Dapivirine
new
featured

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

MedKoo CAT#: 317132

CAS#: 244767-67-7

Description: 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.


Price and Availability

Size
Price

25mg
USD 150
200mg
USD 450
2g
USD 1650
Size
Price

50mg
USD 250
500mg
USD 650
5g
USD 2650
Size
Price

100mg
USD 350
1g
USD 950
10g
USD 4650

Dapivirine, purity > 98%, is in stock. The same day shipping out after order is received. Note: the estimated shipping out time for order > 2g may be 2 weeks.


Chemical Structure

img

Theoretical Analysis

MedKoo Cat#: 317132
Name: Dapivirine
CAS#: 244767-67-7
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; Dapivirine.

IUPAC/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)

Certificate of Analysis:

Safety Data Sheet (MSDS):

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: 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: 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.

3: 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.

4: 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.

5: 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.

6: Parsons TL, Emory JF, Seserko LA, Aung WS, Marzinke MA. Dual quantification of dapivirine and maraviroc in cervicovaginal secretions from ophthalmic tear strips and polyester-based swabs via liquid chromatographic-tandem mass spectrometric (LC-MS/MS) analysis. J Pharm Biomed Anal. 2014 Sep;98:407-16. doi: 10.1016/j.jpba.2014.06.018. Epub 2014 Jun 21. PubMed PMID: 25005891; PubMed Central PMCID: PMC4143664.

7: Nel A, Haazen W, Nuttall J, Romano J, Rosenberg Z, van Niekerk N. A safety and pharmacokinetic trial assessing delivery of dapivirine from a vaginal ring in healthy women. AIDS. 2014 Jun 19;28(10):1479-87. doi: 10.1097/QAD.0000000000000280. PubMed PMID: 24901365.

8: Murphy DJ, Desjardins D, Dereuddre-Bosquet N, Brochard P, Perrot L, Pruvost A, Le Grand R, Lagatie O, Vanhooren L, Feyaerts M, van Roey J, Malcolm RK. Pre-clinical development of a combination microbicide vaginal ring containing dapivirine and darunavir. J Antimicrob Chemother. 2014 Sep;69(9):2477-88. doi: 10.1093/jac/dku160. Epub 2014 May 26. PubMed PMID: 24862093.

9: Akil A, Devlin B, Cost M, Rohan LC. Increased Dapivirine tissue accumulation through vaginal film codelivery of dapivirine and Tenofovir. Mol Pharm. 2014 May 5;11(5):1533-41. doi: 10.1021/mp4007024. Epub 2014 Apr 14. PubMed PMID: 24693866; PubMed Central PMCID: PMC4018102.

10: das Neves J, Araújo F, Andrade F, Amiji M, Bahia MF, Sarmento B. Biodistribution and pharmacokinetics of dapivirine-loaded nanoparticles after vaginal delivery in mice. Pharm Res. 2014 Jul;31(7):1834-45. doi: 10.1007/s11095-013-1287-x. Epub 2014 Jan 22. PubMed PMID: 24449442.

11: Seserko LA, Emory JF, Hendrix CW, Marzinke MA. The development and validation of an UHPLC-MS/MS method for the rapid quantification of the antiretroviral agent dapivirine in human plasma. Bioanalysis. 2013 Nov;5(22):2771-83. doi: 10.4155/bio.13.256. PubMed PMID: 24256358; PubMed Central PMCID: PMC4104354.

12: Devlin B, Nuttall J, Wilder S, Woodsong C, Rosenberg Z. Development of dapivirine vaginal ring for HIV prevention. Antiviral Res. 2013 Dec;100 Suppl:S3-8. doi: 10.1016/j.antiviral.2013.09.025. Epub 2013 Nov 1. Review. PubMed PMID: 24188702.

13: Cranston RD, Hoesley C, Carballo-Diéguez A, Hendrix CW, Husnik M, Levy L, Hall W, Soto-Torres L, Nel AM. A randomized male tolerance study of dapivirine gel following multiple topical penile exposures (MTN 012/IPM 010). AIDS Res Hum Retroviruses. 2014 Feb;30(2):184-9. doi: 10.1089/AID.2013.0170. Epub 2013 Oct 26. PubMed PMID: 24070431; PubMed Central PMCID: PMC3910451.

14: das Neves J, Amiji M, Bahia MF, Sarmento B. Assessing the physical-chemical properties and stability of dapivirine-loaded polymeric nanoparticles. Int J Pharm. 2013 Nov 18;456(2):307-14. doi: 10.1016/j.ijpharm.2013.08.049. Epub 2013 Sep 4. PubMed PMID: 24012910.

15: das Neves J, Araújo F, Andrade F, Michiels J, Ariën KK, Vanham G, Amiji M, Bahia MF, Sarmento B. In vitro and ex vivo evaluation of polymeric nanoparticles for vaginal and rectal delivery of the anti-HIV drug dapivirine. Mol Pharm. 2013 Jul 1;10(7):2793-807. doi: 10.1021/mp4002365. Epub 2013 Jun 17. PubMed PMID: 23738946.

16: Gorajana A, Ying CC, Shuang Y, Fong P, Tan Z, Gupta J, Talekar M, Sharma M, Garg S. Development of solid dispersion systems of dapivirine to enhance its solubility. Curr Drug Deliv. 2013 Jun;10(3):309-16. PubMed PMID: 23360246.

17: das Neves J, Sarmento B, Amiji M, Bahia MF. Development and validation of a HPLC method for the assay of dapivirine in cell-based and tissue permeability experiments. J Chromatogr B Analyt Technol Biomed Life Sci. 2012 Dec 12;911:76-83. doi: 10.1016/j.jchromb.2012.10.034. Epub 2012 Nov 2. PubMed PMID: 23217310.

18: Major I, Boyd P, Kilbourne-Brook M, Saxon G, Cohen J, Malcolm RK. A modified SILCS contraceptive diaphragm for long-term controlled release of the HIV microbicide dapivirine. Contraception. 2013 Jul;88(1):58-66. doi: 10.1016/j.contraception.2012.10.018. Epub 2012 Nov 21. PubMed PMID: 23177261.

19: Akil A, Parniak MA, Dezzuitti CS, Moncla BJ, Cost MR, Li M, Rohan LC. Development and Characterization of a Vaginal Film Containing Dapivirine, a Non- nucleoside Reverse Transcriptase Inhibitor (NNRTI), for prevention of HIV-1 sexual transmission. Drug Deliv Transl Res. 2011 Jun 1;1(3):209-222. PubMed PMID: 22708075; PubMed Central PMCID: PMC3375737.

20: Schader SM, Oliveira M, Ibanescu RI, Moisi D, Colby-Germinario SP, Wainberg MA. In vitro resistance profile of the candidate HIV-1 microbicide drug dapivirine. Antimicrob Agents Chemother. 2012 Feb;56(2):751-6. doi: 10.1128/AAC.05821-11. Epub 2011 Nov 28. PubMed PMID: 22123692; PubMed Central PMCID: PMC3264246.