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Sulbactam sodium
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Name

Sulbactam sodium

 EINECS 273-984-4
CAS No. 69388-84-7 Density N/A
PSA 102.96000 LogP -1.11100
Solubility N/A Melting Point 121-123°C(lit.)
Formula C8H10NNaO5S Boiling Point 567.7oC at 760 mmHg
Molecular Weight 255.227 Flash Point 297.1oC
Transport Information N/A Appearance COA
Safety 22-24-36/37-45 Risk Codes 42/43
Molecular Structure Molecular Structure of 69388-84-7 (Sulbactam sodium) Hazard Symbols HarmfulXn
Synonyms

4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid, 3,3-dimethyl-7-oxo-, 4,4-dioxide, sodium salt, (2S,5R)- (9CI);Penicillanic acid 1,1-dioxidesodium salt;Sodium 1,1-dioxypenicillanate;Sodium penicillanate 1,1-dioxide;Sodium sulbactam;Sulbactam sodium salt;Unasyn IM;

Article Data 7

Sulbactam sodium Synthetic route

68373-14-8

sulbactum

69388-84-7

sodium sulbactam

Conditions
ConditionsYield
With sodium isooctanoate In ethyl acetate99.3%
With sodium 2-ethylhexanoic acid In water; isopropyl alcohol at 20 - 35℃; for 2.33333h;95%
With sodium acetate; sodium hydrogencarbonate at 20 - 25℃; pH=5.5 - 6;
With sodium isooctanoate In methanol; water at 25℃; pH=4.5; Reagent/catalyst; Solvent; Temperature; pH-value;542g
87-53-6

penicillanic acid

69388-84-7

sodium sulbactam

Conditions
ConditionsYield
Stage #1: penicillanic acid With potassium permanganate; sulfuric acid; acetic acid In water at 5 - 8℃; for 2.5h; Heating;
Stage #2: With sodium acetate; pyrographite In ethanol at 40℃; for 1h; Solvent;		95.3%
tetrabis(triphenylphosphine)palladium

tetrabis(triphenylphosphine)palladium

762-04-9, 123-22-8

Diethyl phosphonate

114333-65-2

allyl 6,6-dibromopenicillanate 1,1-dioxide

sodium 2-ethylhexanoic acid

69388-84-7

sodium sulbactam

Conditions
ConditionsYield
With sodium hydrogencarbonate; triethylamine; triphenylphosphine In water; ethyl acetate2.22 g (87%)
762-04-9, 123-22-8

Diethyl phosphonate

76646-91-8

6,6-dibromopenicillanic acid-1,1-dioxide

69388-84-7

sodium sulbactam

Conditions
ConditionsYield
With sodium hydrogencarbonate In water; ethyl acetate9.78 g (76.5%)
551-16-6

6-Aminopenicillanic Acid

69388-84-7

sodium sulbactam

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: bromine; sulfuric acid; sodium nitrite / ethyl acetate / 1 h / 5 °C
2.1: potassium permanganate; sodium hydroxide; phosphoric acid / water / 0.5 h / 0 °C / pH 5.7
3.1: zinc / water / 0 °C / pH 1.5 - 5.8
3.2: 1 h
View Scheme
Multi-step reaction with 4 steps
1.1: hydrogen bromide; sodium nitrite; sulfuric acid / water / 1.5 h / 0 - 5 °C / pH Ca. 2.5
1.2: 1 h / 0 - 5 °C
2.1: sodium hydroxide; water; potassium permanganate; phosphoric acid / 0 - 5 °C
3.1: zinc / water / 1.5 h / 0 °C / pH Ca. 3.5
4.1: sodium isooctanoate / ethyl acetate
View Scheme
76646-91-8

6,6-dibromopenicillanic acid-1,1-dioxide

69388-84-7

sodium sulbactam

Conditions
ConditionsYield
Stage #1: 6,6-dibromopenicillanic acid-1,1-dioxide With zinc In water at 0℃; pH=1.5 - 5.8;
Stage #2: With sodium 2-ethylhexanoic acid In water; acetone for 1h; Temperature;		288.1 g
24158-88-1

6,6-dibromopenicillanic acid

69388-84-7

sodium sulbactam

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium hydroxide; water; potassium permanganate; phosphoric acid / 0 - 5 °C
2: zinc / water / 1.5 h / 0 °C / pH Ca. 3.5
3: sodium isooctanoate / ethyl acetate
View Scheme
69388-84-7

sodium sulbactam

68373-14-8

sulbactum

Conditions
ConditionsYield
With tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide In dichloromethane; water at 20℃; for 0.166667h; pH=6.9 - 7;94.8%
With hydrogenchloride In water; ethyl acetate87.2%
Multi-step reaction with 2 steps
1: 86 percent / hexamethylphosphoric acid triamide / 18 h / 55 °C
2: 99 percent / sodium p-toluenesulfinate tetrahydrate, Pd(PPh3)4 / methanol; tetrahydrofuran / 1 h / Ambient temperature
View Scheme
4860-96-2

