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Basic Information
CAS No.: 96036-03-2
Name: Meropenem
Molecular Structure:
Molecular Structure of 96036-03-2 (Meropenem)
Formula: C17H25N3O5S
Molecular Weight: 383.469
Synonyms: 1-Azabicyclo[3.2.0]hept-2-ene-2-carboxylicacid,3-[[(3S,5S)-5-[(dimethylamino)carbonyl]-3-pyrrolidinyl]thio]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-,(4R,5S,6S)-;1-Azabicyclo[3.2.0]hept-2-ene-2-carboxylicacid,3-[[5-[(dimethylamino)carbonyl]-3-pyrrolidinyl]thio]-6-(1-hydroxyethyl)-4-methyl-7-oxo-,[4R-[3(3S*,5S*),4a,5b,6b(R*)]]-;Antibiotic SM 7338;ICI 194660;Mepem;Meronem;Meropen;Merrem;Merrem IV;SM 7338;
EINECS: 641-424-1
Density: 1.42 g/cm3
Boiling Point: 627.4 °C at 760 mmHg
Flash Point: 333.2 °C
Appearance: white powder
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 26-37/39
PSA: 135.48000
LogP: -0.04130
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Synthetic route
96036-02-1

p-nitrobenzyl (4R,5S,6S)-3-<(3S,5S)-5-dimethylaminocarbonyl-1-(p-nitrobenzyloxycarbonyl)pyrrolidin-3-ylthio>-6-<(1R)-1-hydroxyethyl>-4-methyl-7-oxo-1-azabicyclo<3.2.0>hept-2-en-2-carboxylate

96036-03-2

meropenem

Conditions
ConditionsYield
With 2,6-dimethylpyridine; hydrogen In tetrahydrofuran; water at 40℃; under 13446.2 Torr; for 1.16667h; Pressure; Temperature; Reagent/catalyst;85%
With formaldehyd; sodium isooctanoate; 5%-palladium/activated carbon In water at 7℃; for 2.5h; Reagent/catalyst; Temperature;85.3%
With platinum on carbon; hydrogen; p-toluidine In tetrahydrofuran at 25℃; under 13501.4 Torr; for 0.683333h; Reagent/catalyst; Solvent; Sealed tube;84%

(1R,5R,6S)-6-[(1R)-1-hydroxymethyl]-2-diphenylphosphoryloxocarbapen-2-em-3-carboxylic acid p-nitrobenzyl ester

(2R,4S)-4-dimethylaminomercapto-2-formyl-1-p-nitrobenzyl carbonylpyrrolidine

96036-03-2

meropenem

Conditions
ConditionsYield
Stage #1: (1R,5R,6S)-6-[(1R)-1-hydroxymethyl]-2-diphenylphosphoryloxocarbapen-2-em-3-carboxylic acid p-nitrobenzyl ester; (2R,4S)-4-dimethylaminomercapto-2-formyl-1-p-nitrobenzyl carbonylpyrrolidine at -5℃;
Stage #2: With 5%-palladium/activated carbon; hydrogen at 25℃; Reagent/catalyst;		44%
141818-52-2

4-nitrobenzyl (4R,5S,6S)-3-[[(3S,5S)-5-(dimethylcarbamoyl)-3-pyrrolidinyl]thio]-6-[(1R)-1-hydroxy-ethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

96036-03-2

meropenem

Conditions
ConditionsYield
With 4-methyl-morpholine; hydrogen; acetic acid In water; ethyl acetate at 20 - 25℃; for 3h; pH=~ 7; Product distribution / selectivity; Aqueous buffer;

4-nitrobenzyl (4R,5R,6S)-3-[(diphenoxyphosphoryl)oxy]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

Conditions
ConditionsYield
Stage #1: 4-nitrobenzyl (4R,5R,6S)-3-[(diphenoxyphosphoryl)oxy]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate; (2S,4S)-1-p-nitrobenzyloxycarbonyl-2-dimethylaminocarbonyl-4-thiolpyrrolidine With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at -50 - 25℃; for 1h;
Stage #2: With 4-methyl-morpholine; hydrogen; acetic acid; 5%-palladium/activated carbon In water; ethyl acetate; N,N-dimethyl-formamide at 20 - 25℃; for 3h; pH=~ 7;

(5R,6S,8R,2'S,4'S)-p-nitrobenzyl-3-[4-(1-p-nitrobenzyloxycarbonyl-2-dimethylaminocarbonyl)pyrrolidinylthio]-4-methyl-6-(1-hydroxyethyl)-1-azabicyclo[3.2.0]-hept-2-en-7-oxo-2carboxylate

96036-03-2

meropenem

Conditions
ConditionsYield
With hydrogen; palladium 10% on activated carbon In tetrahydrofuran; water at 25 - 30℃; for 2 - 3h;
93711-81-0, 90776-59-3

(4-nitrophenyl)methyl (4R,5R,6S)-3-[(diphenoxyphosphinyl)oxy]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

