Meropenem

Names

[ Name ]:
Meropenem

[Synonym ]:
SM 7338
MEROPENEM, ANTIBIOTIC FOR CULTURE MEDIA USE ONLY
(1'R,3'S,5'S,4R,5S,6S)-3-(5-DIMETHYLCARBAMOYL-PYRROLIDIN-3-YLSULFANYL)-6-(1-HYDROXY-ETHYL)-4-METHYL-7-OXO-1-AZA-BICYCLO[3.2.0]HEPT-2-ENE-2-CARBOXYLIC ACID
[4R-[3(3S*,5S*),4a,5b,6b(R*)]]-3-[[5-[(Dimethylamino)carbonyl]-3-pyrrolidinyl]thio]-6-(1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic Acid
(1R,5S,6S)-2-[(3S,5S)-5-(Dimethylaminocarbonyl)pyrrolidin-3-ylthio]-6-[(R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylic Acid
MEROPENEM (PATENTED)
Merrem
(4R,5S,6S)-3-{[(3S,5S)-5-(dimethylcarbamoyl)pyrrolidin-3-yl]sulfanyl}-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
MEROPENAM
(4R-(3(S*,5S*),4-a,5b,6b(R*)))-3-((5-((Dimethylamino)carbonyl)-3-pyrrolidinyl)thio)-6-(1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
MeropeneM API
(4R,5S,6S)-3-{[(3S,5S)-5-(Dimethylcarbamoyl)-3-pyrrolidinyl]sulfanyl}-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
Meronem
MEROPENEM,USP
1-Azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid, 3-[[(3S,5S)-5-[(dimethylamino)carbonyl]-3-pyrrolidinyl]thio]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-, (4R,5S,6S)-
MEROPENEM FOR INJECTION
(4R,5S,6S)-3-[[(3S,5S)-5-[(dimethylamino)carbonyl]-3-pyrrolidinyl]thio]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicycl 0[3.2.0]hept-2-ene-2-carboxylic acid
MeropeneM Crude
MEROPENEM, 1 G
Meropen
Meropenem
1-Azabicyclo(3.2.0)hept-2-ene-2-carboxylic acid, 3-(((3S,5S)-5-((dimethylamino)carbonyl)-3-pyrrolidinyl)thio)-6-((1R)-1-hydroxyethyl)-4-methyl-7-oxo-, (4R,5S,6S)-
MFCD00864966

Biological Activity

[Description]:

Meropenem is a carbapenem antibiotic, which displaying a broad spectrum of antibacterial activity.Target: AntibacterialMeropenem, a new parenteral carbapenem demonstrated increased activity as compared to imipenem against 336 strains of Neisseria gonorrhoeae, 119 strains of Haemophilus influenzae, and 110 strains of H. Ceftriaxone and ciprofloxacin demonstrated activity superior to that of both carbapenems while the activity of ceftazidime was similar to that of meropenem [1]. Meropenem, like imipenem and various experimental penems, may overcome the resistance problems presented by Class I beta-lactamases [2]. MEROPENEM was rapidly penetrated to the pleural effusion and was retained for a more prolonged time in the pleural effusion than in the blood of patients with accumulated pleural effusion, and it suggested the usefulness of MEROPENEM in antibacterial therapy for patients with pleurisy causing accumulation of pleural effusion [3].Clinical indications: Appendicitis; Bacterial infection; Bacterial meningitis; Bacterial pneumonia; Bacterial respiratory tract infection; Bacterial skin infection; Bacterial urinary tract infection; Bacteroides fragilis infection; Bacteroides infection; Bacteroides thetaiotaomicron infection; Complicated skin and skin structure infectionFDA Approved Date: July 1996Toxicity: In mice and rats, large intravenous doses of meropenem (2200-4000 mg/kg) have been associated with ataxia, dyspnea, convulsions, and mortalities.

[Related Catalog]:

Signaling Pathways >> Anti-infection >> Bacterial

Natural Products >> Alkaloid

Research Areas >> Infection

[References]

[1]. Slaney, L., et al., In-vitro activity of meropenem against Neisseria gonorrhoeae, Haemophilus influenzae and H. ducreyi from Canada and Kenya. J Antimicrob Chemother, 1989. 24 Suppl A: p. 183-6.

[2]. Yang, Y.J. and D.M. Livermore, Interactions of meropenem with class I chromosomal beta-lactamases. J Antimicrob Chemother, 1989. 24 Suppl A: p. 207-17.

