Sulfapyridine

Names

[ CAS No. ]:
144-83-2

[ Name ]:
Sulfapyridine

[Synonym ]:
N'-2-Pyridylsulfanilide
Sulfapyridine (USP)
2-(4-Aminobenzenesulfonamido)pyridine
4-Amino-N-(2-pyridinyl)benzenesulfonamide
EINECS 205-642-7
MFCD00038036
Sulfapyridine
Benzenesulfonamide, 4-amino-N-2-pyridinyl-
4-Amino-N-(pyridin-2-yl)benzenesulfonamide
M & B 693
T6NJ BMSWR DZ
4-amino-N-pyridin-2-ylbenzenesulfonamide
2-Sulfanilamidopyridine
4-Amino-N-[2-pyridyl]benzene sulfonamide (N1-(Pyridin-2-yl)sulfanilamide

Biological Activity

[Description]:

Sulfapyridine(Dagenan) is a sulfonamide antibacterial.Target: AntibacterialSulfapyridine(Dagenan) is a sulfonamide antibacterial. Sulfapyridine is not prescribed for the treatment in humans any more. However, it may be used to treat Linear IgA Disease. It is a good antibacterial drug, but its water solubility is very dependent on PH. Thus, there is a risk of crystallization within the bladder or urethra, which could lead to pain or blockage. The drug sulfasalazine is structurally one molecule of mesalamine linked to one molecule of Sulfapyridine with an azo bond [1].

[Related Catalog]:

Signaling Pathways >> Anti-infection >> Bacterial

Natural Products >> Alkaloid

Research Areas >> Infection

[References]

[1]. Hanauer, S.B., Review article: high-dose aminosalicylates to induce and maintain remissions in ulcerative colitis. Aliment Pharmacol Ther, 2006. 24 Suppl 3: p. 37-40.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Boiling Point ]:
473.5±51.0 °C at 760 mmHg

[ Melting Point ]:
191-193°C

[ Molecular Formula ]:
C₁₁H₁₁N₃O₂S

[ Molecular Weight ]:
249.289

[ Flash Point ]:
240.2±30.4 °C

[ Exact Mass ]:
249.057190

[ PSA ]:
93.46000

[ LogP ]:
0.03

[ Vapour Pressure ]:
0.0±1.2 mmHg at 25°C

[ Index of Refraction ]:
1.674

[ Storage condition ]:
2-8°C

[ Stability ]:
Stable. Combustible. Protect from light. Incompatible with strong oxidizing agents.

[ Water Solubility ]:
<0.1 g/100 mL at 22 ºC

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: DA9625000

CHEMICAL NAME :: Benzenesulfonamide, 4-amino-N-(2-pyridinyl)-

CAS REGISTRY NUMBER :: 144-83-2

LAST UPDATED :: 199701

DATA ITEMS CITED :: 19

MOLECULAR FORMULA :: C11-H11-N3-O2-S

MOLECULAR WEIGHT :: 249.31

WISWESSER LINE NOTATION :: T6NJ BMSWR DZ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 15800 mg/kg

TOXIC EFFECTS :: Peripheral Nerve and Sensation - spastic paralysis with or without sensory change Behavioral - muscle weakness Lungs, Thorax, or Respiration - dyspnea

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 800 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 16600 mg/kg

TOXIC EFFECTS :: Behavioral - tremor Lungs, Thorax, or Respiration - dyspnea Nutritional and Gross Metabolic - body temperature decrease

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1150 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Lungs, Thorax, or Respiration - dyspnea

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 500 mg/kg

TOXIC EFFECTS :: Behavioral - tremor Behavioral - convulsions or effect on seizure threshold Gastrointestinal - nausea or vomiting

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 20 gm/kg

TOXIC EFFECTS :: Kidney, Ureter, Bladder - other changes

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Primate - monkey

DOSE/DURATION :: 8400 mg/kg/21D-I

TOXIC EFFECTS :: Kidney, Ureter, Bladder - hematuria Kidney, Ureter, Bladder - structural or functional changes in ureter Nutritional and Gross Metabolic - weight loss or decreased weight gain

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 135 mg/kg/9W-I

TOXIC EFFECTS :: Tumorigenic - equivocal tumorigenic agent by RTECS criteria Lungs, Thorax, or Respiration - tumors Tumorigenic - tumors at site of application

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 13482 mg/kg

SEX/DURATION :: male 6 week(s) pre-mating

TOXIC EFFECTS :: Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count) Reproductive - Fertility - male fertility index (e.g. # males impregnating females per # males exposed to fertile nonpregnant females)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 10080 mg/kg

SEX/DURATION :: male 28 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 12600 mg/kg

SEX/DURATION :: male 35 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Paternal Effects - testes, epididymis, sperm duct

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 4200 mg/kg

SEX/DURATION :: male 35 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 46200 mg/kg

SEX/DURATION :: male 60 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Fertility - litter size (e.g. # fetuses per litter; measured before birth)

TYPE OF TEST :: Micronucleus test

TYPE OF TEST :: Micronucleus test

MUTATION DATA

TYPE OF TEST :: Sister chromatid exchange

TEST SYSTEM :: Rodent - hamster Ovary

DOSE/DURATION :: 1667 mg/L

REFERENCE :: MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 283,59,1992 *** REVIEWS *** TOXICOLOGY REVIEW JMSHAO Journal of the Mount Sinai Hospital (New York). (New York, NY) V.1-36, 1934-69. For publisher information, see MSJMAZ. Volume(issue)/page/year: 10,343,1943

Safety Information

[ Hazard Codes ]:
Xi

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
S22-S24/25

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
2

[ RTECS ]:
DA9625000

[ HS Code ]:
2935009090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2935009090

[ Summary ]:
2935009090 other sulphonamides VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:6.5% General tariff:35.0%

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