Zileuton
- Iupac Name：1-[1-(1-benzothiophen-2-yl)ethyl]-1-hydroxyurea
- CAS No.: 111406-87-2
- Molecular Weight：236.29000
- Modify Date.: 2022-11-06 04:48
- Introduction: Zileuton, a benzothiophene N-hydroxyurea, is the only approved inhibitor of 5-lipoxygenase. It is believed to intervene with allergic and inflammatory diseases by suppression of leukotriene (LT) biosynthesis. The compound belongs to the class of iron ligand-type inhibitors of 5-lipoxygenase that not only chelates the active site iron of the enzyme but also possesses weak-reducing properties.Zileuton is used as a type of drug for the prophylaxis and chronic treatment of asthma.
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1. Names and Identifiers
- 1.1 Name
- Zileuton
- 1.2 Synonyms
(±)-N-hydroxy-N-(1-benzo[b]thien-2-ylethyl)urea 1-(1-(Benzo[b]thiophen-2-yl)ethyl)-1-hydroxyurea 1-(1-benzo[b]thien-2-ylethyl)-1-hydroxyurea 1-[1-(1-Benzothiophen-2-yl)ethyl]-1-hydroxyurea Leutml Leutrol MFCD00866097 N-hydroxy-N-{1-(benzo[b]thien-2-yl)ethyl}urea Urea, N-(1-benzo[b]thien-2-ylethyl)-N-hydroxy- Zyfl Zyflo
- 1.3 CAS No.
- 111406-87-2
- 1.4 CID
- 60490
- 1.5 EINECS(EC#)
- 601-087-3
- 1.6 Molecular Formula
- C11H12N2O2S (isomer)
- 1.7 Inchi
- InChI=1S/C11H12N2O2S/c1-7(13(15)11(12)14)10-6-8-4-2-3-5-9(8)16-10/h2-7,15H,1H3,(H2,12,14)
- 1.8 InChkey
- MWLSOWXNZPKENC-UHFFFAOYSA-N
- 1.9 Canonical Smiles
- CC(C1=CC2=CC=CC=C2S1)N(C(=O)N)O
- 1.10 Isomers Smiles
- CC(C1=CC2=CC=CC=C2S1)N(C(=O)N)O
2. Properties
- 2.1 Density
- 1.401 g/cm3
- 2.1 Melting point
- 157-158°C
- 2.1 Boiling point
- 449.4ºC at 760 mmHg
- 2.1 Refractive index
- 1.704
- 2.1 Flash Point
- 225.6ºC
- 2.1 Precise Quality
- 236.06200
- 2.1 PSA
- 94.80000
- 2.1 logP
- 3.43250
- 2.1 Solubility
- DMSO: ≥20mg/mL at ~60°C (warm up to 60 C for 5min)
- 2.2 Appearance
- crystalline solid
- 2.3 Storage
- Store at +4°C
- 2.4 Chemical Properties
- Crystalline Solid
- 2.5 Color/Form
- Powder
- 2.6 pKa
- pKa 10.3(H2Ot undefinedI undefined) (Uncertain)
- 2.7 Water Solubility
- Insoluble
- 2.8 StorageTemp
- Store in original container in a cool dark place.
3. Use and Manufacturing
- 3.1 Definition
- ChEBI: A member of the class of 1-benzothiophenes that is 1-benzothiophene in which the hydrogen at position 2 is replaced by a 1-[carbamoyl(hydroxy)amino]ethyl group. A selective 5-lipoxygenase inhibitor, it inhibits the formation of leukotrienes LTB4, LTC4, LDT, and LTE4. It is used for the management of chronic asthma.
- 3.2 Usage
- An inhibitor of 5-lipoxygenase, the initial enzyme in the biosynthesis of leukotrienes from Arachidonic Acid. Used as an antiasthmatic
4. Safety and Handling
- 4.1 Symbol
- GHS07
- 4.1 Hazard Codes
- Xi
- 4.1 Signal Word
- Warning
- 4.1 Risk Statements
- 22-36
- 4.1 Safety Statements
- 26
- 4.1 Hazard Declaration
- H302-H319
- 4.1 RIDADR
- NONH for all modes of transport
- 4.1 Caution Statement
- P305 + P351 + P338
- 4.1 WGK Germany
- 3
- 4.1 Specification
-
?Zileuton (CAS NO.111406-87-2) is also named as (+-)-1-(1-Benzo(b)thien-2-ylethyl)-1-hydroxyurea ; A 64077 ; Abbott 64077 ; Leutrol ; N-(1-Benzo(b)thien-2-ylethyl)-N-hydroxyurea ; UNII-V1L22WVE2S ; Urea, N-(1-benzo(b)thien-2-ylethyl)-N-hydroxy-, (+-)- ; Zileutonum ; Zileutonum [INN-Latin] ; Zyflo ; Zyflo CR .
