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Substance Name: Dapsone [USAN:USP:INN:BAN]
RN: 80-08-0
UNII: 8W5C518302
InChIKey: MQJKPEGWNLWLTK-UHFFFAOYSA-N

Note

  • 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 Formula

  • C12-H12-N2-O2-S

Molecular Weight

  • 248.305
 

Classification Codes

Classification Codes

  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Antibacterial (Leprostatic)
  • Antibacterial (Tuberculostatic)
  • Antimalarials
  • Antiparasitic Agents
  • Antiprotozoal Agents
  • Dermatitis Herpetiformis Suppressant
  • Drug / Therapeutic Agent
  • Enzyme Inhibitors
  • Folic Acid Antagonists
  • Human Data
  • Leprostatic Agents
  • Mutation Data
  • Reproductive Effect
  • Suppressant (Dermatitis Herpetiformis)
  • Tumor Data

Superlist Classification Code

  • Overall Carcinogenic Evaluation: Group 3

Names and Synonyms

Name of Substance

  • Dapsone
  • Dapsone [USAN:USP:INN:BAN]

MeSH Heading

  • Dapsone

Synonyms

  • 1,1'-Sulfonylbis(4-aminobenzene)
  • 1,1'-Sulphonylbis(4-aminobenzene)
  • 1358F
  • 4,4'-Dapsone
  • 4,4'-Diaminodiphenyl sulfone
  • 4,4'-Diaminodiphenyl suphone
  • 4,4'-Sulfonylbisaniline
  • 4,4'-Sulfonylbisbenzamine
  • 4,4'-Sulfonylbisbenzenamine
  • 4,4'-Sulfonyldianiline
  • 4,4'-Sulphonylbisbenzamine
  • 4,4'-Sulphonylbisbenzenamine
  • 4,4'-Sulphonyldianiline
  • 4,4-Diaminodifenylsulfon
  • 4,4-Diaminodifenylsulfon [Czech]
  • 4-13-00-01306 (Beilstein Handbook Reference)
  • 4-Aminophenyl sulfone
  • Aczone
  • AI3-08087
  • Aniline, 4,4'-sulfonyldi-
  • Araldite HT 976
  • Avlosulfon
  • Avlosulfone
  • Avlosulphone
  • Benzenamine, 4,4'-sulfonylbis-
  • Bis(4-aminophenyl) sulfone
  • Bis(4-aminophenyl)sulphone
  • Bis(p-aminophenyl) sulfone
  • Bis(p-aminophenyl)sulphone
  • BRN 0788055
  • CCRIS 192
  • Croysulfone
  • Croysulphone
  • DADPS
  • Dapson
  • Dapsona
  • Dapsona [INN-Spanish]
  • Dapsone
  • Dapsonum
  • Dapsonum [INN-Latin]
  • DDS
  • DDS (pharmaceutical)
  • Di(4-aminophenyl) sulfone
  • Di(4-aminophenyl)sulfone
  • Di(4-aminophenyl)sulphone
  • Di(p-aminophenyl) sulfone
  • Di(p-aminophenyl)sulphone
  • Diamino-4,4'-diphenyl sulfone
  • Diamino-4,4'-diphenyl sulphone
  • Diaminodifenilsulfona
  • Diaminodifenilsulfona [Spanish]
  • Diaminodiphenyl sulfone
  • Diaphenylsulfon
  • Diaphenylsulfone
  • Diaphenylsulphon
  • Diaphenylsulphone
  • Diphenasone
  • Diphone
  • Disulone
  • DSS
  • DSS (VAN)
  • Dubronax
  • Dumitone
  • EC 201-248-4
  • EINECS 201-248-4
  • Eporal
  • F 1358
  • Hardener HT 976
  • HSDB 5073
  • HT 976
  • HY 976
  • Metabolite C
  • N,N'-Diphenyl sulfondiamide
  • NCI-C01718
  • Novophone
  • NSC 6091
  • NSC 6091D
  • NSC-6091
  • p,p'-Diaminodiphenyl sulfone
  • p,p'-Sulfonyldianiline
  • p,p-Diaminodiphenyl sulphone
  • p,p-Sulfonylbisbenzamine
  • p,p-Sulfonylbisbenzenamine
  • p,p-Sulphonylbisbenzamine
  • p,p-Sulphonylbisbenzenamine
  • p,p-Sulphonyldianiline
  • p-Aminophenyl sulfone
  • Sulfadione
  • Sulfona
  • Sulfona-Mae
  • Sulfone UCB
  • Sulfone, diphenyl, 4,4'-diamino-
  • Sulphadione
  • Sulphonyldianiline
  • Sumicure S
  • Tarimyl
  • Udolac
  • UNII-8W5C518302
  • WR 448

