dapsone Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
antimycobacterials, diaminodiphenylsulfone derivatives 782 80-08-0

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • dapsone
  • diaphenylsulfon
  • diaphenylsulfone
  • sulphadione
  • dapson
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)
  • Molecular weight: 248.30
  • Formula: C12H12N2O2S
  • CLOGP: 0.89
  • LIPINSKI: 0
  • HAC: 4
  • HDO: 2
  • TPSA: 86.18
  • ALOGS: -2.94
  • ROTB: 2

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
50 mg O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 2 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 0.20 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 15 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 20.14 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 93 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 0.83 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 0.48 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.25 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 22 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
July 3, 1979 FDA JACOBUS

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Methaemoglobinaemia 632.64 44.44 79 449 260 2357297
Drug reaction with eosinophilia and systemic symptoms 325.70 44.44 65 463 5453 2352104
Drug ineffective 151.71 44.44 69 459 101555 2256002
Haemolytic anaemia 103.18 44.44 21 507 1860 2355697
Treatment failure 93.75 44.44 25 503 7214 2350343
Leukopenia 80.87 44.44 24 504 10172 2347385
Acne 65.86 44.44 16 512 3160 2354397
Cyanosis 55.70 44.44 14 514 3171 2354386
Skin exfoliation 51.84 44.44 15 513 5775 2351782
Urticaria 50.15 44.44 21 507 24240 2333317
Drug-induced liver injury 48.82 44.44 13 515 3686 2353871
Blood methaemoglobin present 48.03 44.44 6 522 18 2357539
Pyrexia 47.79 44.44 26 502 53682 2303875
Sepsis 44.98 44.44 18 510 18470 2339087

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Drug reaction with eosinophilia and systemic symptoms 351.15 61.69 71 345 4999 1741366
Methaemoglobinaemia 327.08 61.69 46 370 318 1746047
Type 2 lepra reaction 165.92 61.69 21 395 52 1746313
Haemolytic anaemia 115.25 61.69 24 392 1838 1744527
Vanishing bile duct syndrome 109.52 61.69 16 400 143 1746222
Pyrexia 67.83 61.69 34 382 46366 1699999

Pharmacologic Action:

SourceCodeDescription
ATC D10AX05 DERMATOLOGICALS
ANTI-ACNE PREPARATIONS
ANTI-ACNE PREPARATIONS FOR TOPICAL USE
Other anti-acne preparations for topical use
ATC J04BA02 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIMYCOBACTERIALS
DRUGS FOR TREATMENT OF LEPRA
Drugs for treatment of lepra
FDA EPC N0000175881 Sulfone
FDA Chemical/Ingredient N0000008053 Sulfones
CHEBI has role CHEBI:38068 antimalarial
CHEBI has role CHEBI:35816 leprostatic drug
CHEBI has role CHEBI:35441 antiinfective agent
CHEBI has role CHEBI:35472 anti-inflammatory drug
MeSH PA D000900 Anti-Bacterial Agents
MeSH PA D000890 Anti-Infective Agents
MeSH PA D000962 Antimalarials
MeSH PA D000977 Antiparasitic Agents
MeSH PA D000981 Antiprotozoal Agents
MeSH PA D004791 Enzyme Inhibitors
MeSH PA D005493 Folic Acid Antagonists
MeSH PA D007917 Leprostatic Agents

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Leprosy indication 81004002 DOID:1024
Acne vulgaris indication 88616000
Dermatitis herpetiformis indication 111196000 DOID:8505
Subcorneal pustular dermatosis off-label use 25147002 DOID:8508
Benign mucous membrane pemphigoid off-label use 34250006 DOID:11656
Systemic lupus erythematosus off-label use 55464009 DOID:9074
Granuloma annulare off-label use 65508009 DOID:3777
Pyoderma gangrenosum off-label use 74578003 DOID:8553
Pemphigoid off-label use 86142006
Actinomycotic mycetoma off-label use 187089001
Toxoplasmosis off-label use 187192000 DOID:9965
Pneumocystosis jiroveci pneumonia off-label use 415125002 DOID:11339
Pneumocystis Carinii Pneumonia Prevention off-label use
Anemia due to enzyme deficiency contraindication 111577008
Deficiency of glucose-6-phosphate dehydrogenase contraindication 124134002 DOID:2862
Deficiency of cytochrome-b>5< reductase contraindication 124184009
Disease of liver contraindication 235856003 DOID:409
Anemia contraindication 271737000 DOID:2355

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 2.34 Basic
pKa2 1.73 Basic

Orange Book patent data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent use
7.5% ACZONE ALMIRALL N207154 Feb. 24, 2016 RX GEL TOPICAL 9517219 Nov. 18, 2033 TOPICAL TREATMENT OF ACNE VULGARIS

Orange Book exclusivity data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRouteExclusivity dateDescription
7.5% ACZONE ALMIRALL N207154 Feb. 24, 2016 RX GEL TOPICAL Sept. 10, 2022 NEW PATIENT POPULATION

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
5-hydroxytryptamine receptor 6 GPCR Ki 6.74 CHEMBL
Cytochrome P450 3A4 Enzyme Ki 4.57 WOMBAT-PK
Glucose-6-phosphate 1-dehydrogenase Enzyme WOMBAT-PK
Dihydropteroate synthase 1 Enzyme INHIBITOR IC50 5.90 WOMBAT-PK CHEMBL
Dihydrofolate reductase Enzyme IC50 5.82 CHEMBL
Dihydropteroate synthetase, putative Unclassified IC50 4.91 CHEMBL

