Details
Stereochemistry | ACHIRAL |
Molecular Formula | C12H12N2O2S |
Molecular Weight | 248.301 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
NC1=CC=C(C=C1)S(=O)(=O)C2=CC=C(N)C=C2
InChI
InChIKey=MQJKPEGWNLWLTK-UHFFFAOYSA-N
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
DescriptionSources: http://escholarship.org/uc/item/30m4b5krCurator's Comment: description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/nda/2005/021794s000_MicroR.pdf
Sources: http://escholarship.org/uc/item/30m4b5kr
Curator's Comment: description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/nda/2005/021794s000_MicroR.pdf
Dapsone was synthesized in 1908 by Fromm and Wittmann. The drug was approved by FDA for the treatment of such conditions as acne vulgaris, leprosy and dermatitis herpetiformis, also the drug is used off-label for many skin diseases. Although the exact mechanism of dapsone action is unknown, it is speculated that it acts as both anti-inflammatory and antimicrobial agent. It was demonstrated that dapsone suppresses ROS generation, inhibits neutrophil myeloperoxidase and eosinophil peroxidase and also inhibits bacterial dihydropteroate synthase.
CNS Activity
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL2364668 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24310318 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Curative | ACZONE Approved UseGel is indicated for the topical treatment of acne vulgaris. Launch Date-4.73385599E11 |
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Curative | DAPSONE Approved UseDermatitis herpetiformis: (D.H.) Leprosy: All forms of leprosy except for cases of proven Dapsone resistance. Launch Date2.99807998E11 |
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Curative | DAPSONE Approved UseDermatitis herpetiformis: (D.H.) Leprosy: All forms of leprosy except for cases of proven Dapsone resistance. Launch Date2.99807998E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1375 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17655376 |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
DAPSONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
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19.7 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17655376 |
110 mg 2 times / day steady-state, topical dose: 110 mg route of administration: Topical experiment type: STEADY-STATE co-administered: |
DAPSONE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
221.52 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17655376 |
110 mg 2 times / day steady-state, topical dose: 110 mg route of administration: Topical experiment type: STEADY-STATE co-administered: |
DAPSONE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
22783 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17655376 |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
DAPSONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
415 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17655376 |
110 mg 2 times / day steady-state, topical dose: 110 mg route of administration: Topical experiment type: STEADY-STATE co-administered: |
DAPSONE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
52641 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17655376 |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
DAPSONE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
20.6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17655376 |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
DAPSONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
42 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17655376 |
110 mg 2 times / day steady-state, topical dose: 110 mg route of administration: Topical experiment type: STEADY-STATE co-administered: |
DAPSONE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
10% |
unknown, unknown |
DAPSONE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
300 mg 1 times / week multiple, oral Highest studied dose Dose: 300 mg, 1 times / week Route: oral Route: multiple Dose: 300 mg, 1 times / week Sources: Page: p.1582 |
unhealthy, 38 n = 9 Health Status: unhealthy Condition: Pneumocystis pneumonia Age Group: 38 Sex: M+F Population Size: 9 Sources: Page: p.1582 |
Disc. AE: Anemia, Rash... AEs leading to discontinuation/dose reduction: Anemia (11.1%) Sources: Page: p.1582Rash (11.1%) Fever (11.1%) |
200 mg 1 times / week multiple, oral MTD Dose: 200 mg, 1 times / week Route: oral Route: multiple Dose: 200 mg, 1 times / week Sources: Page: p.1582 |
unhealthy, 38 n = 7 Health Status: unhealthy Condition: Pneumocystis pneumonia Age Group: 38 Sex: M+F Population Size: 7 Sources: Page: p.1582 |
Disc. AE: Vomiting, Fever... AEs leading to discontinuation/dose reduction: Vomiting (14.3%) Sources: Page: p.1582Fever (14.3%) |
