502-85-2

Usage

Uses

Used in Pharmaceutical Industry:
SODIUM 4-HYDROXYBUTYRATE is used as a prescription drug for the treatment of cataplexy in patients with narcolepsy. It is marketed under the brand name Xyrem by Jazz Pharmaceuticals, Inc. (Palo Alto, CA). The drug helps reduce cataplexy attacks and is distributed in accordance with strict FDA regulations.
Used in Anesthetic Applications:
SODIUM 4-HYDROXYBUTYRATE is used as a general anesthetic in the treatment of sleep disorders and clinical depression. However, it has also been identified as a "date rape drug" due to its potential for abuse.
Used in Antimicrobial Applications:
SODIUM 4-HYDROXYBUTYRATE is used as an antibacterial agent in certain applications.
Used in Research and Forensic Applications:
SODIUM 4-HYDROXYBUTYRATE (sodium salt) (exempt preparation) (Item No. 15661) is an analytical reference standard categorized as a CNS depressant. It is provided as a DEA exempt preparation and is intended for research and forensic applications.

Environmental Fate

Xyrem is a water-soluble white to off-white powder, which can be disposed by dumping the oral solution down the sanitary sewer system. This is the preferred method of disposal for drugs which have a high potential for abuse and/or accidental overdose.

Toxicity evaluation

GHB is endogenously present in the brain and at low concentrations binds to GHB receptors that are excitatory. This effect can cause euphoria, making it a drug of abuse at ‘rave’ parties. However, at higher concentrations, Xyrem is a CNS depressant and this is the main mechanism of its toxicity. The negative effects are mediated by the gamma-aminobutyric acid (GABA)B receptors. The maximum stimulation of these receptors by GHB is w69% when compared to the binding of a GABAB receptor agonist. Therefore, the drug appears to be a weak agonist of the GABA-binding site of GABAB receptors. Overdose can lead to respiratory arrest and death. The combined use of other sedative hypnotic agents or alcohol can exacerbate the toxicity of Xyrem.

InChI:InChI=1/C4H8O3.Na/c5-3-1-2-4(6)7;/h5H,1-3H2,(H,6,7);/q;+1/p-1

Upstream product

• 28341-54-0 4-(4-nitrophenoxy)butanoic acid 
• 96-48-0 4-butanolide 

Downstream Products

• 150907-74-7 4-[bis(4-methoxyphenyl)phenylmethoxy]butanoic acid 
• 93903-27-6 benzyl 4-(benzyloxy)butanoate 
• 591-81-1 4-hydroxybutanoic acid 
• 10385-30-5 4-(benzyloxy)butanoic acid 
• 452978-63-1 allyl 4-[(4-methoxybenzyl)oxy]-4-oxobutyl succinate 
• 118715-16-5 4-((tert-butyldiphenylsilyl)oxy)butanoic acid 
• 1353853-23-2 3-(3-hydroxypropyl)-2-methyl-5-(1-methylethyl)cyclohexa-2,5-diene-1,4-dione 
• 1360544-84-8 N-(benzyloxycarbonyl)-N'-(4-hydroxybutanoyl)-1,4-piperazine 
• 1192596-44-3 4-(5-phenyl-pentyloxy)-butyric acid 
• 125697-62-3 4-Nitrophenyl 4-(4,4'-dimethoxytrityloxy)-butyrate 
• 64300-98-7 benzhydryl 7-(thien-2-ylacetamido)-3-(4-hydroxybutanoyloxymethyl)-2-cephem-4-carboxylate 
• 96-48-0 4-butanolide 
• 26976-72-7 4-acetoxybutyric acid 
• 91970-62-6 benzyl 4-hydroxybutanoate 

Relevant academic research and scientific papers

Metallic Nanoparticle-Enabled Sensing of a Drug-of-Abuse: An Attempt at Forensic Application

