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MedKoo Cat#: 326932 | Name: Emivirine
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Description:

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

Emivirine, also known as DRG-0302; I-EBU; MKC-442, is a potent and selective nonnucleoside reverse transcriptase inhibitor of human immunodeficiency virus type 1 for the potential treatment of HIV. It is a non-nucleoside reverse transcriptase inhibitor. While emivirine showed promising antiviral activity in vitro, it failed to show sufficient efficacy in human trials. However it is still notable as an early proof of concept, which led to the discovery of a number of related antiviral drugs.

Chemical Structure

Emivirine
Emivirine
CAS#149950-60-7

Theoretical Analysis

MedKoo Cat#: 326932

Name: Emivirine

CAS#: 149950-60-7

Chemical Formula: C17H22N2O3

Exact Mass: 302.1630

Molecular Weight: 302.37

Elemental Analysis: C, 67.53; H, 7.33; N, 9.26; O, 15.87

Price and Availability

Size Price Availability Quantity
5mg USD 350.00 2 Weeks
200mg USD 1,850.00 2 Weeks
500mg USD 2,850.00 2 Weeks
1g USD 4,650.00 2 Weeks
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Related CAS #
No Data
Synonym
MKC-442; MKC442; MKC 442; DRG-0302; DRG0302; DRG 0302; I-EBU; Emivirine; Coactinon; Emivirina;
IUPAC/Chemical Name
1-(Ethoxymethyl)-5-(1-methylethyl)-6-(phenylmethyl)-2,4(1H,3H)-pyrimidinedione
InChi Key
MLILORUFDVLTSP-UHFFFAOYSA-N
InChi Code
InChI=1S/C17H22N2O3/c1-4-22-11-19-14(10-13-8-6-5-7-9-13)15(12(2)3)16(20)18-17(19)21/h5-9,12H,4,10-11H2,1-3H3,(H,18,20,21)
SMILES Code
O=C1NC(C(C(C)C)=C(CC2=CC=CC=C2)N1COCC)=O
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 302.37 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: Cheonis N. Emivirine: an NRTI that functions as an NNRTI. BETA. 1999;12(4):7-8. PMID: 11367264. 2: Venter WDF, Moorhouse M, Sokhela S, Fairlie L, Mashabane N, Masenya M, Serenata C, Akpomiemie G, Qavi A, Chandiwana N, Norris S, Chersich M, Clayden P, Abrams E, Arulappan N, Vos A, McCann K, Simmons B, Hill A. Dolutegravir plus Two Different Prodrugs of Tenofovir to Treat HIV. N Engl J Med. 2019 Aug 29;381(9):803-815. doi: 10.1056/NEJMoa1902824. Epub 2019 Jul 24. PMID: 31339677. 3: El-Brollosy NR, Loddo R. Synthesis and Antiviral Evaluation of 1-[(2-Phenoxyethyl)oxymethyl] and 6-(3,5-Dimethoxybenzyl) Analogues of HIV Drugs Emivirine and TNK-651. Drug Res (Stuttg). 2016 Apr;66(4):181-8. doi: 10.1055/s-0035-1559683. Epub 2015 Aug 27. PMID: 26313923. 4: Petersen L, Jørgensen PT, Nielsen C, Hansen TH, Nielsen J, Pedersen EB. Synthesis and evaluation of double-prodrugs against HIV. Conjugation of D4T with 6-benzyl-1-(ethoxymethyl)-5-isopropyluracil (MKC-442, emivirine)-type reverse transcriptase inhibitors via the SATE prodrug approach. J Med Chem. 2005 Feb 24;48(4):1211-20. doi: 10.1021/jm040845b. PMID: 15715487. 5: Hopkins AL, Ren J, Tanaka H, Baba M, Okamato M, Stuart DI, Stammers DK. Design of MKC-442 (emivirine) analogues with improved activity against drug- resistant HIV mutants. J Med Chem. 1999 Nov 4;42(22):4500-5. doi: 10.1021/jm990192c. PMID: 10579814. 6: Nitanda T, Wang X, Somekawa K, Yuasa S, Baba M. Three-drug combinations of emivirine and nucleoside reverse transcriptase inhibitors in vitro: long-term culture of HIV-1-infected cells and breakthrough viruses. Antivir Chem Chemother. 