10 g single, oral Overdose Dose: 10 g Route: oral Route: single Dose: 10 g Sources: Page: p.216 |
unhealthy, 45 n = 1 Health Status: unhealthy Condition: Dermatitis herpatiformis Age Group: 45 Sex: M Population Size: 1 Sources: Page: p.216 |
Disc. AE: Cyanosis, Methaemoglobinaemia... AEs leading to discontinuation/dose reduction: Cyanosis (acute) Sources: Page: p.216Methaemoglobinaemia Haemolysis |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Anemia | 11.1% Disc. AE |
300 mg 1 times / week multiple, oral Highest studied dose Dose: 300 mg, 1 times / week Route: oral Route: multiple Dose: 300 mg, 1 times / week Sources: Page: p.1582 |
unhealthy, 38 n = 9 Health Status: unhealthy Condition: Pneumocystis pneumonia Age Group: 38 Sex: M+F Population Size: 9 Sources: Page: p.1582 |
Fever | 11.1% Disc. AE |
300 mg 1 times / week multiple, oral Highest studied dose Dose: 300 mg, 1 times / week Route: oral Route: multiple Dose: 300 mg, 1 times / week Sources: Page: p.1582 |
unhealthy, 38 n = 9 Health Status: unhealthy Condition: Pneumocystis pneumonia Age Group: 38 Sex: M+F Population Size: 9 Sources: Page: p.1582 |
Rash | 11.1% Disc. AE |
300 mg 1 times / week multiple, oral Highest studied dose Dose: 300 mg, 1 times / week Route: oral Route: multiple Dose: 300 mg, 1 times / week Sources: Page: p.1582 |
unhealthy, 38 n = 9 Health Status: unhealthy Condition: Pneumocystis pneumonia Age Group: 38 Sex: M+F Population Size: 9 Sources: Page: p.1582 |
Fever | 14.3% Disc. AE |
200 mg 1 times / week multiple, oral MTD Dose: 200 mg, 1 times / week Route: oral Route: multiple Dose: 200 mg, 1 times / week Sources: Page: p.1582 |
unhealthy, 38 n = 7 Health Status: unhealthy Condition: Pneumocystis pneumonia Age Group: 38 Sex: M+F Population Size: 7 Sources: Page: p.1582 |
Vomiting | 14.3% Disc. AE |
200 mg 1 times / week multiple, oral MTD Dose: 200 mg, 1 times / week Route: oral Route: multiple Dose: 200 mg, 1 times / week Sources: Page: p.1582 |
unhealthy, 38 n = 7 Health Status: unhealthy Condition: Pneumocystis pneumonia Age Group: 38 Sex: M+F Population Size: 7 Sources: Page: p.1582 |
Haemolysis | Disc. AE | 10 g single, oral Overdose Dose: 10 g Route: oral Route: single Dose: 10 g Sources: Page: p.216 |
unhealthy, 45 n = 1 Health Status: unhealthy Condition: Dermatitis herpatiformis Age Group: 45 Sex: M Population Size: 1 Sources: Page: p.216 |
Methaemoglobinaemia | Disc. AE | 10 g single, oral Overdose Dose: 10 g Route: oral Route: single Dose: 10 g Sources: Page: p.216 |
unhealthy, 45 n = 1 Health Status: unhealthy Condition: Dermatitis herpatiformis Age Group: 45 Sex: M Population Size: 1 Sources: Page: p.216 |
Cyanosis | acute Disc. AE |
10 g single, oral Overdose Dose: 10 g Route: oral Route: single Dose: 10 g Sources: Page: p.216 |
unhealthy, 45 n = 1 Health Status: unhealthy Condition: Dermatitis herpatiformis Age Group: 45 Sex: M Population Size: 1 Sources: Page: p.216 |
PubMed
Title | Date | PubMed |
---|---|---|
[Granulomatous hepatitis caused by dapsone]. | 1992 |
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Treatment of experimental pneumocystosis: review of 7 years of experience and development of a new system for classifying antimicrobial drugs. | 1992 Sep |
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Application of higher throughput screening (HTS) inhibition assays to evaluate the interaction of antiparasitic drugs with cytochrome P450s. | 2001 Jan |
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Chlorproguanil-dapsone for treatment of drug-resistant falciparum malaria in Tanzania. | 2001 Oct 13 |
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[Dapsona syndrome]. | 2002 Jul |
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Dapsone. | 2002 Jun |
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In vitro activities of pentamidine, pyrimethamine, trimethoprim, and sulfonamides against Aspergillus species. | 2002 Jun |
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Cytochrome P450 1A1/2 induction by antiparasitic drugs: dose-dependent increase in ethoxyresorufin O-deethylase activity and mRNA caused by quinine, primaquine and albendazole in HepG2 cells. | 2002 Nov |
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Synthesis and evaluation of analogues of Congo red as potential compounds against transmissible spongiform encephalopathies. | 2003 Jun |
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[Treatment of relapsing polychondritis]. | 2003 Mar |
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Prediction of genotoxicity of chemical compounds by statistical learning methods. | 2005 Jun |
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A case of drug-induced hypersensitivity syndrome with multiple organ involvement treated with plasma exchange. | 2005 Oct |
