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CAS No.: | 1847-24-1 |
---|---|
Name: | Flucloxacillin sodium |
Article Data: | 5 |
Molecular Structure: | |
Formula: | C19H16ClFN3NaO5S |
Molecular Weight: | 475.86 |
Synonyms: | 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid,6-[3-(2-chloro-6-fluorophenyl)-5-methyl-4-isoxazolecarboxamido]-3,3-dimethyl-7-oxo-,sodium salt (7CI);4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid,6-[[[3-(2-chloro-6-fluorophenyl)-5-methyl-4-isoxazolyl]carbonyl]amino]-3,3-dimethyl-7-oxo-,monosodium salt, (2S,5R,6R)- (9CI);4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid,6-[[[3-(2-chloro-6-fluorophenyl)-5-methyl-4-isoxazolyl]carbonyl]amino]-3,3-dimethyl-7-oxo-,monosodium salt, [2S-(2a,5a,6b)]-;Floxacillin sodium;Floxapen;Floxapen sodium;Flucloxacillin sodium salt;Monosodium flucloxacillin;NSC 277175;Sodium[3-(2-chloro-6-fluorophenyl)-5-methyl-4-isoxazolyl]penicillin;Sodium flucloxacillin;Staphylex;Sodium 6-({[3-(2-chloro-6-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]carbonyl}amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate; |
EINECS: | 217-428-0 |
Melting Point: | 176-178 °C |
Boiling Point: | 677.3 °C at 760 mmHg |
Flash Point: | 363.4 °C |
Solubility: | Soluble in water |
Appearance: | White solid |
PSA: | 140.87000 |
LogP: | 1.68190 |
floxacillin
Flucloxacillin sodium
Conditions | Yield |
---|---|
With sodium isooctanoate In ethyl acetate Solvent; | 90.6% |
Conditions | Yield |
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Multi-step reaction with 3 steps 1.1: hydroxylamine sulfate / methanol / 1 h / 20 - 40 °C 1.2: 24 h / 0 - 20 °C / pH ~ 9.5 / Inert atmosphere 1.3: pH ~ 7 - 7.5 2.1: phosphorus pentachloride / toluene 3.1: ammonium hydroxide / ethyl acetate / pH 2 - 9 View Scheme |
Conditions | Yield |
---|---|
With ammonium hydroxide In ethyl acetate pH=2 - 9; |
3-(2-chloro-6-flourophenyl)-5-methyl-isoxazole-4-carboxylic acid
Flucloxacillin sodium
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: triethylamine / dichloromethane / 0.67 h / -5 - 0 °C 2.1: 30 - 35 °C 2.2: 1 h / -5 - 0 °C 3.1: sodium isooctanoate / acetone; water; ethyl acetate / 3 h / 20 - 25 °C View Scheme |
Flucloxacillin sodium
Conditions | Yield |
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With sodium isooctanoate In water; ethyl acetate; acetone at 20 - 25℃; for 3h; Time; | 20.3 g |
Conditions | Yield |
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Stage #1: 6-Aminopenicillanic Acid; C18H10ClFN2O2S2 With triethylamine In dichloromethane; water at 8 - 15℃; pH=6.5 - 8.5; Large scale; Stage #2: With sodium acetate In acetic acid butyl ester at 20 - 35℃; for 0.5h; Large scale; |
Flucloxacillin sodium
A
5-Hydroxymethylflucloxacillin
Conditions | Yield |
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With metabolism in male albino rat |
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The Flucloxacillin sodium, with the CAS registry number 1847-24-1, is also known as 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid,6-[[[3-(2-chloro-6-fluorophenyl)-5-methyl-4-isoxazolyl]carbonyl]amino]-3,3-dimethyl-7-oxo-,monosodium salt, [2S-(2a,5a,6b)]-. It belongs to the product categories of API; APIs; Intermediates & Fine Chemicals; Pharmaceuticals; Peptide Synthesis/Antibiotics. Its EINECS number is 217-428-0. This chemical's molecular formula is C19H16ClFN3NaO5S and molecular weight is 475.85. What's more, its systematic name is Sodium 6-({[3-(2-chloro-6-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]carbonyl}amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate. Its classification codes are: (1)Drug / Therapeutic Agent; (2)Human Data; (3)Reproductive Effect. This chemical can be used as flucloxacillin, a new semisynthetic penicillin.
