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dapsone 🐶 Veterinary Use | 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
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

Molecule

Description

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:

Dose	Unit	Route
50	mg	O

ADMET properties:

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Property	Value	Reference
BA (Bioavailability)	93 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
t_half (Half-life)	22 hours	Lombardo F, Berellini G, Obach RS
MRTD (Maximum Recommended Therapeutic Daily Dose)	20.14 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BDDCS (Biopharmaceutical Drug Disposition Classification System)	2	Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine)	15 %	Benet LZ, Broccatelli F, Oprea TI
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
S (Water solubility)	0.20 mg/mL	Benet LZ, Broccatelli F, Oprea TI

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Approvals:

Date	Agency	Company	Orphan
July 3, 1979	FDA	JACOBUS

FDA Adverse Event Reporting System (Female)

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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	770.37	15.36	153	9621	2250	63476998
Drug reaction with eosinophilia and systemic symptoms	281.38	15.36	126	9648	33710	63445538
Haemolytic anaemia	149.87	15.36	57	9717	10068	63469180
Off label use	104.22	15.36	281	9493	674181	62805067
Drug ineffective	70.24	15.36	331	9443	1044434	62434814
Blood methaemoglobin present	57.79	15.36	10	9764	64	63479184
Type 2 lepra reaction	56.60	15.36	9	9765	31	63479217
Treatment failure	54.01	15.36	104	9670	198939	63280309
Haemolysis	52.36	15.36	24	9750	6744	63472504
Sepsis	49.08	15.36	86	9688	153037	63326211

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FDA Adverse Event Reporting System (Male)

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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	349.84	16.15	96	9052	3485	34944298
Drug reaction with eosinophilia and systemic symptoms	168.92	16.15	106	9042	32906	34914877
Type 2 lepra reaction	148.71	16.15	28	9120	167	34947616
Haemolytic anaemia	106.84	16.15	53	9095	10426	34937357
Vanishing bile duct syndrome	79.83	16.15	23	9125	995	34946788
Type 1 lepra reaction	72.55	16.15	12	9136	28	34947755
Nocardiosis	58.91	16.15	26	9122	3925	34943858
Brain abscess	51.27	16.15	22	9126	3103	34944680
Mycobacterium avium complex infection	48.99	16.15	20	9128	2491	34945292
Pleocytosis	45.65	16.15	13	9135	539	34947244

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FDA Adverse Event Reporting System (Geriatric)

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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	964.48	14.23	224	15921	5333	79722910
Drug reaction with eosinophilia and systemic symptoms	450.95	14.23	232	15913	64012	79664231
Haemolytic anaemia	246.13	14.23	103	16042	17717	79710526
Type 2 lepra reaction	190.55	14.23	34	16111	194	79728049
Blood methaemoglobin present	87.48	14.23	16	16129	107	79728136
Type 1 lepra reaction	84.95	14.23	14	16131	45	79728198
Drug ineffective	79.31	14.23	428	15717	1080485	78647758
Haemolysis	77.59	14.23	42	16103	12770	79715473
Vanishing bile duct syndrome	77.17	14.23	24	16121	1754	79726489
Off label use	76.04	14.23	373	15772	906842	78821401

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FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

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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
ATC	J04BA50	ANTIINFECTIVES FOR SYSTEMIC USE ANTIMYCOBACTERIALS DRUGS FOR TREATMENT OF LEPRA Drugs for treatment of lepra
ATC	J04BA51	ANTIINFECTIVES FOR SYSTEMIC USE ANTIMYCOBACTERIALS DRUGS FOR TREATMENT OF LEPRA Drugs for treatment of lepra
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
FDA CS	M0020791	Sulfones
FDA EPC	N0000175881	Sulfone

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Drug Use | Suggest Off label Use Form| |View source of the data|

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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

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🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

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)

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Formulation strength	Trade name	Applicant	Application number	Approval date	Type	Dose form	Route	Patent number	Patent expiration date	Patent use
7.5%	ACZONE	ALMIRALL	N207154	Feb. 24, 2016	RX	GEL	TOPICAL	9517219	Nov. 18, 2033	TOPICAL TREATMENT OF ACNE VULGARIS

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Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

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Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Bioact source	MoA source
5-hydroxytryptamine receptor 6	GPCR	P50406	5HT6R_HUMAN		Ki	6.74	CHEMBL
Myeloperoxidase	Enzyme	P05164	PERM_HUMAN		IC50	6.38	CHEMBL
Glucose-6-phosphate 1-dehydrogenase	Enzyme	P11413	G6PD_HUMAN				WOMBAT-PK
Cytochrome P450 3A4	Enzyme	P08684	CP3A4_HUMAN		Ki	4.57	WOMBAT-PK
Dihydropteroate synthase 1	Enzyme		DHPS1_MYCLE	INHIBITOR	IC50	5.90	WOMBAT-PK	CHEMBL
Dihydrofolate reductase	Enzyme		DYR_PNECA		IC50	5.82	CHEMBL
Dihydropteroate synthetase, putative	Unclassified		Q4Z710_PLABA		IC50	4.91	CHEMBL
6-hydroxymethyl-7,8-dihydropterin pyrophosphokinase	Unclassified		A0A113T0T6_PLABE		IC50	4.91	CHEMBL

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External reference:

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ID	Source
003003	NDDF
10934	IUPHAR_LIGAND_ID
1676	INN_ID
17308007	SNOMEDCT_US
2955	PUBCHEM_CID
3108	RXNORM
387096002	SNOMEDCT_US
4019264	VUID
4019264	VANDF
4536	MMSL

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Pharmaceutical products:

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Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
ACZONE	HUMAN PRESCRIPTION DRUG LABEL	1	0023-3670	GEL	50 mg	TOPICAL	NDA	26 sections
ACZONE	HUMAN PRESCRIPTION DRUG LABEL	1	0023-3670	GEL	50 mg	TOPICAL	NDA	26 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
Aczone	HUMAN PRESCRIPTION DRUG LABEL	1	16110-526	GEL	75 mg	TOPICAL	NDA	26 sections
ACZONE7.5	HUMAN PRESCRIPTION DRUG LABEL	1	0023-5206	GEL	75 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	0713-0886	GEL	50 mg	TOPICAL	ANDA	26 sections
DAPSONE	HUMAN PRESCRIPTION DRUG LABEL	1	0904-7018	TABLET	100 mg	ORAL	ANDA	11 sections

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