Conditions | Yield |
---|---|
With (S)-Phenylglycine methyl ester In ethylene glycol at 20℃; for 48h; Enzymatic reaction; | 96.7% |
6-Aminopenicillanic Acid
(R)-phenylglycine amide
A
(R)-phenylglycine
B
ampicillin
Conditions | Yield |
---|---|
With A. faecalis; immobilised penicillin acylase (EC 3.5.1.11) In water; acetonitrile at 0℃; Product distribution; Kinetics; Further Variations:; Solvents; reusing run; Enzymatic reaction; | A n/a B 86% |
Conditions | Yield |
---|---|
With phosphate buffer; Eupergit C-immobilized penicillin acylase (30 U/mg); sodium sulfate at 20℃; pH=6.5; Product distribution; Kinetics; Further Variations:; Reagents; water content; solid phase reaction; | 70% |
at 30℃; for 3h; Pseudomonas melanogenum KY 3987 and KY 8540; Yield given; | |
With penicillin acylasefrom Escherichia coli; water | |
With βF24G mutant of penicillin G acylase from Alcaligenes faecalis, immobilized onto an epoxy carrier LH-EP In glycerol at 20℃; pH=5.8; Concentration; pH-value; Temperature; Green chemistry; Enzymatic reaction; |
Conditions | Yield |
---|---|
(i) HN(SiMe3)2, CHCl3, (ii) /BRN= 4946351/, DCC, CH2Cl2, (iii) hexamethylentetramine; Multistep reaction; |
6-Aminopenicillanic Acid
N-carboxy-(R)-phenylglycine anhydride
ampicillin
Conditions | Yield |
---|---|
With sodium hydroxide |
6β-((R)-2-benzylideneamino-2-phenyl-acetylamino)-penicillanic acid; 1,1,3,3-tetramethyl-butylamine salt
ampicillin
Conditions | Yield |
---|---|
With 4-methyl-2-pentanone In water |
6-Aminopenicillanic Acid
D-phenylglycine methyl ester hydrochloride
ampicillin
Conditions | Yield |
---|---|
With potassium phosphate; Pseudomonas melanogenum KY 8541 at 30℃; pH=6.5; |
pivampicillin
ampicillin
Conditions | Yield |
---|---|
With phosphate buffer; sodium chloride In water at 37℃; half-life value, pH 7.4, other ampicillin esters; |
ampicillin
Conditions | Yield |
---|---|
With phosphate buffer; sodium chloride In water at 37℃; half-life value, pH 7.4, other ampicillin esters; |
ampicillin
Conditions | Yield |
---|---|
With phosphate buffer; sodium chloride In water at 37℃; half-life value, pH 7.4, other ampicillin esters; |
ampicillin
Conditions | Yield |
---|---|
With phosphate buffer; sodium chloride In water at 37℃; half-life value, pH 7.4, other ampicillin esters; |
ampicillin
Conditions | Yield |
---|---|
With phosphate buffer; sodium chloride In water at 37℃; Rate constant; half-life value, pH 7.4, various pH, other ampicillin esters; |
ampicillin
Conditions | Yield |
---|---|
With phosphate buffer; sodium chloride In water at 37℃; half-life value, pH 7.4, other ampicillin esters; |
(2S,5R,6R)-6-((R)-2-Amino-2-phenyl-acetylamino)-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 3-cyclohexylidene-2,5-dioxo-pyrrolidin-1-ylmethyl ester
ampicillin
Conditions | Yield |
---|---|
With phosphate buffer; sodium chloride In water at 37℃; half-life value, pH 7.4, other ampicillin esters; |
ampicillin
Conditions | Yield |
---|---|
With phosphate buffer; sodium chloride In water at 37℃; half-life value, pH 7.4, other ampicillin esters; |
