MedKoo Cat#: 528412 | Name: DPC-963

Description:

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

DPC-963, also known as DMP-963, is a RNA-directed DNA polymerase inhibitor potentially for the treatment of HIV infection. DPC-963 was found to undergo a metabolic activation previously undescribed for structural analogues of this compound. It is postulated that an oxidative defluorination mediated by cytochrome P450 leads to the formation of a putative benzoquinone imine intermediate which subsequently reacts with GSH to form two aromatic ring-substituted regioisomeric conjugates, M5 and M6. In addition to forming the GSH adducts, the benzoquinone imine was also found to be reduced to its unreactive hydroquinone metabolite, which was excreted as the glucuronide conjugate in rat bile.

Chemical Structure

DPC-963
DPC-963
CAS#214287-90-8

Theoretical Analysis

MedKoo Cat#: 528412

Name: DPC-963

CAS#: 214287-90-8

Chemical Formula: C14H9F5N2O

Exact Mass: 316.0635

Molecular Weight: 316.23

Elemental Analysis: C, 53.17; H, 2.87; F, 30.04; N, 8.86; O, 5.06

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
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Synonym
DPC-963; DPC 963; DPC963; DMP-963; DMP963; DMP 963
IUPAC/Chemical Name
(S)-4-(cyclopropylethynyl)-5,6-difluoro-4-(trifluoromethyl)-3,4-dihydroquinazolin-2(1H)-one
InChi Key
QCNJQJJFXFJVCX-ZDUSSCGKSA-N
InChi Code
InChI=1S/C14H9F5N2O/c15-8-3-4-9-10(11(8)16)13(14(17,18)19,21-12(22)20-9)6-5-7-1-2-7/h3-4,7H,1-2H2,(H2,20,21,22)/t13-/m0/s1
SMILES Code
O=C1NC2=C(C(F)=C(F)C=C2)[C@](C(F)(F)F)(C#CC3CC3)N1
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
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
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 316.23 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.

Recalculate based on batch purity %
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: Li S, Ma JA. Core-structure-inspired asymmetric addition reactions: enantioselective synthesis of dihydrobenzoxazinone- and dihydroquinazolinone-based anti-HIV agents. Chem Soc Rev. 2015 Nov 7;44(21):7439-48. doi: 10.1039/c5cs00342c. Review. PubMed PMID: 26177889. 2: Badawy SI, Lee TJ, Menning MM. Effect of drug substance particle size on the characteristics of granulation manufactured in a high-shear mixer. AAPS PharmSciTech. 2000 Nov 17;1(4):E33. PubMed PMID: 14727898; PubMed Central PMCID: PMC2750457. 3: Xie M, Ziemba TM, Maurin MB. Sublimation characterization and vapor pressure estimation of an HIV nonnucleoside reverse transcriptase inhibitor using thermogravimetric analysis. AAPS PharmSciTech. 2003;4(2):E23. PubMed PMID: 12916905; PubMed Central PMCID: PMC2750601. 4: Chen H, Chen W, Gan LS, Mutlib AE. Metabolism of (S)-5,6-difluoro-4-cyclopropylethynyl-4-trifluoromethyl-3, 4-dihydro-2(1H)-quinazolinone, a non-nucleoside reverse transcriptase inhibitor, in human liver microsomes. Metabolic activation and enzyme kinetics. Drug Metab Dispos. 2003 Jan;31(1):122-32. PubMed PMID: 12485961. 5: Chen H, Shockcor J, Chen W, Espina R, Gan LS, Mutlib AE. Delineating novel metabolic pathways of DPC 963, a non-nucleoside reverse transcriptase inhibitor, in rats. Characterization of glutathione conjugates of postulated oxirene and benzoquinone imine intermediates by LC/MS and LC/NMR. Chem Res Toxicol. 2002 Mar;15(3):388-99. PubMed PMID: 11896687. 6: Second-generation drugs fight resistant virus. STEP Perspect. 1999 Winter;99(1):3. PubMed PMID: 11367160. 7: Whitson S. Drug watch. Posit Aware. 1999 May-Jun;10(3):16-7. PubMed PMID: 11366758. 8: New nonnucleoside reverse transcriptase inhibitors. GMHC Treat Issues. 1999 Feb;13(2):10. PubMed PMID: 11366114. 9: Parsons RL Jr. Development of commercially viable enantioselective processes for HIV-1 NNRTIs. Curr Opin Drug Discov Devel. 2000 Nov;3(6):783-92. PubMed PMID: 19649906. 10: Kauffman GS, Harris GD, Dorow RL, Stone BR, Parsons RL Jr, Pesti JA, Magnus NA, Fortunak JM, Confalone PN, Nugent WA. An efficient chiral moderator prepared from inexpensive (+)-3-carene: synthesis of the HIV-1 non-nucleoside reverse transcriptase inhibitor DPC 963. Org Lett. 2000 Oct 5;2(20):3119-21. PubMed PMID: 11009360. 11: Aubry AF, Sebastian D, Hobson T, Xu JQ, Rabel S, Xie M, Gray V. In-use testing of extemporaneously prepared suspensions of second generation non-nucleoside reversed transcriptase inhibitors in support of phase I clinical studies. J Pharm Biomed Anal. 2000 Aug 15;23(2-3):535-42. PubMed PMID: 10933547. 12: Corbett JW, Ko SS, Rodgers JD, Gearhart LA, Magnus NA, Bacheler LT, Diamond S, Jeffrey S, Klabe RM, Cordova BC, Garber S, Logue K, Trainor GL, Anderson PS, Erickson-Viitanen SK. Inhibition of clinically relevant mutant variants of HIV-1 by quinazolinone non-nucleoside reverse transcriptase inhibitors. J Med Chem. 2000 May 18;43(10):2019-30. PubMed PMID: 10821714. 13: Corbett JW, Ko SS, Rodgers JD, Jeffrey S, Bacheler LT, Klabe RM, Diamond S, Lai CM, Rabel SR, Saye JA, Adams SP, Trainor GL, Anderson PS, Erickson-Viitanen SK. Expanded-spectrum nonnucleoside reverse transcriptase inhibitors inhibit clinically relevant mutant variants of human immunodeficiency virus type 1. Antimicrob Agents Chemother. 1999 Dec;43(12):2893-7. PubMed PMID: 10582878; PubMed Central PMCID: PMC89583.