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Imipenem, イミペネム水和物

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ChemSpider 2D Image | Imipenem hydrate | C12H19N3O5S

74431-23-5.png

Imipenem

イミペネム水和物

Cas 74431-23-5

  • Molecular FormulaC12H19N3O5S
  • Average mass317.361 Da

(5R,6S)-3-((2-(Formimidoylamino)ethyl)thio)-6-((R)-1-hydroxyethyl)-7-oxo-1-azabicyclo(3.2.0)hept-2-ene-2-carboxylic acid monohydrate

1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid, 6-[(1R)-1-hydroxyethyl]-3-[[2-[(iminomethyl)amino]ethyl]thio]-7-oxo-, (5R,6S)-, monohydrate
264-734-5 [EINECS]
74431-23-5 [RN]
N-Formimidoylthienamycin Monohydrate
Primaxin monohydrate
Tienam monohydrate
(5R,6S)-3-((2-Formimidamidoethyl)thio)-6-((R)-1-hydroxyethyl)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid hydrate
(5R,6S)-3-[2-(aminomethylideneamino)ethylsulfanyl]-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid and hydrate
8174596 [Beilstein]
imipemide monohydrate

Antibacterial, Cell wall biosynthesis inhibitor

Imipenem
CAS Registry Number: 74431-23-5; 64221-86-9 (anhydrous)
CAS Name: (5R,6S)-6-[(1R)-1-Hydroxyethyl]-3-[[2-[(iminomethyl)amino]ethyl]thio]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid monohydrate
Additional Names: N-formimidoylthienamycin monohydrate; imipemide
Manufacturers’ Codes: MK-787
Molecular Formula: C12H17N3O4S.H2O
Molecular Weight: 317.36
Percent Composition: C 45.41%, H 6.03%, N 13.24%, O 25.21%, S 10.10%
Literature References: Extremely broad-spectrum semi-synthetic antibiotic; first stable derivative of thienamycin, q.v. Prepn: W. J. Leanza et al., J. Med. Chem. 22, 1435 (1979); T. W. Miller, EP 6639 (1980 to Merck & Co.), C.A. 93, 155845y (1980); B. G. Christensen et al., US 4194047 (1980 to Merck & Co.). Totally synthetic prepn without formation of thienamycin: I. Shinkai et al.,Tetrahedron Lett. 23, 4903 (1982). HPLC determn in serum: C. M. Myers, J. L. Blumer, Antimicrob. Agents Chemother. 26, 78 (1984). Series of articles on in vitro activity, pharmacokinetics, clinical efficacy of combination with cilastatin sodium, q.v., a renal dehydropeptidase I inhibitor: J. Antimicrob. Chemother. 12, Suppl. D, 1-155 (1983); Rev. Infect. Dis. 7, Suppl. 3, S389-S536 (1985); Am. J. Med. 78, Suppl. 6A, 1-167 (1985); Infection 14, Suppl. 2, S111-S180 (1986). Comprehensive description: E. R. Oberholtzer, Anal. Profiles Drug Subs. 17, 73-114 (1988).
Properties: Crystals from water-ethanol. [a]D25 +86.8° (c = 0.05 in 0.1M phosphate, pH 7). pKa1 ~3.2, pKa2 ~9.9. uv max (water): 299 nm (e 9670, 98% NH2OH ext). Soly (mg/ml): water 10, methanol 5, ethanol 0.2, acetone <0.1, dimethylformamide <0.1, dimethylsulfoxide 0.3.
pKa: pKa1 ~3.2, pKa2 ~9.9
Optical Rotation: [a]D25 +86.8° (c = 0.05 in 0.1M phosphate, pH 7)
Absorption maximum: uv max (water): 299 nm (e 9670, 98% NH2OH ext)
Derivative Type: Combination with cilastatin sodium
CAS Registry Number: 85960-17-4
Trademarks: Imipem (Neopharmed); Primaxin (Merck & Co.); Tenacid (Sigma-Tau); Tienam (Merck & Co.); Zienam (Merck & Co.)
Therap-Cat: Antibacterial.
Keywords: Antibacterial (Antibiotics); ?Lactams; Carbapenems.