[3]. Makino, J., et al., [Pharmacokinetic study of penetration of meropenem into pleural effusion in patients with pleurisy]. Jpn J Antibiot, 2002. 55(1): p. 77-88.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Boiling Point ]:
627.4±55.0 °C at 760 mmHg

[ Molecular Formula ]:
C₁₇H₂₅N₃O₅S

[ Molecular Weight ]:
383.462

[ Flash Point ]:
333.2±31.5 °C

[ Exact Mass ]:
383.151489

[ PSA ]:
135.48000

[ LogP ]:
-3.13

[ Vapour Pressure ]:
0.0±4.2 mmHg at 25°C

[ Index of Refraction ]:
1.639

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: CL5446509

CHEMICAL NAME :: 1-Azabicyclo(3.2.0)hept-2-ene-2-carboxylic acid, 3-((5-((dimethylamino)carbonyl)- 3-pyrrolidinyl)thio)-6-(1-hydroxyethyl)-4-methyl-7-ox o-, (4R-(3(S*,5S*),4-alpha,5- beta,6-beta(R*)))-

CAS REGISTRY NUMBER :: 96036-03-2

LAST UPDATED :: 199612

DATA ITEMS CITED :: 10

MOLECULAR FORMULA :: C17-H25-N3-O5-S

MOLECULAR WEIGHT :: 383.51

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >5 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: NKRZAZ Chemotherapy (Tokyo). (Nippon Kagaku Ryoho Gakkai, 2-20-8 Kamiosaki, Shinagawa-Ku, Tokyo 141, Japan) V.1- 1953- Volume(issue)/page/year: 40(Suppl 1),182,1992

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >5 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: NKRZAZ Chemotherapy (Tokyo). (Nippon Kagaku Ryoho Gakkai, 2-20-8 Kamiosaki, Shinagawa-Ku, Tokyo 141, Japan) V.1- 1953- Volume(issue)/page/year: 40(Suppl 1),182,1992

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 2850 mg/kg

TOXIC EFFECTS :: Peripheral Nerve and Sensation - spastic paralysis with or without sensory change Behavioral - changes in motor activity (specific assay) Lungs, Thorax, or Respiration - dyspnea

REFERENCE :: NKRZAZ Chemotherapy (Tokyo). (Nippon Kagaku Ryoho Gakkai, 2-20-8 Kamiosaki, Shinagawa-Ku, Tokyo 141, Japan) V.1- 1953- Volume(issue)/page/year: 40(Suppl 1),182,1992

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >5 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: NKRZAZ Chemotherapy (Tokyo). (Nippon Kagaku Ryoho Gakkai, 2-20-8 Kamiosaki, Shinagawa-Ku, Tokyo 141, Japan) V.1- 1953- Volume(issue)/page/year: 40(Suppl 1),182,1992

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >5 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: NKRZAZ Chemotherapy (Tokyo). (Nippon Kagaku Ryoho Gakkai, 2-20-8 Kamiosaki, Shinagawa-Ku, Tokyo 141, Japan) V.1- 1953- Volume(issue)/page/year: 40(Suppl 1),182,1992

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 2650 mg/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold Behavioral - changes in motor activity (specific assay) Behavioral - ataxia

REFERENCE :: NKRZAZ Chemotherapy (Tokyo). (Nippon Kagaku Ryoho Gakkai, 2-20-8 Kamiosaki, Shinagawa-Ku, Tokyo 141, Japan) V.1- 1953- Volume(issue)/page/year: 40(Suppl 1),182,1992

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Parenteral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >12 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JANTAJ Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo, 141, Japan) V.2-5, 1948-52; V.21- 1968- Volume(issue)/page/year: 45,1983,1992

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 2 gm/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - acute pulmonary edema Nutritional and Gross Metabolic - body temperature decrease

REFERENCE :: NKRZAZ Chemotherapy (Tokyo). (Nippon Kagaku Ryoho Gakkai, 2-20-8 Kamiosaki, Shinagawa-Ku, Tokyo 141, Japan) V.1- 1953- Volume(issue)/page/year: 40(Suppl 1),182,1992 ** OTHER MULTIPLE DOSE TOXICITY DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 10920 mg/kg/13W-C

TOXIC EFFECTS :: Kidney, Ureter, Bladder - other changes in urine composition Endocrine - changes in spleen weight Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - other transferases

REFERENCE :: NKRZAZ Chemotherapy (Tokyo). (Nippon Kagaku Ryoho Gakkai, 2-20-8 Kamiosaki, Shinagawa-Ku, Tokyo 141, Japan) V.1- 1953- Volume(issue)/page/year: 40(Suppl 1),192,1992 ** REPRODUCTIVE DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

DOSE :: 9 gm/kg

SEX/DURATION :: female 6-17 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain)

REFERENCE :: NKRZAZ Chemotherapy (Tokyo). (Nippon Kagaku Ryoho Gakkai, 2-20-8 Kamiosaki, Shinagawa-Ku, Tokyo 141, Japan) V.1- 1953- Volume(issue)/page/year: 40(Suppl 1),238,1992

Safety Information

[ Hazard Codes ]:
Xi: Irritant;

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
26-37/39

[ HS Code ]:
2933990090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2933990090

[ Summary ]:
2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Related Compounds

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