96034-64-9

(2S,4S)-1-p-nitrobenzyloxycarbonyl-2-dimethylaminocarbonyl-4-thiolpyrrolidine

96036-03-2

meropenem

Conditions
ConditionsYield
Stage #1: (4-nitrophenyl)methyl (4R,5R,6S)-3-[(diphenoxyphosphinyl)oxy]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate; (2S,4S)-1-p-nitrobenzyloxycarbonyl-2-dimethylaminocarbonyl-4-thiolpyrrolidine With N-ethyl-N,N-diisopropylamine In 1-methyl-pyrrolidin-2-one; water at -20 - -5℃;
Stage #2: With 4-methyl-morpholine; hydrogenchloride; 5% Pd(II)/C(eggshell); hydrogen In 1-methyl-pyrrolidin-2-one; water at 25℃; pH=6.5 - 7;
Stage #1: (4-nitrophenyl)methyl (4R,5R,6S)-3-[(diphenoxyphosphinyl)oxy]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate; (2S,4S)-1-p-nitrobenzyloxycarbonyl-2-dimethylaminocarbonyl-4-thiolpyrrolidine With N-ethyl-N,N-diisopropylamine In 1-methyl-pyrrolidin-2-one at -20 - -5℃;
Stage #2: With hydrogen; 5%-palladium/activated carbon In 1-methyl-pyrrolidin-2-one at 25℃; pH=6.5 - 7; N-methylmorpholine - hydrochloric acid - buffer;
Stage #1: (4-nitrophenyl)methyl (4R,5R,6S)-3-[(diphenoxyphosphinyl)oxy]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate; (2S,4S)-1-p-nitrobenzyloxycarbonyl-2-dimethylaminocarbonyl-4-thiolpyrrolidine With N-ethyl-N,N-diisopropylamine In N,N-dimethyl acetamide at 0 - 5℃; for 5h;
Stage #2: With potassium dihydrogenphosphate; zinc In water; ethyl acetate at 25 - 35℃; for 1h;
Stage #1: (4-nitrophenyl)methyl (4R,5R,6S)-3-[(diphenoxyphosphinyl)oxy]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate; (2S,4S)-1-p-nitrobenzyloxycarbonyl-2-dimethylaminocarbonyl-4-thiolpyrrolidine With N-ethyl-N,N-diisopropylamine In ISOPROPYLAMIDE at 0 - 5℃; for 5h;
Stage #2: With hydrogenchloride In water; ethyl acetate
Stage #3: With potassium dihydrogenphosphate In water; ethyl acetate at 25 - 35℃; for 1h;

C19H34N2O4SSi

96036-03-2

meropenem

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: dmap / dichloromethane / 3 h / 20 - 30 °C
2.1: dichloromethane / 3 h / 20 - 45 °C / Reflux
3.1: triethylamine; 4-toluenesulfonyl azide / dichloromethane / 2 h / 20 - 30 °C
4.1: hydrogenchloride; methanol / dichloromethane; water / 3 h / 20 - 30 °C
5.1: dichloromethane; Isopropyl acetate / 25 - 30 °C
6.1: zinc dibromide; rhodium (II) octanoate dimer / dichloromethane / 40 °C / Reflux
7.1: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / -10 - 0 °C
8.1: N-ethyl-N,N-diisopropylamine / 1-methyl-pyrrolidin-2-one / -20 - -5 °C
8.2: 25 °C / pH 6.5 - 7 / N-methylmorpholine - hydrochloric acid - buffer
View Scheme

C17H29N3O3Si

96036-03-2

meropenem

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: dichloromethane / 3 h / 20 - 45 °C / Reflux
2.1: triethylamine; 4-toluenesulfonyl azide / dichloromethane / 2 h / 20 - 30 °C
3.1: hydrogenchloride; methanol / dichloromethane; water / 3 h / 20 - 30 °C
4.1: dichloromethane; Isopropyl acetate / 25 - 30 °C
5.1: zinc dibromide; rhodium (II) octanoate dimer / dichloromethane / 40 °C / Reflux
6.1: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / -10 - 0 °C
7.1: N-ethyl-N,N-diisopropylamine / 1-methyl-pyrrolidin-2-one / -20 - -5 °C
7.2: 25 °C / pH 6.5 - 7 / N-methylmorpholine - hydrochloric acid - buffer
View Scheme

C23H34N2O7Si

96036-03-2

meropenem

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: triethylamine; 4-toluenesulfonyl azide / dichloromethane / 2 h / 20 - 30 °C
2.1: hydrogenchloride; methanol / dichloromethane; water / 3 h / 20 - 30 °C
3.1: dichloromethane; Isopropyl acetate / 25 - 30 °C
4.1: zinc dibromide; rhodium (II) octanoate dimer / dichloromethane / 40 °C / Reflux
5.1: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / -10 - 0 °C
6.1: N-ethyl-N,N-diisopropylamine / 1-methyl-pyrrolidin-2-one / -20 - -5 °C
6.2: 25 °C / pH 6.5 - 7 / N-methylmorpholine - hydrochloric acid - buffer
View Scheme

