| Identification | |||||||||||||||||||||||||||||||||||||||||||||||||||
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Name | Dapsone | ||||||||||||||||||||||||||||||||||||||||||||||||||
| Accession Number | DB00250 (APRD00345) | ||||||||||||||||||||||||||||||||||||||||||||||||||
| Type | small molecule | ||||||||||||||||||||||||||||||||||||||||||||||||||
| Groups | approved | ||||||||||||||||||||||||||||||||||||||||||||||||||
| Description | 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) |
||||||||||||||||||||||||||||||||||||||||||||||||||
| Structure |
Download: MOL | SDF | SMILES | InChI Display: 2D Structure | 3D Structure |
||||||||||||||||||||||||||||||||||||||||||||||||||
| Synonyms |
|
||||||||||||||||||||||||||||||||||||||||||||||||||
| Salts | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||
| Brand names |
|
||||||||||||||||||||||||||||||||||||||||||||||||||
| Brand mixtures | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||
| Categories |
|
||||||||||||||||||||||||||||||||||||||||||||||||||
| CAS number | 80-08-0 | ||||||||||||||||||||||||||||||||||||||||||||||||||
| Weight |
Average: 248.301 Monoisotopic: 248.061948328 |
||||||||||||||||||||||||||||||||||||||||||||||||||
| Chemical Formula | C12H12N2O2S | ||||||||||||||||||||||||||||||||||||||||||||||||||
| InChI Key | InChIKey=MQJKPEGWNLWLTK-UHFFFAOYSA-N | ||||||||||||||||||||||||||||||||||||||||||||||||||
| InChI |
InChI=1S/C12H12N2O2S/c13-9-1-5-11(6-2-9)17(15,16)12-7-3-10(14)4-8-12/h1-8H,13-14H2
Plain Text
|
||||||||||||||||||||||||||||||||||||||||||||||||||
| IUPAC Name |
4-[(4-aminobenzene)sulfonyl]aniline
|
||||||||||||||||||||||||||||||||||||||||||||||||||
| SMILES |
NC1=CC=C(C=C1)S(=O)(=O)C1=CC=C(N)C=C1
Plain Text
|
||||||||||||||||||||||||||||||||||||||||||||||||||
| Mass Spec | show (9.27 KB) | ||||||||||||||||||||||||||||||||||||||||||||||||||
| Taxonomy | |||||||||||||||||||||||||||||||||||||||||||||||||||
| Kingdom | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||
| Classes |
|
||||||||||||||||||||||||||||||||||||||||||||||||||
| Substructures |
|
||||||||||||||||||||||||||||||||||||||||||||||||||
| Pharmacology | |||||||||||||||||||||||||||||||||||||||||||||||||||
| Indication | For the treatment and management of leprosy and dermatitis herpetiformis. | ||||||||||||||||||||||||||||||||||||||||||||||||||
| Pharmacodynamics | Dapsone is a sulfone with anti-inflammatory immunosuppressive properties as well as antibacterial and antibiotic properties. Dapsone is the principal drug in a multidrug regimen recommended by the World Health Organization for the treatment of leprosy. As an anti-infective agent, it is also used for treating malaria and, recently, for Pneumocystic carinii pneumonia in AIDS patients. Dapsone is absorbed rapidly and nearly completely from the gastrointestinal tract. Dapsone is distributed throughout total body water and is present in all tissues. However, it tends to be retained in skin and muscle and especially in the liver and kidney: traces of the drug are present in these organs up to 3 weeks after therapy cessation. | ||||||||||||||||||||||||||||||||||||||||||||||||||
| Mechanism of action | Dapsone acts against bacteria and protozoa in the same way as sulphonamides, that is by inhibiting the synthesis of dihydrofolic acid through competition with para-amino-benzoate for the active site of dihydropteroate synthetase. The anti-inflammatory action of the drug is unrelated to its antibacterial action and is still not fully understood. | ||||||||||||||||||||||||||||||||||||||||||||||||||
| Absorption | Bioavailability is 70 to 80% following oral administration. | ||||||||||||||||||||||||||||||||||||||||||||||||||
| Volume of distribution | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||
| Protein binding | 70 to 90% | ||||||||||||||||||||||||||||||||||||||||||||||||||
| Metabolism | Hepatic, mostly CYP2E1-mediated. | ||||||||||||||||||||||||||||||||||||||||||||||||||
| Route of elimination | Renal | ||||||||||||||||||||||||||||||||||||||||||||||||||
| Half life | 28 hours (range 10-50 hours) | ||||||||||||||||||||||||||||||||||||||||||||||||||
| Clearance | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||
| Toxicity | Overdosage might be expected to produce nasal congestion, syncope, or hallucinations. Measures to support blood pressure should be taken if necessary. | ||||||||||||||||||||||||||||||||||||||||||||||||||
| Affected organisms |
|
||||||||||||||||||||||||||||||||||||||||||||||||||
| Pathways | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||
| Pharmacoeconomics | |||||||||||||||||||||||||||||||||||||||||||||||||||
| Manufacturers |
|
||||||||||||||||||||||||||||||||||||||||||||||||||
| Packagers |
|
||||||||||||||||||||||||||||||||||||||||||||||||||
| Dosage forms |
|
||||||||||||||||||||||||||||||||||||||||||||||||||
| Prices |
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational
purposes only.
