Product Name

  • Name

    Ampicillin

  • EINECS 200-709-7
  • CAS No. 69-53-4
  • Article Data34
  • CAS DataBase
  • Density 1.45 g/cm3
  • Solubility NH4OH 1 M: 50 mg/mL, clear, colorless
  • Melting Point 198-200 °C (dec.)(lit.)
  • Formula C16H19N3O4S
  • Boiling Point 683.9 °C at 760 mmHg
  • Molecular Weight 363.437
  • Flash Point 367.4 °C
  • Transport Information
  • Appearance Crystalline solid
  • Safety 22-26-36/37
  • Risk Codes 36/37/38-42/43
  • Molecular Structure Molecular Structure of 69-53-4 (Ampicillin)
  • Hazard Symbols HarmfulXn
  • Synonyms Guicitrina;Marisilan;Nuvapen;Omnipe;Penbristol;Penbritin;Penbritin paediatric;Penbritinsyrup;Penicillin, (aminophenylmethyl)-;Penicline;Pentrexyl;Polyflex;Ponecil;Principen;Roscillin;Synpenin;Tokiocillin;Tolomol;Totacillin;Totalciclina;Ultrabion;Ultrabron;Viccillin;Viccillin S;Wy 5103;4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid, 6-(2-amino-2-phenylacetamido)-3,3-dimethyl-7-oxo-, D-(-)- (8CI);4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[(aminophenylacetyl)amino]-3,3-dimethyl-7-oxo-,[2S-[2a,5a,6b(S*)]]-;(-)-6-(2-Amino-2-phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid;A-Pen;Adobacillin;Albipen;Alpen;Amblosin;Amfipen;Amipenix;Amipenix S;Amotital;Ampi-Bol;Ampi-kel;Ampicillin;Ampicillin A;Ampimed;Ampisyn;Ampitab;Ampivet;Amplital;Austrapen;BRL 1341;Binotal;Britacil;Campicillin;Copharcilin;D-(-)-6-(a-Aminophenylacetamido)penicillanicacid;D-(-)-Ampicillin;D-(-)-a-Aminobenzylpenicillin;D-(-)-a-Aminopenicillin;Dumopen;Ficillin;Grampenil;
  • PSA 138.03000
  • LogP 1.34720

Synthetic route

6-Aminopenicillanic Acid
551-16-6

6-Aminopenicillanic Acid

ampicillin
69-53-4

ampicillin

Conditions
ConditionsYield
With (S)-Phenylglycine methyl ester In ethylene glycol at 20℃; for 48h; Enzymatic reaction;96.7%
6-Aminopenicillanic Acid
551-16-6

6-Aminopenicillanic Acid

A

(R)-phenylglycine
875-74-1

(R)-phenylglycine

B

ampicillin
69-53-4

ampicillin

Conditions
ConditionsYield
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%
6-Aminopenicillanic Acid
551-16-6

6-Aminopenicillanic Acid

(R)-Phenylglycine methyl ester
24461-61-8

(R)-Phenylglycine methyl ester

ampicillin
69-53-4

ampicillin

Conditions
ConditionsYield
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;
6-Aminopenicillanic Acid
551-16-6

6-Aminopenicillanic Acid

(+)-(S)-α-bromophenylacetic acid
60686-78-4

(+)-(S)-α-bromophenylacetic acid

ampicillin
69-53-4

ampicillin

Conditions
ConditionsYield
(i) HN(SiMe3)2, CHCl3, (ii) /BRN= 4946351/, DCC, CH2Cl2, (iii) hexamethylentetramine; Multistep reaction;
6-Aminopenicillanic Acid
551-16-6

6-Aminopenicillanic Acid

N-carboxy-(R)-phenylglycine anhydride
3412-49-5

N-carboxy-(R)-phenylglycine anhydride

ampicillin
69-53-4

ampicillin

Conditions
ConditionsYield
With sodium hydroxide
6β-((R)-2-benzylideneamino-2-phenyl-acetylamino)-penicillanic acid; 1,1,3,3-tetramethyl-butylamine salt
53129-37-6

6β-((R)-2-benzylideneamino-2-phenyl-acetylamino)-penicillanic acid; 1,1,3,3-tetramethyl-butylamine salt

ampicillin
69-53-4

ampicillin

Conditions
ConditionsYield
With 4-methyl-2-pentanone In water
6-Aminopenicillanic Acid
551-16-6

