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    Chemistry

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    Also known as: 80-08-0, 4,4'-sulfonyldianiline, Diaphenylsulfone, 4,4'-diaminodiphenyl sulfone, Dapson, 4-aminophenyl sulfone
    Molecular Formula
    C12H12N2O2S
    Molecular Weight
    248.30  g/mol
    InChI Key
    MQJKPEGWNLWLTK-UHFFFAOYSA-N
    FDA UNII
    8W5C518302
    Dapsone
    A sulfone active against a wide range of bacteria but mainly employed for its actions against MYCOBACTERIUM LEPRAE. Its mechanism of action is probably similar to that of the SULFONAMIDES which involves inhibition of folic acid synthesis in susceptible organisms. It is also used with PYRIMETHAMINE in the treatment of malaria. (From Martindale, The Extra Pharmacopoeia, 30th ed, p157-8)
    Dapsone is a Sulfone.
    1 2D Structure

    Dapsone

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    4-(4-aminophenyl)sulfonylaniline
    2.1.2 InChI
    InChI=1S/C12H12N2O2S/c13-9-1-5-11(6-2-9)17(15,16)12-7-3-10(14)4-8-12/h1-8H,13-14H2
    2.1.3 InChI Key
    MQJKPEGWNLWLTK-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    C1=CC(=CC=C1N)S(=O)(=O)C2=CC=C(C=C2)N
    2.2 Other Identifiers
    2.2.1 UNII
    8W5C518302
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 4,4' Diaminophenyl Sulfone

    2. 4,4'-diaminophenyl Sulfone

    3. Avlosulfone

    4. Dadps

    5. Dapsoderm-x

    6. Dapson-fatol

    7. Diaminodiphenylsulfone

    8. Diaphenylsulfone

    9. Disulone

    10. Sulfona

    11. Sulfone, 4,4'-diaminophenyl

    12. Sulfonyldianiline

    2.3.2 Depositor-Supplied Synonyms

    1. 80-08-0

    2. 4,4'-sulfonyldianiline

    3. Diaphenylsulfone

    4. 4,4'-diaminodiphenyl Sulfone

    5. Dapson

    6. 4-aminophenyl Sulfone

    7. 4,4'-diaminodiphenylsulfone

    8. Diaphenylsulfon

    9. Novophone

    10. Sulfona

    11. Dadps

    12. Bis(4-aminophenyl) Sulfone

    13. Avlosulfone

    14. Diphenasone

    15. Sulfadione

    16. Sulphadione

    17. Dapsonum

    18. Disulone

    19. Aczone

    20. Udolac

    21. P-aminophenyl Sulfone

    22. Avlosulfon

    23. Croysulfone

    24. Dumitone

    25. Diphone

    26. Eporal

    27. Diaphenylsulphon

    28. Diaphenylsulphone

    29. Metabolite C

    30. Sulfonyldianiline

    31. Sumicure S

    32. Bis(p-aminophenyl) Sulfone

    33. Sulphonyldianiline

    34. P,p-sulphonylbisbenzamine

    35. Sulfona-mae

    36. Avlosulphone

    37. Croysulphone

    38. Dubronax

    39. 4,4'-dapsone

    40. Diaminodiphenyl Sulfone

    41. Tarimyl

    42. P,p-sulphonylbisbenzenamine

    43. Sulfone Ucb

    44. 4,4'-sulfonylbisaniline

    45. P,p'-diaminodiphenyl Sulfone

    46. 4-(4-aminophenyl)sulfonylaniline

    47. Dapsona

    48. Nsc-6091

    49. Benzenamine, 4,4'-sulfonylbis-

    50. Diaminodiphenylsulfone

    51. Bis(4-aminophenyl)sulfone

    52. Di(p-aminophenyl) Sulfone

    53. P,p-sulphonyldianiline

    54. 4,4'-sulfonylbisbenzamine

    55. Di(4-aminophenyl) Sulfone

    56. P,p'-sulfonyldianiline

    57. 4,4'-sulfonylbisbenzenamine

    58. P,p-sulfonylbisbenzamine

    59. Diaminodifenilsulfona

    60. Dds, Pharmaceutical

    61. Di(p-aminophenyl)sulphone

    62. P,p-sulfonylbisbenzenamine

    63. Araldite Ht 976

    64. Bis(p-aminophenyl)sulphone

    65. Di(4-aminophenyl)sulphone

    66. Bis(4-aminophenyl)sulphone

    67. P,p-diaminodiphenyl Sulphone

    68. N,n'-diphenyl Sulfondiamide

    69. 1,1'-sulfonylbis(4-aminobenzene)