C23H32N4O7Si

96036-03-2

meropenem

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: hydrogenchloride; methanol / dichloromethane; water / 3 h / 20 - 30 °C
2.1: dichloromethane; Isopropyl acetate / 25 - 30 °C
3.1: zinc dibromide; rhodium (II) octanoate dimer / dichloromethane / 40 °C / Reflux
4.1: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / -10 - 0 °C
5.1: N-ethyl-N,N-diisopropylamine / 1-methyl-pyrrolidin-2-one / -20 - -5 °C
5.2: 25 °C / pH 6.5 - 7 / N-methylmorpholine - hydrochloric acid - buffer
View Scheme
Raw Materials
90822-24-5
96034-57-0
96036-02-1
96034-64-9
51-35-4
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Specification

1. Introduction of Meropenem
Meropenem is one kind of white or almost white crystalline powder. The IUPAC name of this chemical is (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. Besides, Meropenem belongs to Active Pharmaceutical Ingredients;Antibacterial;Cnbio;pharmaceutical intermediates. In addition, Meropenem Classification Code is Anti-Bacterial Agents; Anti-Infective Agents; Drug / Therapeutic Agent; Reproductive Effect. What's more, Meropenem is soluble in 5% monobasic potassium phosphate solution, sparingly soluble in water, very slightly soluble in hydrated ethanol.

Meropenem (CAS NO.96036-03-2) was originally developed by Sumitomo Pharmaceuticals. It is marketed outside Japan by AstraZeneca with the brand names Merrem and Meronem . Other brand names include Mepem (Taiwan) , Meropen (Japan, Korea) and Neopenem (India) . It gained FDA approval in July 1996. It penetrates well into many tissues and body fluids including the cerebrospinal fluid, bile, heart valves, lung, and peritoneal fluid.

2. Properties of Meropenem
Physical properties about Meropenem are:
(1)Index of Refraction: 1.639; (2)Surface Tension: 68.4 dyne/cm; (3)Density: 1.42 g/cm3; (4)Flash Point: 333.2 °C; (5)Enthalpy of Vaporization: 106.42 kJ/mol; (6)Boiling Point: 627.4 °C at 760 mmHg; (7)Vapour Pressure: 2.27E-18 mmHg at 25 °C; (8)log Kow = -1.25 (est); (9)XLogP3-AA: -2.4; (10)H-Bond Donor: 3; (11)H-Bond Acceptor: 7.

3. Structure Descriptors of Meropenem
(1)InChI: InChI=1S/C17H25N3O5S/c1-7-12-11(8(2)21)16(23)20(12)13(17(24)25)14(7)26-9-5-10(18-6-9)15(22)19(3)4/h7-12,18,21H,5-6H2,1-4H3,(H,24,25)/t7-,8-,9+,10+,11-,12-/m1/s1
(2)InChIKey: DMJNNHOOLUXYBV-PQTSNVLCSA-N
(3)Canonical SMILES : CC1C2C(C(=O)N2C(=C1SC3CC(NC3)C(=O)N(C)C)C(=O)O)C(C)O
(4)Isomeric SMILES: C[C@@H]1[C@@H]2[C@H](C(=O)N2C(=C1S[C@H]3C[C@H](NC3)C(=O)N(C)C)C(=O)O)[C@@H](C)O
(5)Smiles: C[C@@H]1[C@@H]2[C@H](C(=O)N2C(=C1S[C@H]3C[C@H](NC3)C(=O)N(C)C)C(=O)O)[C@@H](C)O

4. Toxicity of Meropenem

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LDLo intravenous 2gm/kg (2000mg/kg) LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD		 Chemotherapy Vol. 40(Suppl,
mouse LD50 intravenous 2650mg/kg (2650mg/kg) BEHAVIORAL: ATAXIA

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD		 Chemotherapy Vol. 40(Suppl,
mouse LD50 oral > 5gm/kg (5000mg/kg)   Chemotherapy Vol. 40(Suppl,
mouse LD50 subcutaneous > 5gm/kg (5000mg/kg)   Chemotherapy Vol. 40(Suppl,
rat LD50 intravenous 2850mg/kg (2850mg/kg) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE

LUNGS, THORAX, OR RESPIRATION: DYSPNEA		 Chemotherapy Vol. 40(Suppl,
rat LD50 oral > 5gm/kg (5000mg/kg)   Chemotherapy Vol. 40(Suppl,
rat LD50 subcutaneous > 5gm/kg (5000mg/kg)   Chemotherapy Vol. 40(Suppl,

5. Safety Information of Meropenem
Hazard Codes: IrritantXi
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-37/39 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S37/39:Wear suitable gloves and eye/face protection.

6. Uses of Meropenem
Meropenem (CAS NO.96036-03-2) is an ultra-broad spectrum injectable antibiotic used to treat a wide variety of infections, including meningitis and pneumonia. It is a beta-lactam and belongs to the subgroup of carbapenem, similar to imipenem and ertapenem.