Imipenem (Primaxin among others) is an intravenous β-lactam antibiotic discovered by Merck scientists Burton Christensen, William Leanza, and Kenneth Wildonger in the mid-1970s.[1] Carbapenems are highly resistant to the β-lactamase enzymes produced by many multiple drug-resistant Gram-negative bacteria,[2] thus play a key role in the treatment of infections not readily treated with other antibiotics.[3]

Imipenem was patented in 1975 and approved for medical use in 1985.[4] It was discovered via a lengthy trial-and-error search for a more stable version of the natural product thienamycin, which is produced by the bacterium Streptomyces cattleya. Thienamycin has antibacterial activity, but is unstable in aqueous solution, so impractical to administer to patients.[5] Imipenem has a broad spectrum of activity against aerobic and anaerobicGram-positive and Gram-negative bacteria.[6] It is particularly important for its activity against Pseudomonas aeruginosa and the Enterococcus species. It is not active against MRSA, however.

Medical uses

Spectrum of bacterial susceptibility and resistance

Acinetobacter anitratusAcinetobacter calcoaceticusActinomyces odontolyticusAeromonas hydrophilaBacteroides distasonisBacteroides uniformis, and Clostridium perfringens are generally susceptible to imipenem, while Acinetobacter baumannii, some Acinetobacter spp., Bacteroides fragilis, and Enterococcus faecalis have developed resistance to imipenem to varying degrees. Not many species are resistant to imipenem except Pseudomonas aeruginosa (Oman) and Stenotrophomonas maltophilia.[7]

Coadministration with cilastatin

Imipenem is rapidly degraded by the renal enzyme dehydropeptidase 1 when administered alone, and is almost always coadministered with cilastatin to prevent this inactivation[8]

Adverse effects

Common adverse drug reactions are nausea and vomiting. People who are allergic to penicillin and other β-lactam antibiotics should take caution if taking imipenem, as cross-reactivity rates are high. At high doses, imipenem is seizurogenic.[9]

Mechanism of action

Imipenem acts as an antimicrobial through inhibiting cell wall synthesis of various Gram-positive and Gram-negative bacteria. It remains very stable in the presence of β-lactamase (both penicillinase and cephalosporinase) produced by some bacteria, and is a strong inhibitor of β-lactamases from some Gram-negative bacteria that are resistant to most β-lactam antibiotics.

SYM

By reaction of thienamycin (I) with methyl formimidate (II) by means of NaOH in water.

DE 2652679; FR 2332012; GB 1570990; NL 7612939

SYN 2

WO 0294828

The reaction of (3R,5R,6S)-6-(1(R)-hydroxyethyl)-2-oxo-1-carbapenem-3-carboxylic acid p-nitrobenzyl ester (I) with diphenyl chlorophosphate by (II) means of DMAP and DIEA in DMA/dichloromethane gives the enol phosphate (III), which is condensed with 2-aminoethanethiol (IV) in DMA to yield the 2-aminoethylsulfanyl derivative (V). The reaction of (V) with benzyl formimidate (VI) by means of DIEA in DMA affords the intermediate p-nitrobenzyl ester (VII), which is finally hydrogenated with H2 over Pd/C in water/isopropanol/N-methylmorpholine to provide the target Imipemide.

SYN 3

Tetrahedron Lett 1982,23(47),4903

The condensation of 7-oxo-6-(1-hydroxyethyl)-3-(diphenoxyphosphate)-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid p-nitrophenyl ester (I) with the bis(trimethylsilyl) derivative of 2-(iminomethylamino)ethanethiol (II) in the presence of base gives p-nitrophenyl ester of MK-0787, protected with a trimethylsilyl group (III), which is finally deprotected by hydrogenolysis.

