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Sulfanilamide
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| Systematic (IUPAC) name |
| 4-aminobenzenesulfonamide |
| Identifiers |
| CAS number |
63-74-1 |
| ATC code |
J01EB06 D06BA05 QJ01EQ06 |
| PubChem |
CID 5333 |
| DrugBank |
APRD00438 |
| Chemical data |
| Formula |
C6H8N2O2S |
| Mol. mass |
172.20 g/mol |
| Physical data |
| Density |
1.08 g/cm³ |
| Melt. point |
165 °C (329 °F) |
| Therapeutic considerations |
| Pregnancy cat. |
? |
| Legal status |
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Sulfanilamide (also spelled sulphanilamide) is a sulfonamide antibacterial. Chemically, it is a molecule containing the sulfonamide functional group attached to an aniline. As an antibiotic, it functions by competitively inhibiting (ie, by acting as a substrate analogue) enzymatic reactions involving para-aminobenzoic acid (PABA). PABA is needed in enzymatic reactions that produce folic acid which acts as a coenzyme in the synthesis of purine, pyrimidine and other amino acids.
The term "sulfanilamides" is also used to describe a family of molecules containing these functional groups. Examples include:
- Furosemide, a loop diuretic
- Sulfadiazine, an antibiotic
- Sulfamethoxazole, an antibiotic
Gerhard Domagk and Jacques and Therese Trefouel (1935) are generally credited with the discovery of sulfanilamide as a chemotherapeutic agent. Domagk was awarded the Nobel Prize for his work.
See also
- Sulfonamide (medicine)
- Nazi experiments
- Elixir sulfanilamide
External links
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Antibiotics and chemotherapeutics for dermatological use (D06) |
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| Antibiotics |
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Tetracycline and derivatives
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Demeclocycline · Chlortetracycline · Oxytetracycline · Tetracycline
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Others
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Amphenicol: Chloramphenicol
Aminoglycosides: Neomycin · Gentamicin · Amikacin
Quinolone: Nadifloxacin
Streptogramin: Virginiamycin
Rifamycin: Rifaximin
other: Fusidic acid · Bacitracin · Tyrothricin · Mupirocin
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| Chemotherapeutics |
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Sulfonamides
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Silver sulfadiazine · Sulfathiazole · Mafenide · Sulfamethizole · Sulfanilamide · Sulfamerazine
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Antivirals
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Aciclovir · Penciclovir · Idoxuridine · Edoxudine
Imiquimod/Resiquimod · Podophyllotoxin
Docosanol · Tromantadine · Inosine · Lysozyme · Ibacitabine
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Other
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Metronidazole
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noco(i,b,d,q,u,r,p,k,c,v)/cong/tumr(n,e,d), sysi/epon
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Antibacterials: nucleic acid inhibitors (J01E, J01M) |
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Antifolates
(inhibits
purine metabolism,
thereby inhibiting
DNA and RNA synthesis) |
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DR inhibitor
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2,4-Diaminopyrimidine (Trimethoprim#, Brodimoprim, Tetroxoprim, Iclaprim†)
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Sulfonamides
(DS inhibitor)
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Short-
acting
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Sulfaisodimidine · Sulfamethizole · Sulfadimidine · Sulfapyridine · Sulfafurazole · Sulfanilamide (Prontosil) · Sulfathiazole · Sulfathiourea
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Intermediate-
acting
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Sulfamethoxazole · Sulfadiazine# · Sulfamoxole
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Long-
acting
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Sulfadimethoxine · Sulfalene · Sulfametomidine · Sulfametoxydiazine · Sulfamethoxypyridazine · Sulfaperin · Sulfamerazine · Sulfaphenazole · Sulfamazone
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Other/ungrouped
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sulfanilamide (Sulfacetamide, Sulfametrole)
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Combinations
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Sulfamethoxazole and trimethoprim#
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Topoisomerase
inhibitors/
quinolones/
(inhibits
DNA replication) |
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1st generation
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Cinoxacin‡ · Flumequine · Nalidixic acid · Oxolinic acid · Pipemidic acid · Piromidic acid · Rosoxacin
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Fluoroquinolones
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2nd
generation
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Ciprofloxacin# · Enoxacin‡ · Fleroxacin‡ · Lomefloxacin · Nadifloxacin · Ofloxacin · Norfloxacin · Pefloxacin · Rufloxacin
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3rd
generation
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Balofloxacin · Grepafloxacin‡ · Levofloxacin · Pazufloxacin · Sparfloxacin‡ · Temafloxacin‡ · Tosufloxacin
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4th
generation
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Besifloxacin · Clinafloxacin† · Garenoxacin · Gemifloxacin · Moxifloxacin · Gatifloxacin‡ · Sitafloxacin · Trovafloxacin‡/Alatrofloxacin‡ · Prulifloxacin
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Veterinary
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Danofloxacin · Difloxacin · Enrofloxacin · Ibafloxacin · Marbofloxacin · Orbifloxacin · Pradofloxacin · Sarafloxacin
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Related agents (DG)
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Aminocoumarins: Novobiocin
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Anaerobic DNA
inhibitors |
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Nitro- imidazole derivatives
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Metronidazole# · Tinidazole · Ornidazole
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Nitrofuran derivatives
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Furazolidone‡ · Nitrofurantoin# · Nifurtoinol
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| RNA synthesis |
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Rifamycins/
RNA polymerase
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Rifampicin · Rifabutin · Rifapentine · Rifaximin
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#WHO-EM. ‡Withdrawn from market. CLINICAL TRIALS: †Phase III. §Never to phase III
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gr+f/gr+a(t)/gr-p(c)/gr-o
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