γ-Hydroxybutyric acid (GHB) functions as a depressant on the central nerve system and serves as a pharmaceutical agent in the treatment of narcolepsy and alcohol withdraw. In recent years, GHB has been misused as a recreational drug due to its ability to induce euphoric feelings. Moreover, it has gained increasing attention as a popular drug of abuse that is frequently related to drug-facilitated sexual assaults. At the moment, detection methods based on chromatography exhibit extraordinary sensitivity for GHB sensing. However, such techniques require complicated sample treatment prior to analysis. Optical sensors provide an alternative approach for rapid and simple analysis of GHB samples. Unfortunately, currently reported probes are mostly based on hydrogen bonding to recognize GHB, and this raises concerns about, for example, the lack of specificity. In this work, we report a bioinspired strategy for selective sensing of GHB. The method is based on specific enzyme recognition to allow highly selective detection of GHB with minimum interference, even in a complex sample matrix (e. g., simulated urine). In addition, the result can be obtained by either quantitative spectroscopy analysis or colorimetric change observed by the naked-eye, thus demonstrating its potential application in drug screening and forensic analysis.

Development of a fluorescent sensor for illicit date rape drug GHB

The first fluorescent sensor (GHB Orange) for date rape drug GHB was developed. It exhibits the fluorescence quenching property for GHB and allows its detection in various drinks. The interaction mechanism was elucidated as intramolecular charge transfer induced by a hydrogen bond. This discovery will help in solving the drug facilitated sexual assault problems.

Derivatives of Napabucasin and pharmaceutical application thereof

The invention relates to derivatives of Napabucasin, and a pharmaceutical application thereof. The structure of the derivatives conforms to the general formula (I), and the water solubility of most of the compounds is obviously higher than that of Napabucasin. The compounds and pharmaceutically acceptable salts thereof can be used for preparing antitumor drugs, and the cell inhibition activity of most of the compounds is obviously superior to that of Napabucasin. Meanwhile, experiments show that the compounds have extremely high helicobacter pylori and fungal activity resistance and can be used for preparing drugs for resisting helicobacter pylori and fungal infection.

MODIFIED AMINE LIPIDS

The disclosure provides ionizable amine lipids and salts thereof (e.g., pharmaceutically acceptable salts thereof) useful for the delivery of biologically active agents, for example delivering biologically active agents to cells to prepare engineered cells. The ionizable amine lipids disclosed herein are useful as ionizable lipids in the formulation of lipid nanoparticle-based compositions.

Synthesis of Thymoquinone-Artemisinin Hybrids: New Potent Antileukemia, Antiviral, and Antimalarial Agents

A series of hybrid compounds based on the natural products artemisinin and thymoquinone was synthesized and investigated for their biological activity against the malaria parasite Plasmodium falciparum 3D7 strain, human cytomegalovirus (HCMV), and two leukemia cell lines (drug-sensitive CCRF-CEM and multidrug-resistant subline CEM/ADR5000). An unprecedented one-pot method of selective formation of C-10α-acetate 14 starting from a 1:1 mixture of C-10α- to C-10β-dihydroartemisinin was developed. The key step of this facile method is a mild decarboxylative activation of malonic acid mediated by DCC/DMAP. Ether-linked thymoquinone-artemisinin hybrids 6a/b stood out as the most active compounds in all categories, while showing no toxic side effects toward healthy human foreskin fibroblasts and thus being selective. They exhibited EC50 values of 0.2 μM against the doxorubicin-sensitive as well as the multidrug-resistant leukemia cells and therefore can be regarded as superior to doxorubicin. Moreover, they showed to be five times more active than the standard drug ganciclovir and nearly eight times more active than artesunic acid against HCMV. In addition, hybrids 6a/b possessed excellent antimalarial activity (EC50 = 5.9/3.7 nM), which was better than that of artesunic acid (EC50 = 8.2 nM) and chloroquine (EC50 = 9.8 nM). Overall, most of the presented thymoquinone-artemisinin-based hybrids exhibit an excellent and broad variety of biological activities (anticancer, antimalarial, and antiviral) combined with a low toxicity/high selectivity profile.

GAMMA-HYDROXYBUTYRATE COMPOSITIONS AND THEIR USE FOR THE TREATMENT OF DISORDERS

Provided herein are pharmaceutical compositions and formulations comprising mixed salts of gamma-hydroxybutyrate (GHB). Also provided herein are methods of making the pharmaceutical compositions and formulations, and methods of their use for the treatment of sleep disorders such as apnea, sleep time disturbances, narcolepsy, cataplexy, sleep paralysis, hypnagogic hallucination, sleep arousal, insomnia, and nocturnal myoclonus.

