| Size | Price | Stock | Qty |
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| 100mg |
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| Other Sizes |
| Targets |
Azulene targets HIV protease and exhibits anti-HIV activity. It also inhibits alpha-chymotrypsin, with a log1/Ki value of 4.21. The compound shows antiretroviral activity against HIV-1 based virus-like particles in U2OS cells. Additionally, Azulene has anti-inflammatory properties. These targets make it a valuable scaffold in antiviral and medicinal chemistry research.
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| ln Vitro |
Because it resembles a number of other bicyclic aromatic compounds that are frequently found in pharmaceuticals, the azulene ring is an intriguing scaffold in medicinal chemistry. The structural isomer of naphthalene, chamomilene, is a bicyclic aromatic hydrocarbon that is non-benzene and has a dipole moment because of two different rings: one with seven electrons deficient and the other with five electrons abundant [1].
In vitro, Azulene demonstrates high anti-HIV activity as an isomer of naphthalene. It inhibits alpha-chymotrypsin with a log1/Ki value of 4.21. The compound possesses antiretroviral activity against HIV-1 based virus-like particles in U2OS cells, achieving 76.0% activity. These in vitro activities confirm its potential as an antiviral agent. Azulene is also studied for its anti-inflammatory properties in cell-based assays. The compound serves as a scaffold for developing new bioactive molecules. |
| ln Vivo |
In vivo, Azulene has demonstrated anti-inflammatory effects, as it is classified as an anti-inflammatory agent in some regulatory contexts. It is used in over-the-counter (OTC) products in some regions. However, detailed in vivo efficacy data for its antiviral activity are limited. The compound's aromatic stability makes it suitable for studying hydrocarbon frameworks in antiviral design. Further in vivo studies are needed to fully characterize its therapeutic potential and mechanisms of action.
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| Enzyme Assay |
In vitro enzyme/receptor binding assays for Azulene include alpha-chymotrypsin inhibition assays, where the compound's inhibitory activity is measured using chromogenic substrates. The log1/Ki value is determined to be 4.21. Anti-HIV activity is assessed using cell-based assays with HIV-1 based virus-like particles in U2OS cells, measuring inhibition of viral replication at various concentrations. Binding to HIV protease can be assessed using fluorescence-based or calorimetric assays. All assays include appropriate controls and reference compounds (e.g., known protease inhibitors).
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| Cell Assay |
In vitro cell-based assays for Azulene are conducted using U2OS cells infected with HIV-1 based virus-like particles. Cells are treated with Azulene at concentrations ranging from 0.1-100 μM for 24-72 hours. Antiretroviral activity is measured by quantifying viral replication or reporter gene expression. Cell viability is assessed using MTT or similar assays to distinguish antiviral effects from cytotoxicity. Anti-inflammatory activity is evaluated in macrophage or other inflammatory cell models by measuring cytokine production. All experiments include vehicle controls and positive controls (e.g., known antiviral agents).
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| Animal Protocol |
In vivo animal studies with Azulene are limited, as the compound is primarily used as a research scaffold and in topical OTC products. Topical anti-inflammatory studies may be conducted in animal models of skin inflammation. The compound is applied topically at concentrations of 0.1-5% in appropriate formulations. Inflammation is assessed by measuring edema, erythema, or histopathological changes. Systemic administration studies for antiviral efficacy are less common. Each group consists of 6-10 animals with appropriate vehicle controls.
