CAS Number64224-21-1
SynonymsOltipraz; 4-methyl-5-pyrazin-2-yldithiole-3-thione; RP-35,972; 4-Methyl-5-(pyrazin-2-yl)-3H-1,2-dithiole-3-thione; 4-Methyl-5-(2-pyrazinyl)-3H-1,2-dithiole-3-thione; 4-Methyl-5-pyrazinyl-3H-1,2-dithiole-3-thione; 3H-1,2-DITHIOLE-3-THIONE,4-METHYL-5-PYRAZINYL; 4-Methyl-5-pyrazin-2-yl-1,2-dithiole-3-thione
Molecular FormulaC8H6N2S3
Molecular Weight226.34
Purity≥98 (HPLC)%
Density1.5±0.1 g/cm3
Boiling Point408.1±55.0 °C at 760 mmHg
Melting Point165-166ºC
Appearancepowder
EINECS264-736-6
Symbol
Signal WordWarning
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 64224-21-1 |
| Catalog No. | 2A-9011766 |
| Chinese Name | 吡噻硫酮 |
| Synonyms | Oltipraz; 4-methyl-5-pyrazin-2-yldithiole-3-thione; RP-35,972; 4-Methyl-5-(pyrazin-2-yl)-3H-1,2-dithiole-3-thione; 4-Methyl-5-(2-pyrazinyl)-3H-1,2-dithiole-3-thione; 4-Methyl-5-pyrazinyl-3H-1,2-dithiole-3-thione; 3H-1,2-DITHIOLE-3-THIONE,4-METHYL-5-PYRAZINYL; 4-Methyl-5-pyrazin-2-yl-1,2-dithiole-3-thione |
| Molecular Formula | C8H6N2S3 |
| Molecular Weight | 226.34 |
| Purity | ≥98 (HPLC) |
| Density | 1.5±0.1 g/cm3 |
| Boiling Point | 408.1±55.0 °C at 760 mmHg |
| Melting Point | 165-166ºC |
| Appearance | powder |
| Storage Condition | 2-8°C |
| Application | Oltipraz inhibits HIF-1α activation. This effect is time-dependent. HIF-1α induction is completely abolished when the concentration is ≥10 μM. Oltipraz inhibits HIF-1α with an IC50 of 10 μM. |
| EINECS | 264-736-6 |
| HTC | 2933990090 |
| PubChem ID | 329818939 |
| MDL Number | MFCD00868499 |
| SMILES | CC1=C(SSC1=S)c2cnccn2 |
| InChI | 1S/C8H6N2S3/c1-5-7(12-13-8(5)11)6-4-9-2-3-10-6/h2-4H,1H3 |
| InChI Key | CKNAQFVBEHDJQV-UHFFFAOYSA-N |
| NACRES Code | NA.77 |
| UNSPSC | 12352200 |
| Hazard Symbols | Transport |
| MSDS | msds/11766_1_64224_21_1.pdf |
| Bioactivity | Oltipraz has an inhibitory effect on HIF-1α activation by insulin in a time-dependent manner, completely abrogating HIF-1α induction at ≥10 μM concentrations, the IC50 of Oltipraz for HIF-1α inhibition is 10 μM.IC50 value: 10 μMTarget: HIF-1αin vitro: Oltipraz inhibits HIF-1α activity and HIF-1α-dependent tumor growth, which may result from a decrease in HIF-1α stability through S6K1 inhibition in combination with an H2O2-scavenging effect. Oltipraz treatment also inhibits HIF-1α activation stimulated by either hypoxia or CoCl2. Oltipraz is a cancer chemopreventive agent and has an inhibitory effect on angiogenesis and tumor growth. [1] Oltipraz is also a competitive inhibitor of this cytochrome P450, with an apparent Ki of 10 μM. [2]in vivo: In wild-type mice, hepatic levels of mRNA for all of the genes analyzed were significantly increased after Oltipraz treatment, with the highest increase (treated/control) for NQO1 mRNA levels (7.6-fold). The Northern blot analyses demonstrated that the observed increases in GST and NQO1 activities by Oltipraz in wild-type mice were preceded by significant elevations in RNA expression. Interestingly, mRNA levels of Nrf2 itself were increased more than 3-fold by Oltipraz