Systematic Names

  • Aniline, 4,4'-sulfonyldi-
  • Benzenamine, 4,4'-sulfonylbis-
  • Dapsone

Superlist Names

  • 4,4'-Sulfonyldianiline
  • Dapsone

Registry Numbers

CAS Registry Number

  • 80-08-0

FDA UNII

  • 8W5C518302

Other Registry Number

  • 1246638-15-2

System Generated Number

  • 0000080080

Structure Descriptors

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

InChIKey

MQJKPEGWNLWLTK-UHFFFAOYSA-N

Smiles

Nc1ccc(cc1)S(=O)(=O)c2ccc(N)cc2

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LDLo oral 357mg/kg (357mg/kg)   Archives of Neurology and Psychiatry. Vol. 54, Pg. 319, 1945.
child TDLo oral 5mg/kg (5mg/kg) LUNGS, THORAX, OR RESPIRATION: CYANOSIS Journal of Toxicology, Clinical Toxicology. Vol. 19, Pg. 1061, 1982/1983.
child TDLo oral 37500ug/kg (37.5mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING

BLOOD: METHEMOGLOBINEMIA-CARBOXYHEMOGLOBIN

LUNGS, THORAX, OR RESPIRATION: CYANOSIS		 Pediatric Emergency Care. Vol. 13, Pg. 127, 1997.
domestic animals - goat/sheep LDLo unreported 200mg/kg (200mg/kg)   British Journal of Pharmacology and Chemotherapy. Vol. 5, Pg. 565, 1950.
domestic animals - goat/sheep LDLo unreported 200mg/kg (200mg/kg) BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)

PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE		 British Journal of Pharmacology and Chemotherapy. Vol. 5, Pg. 565, 1950.
guinea pig LD50 oral 300mg/kg (300mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 22, Pg. 967, 1991.
human TDLo oral 18gm/kg/15Y (18000mg/kg) KIDNEY, URETER, AND BLADDER: OTHER CHANGES

MUSCULOSKELETAL: JOINTS		 British Medical Journal. Vol. 1, Pg. 78, 1978.
mammal (species unspecified) LD50 unreported 1400mg/kg (1400mg/kg)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 43(9), Pg. 23, 1978.
man TDLo oral 36mg/kg (36mg/kg) BLOOD: METHEMOGLOBINEMIA-CARBOXYHEMOGLOBIN Human Toxicology. Vol. 2, Pg. 507, 1983.
mouse LD50 intraperitoneal 313mg/kg (313mg/kg)   Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 48, Pg. 336, 1952.
mouse LD50 intravenous 225mg/kg (225mg/kg)   Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 48, Pg. 336, 1952.
mouse LD50 oral 250mg/kg (250mg/kg)   American Review of Tuberculosis. Vol. 60, Pg. 62, 1949.
mouse LD50 subcutaneous 250mg/kg (250mg/kg)   American Review of Tuberculosis. Vol. 60, Pg. 62, 1949.
rabbit LD50 skin > 4gm/kg (4000mg/kg)   Toxicology and Applied Pharmacology. Vol. 28, Pg. 313, 1974.
rat LD50 intraperitoneal 196mg/kg (196mg/kg) PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE)

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD		 Archives Internationales de Pharmacodynamie et de Therapie. Vol. 183, Pg. 36, 1970.
rat LD50 oral 1gm/kg (1000mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 5, Pg. 213, 1955.
women TDLo oral 18mg/kg (18mg/kg) LUNGS, THORAX, OR RESPIRATION: CYANOSIS

BLOOD: METHEMOGLOBINEMIA-CARBOXYHEMOGLOBIN		 Acta Medica Scandinavica. Vol. 214, Pg. 215, 1983.
women TDLo oral 28mg/kg (28mg/kg) BLOOD: AGRANULOCYTOSIS British Medical Journal. Vol. 286, Pg. 1244, 1983.
women TDLo oral 112mg/kg/4W-I (112mg/kg) CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP

BEHAVIORAL: MUSCLE WEAKNESS

BLOOD: OXIDANT RELATED (GPD DEFICIENT) ANEMIA		 Clinical and Experimental Dermatology. Vol. 20, Pg. 155, 1995.
women TDLo oral 300mg/kg/21W- (300mg/kg) BLOOD: EOSINOPHILIA Lancet. Vol. 343, Pg. 860, 1994.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 175.5 deg C   EXP
pKa Dissociation Constant 2.41 (none)   EXP
log P (octanol-water) 0.97 (none)   EXP
Water Solubility 380 mg/L 37 EXP
Vapor Pressure 2.68E-08 mm Hg 25 EST
Henry's Law Constant 3.11E-14 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 4.60E-11 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.