bacampicillin Hydrochloride
A
ampicillin
Conditions | Yield |
---|---|
With sodium hydroxide; Tween 80 solution; potassium chloride In water at 35℃; Rate constant; pH 6.00, μ = 0.5; degradation in suspension; |
nicotinamide
6-aminopenicillanic acid
diethylamine
B
ampicillin
Conditions | Yield |
---|---|
In dichloromethane; water |
6-Aminopenicillanic Acid
DL-2-phenylglycine methyl ester hydrochloride
A
ampicillin
B
ampicillin
Conditions | Yield |
---|---|
With α-amino ester hydrolase from Xanthomonas campestris pv. campestris (ATCC 33913) at 25℃; pH=6.2; aq. phosphate buffer; Enzymatic reaction; optical yield given as %de; enantioselective reaction; |
6-Aminopenicillanic Acid
D-phenylglycine methyl ester hydrochloride
A
(R)-phenylglycine
B
ampicillin
Conditions | Yield |
---|---|
With α-amino ester hydrolase from Xanthomonas campestris pv. campestris (ATCC 33913) at 25℃; pH=6.2; aq. phosphate buffer; Enzymatic reaction; |
6-Aminopenicillanic Acid
(R)-phenylglycine amide
ampicillin
Conditions | Yield |
---|---|
With penicillin acylasefrom Escherichia coli; water |
Conditions | Yield |
---|---|
With wild-type cocaine esterase In aq. phosphate buffer at 20℃; Enzymatic reaction; |
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 1.5h; | 100% |
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran; 1,4-dioxane; water; acetone at 5 - 15℃; for 3h; Time; Temperature; Concentration; | 99.5% |
With sodium hydroxide In water at 10℃; for 0.5h; pH=7-7.5; | 88% |
With triethylamine In tetrahydrofuran; 1,4-dioxane; water; acetone for 2.5h; |
ampicillin
1-chlorocarbonyl-2-oxo-3-methylcarbonyl-imidazolidine
penicillin G
Conditions | Yield |
---|---|
With triethylamine In methanol; aqueous tetrahydrofurane; water; ethyl acetate | 95% |
With triethylamine In methanol; aqueous tetrahydrofurane; water; ethyl acetate | 95% |
With triethylamine In methanol; aqueous tetrahydrofurane; water; ethyl acetate | 95% |
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 1.5h; | 95% |
ampicillin
1-ethyl-3-methyl-1H-imidazol-3-ium chloride
(2S,5R,6R)-6-(R-2-amino-2-phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylate 1-ethyl-3-methylimidazolium
Conditions | Yield |
---|---|
Stage #1: 1-ethyl-3-methyl-1H-imidazol-3-ium chloride With Amberlite IRA-400-OH In methanol Stage #2: ampicillin With ammonium In methanol at 20℃; for 1h; | 94.6% |
ampicillin
4-ethyl-2,3-dioxopiperazine-1-carbonyl chloride
piperacillin
Conditions | Yield |
---|---|
With calcium carbonate In dichloromethane; water; ethyl acetate at 30 - 35℃; for 0.833333h; | 93.7% |
With sodium acetate; 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane; water; ethyl acetate at 5 - 10℃; for 0.916667h; pH=6.5 - 7.5; Temperature; Reagent/catalyst; Green chemistry; | 92.8% |
With triethylamine In water; ethyl acetate at 15 - 20℃; for 1h; pH=7.1; | 123.5 g |
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 1.5h; | 91% |
ampicillin
3-chlorocarbonyl-1-methanesulfonyl-2-imidazolidinone
