| Size | Price | Stock | Qty |
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| Targets |
Goitrin primarily targets thyroid peroxidase, an enzyme essential for thyroid hormone synthesis. By inhibiting this enzyme, goitrin blocks the utilization of iodine by the thyroid, leading to antithyroid effects. Goitrin also exhibits antiviral activity against influenza virus A (H1N1) and anticancer properties. The compound has a molecular weight of 129.18 g/mol and a molecular formula of C₅H₇NOS. It behaves as a weak acid with a pKa of 10.5.
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| ln Vitro |
In Madin-Darby canine kidney (MDCK) cells, goitrin (0.1–1 μM; 72 h) demonstrates dose-dependent anti–influenza virus (H1N1) action, with an IC50 of 0.19 μM[3].
In vitro, Goitrin demonstrates potent inhibition of thyroid peroxidase, blocking iodine utilization by the thyroid. It exhibits antiviral activity against influenza virus A (H1N1) with virucidal effects. The compound also shows anticancer activity. In cell-based assays, goitrin influences oxidative and immune regulation, enabling analysis of host responses shaping viral susceptibility. These activities support its use in studying thyroid function, viral infections, and cancer. |
| ln Vivo |
In vivo data for goitrin is primarily derived from its antithyroid effects in animal models. As a thyroid peroxidase inhibitor, goitrin reduces thyroid hormone production in vivo. The compound's antiviral activity against influenza virus A (H1N1) has been demonstrated in ovo (chicken eggs). However, specific published in vivo efficacy studies in mammalian models are not detailed in the available literature. Goitrin is primarily used as a research tool for studying thyroid function and antiviral mechanisms.
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| Enzyme Assay |
The in vitro thyroid peroxidase inhibition assay for goitrin uses purified thyroid peroxidase enzyme and a substrate such as iodide or guaiacol. Enzyme activity is measured by monitoring the oxidation of the substrate, and IC50 values are calculated from dose-response curves. Antiviral assays are performed in cell lines infected with influenza virus A (H1N1), with viral replication measured by plaque assay or quantitative PCR. The compound's effects on iodine utilization are assessed using thyroid cell cultures.
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| Cell Assay |
Cellular assays for goitrin are conducted in thyroid cell lines to assess its effects on iodide uptake and thyroid peroxidase activity. Cells are treated with varying concentrations of the compound, and iodide uptake is measured using radioactive iodide or fluorescence-based methods. Antiviral assays are performed in influenza virus-infected cells. Cell viability is assessed to confirm that effects are not due to cytotoxicity. The compound's influence on oxidative and immune regulation is evaluated in immune cell models.
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| Animal Protocol |
In vivo studies for goitrin would typically involve animal models of thyroid dysfunction or influenza virus infection. For thyroid studies, the compound would be administered orally or via injection, and thyroid hormone levels would be measured in serum. For antiviral studies, animals would be challenged with influenza virus and treated with goitrin, with efficacy assessed by measuring viral loads and survival. However, specific published in vivo protocols for goitrin are not detailed in the available literature.
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| ADME/Pharmacokinetics |
Absorption, Distribution and Excretion
Six dairy cows were selected and divided into three groups. They were fed rapeseed meal containing 6 g/kg of goitrogen for seven days. The cows were milked twice daily… When the rapeseed meal content was 0.39%, 1.9%, and 3.9% of the total feed, the average goitrogen content in the milk was 37, 163, and 707 μg/L, respectively. These values represent approximately 0.1% of the proto-goitrogen in the feed transferred to the milk. Twelve hours after the last rapeseed meal feeding, the goitrogen content in the milk was below the detection limit of 7 ppb. Pharmacokinetic data for goitrin is not extensively reported in publicly available sources. The compound has a molecular weight of 129.18 g/mol and is stable in alkali but not in acid. It has an optical rotation of [α]D31 -70.5° (c = 2 in methanol). As a small molecule, it is expected to have good oral absorption. Detailed PK parameters such as half-life and bioavailability are not available in the current literature for this compound. |
| Toxicity/Toxicokinetics |
Interactions
Goitrin is a potent goitrogenic substance that has been shown to induce glutathione S-transferase (GST) activity and enhance the detoxification effect of aflatoxin. Goitrin—a compound naturally found in cruciferous vegetables and rapeseed—is readily nitrified by nitrite under gastric conditions, losing sulfur to form N-nitroso-oxazolidinone 4. Its mutagenic pattern and potency in the Ames Salmonella/mammalian microsomal assay are similar to those of N-nitroso-N-methyl-N'-nitroguanidine (MNNG). Toxicity data for goitrin is derived from its antithyroid effects. As a thyroid peroxidase inhibitor, goitrin can cause hypothyroidism and goiter at high doses. The compound's use as an antithyroid agent indicates that it can have significant endocrine effects. As with all research compounds, goitrin is intended for research use only and not for human therapeutic applications without proper medical supervision. |
| References |
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| Additional Infomation |
(S)-Goitrin is a 5-vinyl-1,3-oxazolidine-2-thione with an S configuration. It is one of the components of the traditional Chinese medicine Isatis indigotica. It has antiviral, phytometabolic, and antithyroid effects. It is the enantiomer of (R)-goitrin. Goitrin has also been reported in cabbage, Chinese kale, and other organisms with relevant data. Mechanism of Action: Various chemicals, drugs, and other exogenous substances can affect the second step of thyroid hormone biosynthesis. The stepwise binding of iodides to tyrosine residues in thyroglobulin requires thyroid peroxidase to oxidize inorganic iodine (I₂) to molecular (active) iodine (I₂), a process that occurs on the luminal surface of follicular cells (microvilli) and in adjacent glial tissue. Chemicals that inhibit the organification of thyroglobulin include…thionamide drugs (e.g., goitrin)…
Goitrin ((S)-Goitrin) is a sulfur-containing alkaloid isolated from Isatis indigotica (Ban Lan Gen) and Brassica vegetables. It is a potent thyroid peroxidase inhibitor that blocks iodine utilization by the thyroid. Goitrin also exhibits antiviral activity against influenza virus A (H1N1) and anticancer properties. It has a molecular weight of 129.18 g/mol and a molecular formula of C₅H₇NOS. The compound is used as a research tool for studying thyroid function, viral infections, and anticancer mechanisms. |
| Molecular Formula |
C5H7NOS
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| Molecular Weight |
129.18
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| Exact Mass |
129.025
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| CAS # |
500-12-9
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| Related CAS # |
Epigoitrin;1072-93-1
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| PubChem CID |
7568320
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| Appearance |
Large prisms from ether
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| Melting Point |
50 °C
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| LogP |
0.774
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
2
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| Rotatable Bond Count |
1
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| Heavy Atom Count |
8
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| Complexity |
124
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| Defined Atom Stereocenter Count |
1
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| SMILES |
C=CC1CNC(=S)O1
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| InChi Key |
UZQVYLOFLQICCT-BYPYZUCNSA-N
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| InChi Code |
InChI=1S/C5H7NOS/c1-2-4-3-6-5(8)7-4/h2,4H,1,3H2,(H,6,8)/t4-/m0/s1
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| Chemical Name |
(5S)-5-ethenyl-1,3-oxazolidine-2-thione
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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 | 7.7411 mL | 38.7057 mL | 77.4114 mL | |
| 5 mM | 1.5482 mL | 7.7411 mL | 15.4823 mL | |
| 10 mM | 0.7741 mL | 3.8706 mL | 7.7411 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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