External reference:

IDSource
D003622 MESH_DESCRIPTOR_UI
4019264 VUID
N0000147467 NUI
C0010980 UMLSCUI
D00592 KEGG_DRUG
17308007 SNOMEDCT_US
4019264 VANDF
003003 NDDF
682 MMSL
3108 RXNORM
387096002 SNOMEDCT_US
4536 MMSL
d00098 MMSL
8W5C518302 UNII
1676 INN_ID
2955 PUBCHEM_CID
CHEBI:4325 CHEBI
CHEMBL1043 ChEMBL_ID
DB00250 DRUGBANK_ID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
ACZONE HUMAN PRESCRIPTION DRUG LABEL 1 0023-3670 GEL 50 mg TOPICAL NDA 16 sections
ACZONE HUMAN PRESCRIPTION DRUG LABEL 1 0023-5206 GEL 75 mg TOPICAL NDA 16 sections
DAPSONE HUMAN PRESCRIPTION DRUG LABEL 1 0904-7018 TABLET 100 mg ORAL ANDA 11 sections
DAPSONE HUMAN PRESCRIPTION DRUG LABEL 1 0904-7019 TABLET 25 mg ORAL ANDA 11 sections
DAPSONE HUMAN PRESCRIPTION DRUG LABEL 1 10135-654 TABLET 25 mg ORAL ANDA 13 sections
DAPSONE HUMAN PRESCRIPTION DRUG LABEL 1 10135-655 TABLET 100 mg ORAL ANDA 13 sections
Dapsone HUMAN PRESCRIPTION DRUG LABEL 1 13925-504 TABLET 25 mg ORAL ANDA 13 sections
Dapsone HUMAN PRESCRIPTION DRUG LABEL 1 13925-505 TABLET 100 mg ORAL ANDA 13 sections
Aczone HUMAN PRESCRIPTION DRUG LABEL 1 16110-526 GEL 75 mg TOPICAL NDA 17 sections
Dapsone HUMAN PRESCRIPTION DRUG LABEL 1 16714-956 GEL 50 mg TOPICAL ANDA 17 sections
Dapsone HUMAN PRESCRIPTION DRUG LABEL 1 29033-036 TABLET 25 mg ORAL ANDA 13 sections
Dapsone HUMAN PRESCRIPTION DRUG LABEL 1 29033-037 TABLET 100 mg ORAL ANDA 13 sections
Dapsone HUMAN PRESCRIPTION DRUG LABEL 1 42291-298 TABLET 25 mg ORAL ANDA 13 sections
Dapsone HUMAN PRESCRIPTION DRUG LABEL 1 42291-299 TABLET 100 mg ORAL ANDA 13 sections
Dapsone HUMAN PRESCRIPTION DRUG LABEL 1 43353-222 TABLET 25 mg ORAL ANDA 13 sections
Dapsone HUMAN PRESCRIPTION DRUG LABEL 1 43353-223 TABLET 100 mg ORAL ANDA 13 sections
Dapsone HUMAN PRESCRIPTION DRUG LABEL 1 47781-333 TABLET 25 mg ORAL ANDA 13 sections
Dapsone HUMAN PRESCRIPTION DRUG LABEL 1 47781-334 TABLET 100 mg ORAL ANDA 13 sections
Dapsone HUMAN PRESCRIPTION DRUG LABEL 1 49938-101 TABLET 100 mg ORAL ANDA 13 sections
Dapsone HUMAN PRESCRIPTION DRUG LABEL 1 49938-102 TABLET 25 mg ORAL ANDA 13 sections
Dapsone HUMAN PRESCRIPTION DRUG LABEL 1 51672-1387 GEL 50 mg TOPICAL ANDA 17 sections
Dapsone HUMAN PRESCRIPTION DRUG LABEL 1 51672-1388 GEL 75 mg TOPICAL ANDA 18 sections
Dapsone HUMAN PRESCRIPTION DRUG LABEL 1 51672-4197 TABLET 25 mg ORAL ANDA 13 sections
Dapsone HUMAN PRESCRIPTION DRUG LABEL 1 51672-4198 TABLET 100 mg ORAL ANDA 13 sections
Dapsone HUMAN PRESCRIPTION DRUG LABEL 1 51672-5307 GEL 75 mg TOPICAL NDA 16 sections
Dapsone HUMAN PRESCRIPTION DRUG LABEL 1 54868-2817 TABLET 25 mg ORAL ANDA 13 sections
Dapsone HUMAN PRESCRIPTION DRUG LABEL 1 54868-3801 TABLET 100 mg ORAL ANDA 13 sections
Dapsone HUMAN PRESCRIPTION DRUG LABEL 1 55695-005 TABLET 25 mg ORAL ANDA 13 sections
Dapsone HUMAN PRESCRIPTION DRUG LABEL 1 55695-025 TABLET 100 mg ORAL ANDA 13 sections
Dapsone HUMAN PRESCRIPTION DRUG LABEL 1 60429-495 TABLET 25 mg ORAL ANDA 13 sections