    70. 4,4'-sulphonyldianiline

    71. Dds

    72. Servidapson

    73. 4,4'-sulphonylbisbenzamine

    74. 4,4'-sulphonylbisbenzenamine

    75. 4,4'-diaminodiphenyl Sulphone

    76. Wr 448

    77. 4,4-diaminodifenylsulfon

    78. Diamino-4,4'-diphenyl Sulfone

    79. Diamino-4,4'-diphenyl Sulphone

    80. Nsc 6091d

    81. Nci-c01718

    82. 1,1'-sulfonylbis[4-aminobenzene]

    83. 1,1'-sulphonylbis(4-aminobenzene)

    84. Aniline, 4,4'-sulfonyldi-

    85. Ht 976

    86. 4,4'-diamino Diphenyl Sulphone

    87. F 1358

    88. 4,4'-sulfonyldianiline (dapsone)

    89. 1358f

    90. 4-[(4-aminobenzene)sulfonyl]aniline

    91. 4,4'-sulfonylbisbenzeneamine

    92. 4,4'-sulfonyldianilin

    93. Diaphenylsulfone (jan)

    94. Chembl1043

    95. Mls000069409

    96. Chebi:4325

    97. Dtxsid4020371

    98. Nsc-6091d

    99. Sulfanona-mae

    100. J04ba02

    101. Nsc6091

    102. Sulfon-mere

    103. 4,4'-dds

    104. Di(4-aminophenyl)sulfone

    105. 4-(4-amino-benzenesulfonyl)-phenylamine

    106. Ncgc00016322-08

    107. Smr000059064

    108. Hardener Ht 976

    109. Dds (pharmaceutical)

    110. Sulphon-mere

    111. Dsstox_cid_371

    112. 8w5c518302

    113. Dapsonum [inn-latin]

    114. Dapsona [inn-spanish]

    115. Dsstox_rid_75547

    116. Dsstox_gsid_20371

    117. Dss (van)

    118. Diaphenylsulfone [jan]

    119. 4-aminophenylsulfone

    120. 4 4-diamino Diphenyl Sulfone 99.5%min Cas:80-08-8

    121. Dds, Diaphenylsulfone

    122. 4,4'-diaminodiphenyl Suphone

    123. Atrisone

    124. Diaminodifenilsulfona [spanish]

    125. 4,4-diaminodifenylsulfon [czech]

