dapsone ๐Ÿถ Veterinary Use | 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 ยตM/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 586.24 16.06 119 7830 1923 50595252
Drug reaction with eosinophilia and systemic symptoms 293.55 16.06 124 7825 28300 50568875
Haemolytic anaemia 131.85 16.06 51 7898 9241 50587934
Blood methaemoglobin present 51.38 16.06 9 7940 61 50597114
Type 2 lepra reaction 50.27 16.06 8 7941 27 50597148
Off label use 46.99 16.06 172 7777 474254 50122921
Skin odour abnormal 39.62 16.06 13 7936 1459 50595716
Drug ineffective 35.31 16.06 234 7715 819099 49778076
Myopathy 34.14 16.06 20 7929 9119 50588056
Hepatitis fulminant 33.66 16.06 14 7935 3054 50594121
Haemolysis 33.09 16.06 17 7932 5999 50591176
Idiopathic pneumonia syndrome 32.13 16.06 8 7941 332 50596843
Sepsis 29.82 16.06 65 7884 132860 50464315
Treatment failure 29.40 16.06 66 7883 137571 50459604
Type IIb hyperlipidaemia 29.07 16.06 5 7944 30 50597145
Wound secretion 27.60 16.06 13 7936 3804 50593371
Drug-induced liver injury 26.35 16.06 27 7922 28068 50569107
Skin lesion 23.83 16.06 25 7924 26702 50570473
Pseudomonas infection 23.57 16.06 16 7933 9414 50587761
Thyroid tuberculosis 23.55 16.06 4 7945 22 50597153
Product use in unapproved indication 23.02 16.06 54 7895 115765 50481410
Klebsiella infection 22.38 16.06 14 7935 7180 50589995
Skin exfoliation 22.37 16.06 27 7922 33585 50563590
Congenital hydrocephalus 22.09 16.06 5 7944 137 50597038
Eosinophilic myocarditis 21.96 16.06 6 7943 359 50596816
Leukopenia 21.14 16.06 38 7911 67490 50529685
Skin hyperpigmentation 20.91 16.06 12 7937 5264 50591911
Cyanosis 20.78 16.06 18 7931 15166 50582009
Dermatitis herpetiformis 19.67 16.06 3 7946 7 50597168
Marrow hyperplasia 19.25 16.06 6 7943 571 50596604
Drug ineffective for unapproved indication 19.14 16.06 20 7929 21261 50575914
Oxygen saturation decreased 18.95 16.06 38 7911 73210 50523965
Cushingoid 18.36 16.06 12 7937 6633 50590542
Abdominal discomfort 17.90 16.06 7 7942 231634 50365541
Pyrexia 17.69 16.06 111 7838 380092 50217083
Rash erythematous 16.97 16.06 24 7925 34828 50562347
Bronchopulmonary aspergillosis 16.91 16.06 12 7937 7580 50589595
Choriomeningitis lymphocytic 16.58 16.06 3 7946 25 50597150
Joint swelling 16.50 16.06 9 7940 245277 50351898
Methylobacterium infection 16.37 16.06 3 7946 27 50597148
Scar 16.15 16.06 14 7935 11804 50585371
Calciphylaxis 16.10 16.06 8 7941 2630 50594545

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 258.58 16.61 72 8130 2599 29563726
Drug reaction with eosinophilia and systemic symptoms 174.21 16.61 104 8098 27888 29538437
Type 2 lepra reaction 148.86 16.61 28 8174 155 29566170
Haemolytic anaemia 100.34 16.61 50 8152 9369 29556956
Vanishing bile duct syndrome 91.02 16.61 23 8179 565 29565760
Type 1 lepra reaction 71.86 16.61 12 8190 28 29566297
Brain abscess 50.12 16.61 21 8181 2634 29563691
Mycobacterium avium complex infection 49.83 16.61 20 8182 2249 29564076
Drug-induced liver injury 47.74 16.61 43 8159 21612 29544713
Pleocytosis 46.68 16.61 13 8189 468 29565857
Pyrexia 46.06 16.61 179 8023 287443 29278882
Nocardiosis 36.76 16.61 18 8184 3242 29563083
Haemolysis 33.50 16.61 22 8180 6934 29559391
Blood methaemoglobin present 33.50 16.61 6 8196 24 29566301
HIV associated nephropathy 33.30 16.61 9 8193 289 29566036
Aeromonas infection 29.84 16.61 8 8194 249 29566076
Toxoplasmosis 28.12 16.61 11 8191 1156 29565169
Pancytopenia 26.57 16.61 66 8136 83102 29483223
Fluid imbalance 25.60 16.61 7 8195 235 29566090
Papillary cystadenoma lymphomatosum 25.44 16.61 5 8197 36 29566289
Photophobia 24.20 16.61 17 8185 5978 29560347
Mucormycosis 24.08 16.61 16 8186 5142 29561183
Induration 23.76 16.61 9 8193 867 29565458
Hypoxia 23.60 16.61 45 8157 47334 29518991
Mycobacterium abscessus infection 21.26 16.61 7 8195 447 29565878
Disseminated cryptococcosis 21.18 16.61 9 8193 1169 29565156
Pneumonia cryptococcal 21.14 16.61 8 8194 768 29565557
Epstein-Barr virus infection 20.47 16.61 16 8186 6613 29559712
Cushingoid 20.36 16.61 11 8191 2427 29563898
Autoinflammatory disease 18.08 16.61 4 8198 54 29566271
Granuloma 17.52 16.61 10 8192 2454 29563871
Disseminated mycobacterium avium complex infection 17.45 16.61 4 8198 64 29566261
Graft versus host disease 17.15 16.61 17 8185 9611 29556714
Necrotising fasciitis 17.08 16.61 11 8191 3354 29562971

