SULFOXONE

US Previously Marketed

Details

Stereochemistry	ACHIRAL
Molecular Formula	C14H16N2O6S3
Molecular Weight	404.482
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OS(=O)CNC1=CC=C(C=C1)S(=O)(=O)C2=CC=C(NCS(O)=O)C=C2

InChI

InChIKey=NEDPPCHNEOMTJV-UHFFFAOYSA-N

InChI=1S/C14H16N2O6S3/c17-23(18)9-15-11-1-5-13(6-2-11)25(21,22)14-7-3-12(4-8-14)16-10-24(19)20/h1-8,15-16H,9-10H2,(H,17,18)(H,19,20)

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6753759| https://www.ncbi.nlm.nih.gov/pubmed/14888329

Sulfoxone is a water-soluble sulfone and is a competitive inhibitor of the bacterial enzyme dihydropteroate synthetase. Sulfoxone under the brand name Diasone was used as an antileprosy drug, for treatment of dermatitis herpetiformis, and to treat pulmonary tuberculosis. Presently, usage of diasone has been discontinued.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Dihydropteroate synthase 1 2 Target ID: CHEMBL2362993 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6753759	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Dermatitis herpetiformis 9 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6753759	Primary	Approved 8429	DIASONE SODIUM Approved Use Unknown Launch Date 1986
Leprosy 5 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14888329	Primary	Approved 8429	DIASONE SODIUM Approved Use Unknown Launch Date 1986
Pulmonary tuberculosis 17 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21025501	Primary	Approved 8429	DIASONE SODIUM Approved Use Unknown Launch Date 1986

C_max

Value	Dose	Co-administered	Analyte	Population
600 ng/mL REVIEW https://doi.org/10.1016/S0099-5428(08)60377-9	330 mg single, oral dose: 330 mg route of administration: Oral experiment type: SINGLE co-administered:		DAPSONE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
2.4 g single, oral Studied dose Dose: 2.4 g Route: oral Route: single Dose: 2.4 g Sources: https://pubmed.ncbi.nlm.nih.gov/13661194	unhealthy, 50 years Health Status: unhealthy Condition: leprosy Age Group: 50 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/13661194	Other AEs: Nausea, Weakness... Other AEs: Nausea Weakness Sources: https://pubmed.ncbi.nlm.nih.gov/13661194
2.4 g single, oral Studied dose Dose: 2.4 g Route: oral Route: single Dose: 2.4 g Sources: https://pubmed.ncbi.nlm.nih.gov/13661194	unhealthy, 50 years Health Status: unhealthy Condition: leprosy Age Group: 50 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/13661194	Other AEs: Malaise... Other AEs: Malaise Sources: https://pubmed.ncbi.nlm.nih.gov/13661194
1.2 g 1 times / day multiple, oral Dose: 1.2 g, 1 times / day Route: oral Route: multiple Dose: 1.2 g, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/13661194	unhealthy, 50 years Health Status: unhealthy Condition: leprosy Age Group: 50 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/13661194	Disc. AE: Hemolytic anemia, Methemoglobinemia... AEs leading to discontinuation/dose reduction: Hemolytic anemia Methemoglobinemia Sources: https://pubmed.ncbi.nlm.nih.gov/13661194
0.3 g 3 times / day multiple, oral Dose: 0.3 g, 3 times / day Route: oral Route: multiple Dose: 0.3 g, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/12996073	unhealthy, 52 years n = 1 Health Status: unhealthy Condition: leprosy Age Group: 52 years Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/12996073	Disc. AE: Erythema facial, Erythema... AEs leading to discontinuation/dose reduction: Erythema facial Erythema Furunculosis Sources: https://pubmed.ncbi.nlm.nih.gov/12996073

