Dapivirine

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.

Product information

CAS Number: 244767-67-7

Molecular Weight: 329.40

Formula: C20H19N5

Synonym:

TMC-120

R-147681

TMC120

TMC 120

R 147681

R147681

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

Smiles: CC1C=C(C)C=C(C)C=1NC1=CC=NC(NC2C=CC(=CC=2)C#N)=N1

InChiKey: ILAYIAGXTHKHNT-UHFFFAOYSA-N

InChi: 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)

Technical Data

Appearance: Solid Power.

Purity: ≥98% (or refer to the Certificate of Analysis)

Solubility: Soluble in DMSO, not in water

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 ^oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥360 days if stored properly.

Stock Solution Storage: 0 - 4 ^oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined.

HS Tariff Code: 382200

How to use

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.
2. 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.

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