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MedKoo Cat#: 318173 | Name: Maraviroc
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Description:

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

Maraviroc is an antiviral, potent, non-competitive CKR-5 receptor antagonist that inhibits binding of HIV viral coat protein gp120. Maraviroc inhibits MIP-1β-stimulated γ-S-GTP binding to HEK-293 cell membranes, indicating its ability to inhibit chemokine-dependent stimulation of GDP-GTP exchange at the CKR-5/G protein complex. Maraviroc also inhibits the downstream event of chemokine-induced intracellular calcium redistribution.

Chemical Structure

Maraviroc
Maraviroc
CAS#376348-65-1

Theoretical Analysis

MedKoo Cat#: 318173

Name: Maraviroc

CAS#: 376348-65-1

Chemical Formula: C29H41F2N5O

Exact Mass: 513.3279

Molecular Weight: 513.68

Elemental Analysis: C, 67.81; H, 8.05; F, 7.40; N, 13.63; O, 3.11

Price and Availability

Size Price Availability Quantity
5mg USD 350.00 2 Weeks
10mg USD 550.00 2 Weeks
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Synonym
Maraviroc; Selzentry; Celsentri; UK-427857; UK-427,857; Pfizer Brand of maraviroc; Selzentry; UK-427,857; UK-427857;
IUPAC/Chemical Name
4,4-difluoro-N-[(1S)-3-[(1S,5R)-3-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octan-8-yl]-1-phenylpropyl]cyclohexane-1-carboxamide
InChi Key
GSNHKUDZZFZSJB-HLMSNRGBSA-N
InChi Code
InChI=1S/C29H41F2N5O/c1-19(2)27-34-33-20(3)36(27)25-17-23-9-10-24(18-25)35(23)16-13-26(21-7-5-4-6-8-21)32-28(37)22-11-14-29(30,31)15-12-22/h4-8,19,22-26H,9-18H2,1-3H3,(H,32,37)/t23-,24+,25?,26-/m0/s1
SMILES Code
CC1=NN=C(N1C2CC3CCC(C2)N3CCC(C4=CC=CC=C4)NC(=O)C5CCC(CC5)(F)F)C(C)C
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# C20M02C10
Safety Data Sheet (SDS)
View Safety Data Sheet (SDS)
Instruction
View handling instruction
Biological target:
Maraviroc (UK-427857) is a selective CCR5 antagonist with activity against human HIV.
In vitro activity:
Maraviroc demonstrated potent antiviral activity against all CCR5-tropic HIV-1 viruses tested, including 43 primary isolates from various clades and diverse geographic origin (geometric mean 90% inhibitory concentration of 2.0 nM). Maraviroc was active against 200 clinically derived HIV-1 envelope-recombinant pseudoviruses, 100 of which were derived from viruses resistant to existing drug classes. Reference: Antimicrob Agents Chemother. 2005 Nov;49(11):4721-32. https://pubmed.ncbi.nlm.nih.gov/16251317/
In vivo activity:
Maraviroc, a clinically approved CCR5 inhibitor drug for HIV treatment, was formulated as a microbicide gel at 5 mM concentration in 2.2% hydroxyl ethyl cellulose. Female RAG-hu mice were challenged vaginally with HIV-1 an hour after intravaginal application of the maraviroc gel. These results showed that maraviroc gel treated mice were fully protected against vaginal HIV-1 challenge in contrast to placebo gel treated mice which all became infected. Reference: PLoS One. 2011;6(6):e20209. https://pubmed.ncbi.nlm.nih.gov/21673796/
Solvent mg/mL mM
Solubility
DMF 5.0 9.73
DMSO 42.2 91.90
Ethanol 45.7 89.00
Ethanol:PBS (pH 7.2) (1:1) 0.5 0.97
