RN-18 is an HIV-1 Vif inhibitor. RN-18 antagonizes Vif function and inhibits HIV-1 replication only in the presence of A3G. RN-18 increases cellular A3G levels in a Vif-dependent manner and increases A3G incorporation into virions without inhibiting general proteasome-mediated protein degradation. RN-18 enhances Vif degradation only in the presence of A3G, reduces viral infectivity by increasing A3G incorporation into virions and enhances cytidine deamination of the viral genome.

Physicochemical Properties

Molecular Formula	C20H16N2O4S
Molecular Weight	380.418
Exact Mass	380.083
Elemental Analysis	C, 63.15; H, 4.24; N, 7.36; O, 16.82; S, 8.43
CAS #	431980-38-0
Related CAS #	431980-38-0
PubChem CID	1317590
Appearance	Solid powder
LogP	5.914
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	5
Heavy Atom Count	27
Complexity	505
Defined Atom Stereocenter Count	0
SMILES	S(C1C=CC(=CC=1)[N+](=O)[O-])C1=CC=CC=C1C(NC1C=CC=CC=1OC)=O
InChi Key	JKNUDHUHXMELIJ-UHFFFAOYSA-N
InChi Code	InChI=1S/C20H16N2O4S/c1-26-18-8-4-3-7-17(18)21-20(23)16-6-2-5-9-19(16)27-15-12-10-14(11-13-15)22(24)25/h2-13H,1H3,(H,21,23)
Chemical Name	N-(2-methoxyphenyl)-2-[(4-nitrophenyl)thio]-benzamide
Synonyms	RN-18; RN 18; RN18.
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

Targets	nonpermissive H9 cell（ IC50=6 μM ）
ln Vitro	Strong antiviral activity is shown by RN-18 and RN-19 in nonpermissive H9 and CEM cells, but not in MT4 or CEM-SS cells, indicating that the antiviral action was Vif specific. Between the two compounds, RN-18 exhibits higher specificity (IC50>100 μM in MT4 cells) and potency (IC50=4.5 μM in CEM cells[1]. Reverse transcriptase activity in the nonpermissive H9 and CEM cells is significantly and dose-dependently reduced in the presence of the inhibitor, RN-18. While RN-18 does not show antiviral activity in the original CEM-SS cell line, it does show antiviral activity in CEM-SS modified to stably express A3G. If A3G is present, only then does RN-18 counteract Vif function and prevent HIV-1 replication. RN-18 does not impede the general proteasome-mediated protein degradation process, but it does raise cellular A3G levels in a Vif-dependent manner and increase A3G incorporation into virions. Only in the presence of A3G does RN-18 increase Vif degradation; it also increases cytidine deamination of the viral genome, decreases viral infectivity by increasing A3G incorporation into virions[2].
References	[1]. SAR and Lead Optimization of an HIV-1 Vif-APOBEC3G Axis Inhibitor. ACS Med Chem Lett. 2012 Jun 14;3(6):465-469. [2]. Small-molecule inhibition of HIV-1 Vif. Nat Biotechnol. 2008 Oct;26(10):1187-92.

Solubility Data

Solubility (In Vitro)

DMSO : ~100 mg/mL (~262.87 mM)

Solubility (In Vivo)

Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples. Injection Formulations (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] *Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Oral Formulations Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	2.6287 mL	13.1434 mL	26.2867 mL
	5 mM	0.5257 mL	2.6287 mL	5.2573 mL
	10 mM	0.2629 mL	1.3143 mL	2.6287 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.