CLIP

Image result for imipenem synthesis

Synthesis Path

References

  1. ^ U.S. Patent 4,194,047
  2. ^ Clissold, SP; Todd, PA; Campoli-Richards, DM (Mar 1987). “Imipenem/cilastatin. A review of its antibacterial activity, pharmacokinetic properties and therapeutic efficacy”. Drugs33 (3): 183–241. doi:10.2165/00003495-198733030-00001PMID 3552595.
  3. ^ Vardakas, KZ; Tansarli, GS; Rafailidis, PI; Falagas, ME (Dec 2012). “Carbapenems versus alternative antibiotics for the treatment of bacteraemia due to Enterobacteriaceae producing extended-spectrum β-lactamases: a systematic review and meta-analysis”. The Journal of Antimicrobial Chemotherapy67 (12): 2793–803. doi:10.1093/jac/dks301PMID 22915465.
  4. ^ Fischer, Janos; Ganellin, C. Robin (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 497. ISBN 9783527607495.
  5. ^ Kahan, FM; Kropp, H; Sundelof, JG; Birnbaum, J (Dec 1983). “Thienamycin: development of imipenen-cilastatin”. The Journal of Antimicrobial Chemotherapy. 12 Suppl D: 1–35. doi:10.1093/jac/12.suppl_d.1PMID 6365872.
  6. ^ Kesado, Tadataka; Hashizume, Terutaka; Asahi, Yoshinari (1980). “Antibacterial activities of a new stabilized thienamycin, N-formimidoyl thienamycin, in comparison with other antibiotics”Antimicrobial Agents and Chemotherapy17 (6): 912–7. doi:10.1128/aac.17.6.912PMC 283902PMID 6931548.
  7. ^ “Imipenem spectrum of bacterial susceptibility and Resistance” (PDF). Retrieved 4 May 2012.
  8. ^ “IMIPENEM/CILASTATIN”livertox.nih.gov. Retrieved 2019-03-08.
  9. ^ Cannon, Joan P.; Lee, Todd A.; Clark, Nina M.; Setlak, Paul; Grim, Shellee A. (2014-08-01). “The risk of seizures among the carbapenems: a meta-analysis”Journal of Antimicrobial Chemotherapy69 (8): 2043–2055. doi:10.1093/jac/dku111ISSN 0305-7453.

Further reading

External links

Imipenem
Imipenem.svg
Imipenem ball-and-stick.png
Clinical data
Trade names Primaxin
AHFS/Drugs.com International Drug Names
MedlinePlus a686013
Pregnancy
category
  • AU: B3
  • US: C (Risk not ruled out)
Routes of
administration
IMIV
ATC code
Legal status
Legal status
Pharmacokinetic data
Protein binding 20%
Metabolism Renal
Elimination half-life 38 minutes (children), 60 minutes (adults)
Excretion Urine (70%)
Identifiers
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.058.831 Edit this at Wikidata
Chemical and physical data
Formula C12H17N3O4S
Molar mass 299.347 g/mol g·mol−1
3D model (JSmol)
    • Synonyms:Imipemide
    • ATC:J01DH51
  • Use:carbapenem antibiotic
  • Chemical name:[5R-[5α,6α(R*)]]-6-(1-hydroxyethyl)-3-[[2-[(iminomethyl)amino]ethyl]thio]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
  • Formula:C12H17N3O4S
  • MW:299.35 g/mol
  • CAS-RN:64221-86-9
  • InChI Key:ZSKVGTPCRGIANV-ZXFLCMHBSA-N
  • 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
  • EINECS:264-734-5
  • LD50:1660 mg/kg (M, i.v.); >5 g/kg (M, p.o.);
    1972 mg/kg (R, i.v.); >5 g/kg (R, p.o.)