    126. Cas-80-08-0

    127. Hy 976

    128. Ccris 192

    129. Dapsone (usp)

    130. Aczone (tn)

    131. 1632119-29-9

    132. Hsdb 5073

    133. Sr-01000002976

    134. Nsc 6091

    135. 4-[(4-aminophenyl)sulfonyl]aniline

    136. Sulfone, Diphenyl, 4,4'-diamino-

    137. Einecs 201-248-4

    138. (4-sulfanilylphenyl)amine

    139. Mfcd00007887

    140. Azt + Dapsone Cominbation

    141. Brn 0788055

    142. Ai3-08087

    143. Diaphenyl Sulfone

    144. Dapsone [usan:usp:inn:ban]

    145. Unii-8w5c518302

    146. Dapsone,(s)

    147. Prestwick_152

    148. Albb-005917

    149. Dapsone-d8(major)

    150. Dapsone-[d4]

    151. In-201

    152. Dapsone-13c12

    153. Bis Sulfone

    154. 4,4''-dapsone

    155. 4-[(4-aminophenyl)sulfonyl]phenylamine

    156. Dapsone-[15n2]

    157. Spectrum_000888

    158. Dapsone [vandf]

    159. Aniline,4'-sulfonyldi-

    160. Dapsone [hsdb]

    161. Dapsone [iarc]

    162. Dapsone [usan]

    163. Dapsone [inn]

    164. Dapsone [mi]

    165. Dapsone [mart.]

    166. Opera_id_1950

    167. Prestwick0_000035

    168. Prestwick1_000035

    169. Prestwick2_000035

    170. Prestwick3_000035

    171. Spectrum2_001133

    172. Spectrum3_000375

    173. Spectrum4_000310

    174. Spectrum5_000825

    175. Wln: Zr Dswr Dz

    176. 4,4''-sulfonyldianiline

    177. Dapsone [usp-rs]

    178. Dapsone [who-dd]

    179. Dapsone [who-ip]

    180. 4,4''-sulfonylbisaniline

    181. Ec 201-248-4

    182. 4,4'-sulfonyldiphenylamine

    183. Benzenamine,4'-sulfonylbis-

    184. Oprea1_143052

    185. Schembl21428

    186. Bspbio_000129

    187. Bspbio_002129

    188. Cbdive_013582

    189. Dianiline, 4,4'-sulfonyl-

    190. Kbiogr_000900

    191. Kbioss_001368

    192. Mls001055349

    193. Mls001076146

    194. 4,4''-sulfonylbisbenzenamine

    195. 4,4'-sulfonylbis[benzamine]

    196. 4-aminophenyl Sulfone, 97%

    197. Bidd:gt0770

    198. Dapsone [ep Impurity]

    199. Dapsone [orange Book]

    200. Divk1c_000573

    201. P,p''-diaminodiphenyl Sulfone

    202. Spectrum1500222

    203. Spbio_001025

    204. Spbio_002050

    205. Dapsone [ep Monograph]

    206. 4,4''-diaminodiphenyl Sulfone

    207. 4,4'-diamino Diphenyl Sulfone

    208. Bpbio1_000143

    209. Zinc6310

    210. Dapsone [usp Monograph]

    211. Dapsonum [who-ip Latin]

    212. Gtpl10934

    213. Hms501m15

    214. Kbio1_000573

    215. Kbio2_001368

    216. Kbio2_003936

    217. Kbio2_006504

    218. Kbio3_001349

    219. 4-(4-aminophenylsulfonyl)aniline

    220. Ninds_000573

    221. Hms1568g11

    222. Hms1920c14

    223. Hms2091k04

    224. Hms2095g11

    225. Hms2231g09

    226. Hms3259c13

    227. Hms3369b11

    228. Hms3712g11

    229. Pharmakon1600-01500222

    230. Dapson 100 Microg/ml In Methanol

    231. Act07431

    232. Amy40781

    233. Hy-b0688

    234. 1,1''-sulfonylbis(4-aminobenzene)

