Sulbactam

HCID 130313

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Basic information

CAS
68373-14-8
Standard SMILES
CC1(C)[C@H](C(=O)O)N2C(=O)C[C@H]2S1(=O)=O
InChIKey
FKENQMMABCRJMK-RITPCOANSA-N
Molecular formula
C8H11NO5S
Average molar mass
233.24 g/mol
Monoisotopic mass
233.03579362

Names & identifiers

Preferred name
Sulbactam
IUPAC
(2S,5R)-3,3-dimethyl-4,4,7-trioxo-4lambda6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

Names & synonyms

SULBACTAM68373-14-8SulbactamumBetamaze(2S,5R)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxidePenicillanic Acid Sulfonepenicillanic acid 1,1-dioxide(2S,5R)-3,3-Dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid 4,4-dioxideDTXSID1023605S4TF6I2330NSC-759886CP 45899
Show more names
CP-458992CHEBI:9321DTXCID5036052,2-dimethyl-1,1-dioxidopenam-3alpha-carboxylic acidCP45899CP-458994-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-, 4,4-dioxide, (2S-cis)-4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-, 4,4-dioxide, (2S-cis)-

Database identifiers

CAS
68373-14-8
PubChem CID
130313
DTXSID
DTXSID1023605
ChEMBL
CHEMBL403
ChEBI
CHEBI:9321
UNII
S4TF6I2330
EC Number
269-878-2
Nikkaji
J689.013J

Properties

Computed structural propertiesFilling in

XLogP
-1
Topological polar surface area
100 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
5
Rotatable bonds
1
Heavy atoms
15

Experimental & physicochemical properties

Melting Point156

Safety & regulation

GHS classification

GHS Classification · 6 items

This chemical does not meet GHS hazard criteria for 1.2% (1 of 80) of reports.

Danger

H302 (51.2%): Harmful if swallowed [Warning Acute toxicity, oral];H317 (47.5%): May cause an allergic skin reaction [Warning Sensitization, Skin];H334 (47.5%): May cause allergy or asthma symptoms or breathing difficulties if inhaled [Danger Sensitization, respiratory]

P233, P260, P261, P264, P270, P271, P272, P280, P284, P301+P317, P302+P352, P304+P340, P321, P330, P333+P317, P342+P316, P362+P364, P403, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 80 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.;Reported as not meeting GHS hazard criteria per 1 of 80 reports by companies.;There are 6 notifications provided by 79 of 80 reports by companies with hazard statement code(s).;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Hazard information

Regulatory Information · 2 items

Status: Active Update: 05-05-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/23709

4-Thia-1-azabicyclo3.2.0heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-, 4,4-dioxide, (2S,5R)-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

Hazard Classes and CategoriesAcute Tox. 4 (51.2%);Skin Sens. 1 (47.5%);Resp. Sens. 1 (47.5%)

Regulatory information

Regulatory Information · 2 items

Status: Active Update: 05-05-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/23709

4-Thia-1-azabicyclo3.2.0heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-, 4,4-dioxide, (2S,5R)-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

Chemistry & industry

Pharmacology

ATC Code · 2 items

J - Antiinfectives for systemic use;J01 - Antibacterials for systemic use;J01C - Beta-lactam antibacterials, penicillins;J01CG - Beta-lactamase inhibitors;J01CG01 - Sulbactam

QJ - Antiinfectives for systemic use;QJ01 - Antibacterials for systemic use;QJ01C - Beta-lactam antibacterials, penicillins;QJ01CG - Beta-lactamase inhibitors;QJ01CG01 - Sulbactam

Protein BindingSulbactam is approximately 38% reversibly bound to plasma proteins.
Pharmacodynamics · 1 item

When given together with beta-lactam antibiotics, sulbactam broadens their antibacterial spectrum by blocking the enzyme involved in their hydrolysis. Sulbactam alone possesses weak intrinsic antibacterial activity except against the _Neisseriaceae_, _Acinetobacter spp._, and _Bacteroides fragilis_ as it can bind to the penicillin-binding proteins. Sulbactam restores the activity of beta-lactam antibiotics against a range of beta-lactamase-producing gram-positive and gram-negative bacteria.

Mechanism of ActionSulbactam is a competitive, irreversible bacterial beta (β)-lactamase inhibitor. It is reported to be more potent against class C beta-lactamases.
Biological Half-LifeIn healthy volunteers, the half-life is approximately one hour.
Metabolism/MetabolitesMetabolism of sulbactam has not been characterized.

Uses & manufacturing

Uses · 1 item

Use (kg; approx.) in Germany (2009): >10000;Use (kg; exact) in Germany (2009): 27580;Use (kg) in USA (2002): 6920;Consumption (g per capita; approx.) in Germany (2009): 0.122;Consumption (g per capita; exact) in Germany (2009): 0.337;Consumption (g per capita) in the USA (2002): 0.0245;Excretion rate: 0.8;Calculated removal (%): 75.1

Suppliers100 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
广州隽沐生物科技股份有限公司020-36607679; 13502246435 · [email protected]

Related reactions

15 records

Compound notes

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