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 513.68 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. Mencarelli A, Cipriani S, Francisci D, Santucci L, Baldelli F, Distrutti E, Fiorucci S. Highly specific blockade of CCR5 inhibits leukocyte trafficking and reduces mucosal inflammation in murine colitis. Sci Rep. 2016 Aug 5;6:30802. doi: 10.1038/srep30802. PMID: 27492684; PMCID: PMC4974621. 2. Dorr P, Westby M, Dobbs S, Griffin P, Irvine B, Macartney M, Mori J, Rickett G, Smith-Burchnell C, Napier C, Webster R, Armour D, Price D, Stammen B, Wood A, Perros M. Maraviroc (UK-427,857), a potent, orally bioavailable, and selective small-molecule inhibitor of chemokine receptor CCR5 with broad-spectrum anti-human immunodeficiency virus type 1 activity. Antimicrob Agents Chemother. 2005 Nov;49(11):4721-32. doi: 10.1128/AAC.49.11.4721-4732.2005. PMID: 16251317; PMCID: PMC1280117. 3. Ishihara Y, Honda T, Ishihara N, Namba K, Taketoshi M, Tominaga Y, Tsuji M, Vogel CFA, Yamazaki T, Itoh K, Tominaga T. A CCR5 antagonist, maraviroc, alleviates neural circuit dysfunction and behavioral disorders induced by prenatal valproate exposure. J Neuroinflammation. 2022 Jul 29;19(1):195. doi: 10.1186/s12974-022-02559-y. PMID: 35906621; PMCID: PMC9335995. 4. Neff CP, Kurisu T, Ndolo T, Fox K, Akkina R. A topical microbicide gel formulation of CCR5 antagonist maraviroc prevents HIV-1 vaginal transmission in humanized RAG-hu mice. PLoS One. 2011;6(6):e20209. doi: 10.1371/journal.pone.0020209. Epub 2011 Jun 1. PMID: 21673796; PMCID: PMC3105981.
In vitro protocol:
1. Mencarelli A, Cipriani S, Francisci D, Santucci L, Baldelli F, Distrutti E, Fiorucci S. Highly specific blockade of CCR5 inhibits leukocyte trafficking and reduces mucosal inflammation in murine colitis. Sci Rep. 2016 Aug 5;6:30802. doi: 10.1038/srep30802. PMID: 27492684; PMCID: PMC4974621. 2. Dorr P, Westby M, Dobbs S, Griffin P, Irvine B, Macartney M, Mori J, Rickett G, Smith-Burchnell C, Napier C, Webster R, Armour D, Price D, Stammen B, Wood A, Perros M. Maraviroc (UK-427,857), a potent, orally bioavailable, and selective small-molecule inhibitor of chemokine receptor CCR5 with broad-spectrum anti-human immunodeficiency virus type 1 activity. Antimicrob Agents Chemother. 2005 Nov;49(11):4721-32. doi: 10.1128/AAC.49.11.4721-4732.2005. PMID: 16251317; PMCID: PMC1280117.
In vivo protocol:
1. Ishihara Y, Honda T, Ishihara N, Namba K, Taketoshi M, Tominaga Y, Tsuji M, Vogel CFA, Yamazaki T, Itoh K, Tominaga T. A CCR5 antagonist, maraviroc, alleviates neural circuit dysfunction and behavioral disorders induced by prenatal valproate exposure. J Neuroinflammation. 2022 Jul 29;19(1):195. doi: 10.1186/s12974-022-02559-y. PMID: 35906621; PMCID: PMC9335995. 2. Neff CP, Kurisu T, Ndolo T, Fox K, Akkina R. A topical microbicide gel formulation of CCR5 antagonist maraviroc prevents HIV-1 vaginal transmission in humanized RAG-hu mice. PLoS One. 2011;6(6):e20209. doi: 10.1371/journal.pone.0020209. Epub 2011 Jun 1. PMID: 21673796; PMCID: PMC3105981.
