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Salicylazosulfapyridine

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Name

Salicylazosulfapyridine

EINECS 209-974-3
CAS No. 599-79-1 Density 1.488 g/cm3
PSA 149.69000 LogP 4.85540
Solubility NH4OH 1 M: 50 mg/mL, clear, red Melting Point 260-265 °C (dec.)(lit.)
Formula C18H14N4O5S Boiling Point 689.347 °C at 760 mmHg
Molecular Weight 398.399 Flash Point 370.704 °C
Transport Information N/A Appearance brownish-yellow crystals
Safety 22-29/56-45 Risk Codes 42/43
Molecular Structure Molecular Structure of 599-79-1 (Salicylazosulfapyridine) Hazard Symbols HarmfulXn
Synonyms

Benzoicacid, 2-hydroxy-5-[[4-[(2-pyridinylamino)sulfonyl]phenyl]azo]- (9CI);Salicylicacid, 5-[[p-(2-pyridylsulfamoyl)phenyl]azo]- (6CI,7CI,8CI);5-[4-(2-Pyridylsulfamyl)phenylazo]-2-hydroxybenzoic acid;5-[p-(2-Pyridylsulfamyl)phenylazo]salicylicacid;Azopyrin;Azopyrine;Azulfidine;Azulfidine EN;Benzosulfa;Colo-Pleon;NSC 203730;NSC 667219;Reupirin;Salazopyridin;Salazopyrin;Salisulf;Sulfasalazin;

Article Data 14

Salicylazosulfapyridine Synthetic route

144-83-2

sulphapyridine

69-72-7

salicylic acid

599-79-1

sulfosalazine

Conditions
ConditionsYield
Stage #1: sulphapyridine With hydrogenchloride; sodium nitrite In water at 2℃; for 0.333333h;
Stage #2: salicylic acid With sodium hydroxide In water at 7℃; for 1.5h; Temperature; Concentration;
95.4%
Stage #1: sulphapyridine With hydrogenchloride; sodium nitrite In water at 2℃; for 0.333333h;
Stage #2: salicylic acid With sodium hydroxide In water at 7℃; for 1.5h; pH=10; Temperature; Time; Concentration;
Stage #1: sulphapyridine With hydrogenchloride; sodium nitrite In water at 0℃; Flow reactor;
Stage #2: salicylic acid With glycine; sodium hydroxide In water; N,N-dimethyl-formamide at 25℃; pH=8.55 - 9; Flow reactor;

4-(Pyridin-2-ylsulfamoyl)-benzenediazonium; chloride

69-72-7

salicylic acid

599-79-1

sulfosalazine

Conditions
ConditionsYield
With sodium hydroxide at 7℃; for 1.5h; pH=10; pH-value; Temperature;94.9%
54-21-7

sodium salicylate

C11H9ClN4O2S

599-79-1

sulfosalazine

Conditions
ConditionsYield
Stage #1: sodium salicylate; C11H9ClN4O2S In water at -30℃; for 0.0138889h;
Stage #2: With hydrogenchloride In water Temperature;
94.2%
89-57-6

5-Aminosalicylic Acid

1202816-93-0

4-nitrososulfopyridine

599-79-1

sulfosalazine

Conditions
ConditionsYield
With hydrogenchloride In methanol; water at 20 - 50℃; pH=3; Concentration; pH-value; Temperature;92.5%
With hydrogenchloride In methanol; water at 30 - 50℃; Temperature;92.5%
504-29-0

2-aminopyridine

599-79-1

sulfosalazine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: potassium carbonate / 1.5 h / 5 °C
2.1: sodium hydroxide / dimethyl sulfoxide; water / 3 h / 90 °C
3.1: sodium nitrite; hydrogenchloride / water / 0.33 h / 2 °C
3.2: 1.5 h / 7 °C / pH 10
View Scheme
121-60-8

p-acetylaminobenzenesulfonyl chloride

599-79-1

sulfosalazine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: potassium carbonate / 1.5 h / 5 °C
2.1: sodium hydroxide / dimethyl sulfoxide; water / 3 h / 90 °C
3.1: sodium nitrite; hydrogenchloride / water / 0.33 h / 2 °C
3.2: 1.5 h / 7 °C / pH 10
View Scheme
64-17-5

ethanol

599-79-1

sulfosalazine

ethyl 2-hydroxy-5-[(E)-2-{4-[(pyridine-2-yl)sulfamoyl]phenyl}diazen-1-yl]benzoate