FDA Adverse Event Reporting System (Geriatric)

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 711.43 13.65 169 13688 4179 64480696
Drug reaction with eosinophilia and systemic symptoms 463.47 13.65 228 13629 53989 64430886
Haemolytic anaemia 223.76 13.65 95 13762 15958 64468917
Type 2 lepra reaction 184.72 13.65 33 13824 177 64484698
Type 1 lepra reaction 86.72 13.65 14 13843 35 64484840
Vanishing bile duct syndrome 83.61 13.65 24 13833 1253 64483622
Blood methaemoglobin present 81.97 13.65 15 13842 94 64484781
Drug-induced liver injury 76.88 13.65 71 13786 47572 64437303
Haemolysis 56.29 13.65 33 13824 11006 64473869
Pyrexia 54.09 13.65 250 13607 558394 63926481
Nocardiosis 49.61 13.65 23 13834 4744 64480131
Brain abscess 46.10 13.65 21 13836 4160 64480715
Treatment failure 42.70 13.65 84 13773 116732 64368143
Pseudomonas infection 39.70 13.65 32 13825 17851 64467024
Pancytopenia 39.63 13.65 92 13765 143217 64341658
Drug ineffective 39.31 13.65 311 13546 839936 63644939
Pleocytosis 39.26 13.65 13 13844 1094 64483781
Cushingoid 36.86 13.65 22 13835 7581 64477294
HIV associated nephropathy 35.49 13.65 9 13848 292 64484583
Hypoxia 34.17 13.65 65 13792 88084 64396791
Product use in unapproved indication 32.11 13.65 97 13760 176521 64308354
Mycobacterium avium complex infection 31.88 13.65 16 13841 3924 64480951
Aeromonas infection 29.62 13.65 8 13849 333 64484542
Skin exfoliation 29.48 13.65 42 13815 44843 64440032
Drug ineffective for unapproved indication 28.00 13.65 34 13823 31099 64453776
Type IIb hyperlipidaemia 27.51 13.65 5 13852 30 64484845
Myopathy 25.92 13.65 25 13832 17655 64467220
Skin odour abnormal 25.83 13.65 11 13846 1856 64483019
Off label use 25.63 13.65 227 13630 632579 63852296
Sepsis 25.12 13.65 107 13750 230234 64254641
Mucormycosis 25.01 13.65 17 13840 7324 64477551
Epstein-Barr virus infection 24.91 13.65 21 13836 12467 64472408
Skin lesion 23.75 13.65 34 13823 36448 64448427
Induration 23.67 13.65 10 13847 1654 64483221
Fluid imbalance 23.32 13.65 7 13850 427 64484448
Pneumocystis jirovecii pneumonia 22.95 13.65 29 13828 27605 64457270
Leukopenia 22.69 13.65 60 13797 101182 64383693
Anaemia 22.08 13.65 148 13709 378532 64106343
Cutaneous lupus erythematosus 22.02 13.65 11 13846 2671 64482204
Thyroid tuberculosis 22.01 13.65 4 13853 24 64484851
Papillary cystadenoma lymphomatosum 21.94 13.65 5 13852 102 64484773
Idiopathic pneumonia syndrome 21.70 13.65 7 13850 542 64484333
Leukocytosis 21.45 13.65 33 13824 37707 64447168
Therapy non-responder 21.23 13.65 45 13812 65854 64419021
Antineutrophil cytoplasmic antibody positive 21.06 13.65 8 13849 1004 64483871
Disseminated cryptococcosis 20.91 13.65 9 13848 1558 64483317
Hepatitis fulminant 20.12 13.65 14 13843 6260 64478615
Toxoplasmosis 20.00 13.65 10 13847 2434 64482441
Rash maculo-papular 19.87 13.65 36 13821 46990 64437885
Staphylococcal bacteraemia 19.80 13.65 17 13840 10338 64474537
Necrotising fasciitis 19.74 13.65 13 13844 5313 64479562
Cyanosis 19.60 13.65 24 13833 22131 64462744
Joint swelling 19.52 13.65 11 13846 215371 64269504
Pneumonia cryptococcal 19.49 13.65 8 13849 1231 64483644
Jaundice 19.07 13.65 36 13821 48476 64436399
Mucocutaneous leishmaniasis 19.03 13.65 6 13851 432 64484443
Eosinophilic myocarditis 18.69 13.65 7 13850 845 64484030
Respiratory failure 18.43 13.65 76 13781 161107 64323768
Pneumonia 18.30 13.65 192 13665 559384 63925491
Pain in extremity 18.24 13.65 23 13834 303062 64181813
Wound secretion 17.54 13.65 12 13845 5220 64479655
Mycobacterium abscessus infection 17.51 13.65 7 13850 1007 64483868
Graft versus host disease 17.42 13.65 18 13839 13795 64471080
Pain 17.32 13.65 61 13796 553450 63931425
Skin hyperpigmentation 17.31 13.65 13 13844 6538 64478337
Disseminated mycobacterium avium complex infection 16.66 13.65 4 13853 103 64484772
Plasma cell myeloma 16.65 13.65 33 13824 46042 64438833
Arthropathy 16.53 13.65 3 13854 120964 64363911
Tuberculoid leprosy 16.48 13.65 4 13853 108 64484767
Klebsiella infection 16.20 13.65 17 13840 13264 64471611
Application site discolouration 16.11 13.65 6 13851 714 64484161
Linear IgA disease 16.03 13.65 9 13848 2765 64482110
Bronchopulmonary aspergillosis 15.80 13.65 20 13837 19065 64465810
Infection reactivation 15.71 13.65 8 13849 2022 64482853
Clostridium difficile infection 15.68 13.65 28 13829 36135 64448740
Staphylococcal infection 15.62 13.65 34 13823 50644 64434231
Methylobacterium infection 15.44 13.65 3 13854 27 64484848
Thrombocytopenia 15.20 13.65 91 13766 223710 64261165
Arthralgia 15.02 13.65 47 13810 442213 64042662
Vascular cognitive impairment 14.89 13.65 3 13854 33 64484842
Calciphylaxis 14.55 13.65 9 13848 3303 64481572
Application site dryness 14.51 13.65 4 13853 180 64484695
CD4 lymphocytes decreased 14.34 13.65 8 13849 2427 64482448
Photophobia 14.13 13.65 18 13839 17275 64467600
Rheumatoid arthritis 14.02 13.65 9 13848 164285 64320590
Cryopyrin associated periodic syndrome 13.73 13.65 3 13854 50 64484825
Renal failure 13.72 13.65 76 13781 181612 64303263

FDA Adverse Event Reporting System (Pediatric)

None

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 antiinfective agents
CHEBI has role CHEBI:35472 anti-inflammatory drugs
CHEBI has role CHEBI:35816 leprostatic drugs
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 | Suggest Off label Use Form| |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




๐Ÿถ Veterinary Drug Use

None

๐Ÿถ Veterinary products

None

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
Myeloperoxidase Enzyme IC50 6.38 CHEMBL
Glucose-6-phosphate 1-dehydrogenase Enzyme WOMBAT-PK
Cytochrome P450 3A4 Enzyme Ki 4.57 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
6-hydroxymethyl-7,8-dihydropterin pyrophosphokinase Unclassified IC50 4.91 CHEMBL

External reference:

IDSource
4019264 VUID
N0000147467 NUI
D00592 KEGG_DRUG
3108 RXNORM
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
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 26 sections
Dapsone HUMAN PRESCRIPTION DRUG LABEL 1 0378-4830 GEL 75 mg TOPICAL ANDA 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 13668-605 GEL 75 mg TOPICAL ANDA 23 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 16110-367 GEL 50 mg TOPICAL NDA 26 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 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 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 28 sections
Dapsone HUMAN PRESCRIPTION DRUG LABEL 1 51672-1388 GEL 75 mg TOPICAL ANDA 28 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