1: Raymond S, Nicot F, Carcenac R, Jeanne N, Cazabat M, Requena M, Cuzin L, Delobel P, Izopet J; ANRS 145 MARIMUNO Study Group. No selection of CXCR4-using variants in cell reservoirs of dual-mixed HIV-infected patients on suppressive maraviroc therapy. AIDS. 2016 Mar 27;30(6):965-8. doi: 10.1097/QAD.0000000000001013. PubMed PMID: 26752281. 2: Ahmed N, Okoli C, Ainsworth J. Ineffective central nervous system HIV suppression of once-a-day maraviroc and ritonavir-boosted darunavir dual therapy: four case reports. Int J STD AIDS. 2016 Mar;27(4):321-2. doi: 10.1177/0956462415584486. Epub 2015 May 11. PubMed PMID: 25969439. 3: Karlsson U, Repits J, Antonsson L, Cederfjäll E, Ljungberg B, Ålenius M, Sabirsh A, Gisslen M, Esbjörnsson J, Jansson M. Reduced Baseline Sensitivity to Maraviroc Inhibition Among R5 HIV-1 Isolates From Individuals With Severe Immunodeficiency. J Acquir Immune Defic Syndr. 2016 Mar 1;71(3):e79-82. doi: 10.1097/QAI.0000000000000873. PubMed PMID: 26492461. 4: Stellbrink HJ, Fevre EL, Carr A, Saag MS, Mukwaya G, Nozza S, Valluri SR, Vourvahis M, Rinehart AR, Mcfadyen L, Fichtenbaum C, Clark A, Craig C, Fang AF, Heera J. Once-daily maraviroc versus tenofovir/emtricitabine each combined with darunavir/ritonavir for initial HIV-1 treatment: 48-week results from the MODERN study. AIDS. 2016 Feb 5. [Epub ahead of print] PubMed PMID: 26854810. 5: Herrera C, Armanasco N, García-Pérez J, Ziprin P, Olejniczak N, Alcami J, Nuttall J, Shattock RJ. Maraviroc and reverse transcriptase inhibitors combinations as potential pre-exposure prophylaxis candidates. AIDS. 2016 Feb 5. [Epub ahead of print] PubMed PMID: 26854808. 6: Gates TM, Cysique LA, Siefried KJ, Chaganti J, Moffat KJ, Brew BJ. Maraviroc-intensified combined antiretroviral therapy improves cognition in virally suppressed HIV-associated neurocognitive disorder. AIDS. 2016 Feb 20;30(4):591-600. doi: 10.1097/QAD.0000000000000951. PubMed PMID: 26825032. 7: Gonzalez-Serna A, Genebat M, Ruiz-Mateos E, Leal M. Short-term maraviroc exposure, a clinical approach to decide on maraviroc prescription in HIV-1-infected treatment-naïve patients. Drug Des Devel Ther. 2016 Jan 18;10:353-6. doi: 10.2147/DDDT.S100639. eCollection 2016. PubMed PMID: 26848259; PubMed Central PMCID: PMC4723024. 8: Ball C, Sudhanva M, Jarosz J, Post FA, Hamlyn E. Is there a role for maraviroc to treat HIV-associated central nervous system white matter disease? AIDS. 2016 Jan;30(2):334-6. doi: 10.1097/QAD.0000000000000954. PubMed PMID: 26684826. 9: Blanco JR, Ochoa-Callejero L. Off-label use of maraviroc in clinical practice. Expert Rev Anti Infect Ther. 2016 Jan;14(1):5-8. doi: 10.1586/14787210.2016.1100535. Epub 2015 Oct 28. PubMed PMID: 26509356. 10: Latinovic OS, Zhang J, Tagaya Y, DeVico AL, Fouts TR, Schneider K, Lakowicz JR, Heredia A, Redfield RR. Synergistic Inhibition of R5 HIV-1 by the Fusion Protein (FLSC) IgG1 Fc and Maraviroc in Primary Cells: Implications for Prevention and Treatment. Curr HIV Res. 2016;14(1):24-36. PubMed PMID: 26354735. 11: Pozo-Balado MM, Rosado-Sánchez I, Méndez-Lagares G, Rodríguez-Méndez MM, Ruiz-Mateos E, Benhnia MR, Muñoz-Fernández MA, Leal M, Pacheco YM. Maraviroc contributes to the restoration of the homeostasis of regulatory T-cell subsets in antiretroviral-naive HIV-infected subjects. Clin Microbiol Infect. 2016 Jan 22. pii: S1198-743X(16)00018-5. doi: 10.1016/j.cmi.2015.12.025. [Epub ahead of print] PubMed PMID: 26806257. 