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

MedKoo CAT#: 318173

CAS#: 376348-65-1

Description: 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.


Price and Availability

Size
Price

10mg
USD 250
Size
Price

25mg
USD 450
Size
Price

50mg
USD 850

Maraviroc, 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.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 318173
Name: Maraviroc
CAS#: 376348-65-1
Chemical Formula: C29H41F2N5O
Exact Mass: 513.32792
Molecular Weight: 513.67
Elemental Analysis: C, 67.81; H, 8.05; F, 7.40; N, 13.63; O, 3.11


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


Technical Data

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).

Harmonized System Code:
293490


References

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.