AEs

AE	Significance	Dose	Population
Nausea		2.4 g single, oral Studied dose Dose: 2.4 g Route: oral Route: single Dose: 2.4 g Sources: https://pubmed.ncbi.nlm.nih.gov/13661194	unhealthy, 50 years Health Status: unhealthy Condition: leprosy Age Group: 50 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/13661194
Weakness		2.4 g single, oral Studied dose Dose: 2.4 g Route: oral Route: single Dose: 2.4 g Sources: https://pubmed.ncbi.nlm.nih.gov/13661194	unhealthy, 50 years Health Status: unhealthy Condition: leprosy Age Group: 50 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/13661194
Malaise		2.4 g single, oral Studied dose Dose: 2.4 g Route: oral Route: single Dose: 2.4 g Sources: https://pubmed.ncbi.nlm.nih.gov/13661194	unhealthy, 50 years Health Status: unhealthy Condition: leprosy Age Group: 50 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/13661194
Hemolytic anemia	Disc. AE	1.2 g 1 times / day multiple, oral Dose: 1.2 g, 1 times / day Route: oral Route: multiple Dose: 1.2 g, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/13661194	unhealthy, 50 years Health Status: unhealthy Condition: leprosy Age Group: 50 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/13661194
Methemoglobinemia	Disc. AE	1.2 g 1 times / day multiple, oral Dose: 1.2 g, 1 times / day Route: oral Route: multiple Dose: 1.2 g, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/13661194	unhealthy, 50 years Health Status: unhealthy Condition: leprosy Age Group: 50 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/13661194
Erythema facial	Disc. AE	0.3 g 3 times / day multiple, oral Dose: 0.3 g, 3 times / day Route: oral Route: multiple Dose: 0.3 g, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/12996073	unhealthy, 52 years n = 1 Health Status: unhealthy Condition: leprosy Age Group: 52 years Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/12996073
Erythema	Disc. AE	0.3 g 3 times / day multiple, oral Dose: 0.3 g, 3 times / day Route: oral Route: multiple Dose: 0.3 g, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/12996073	unhealthy, 52 years n = 1 Health Status: unhealthy Condition: leprosy Age Group: 52 years Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/12996073
Furunculosis	Disc. AE	0.3 g 3 times / day multiple, oral Dose: 0.3 g, 3 times / day Route: oral Route: multiple Dose: 0.3 g, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/12996073	unhealthy, 52 years n = 1 Health Status: unhealthy Condition: leprosy Age Group: 52 years Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/12996073

Sourcing

Vendor/Aggregator	ID	URL
AAA Chemistry	AR-1A9274
ABI Chem	AC1L1K5Q
ABI Chem	AC1Q6YP0
BOC Sciences	144-75-2
ChemTik	CTK4C4202
Compound Cloud	5351
Compound Cloud	8954
Kingston Chemistry	KST-1A1474
MuseChem	M069826
NCI Plated 2007	27222
NovoSeek	5351
ZINC	ZINC000018268128	http://zinc15.docking.org/substances/ZINC000018268128
eMolecules	260190822

PubMed

Title	Date	PubMed
Synthesis of novel test compounds for antiviral chemotherapy of severe acute respiratory syndrome (SARS).	2005	16101496
Avoid, attack or do both? Behavioral and physiological adaptations in natural enemies faced with novel hosts.	2005 Nov 4	16271142
Diastereomerically and enantiomerically pure 2,3-disubstituted pyrrolidines from 2,3-aziridin-1-ols using a sulfoxonium ylide: a one-carbon homologative relay ring expansion.	2007 Feb 21	17256932
Total synthesis of azumamide A and azumamide E, evaluation as histone deacetylase inhibitors, and design of a more potent analogue.	2007 Mar 15	17311393
Beneficial effects of a diabetes specific formula on insulin sensitivity and free fatty acid in patients with type 2 diabetes mellitus.	2008 Apr 20	18701020
Impact of glycemic control on the incidence of acute kidney injury in critically ill patients: a comparison of two strategies using the RIFLE criteria.	2010 Jun	20835553

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Oral

In Vitro Use Guide

Unknown

Name

Type

Language

SULFOXONE

Common Name

English

METHANESULFINIC ACID, (SULFONYLBIS(4,1-PHENYLENEIMINO))BIS-

Common Name

English

Aldesulfone [WHO-DD]

Common Name

English

ALDESULFONE

Common Name

English

(SULFONYLBIS(4,1-PHENYLENEIMINO))DIMETHANESULFINIC ACID

Systematic Name

English

ALDESULPHONE

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29739