    235. Tox21_110371

    236. Tox21_201347

    237. Tox21_300558

    238. 4-(4-aminophenylsulfonyl)benzenamine

    239. Bbl002412

    240. Bdbm50029764

    241. Ccg-40260

    242. Nsc756716

    243. S4612

    244. Stk387118

    245. Akos000119322

    246. Tox21_110371_1

    247. Db00250

    248. Ht 9664

    249. Ks-1450

    250. Nc00488

    251. Nsc-756716

    252. Idi1_000573

    253. Ncgc00016322-01

    254. Ncgc00016322-02

    255. Ncgc00016322-03

    256. Ncgc00016322-04

    257. Ncgc00016322-05

    258. Ncgc00016322-06

    259. Ncgc00016322-07

    260. Ncgc00016322-09

    261. Ncgc00016322-10

    262. Ncgc00016322-13

    263. Ncgc00023946-03

    264. Ncgc00023946-04

    265. Ncgc00023946-05

    266. Ncgc00023946-06

    267. Ncgc00254533-01

    268. Ncgc00258899-01

    269. Ac-10922

    270. 4-[(4-aminophenyl)sulfonyl]phenylamine #

    271. Sbi-0051331.p003

    272. Db-056406

    273. Ab00051962

    274. D0089

    275. Dapsone, Vetranal(tm), Analytical Standard

    276. Ft-0624447

    277. Ft-0665473

    278. 4 Inverted Exclamation Marka-sulfonyldianiline

    279. C07666

    280. D00592

    281. Ab00051962_19

    282. A839828

    283. Q422226

    284. 4 Inverted Exclamation Marka-diaminodiphenyl Sulfone

    285. 4,4 Inverted Exclamation Mark(r)-sulfonyldianiline

    286. Q-200435

    287. Sr-01000002976-2

    288. Sr-01000002976-4

    289. Brd-k62363391-001-05-8

    290. Brd-k62363391-001-15-7

    291. Sulfacetamide Sodium Impurity D [ep Impurity]

    292. Dapsone, British Pharmacopoeia (bp) Reference Standard

    293. Dapsone, European Pharmacopoeia (ep) Reference Standard

    294. F0266-3067

    295. 2-(piperazin-1-yl)-aceticacidn-(2-phenylethyl)-amide

    296. 4-(4-aminophenyl)sulfonylaniline;4,4'-diaminodiphenyl Sulfone

    297. Dapsone, United States Pharmacopeia (usp) Reference Standard

    298. Dapsone, Pharmaceutical Secondary Standard; Certified Reference Material

    2.4 Create Date
    2005-03-25
    3 Chemical and Physical Properties
    Molecular Weight 248.30 g/mol
    Molecular Formula C12H12N2O2S
    XLogP31
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count4
    Rotatable Bond Count2
    Exact Mass248.06194880 g/mol
    Monoisotopic Mass248.06194880 g/mol
    Topological Polar Surface Area94.6 Ų
    Heavy Atom Count17
    Formal Charge0
    Complexity306
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 4  
    Drug NameAczone
    PubMed HealthDapsone
    Drug ClassesAntiacne, Leprostatic
    Drug LabelACZONE Gel, 5%, contains dapsone, a sulfone, in an aqueous gel base for topical dermatologic use. ACZONE Gel, 5% is a gritty translucent material with visible drug substance particles. Chemically, dapsone has an empirical formula of C12H12N2O2S....
    Active IngredientDapsone
    Dosage FormGel
    RouteTopical
    Strength5%
    Market StatusPrescription
    CompanyAllergan

    2 of 4  
    Drug NameDapsone
    PubMed HealthDapsone
    Drug ClassesAntiacne, Leprostatic
    Drug LabelDapsone-USP, 4,4'-diaminodiphenylsulfone (DDS), is a primary treatment for Dermatitis herpetiformis. It is an antibacterial drug for susceptible cases of leprosy. It is a white, odorless crystalline powder, practically in-soluble in water and insolub
    Active IngredientDapsone
    Dosage FormTablet
    RouteOral
    Strength100mg; 25mg
    Market StatusPrescription
    CompanyJacobus

    3 of 4  
    Drug NameDapsone
    PubMed HealthDapsone
    Drug ClassesAntiacne, Leprostatic
    Drug LabelDapsone-USP, 4,4'-diaminodiphenylsulfone (DDS), is a primary treatment for Dermatitis herpetiformis. It is an antibacterial drug for susceptible cases of leprosy. It is a white, odorless crystalline powder, practically in-soluble in water and insolub
    Active IngredientDapsone
    Dosage FormTablet
    RouteOral
    Strength100mg; 25mg
    Market StatusPrescription
    CompanyJacobus

    4 of 4  
    Drug NameAczone
    PubMed HealthDapsone
    Drug ClassesAntiacne, Leprostatic
    Drug LabelACZONE Gel, 5%, contains dapsone, a sulfone, in an aqueous gel base for topical dermatologic use. ACZONE Gel, 5% is a gritty translucent material with visible drug substance particles. Chemically, dapsone has an empirical formula of C12H12N2O2S....
    Active IngredientDapsone
    Dosage FormGel
    RouteTopical
    Strength5%
    Market StatusPrescription
    CompanyAllergan

    4.2 Therapeutic Uses

    Anti-Infective Agents; Antimalarials; Folic Acid Antagonists; Leprostatic Agents

    National Library of Medicine's Medical Subject Headings. Dapsone. Online file (MeSH, 2016). Available from, as of August 12, 2016: https://www.nlm.nih.gov/mesh/2016/mesh_browser/MBrowser.html

    /CLINICAL TRIALS/ ClinicalTrials.gov is a registry and results database of publicly and privately supported clinical studies of human participants conducted around the world. The Web site is maintained by the National Library of Medicine (NLM) and the National Institutes of Health (NIH). Each ClinicalTrials.gov record presents summary information about a study protocol and includes the following: Disease or condition; Intervention (for example, the medical product, behavior, or procedure being studied); Title, description, and design of the study; Requirements for participation (eligibility criteria); Locations where the study is being conducted; Contact information for the study locations; and Links to relevant information on other health Web sites, such as NLM's MedlinePlus for patient health information and PubMed for citations and abstracts for scholarly articles in the field of medicine. Dapsone is included in the database.

