CAS 74431-23-5|Tienamycin|N-formimidoylthienamycin|(5R,6S)-3-({2-[(E)-(aminomethylidene)amino]ethyl}sulfanyl)-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid|IMP|Imipem...

General Information

Structure

Molecular Formula

C₁₂H₁₇N₃O₄S

Molecular Mass

299.34608

Exact Mass

299.09397704

Charge

InChI

InChI=1S/C12H17N3O4S/c1-6(16)9-7-4-8(20-3-2-14-5-13)10(12(18)19)15(7)11(9)17/h5-7,9,16H,2-4H2,1H3,(H2,13,14)(H,18,19)/t6-,7-,9-/m1/s1

InChIKey

ZSKVGTPCRGIANV-ZXFLCMHBSA-N

Canonic Smiles

C[C@H]([C@@H]1[C@H]2CC(=C(N2C1=O)C(=O)O)SCC/N=C/N)O

Isomeric Smiles

S(C1=C(N2[C@@H]([C@H](C2=O)[C@H](O)C)C1)C(=O)O)CC/N=C/N

Calculated Properties

JChem

Acid pKa

3.633336

H Acceptors

H Donor

LogD (pH = 5.5)

-3.8558762

LogD (pH = 7.4)

-3.8512151

Log P

-3.8512225

Molar Refractivity

75.8434

Polarizability

28.54953

Polar Surface Area

116.22

Rotatable Bonds

Lipinski's Rule of Five

true

ALOGPS 2.1

Log P

-0.19

LOG S

-2.59

Solubility (Water)

7.76e-01 g/l

Data Source

Academic Data

Data Source

Names and Identifiers

Synonyms

N-formimidoylthienamycinImipemideImipenemIMPImipenem, n-formimidoyl thienamycin

Brand Name

Tienamycin

IUPAC Traditional name

IPM

IUPAC name

(5R,6S)-3-({2-[(E)-(aminomethylidene)amino]ethyl}sulfanyl)-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid

Names and Identifiers

Registration numbers

PubChem SID

46505744160964835

PubChem CID

104838

CAS Number

74431-23-5

Registration numbers

Properties

Physical Property

Solubility

10 mg/mL [MERCK INDEX (1996)]

Properties

Related Proteins

No Data Available

Click here to submit data

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

DrugBank

DB01598

Drug Groups

approved

Description

Semisynthetic thienamycin that has a wide spectrum of antibacterial activity against gram-negative and gram-positive aerobic and anaerobic bacteria, including many multiresistant strains. It is stable to beta-lactamases. Clinical studies have demonstrated high efficacy in the treatment of infections of various body systems. Its effectiveness is enhanced when it is administered in combination with cilastatin, a renal dipeptidase inhibitor. [PubChem]

Indication

For the treatment of bacterial infections caused by susceptible bacteria.

Pharmacology

Imipenem is a beta-lactam antibiotic belongings to the subgroup of carbapenems. Imipenem has a broad spectrum of activity against aerobic and anaerobic Gram positive as well as Gram negative bacteria. It is particularly important for its activity against Pseudomonas aeruginosa and the Enterococcus species. Imipenem is rapidly degraded by the renal enzyme dehydropeptidase when administered alone, and is always co-administered with cilastatin to prevent this inactivation.

Affected Organisms

Enteric bacteria and other eubacteria

Biotransformation

Renal.

Absorption

Imipenem is not effectively absorbed from the gastrointestinal tract and therefore must be administered parenterally.

Half Life

1 hour

Protein Binding

20% binds to plasma proteins

References

• Kattan JN, Villegas MV, Quinn JP: New developments in carbapenems. Clin Microbiol Infect. 2008 Dec;14(12):1102-11. [Pubmed]

• Pastel DA: Imipenem-cilastatin sodium, a broad-spectrum carbapenem antibiotic combination. Clin Pharm. 1986 Sep;5(9):719-36. [Pubmed]

• Clissold SP, Todd PA, Campoli-Richards DM: Imipenem/cilastatin. A review of its antibacterial activity, pharmacokinetic properties and therapeutic efficacy. Drugs. 1987 Mar;33(3):183-241. [Pubmed]

• Buckley MM, Brogden RN, Barradell LB, Goa KL: Imipenem/cilastatin. A reappraisal of its antibacterial activity, pharmacokinetic properties and therapeutic efficacy. Drugs. 1992 Sep;44(3):408-44. [Pubmed]

• Richerson MA, Ambrose PG, Quintiliani R, Nightingale CH: Formulary review of the carbapenems: comparison of imipenem/cilastatin and meropenem. Conn Med. 1998 Mar;62(3):165-9. [Pubmed]

• Birnbaum J, Kahan FM, Kropp H, MacDonald JS: Carbapenems, a new class of beta-lactam antibiotics. Discovery and development of imipenem/cilastatin. Am J Med. 1985 Jun 7;78(6A):3-21. [Pubmed]

• Hellinger WC, Brewer NS: Imipenem. Mayo Clin Proc. 1991 Oct;66(10):1074-81. [Pubmed]

• Kahan FM, Kropp H, Sundelof JG, Birnbaum J: Thienamycin: development of imipenen-cilastatin. J Antimicrob Chemother. 1983 Dec;12 Suppl D:1-35. [Pubmed]

External Links

• [Wikipedia]

Molecule Details

References

PubChem Literature

From Data Sources

• Clissold SP, Todd PA, Campoli-Richards DM: Imipenem/cilastatin. A review of its antibacterial activity, pharmacokinetic properties and therapeutic efficacy. Drugs. 1987 Mar;33(3):183-241. Pubmed