mezlocillin
Conditions | Yield |
---|---|
With sodium hydroxide In water for 3h; | 90.5% |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide a) RT, 2 h, b) 0 deg C, 4 h; | 90% |
Conditions | Yield |
---|---|
In methanol for 5h; Reflux; | 87% |
ampicillin
3-(2-hydroxyethyl)-1-methyl-1H-imidazol-3-ium 6-(2-amino-2-phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
Conditions | Yield |
---|---|
Stage #1: 3-(2-hydroxyethyl)-1-methyl-1H-imidazol-3-ium chloride With Amberlite IRA-400(OH) In methanol Stage #2: ampicillin With ammonium In methanol at 20℃; for 1h; | 86.8% |
Conditions | Yield |
---|---|
With hydrogenchloride; triethylamine In tetrahydrofuran; aqueous tetrahydrofurane | 85% |
Conditions | Yield |
---|---|
In methanol Reflux; | 85% |
ampicillin
3-methylbenzene-1,2-diol
6-[2-(5-methyl-3,4-dioxocyclohexa-1,5-dienylamino)-2-phenylacetylamino]penicillanic acid
Conditions | Yield |
---|---|
With oxygen at 20℃; for 1.5h; pH=5.6; aq. acetate buffer; Enzymatic reaction; | 83% |
Conditions | Yield |
---|---|
Stage #1: sebacoyl chloride; ampicillin With pyridine In N,N-dimethyl-formamide at 0℃; for 2.08333h; Stage #2: With hydrogenchloride In water; N,N-dimethyl-formamide pH=2; | 82% |
Conditions | Yield |
---|---|
In methanol Reflux; | 82% |
trihexyl(tetradecyl)phosphonium chloride
ampicillin
(2S,5R,6R)-6-(R-2-amino-2-phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylate trihexyltetradecylphosphonium
Conditions | Yield |
---|---|
Stage #1: trihexyl(tetradecyl)phosphonium chloride With Amberlite IRA-400-OH In methanol Stage #2: ampicillin With ammonium In methanol at 20℃; for 1h; | 80% |
ampicillin
Conditions | Yield |
---|---|
With 4-nitro-phenol In tetrahydrofuran; water at 20℃; for 1h; | 78% |
With 4-nitro-phenol; triethylamine In tetrahydrofuran; water at 20℃; for 2h; | 1.04 g |
2-(4-methoxybenzyloxycarbonyloxyimino)-2-phenylacetonitrile
ampicillin
(2S,5R,6R)-6-[(R)-2-(4-Methoxy-benzyloxycarbonylamino)-2-phenyl-acetylamino]-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In 1,4-dioxane for 6h; pH=7.8; | 76.5% |
Conditions | Yield |
---|---|
Stage #1: cetylpyridinium chloride With Amberlite IRA-400-OH In methanol Stage #2: ampicillin With ammonium In methanol at 20℃; for 1h; | 76.4% |
tetraethylammonium bromide
ampicillin
(2S,5R,6R)-6-(R-2-amino-2-phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylate tetraethylammonium
Conditions | Yield |
---|---|
Stage #1: tetraethylammonium bromide With Amberlite IRA-400-OH In methanol Stage #2: ampicillin With ammonium In methanol at 20℃; for 1h; | 76% |
Conditions | Yield |
---|---|
With TEA In tetrahydrofuran; water for 2h; Ambient temperature; | 75% |
Conditions | Yield |
---|---|
Stage #1: ampicillin With DIEA In N,N-dimethyl-formamide at 0℃; Stage #2: C20H15N5O6 In N,N-dimethyl-formamide at 20℃; for 12h; | 75% |
ampicillin
1-benzyl N-carbobenzoxy-L-glutamate
Conditions | Yield |
---|---|
With chloroformic acid ethyl ester; triethylamine In dichloromethane 1.) -10 deg C, 0.5 h, 2.) room temperature, 1 h; | 71% |
