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Also known as: Ertapenem sodium, Ertapenem monosodium, Ertapenem sodium [usan], Ertapenem monosodium (90per cent), 153773-82-1, Mk 0826

Molecular Formula

C₂₂H₂₄N₃NaO₇S

Molecular Weight

497.5 g/mol

InChI Key

ZXNAQFZBWUNWJM-HRXMHBOMSA-M

A carbapenem derivative antibacterial agent that is more stable to renal dehydropeptidase I than IMIPENEM, but does not need to be given with an enzyme inhibitor such as CILASTATIN. It is used in the treatment of Gram-positive and Gram-negative bacterial infections including intra-abdominal infections, acute gynecological infections, complicated urinary tract infections, skin infections, and respiratory tract infections. It is also used to prevent infection in colorectal surgery.

1 2D Structure

Ertapenem Sodium

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

sodium;(4R,5S,6S)-3-[(3S,5S)-5-[(3-carboxylatophenyl)carbamoyl]pyrrolidin-1-ium-3-yl]sulfanyl-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

2.1.2 InChI

InChI=1S/C22H25N3O7S.Na/c1-9-16-15(10(2)26)20(28)25(16)17(22(31)32)18(9)33-13-7-14(23-8-13)19(27)24-12-5-3-4-11(6-12)21(29)30;/h3-6,9-10,13-16,23,26H,7-8H2,1-2H3,(H,24,27)(H,29,30)(H,31,32);/q;+1/p-1/t9-,10-,13+,14+,15-,16-;/m1./s1

2.1.3 InChI Key

ZXNAQFZBWUNWJM-HRXMHBOMSA-M

2.1.4 Canonical SMILES

CC1C2C(C(=O)N2C(=C1SC3CC([NH2+]C3)C(=O)NC4=CC=CC(=C4)C(=O)[O-])C(=O)[O-])C(C)O.[Na+]

2.1.5 Isomeric SMILES

C[C@@H]1[C@@H]2[C@H](C(=O)N2C(=C1S[C@H]3C[C@H]([NH2+]C3)C(=O)NC4=CC=CC(=C4)C(=O)[O-])C(=O)[O-])[C@@H](C)O.[Na+]

2.2 Synonyms

2.2.1 MeSH Synonyms

1. Ertapenem

2. Ertapenem Sodium

3. Invanoz

2.2.2 Depositor-Supplied Synonyms

1. Ertapenem Sodium

2. Ertapenem Monosodium

3. Ertapenem Sodium [usan]

4. Ertapenem Monosodium (90per Cent)

5. 153773-82-1

6. Mk 0826

7. Sodium;(4r,5s,6s)-3-[(3s,5s)-5-[(3-carboxylatophenyl)carbamoyl]pyrrolidin-1-ium-3-yl]sulfanyl-6-[(1r)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

8. 2t90ke67l0

9. Mk 826

10. Unii-2t90ke67l0

11. L 749345

12. 1-azabicyclo(3.2.0)hept-2-ene-2-carboxylic Acid, 3-(((3s,5s)-5-(((3-carboxyphenyl)amino)carbonyl)-3-pyrrolidinyl)thio)-6-((1r)-1-hydroxyethyl)-4-methyl-7-oxo-, Monosodium Salt, (4r,5s,6s)-

13. 1-azabicyclo(3.2.0)hept-2-ene-2-carboxylic Acid, 3-((5-(((3-carboxyphenyl)amino)carbonyl)-3-pyrrolidinyl)thio)-6-((1r)-1-hydroxyethyl)-4-methyl-7-oxo-, Monosodium Salt, (4r-(3(3s*,5s*),4alpha,5beta,6beta(r*)))-

14. Sodium (4r,5s,6s)-3-({(3s,5s)-5-[(3-carboxylatophenyl)carbamoyl]pyrrolidinium-3-yl}sulfanyl)-6-[(1r)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

15. Sodium (4r,5s,6s)-3-({(3s,5s)-5-[(m-carboxylatophenyl)carbamoyl]pyrrolidinium-3-yl}sulfanyl)-6-[(1r)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

16. Sodium (4r,5s,6s)-3-({(3s,5s)-5-[(m-carboxyphenyl)carbamoyl]-3-pyrrolidinyl}thio)-6-[(1r)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

2.3 Create Date

2006-10-26

3 Chemical and Physical Properties

Molecular Formula	C₂₂H₂₄N₃NaO₇S
Molecular Weight	497.5 g/mol
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	5
Exact Mass	497.12326557 g/mol
Monoisotopic Mass	497.12326557 g/mol
Topological Polar Surface Area	192 Å²
Heavy Atom Count	34
Formal Charge	0
Complexity	882
Isotope Atom Count	0
Defined Atom Stereocenter Count	6
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

4 Drug and Medication Information

4.1 Drug Indication

* Treatment:

Treatment of the following infections when caused by bacteria known or very likely to be susceptible to ertapenem and when parenteral therapy is required:

- intra-abdominal infections;

- community-acquired pneumonia;

- acute gynaecological infections;

- diabetic foot infections of the skin and soft tissue.

* Prevention:

Invanz is indicated in adults for the prophylaxis of surgical site infection following elective colorectal surgery.

Consideration should be given to official guidance on the appropriate use of antibacterial agents.

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Anti-Bacterial Agents

Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)

5.2 FDA Pharmacological Classification

5.2.1 Pharmacological Classes

Penem Antibacterial [EPC]; Carbapenems [CS]

5.3 ATC Code

J01DH03

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