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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
- All
- Classifications
- Links to Resources
- Names & Synonyms
- Registry Numbers
- Structure Descriptors
- Toxicity
- Physical Properties
Classification Codes
Classification Codes
- Anti-Bacterial Agents
- Anti-Infective Agents
- Antibacterial (Leprostatic)
- Antibacterial (Tuberculostatic)
- Antimalarials
- Antiparasitic Agents
- Antiprotozoal Agents
- Antiviral (COVID-19)
- 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
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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,13-14H2InChIKey
MQJKPEGWNLWLTK-UHFFFAOYSA-NSmiles
Nc1ccc(cc1)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.