Acediasulfone

Last updated
Acediasulfone
Acediasulfone Structure.svg
Clinical data
ATC code
  • none
Identifiers
  • 2-([4-(4-aminophenyl)sulfonylphenyl]amino)acetic acid
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.001.131 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C14H14N2O4S
Molar mass 306.34 g·mol−1
3D model (JSmol)
  • C1=CC(=CC=C1N)S(=O)(=O)C2=CC=C(C=C2)NCC(=O)O
  • InChI=1S/C14H14N2O4S/c15-10-1-5-12(6-2-10)21(19,20)13-7-3-11(4-8-13)16-9-14(17)18/h1-8,16H,9,15H2,(H,17,18) Yes check.svgY
  • Key:FKKUMFTYSTZUJG-UHFFFAOYSA-N Yes check.svgY
   (verify)

Acediasulfone (INN) is an antimicrobial drug, which also has antimalarial activity. It is a long-acting prodrug of dapsone, which is used for treating leprosy.

Synthesis

Dapsone is somewhat inconvenient to administer to patients because of its rather low water solubility.

Acediasulfone synthesis: .mw-parser-output .citation{word-wrap:break-word}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)} CH 254803 and CH 278482 (1949, 1952, to Cilag Ltd.); Rawlins, U.S. patent 2,589,211 (1952 to Parke-Davis). Acediasulfone synthesis.svg
Acediasulfone synthesis: CH 254803   and CH 278482   (1949, 1952, to Cilag Ltd.); Rawlins, U.S. patent 2,589,211 (1952 to Parke-Davis).

In the search for more easily administered drugs, dapsone (1) was reacted with bromoacetic acid to give acediasulfone (2) which can be administered as a water-soluble salt.

Related Research Articles

<span class="mw-page-title-main">Solubility</span> Capacity of a substance to dissolve in a homogeneous way

In chemistry, solubility is the ability of a substance, the solute, to form a solution with another substance, the solvent. Insolubility is the opposite property, the inability of the solute to form such a solution.

<span class="mw-page-title-main">Methemoglobinemia</span> Condition of elevated methemoglobin in the blood

Methemoglobinemia, or methaemoglobinaemia, is a condition of elevated methemoglobin in the blood. Symptoms may include headache, dizziness, shortness of breath, nausea, poor muscle coordination, and blue-colored skin (cyanosis). Complications may include seizures and heart arrhythmias.

<span class="mw-page-title-main">Dapsone</span> Antibiotic medication

Dapsone, also known as 4,4'-sulfonyldianiline (SDA) or diaminodiphenyl sulfone (DDS), is an antibiotic commonly used in combination with rifampicin and clofazimine for the treatment of leprosy. It is a second-line medication for the treatment and prevention of pneumocystis pneumonia and for the prevention of toxoplasmosis in those who have poor immune function. Additionally, it has been used for acne, dermatitis herpetiformis, and various other skin conditions. Dapsone is available both topically and by mouth.

In pharmacology, bioavailability is a subcategory of absorption and is the fraction (%) of an administered drug that reaches the systemic circulation.

<span class="mw-page-title-main">Polyvinyl alcohol</span> Chemical compound

Polyvinyl alcohol (PVOH, PVA, or PVAl) is a water-soluble synthetic polymer. It has the idealized formula [CH2CH(OH)]n. It is used in papermaking, textile warp sizing, as a thickener and emulsion stabilizer in polyvinyl acetate (PVAc) adhesive formulations, in a variety of coatings, and 3D printing. It is colourless (white) and odorless. It is commonly supplied as beads or as solutions in water. Without an externally added crosslinking agent, PVA solution can be gelled through repeated freezing-thawing, yielding highly strong, ultrapure, biocompatible hydrogels which have been used for a variety of applications such as vascular stents, cartilages, contact lenses, etc.

In pharmacology, the volume of distribution is the theoretical volume that would be necessary to contain the total amount of an administered drug at the same concentration that it is observed in the blood plasma. In other words, it is the ratio of amount of drug in a body (dose) to concentration of the drug that is measured in blood, plasma, and un-bound in interstitial fluid.

<span class="mw-page-title-main">Avizafone</span> Diazepam prodrug

Avizafone (Pro-Diazepam) is a water-soluble prodrug of the benzodiazepine derivative diazepam. It can be administered intramuscularly.