|
||||||||||||||||||||||||||||||||||||||||||||||||||
| Patents |
|
||||||||||||||||||||||||||||||||||||||||||||||||||
| Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||
| State | solid | ||||||||||||||||||||||||||||||||||||||||||||||||||
| Experimental Properties |
|
||||||||||||||||||||||||||||||||||||||||||||||||||
| Predicted Properties |
|
||||||||||||||||||||||||||||||||||||||||||||||||||
| References | |||||||||||||||||||||||||||||||||||||||||||||||||||
| Synthesis Reference | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||
| General Reference | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||
| External Links |
|
||||||||||||||||||||||||||||||||||||||||||||||||||
| ATC Codes |
|
||||||||||||||||||||||||||||||||||||||||||||||||||
| AHFS Codes |
|
||||||||||||||||||||||||||||||||||||||||||||||||||
| PDB Entries | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||
| FDA label | show (515 KB) | ||||||||||||||||||||||||||||||||||||||||||||||||||
| MSDS | show (53.5 KB) | ||||||||||||||||||||||||||||||||||||||||||||||||||
| Interactions | |||||||||||||||||||||||||||||||||||||||||||||||||||
| Drug Interactions |
|
||||||||||||||||||||||||||||||||||||||||||||||||||
| Food Interactions |
|
||||||||||||||||||||||||||||||||||||||||||||||||||
| Targets |
|---|
|
Pharmacological action: yes
Actions: inhibitor DHPS catalyzes the formation of the immediate precursor of folic acid. It is implicated in resistance to sulfonamide Organism class: bacterialUniProt ID: P0C0X2 ![]() Gene: folP2 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report ![]() References:
Pharmacological action: yes
Actions: inhibitor DHPS catalyzes the formation of the immediate precursor of folic acid. It is implicated in resistance to sulfonamide Organism class: bacterialUniProt ID: P0C0X1 ![]() Gene: folP1 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report ![]() References:
|
| Enzymes |
|---|
|
Actions: substrate
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics UniProt ID: P20815![]() Gene: CYP3A5 ![]() Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report ![]() References:
Actions: substrate
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4- hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. The enzyme also hydroxylates etoposide UniProt ID: P08684![]() Gene: CYP3A4 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report ![]() References:
3. Dimethylaniline monooxygenase [N-oxide-forming] 3 Actions: substrateInvolved in the oxidative metabolism of a variety of xenobiotics such as drugs and pesticides. It N-oxygenates primary aliphatic alkylamines as well as secondary and tertiary amines. Plays an important role in the metabolism of trimethylamine (TMA), via the production of TMA N-oxide (TMAO). Is also able to perform S-oxidation when acting on sulfide compounds UniProt ID: P31513![]() Gene: FMO3 ![]() Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report ![]() References:
4. Prostaglandin G/H synthase 1 Actions: substrateMay play an important role in regulating or promoting cell proliferation in some normal and neoplastically transformed cells UniProt ID: P23219![]() Gene: PTGS1 ![]() Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report ![]() References:
5. Prostaglandin G/H synthase 2 Actions: substrateMay have a role as a major mediator of inflammation and/or a role for prostanoid signaling in activity-dependent plasticity UniProt ID: P35354![]() Gene: PTGS2 ![]() Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report ![]() References:
Actions: substrate
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme responsible for the metabolism the anti- cancer drug paclitaxel (taxol) UniProt ID: P10632![]() Gene: CYP2C8 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report ![]() References:
Actions: substrate
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine UniProt ID: P33261![]() Gene: CYP2C19 ![]() Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report ![]() References:
8. Arylamine N-acetyltransferase 2 Actions: substrateParticipates in the detoxification of a plethora of hydrazine and arylamine drugs. Catalyzes the N- or O-acetylation of various arylamine and heterocyclic amine substrates and is able to bioactivate several known carcinogens UniProt ID: P11245![]() Gene: NAT2 ![]() Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report ![]() References:
Actions: substrate, inducer
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S- warfarin, diclofenac, phenytoin, tolbutamide and losartan UniProt ID: P11712![]() Gene: CYP2C9 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report ![]() References:
Actions: substrate
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics UniProt ID: P24462![]() Gene: CYP3A7 ![]() Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report ![]() References:
Actions: substrate
Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic or carcinogenic forms UniProt ID: P05181![]() Gene: CYP2E1 ![]() Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report ![]() References:
12. Myeloperoxidase Actions: substratePart of the host defense system of polymorphonuclear leukocytes. It is responsible for microbicidal activity against a wide range of organisms. In the stimulated PMN, MPO catalyzes the production of hypohalous acids, primarily hypochlorous acid in physiologic situations, and other toxic intermediates that greatly enhance PMN microbicidal activity UniProt ID: P05164![]() Gene: MPO ![]() Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report ![]() References:
Actions: substrate
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics UniProt ID: P33260![]() Gene: CYP2C18 ![]() Protein Sequence: FASTA SNPs: SNPJam Report ![]() References:
|
| Comments |
|---|