Derivatives, monohydrate

  • Formula:C12H17N3O4S • H2O
  • MW:317.37 g/mol
  • CAS-RN:74431-23-5
References
    • Leanza, W.J. et al.: J. Med. Chem. (JMCMAR) 22, 1435 (1979).
    • a Salzmann, T.L. et al.: J. Am. Chem. Soc. (JACSAT) 102, 6161-6163 (1980).
    •  Reider, P.J.; Grabowski, E.J.J.: Tetrahedron Lett. (TELEAY) 23, 2293-2296 (1982).
    •  Grabowski, E.J.J.: Chirality (CHRLEP) 17, 249-259 (2005).
    • US 4 194 047 (Merck & Co.; 18.3.1980; prior. 21.11.1975).
    • DOS 2 652 679 (Merck & Co.; appl. 19.11.1976; USA-prior. 21.11.1975).
    • b US 5 998 612 (Merck & Co.; 7.12.1999; appl. 12.6.1992; prior. 23.10.1981).
    • c US 4 981 992 (Takasago; 27.1.1998; appl. 13.5.1996; J-prior. 11.5.1995).
    •  US 5 204 460 (Takasago; 20.4.1993; appl. 8.11.1991; J-prior. 8.11.1990).
    •  US 5 204 462 (Takasago; 20.4.1993; appl. 8.11.1991; J-prior. 8.11.1990).
    •  US 5 712 388 (Takasago; 27.1.1998; appl. 13.5.1996; J-prior. 11.5.1995).
    •  US 5 081 239 (Takasago; 14.1.1992; appl. 29.11.1989; J-prior. 29.11.1988).
  • Acetoxylation of 2-azetidinones in 4-position:
    • Noyori, R. et al.: J. Am. Chem. Soc. (JACSAT) 111, 9134-9135 (1989).
    • Noyori, R. et al.: Angew. Chem. (ANCEAD) 114, 2108-2123 (2002).
    • US 5 288 862 (Takasago; 22.2.1994; appl. 16.4.1992; J-prior. 18.4.1991).
    • US 5 606 052 (Takasago; 25.2.1997; appl. 16.4.1992; J-prior. 18.4.1991).
  • Noyori-catalyst:
    • US 4 739 084 (Takasago; 19.4.1988; appl. 15.4.1987; J-prior. 13.5.1986).
  • d process of Nippon Soda (Nisso):
    • US 5 026 844 (Suntory & Nippon Soda; 25.6.1991; appl. 13.10.1989; J-prior. 19.10.1988).
    • US 5 792 861 (Tanabe Seiyaku & Nippon Soda; 11.8.1998; appl. 29.6.1994, 4.11.1996; J-prior. 30.6.1993).
    • US 5 808 055 (Suntory & Nippon Soda; 15.9.1998; appl. 30.3.1993, 5.7.1995; J-prior. 30.3.1993).
    • e US 4 791 198 (Kanegafuchi; 13.12.1988; appl. 1.7.1985, 6.1.1987; J-prior. 5.7.1984, 14.1.1986).
    •  US 4 861 877 (Kanegafuchi; 29.8.1989; appl. 1.7.1985, 6.1.1987; J-prior. 5.7.1984, 14.1.1985, 14.1.1986).
    •  US 5 061 817 (Kanegafuchi; 29.10.1991; appl. 1.7.1985, 6.1.1987, 31.5.1988; J-prior. 5.7.1984, 14.1.1986).
    •  US 4 914 200 (Kanegafuchi; 3.4.1990; appl. 28.4.1987, 14.2.1989; J-prior. 30.4.1986, 13.11.1986, 9.2.1987).
  • Enzymatic reduction of alkyl-2-(N-benzoylamino)methyl-3-oxobutyrates with bakers yeast:
    • US 5 463 047 (Ciba-Geigy; 31.10.1995; appl. 15.9.1994; CH-prior. 4.5.1987).
  • Further synthesis processes of Merck & Co. for thienamycin:
    • Johnston, D.B.R. et al.: J. Am. Chem. Soc. (JACSAT) 100, 313-315 (1978).
    • Mellilo, D.G. et al.: Tetrahedron Lett. (TELEAY) 21, 2783 (1980).
    • Melillo, D.G. et al.: J. Org. Chem. (JOCEAH) 51, 1498-1504 (1986).
    • Karady, S. et al.: J. Am. Chem. Soc. (JACSAT) 103, 6765-6767 (1981).
    • US 4 269 772 (Merck & Co.; 26.5.1981; appl. 14.1.1980).
    • US 4 282 148 (Merck & Co.; 4.8.1981; appl. 14.1.1980).
    • US 4 287 123 (Merck & Co.; 1.9.1981; appl. 14.1.1980).
    • US 4 290 947 (Merck & Co.; 22.9.1981; appl. 29.5.1980).
    • US 4 360 684 (Merck & Co.; 23.11.1982; appl. 8.4.1981).
    • US 4 206 219 (Merck & Co.; 3.6.1980; appl. 24.10.1978).
    • US 4 348 320 (Merck & Co.; 7.9.1982; appl. 20.8.1980; USA-prior. 19.11.1976).
    • US 4 460 507 (Merck & Co.; 17.7.1984; appl. 29.4.1982; USA-prior. 10.10.1980).
    • US 5 055 573 (Merck & Co.; 8.10.1991, appl. 24.8.1990; USA-prior. 19.11.1976).
    • US 5 037 974 (Merck & Co.; 6.8.1991; appl. 14.8.1990; prior. 23.5.1988, 10.4.1990).
  • Review of thienamycin syntheses:
    • Nicolaou, K.C.; Sorensen, E.J.: Classics in Total Synthesis, VCH 1996, Weinheim & New York, chapter 16, p. 249-263.
    • Berks, A.H.: Tetrahedron (TETRAB) 52, 331-375 (1996).
  • Alternative 2-azetidinone ring closure with chlorosulfonyl isocyanate:
    • US 4 350 631 (Merck & Co.; 21.9.1982; appl. 18.3.1981; prior. 18.12.1980).
  • Thienamycin (by fermentation of S. cattleya):
    • US 3 950 357 (Merck & Co.; 13.4.1976; appl. 25.11.1974).
    • DOS 2 552 638 (Merck & Co.; appl. 24.11.1975; USA-prior. 25.11.1974).
  • Combination with cilastatin:
    • EP 48 301 (Merck & Co.; appl. 24.9.1980).

