Park GS, Bedossa P, Alkhouri N, Tacke F, Sanyal AJ. Cenicriviroc Lacked Efficacy to Treat Liver Fibrosis in Nonalcoholic Steatohepatitis: AURORA Phase III Randomized Study. Clin Gastroenterol Hepatol. 2023 Apr 13:S1542-3565(23)00273-2. doi: 10.1016/j.cgh.2023.04.003. Epub ahead of print. PMID: 37061109. 20: Wojaczyńska E, Wojaczyński J. Sulfoxides in medicine. Curr Opin Chem Biol. 2023 Jun 10;76:102340. doi: 10.1016/j.cbpa.2023.102340. Epub ahead of print. PMID: 37307682.

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