<span class="mw-page-title-main">Fosphenytoin</span> Anti-epileptic drug

Fosphenytoin, also known as fosphenytoin sodium, and sold under the brand name Cerebyx among others, is a water-soluble phenytoin prodrug that is administered intravenously to deliver phenytoin, potentially more safely than intravenous phenytoin. It is used in the acute treatment of convulsive status epilepticus.

<span class="mw-page-title-main">Pentetic acid</span> DTPA: aminopolycarboxylic acid

Pentetic acid or diethylenetriaminepentaacetic acid (DTPA) is an aminopolycarboxylic acid consisting of a diethylenetriamine backbone with five carboxymethyl groups. The molecule can be viewed as an expanded version of EDTA and is used similarly. It is a white solid with limited solubility in water.

<span class="mw-page-title-main">Doripenem</span> Antibiotic

Doripenem is an antibiotic drug in the carbapenem class. It is a beta-lactam antibiotic drug able to kill Pseudomonas aeruginosa.

<span class="mw-page-title-main">Tepoxalin</span> NSAID anti-inflammatory veterinary drug

Tepoxalin, sold under the brand name Zubrin among others, is a non-steroidal anti-flammatory drug (NSAIDs) generally used in veterinary medicine to reduce swelling in animals with osteoarthritis. In rare circumstances, tepoxalin can also be used in human pharmacology to relieve pain caused by musculoskeletal conditions such as arthritis and hip dysplasia.

Druglikeness is a qualitative concept used in drug design for how "druglike" a substance is with respect to factors like bioavailability. It is estimated from the molecular structure before the substance is even synthesized and tested. A druglike molecule has properties such as:

<span class="mw-page-title-main">Calcium dobesilate</span> Chemical compound

Calcium dobesilate is a vasoprotective. It is the calcium salt of dobesilic acid. It is a synthetic molecule with the ability to reduce capillary permeability in the body. In Switzerland the drug is sold by the pharmaceutical company OM Pharma under the trade name of Doxium in capsules containing 500 mg of active ingredient.

<span class="mw-page-title-main">Flunoxaprofen</span> Chemical compound

Flunoxaprofen, also known as Priaxim, is a chiral nonsteroidal anti-inflammatory drug (NSAID). It is closely related to naproxen, which is also an NSAID. Flunoxaprofen has been shown to significantly improve the symptoms of osteoarthritis and rheumatoid arthritis. The clinical use of flunoxaprofen has ceased due to concerns of potential hepatotoxicity.

<span class="mw-page-title-main">O-2694</span> Chemical compound

O-2694 is a drug that is a cannabinoid derivative. It has analgesic effects and is used in scientific research. Unlike most cannabinoids discovered to date, it is highly water-soluble, which gives it considerable advantages over many related drugs. It has high affinity for both CB1 and CB2 receptors, with Ki values of 3.7 nM at CB1 and 2.8 nM at CB2. However, it has complex pharmacokinetics as most of the administered dose is metabolised by hydrolysis of the ester link to the water-insoluble compound O-2372, thus producing a biphasic effects profile that is less suitable for research purposes than the related compound O-2545.

<span class="mw-page-title-main">Acedapsone</span> Antimicrobial drug

Acedapsone (INN) is an antimicrobial drug, which also has antimalarial activity.

A leprostatic agent is a drug that interferes with proliferation of the bacterium that causes leprosy.

Neutrophilic eccrine hidradenitis (NEH) usually is a cutaneous complication of chemotherapy, but it can also occur for other reasons. It consists of fever and non specific skin lesions. It is rare, and self-limited.

<span class="mw-page-title-main">Org 28611</span> Chemical compound

Org 28611 (SCH-900,111) is a drug developed by Organon International which acts as a potent cannabinoid receptor full agonist at both the CB1 and CB2 receptors. It was developed with the aim of finding a water-soluble cannabinoid agonist suitable for intravenous use as an analgesic, and while it achieved this aim and has progressed as far as Phase II clinical trials in humans as both a sedative and an analgesic, results against the comparison drugs (midazolam and morphine respectively) were not particularly favourable in initial testing.

<span class="mw-page-title-main">Promin</span> Chemical compound

Promin, or sodium glucosulfone is a sulfone drug that was investigated for the treatment of malaria, tuberculosis and leprosy. It is broken down in the body to dapsone, which is the therapeutic form.

References

  1. ↑ Jackson EL (February 1948). "Certain N-alkyl, N-carboxyalkyl and N-hydroxyalkyl derivatives of 4,4'-diaminodiphenyl sulfone". Journal of the American Chemical Society. 70 (2): 680–4. doi:10.1021/ja01182a074. PMID   18907772.


This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.