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 540.28 15.64 112 7114 2050 46676786
Drug reaction with eosinophilia and systemic symptoms 254.80 15.64 113 7113 29435 46649401
Haemolytic anaemia 133.28 15.64 52 7174 9790 46669046
Blood methaemoglobin present 51.02 15.64 9 7217 65 46678771
Type 2 lepra reaction 42.22 15.64 7 7219 33 46678803
Off label use 41.61 15.64 141 7085 379700 46299136
Treatment failure 40.15 15.64 60 7166 93027 46585809
Skin odour abnormal 39.41 15.64 13 7213 1506 46677330
Hidradenitis 35.20 15.64 13 7213 2102 46676734
Hepatitis fulminant 32.47 15.64 14 7212 3388 46675448
Idiopathic pneumonia syndrome 31.53 15.64 8 7218 364 46678472
Type IIb hyperlipidaemia 29.15 15.64 5 7221 30 46678806
Wound secretion 27.59 15.64 13 7213 3867 46674969
Haemolysis 27.54 15.64 15 7211 6044 46672792
Sepsis 27.23 15.64 63 7163 135951 46542885
Pseudomonas infection 25.68 15.64 17 7209 9741 46669095
Drug ineffective 25.30 15.64 185 7041 677653 46001183
Myopathy 24.66 15.64 16 7210 8865 46669971
Thyroid tuberculosis 23.61 15.64 4 7222 22 46678814
Klebsiella infection 23.56 15.64 14 7212 6648 46672188
Product use in unapproved indication 22.86 15.64 46 7180 90227 46588609
Skin lesion 22.37 15.64 24 7202 26689 46652147
Eosinophilic myocarditis 21.92 15.64 6 7220 367 46678469
Skin hyperpigmentation 21.06 15.64 12 7214 5270 46673566
Pyrexia 20.38 15.64 107 7119 348695 46330141
Cyanosis 20.23 15.64 18 7208 15953 46662883
Dermatitis herpetiformis 20.03 15.64 3 7223 6 46678830
Leukopenia 19.96 15.64 37 7189 68306 46610530
Drug-induced liver injury 19.86 15.64 22 7204 25346 46653490
Marrow hyperplasia 19.60 15.64 6 7220 546 46678290
Oxygen saturation decreased 18.41 15.64 36 7190 69128 46609708
Angioedema 17.86 15.64 26 7200 39316 46639520
Bronchopulmonary aspergillosis 17.20 15.64 12 7214 7484 46671352
Choriomeningitis lymphocytic 16.96 15.64 3 7223 22 46678814
Acne 16.86 15.64 18 7208 19901 46658935
Skin exfoliation 16.77 15.64 23 7203 32915 46645921
Rash 16.00 15.64 102 7124 356410 46322426

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
Methaemoglobinaemia 205.49 16.02 58 7416 2452 29942552
Type 2 lepra reaction 165.55 16.02 34 7440 353 29944651
Drug reaction with eosinophilia and systemic symptoms 161.53 16.02 96 7378 28392 29916612
Haemolytic anaemia 99.49 16.02 49 7425 9961 29935043
Vanishing bile duct syndrome 85.62 16.02 22 7452 646 29944358
Type 1 lepra reaction 55.46 16.02 9 7465 19 29944985
Brain abscess 52.07 16.02 21 7453 2660 29942344
Mycobacterium avium complex infection 48.43 16.02 20 7454 2691 29942313
Pleocytosis 48.28 16.02 13 7461 459 29944545
Lepromatous leprosy 44.67 16.02 9 7465 84 29944920
Pyrexia 42.52 16.02 165 7309 294324 29650680
Nocardiosis 37.58 16.02 18 7456 3437 29941567
HIV associated nephropathy 35.09 16.02 9 7465 262 29944742
Blood methaemoglobin present 33.74 16.02 6 7468 26 29944978
Haemolysis 32.37 16.02 21 7453 7210 29937794
Drug-induced liver injury 30.84 16.02 32 7442 21242 29923762
Toxoplasmosis 30.45 16.02 11 7463 1032 29943972
Pancytopenia 29.11 16.02 65 7409 84987 29860017
Papillary cystadenoma lymphomatosum 25.97 16.02 5 7469 36 29944968
Mucormycosis 25.32 16.02 16 7458 5252 29939752
Leprosy 25.27 16.02 6 7468 126 29944878
Aeromonas infection 25.15 16.02 7 7467 280 29944724
Induration 24.89 16.02 9 7465 847 29944157
Thrombotic microangiopathy 24.58 16.02 19 7455 8591 29936413
Disseminated cryptococcosis 23.45 16.02 9 7465 1000 29944004
Pneumonia cryptococcal 22.49 16.02 8 7466 718 29944286
Photophobia 21.45 16.02 15 7459 5821 29939183
Cushingoid 21.25 16.02 11 7463 2476 29942528
Pemphigoid 20.17 16.02 16 7458 7512 29937492
Epstein-Barr virus infection 19.58 16.02 15 7459 6691 29938313
Death 18.92 16.02 38 7436 357245 29587759
Fluid imbalance 18.86 16.02 6 7468 382 29944622
Granuloma 18.79 16.02 10 7464 2382 29942622
Tuberculoid leprosy 18.57 16.02 4 7470 53 29944951
Graft versus host disease 17.91 16.02 17 7457 10133 29934871
Neuritis 16.99 16.02 6 7468 527 29944477
Thrombocytopenia 16.66 16.02 73 7401 136971 29808033