    NIH/NLM; ClinicalTrials.Gov. Available from, as of March 17, 2016: https://clinicaltrials.gov/ct2/results?term=dapsone&Search=Search

    Dapsone is administered as an oral agent. Dapsone is combined with chlorproguanil for the treatment of malaria. Dapsone is also used for P. jiroveci infection and prophylaxis, and for the prophylaxis for T. gondii ... The anti-inflammatory effects are the basis for therapy for pemphigoid, dermatitis herpetiformis, linear IgA bullous disease, relapsing chondritis, and ulcers caused by the brown recluse spider.

    Brunton, L. Chabner, B, Knollman, B. Goodman and Gillman's The Pharmaceutical Basis of Therapeutics, Twelth Edition, McGraw Hill Medical, New York, NY. 2011, p. 1574

    Dapsone is approved for use in dermatitis herpetiformis and leprosy. It is particularly useful in the treatment of linear immunoglobulin (IgA) dermatosis, bullous systemic lupus erythematosus, erythema elevatum diutinum, and subcorneal pustular dermatosis.

    Brunton, L. Chabner, B, Knollman, B. Goodman and Gillman's The Pharmaceutical Basis of Therapeutics, Twelth Edition, McGraw Hill Medical, New York, NY. 2011, p. 1823

    For more Therapeutic Uses (Complete) data for DAPSONE (14 total), please visit the HSDB record page.

    4.3 Drug Warning

    Peripheral neuropathy with motor loss has been reported rarely in patients receiving high dosage of dapsone (200-500 mg daily). ... Insomnia, headache, nervousness, vertigo, and psychosis have also been reported with dapsone.

    American Society of Health-System Pharmacists 2016; Drug Information 2016. Bethesda, MD. 2016, p. 601

    Resistance to dapsone in P. falciparum, P. jiroveci, and M. leprae results primarily from mutations in genes encoding dihydropteroate synthase.

    Brunton, L. Chabner, B, Knollman, B. Goodman and Gillman's The Pharmaceutical Basis of Therapeutics, Twelth Edition, McGraw Hill Medical, New York, NY. 2011, p. 1564

    Hemolysis develops in almost every individual treated with 200-300 mg of dapsone per day. ... Methemoglobinemia is also common. A genetic deficiency in the NADH-dependent methemoglobin reductase can result in severe methemoglobinemia after administration of dapsone. Isolated instances of headache, nervousness, insomnia, blurred vision, paresthesias, reversible peripheral neuropathy (thought to be sue to axonal degeneration), drug fever, hematuria, pruritus, and a variety of skin rashes have been reported. An infectious mononucleosis-like syndrome, which may be fatal, occurs occasionally.

    Brunton, L. Chabner, B, Knollman, B. Goodman and Gillman's The Pharmaceutical Basis of Therapeutics, Twelth Edition, McGraw Hill Medical, New York, NY. 2011, p. 1564

    Glucose-6-phosphate dehydrogenase (G6PD) protects red cells against oxidative damage. However, G6PD deficiency is encountered in nearly half a billion people worldwide, the most common of 100 variants being G6PD-A-. Dapsone, an oxidant, causes severe hemolysis in patients with G6PD deficiency. Thus, G6PD deficiency testing should be performed prior to use of dapsone wherever possible.

    Brunton, L. Chabner, B, Knollman, B. Goodman and Gillman's The Pharmaceutical Basis of Therapeutics, Twelth Edition, McGraw Hill Medical, New York, NY. 2011, p. 1564

    For more Drug Warnings (Complete) data for DAPSONE (11 total), please visit the HSDB record page.

    4.4 Drug Indication

    For the treatment and management of leprosy and dermatitis herpetiformis.