choline chloride
ampicillin
(2-hydroxyethyl)trimethylammonium 6-(2-amino-2-phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
Conditions | Yield |
---|---|
Stage #1: choline chloride With Amberlite IRA-400-OH In methanol Stage #2: ampicillin With ammonium In methanol at 20℃; for 1h; | 70.7% |
ampicillin
Conditions | Yield |
---|---|
Stage #1: N6-[N2',N6'-bis(2,3-diacetoxybenzoyl)-L-lysyl]-N2-(2,3-diacetoxybenzoyl)-L-lysine With 4-methyl-morpholine; isobutyl chloroformate In tetrahydrofuran at -10℃; for 0.75h; Stage #2: ampicillin With triethylamine In tetrahydrofuran at -10 - 20℃; for 2h; | 70% |
ampicillin
N2-[N2',N6'-bis(2,3-diacetoxybenzoyl)-L-lysyl]-N6-(2,3-diacetoxybenzoyl)-L-lysine
Conditions | Yield |
---|---|
Stage #1: N2-[N2',N6'-bis(2,3-diacetoxybenzoyl)-L-lysyl]-N6-(2,3-diacetoxybenzoyl)-L-lysine With 4-methyl-morpholine; isobutyl chloroformate In tetrahydrofuran at -10℃; for 0.75h; Stage #2: ampicillin With triethylamine In tetrahydrofuran at -10 - 20℃; for 2h; | 70% |
Molecular Formula: C16H19N3O4S
Molecular Weight: 349.40
EINECS:200-709-7
Index of Refraction: 1.675
Density: 1.45 g/cm3
Flash Point: 367.4 °C
Enthalpy of Vaporization: 105.36 kJ/mol
Boiling Point: 683.9 °C at 760 mmHg
Vapour Pressure: 1.21E-19 mmHg at 25 °C
Melting point: 198-200 °C (dec.)(lit.)
Storage tempreture: 2-8 °C
Solubility: NH4OH 1 M: 50 mg/mL, clear, colorless
Appearance: Crystalline solid
Structure of Ampicillin (CAS NO.69-53-4):
IUPAC Name: (2S,5R,6R)-6-[[(2R)-2-Amino-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Canonical SMILES: CC1(C(N2C(S1)C(C2=O)NC(=O)C(C3=CC=CC=C3)N)C(=O)O)C
Isomeric SMILES: CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)[C@@H](C3=CC=CC=C3)N)C(=O)O)C
InChI: InChI=1S/C16H19N3O4S/c1-16(2)11(15(22)23)19-13(21)10(14(19)24-16)18-12(20)9(17)8-6-4-3-5-7-8/h3-7,9-11,14H,17H2,1-2H3,(H,18,20)(H,22,23)/t9-,10-,11+,14-/m1/s1
InChIKey: AVKUERGKIZMTKX-NJBDSQKTSA-N
Product Category of Ampicillin (CAS NO.69-53-4): Chiral Reagents;Intermediates & Fine Chemicals;Isotope Labeled Compounds;Pharmaceuticals;veterinary medicine,soluble powder
Ampicillin (CAS NO.69-53-4) can be semi-synthetic broad-spectrum penicillin for the treatment of sensitive enterococci, Shigella, Salmonella typhi, Escherichia coli, Listeria monocytogenes, gas bacillus, influenza bacillus, and Proteus mirabilis, etc..
First D (-) - phenylglycine side chain carboxylic acid with the chlorinating agent PCI5. Made chloride, and then carried out with the 6-APA derived from condensation reaction. In the reaction tank by adding acetone and water, and cooling to -5 - 10 °C when you join the 6-APA, coupled with Gly-chloride hydrochloride, the reaction with 10% sodium hydroxide, after 0.5h adjust pH to 3.5. Reactants extraction with toluene. Water layer, with 10% of the adjusted pH value of ammonia is about 3.0. Decoloration with activated carbon and filtering. Filtrate then adjusted to pH 4.8 ammonia. Put it aside, then filtered, washed with acetone at 40 °C below the vacuum drying too products.
