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1847-24-1

Basic Information
CAS No.: 1847-24-1
Name: Flucloxacillin sodium
Article Data: 5
Molecular Structure:
Molecular Structure of 1847-24-1 (Flucloxacillin sodium)
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
Synthetic route
1847-24-1

Flucloxacillin sodium

Conditions
ConditionsYield
With sodium isooctanoate In ethyl acetate Solvent;90.6%
387-45-1

2-chloro-6-fluorobenzaldehyde

1847-24-1

Flucloxacillin sodium

Conditions
ConditionsYield
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
551-16-6

6-Aminopenicillanic Acid

3-(2-chloro-6-fluorophenyl)-5-methylisoxazole-4-carbonyl chloride

1847-24-1

Flucloxacillin sodium

Conditions
ConditionsYield
With ammonium hydroxide In ethyl acetate pH=2 - 9;
3919-74-2

3-(2-chloro-6-flourophenyl)-5-methyl-isoxazole-4-carboxylic acid

1847-24-1

Flucloxacillin sodium

Conditions
ConditionsYield
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

flushloxilin triethylamine

1847-24-1

Flucloxacillin sodium

Conditions
ConditionsYield
With sodium isooctanoate In water; ethyl acetate; acetone at 20 - 25℃; for 3h; Time;20.3 g
551-16-6

6-Aminopenicillanic Acid

C18H10ClFN2O2S2

1847-24-1

Flucloxacillin sodium

Conditions
ConditionsYield
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;
1847-24-1

Flucloxacillin sodium

A

75524-31-1

5-Hydroxymethylflucloxacillin

B

(5R)-flucloxacillin penicilloic acid

C

(5S)-flucloxacillin penicilloic acid

Conditions
ConditionsYield
With metabolism in male albino rat
Raw Materials
387-45-1
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 CAS 1847-24-1

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Specification

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.