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| CAS No.: | 599-79-1 |
|---|---|
| Name: | Salicylazosulfapyridine |
| Molecular Structure: | |
|
|
|
| Formula: | C18H14N4O5S |
| Molecular Weight: | 398.399 |
| 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; |
| EINECS: | 209-974-3 |
| Density: | 1.488 g/cm3 |
| Melting Point: | 260-265 °C (dec.)(lit.) |
| Boiling Point: | 689.347 °C at 760 mmHg |
| Flash Point: | 370.704 °C |
| Solubility: | NH4OH 1 M: 50 mg/mL, clear, red |
| Appearance: | brownish-yellow crystals |
| Hazard Symbols: |
 Xn
|
| Risk Codes: | 42/43 |
| Safety: | 22-29/56-45 |
| PSA: | 149.69000 |
| LogP: | 4.85540 |
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| Conditions | Yield |
|---|---|
| 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; |
| Conditions | Yield |
|---|---|
| With sodium hydroxide at 7℃; for 1.5h; pH=10; pH-value; Temperature; | 94.9% |
| Conditions | Yield |
|---|---|
| Stage #1: sodium salicylate; C11H9ClN4O2S In water at -30℃; for 0.0138889h; Stage #2: With hydrogenchloride In water Temperature; | 94.2% |
| Conditions | Yield |
|---|---|
| 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% |
| Conditions | Yield |
|---|---|
| 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 |
| Conditions | Yield |
|---|---|
| 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 |
| Conditions | Yield |
|---|---|
| With sulfuric acid for 8.5h; Reflux; Inert atmosphere; | 87% |
| Conditions | Yield |
|---|---|
| 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% |
| Conditions | Yield |
|---|---|
| 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% |
| Conditions | Yield |
|---|---|
| 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% |
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Chemistry
Molecular Structure:
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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
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.
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. |
Safety Profile
Hazard Codes of Sulfasalazine (CAS NO.599-79-1): 
Xn
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