QDIS Blog

Somehow I missed when it was originally announced that a new once-a-day HIV combination has been approved by the FDA. But Mark over at Eye On FDA has a great post about just how important this is.

Eye on FDA: A Win for the FDA and for 3 Companies - Gilead, BMS and Merck

This is indeed a major breakthrough and should change how AIDS is treated world-wide. It makes it much easier to get compliance from people on the drugs. One of the problems in developing countries is trying to get patients to stick to a strict schedule of when the various drug cocktails need to be taken and not sticking to it can lead to development of drug resistant virus.

For those interested, here is the chemical structure for the three drug combo.

Efavirenz: Efavirenz is chemically described as (S)-6-chloro-4-(cyclopropylethynyl)-
1,4-dihydro-4-(trifluoromethyl)-2H-3,1-benzoxazin-2-one. Its molecular formula is
C14H9ClF3NO2 and its structural formula is:

Efavirenz is a white to slightly pink crystalline powder with a molecular mass of 315.68.
It is practically insoluble in water (<10 μg/mL).

Emtricitabine: The chemical name of emtricitabine is 5-fluoro-1-(2R,5S)-[2-
(hydroxymethyl)-1,3-oxathiolan-5-yl]cytosine. Emtricitabine is the (-) enantiomer of a
thio analog of cytidine, which differs from other cytidine analogs in that it has a fluorine
in the 5-position.
It has a molecular formula of C8H10FN3O3S and a molecular weight of 247.24. It has the
following structural formula:

Emtricitabine is a white to off-white crystalline powder with a solubility of approximately
112 mg/mL in water at 25 °C.

Tenofovir disoproxil fumarate: Tenofovir DF is a fumaric acid salt of the bis-
isopropoxycarbonyloxymethyl ester derivative of tenofovir. The chemical name of
tenofovir disoproxil fumarate is 9-[(R)-2[[bis[[(isopropoxycarbonyl)oxy]-
methoxy]phosphinyl]methoxy]propyl]adenine fumarate (1:1). It has a molecular formula
of C19H30N5O10P • C4H4O4 and a molecular weight of 635.52. It has the following
structural formula:

Tenofovir DF is a white to off-white crystalline powder with a solubility of 13.4 mg/mL in
water at 25 °C.

Further information

• BMS press release on Atripla
• Gilead — U.S. Food and Drug Administration (FDA) Approves ATRIPLA(TM) (efavirenz 600 mg/ emtricitabine 200 mg/ tenofovir disoproxil fumarate 300 mg), The First Once-Daily Single Tablet Regimen for Adults with HIV-1 Infection
• Full prescribing information from Gilead (pdf)
• CNN.com - Single-dose ‘cocktail’ OK’d for U.S. HIV patients - Jul 12, 2006

Blog posting about Atripla

• DOCFILES: Atripla : Once daily tablet for treatment of HIV1
• The J Train: Atripla
• The Biotech Weblog: FDA Approves Atripla, Once Daily Single Tablet AIDS Drug

Technorati Tags: FDA, HIV drugs, Atripla

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