    FDA Label

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Dapsone is a sulfone with anti-inflammatory immunosuppressive properties as well as antibacterial and antibiotic properties. Dapsone is the principal drug in a multidrug regimen recommended by the World Health Organization for the treatment of leprosy. As an anti-infective agent, it is also used for treating malaria and, recently, for Pneumocystic carinii pneumonia in AIDS patients. Dapsone is absorbed rapidly and nearly completely from the gastrointestinal tract. Dapsone is distributed throughout total body water and is present in all tissues. However, it tends to be retained in skin and muscle and especially in the liver and kidney: traces of the drug are present in these organs up to 3 weeks after therapy cessation.

    5.2 MeSH Pharmacological Classification

    Antimalarials

    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.)

    Leprostatic Agents

    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.)

    Anti-Infective 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.)

    Folic Acid Antagonists

    Inhibitors of the enzyme, dihydrofolate reductase (TETRAHYDROFOLATE DEHYDROGENASE), which converts dihydrofolate (FH2) to tetrahydrofolate (FH4). They are frequently used in cancer chemotherapy. (From AMA, Drug Evaluations Annual, 1994, p2033) (See all compounds classified as Folic Acid Antagonists.)

    5.3 FDA Pharmacological Classification
    5.3.1 Active Moiety
    DAPSONE
    5.3.2 FDA UNII
    8W5C518302
    5.3.3 Pharmacological Classes
    Sulfones [CS]; Sulfone [EPC]
    5.4 ATC Code

    D - Dermatologicals

    D10 - Anti-acne preparations

    D10A - Anti-acne preparations for topical use

    D10AX - Other anti-acne preparations for topical use

    D10AX05 - Dapsone

    J - Antiinfectives for systemic use

    J04 - Antimycobacterials

    J04B - Drugs for treatment of lepra

    J04BA - Drugs for treatment of lepra

    J04BA02 - Dapsone

    5.5 Absorption, Distribution and Excretion

    Absorption

    Bioavailability is 70 to 80% following oral administration.

    Route of Elimination

    Renal

    After oral administration, absorption is almost complete ... . CL increases 0.03 L/hour and Vd 0.7 L increases for each 1-kg increase in body weight above 62.3 kg. Dapsone undergoes N-acetylation by NAT2. N-oxidation to dapsone hydroxylamine is via CYP2E1, and to a lesser extent by CYP2C. Dapsone hydroxylamine enters red blood cells, leading to methemoglobin formation. Sulfones tend to be retained for up to 3 weeks in skin and muscle and especially in liver and kidney. Intestinal reabsorption of sulfones excreted in the bile contributes to long-term retention in the bloodstream; periodic interruption of treatment is advisable for this reason. Epithelial lining fluid to plasma ratio is between 0.76 and 2.91; CSF-to-plasma ration is 0.21-2.01.

    Brunton, L. Chabner, B, Knollman, B. Goodman and Gillman's The Pharmaceutical Basis of Therapeutics, Twelth Edition, McGraw Hill Medical, New York, NY. 2011, p. 1564

    Approximately 70-80% of a dose of dapsone is excreted in the urine as an acid-labile mono-N-glucuronide and mono-N-sulfamate.

    Brunton, L. Chabner, B, Knollman, B. Goodman and Gillman's The Pharmaceutical Basis of Therapeutics, Twelth Edition, McGraw Hill Medical, New York, NY. 2011, p. 1564

    Following oral administration, dapsone is rapidly and almost completely absorbed from the GI tract and peak serum concentrations of the drug are attained within 4-8 hours. ... The volume of distribution of dapsone is reportedly 1.5-2.5 L/kg in adults. Dapsone is distributed into most body tissues. Dapsone is reportedly retained in skin, muscle, kidneys, and liver; trace concentrations of the drug may be present in these tissues up to 3 weeks after discontinuance of dapsone therapy. Dapsone is also distributed into sweat, saliva, sputum, and tears, The drug is also distributed into bile. ... Dapsone crosses the placenta. Dapsone is distributed into milk. ... Dapsone is 50-90% bound to plasma proteins. The major metabolite of dapsone, monoacetyldapsone, is almost completely bound to plasms proteins.

    American Society of Health-System Pharmacists 2016; Drug Information 2016. Bethesda, MD. 2016, p. 603

    Approximately 20% of each dose of dapsone is excreted in urine as unchanged drug, 70-85% is excreted in urine as water-soluble metabolites, and a small amount is excreted in feces. Dapsone is excreted in urine as an acid-labile mono-N-glucuronide and mono-N-sulfamate derivatives in addition to some unidentified metabolites.

