![4-amino-N-[(2R,3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-(2-methylpropyl)benzenesulfonamide](/upload/0290/8ef44808-c5be-4d47-8fa8-7ba309d378f0.png)
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| Targets |
This compound is a synthetic intermediate for darunavir, which targets the HIV-1 protease enzyme. Darunavir inhibits HIV-1 protease, preventing the cleavage of viral polyproteins and thereby inhibiting viral replication. The compound itself does not have direct biological activity but serves as a precursor to the active pharmaceutical ingredient.
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| ln Vitro |
In vitro, this compound is used as a building block for the synthesis of darunavir. Darunavir has been shown to be a potent HIV-1 protease inhibitor with activity against wild-type and drug-resistant HIV strains. The intermediate's stereochemistry is critical for the biological activity of the final drug product.
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| ln Vivo |
In vivo, darunavir synthesized from this intermediate is used as an antiretroviral drug for the treatment of HIV infection. Darunavir is a potent HIV-1 protease inhibitor that reduces viral load and increases CD4 cell counts in HIV-infected patients. It is used in combination with other antiretroviral agents.
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| Enzyme Assay |
For synthesis applications, the compound is used as a starting material for the preparation of darunavir. The sulfonamide and amino groups undergo further chemical transformations to form the final drug molecule. Reactions are carried out in organic solvents with appropriate reagents and catalysts.
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| Cell Assay |
For cell-based studies, darunavir synthesized from this intermediate is evaluated in HIV-infected cell lines. Cells are cultured in DMEM or RPMI-1640 with 10% FBS at 37°C in 5% CO₂. Cells are infected with HIV and treated with darunavir at 0.1-100 µM for 24-72 hours. Viral replication is measured by p24 antigen ELISA or RT-PCR.
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| Animal Protocol |
For in vivo studies, darunavir is formulated in suitable vehicles and administered orally to HIV-infected animal models or healthy subjects. Pharmacokinetic studies determine compound exposure and half-life. Efficacy is evaluated by measuring viral load reduction. Toxicity is monitored by body weight and clinical observations.
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| ADME/Pharmacokinetics |
4-amino-N-[(2R,3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-(2-methylpropyl)benzenesulfonamide has a molecular weight of 391.5 g/mol and a molecular formula of C₂₀H₂₉N₃O₃S. It has a PubChem CID of 9888792. It is typically stored as a solid at room temperature. It is soluble in organic solvents such as DMSO. Purity is typically ≥97%.
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| Toxicity/Toxicokinetics |
Acute toxicity data for this intermediate are limited. Standard laboratory safety practices should be followed. The compound may cause skin and eye irritation upon contact. Proper personal protective equipment should be used. Long-term toxicity studies have been conducted on darunavir, not on this intermediate.
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| Additional Infomation |
This compound is also known as Darunavir Intermediate 3. It is a key intermediate in the synthesis of darunavir, an HIV-1 protease inhibitor used for the treatment of HIV infection. The stereochemistry is critical for the biological activity of the final drug product. It is a research intermediate and is not a therapeutic agent itself.
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| Molecular Formula |
C20H29N3O3S
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| Molecular Weight |
391.5
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| Exact Mass |
391.193
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| CAS # |
169280-56-2
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| PubChem CID |
9888792
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| Appearance |
Typically exists as solids at room temperature
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| Density |
1.2±0.1 g/cm3
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| Boiling Point |
609.1±65.0 °C at 760 mmHg
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| Flash Point |
322.2±34.3 °C
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| Vapour Pressure |
0.0±1.8 mmHg at 25°C
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| Index of Refraction |
1.605
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| LogP |
3.79
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| Hydrogen Bond Donor Count |
3
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| Hydrogen Bond Acceptor Count |
6
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| Rotatable Bond Count |
9
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| Heavy Atom Count |
27
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| Complexity |
521
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| Defined Atom Stereocenter Count |
2
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| SMILES |
CC(C)CN(C[C@H]([C@H](CC1=CC=CC=C1)N)O)S(=O)(=O)C2=CC=C(C=C2)N
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| InChi Key |
NUMJNKDUHFCFJO-VQTJNVASSA-N
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| InChi Code |
InChI=1S/C20H29N3O3S/c1-15(2)13-23(27(25,26)18-10-8-17(21)9-11-18)14-20(24)19(22)12-16-6-4-3-5-7-16/h3-11,15,19-20,24H,12-14,21-22H2,1-2H3/t19-,20+/m0/s1
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| Chemical Name |
4-amino-N-[(2R,3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-(2-methylpropyl)benzenesulfonamide
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| HS Tariff Code |
2934.99.9001
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| 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)
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| Solubility (In Vitro) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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| 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
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *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). View More
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)] 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). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.5543 mL | 12.7714 mL | 25.5428 mL | |
| 5 mM | 0.5109 mL | 2.5543 mL | 5.1086 mL | |
| 10 mM | 0.2554 mL | 1.2771 mL | 2.5543 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.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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