/////////////Imipenem, イミペネム水和物  , MK-787,


1 Comment

  1. kim johnson says:

    Thanx for the useful and authentic information you have share with this article
    it will be surely beneficial for everyone.

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DR ANTHONY MELVIN CRASTO, Born in Mumbai in 1964 and graduated from Mumbai University, Completed his Ph.D from ICT, 1991,Matunga, Mumbai, India, in Organic Chemistry, The thesis topic was Synthesis of Novel Pyrethroid Analogues, Currently he is working with AFRICURE PHARMA as ADVISOR, earlier assignment was with GLENMARK LIFE SCIENCES LTD, as CONSUlTANT, Retired from GLENMARK in Jan2022 Research Centre as Principal Scientist, Process Research (bulk actives) at Mahape, Navi Mumbai, India. Total Industry exp 32 plus yrs, Prior to joining Glenmark, he has worked with major multinationals like Hoechst Marion Roussel, now Sanofi, Searle India Ltd, now RPG lifesciences, etc. He has worked with notable scientists like Dr K Nagarajan, Dr Ralph Stapel, Prof S Seshadri, etc, He did custom synthesis for major multinationals in his career like BASF, Novartis, Sanofi, etc., He has worked in Discovery, Natural products, Bulk drugs, Generics, Intermediates, Fine chemicals, Neutraceuticals, GMP, Scaleups, etc, he is now helping millions, has 9 million plus hits on Google on all Organic chemistry websites. His friends call him Open superstar worlddrugtracker. His New Drug Approvals, Green Chemistry International, All about drugs, Eurekamoments, Organic spectroscopy international, etc in organic chemistry are some most read blogs He has hands on experience in initiation and developing novel routes for drug molecules and implementation them on commercial scale over a 32 PLUS year tenure till date Feb 2023, Around 35 plus products in his career. He has good knowledge of IPM, GMP, Regulatory aspects, he has several International patents published worldwide . He has good proficiency in Technology transfer, Spectroscopy, Stereochemistry, Synthesis, Polymorphism etc., He suffered a paralytic stroke/ Acute Transverse mylitis in Dec 2007 and is 90 %Paralysed, He is bound to a wheelchair, this seems to have injected feul in him to help chemists all around the world, he is more active than before and is pushing boundaries, He has 100 million plus hits on Google, 2.5 lakh plus connections on all networking sites, 100 Lakh plus views on dozen plus blogs, 227 countries, 7 continents, He makes himself available to all, contact him on +91 9323115463, email amcrasto@gmail.com, Twitter, @amcrasto , He lives and will die for his family, 90% paralysis cannot kill his soul., Notably he has 38 lakh plus views on New Drug Approvals Blog in 227 countries......https://newdrugapprovals.wordpress.com/ , He appreciates the help he gets from one and all, Friends, Family, Glenmark, Readers, Wellwishers, Doctors, Drug authorities, His Contacts, Physiotherapist, etc He has total of 32 International and Indian awards

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