    American Society of Health-System Pharmacists 2016; Drug Information 2016. Bethesda, MD. 2016, p. 603

    For more Absorption, Distribution and Excretion (Complete) data for DAPSONE (8 total), please visit the HSDB record page.

    5.6 Metabolism/Metabolites

    Hepatic, mostly CYP2E1-mediated.

    Leukocyte colony forming unit cell proliferation of bone marrow was markedly suppressed by 0.1 mmol & 1.0 mmol 4'-amino-4'-hydroxylaminodiphenyl sulfone (dapsone metab) when cells were cultured for 10-14 days.

    Weetman RM et al; Br J Haematol 45 (3): 361 (1980)

    Dapsone is acetylated in the liver to monoacetyl and diacetyl derivatives. The major metabolite of dapsone is monoacetyldapsone (MADDS). The rate of acetylation of dapsone is genetically determined and is subject to interindividual variation, although the rate is usually constant for each individual. The drug also is hydroxylated in the liver to hydroxylamine dapsone (NOH-DDS). NOH-DDS appears to be responsible for methemoglobinemia and hemolysis induced by the drug.

    American Society of Health-System Pharmacists 2016; Drug Information 2016. Bethesda, MD. 2016, p. 603

    Dapsone has known human metabolites that include Monoacetyldapsone and N-Hydroxydapsone.

    S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560

    5.7 Biological Half-Life

    28 hours (range 10-50 hours)

    The elimination half-life is 20-30 hours.

    Brunton, L. Chabner, B, Knollman, B. Goodman and Gillman's The Pharmaceutical Basis of Therapeutics, Twelth Edition, McGraw Hill Medical, New York, NY. 2011, p. 1564

    There are large interindividual variations in the plasma half-life of dapsone. The plasma half-life of dapsone may range from 10-83 hours and averages 20-30 hours.

    American Society of Health-System Pharmacists 2016; Drug Information 2016. Bethesda, MD. 2016, p. 603

    5.8 Mechanism of Action

    Dapsone acts against bacteria and protozoa in the same way as sulphonamides, that is by inhibiting the synthesis of dihydrofolic acid through competition with para-amino-benzoate for the active site of dihydropteroate synthetase. The anti-inflammatory action of the drug is unrelated to its antibacterial action and is still not fully understood.

    Dapsone is a structural analog of para-aminobenzoic acid (PABA) and a competitive inhibitor of dihydropteroate synthase (folP1P2) in the folate pathway ... The effect on this evolutionarily conserved pathway also explains why dapsone is a broad-spectrum agent with antibacterial, anti-protozoal, and antifungal effects. The anti-inflammatory effects of dapsone occur via inhibition of tissue damage by neutrophils. First, dapsone inhibits neutrophil myeloperoxidase activity and respiratory burst. Second, it inhibits activity of neutrophil lysosomal enzymes. Third, it may also act as a free radical scavenger, counteracting the effect of free radicals generated by neutrophils. Fourth, dapsone may also inhibit migration of neutrophils to inflammatory lesions.

    Brunton, L. Chabner, B, Knollman, B. Goodman and Gillman's The Pharmaceutical Basis of Therapeutics, Twelth Edition, McGraw Hill Medical, New York, NY. 2011, p. 1563

    1-30 Ug/mL dapsone interfered with myeloperoxidase-H2O2-halide-mediated cytotoxic system in polymorphonuclear leukocytes. Kinetic studies revealed competitive inhibition of myeloperoxidase. Its action in dermatitis herpetiformis may be explained by effect on this system.

    Stendahl O et al; J Clin Invest 62 (1): 214 (1978)

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    07-Jan-2021
    28-Sep-2024
    KGS
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    DRUG PRODUCT COMPOSITIONS

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    DOSAGE - GEL;TOPICAL - 7.5%

    USFDA APPLICATION NUMBER - 207154

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    DOSAGE - TABLET;ORAL - 25MG

    USFDA APPLICATION NUMBER - 86841

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    DOSAGE - TABLET;ORAL - 100MG

    USFDA APPLICATION NUMBER - 86842

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