12: Fletcher P, Herrera C, Armanasco N, Nuttall J, Shattock RJ. Limited Anti-HIV-1 Activity of Maraviroc in Mucosal Tissues. AIDS Res Hum Retroviruses. 2016 Jan 29. [Epub ahead of print] PubMed PMID: 26711323. 13: van Lelyveld SF, Symons J, van Ham P, Connell BJ, Nijhuis M, Wensing AM, Hoepelman AI. Clinical outcome of maraviroc-containing therapy in heavily pre-treated HIV-1-infected patients. Int J Antimicrob Agents. 2016 Jan;47(1):84-90. doi: 10.1016/j.ijantimicag.2015.09.013. Epub 2015 Oct 25. PubMed PMID: 26585497. 14: Kwiatkowski K, Piotrowska A, Rojewska E, Makuch W, Jurga A, Slusarczyk J, Trojan E, Basta-Kaim A, Mika J. Beneficial properties of maraviroc on neuropathic pain development and opioid effectiveness in rats. Prog Neuropsychopharmacol Biol Psychiatry. 2016 Jan 4;64:68-78. doi: 10.1016/j.pnpbp.2015.07.005. Epub 2015 Jul 16. PubMed PMID: 26190414. 15: Ostrowski M, Benko E, Yue FY, Kim CJ, Huibner S, Lee T, Singer J, Pankovich J, Laeyendecker O, Kaul R, Kandel G, Kovacs C. Intensifying Antiretroviral Therapy With Raltegravir and Maraviroc During Early Human Immunodeficiency Virus (HIV) Infection Does Not Accelerate HIV Reservoir Reduction. Open Forum Infect Dis. 2015 Sep 22;2(4):ofv138. doi: 10.1093/ofid/ofv138. eCollection 2015 Dec. PubMed PMID: 26512359; PubMed Central PMCID: PMC4621663. 16: Soulié C, Assoumou L, Darty M, Rodriguez C, Donati F, Sayon S, Peytavin G, Valantin MA, Caby F, Schneider L, Canestri A, Costagliola D, Katlama C, Calvez V, Marcelin AG; ROCnRAL ANRS-157 Study Group. Virological factors associated with outcome of dual maraviroc/raltegravir therapy (ANRS-157 trial). J Antimicrob Chemother. 2015 Dec;70(12):3339-44. doi: 10.1093/jac/dkv280. Epub 2015 Sep 22. PubMed PMID: 26396157. 17: Council OD, Swanson MD, Spagnuolo RA, Wahl A, Garcia JV. Role of Semen on Vaginal HIV-1 Transmission and Maraviroc Protection. Antimicrob Agents Chemother. 2015 Dec;59(12):7847-51. doi: 10.1128/AAC.01496-15. Epub 2015 Sep 21. PubMed PMID: 26392489; PubMed Central PMCID: PMC4649249. 18: Dobard CW, Taylor A, Sharma S, Anderson PL, Bushman LR, Chuong D, Pau CP, Hanson D, Wang L, Garcia-Lerma JG, McGowan I, Rohan L, Heneine W. Protection Against Rectal Chimeric Simian/Human Immunodeficiency Virus Transmission in Macaques by Rectal-Specific Gel Formulations of Maraviroc and Tenofovir. J Infect Dis. 2015 Dec 15;212(12):1988-95. doi: 10.1093/infdis/jiv334. Epub 2015 Jun 12. PubMed PMID: 26071566; PubMed Central PMCID: PMC4655858. 19: Jiang X, Feyertag F, Meehan CJ, McCormack GP, Travers SA, Craig C, Westby M, Lewis M, Robertson DL. Characterizing the Diverse Mutational Pathways Associated with R5-Tropic Maraviroc Resistance: HIV-1 That Uses the Drug-Bound CCR5 Coreceptor. J Virol. 2015 Nov;89(22):11457-72. doi: 10.1128/JVI.01384-15. Epub 2015 Sep 2. PubMed PMID: 26339063; PubMed Central PMCID: PMC4645647. 20: Dezzutti CS, Yandura S, Wang L, Moncla B, Teeple EA, Devlin B, Nuttall J, Brown ER, Rohan LC. Pharmacodynamic Activity of Dapivirine and Maraviroc Single Entity and Combination Topical Gels for HIV-1 Prevention. Pharm Res. 2015 Nov;32(11):3768-81. doi: 10.1007/s11095-015-1738-7. Epub 2015 Jun 16. PubMed PMID: 26078001; PubMed Central PMCID: PMC4600024.