2001 May;12(3):161-7. doi: 10.1177/095632020101200303. PMID: 12959324. 7: Boudet N, Knochel P. Chemo- and regioselective functionalization of uracil derivatives. Applications to the synthesis of oxypurinol and emivirine. Org Lett. 2006 Aug 17;8(17):3737-40. doi: 10.1021/ol061295+. PMID: 16898805. 8: El-Brollosy NR, Sørensen ER, Pedersen EB, Sanna G, La Colla P, Loddo R. Synthesis and antiviral evaluation of 6-(trifluoromethylbenzyl) and 6-(fluorobenzyl) analogues of HIV drugs emivirine and GCA-186. Arch Pharm (Weinheim). 2008 Jan;341(1):9-19. doi: 10.1002/ardp.200700113. PMID: 18161905. 9: El-Brollosy NR, Jørgensen PT, Dahan B, Boel AM, Pedersen EB, Nielsen C. Synthesis of novel N-1 (allyloxymethyl) analogues of 6-benzyl-1-(ethoxymethyl)-5-isopropyluracil (MKC-442, emivirine) with improved activity against HIV-1 and its mutants. J Med Chem. 2002 Dec 19;45(26):5721-6. doi: 10.1021/jm020949r. PMID: 12477355. 10: Therkelsen FD, Hansen AL, Pedersen EB, Nielsen C. Multiple pathways in the synthesis of new annelated analogues of 6-benzyl-1-(ethoxymethyl)-5-isopropyluracil (emivirine). Org Biomol Chem. 2003 Aug 21;1(16):2908-18. doi: 10.1039/b303658h. PMID: 12968341. 11: De Clercq E. New developments in anti-HIV chemotherapy. Curr Med Chem. 2001 Nov;8(13):1543-72. doi: 10.2174/0929867013371842. PMID: 11562282. 12: Szczech GM, Furman P, Painter GR, Barry DW, Borroto-Esoda K, Grizzle TB, Blum MR, Sommadossi J, Endoh R, Niwa T, Yamamoto M, Moxham C. Safety assessment, in vitro and in vivo, and pharmacokinetics of emivirine, a potent and selective nonnucleoside reverse transcriptase inhibitor of human immunodeficiency virus type 1. Antimicrob Agents Chemother. 2000 Jan;44(1):123-30. doi: 10.1128/AAC.44.1.123-130.2000. PMID: 10602732; PMCID: PMC89637. 13: Wamberg M, Pedersen EB, El-Brollosy NR, Nielsen C. Synthesis of 6-arylvinyl analogues of the HIV drugs SJ-3366 and Emivirine. Bioorg Med Chem. 2004 Mar 1;12(5):1141-9. doi: 10.1016/j.bmc.2003.11.032. PMID: 14980626. 14: Wamberg M, Pedersen EB, Nielsen C. Synthesis of furoannelated analogues of Emivirine (MKC-442). Arch Pharm (Weinheim). 2004 Mar;337(3):148-51. doi: 10.1002/ardp.200300815. PMID: 15038059. 15: El-Brollosy NR, Al-Deeb OA, El-Emam AA, Pedersen EB, La Colla P, Collu G, Sanna G, Loddo R. Synthesis of novel uracil non-nucleoside derivatives as potential reverse transcriptase inhibitors of HIV-1. Arch Pharm (Weinheim). 2009 Nov;342(11):663-70. doi: 10.1002/ardp.200900139. PMID: 19856332. 16: De Clercq E. New anti-HIV agents and targets. Med Res Rev. 2002 Nov;22(6):531-65. doi: 10.1002/med.10021. PMID: 12369088. 17: De Clercq E. New developments in anti-HIV chemotherapy. Biochim Biophys Acta. 2002 Jul 18;1587(2-3):258-75. doi: 10.1016/s0925-4439(02)00089-3. PMID: 12084468. 18: Bayes M, Rabasseda X, Prous JR. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2004 May;26(4):295-318. PMID: 15319808. 19: Bayés M, Rabasseda X, Prous JR. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2003 Oct;25(8):653-82. PMID: 14671684. 20: De Clercq E. New developments in anti-HIV chemotherapy. Farmaco. 2001 Jan- Feb;56(1-2):3-12. doi: 10.1016/s0014-827x(01)01007-2. PMID: 11347962.