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Name	Meropenem	EINECS	641-424-1
CAS No.	96036-03-2	Density	1.42 g/cm³
PSA	135.48000	LogP	-0.04130
Solubility	N/A	Melting Point	N/A
Formula	C₁₇H₂₅N₃O₅S	Boiling Point	627.4 °C at 760 mmHg
Molecular Weight	383.469	Flash Point	333.2 °C
Transport Information	N/A	Appearance	white powder
Safety	26-37/39	Risk Codes	36/37/38
Molecular Structure		Hazard Symbols	Xi
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;	Article Data	28

Meropenem 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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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;

Yield

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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Yield

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

Conditions	Yield
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

Yield

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

Conditions	Yield
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

Yield

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

Conditions	Yield
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

Yield

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

Meropenem 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: Irritant Xi
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.

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