Synthesis of Novel Hybrids of Thymoquinone and Artemisinin with High Activity and Selectivity Against Colon Cancer

Colorectal cancer causes 0.5 million deaths each year. To combat this type of cancer the development of new specific drug candidates is urgently needed. In the present work seven novel thymoquinone–artemisinin hybrids with different linkers were synthesized and tested for their in vitro anticancer activity against a panel of various tumor cell lines. The thymoquinone–artesunic acid hybrid 7 a, in which both subunits are connected via an ester bond, was found to be the most active compound and selectively decreased the viability of colorectal cancer cells with an IC50value of 2.4 μm (HCT116) and 2.8 μm (HT29). Remarkably, hybrid 7 a was up to 20-fold more active than its parent compounds (thymoquinone and artesunic acid), while not affecting nonmalignant colon epithelial HCEC cells (IC50>100 μm). Moreover, the activity of hybrid 7 a was superior to that of various 1:1 mixtures of thymoquinone and artesunic acid. Furthermore, hybrid 7 a was even more potent against both colon cancer cell lines than the clinically used drug 5-fluorouracil. These results are another excellent proof of the hybridization concept and confirm that the type and length of the linker play a crucial role for the biological activity of a hybrid drug. Besides an increase in reactive oxygen species (ROS), elevated levels of the DNA-damage marker γ-H2AX were observed. Both effects seem to be involved in the molecular mechanism of action for hybrid 7 a in colorectal cancer cells.

AMIDE COMPOUNDS, METHODS FOR PREPARATION, AND USE THEREOF AS AGENTS FOR THE TREATMENT AND PREVENTION OF DISEASES CAUSED BY RNA- AND/OR DNA-CONTAINING VIRUSES, AND CONCOMITANT DISEASES

The present invention relates to medicine and includes a method for preventing and treating diseases caused by RNA- and DNA-containing viruses, and concomitant diseases, wherein the method comprises the use of an effective amount of compounds of general formula I or pharmaceutically acceptable salts thereof. The invention also relates to methods for preparing said compounds, pharmaceutical compositions for the prevention or treatment of diseases caused by RNA- and DNA-containing viruses, said compositions comprising an effective amount of a compound of formula I or a pharmaceutically acceptable salt thereof. The invention addresses the object of providing a novel agent effective in the treatment of diseases caused by an RNA-containing virus belonging to the Enterovirus, Metapneumovirus, Pneumovirus, Respirovirus, or Alfa-coronavirus genus, and/or by a DNA-containing virus belonging to the Adenoviridae and/or Herpesviridae family, and in the prevention and treatment of asthma exacerbation, chronic obstructive pulmonary disease, mucoviscidosis, conjunctivitis, gastroenteritis, hepatitis, myocarditis; in the prevention and treatment of rhinorrhea, acute and infectious rhinitis, pharyngitis, nasopharyngitis, tonsillitis, laryngitis, laryngotracheitis, laryngotracheobronchitis, bronchitis, bronchiolitis, pneumonia, or airway obstructive syndrome.

Reagents And Methods for Detecting Protein Lysine 3-Hydroxybutyrylation

The invention provides an isolated peptide comprising a lysine 3-hydroxybutyrylation site, a lysine 3-hydroxybutyrylation specific affinity reagent that specifically binds to the peptide, and a method for detecting protein lysine 3-hydroxybutyrylation in a sample using the reagent.

DIPEPTIDE AND TRIPEPTIDE EPOXY KETONE PROTEASE INHIBITORS

Provided herein are dipeptide and tripeptide epoxy ketone protease inhibitors, methods of their preparation, related pharmaceutical compositions, and methods of using the same. For example, provided herein are compounds of Formula (X): and pharmaceutically acceptable salts and compositions including the same. The compounds and compositions provided herein may be used, for example, in the treatment of proliferative diseases including cancer and autoimmune diseases.