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Acedapsone

Acedapsone structure

CAS No:
77-46-3
Formula:
C16H16N2O4S
Chemical Name:
Acedapsone
Synonyms:
Acetamide,N,N′-(sulfonyldi-4,1-phenylene)bis-;Acetanilide,4′,4′′′-sulfonylbis-;N,N′-(Sulfonyldi-4,1-phenylene)bis[acetamide];C.I. 556;1399F;Bis(4-acetamidophenyl) sulfone;Camilan;DADDS;4,4′-Diacetamidodiphenyl sulfone;Rodilone;Sulfadiamine;Sulfodiamine;p,p′-Sulfonylbisacetanilide;Acedapsone;Diacetyldapsone;N,N′-Diacetyl-4,4′-diaminophenyl sulfone;BA 2650;Acetamin;4,4′-Bis(acetylamino)diphenyl sulfone;N,N′-Diacetyldapsone;Sulfodiamin;Atilon;Hansolar;Acetamin (antibacterial);4,4′-Sulfonylbisacetanilide;PAM-MR 1165;CI 556;CN 1883;NSC 218125;NSC 655049
Categories:
Chemical Reagents > Organic Reagents

Description

Acedapsone is a sulfone that is dapsone in which both of the amino groups been acetylation. An antimicrobial drug, it also has antimalarial activity. It has a role as an antimicrobial drug and an antimalarial. It is a sulfone, a secondary carboxamide, a member of acetamides and an anilide. It derives from a dapsone.|Acetylated sulfone that is slowly metabolized to give long-term, low blood levels of DAPSONE. It has antimicrobial and antimalarial action, but is mainly used as a depot leprostatic agent.

Acedapsone Basic Attributes

Molecular Weight：

332.378

Exact Mass：

332.37

EC Number：

201-028-8

UNII：

0GZ72U84TN

NSC Number：

759111|655049|218125

DSSTox ID：

DTXSID1021295

Characteristics

PSA：

101

XLogP3：

1.1

Density：

1.2982 (rough estimate)

Melting Point：

290 °C

Collision Cross Section：

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

Drug Information

MeSH：

Agents used in the treatment of malaria. They are usually classified on the basis of their action against plasmodia at different stages in their life cycle in the human. (From AMA, Drug Evaluations Annual, 1992, p1585) (See all compounds classified as Antimalarials.)|Substances that suppress Mycobacterium leprae, ameliorate the clinical manifestations of leprosy, and/or reduce the incidence and severity of leprous reactions. (See all compounds classified as Leprostatic Agents.)|Substances that prevent infectious agents or organisms from spreading or kill infectious agents in order to prevent the spread of infection. (See all compounds classified as Anti-Infective Agents.)

MeSH Entry Terms：

4',4'''-Sulfonylbis(acetanilide)

Acedapsone Use and Manufacturing

Methods of Manufacturing

From dapsone, acetic acid and acetic anhydride together heating reflux, acetylation. The crude product obtained is decolorized and refined by adding activated carbon in ethanol to obtain the fine product of acetamide phenyl sulfone. Based on dapsone, the total yield is about 76%.

Uses

Anti-leprosy drugs.

Computed Properties

Molecular Weight:332.4
XLogP3:1.1
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:4
Exact Mass:332.08307817
Monoisotopic Mass:332.08307817
Topological Polar Surface Area:101
Heavy Atom Count:23
Complexity:483
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes