dapsone Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |
| Stem definition | Drug id | CAS RN |
|---|---|---|
| antimycobacterials, diaminodiphenylsulfone derivatives | 782 | 80-08-0 |
Description:
| Molecule | Description |
|---|---|
|
Synonyms:
|
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)
Legend: OFP - off patent OFM - off market ONP - on patent |
Drug dosage:
| Dose | Unit | Route |
|---|---|---|
| 50 | mg | O |
ADMET properties:
| Property | Value | Reference |
|---|---|---|
| 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 µM/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:
| Date | Agency | Company | Orphan |
|---|---|---|---|
| July 3, 1979 | FDA | JACOBUS |
FDA Adverse Event Reporting System (Female)
| MedDRA adverse event term | Likelihood ratio | Likelihood ratio threshold | Patients taking drug having adverse event | Patients taking drug not having adverse event | Patients not taking drug having adverse event | Patients 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 term | Likelihood ratio | Likelihood ratio threshold | Patients taking drug having adverse event | Patients taking drug not having adverse event | Patients not taking drug having adverse event | Patients 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:
| Source | Code | Description |
|---|---|---|
| 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)
| Disease | Relation | SNOMED_ID | DOID |
|---|---|---|---|
| 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 level | Dissociation constant | Type (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 strength | Trade name | Applicant | Application number | Approval date | Type | Dose form | Route | Exclusivity date | Description |
|---|---|---|---|---|---|---|---|---|---|
| 7.5% | ACZONE | ALMIRALL | N207154 | Feb. 24, 2016 | RX | GEL | TOPICAL | Sept. 10, 2022 | NEW PATIENT POPULATION |
Bioactivity Summary:
| Target | Class | Pharos | UniProt | Action | Type | Activity value (-log[M]) | Mechanism action | Bioact source | MoA 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:
| ID | Source |
|---|---|
| 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:
| Product | Category | Ingredients | NDC | Form | Quantity | Route | Marketing | Label |
|---|---|---|---|---|---|---|---|---|
| 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 |