5. MSDS
2.Hazard identification
2.1 Classification of the substance or mixture
Acute toxicity - Oral, Category 4
Eye irritation, Category 2
2.2 GHS label elements, including precautionary statements
| Pictogram(s) |  |
| Signal word | Warning |
| Hazard statement(s) | H302 Harmful if swallowed H319 Causes serious eye irritation |
| Precautionary statement(s) | |
| Prevention | P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product. P280 Wear protective gloves/protective clothing/eye protection/face protection. |
| Response | P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/\u2026if you feel unwell. P330 Rinse mouth. P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P337+P313 If eye irritation persists: Get medical advice/attention. |
| Storage | none |
| Disposal | P501 Dispose of contents/container to ... |
2.3 Other hazards which do not result in classification
none
6. Other Information
- 6.0 Description
- Zileuton, a benzothiophene N-hydroxyurea, is the only approved inhibitor of 5-lipoxygenase. It is believed to intervene with allergic and inflammatory diseases by suppression of leukotriene (LT) biosynthesis. The compound belongs to the class of iron ligand-type inhibitors of 5-lipoxygenase that not only chelates the active site iron of the enzyme but also possesses weak-reducing properties.
Zileuton is used as a type of drug for the prophylaxis and chronic treatment of asthma.
- 6.1 References
- [1] A Rossi, C Pergola, A Koeberle, M Hoffmann, F Dehm, P Bramanti, S Cuzzocrea, O Werz and L Sautebin, The 5-lipoxygenase inhibitor, zileuton, suppresses prostaglandin biosynthesis by inhibition of arachidonic acid release in macrophages, British Journal of Pharmacology, 2010, col. 161, 555-570
[2] SE Wenzel and AK Kamada, Zileuton: the first 5-lipoxygenase inhibitor for the treatment of asthma, Ann Pharmacother., 1996, vol. 30, 858-864
- 6.2 Chemical Properties
- Crystalline Solid
- 6.3 Uses
- An inhibitor of 5-lipoxygenase, the initial enzyme in the biosynthesis of leukotrienes from Arachidonic Acid. Used as an antiasthmatic
- 6.4 Uses
- gastric acid secretion inhibitor
- 6.5 Definition
- ChEBI: A member of the class of 1-benzothiophenes that is 1-benzothiophene in which the hydrogen at position 2 is replaced by a 1-[carbamoyl(hydroxy)amino]ethyl group. A selective 5-lipoxygenase inhibitor, it inhibits the formation of leukotrienes LTB4, LTC4, LDT , and LTE4. It is used for the management of chronic asthma.
- 6.6 Brand name
- Zyflo (Sensus).
7. Computational chemical data
- Molecular Weight: 236.29000g/mol
- Molecular Formula: C11H12N2O2S
- Compound Is Canonicalized: True
- XLogP3-AA: 1.6
- Exact Mass: 236.06194880
- Monoisotopic Mass: 236.06194880
- Complexity: 275
- Rotatable Bond Count: 2
- Hydrogen Bond Donor Count: 2
- Hydrogen Bond Acceptor Count: 3
- Topological Polar Surface Area: 94.8
- Heavy Atom Count: 16
- Defined Atom Stereocenter Count: 0
- Undefined Atom Stereocenter Count: 1
- Defined Bond Stereocenter Count: 0
- Undefined Bond Stereocenter Count: 0
- Isotope Atom Count: 0
- Covalently-Bonded Unit Count: 1
- CACTVS Substructure Key Fingerprint: AAADccBzMABAAAAAAAAAAAAAAAAAASAAAAAwAAAAAAAAAEgB8AAAHgQUCAAADCjBWAQzAcJQAAiMAiBCEACDAIAgCBBoiBgIBIiIICKgkRGEIAhghgIoiAcQgIAOAAAAAAAEAAAAAAAAAAgAAAAAAAAAAA==
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- Purity:99%Packing: 200kg/bag FOB
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- Time: 2023/04/27
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- Purity:99%Packing: 200kg/bag FOB
- Price: 100 USD/gram
- Time: 2023/05/30
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9. Realated Product Infomation
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