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| ADME/Pharmacokinetics |
Metabolism / Metabolites
The metabolism of polycyclic aromatic hydrocarbons (PAHs) occurs in all tissues and is typically catalyzed by cytochrome P-450 and its associated enzymes. PAH metabolism produces reactive intermediates, including epoxide intermediates, dihydrodiols, phenols, quinones, and various combinations thereof. Phenols, quinones, and dihydrodiols can all bind to glucuronides and sulfates; quinones can also bind to glutathione. (L10) Pharmacokinetic properties of Azulene include its lipophilic nature (MW 128.17), which allows for good skin penetration and topical bioavailability. Following topical application, the compound is absorbed through the skin and may enter systemic circulation. Oral bioavailability is expected to be moderate due to its lipophilic character. Metabolism likely occurs through hepatic cytochrome P450 enzymes, with elimination via biliary and renal excretion. Detailed PK parameters such as half-life and bioavailability require further characterization in preclinical studies. |
| Toxicity/Toxicokinetics |
Toxicity Summary
Polycyclic aromatic hydrocarbons (PAHs) can bind to blood proteins such as albumin, thereby facilitating their transport in the body. Many PAHs induce the expression of cytochrome P450 enzymes, particularly CYP1A1, CYP1A2, and CYP1B1, by binding to aryl hydrocarbon receptors or glycine N-methyltransferases. These enzymes metabolize PAHs into their toxic intermediates. The active metabolites of PAHs (epoxide intermediates, dihydrodiols, phenols, quinones, and various combinations thereof) covalently bind to DNA and other cellular macromolecules, inducing mutagenic and carcinogenic effects. (L10, L23, A27, A32) Toxicity Data LD50: >4000 mg/kg (oral, rat) (L912) LD50: 180 mg/kg (intraperitoneal, rat) (L912) LD50: 520 mg/kg (subcutaneous, rat) (L912) Toxicological data for Azulene indicate that it is generally well-tolerated at concentrations used in topical OTC products. It is classified as a third-class OTC drug in some regions, indicating a favorable safety profile for topical use. No significant systemic toxicity has been reported at typical exposure levels. However, comprehensive toxicological studies, including chronic toxicity and genotoxicity, are limited. As with all research chemicals, appropriate safety precautions should be taken during handling. |
| References | |
| Additional Infomation |
Azurite is a carbon-containing bicyclic parent compound composed of cycloheptatriene and cyclopentadiene rings. It is a plant metabolite and volatile oil component. It is an ortho-fused bicyclic aromatic hydrocarbon, belonging to the azurite class of compounds, and is also a carbon-containing bicyclic parent compound. Azurite has been reported to exist in Achillea asiatica, Basella alba, and several other organisms with relevant data. Azurite is one of more than 100 polycyclic aromatic hydrocarbons (PAHs). PAHs are chemical substances formed during the incomplete combustion of organic matter such as fossil fuels. They usually exist as mixtures of two or more compounds. (L10)
Azulene is a naturally occurring hydrocarbon with significant research applications in medicinal chemistry and antiviral drug discovery. It is isolated from chamomile oil and serves as a scaffold for developing new bioactive molecules. The compound's anti-HIV activity makes it relevant for antiviral research. It is also used in some OTC products as an anti-inflammatory agent. Azulene is not approved as a prescription therapeutic agent but is used in topical formulations in some regions. Intended for research purposes. |
| Molecular Formula |
C10H8
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|---|---|
| Molecular Weight |
128.17
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| Exact Mass |
128.062
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| CAS # |
275-51-4
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| Related CAS # |
82451-56-7
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| PubChem CID |
9231
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| Appearance |
Purple to blue solid powder
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| Density |
1.0±0.1 g/cm3
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| Boiling Point |
220.7±7.0 °C at 760 mmHg
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| Melting Point |
98-100 °C(lit.)
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| Flash Point |
76.7±8.9 °C
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| Vapour Pressure |
0.2±0.2 mmHg at 25°C
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| Index of Refraction |
1.632
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| LogP |
3.45
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
0
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| Rotatable Bond Count |
0
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| Heavy Atom Count |
10
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| Complexity |
94.6
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| Defined Atom Stereocenter Count |
0
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| InChi Key |
CUFNKYGDVFVPHO-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C10H8/c1-2-5-9-7-4-8-10(9)6-3-1/h1-8H
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| Chemical Name |
azulene
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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) |
DMSO : ~100 mg/mL (~780.21 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (19.51 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (19.51 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. 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. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (19.51 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 7.8021 mL | 39.0107 mL | 78.0214 mL | |
| 5 mM | 1.5604 mL | 7.8021 mL | 15.6043 mL | |
| 10 mM | 0.7802 mL | 3.9011 mL | 7.8021 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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