Physical properties of Flucloxacillin sodium are: (1)ACD/LogP: 2.597; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.45; (4)ACD/LogD (pH 7.4): -1.13; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 1.00; (8)ACD/KOC (pH 7.4): 1.00; (9)#H bond acceptors: 8; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 4; (12)Polar Surface Area: 129.25 Å2; (13)Flash Point: 363.4 °C; (14)Enthalpy of Vaporization: 104.44 kJ/mol; (15)Boiling Point: 677.3 °C at 760 mmHg; (16)Vapour Pressure: 2.86E-19 mmHg at 25°C.
You can still convert the following datas into molecular structure:
(1)SMILES: [Na+].O=C([O-])C3N4C(=O)C(NC(=O)c2c(onc2c1c(F)cccc1Cl)C)C4SC3(C)C
(2)Std. InChI: InChI=1S/C19H17ClFN3O5S.Na/c1-7-10(12(23-29-7)11-8(20)5-4-6-9(11)21)15(25)22-13-16(26)24-14(18(27)28)19(2,3)30-17(13)24;/h4-6,13-14,17H,1-3H3,(H,22,25)(H,27,28);/q;+1/p-1
(3)Std. InChIKey: OTEANHMVDHZOPB-UHFFFAOYSA-M
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
dog | LD50 | intravenous | 670mg/kg (670mg/kg) | GASTROINTESTINAL: NAUSEA OR VOMITING LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | Chemotherapy Vol. 17, Pg. 1523, 1969. |
dog | LD50 | oral | > 10gm/kg (10000mg/kg) | GASTROINTESTINAL: NAUSEA OR VOMITING GASTROINTESTINAL: ULCERATION OR BLEEDING FROM STOMACH | Chemotherapy Vol. 17, Pg. 1523, 1969. |
mouse | LD50 | intraperitoneal | 1350mg/kg (1350mg/kg) | Drugs in Japan Vol. 6, Pg. 697, 1982. | |
mouse | LD50 | intravenous | 1360mg/kg (1360mg/kg) | Drugs in Japan Vol. 6, Pg. 697, 1982. | |
mouse | LD50 | oral | 7600mg/kg (7600mg/kg) | Drugs in Japan Vol. 6, Pg. 697, 1982. | |
mouse | LD50 | subcutaneous | 1450mg/kg (1450mg/kg) | BEHAVIORAL: MUSCLE WEAKNESS BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | Chemotherapy Vol. 17, Pg. 1523, 1969. |
rabbit | LD50 | intravenous | 710mg/kg (710mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION | Chemotherapy Vol. 17, Pg. 1523, 1969. |
rabbit | LD50 | oral | > 8gm/kg (8000mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) AUTONOMIC NERVOUS SYSTEM: "SMOOTH MUSCLE RELAXANT (MECHANISM UNDEFINED, SPASMOLYTIC)" | Chemotherapy Vol. 17, Pg. 1523, 1969. |
rat | LD50 | intraperitoneal | 1100mg/kg (1100mg/kg) | Drugs in Japan Vol. 6, Pg. 697, 1982. | |
rat | LD50 | intravenous | 680mg/kg (680mg/kg) | Drugs in Japan Vol. 6, Pg. 697, 1982. | |
rat | LD50 | oral | 11gm/kg (11000mg/kg) | Drugs in Japan Vol. 6, Pg. 697, 1982. | |
rat | LD50 | subcutaneous | 2800mg/kg (2800mg/kg) | Drugs in Japan Vol. 6, Pg. 697, 1982. | |
women | TDLo | oral | 120mg/kg/3D-I (120mg/kg) | LIVER: "JAUNDICE, CHOLESTATIC" | American Journal of Gastroenterology. Vol. 82, Pg. 483, 1987. |
women | TDLo | oral | 210mg/kg/7D-I (210mg/kg) | LIVER: "JAUNDICE, CHOLESTATIC" SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), ZONAL" | Australian and New Zealand Journal of Medicine. Vol. 20, Pg. 251, 1990. |