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Acute methemoglobinemia following attempted suicide by Dapson. | 2006 Apr |
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[Disulone and hepatosiderosis]. | 2006 Aug-Sep |
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Role of human cyclooxygenase-2 in the bioactivation of dapsone and sulfamethoxazole. | 2006 Jan |
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[Refractory cutaneous necrotizing vasculitis. Successful sulfone therapy]. | 2006 Jan |
Patents
Sample Use Guides
In Vivo Use Guide
Curator's Comment: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=7fc98c9b-b17a-f66f-055b-259207ad9504
Apply 5% gel to the acne affected areas twice a day (Aczone gel). In dermatitis herpetiformis, the starting oral dose is 50 mg and in leprosy, the dose is 100 mg/day (Dapsone oral formulation).
Route of Administration:
Other
With Staphylococcus aureus (both methicillin-susceptible S. aureus-MSSA and methicillinresistant S. aureus-MRSA), dapsone MIC50, MIC90 were 128 ug/mL and 256 ug/mL, respectively. For Staphylococcus epidermidis overall, dapsone MIC50, MIC90 were 128 ug/mL and 256 ug/mL, respectively. Overall results with Enterococcus faecalis, dapsone MIC50, MIC90 were 256 ug/mL and 512 ug/mL, respectively. With Streptococcus agalactiae, dapsone MIC50, MIC90 were reported overall to be 32 ug/mL and 256 ug/mL, respectively. For Streptococcus pyogenes, dapsone MIC50, MIC90 were 32 ug/mL and 512 ug/mL, respectively.
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Classification Tree | Code System | Code | ||
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NDF-RT |
N0000008053
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NCI_THESAURUS |
C849
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WHO-VATC |
QD10AX05
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WHO-ESSENTIAL MEDICINES LIST |
6.2.3
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WHO-ATC |
J04BA02
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WHO-VATC |
QJ04BA02
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WHO-ATC |
D10AX05
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FDA ORPHAN DRUG |
85694
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NDF-RT |
N0000175881
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NDF-RT |
N0000008053
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FDA ORPHAN DRUG |
61291
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EPA PESTICIDE CODE |
690107
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LIVERTOX |
NBK548936
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FDA ORPHAN DRUG |
61191
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8W5C518302
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5073
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D003622
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2955
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SUB06909MIG
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CHEMBL1043
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8W5C518302
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80-08-0
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3108
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782
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201-248-4
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M4092
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100000083461
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1164008
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4325
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DAPSONE
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PRIMARY | Description: A white or creamy white, crystalline powder; odourless. Solubility: Soluble in 7000 parts of water and in 30 parts of ethanol (~750 g/l) TS; soluble in acetone R.Category: Antileprotic. Storage: Dapsone should be kept in a tightly closed container, protected from light. Additional information: Even in the absence of light, Dapsone is gradually degraded on exposure to a humid atmosphere, thedecomposition being faster at higher temperatures. | ||
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DAPSONE
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Dapsone
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DB00250
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6091
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C415
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DTXSID4020371
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ACTIVE MOIETY
METABOLITE (PARENT)
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METABOLITE TOXIC (PARENT)