Conditions
ConditionsYield
With sulfuric acid for 8.5h; Reflux; Inert atmosphere;87%

zinc(II) hydroxide

599-79-1

sulfosalazine

[Zn(sulfasalazine(-1H))(μ-OH)]

Conditions
ConditionsYield
In ethanol; water High Pressure; under hydrothermal conditions; mixt. of ligand, Zn(OH)2, EtOH and H2O placed in Parr stainless steel vessel; sealed; heated to 110°C for 5 d; crystals isolated; elem. anal.;40%

zinc acetate hydrate

599-79-1

sulfosalazine

[Zn(sulfasalazine(-1H))(μ-OH)]

Conditions
ConditionsYield
In ethanol; water High Pressure; under hydrothermal conditions; mixt. of ligand, Zn acetate, EtOH and H2Oplaced in Parr stainless steel vessel; sealed; heated to 110°C f or 5 d; crystals isolated; elem. anal.;40%

C20H33N9O5

599-79-1

sulfosalazine

C38H45N13O9S

Conditions
ConditionsYield
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide at 20℃; for 4h;36%

Salicylazosulfapyridine Chemical Properties

Molecular Structure:

Molecular Formula: C18H14N4O5S
Molecular Weight: 398.3926
IUPAC Name: (3Z)-6-Oxo-3-[[4-(pyridin-2-ylsulfamoyl)phenyl]hydrazinylidene]cyclohexa-1,4-diene-1-carboxylic acid
Synonyms of Sulfasalazine (CAS NO.599-79-1): 2-Hydroxy-5-((4-((2-pyridinylamino)sulfonyl)phenyl)azo)benzoic acid ; 4-(Pyridyl-2-amidosulfonyl)-3'-carboxy-4'-hydroxyazobenzene ; 5-((p-(2-Pyridylsulfamoyl)phenyl)azo)salicylic acid ; 5-(4-(2-Pyridylsulfamoyl)phenylazo)-2-hydroxybenzoic acid ; 5-(p-(2-Pyridylsulfamyl)phenylazo)salicylic acid ; 5-22-08-00433 (Beilstein Handbook Reference) ; Accucol ; Asulfidine ; Azopyrin ; Azopyrine ; Azosulfidin ; Azulfidine ; Azulfidine EN-Tabs ; BRN 0356241 ; Benzoic acid, 2-hydroxy-5-((4-((2-pyridinylamino)sulfonyl)phenyl)azo)- ; Benzosulfa ; CCRIS 4713 ; Colo-Pleon ; EINECS 209-974-3 ; HSDB 3395 ; NSC 203730 ; NSC 667219 ; Reupirin ; Rorasul ; S.A.S. 500 ; S.A.S.-500 ; SASP ; SI-88 ; Salazo-sulfapyridinum ; Salazosulfapyridin ; Salazosulfapyridine ; Salazosulfapyridinum ; UNII-3XC8GUZ6CB ; W-T Sasp Oral
CAS NO: 599-79-1
Classification Code: Analgesics ; Analgesics, Non-Narcotic ; Anti-Inflammatory Agents ; Anti-infective agents ; Anti-inflammatory agents, non-steroidal ; Antibacterial ; Antirheumatic agents ; Drug / Therapeutic Agent ; Gastrointestinal agents ; Human Data ; Mutation data ; Peripheral Nervous System Agents ; Reproductive Effect ; Sensory System Agents ; Tumor data
Melting point: 260-265 °C 
Index of Refraction: 1.691
Molar Refractivity: 102.381 cm3
Molar Volume: 267.677 cm3
Surface Tension: 65.715 dyne/cm
Density: 1.488 g/cm3
Flash Point: 370.704 °C
Enthalpy of Vaporization: 106.117 kJ/mol
Boiling Point: 689.347 °C at 760 mmHg

Salicylazosulfapyridine Uses

 Sulfasalazine (CAS NO.599-79-1) is used in the treatment of granulomatous colitis.It's intestinal sulfa drugs, and  have a special affinity with connective tissue. It is currently a better ulcer drug for the treatment of chronic conjunctivitis.