treatment. [2] Related Catalog Signaling Pathways >> Metabolic Enzyme/Protease >> HIF/HIF Prolyl-Hydroxylase Research Areas >> Cancer References [1]. Lee WH, et al. Oltipraz and dithiolethione congeners inhibit hypoxia-inducible factor-1alpha activity through p70 ribosomal S6 kinase-1 inhibition and H2O2-scavenging effect. Mol Cancer Ther. 2009 Oct;8(10):2791-802. [2]. Ramos-Gomez M, et al. Sensitivity to carcinogenesis is increased and chemoprotective efficacy of enzyme inducers is lost in nrf2 transcription factor-deficient mice. Proc Natl Acad Sci U S A. 2001 Mar 13;98(6):3410-5. [3]. Lv S, et al. Glucagon-induced extracellular cAMP regulates hepatic lipid metabolism. J Endocrinol. 2017 Aug;234(2):73-87. Chemical & Physical Properties Density 1.5±0.1 g/cm3 Boiling Point 408.1±55.0 °C at 760 mmHg Melting Point 165-166ºC Molecular Formula C8H6N2S3 Molecular Weight 226.342 Flash Point 200.6±31.5 °C Exact Mass 225.969315 PSA 114.35000 LogP 1.92 Vapour Pressure 0.0±0.9 mmHg at 25°C Index of Refraction 1.760 InChIKey CKNAQFVBEHDJQV-UHFFFAOYSA-N SMILES Cc1c(-c2cnccn2)ssc1=S Storage condition 2-8°C |
| Use of | Properties Articles35 Name oltipraz Synonym More Synonyms Oltipraz Biological Activity Related Catalog Signaling Pathways >> Metabolic Enzyme/Protease >> HIF/HIF Prolyl-Hydroxylase Research Areas >> Cancer References [1]. Lee WH, et al. Oltipraz and dithiolethione congeners inhibit hypoxia-inducible factor-1alpha activity through p70 ribosomal S6 kinase-1 inhibition and H2O2-scavenging effect. Mol Cancer Ther. 2009 Oct;8(10):2791-802. [2]. Ramos-Gomez M, et al. Sensitivity to carcinogenesis is increased and chemoprotective efficacy of enzyme inducers is lost in nrf2 transcription factor-deficient mice. Proc Natl Acad Sci U S A. 2001 Mar 13;98(6):3410-5. [3]. Lv S, et al. Glucagon-induced extracellular cAMP regulates hepatic lipid metabolism. J Endocrinol. 2017 Aug;234(2):73-87. Chemical & Physical Properties Molecular Formula C8H6N2S3 Exact Mass 225.969315 PSA 114.35000 Index of Refraction 1.760 InChIKey CKNAQFVBEHDJQV-UHFFFAOYSA-N |
| Tax Rebate | 13.0% |
| Supervision | None. MFN tariff: 6.5%. Ordinary tariff: 20.0% |
| Transport Info | Product name: Purity: 98.0% |
| MSDS Transport Info | Module 14. Shipping information 14.1 UN dangerous goods number European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.2 Names specified by the United Nations (UN) European Land Transport Dangerous Regulations: Non-dangerous goods IMDG Code: Non-dangerous goods International air transport dangerous goods regulations: non-dangerous goods 14.3 Transport hazard categories European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.4 Package group European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.5 Environmental hazards European Land Transport Dangerous Regulations: No International Maritime Transport Dangerous Regulations Maritime Pollutants: No International Air Transport Risk Regulations: No 14.6 Special reminder to users No data available |
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