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Ebselen

Ebselen structure

CAS No:
60940-34-3
Formula:
C13H9NOSe
Chemical Name:
Ebselen
Synonyms:
1,2-Benzisoselenazol-3(2H)-one,2-phenyl-;2-Phenyl-1,2-benzisoselenazol-3(2H)-one;PZ 51;Ebselen;2-Phenyl-1,2-benzoisoselenazol-3(2H)-one;NSC 639762;Lopac E 3520;CCG-39161;DR 3305;SPI 1005;2-Phenyl-1,2-benzoselenazol-3-one;2-Phenylbenzo[d][1,2]selenazol-3(2H)-one
Categories:
Organic Chemistry > Organoselenium Compounds

Description

Ebselen is a small-molecule capsid Inhibitor of HIV-1 replication.Target:Ebselen is an organoselenium compound, as an inhibitor of HIV-1 capsid CTD dimerization. Ebselen inhibits early viral postentry events of the HIV-1 life cycle by impairing the incoming capsid uncoating process. [1] Ebselen is a non-toxic seleno-organic drug with anti-inflammatory and antioxidant properties. Ebselen is an inhibitor of inositol monophosphatase (IMPase). Ebselen permeates the blood-brain barrier and in

Ebselen is a benzoselenazole that is 1,2-benzoselenazol-3-one carrying an additional phenyl substituent at position 2. Acts as a mimic of glutathione peroxidase. It has a role as a neuroprotective agent, an apoptosis inducer, an anti-inflammatory drug, an antioxidant, a hepatoprotective agent, a genotoxin, a radical scavenger, an enzyme mimic, an EC 1.3.1.8 [acyl-CoA dehydrogenase (NADP(+))] inhibitor, an EC 1.8.1.12 (trypanothione-disulfide reductase) inhibitor, an EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor, an EC 1.13.11.34 (arachidonate 5-lipoxygenase) inhibitor, an EC 2.5.1.7 (UDP-N-acetylglucosamine 1-carboxyvinyltransferase) inhibitor, an EC 2.7.10.1 (receptor protein-tyrosine kinase) inhibitor, an EC 3.5.4.1 (cytosine deaminase) inhibitor, an EC 5.1.3.2 (UDP-glucose 4-epimerase) inhibitor, a ferroptosis inhibitor, an antifungal agent, an EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor, an anticoronaviral agent, an antibacterial agent, an antineoplastic agent and an EC 3.1.3.25 (inositol-phosphate phosphatase) inhibitor.|Ebselen has been investigated for the treatment and basic science of Meniere's Disease, Type 2 Diabetes Mellitus, and Type 1 Diabetes Mellitus.|Ebselen is a organoselenium compound with anti-inflammatory, anti-oxidant and cytoprotective activity. Ebselen acts as a glutathione peroxidase mimetic and is thereby able to prevent cellular damage induced by reactive oxygen species (ROS). In addition, this agent inhibits the activity of a variety of enzymes including nitric oxide synthase (NOS), 5-lipoxygenase, cyclooxygenase, protein kinase C (PKC), NADPH oxidase and gastric H+/K+-ATPase. Furthermore, ebselen may be neuroprotective due to its ability to neutralize free radicals upon NMDA receptor activation thus, reducing lipoperoxidation mediated by glutamate-induced excitotoxicity.

Ebselen Basic Attributes

Molecular Weight：

274.18

Exact Mass：

274.18

UNII：

40X2P7DPGH

NSC Number：

757883|639762

DSSTox ID：

DTXSID7045150

NCI Thesaurus Code：

C65503

HScode：

2927000090

Characteristics

PSA：

20.3

Appearance：

Yellow to beige Crystalline Powder

Melting Point：

181-182 °C @ Solvent: Methanol

Flash Point：

197.4±24.0 °C

Water Solubility：

soluble in ethanol, methanol, acetone, acetonitrile.

Storage Conditions：

2-8°C

Collision Cross Section：

145.5 Å² [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]

Safety Information

Hazard category：

6.1

Transport codes：

UN 3283 6.1/PG 3

wgk germany：

hazard class code：

23/25-33-50/53-36/37/38

safety instructions：

20/21-28-45-60-61-28A-36/37-26

RTECS Number：

DE4140750

Marks：

T,N,Xi

Precautionary statement(s)：

P261-P273-P301 + P310-P311-P501

Hazard Statements：

H301-H331-H373-H410

GHS Classification：

|Danger|H301 (97.62%): Toxic if swallowed [Danger Acute toxicity, oral]|P260, P261, P264, P270, P271, P273, P301+P310, P304+P340, P311, P314, P321, P330, P391, P403+P233, P405, and P501|Aggregated GHS information provided by 42 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Drug Information

MeSH：

Naturally occurring or synthetic substances that inhibit or retard oxidation reactions. They counteract the damaging effects of oxidation in animal tissues. (See all compounds classified as Antioxidants.)|Anti-inflammatory agents that are non-steroidal in nature. In addition to anti-inflammatory actions, they have analgesic, antipyretic, and platelet-inhibitory actions.They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins. Inhibition of prostaglandin synthesis accounts for their analgesic, antipyretic, and platelet-inhibitory actions; other mechanisms may contribute to their anti-inflammatory effects. (See all compounds classified as Anti-Inflammatory Agents, Non-Steroidal.)|Various agents with different action mechanisms used to treat or ameliorate PEPTIC ULCER or irritation of the gastrointestinal tract. This has included ANTIBIOTICS to treat HELICOBACTER INFECTIONS; HISTAMINE H2 ANTAGONISTS to reduce GASTRIC ACID secretion; and ANTACIDS for symptomatic relief. (See all compounds classified as Anti-Ulcer Agents.)|Compounds or agents that combine with cyclooxygenase (PROSTAGLANDIN-ENDOPEROXIDE SYNTHASES) and thereby prevent its substrate-enzyme combination with arachidonic acid and the formation of eicosanoids, prostaglandins, and thromboxanes. (See all compounds classified as Cyclooxygenase Inhibitors.)|Drugs intended to prevent damage to the brain or spinal cord from ischemia, stroke, convulsions, or trauma. Some must be administered before the event, but others may be effective for some time after. They act by a variety of mechanisms, but often directly or indirectly minimize the damage produced by endogenous excitatory amino acids. (See all compounds classified as Neuroprotective Agents.)

MeSH Entry Terms：

2-phenyl-1,2-benzoisoselenazol-3(2H)-one

Ebselen Use and Manufacturing

2-Phenyl-1,2-benzoselenazol-3-one acts as an antiinfammatory compounds,, in addition to that it acts as a modulator of KVβ subunits.

Computed Properties

Molecular Weight:274.19
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:1
Exact Mass:274.98494
Monoisotopic Mass:274.98494
Topological Polar Surface Area:20.3
Heavy Atom Count:16
Complexity:275
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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