Salicylazosulfapyridine Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
child TDLo oral 3800mg/kg/19D (3800mg/kg) LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), DIFFUSE" American Journal of Digestive Diseases. Vol. 23, Pg. 956, 1978.
human TDLo oral 429mg/kg/10D- (429mg/kg) BLOOD: OTHER HEMOLYSIS WITH OR WITHOUT ANEMIA New England Journal of Medicine. Vol. 289, Pg. 491, 1973.
man LDLo oral 3200mg/kg/31D (3200mg/kg) BLOOD: AGRANULOCYTOSIS

SKIN AND APPENDAGES (SKIN): "DERMATITIS, ALLERGIC: AFTER SYSTEMIC EXPOSURE"

BLOOD: OTHER CHANGES
Journal of the Royal Society of Medicine. Vol. 73, Pg. 587, 1980.
man TDLo oral 7143ug/kg (7.143mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

GASTROINTESTINAL: NAUSEA OR VOMITING
New England Journal of Medicine. Vol. 306, Pg. 409, 1982.
man TDLo oral 143mg/kg/10D- (143mg/kg) BLOOD: THROMBOCYTOPENIA Annals of Internal Medicine. Vol. 102, Pg. 277, 1985.
man TDLo oral 357mg/kg (357mg/kg) BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"

BEHAVIORAL: HEADACHE
Journal of Toxicology, Clinical Toxicology. Vol. 29, Pg. 543, 1991.
man TDLo oral 1286mg/kg/30D (1286mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

BLOOD: EOSINOPHILIA

BLOOD: CHANGES IN CELL COUNT (UNSPECIFIED)
Internal Medicine. Vol. 31, Pg. 108, 1992.
man TDLo oral 122gm/kg/8Y-I (122000mg/kg) PERIPHERAL NERVE AND SENSATION: PARESTHESIS

VASCULAR: OTHER CHANGES
Postgraduate Medical Journal. Vol. 56, Pg. 106, 1980.
man TDLo rectal 7143ug/kg (7.143mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

GASTROINTESTINAL: NAUSEA OR VOMITING
New England Journal of Medicine. Vol. 306, Pg. 409, 1982.
man TDLo unreported 1300mg/kg/4W- (1300mg/kg) BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"

GASTROINTESTINAL: NAUSEA OR VOMITING

BEHAVIORAL: ATAXIA
Practitioner. Vol. 204, Pg. 850, 1970.
mouse LD50 intravenous 1096mg/kg (1096mg/kg)   Drugs in Japan Vol. -, Pg. 420, 1990.
mouse LD50 oral 12500mg/kg (12500mg/kg)   Drugs in Japan Vol. -, Pg. 420, 1990.
mouse LD50 subcutaneous 3gm/kg (3000mg/kg)   Drugs in Japan Vol. -, Pg. 420, 1990.
rabbit LD50 oral > 7500mg/kg (7500mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 26, Pg. 953, 1995.
rat LD50 intravenous 1520mg/kg (1520mg/kg)   Drugs in Japan Vol. -, Pg. 420, 1990.
rat LD50 oral 15600mg/kg (15600mg/kg)   Drugs in Japan Vol. -, Pg. 420, 1990.
rat LD50 subcutaneous 3870mg/kg (3870mg/kg)   Drugs in Japan Vol. -, Pg. 420, 1990.
women LDLo unreported 840mg/kg/3W-I (840mg/kg) LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), DIFFUSE"

SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"

IMMUNOLOGICAL INCLUDING ALLERGIC: INCREASED IMMUNE RESPONSE
Therapie. Vol. 37, Pg. 315, 1982.
women TDLo oral 140mg/kg/2W-I (140mg/kg) BEHAVIORAL: HEADACHE

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
Lancet. Vol. 1, Pg. 917, 1984.
women TDLo oral 570mg/kg/11D- (570mg/kg) BLOOD: LEUKOPENIA

BLOOD: THROMBOCYTOPENIA

BLOOD: OTHER CHANGES
Clinical and Experimental Dermatology. Vol. 19, Pg. 419, 1994.
women TDLo oral 700mg/kg/4W-I (700mg/kg) BEHAVIORAL: EXCITEMENT

LIVER: LIVER FUNCTION TESTS IMPAIRED

BLOOD: CHANGES IN LEUCOCYTE (WBC) COUNT
Clinical and Experimental Rheumatology. Vol. 10, Pg. 427, 1992.
women TDLo unreported 2700mg/kg/13W (2700mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" British Medical Journal. Vol. 286, Pg. 1547, 1983.

Salicylazosulfapyridine Safety Profile

Hazard Codes of Sulfasalazine (CAS NO.599-79-1): HarmfulXn
Risk Statements: 42/43 
R42/43: May cause sensitization by inhalation and skin contact.
Safety Statements: 22-29/56-45 
S22: Do not breathe dust. 
S29: Do not empty into drains. 
S56: Dispose of this material and its container at hazardous or special waste collection point. 
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
WGK Germany: 2
F: 8

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