Emivirine

Names

[ Name ]:
Emivirine

[Synonym ]:
I-EBU
1EtOMe6Bz5i-Pr-U
Emivirine
Emivirine [USAN:INN]
[14C]-Emivirine
1-(ethoxymethyl)-5-(1-methylethyl)-6-(phenylmethyl)pyrimidine-2,4(1H,3H)-dione
Coactinon
Mkc 442
1-ethoxymethyl-5-isopropyl-6-benzyluracil
6-benzyl-1-(ethoxymethyl)-5-isopropyl uracil
6-benzyl-1-(ethoxymethyl)-5-propan-2-ylpyrimidine-2,4-dione

Biological Activity

[Description]:

Emivirine (MKC-442) is a non-nucleoside reverse transcriptase inhibitors (NNRTIs) with Ki values of 0.20 and 0.01 μM for dTTP- and dGTP-dependent DNA or RNA polymerase activity, respectively. Emivirine displays potent and selective anti-human immunodeficiency virus type 1 (HIV-1) activity[1][2].

[Related Catalog]:

Signaling Pathways >> Anti-infection >> HIV

Research Areas >> Infection

Research Areas >> Inflammation/Immunology

[In Vitro]

Emivirine (EMV) is also specific for HIV-1 RT and was without effect on HIV-2[2]. Emivirine (EMV) has no obvious toxicity for human healthy cells[2]. Cell Viability Assay[2] Cell Line: Human bone marrow cells collected from normal healthy volunteers. Concentration: 0, 0.1, 1, 10, or 100 μM. Incubation Time: 14 days. Result: At concentrations of 0.1 to 10 μM, no effect on cell growth, lactic acid production, mitochondrial DNA synthesis, or mitochondrial structure was seen compared to what occurred with untreated HepG2 cells.

[In Vivo]

Tthe approximate lethal oral dose of Emivirine (EMV) for rats was ≥3 g/kg for males and 2.5 g/kg for females[2]. Animal Model: Male Sprague-Dawley rats[2]. Dosage: 50 mg/kg. Administration: Gavage. Result: The oral absorption was 68%.

[References]

[1]. Panita Decha, et al. Theoretical studies on the molecular basis of HIV-1RT/NNRTIs interactions. J Enzyme Inhib Med Chem. 2011 Feb;26(1):29-36.

[2]. G M Szczech, et al. 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.

Chemical & Physical Properties

[ Molecular Formula ]:
C₁₇H₂₂N₂O₃

[ Molecular Weight ]:
302.37

[ Exact Mass ]:
302.16300

[ PSA ]:
64.09000

[ LogP ]:
2.24480

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: UV9088750

CHEMICAL NAME :: 2,4(1H,3H)-Pyrimidinedione, 1-(ethoxymethyl)-5-(1-methylethyl)-6-(phenylmethyl)-

CAS REGISTRY NUMBER :: 149950-60-7

LAST UPDATED :: 199603

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C17-H22-N2-O3

MOLECULAR WEIGHT :: 302.41

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >2 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JMCMAR Journal of Medicinal Chemistry. (American Chemical Soc., Distribution Office Dept. 223, POB POB 57136, West End Stn., Washington, DC 20037) V.6- 1963- Volume(issue)/page/year: 38,2860,1995

Safety Information

[ HS Code ]:
2933990090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2933990090

[ Summary ]:
2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%