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 CS M0020791 Sulfones
CHEBI has role CHEBI:35441 anti-infective drugs
CHEBI has role CHEBI:35472 anti-inflammatory drugs
CHEBI has role CHEBI:35816 leprostatic
CHEBI has role CHEBI:38068 antimalarials
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
FDA EPC N0000175881 Sulfone

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)

None

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
4019264 VUID
N0000147467 NUI
D00592 KEGG_DRUG
4019264 VANDF
C0010980 UMLSCUI
CHEBI:4325 CHEBI
CHEMBL1043 ChEMBL_ID
DB00250 DRUGBANK_ID
D003622 MESH_DESCRIPTOR_UI
2955 PUBCHEM_CID
10934 IUPHAR_LIGAND_ID
1676 INN_ID
8W5C518302 UNII
3108 RXNORM
4536 MMSL
682 MMSL
d00098 MMSL
003003 NDDF
17308007 SNOMEDCT_US
387096002 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
ACZONE HUMAN PRESCRIPTION DRUG LABEL 1 0023-3670 GEL 50 mg TOPICAL NDA 26 sections
ACZONE7.5 HUMAN PRESCRIPTION DRUG LABEL 1 0023-5206 GEL 75 mg TOPICAL NDA 25 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 19 sections
DAPSONE HUMAN PRESCRIPTION DRUG LABEL 1 10135-655 TABLET 100 mg ORAL ANDA 19 sections
Dapsone HUMAN PRESCRIPTION DRUG LABEL 1 13925-504 TABLET 25 mg ORAL ANDA 19 sections
Dapsone HUMAN PRESCRIPTION DRUG LABEL 1 13925-505 TABLET 100 mg ORAL ANDA 19 sections
Aczone HUMAN PRESCRIPTION DRUG LABEL 1 16110-526 GEL 75 mg TOPICAL NDA 26 sections
Dapsone HUMAN PRESCRIPTION DRUG LABEL 1 16714-956 GEL 50 mg TOPICAL ANDA 26 sections
Dapsone HUMAN PRESCRIPTION DRUG LABEL 1 29033-036 TABLET 25 mg ORAL ANDA 18 sections
Dapsone HUMAN PRESCRIPTION DRUG LABEL 1 29033-037 TABLET 100 mg ORAL ANDA 18 sections
Dapsone HUMAN PRESCRIPTION DRUG LABEL 1 42291-298 TABLET 25 mg ORAL ANDA 21 sections
Dapsone HUMAN PRESCRIPTION DRUG LABEL 1 42291-299 TABLET 100 mg ORAL ANDA 21 sections
Dapsone HUMAN PRESCRIPTION DRUG LABEL 1 43353-222 TABLET 25 mg ORAL ANDA 21 sections
Dapsone HUMAN PRESCRIPTION DRUG LABEL 1 43353-223 TABLET 100 mg ORAL ANDA 21 sections
Dapsone HUMAN PRESCRIPTION DRUG LABEL 1 47781-333 TABLET 25 mg ORAL ANDA 19 sections
Dapsone HUMAN PRESCRIPTION DRUG LABEL 1 47781-334 TABLET 100 mg ORAL ANDA 19 sections
Dapsone HUMAN PRESCRIPTION DRUG LABEL 1 49938-101 TABLET 100 mg ORAL ANDA 18 sections
Dapsone HUMAN PRESCRIPTION DRUG LABEL 1 49938-101 TABLET 100 mg ORAL ANDA 18 sections
Dapsone HUMAN PRESCRIPTION DRUG LABEL 1 49938-102 TABLET 25 mg ORAL ANDA 18 sections
Dapsone HUMAN PRESCRIPTION DRUG LABEL 1 49938-102 TABLET 25 mg ORAL ANDA 18 sections
Dapsone HUMAN PRESCRIPTION DRUG LABEL 1 51672-1387 GEL 50 mg TOPICAL ANDA 26 sections
Dapsone HUMAN PRESCRIPTION DRUG LABEL 1 51672-1388 GEL 75 mg TOPICAL ANDA 27 sections
Dapsone HUMAN PRESCRIPTION DRUG LABEL 1 51672-4197 TABLET 25 mg ORAL ANDA 20 sections
Dapsone HUMAN PRESCRIPTION DRUG LABEL 1 51672-4198 TABLET 100 mg ORAL ANDA 20 sections
Dapsone HUMAN PRESCRIPTION DRUG LABEL 1 51672-5307 GEL 75 mg TOPICAL NDA authorized generic 26 sections
Dapsone HUMAN PRESCRIPTION DRUG LABEL 1 54868-2817 TABLET 25 mg ORAL ANDA 18 sections
Dapsone HUMAN PRESCRIPTION DRUG LABEL 1 54868-3801 TABLET 100 mg ORAL ANDA 18 sections
Dapsone HUMAN PRESCRIPTION DRUG LABEL 1 55695-005 TABLET 25 mg ORAL ANDA 18 sections