WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 315293
CAS#: 206361-99-1 (free)
Description: Darunavir is a drug used to treat HIV infection. It is in the protease inhibitor class. Prezista is an OARAC recommended treatment option for treatment-naïve and treatment-experienced adults and adolescents. Developed by pharmaceutical company Tibotec, darunavir is named after Arun K. Ghosh, the chemist who discovered the molecule at the University of Illinois at Chicago. It was approved by the Food and Drug Administration (FDA) on June 23, 2006.
MedKoo Cat#: 315293
CAS#: 206361-99-1 (free)
Chemical Formula: C27H37N3O7S
Exact Mass: 547.23522
Molecular Weight: 547.66
Elemental Analysis: C, 59.21; H, 6.81; N, 7.67; O, 20.45; S, 5.85
Synonym: TMC114; TMC 114; TMC-114; Darunavir; brand name Prezista.
IUPAC/Chemical Name: (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl ((2S,3R)-4-(4-amino-N-isobutylphenylsulfonamido)-3-hydroxy-1-phenylbutan-2-yl)carbamate
InChi Key: CJBJHOAVZSMMDJ-HEXNFIEUSA-N
InChi Code: InChI=1S/C27H37N3O7S/c1-18(2)15-30(38(33,34)21-10-8-20(28)9-11-21)16-24(31)23(14-19-6-4-3-5-7-19)29-27(32)37-25-17-36-26-22(25)12-13-35-26/h3-11,18,22-26,31H,12-17,28H2,1-2H3,(H,29,32)/t22-,23-,24+,25-,26+/m0/s1
SMILES Code: O=C(O[C@@H]1[C@@]2([H])[C@@](OCC2)([H])OC1)N[C@H]([C@H](O)CN(CC(C)C)S(=O)(C3=CC=C(N)C=C3)=O)CC4=CC=CC=C4
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, DMF, and 1:1 DMF:PBS
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
|Solvent||Max Conc. mg/mL||Max Conc. mM|
|DMF:PBS (pH 7.2) (1:1)||0.5||0.91|
The following data is based on the product molecular weight 547.66 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
|Concentration / Solvent Volume / Mass||1 mg||5 mg||10 mg|
|1 mM||1.15 mL||5.76 mL||11.51 mL|
|5 mM||0.23 mL||1.15 mL||2.3 mL|
|10 mM||0.12 mL||0.58 mL||1.15 mL|
|50 mM||0.02 mL||0.12 mL||0.23 mL|
1: Kakuda TN, Brochot A, Tomaka FL, Vangeneugden T, Van De Casteele T, Hoetelmans RM. Pharmacokinetics and pharmacodynamics of boosted once-daily darunavir. J Antimicrob Chemother. 2014 Jun 20. pii: dku193. [Epub ahead of print] Review. PubMed PMID: 24951533.
2: Afonina LIu, Voronin EE. [Use of darunavir in HIV-infected women during pregnancy]. Ter Arkh. 2013;85(11):109-14. Review. Russian. PubMed PMID: 24432610.
3: Llibre JM, Imaz A, Clotet B. From TMC114 to darunavir: five years of data on efficacy. AIDS Rev. 2013 Apr-Jun;15(2):112-21. Review. PubMed PMID: 23708741.
4: Lorber M. A case of possible darunavir/ritonavir-induced peripheral neuropathy: case description and review of the literature. J Int Assoc Provid AIDS Care. 2013 May-Jun;12(3):162-5. doi: 10.1177/2325957412471993. Epub 2013 Mar 8. Review. PubMed PMID: 23475910.
5: Overton ET, Arathoon E, Baraldi E, Tomaka F. Effect of darunavir on lipid profile in HIV-infected patients. HIV Clin Trials. 2012 Sep-Oct;13(5):256-70. doi: 10.1310/hct1305-256. Review. PubMed PMID: 23134626.
6: Ruela Corrêa JC, D'Arcy DM, dos Reis Serra CH, Nunes Salgado HR. Darunavir: a critical review of its properties, use and drug interactions. Pharmacology. 2012;90(1-2):102-9. doi: 10.1159/000339862. Epub 2012 Jul 12. Review. PubMed PMID: 22797653.
7: Robertson J, Feinberg J. Darunavir : a nonpeptidic protease inhibitor for antiretroviral-naive and treatment-experienced adults with HIV infection. Expert Opin Pharmacother. 2012 Jun;13(9):1363-75. doi: 10.1517/14656566.2012.681776. Epub 2012 May 17. Review. PubMed PMID: 22594781.
8: Phung BC, Yeni P. Darunavir: an effective protease inhibitor for HIV-infected patients. Expert Rev Anti Infect Ther. 2011 Jun;9(6):631-43. doi: 10.1586/eri.11.48. Review. PubMed PMID: 21692667.
9: Fullerton DS, Smets E, De La Rosa G, Mrus JM. Pharmacoeconomics of darunavir. Expert Rev Pharmacoecon Outcomes Res. 2011 Feb;11(1):27-39. doi: 10.1586/erp.10.88. Review. PubMed PMID: 21351854.
10: Dobroszycki J, Abadi J, Wiznia AA, Rosenberg MG. Profile of darunavir in the treatment of HIV-infected pediatric and adolescent patients. Adolesc Health Med Ther. 2011 Sep 14;2:85-93. doi: 10.2147/AHMT.S11177. eCollection 2011. Review. PubMed PMID: 24600277; PubMed Central PMCID: PMC3926773.
PREZISTA (darunavir) is an inhibitor of the human immunodeficiency virus (HIV) protease. PREZISTA (darunavir), in the form of darunavir ethanolate, has the following chemical name: [(1S,2R)-3-[[(4-aminophenyl)sulfonyl](2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]-carbamic acid (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl ester monoethanolate. Its molecular formula is C27H37N3O7S Â• C2H5OH and its molecular weight is 593.73. Darunavir ethanolate is a white to off-white powder with a solubility of approximately 0.15 mg/mL in water at 20Â°C.
Darunavir is a second-generation protease inhibitor (PIs), designed specifically to overcome problems with the older agents in this class, such as indinavir. Early PIs often have severe side effects and drug toxicities, require a high therapeutic dose, are costly to manufacture, and show a disturbing susceptibility to drug resistant mutations. Such mutations can develop in as little as a year of use, and effectively render the drugs useless. Darunavir was designed to form robust interactions with the protease enzyme from many strains of HIV, including strains from treatment-experienced patients with multiple resistance mutations to PIs. Darunavir received much attention at the time of its release, as it represents an important treatment option for patients with drug-resistant HIV. Patient advocacy groups pressured developer Tibotec not to follow the previous trend of releasing new drugs at prices higher than existing drugs in the same class. Darunavir was priced to match other common PIs already in use, such as kaletra. The drug costs around $9000 for a one year supply. (Source: http://en.wikipedia.org/wiki/Darunavir).