CAS 68373-14-8|CAS 69388-84-7|(2S,5R)-3,3-dimethyl-4,4,7-trioxo-4λ<sup>6</sup>-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid|(2S,5R)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carbo...

General Information

Structure

Molecular Formula

C₈H₁₁NO₅S

Molecular Mass

233.24164

Exact Mass

233.03579346

Charge

InChI

InChI=1S/C8H11NO5S/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)/t5-,6+/m1/s1

InChIKey

FKENQMMABCRJMK-RITPCOANSA-N

Canonic Smiles

OC(=O)[C@@H]1N2C(=O)C[C@H]2S(=O)(=O)C1(C)C

Isomeric Smiles

S1(=O)(=O)C([C@@H](N2[C@H]1CC2=O)C(=O)O)(C)C

Calculated Properties

JChem

LogD (pH = 7.4)

-4.33

LogD (pH = 5.5)

-3.15

Log P

-0.89

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

true

Acid pKa

3.22

Polar Surface Area

91.75

Polarizability

20.64

Molar Refractivity

48.21

LOG S

-1.67

Data Source

Names and Identifiers

IUPAC name

(2S,5R)-3,3-dimethyl-4,4,7-trioxo-4λ⁶-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid (2S,5R)-3,3-dimethyl-4,4,7-trioxo-4λ⁶-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

Synonyms

(2S,5R)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxideBetamazePenicillanic acid dioxideSulbactam Sodium SaltAntibiotic CP 45899SulbactamCP 45899-2Sodium Penicillanate 1,1-DioxidePenicillanic acid 1,1-dioxideUnasyn IM(2S,5R)-3,3-dimethyl-4,4,7-trioxo-4$l^{6}-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acidPenicillanic acid sulfonePenicillanic acid S,S-dioxide(2S,5R)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxideCP 45899Sodium Sulbactam(2S,5R)-3,3-Dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid 4,4-Dioxide Sodium SaltSulbactam Sodium SaltSulbactam3,3-Dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxideSulbactam SodiumPenicillanic Acid 1,1-Dioxide Sodium SaltCP-45,899Sodium 1,1-Dioxypenicillanate(2S,5R)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxidepenicillanic acid 1,1-dioxide(2S,5R)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid 4,4-dioxidesulbactampenicillanic acid sulfone

IUPAC Traditional name

(2S,5R)-3,3-dimethyl-4,4,7-trioxo-4λ⁶-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid sulbactam (2S,5R)-3,3-dimethyl-4,4,7-trioxo-4lambda6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

International Nonproprietary Name (INN)

sulbactamsulbactamum

Names and Identifiers

Registration numbers

CAS Number

MDL Number

EC Number

PubChem CID

PubChem SID

ACToR Database

BKMS React Database

SABIO-RK Database

649165304016730072676602

EnzymePortal Database

Q51355P05193P80545P81781

BRENDA Ligand Database

1420105742

UniProt Database

Q51355P81781P05193Q5YXD6P80545

MetaboLights Database

KEGG DRUG Database

Protein Data Bank

CHEBI ID

LINCS Database

BRENDA Database

Drug Central Database

KEGG ID

CompTox Database

Beilstein Number

Patent number

Wikipedia Title

CHEMBL

SureChEMBL Database

Registration numbers

Properties

Safety Information

European Hazard Symbols

Harmful (Xn)

Download link

Warning

Acute toxicity (oral, dermal, inhalation), category 4

Skin irritation, category 2

Eye irritation, category 2

Skin sensitisation, category 1

Specific Target Organ Toxicity – Single exposure, category 3

H302

2-8°C

-20°C Freezer, Under Inert Atmosphere

Product Information

C8H11NO5S

≥98% (HPLC)

95%

Download link

Antibiotic

Has only weak antibacterial activity except against Neisseria gonorrhoeae; Neisseria meningitidis

Pharmacology Properties

Inhibits beta-lactamases of the Richmond-Sykes types I; II; III; IV; V

Beta-Lactamase inhibitor

Others

Properties

Related Proteins

Molecular Spectra

No Data Available

Click here to submit data

Molecular Spectra

Molecule Details

TRC

S699185

A semi-synthetic β-lactamase inhibitor. It is used in combination with β-lactam antibiotics as antibacterial.

Molecule Details

References

PubChem Literature

From Data Sources

• English, A.R., et al.: Antimicrob. Agents Chemother., 14, 414 (1978)

• Stromberg, B.V., Surg. Gynecol. Obstet., 162, 575 (1978)

• Campoli-Richards, D.M., et al.: Drugs, 33, 577 (1978)

• Mehtar, S., et al.: J. Antimicrob. Chemother., 17, 389 (1978)

• Martindale, The Extra Pharmacopoeia, 32nd edn., Pharmaceutical Press, 1999, 250

• Evrard, E. et al., Nature (London), 1964, 201, 1124, (gc, esters)

• Ger. Pat., 1978, 2 854 535; CA, 90, 121589r, (synth, pharmacol)