• Richerson MA, Ambrose PG, Quintiliani R, Nightingale CH: Formulary review of the carbapenems: comparison of imipenem/cilastatin and meropenem. Conn Med. 1998 Mar;62(3):165-9. Pubmed

• Birnbaum J, Kahan FM, Kropp H, MacDonald JS: Carbapenems, a new class of beta-lactam antibiotics. Discovery and development of imipenem/cilastatin. Am J Med. 1985 Jun 7;78(6A):3-21. Pubmed

• Hellinger WC, Brewer NS: Imipenem. Mayo Clin Proc. 1991 Oct;66(10):1074-81. Pubmed

• Kahan FM, Kropp H, Sundelof JG, Birnbaum J: Thienamycin: development of imipenen-cilastatin. J Antimicrob Chemother. 1983 Dec;12 Suppl D:1-35. Pubmed

• Kattan JN, Villegas MV, Quinn JP: New developments in carbapenems. Clin Microbiol Infect. 2008 Dec;14(12):1102-11. Pubmed

• Pastel DA: Imipenem-cilastatin sodium, a broad-spectrum carbapenem antibiotic combination. Clin Pharm. 1986 Sep;5(9):719-36. Pubmed

References

Bioactivity

PubChem BioAssay

Bioactivity

Navigation

General Information

Calculated Properties

• RDKit

• JChem

• ALOGPS 2.1

Data Source

• Academic Data

Names and Identifiers

• Synonyms

• Brand Name

• IUPAC Traditional name

• IUPAC name

Registration numbers

• PubChem SID

• PubChem CID

• CAS Number

• Physical Property

• DrugBank

• PubChem Literature

• From Data Sources

Bioactivity

• PubChem BioAssay

Synonyms

N-formimidoylthienamycinImipemideImipenemIMPImipenem, n-formimidoyl thienamycin

Brand Name

Tienamycin

IUPAC Traditional name

IPM

IUPAC name

(5R,6S)-3-({2-[(E)-(aminomethylidene)amino]ethyl}sulfanyl)-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid

PubChem SID

46505744160964835

CAS Number

74431-23-5

Physical Property

Solubility

10 mg/mL [MERCK INDEX (1996)]

DrugBank

DB01598

Drug Groups

approved

Description

Indication

For the treatment of bacterial infections caused by susceptible bacteria.

Pharmacology

Affected Organisms

Enteric bacteria and other eubacteria

Biotransformation

Renal.

Absorption

Imipenem is not effectively absorbed from the gastrointestinal tract and therefore must be administered parenterally.

Half Life

1 hour

Protein Binding

20% binds to plasma proteins

References

• Kattan JN, Villegas MV, Quinn JP: New developments in carbapenems. Clin Microbiol Infect. 2008 Dec;14(12):1102-11. [Pubmed]

• Pastel DA: Imipenem-cilastatin sodium, a broad-spectrum carbapenem antibiotic combination. Clin Pharm. 1986 Sep;5(9):719-36. [Pubmed]

• Richerson MA, Ambrose PG, Quintiliani R, Nightingale CH: Formulary review of the carbapenems: comparison of imipenem/cilastatin and meropenem. Conn Med. 1998 Mar;62(3):165-9. [Pubmed]

• Birnbaum J, Kahan FM, Kropp H, MacDonald JS: Carbapenems, a new class of beta-lactam antibiotics. Discovery and development of imipenem/cilastatin. Am J Med. 1985 Jun 7;78(6A):3-21. [Pubmed]

• Hellinger WC, Brewer NS: Imipenem. Mayo Clin Proc. 1991 Oct;66(10):1074-81. [Pubmed]

• Kahan FM, Kropp H, Sundelof JG, Birnbaum J: Thienamycin: development of imipenen-cilastatin. J Antimicrob Chemother. 1983 Dec;12 Suppl D:1-35. [Pubmed]

External Links

• [Wikipedia]

From Data Sources

• Clissold SP, Todd PA, Campoli-Richards DM: Imipenem/cilastatin. A review of its antibacterial activity, pharmacokinetic properties and therapeutic efficacy. Drugs. 1987 Mar;33(3):183-241. Pubmed

• Richerson MA, Ambrose PG, Quintiliani R, Nightingale CH: Formulary review of the carbapenems: comparison of imipenem/cilastatin and meropenem. Conn Med. 1998 Mar;62(3):165-9. Pubmed

• Birnbaum J, Kahan FM, Kropp H, MacDonald JS: Carbapenems, a new class of beta-lactam antibiotics. Discovery and development of imipenem/cilastatin. Am J Med. 1985 Jun 7;78(6A):3-21. Pubmed

• Hellinger WC, Brewer NS: Imipenem. Mayo Clin Proc. 1991 Oct;66(10):1074-81. Pubmed

• Kahan FM, Kropp H, Sundelof JG, Birnbaum J: Thienamycin: development of imipenen-cilastatin. J Antimicrob Chemother. 1983 Dec;12 Suppl D:1-35. Pubmed

• Kattan JN, Villegas MV, Quinn JP: New developments in carbapenems. Clin Microbiol Infect. 2008 Dec;14(12):1102-11. Pubmed

• Pastel DA: Imipenem-cilastatin sodium, a broad-spectrum carbapenem antibiotic combination. Clin Pharm. 1986 Sep;5(9):719-36. Pubmed

Molecule

ID:1375