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Chemistry

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Also known as: 85960-17-4, Sodium;(z)-7-[(2r)-2-amino-2-carboxyethyl]sulfanyl-2-[[(1s)-2,2-dimethylcyclopropanecarbonyl]amino]hept-2-enoate;(5r,6s)-3-[2-(aminomethylideneamino)ethylsulfanyl]-6-[(1r)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid, Imipenem + cilastatin, Imipenem-cilastatin sodium, Imipenem-cilastatin sodium mixt., Dtxsid60873393
Molecular Formula
C28H42N5NaO9S2
Molecular Weight
679.8  g/mol
InChI Key
VEVHCKVFLWYWCN-KJWPAVRRSA-M

Imipenem + Cilastatin
Combination of imipenem and cilastatin that is used in the treatment of bacterial infections; cilastatin inhibits renal dehydropeptidase I to prolong the half-life and increase the tissue penetration of imipenem, enhancing its efficacy as an anti-bacterial agent.
1 2D Structure

Imipenem + Cilastatin

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
sodium;(Z)-7-[(2R)-2-amino-2-carboxyethyl]sulfanyl-2-[[(1S)-2,2-dimethylcyclopropanecarbonyl]amino]hept-2-enoate;(5R,6S)-3-[2-(aminomethylideneamino)ethylsulfanyl]-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
2.1.2 InChI
InChI=1S/C16H26N2O5S.C12H17N3O4S.Na/c1-16(2)8-10(16)13(19)18-12(15(22)23)6-4-3-5-7-24-9-11(17)14(20)21;1-6(16)9-7-4-8(20-3-2-14-5-13)10(12(18)19)15(7)11(9)17;/h6,10-11H,3-5,7-9,17H2,1-2H3,(H,18,19)(H,20,21)(H,22,23);5-7,9,16H,2-4H2,1H3,(H2,13,14)(H,18,19);/q;;+1/p-1/b12-6-;;/t10-,11+;6-,7-,9-;/m11./s1
2.1.3 InChI Key
VEVHCKVFLWYWCN-KJWPAVRRSA-M
2.1.4 Canonical SMILES
CC(C1C2CC(=C(N2C1=O)C(=O)O)SCCN=CN)O.CC1(CC1C(=O)NC(=CCCCCSCC(C(=O)O)N)C(=O)[O-])C.[Na+]
2.1.5 Isomeric SMILES
C[C@H]([C@@H]1[C@H]2CC(=C(N2C1=O)C(=O)O)SCCN=CN)O.CC1(C[C@@H]1C(=O)N/C(=C\CCCCSC[C@@H](C(=O)O)N)/C(=O)[O-])C.[Na+]
2.2 Synonyms
2.2.1 MeSH Synonyms

1. Cilastatin, Imipenem

2. Cilastatin, Imipenem Drug Combination

3. Imipenem - Cilastatin

4. Imipenem - Cilastatin Sodium

5. Imipenem Cilastatin

6. Imipenem Cilastatin Sodium

7. Imipenem Cilastatin, Sodium Salt

8. Imipenem-cilastatin

9. Imipenem-cilastatin Sodium

10. Imipenem-cilastatin, Sodium Salt

11. Mk 0787 Mk 0791 Mixture

12. Mk 0787-mk 0791 Mixture

13. Mk 787 Mk 791 Mixture

14. Mk 787-mk 791 Mixture

15. Primaxin

16. Thienam

17. Tienam 500

18. Zienam

2.2.2 Depositor-Supplied Synonyms

1. 85960-17-4

2. Sodium;(z)-7-[(2r)-2-amino-2-carboxyethyl]sulfanyl-2-[[(1s)-2,2-dimethylcyclopropanecarbonyl]amino]hept-2-enoate;(5r,6s)-3-[2-(aminomethylideneamino)ethylsulfanyl]-6-[(1r)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic Acid

3. Imipenem + Cilastatin

4. Imipenem-cilastatin Sodium

5. Imipenem-cilastatin Sodium Mixt.

6. Dtxsid60873393

7. Mfcd01744417

8. Cilastatin Sodium Mixture With Imipenem

9. Imipenem Combination With Cilastatin Sodium

10. Mk-0787 / Mk-0791 (1:1)

11. 1-azabicyclo(3.2.0)hept-2-ene-2-carboxylic Acid, 6-(1-hydroxyethyl)-3-((2-((iminomethyl)amino)ethyl)amino)-7-oxo-, (5r-(5-alpha,6-alpha(r*)))-, Mixt. With (r-(r*,s*-(z)))-7-((2-amino-2-carboxyethyl)thio)-2-(((2,2-dimethylcyclopropyl)carbonyl)amino)-2-heptenoic Acid Monosodium Salt

2.3 Create Date
2008-02-05
3 Chemical and Physical Properties
Molecular Weight 679.8 g/mol
Molecular Formula C28H42N5NaO9S2
Hydrogen Bond Donor Count6
Hydrogen Bond Acceptor Count13
Rotatable Bond Count17
Exact Mass679.23216456 g/mol
Monoisotopic Mass679.23216456 g/mol
Topological Polar Surface Area299 Ų
Heavy Atom Count45
Formal Charge0
Complexity1020
Isotope Atom Count0
Defined Atom Stereocenter Count5
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count3
4 Pharmacology and Biochemistry
4.1 MeSH Pharmacological Classification

Anti-Bacterial Agents

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


Protease Inhibitors

Compounds which inhibit or antagonize biosynthesis or actions of proteases (ENDOPEPTIDASES). (See all compounds classified as Protease Inhibitors.)


4.2 FDA Pharmacological Classification
4.2.1 Pharmacological Classes
Dipeptidase Inhibitors [MoA]; Penem Antibacterial [EPC]; Renal Dehydropeptidase Inhibitor [EPC]; Carbapenems [CS]

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