Cenicriviroc
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MedKoo CAT#: 317128

CAS#: 497223-25-3 (free base)

Description: 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

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Cenicriviroc
CAS# 497223-25-3 (free base)

Theoretical Analysis

MedKoo Cat#: 317128
Name: Cenicriviroc
CAS#: 497223-25-3 (free base)
Chemical Formula: C41H52N4O4S
Exact Mass: 696.37093
Molecular Weight: 696.95
Elemental Analysis: C, 70.66; H, 7.52; N, 8.04; O, 9.18; S, 4.60

Size Price Shipping out time Quantity
100mg USD 1650 2 Weeks
200mg USD 2650 2 Weeks
500mg USD 3650 2 Weeks
1g USD 4650 2 Weeks
2g USD 7950 2 Weeks
Inquire bulk and customized quantity

Pricing updated 2021-03-02. Prices are subject to change without notice.

Cenicriviroc, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.

Related CAS #: 497223-28-6 (mesylate)   497223-25-3 (free base)    

Synonym: 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

InChi Key: PNDKCRDVVKJPKG-WHERJAGFSA-N

InChi Code: InChI=1S/C41H52N4O4S/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/h10-19,25-27,30-31H,5-9,20-24,28-29H2,1-4H3,(H,43,46)/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

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

Handling Instructions:

Preparing Stock Solutions

The following data is based on the product molecular weight 696.95 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.

Select a batch to recalculate based on the batch molecular weight:
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

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1: Kruger AJ, Fuchs BC, Masia R, Holmes JA, Salloum S, Sojoodi M, Ferreira DS, Rutledge SM, Caravan P, Alatrakchi N, Vig P, Lefebvre E, Chung RT. Prolonged cenicriviroc therapy reduces hepatic fibrosis despite steatohepatitis in a diet-induced mouse model of nonalcoholic steatohepatitis. Hepatol Commun. 2018 Mar 7;2(5):529-545. doi: 10.1002/hep4.1160. eCollection 2018 May. PubMed PMID: 29761169; PubMed Central PMCID: PMC5944590.

2: Liang F, Giordano C, Shang D, Li Q, Petrof BJ. The dual CCR2/CCR5 chemokine receptor antagonist Cenicriviroc reduces macrophage infiltration and disease severity in Duchenne muscular dystrophy (Dmdmdx-4Cv) mice. PLoS One. 2018 Mar 21;13(3):e0194421. doi: 10.1371/journal.pone.0194421. eCollection 2018. PubMed PMID: 29561896; PubMed Central PMCID: PMC5862483.

3: 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. Review. PubMed PMID: 29448843.

4: Yu D, Cai SY, Mennone A, Vig P, Boyer JL. Cenicriviroc, a cytokine receptor antagonist, potentiates all-trans retinoic acid in reducing liver injury in cholestatic rodents. Liver Int. 2018 Jun;38(6):1128-1138. doi: 10.1111/liv.13698. Epub 2018 Feb 13. PubMed PMID: 29356312.

5: Puengel T, Krenkel O, Kohlhepp M, Lefebvre E, Luedde T, Trautwein C, Tacke F. Differential impact of the dual CCR2/CCR5 inhibitor cenicriviroc on migration of monocyte and lymphocyte subsets in acute liver injury. PLoS One. 2017 Sep 14;12(9):e0184694. doi: 10.1371/journal.pone.0184694. eCollection 2017. PubMed PMID: 28910354; PubMed Central PMCID: PMC5598992.

6: Friedman SL, Ratziu V, Harrison SA, Abdelmalek MF, Aithal GP, Caballeria J, Francque S, Farrell G, Kowdley KV, Craxi A, Simon K, Fischer L, Melchor-Khan L, Vest J, Wiens BL, Vig P, Seyedkazemi S, Goodman Z, Wong VW, Loomba R, Tacke F, Sanyal A, Lefebvre E. A randomized, placebo-controlled trial of cenicriviroc for treatment of nonalcoholic steatohepatitis with fibrosis. Hepatology. 2018 May;67(5):1754-1767. doi: 10.1002/hep.29477. Epub 2018 Jan 29. PubMed PMID: 28833331; PubMed Central PMCID: PMC5947654.