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
cat | LDLo | intravenous | > 100mg/kg (100mg/kg) | British Medical Journal. Vol. 2, Pg. 197, 1961. | |
guinea pig | LD50 | unreported | 7500ug/kg (7.5mg/kg) | Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 42(9), Pg. 10, 1977. | |
man | TDLo | oral | 400mg/kg/4W-I (400mg/kg) | BLOOD: AGRANULOCYTOSIS BLOOD: OTHER CHANGES | Annals of Internal Medicine. Vol. 69, Pg. 91, 1968. |
mouse | LD50 | intracrebral | 380mg/kg (380mg/kg) | BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS" BEHAVIORAL: EXCITEMENT MUSCULOSKELETAL: CHANGES IN TEETH AND SUPPORTING STRUCTURES | Chemotherapy Vol. 26, Pg. 196, 1980. |
mouse | LD50 | intraperitoneal | 3250mg/kg (3250mg/kg) | BRAIN AND COVERINGS: RECORDINGS FROM SPECIFIC AREAS OF CNS BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) | Eksperimental'naya i Klinicheskaya Farmakoterapiya. Vol. 9, Pg. 83, 1980. |
mouse | LD50 | intravenous | 4600mg/kg (4600mg/kg) | Yakugaku Zasshi. Journal of Pharmacy. Vol. 97, Pg. 987, 1977. | |
mouse | LD50 | oral | > 5gm/kg (5000mg/kg) | Drugs in Japan Vol. 6, Pg. 57, 1982. | |
mouse | LD50 | parenteral | > 3gm/kg (3000mg/kg) | Drugs in Japan Vol. -, Pg. 114, 1995. | |
mouse | LD50 | unreported | 28gm/kg (28000mg/kg) | Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 42(9), Pg. 10, 1977. | |
mouse | LDLo | subcutaneous | > 5gm/kg (5000mg/kg) | British Medical Journal. Vol. 2, Pg. 197, 1961. | |
rat | LD50 | intraperitoneal | 4500mg/kg (4500mg/kg) | Toxicology and Applied Pharmacology. Vol. 18, Pg. 185, 1971. | |
rat | LD50 | intravenous | 6200mg/kg (6200mg/kg) | Drugs in Japan Vol. -, Pg. 88, 1990. | |
rat | LD50 | parenteral | > 3gm/kg (3000mg/kg) | Drugs in Japan Vol. -, Pg. 114, 1995. | |
rat | LD50 | unreported | 10gm/kg (10000mg/kg) | Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 42(9), Pg. 10, 1977. | |
rat | LDLo | oral | > 5gm/kg (5000mg/kg) | British Medical Journal. Vol. 2, Pg. 197, 1961. | |
rat | LDLo | subcutaneous | > 5gm/kg (5000mg/kg) | British Medical Journal. Vol. 2, Pg. 197, 1961. | |
women | TDLo | oral | 160mg/kg/4D-I (160mg/kg) | BLOOD: AGRANULOCYTOSIS BLOOD: THROMBOCYTOPENIA | Annals of Internal Medicine. Vol. 99, Pg. 573, 1983. |
EPA Genetic Toxicology Program. IARC Cancer Review: Group 3 IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 50 (1990),p. 153.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Animal Limited Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 50 (1990),p. 153.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Human Inadequate Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 50 (1990),p. 153.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) .
Poison by intracerebral route. Moderately toxic by intraperitoneal route. Human systemic effects by ingestion: fever, agranulocytosis, and other blood effects. An experimental teratogen. Mutation data reported. Questionable carcinogen. When heated to decomposition it emits very toxic fumes of NOx and SOx.
Hazard Codes: Xn
Risk Statements: 36/37/38-42/43
R36/37/38:Irritating to eyes, respiratory system and skin.
R42/43:May cause sensitization by inhalation and skin contact.
Safety Statements: 22-26-36/37
S22:Do not breathe dust.
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36/37:Wear suitable protective clothing and gloves.
Ampicillin , its cas register number is 69-53-4. It also can be called D-(-)-alpha-Aminobenzylpenicillin ; Polyflex (Veterinary) ; and (2S,5R,6R)-6-[(R)-2-Amino-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; D-(-)-alpha-Aminobenzylpenicillin .
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