• Volkmann, R.A. et al., J.O.C., 1982, 47, 3344, (synth)

• Yang, X. et al., CA, 1986, 104, 224752, (synth)

• Noguchi, J.K. et al., Clin. Pharm., 1988, 7, 37, (rev)

• Gibon, V. et al., Acta Cryst. C, 1988, 44, 652, (cryst struct)

• Howard, A.J. et al., Drugs Exp. Clin. Res., 1979, 5, 7, (pharmacol)

• Foulds, G. et al., Antimicrob. Agents Chemother., 1983, 23, 692, (props)

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, PAP600

• Sheehan, J.C. et al., J.A.C.S., 1953, 75, 3292; 1959, 81, 5838

• Brenner, D.G. et al., Biochemistry, 1981, 20, 3680; 1984, 23, 5833, (synth, props)

• Barrett, A.G.M. et al., J.O.C., 1990, 55, 5110, (synth, ir, pmr, ms)

• Kapur, J.C. et al., Tet. Lett., 1985, 26, 3875, (synth)

References

Bioactivity

PubChem BioAssay

Bioactivity

Registration numbers

CAS Number

MDL Number

EC Number

PubChem CID

PubChem SID

ACToR Database

BKMS React Database

SABIO-RK Database

649165304016730072676602

EnzymePortal Database

Q51355P05193P80545P81781

BRENDA Ligand Database

1420105742

UniProt Database

Q51355P81781P05193Q5YXD6P80545

MetaboLights Database

KEGG DRUG Database

Protein Data Bank

CHEBI ID

LINCS Database

BRENDA Database

Drug Central Database

KEGG ID

CompTox Database

Beilstein Number

Patent number

Wikipedia Title

CHEMBL

SureChEMBL Database

References

PubChem Literature

From Data Sources

• English, A.R., et al.: Antimicrob. Agents Chemother., 14, 414 (1978)

• Stromberg, B.V., Surg. Gynecol. Obstet., 162, 575 (1978)

• Campoli-Richards, D.M., et al.: Drugs, 33, 577 (1978)

• Mehtar, S., et al.: J. Antimicrob. Chemother., 17, 389 (1978)

• Martindale, The Extra Pharmacopoeia, 32nd edn., Pharmaceutical Press, 1999, 250

• Evrard, E. et al., Nature (London), 1964, 201, 1124, (gc, esters)

• Ger. Pat., 1978, 2 854 535; CA, 90, 121589r, (synth, pharmacol)

• Volkmann, R.A. et al., J.O.C., 1982, 47, 3344, (synth)

• Yang, X. et al., CA, 1986, 104, 224752, (synth)

• Noguchi, J.K. et al., Clin. Pharm., 1988, 7, 37, (rev)

• Gibon, V. et al., Acta Cryst. C, 1988, 44, 652, (cryst struct)

• Howard, A.J. et al., Drugs Exp. Clin. Res., 1979, 5, 7, (pharmacol)

• Foulds, G. et al., Antimicrob. Agents Chemother., 1983, 23, 692, (props)

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, PAP600

• Sheehan, J.C. et al., J.A.C.S., 1953, 75, 3292; 1959, 81, 5838

• Brenner, D.G. et al., Biochemistry, 1981, 20, 3680; 1984, 23, 5833, (synth, props)

• Barrett, A.G.M. et al., J.O.C., 1990, 55, 5110, (synth, ir, pmr, ms)

• Kapur, J.C. et al., Tet. Lett., 1985, 26, 3875, (synth)

Bioactivity

PubChem BioAssay

Molecule Details

TRC

S699185

A semi-synthetic β-lactamase inhibitor. It is used in combination with β-lactam antibiotics as antibacterial.

Properties

Safety Information

European Hazard Symbols

Harmful (Xn)

Download link

Warning

Acute toxicity (oral, dermal, inhalation), category 4

Skin irritation, category 2

Eye irritation, category 2

Skin sensitisation, category 1

Specific Target Organ Toxicity – Single exposure, category 3

H302

2-8°C

-20°C Freezer, Under Inert Atmosphere

Product Information

C8H11NO5S

≥98% (HPLC)

95%

Download link

Antibiotic

Has only weak antibacterial activity except against Neisseria gonorrhoeae; Neisseria meningitidis

Pharmacology Properties

Inhibits beta-lactamases of the Richmond-Sykes types I; II; III; IV; V

Beta-Lactamase inhibitor

Others

Molecular Spectra

No Data Available

Click here to submit data

Names and Identifiers

IUPAC name

(2S,5R)-3,3-dimethyl-4,4,7-trioxo-4λ⁶-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid (2S,5R)-3,3-dimethyl-4,4,7-trioxo-4λ⁶-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

Synonyms

IUPAC Traditional name

(2S,5R)-3,3-dimethyl-4,4,7-trioxo-4λ⁶-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid sulbactam (2S,5R)-3,3-dimethyl-4,4,7-trioxo-4lambda6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

International Nonproprietary Name (INN)

sulbactamsulbactamum

Molecule

ID:119446