7: Lefebvre E, Moyle G, Reshef R, Richman LP, Thompson M, Hong F, Chou HL, Hashiguchi T, Plato C, Poulin D, Richards T, Yoneyama H, Jenkins H, Wolfgang G, Friedman SL. Antifibrotic Effects of the Dual CCR2/CCR5 Antagonist Cenicriviroc in Animal Models of Liver and Kidney Fibrosis. PLoS One. 2016 Jun 27;11(6):e0158156. doi: 10.1371/journal.pone.0158156. eCollection 2016. PubMed PMID: 27347680; PubMed Central PMCID: PMC4922569.

8: Lefebvre E, Gottwald M, Lasseter K, Chang W, Willett M, Smith PF, Somasunderam A, Utay NS. Pharmacokinetics, Safety, and CCR2/CCR5 Antagonist Activity of Cenicriviroc in Participants With Mild or Moderate Hepatic Impairment. Clin Transl Sci. 2016 Jun;9(3):139-48. doi: 10.1111/cts.12397. Epub 2016 May 12. PubMed PMID: 27169903; PubMed Central PMCID: PMC5351328.

9: Friedman S, Sanyal A, Goodman Z, Lefebvre E, Gottwald M, Fischer L, Ratziu V. Efficacy and safety study of cenicriviroc for the treatment of non-alcoholic steatohepatitis in adult subjects with liver fibrosis: CENTAUR Phase 2b study design. Contemp Clin Trials. 2016 Mar;47:356-65. doi: 10.1016/j.cct.2016.02.012. Epub 2016 Mar 2. PubMed PMID: 26944023.

10: Thompson M, Saag M, DeJesus E, Gathe J, Lalezari J, Landay AL, Cade J, Enejosa J, Lefebvre E, Feinberg J. A 48-week randomized phase 2b study evaluating cenicriviroc versus efavirenz in treatment-naive HIV-infected adults with C-C chemokine receptor type 5-tropic virus. AIDS. 2016 Mar 27;30(6):869-78. doi: 10.1097/QAD.0000000000000988. PubMed PMID: 26636929; PubMed Central PMCID: PMC4794136.

11: Kuwata T, Enomoto I, Baba M, Matsushita S. Incompatible Natures of the HIV-1 Envelope in Resistance to the CCR5 Antagonist Cenicriviroc and to Neutralizing Antibodies. Antimicrob Agents Chemother. 2015 Nov 2;60(1):437-50. doi: 10.1128/AAC.02285-15. Print 2016 Jan. PubMed PMID: 26525792; PubMed Central PMCID: PMC4704143.

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. eCollection 2015. PubMed PMID: 26247470; PubMed Central PMCID: PMC4527700.

13: Kramer VG, Hassounah S, Colby-Germinario SP, Oliveira M, Lefebvre E, Mesplède T, Wainberg MA. The dual CCR5 and CCR2 inhibitor cenicriviroc does not redistribute HIV into extracellular space: implications for plasma viral load and intracellular DNA decline. J Antimicrob Chemother. 2015 Mar;70(3):750-6. doi: 10.1093/jac/dku451. Epub 2014 Nov 27. PubMed PMID: 25433008.

14: Kramer V, Hassounah S, Colby-Germinario S, Mesplède T, Lefebvre E, Wainberg M. Cenicriviroc blocks HIV entry but does not lead to redistribution of HIV into extracellular space like maraviroc. J Int AIDS Soc. 2014 Nov 2;17(4 Suppl 3):19531. doi: 10.7448/IAS.17.4.19531. eCollection 2014. PubMed PMID: 25394040; PubMed Central PMCID: PMC4224821.

15: Menning MM, Dalziel SM. Fumaric acid microenvironment tablet formulation and process development for crystalline cenicriviroc mesylate, a BCS IV compound. Mol Pharm. 2013 Nov 4;10(11):4005-15. doi: 10.1021/mp400286s. Epub 2013 Sep 4. PubMed PMID: 23941629.

16: Kagan RM, Johnson EP, Siaw MF, Van Baelen B, Ogden R, Platt JL, Pesano RL, Lefebvre E. Comparison of genotypic and phenotypic HIV type 1 tropism assay: results from the screening samples of Cenicriviroc Study 202, a randomized phase II trial in treatment-naive subjects. AIDS Res Hum Retroviruses. 2014 Feb;30(2):151-9. doi: 10.1089/AID.2013.0123. Epub 2013 Aug 14. PubMed PMID: 23875707; PubMed Central PMCID: PMC3911766.

17: Klibanov OM, Williams SH, Iler CA. Cenicriviroc, an orally active CCR5 antagonist for the potential treatment of HIV infection. Curr Opin Investig Drugs. 2010 Aug;11(8):940-50. PubMed PMID: 20721836.