Dapivirine


Catalog No. size PriceQuantity
M7066-2 2mg solid $96
M7066-10 10mg solid $401

Description

Cas:244767-67-7

Product Information

Dapivirine, also known as TMC120, is a non-nucleoside inhibitor for HIV reverse transcriptase with IC50 of 24 nM. The HIV-1 replication inhibitor dapivirine (DPV) is one of the most promising drug candidates being used in topical microbicide products for prevention of HIV-1 sexual transmission.

 

Chemical Formula: C20H19N5

 

Exact Mass: 329.16405

 

Molecular Weight: 329.41

 

Elemental Analysis: C, 72.92; H, 5.81; N, 21.26

 

Synonym: 

 

TMC120

TMC 120

TMC-120

R 147681

R-147681

R147681

 

Chemical Name: 4-[[4-[(2,4,6-Trimethylphenyl)amino]-2-pyrimidinyl]amino]benzonitrile

 

InChi Key:

ILAYIAGXTHKHNT-UHFFFAOYSA-N

 

InChi Code: InChI=1S/C20H19N5/c1-13-10-14(2)19(15(3)11-13)24-18-8-9-22-20(25-18)23-17-6-4-16(12-21)5-7-17/h4-11H,1-3H3,(H2,22,23,24,25)

 

Smiles Code:

N#CC1=CC=C(NC2=NC=CC(NC3=C(C)C=C(C)C=C3C)=N2)C=C1

 

 

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).

HS Tariff Code: 2934.99.9001

 

In Vitro:

Dapivirine (4-64 μM, 24, 48, 72, 96 and 120 hours) inhibits proliferation of glioma cells and induces apoptosis (16 μM, 12-48 h).

Dapivirine (8 and 16 μM, 12 h) enhances invasion of glioma cells.

Dapivirine (16 μM, 12 h, 24 h and 48 h) promotes autophagy in U87 cells.

Dapivirine (TMC120-R147681) apparently blocks infection in the primary cultures at a 10 nM concentration, but secondary cultures revealed that a 100 nM concentration was needed to completely prevent proviral integration.

 

In Vivo:

Dapivirine (16 mg/kg, once every 3 days for 12 days) exhibits potent antitumor activity in human glioblastoma models in mice.

Dapivirine has been shown to have a half-life in the range of 65 to 90 h.

 

 

References

 

  1. 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.

 

  1. Palanee-Phillips T, Schwartz K, Brown ER, Govender V, Mgodi N, Kiweewa FM, Nair G, Mhlanga F, Siva S, Bekker LG, Jeenarain N, Gaffoor Z, Martinson F, Makanani B, Naidoo S, Pather A, Phillip J, Husnik MJ, van der Straten A, Soto-Torres L, Baeten J. Characteristics of Women Enrolled into a Randomized Clinical Trial of Dapivirine Vaginal Ring for HIV-1 Prevention. PLoS One. 2015 Jun 10;10(6):e0128857. doi: 10.1371/journal.pone.0128857. eCollection 2015. PubMed PMID: 26061040; PubMed Central PMCID: PMC4489588.

 

  1. Chen BA, Panther L, Marzinke MA, Hendrix CW, Hoesley CJ, van der Straten A, Husnik MJ, Soto-Torres L, Nel A, Johnson S, Richardson-Harman N, Rabe LK, Dezzutti CS. Phase 1 Safety, Pharmacokinetics, and Pharmacodynamics of Dapivirine and Maraviroc Vaginal Rings: a Double-Blind Randomized Trial. J Acquir Immune Defic Syndr. 2015 May 28. [Epub ahead of print] PubMed PMID: 26034880.

 

  1. Das Neves J, Sarmento B. Precise engineering of dapivirine-loaded nanoparticles for the development of anti-HIV vaginal microbicides. Acta Biomater. 2015 May;18:77-87. doi: 10.1016/j.actbio.2015.02.007. Epub 2015 Feb 17. PubMed PMID: 25700657.

 

  1. Grammen C, Plum J, Van Den Brande J, Darville N, Augustyns K, Augustijns P, Brouwers J. The use of supersaturation for the vaginal application of microbicides: a case study with dapivirine. J Pharm Sci. 2014 Nov;103(11):3696-703. doi: 10.1002/jps.24176. Epub 2014 Sep 17. PubMed PMID: 25231545.

 

Products are for research use only. Not for human use.

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