3-bromo-2-chloroprop-1-ene

69388-84-7

sodium sulbactam

(2S,5R)-3,3-Dimethyl-4,4,7-trioxo-4λ6-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 2-chloro-allyl ester

Conditions
ConditionsYield
In N,N,N,N,N,N-hexamethylphosphoric triamide at 55℃; for 18h;86%
18997-19-8

Chloromethyl pivalate

69388-84-7

sodium sulbactam

69388-79-0

(pivaloyloxy)methyl 6,6-dihydropenicillanate S,S-dioxide

Conditions
ConditionsYield
In dimethyl sulfoxide at 20 - 25℃; for 18h; Substitution;85%
With tetrabutylammomium bromide In acetone for 18h; Heating;

Sulbactam sodium Chemical Properties

Molecular Structure:

Molecular Formula: C8H10NNaO5S
Molecular Weight: 255.2235
IUPAC Name: Sodium 3,3-dimethyl-4,4,7-trioxo-4$l^{6}-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
Synonyms of Penicillanic acid sulfone sodium salt (CAS NO.69388-84-7): Sulbactam sodium [USAN:JAN] ; Unasyn ; 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-, 4,4-dioxide, sodium salt, (2S-cis)- ; CP 45899 sodium salt ; CP 45899-2 ; EINECS 273-984-4 ; Penicillanic acid 1,1-dioxide sodium salt ; Penicillanic acid dioxide sodium salt ; Sodium (2S,5R)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylate 4,4-dioxide ; Sodium 1,1-dioxopenicillanate ; Sodium penicillanate 1,1-dioxide ; Sodium sulbactam ; Sulbactam natrium ; Sulbactam sodium ; UNII-DKQ4T82YE6 ; Sodium (2S-cis)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylate 4,4-dioxide
CAS NO: 69388-84-7
Classification Code: Drug / Therapeutic Agent ; Inhibitor [beta-lactamase] ; Reproductive Effect ; Synergist [penicillin/cephalosporin] ; Synergist [penicillincephalosporin] 
H bond acceptors: 6
H bond donors: 1
Freely Rotating Bonds: 1
Polar Surface Area: 102.96 Å2 
SMILES: [Na+].O=S2(=O)C([C@@H](N1C(=O)C[C@H]12)C([O-])=O)(C)C 
InChI: InChI=1/C8H11NO5S.Na/c1-8(2)6(7(11)12)9-4(10)3-5(9)15(8,13)14;/h5-6H,3H2,1-2H3,(H,11,12);/q;+1/p-1/t5-,6+;/m1./s1 
InChIKey: NKZMPZCWBSWAOX-OTSBDZIMBK
Std. InChI: InChI=1S/C8H11NO5S.Na/c1-8(2)6(7(11)12)9-4(10)3-5(9)15(8,13)14;/h5-6H,3H2,1-2H3,(H,11,12);/q;+1/p-1/t5-,6+;/m1./s1 
Std. InChIKey: NKZMPZCWBSWAOX-IBTYICNHSA-M
 

 

Sulbactam sodium Uses

 Penicillanic acid sulfone sodium salt (CAS NO.69388-84-7) is  β-lactamase inhibitor for the production of antibiotic class medicine.

Sulbactam sodium Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal > 6gm/kg (6000mg/kg) SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)		 Chemotherapy Vol. 32(Suppl,
mouse LD50 intravenous 8100ug/kg (8.1mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 17, Pg. 1106, 1986.
mouse LD50 subcutaneous > 6gm/kg (6000mg/kg) SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)		 Chemotherapy Vol. 32(Suppl,
rat LD50 intraperitoneal > 6gm/kg (6000mg/kg) SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)		 Chemotherapy Vol. 32(Suppl,
rat LD50 intravenous 6500mg/kg (6500mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION		 Chemotherapy Vol. 32(Suppl,
rat LD50 subcutaneous > 6gm/kg (6000mg/kg) SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)		 Chemotherapy Vol. 32(Suppl,

Sulbactam sodium Safety Profile

Safety Information of Penicillanic acid sulfone sodium salt (CAS NO.69388-84-7)
Hazard Codes:Xn
Risk Statements:42/43
42/43:May cause sensitization by inhalation and skin contact  
Safety Statements:22-24-36/37-45
22:Do not breathe dust  
24:Avoid contact with skin 
36/37:Wear suitable protective clothing and gloves 
45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)
Poison by intravenous route. Experimental reproductive effects. When heated to decomposition it emits toxic fumes of NOx and SOx.

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