6-Aminopenicillanic Acid

D-phenylglycine methyl ester hydrochloride
19883-41-1

D-phenylglycine methyl ester hydrochloride

ampicillin
69-53-4

ampicillin

Conditions
ConditionsYield
With potassium phosphate; Pseudomonas melanogenum KY 8541 at 30℃; pH=6.5;
pivampicillin
33817-20-8

pivampicillin

ampicillin
69-53-4

ampicillin

Conditions
ConditionsYield
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 phenoxymethyl ester

(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 phenoxymethyl ester

ampicillin
69-53-4

ampicillin

Conditions
ConditionsYield
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 2,5-dioxo-pyrrolidin-1-ylmethyl ester

(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 2,5-dioxo-pyrrolidin-1-ylmethyl ester

ampicillin
69-53-4

ampicillin

Conditions
ConditionsYield
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 2,6-dioxo-piperidin-1-ylmethyl ester

(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 2,6-dioxo-piperidin-1-ylmethyl ester

ampicillin
69-53-4

ampicillin

Conditions
ConditionsYield
With phosphate buffer; sodium chloride In water at 37℃; half-life value, pH 7.4, other ampicillin esters;
phthalimidomethylampicillin

phthalimidomethylampicillin

ampicillin
69-53-4

ampicillin

Conditions
ConditionsYield
With phosphate buffer; sodium chloride In water at 37℃; Rate constant; half-life value, pH 7.4, various pH, 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 2-oxo-benzooxazol-3-ylmethyl ester

(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 2-oxo-benzooxazol-3-ylmethyl ester

ampicillin
69-53-4

ampicillin

Conditions
ConditionsYield
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
203127-11-1

(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
69-53-4

ampicillin

Conditions
ConditionsYield
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 1,1,3-trioxo-1,3-dihydro-1λ6-benzo[d]isothiazol-2-ylmethyl ester

(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 1,1,3-trioxo-1,3-dihydro-1λ6-benzo[d]isothiazol-2-ylmethyl ester

ampicillin
69-53-4

ampicillin

Conditions
ConditionsYield
With phosphate buffer; sodium chloride In water at 37℃; half-life value, pH 7.4, other ampicillin esters;
bacampicillin Hydrochloride
37661-08-8

bacampicillin Hydrochloride

A

ampicillin
69-53-4

ampicillin

B

degradation products

degradation products

Conditions
ConditionsYield
With sodium hydroxide; Tween 80 solution; potassium chloride In water at 35℃; Rate constant; pH 6.00, μ = 0.5; degradation in suspension;
D-α-phenylglycine chloride hydrochloride

D-α-phenylglycine chloride hydrochloride

+5°C,trimethylchlorosilane

+5°C,trimethylchlorosilane

nicotinamide
98-92-0

nicotinamide

diethylamine
109-89-7

diethylamine

A

6-(D-α-aminophenyl-acetamido)-2,2-dimethyl-penam-3-carboxylic acid

6-(D-α-aminophenyl-acetamido)-2,2-dimethyl-penam-3-carboxylic acid

B

ampicillin
69-53-4

ampicillin

Conditions
ConditionsYield
In dichloromethane; water
6-Aminopenicillanic Acid
551-16-6

6-Aminopenicillanic Acid

DL-2-phenylglycine methyl ester hydrochloride
15028-40-7

DL-2-phenylglycine methyl ester hydrochloride

A

ampicillin
19379-33-0

ampicillin

B

ampicillin
69-53-4

ampicillin

Conditions
ConditionsYield
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
551-16-6

6-Aminopenicillanic Acid

D-phenylglycine methyl ester hydrochloride
19883-41-1

D-phenylglycine methyl ester hydrochloride

A

(R)-phenylglycine
875-74-1

(R)-phenylglycine

B

ampicillin
69-53-4

ampicillin

Conditions
ConditionsYield
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
551-16-6

6-Aminopenicillanic Acid

ampicillin
69-53-4

ampicillin

Conditions
ConditionsYield
With penicillin acylasefrom Escherichia coli; water
(R)-Phenylglycine methyl ester
24461-61-8

(R)-Phenylglycine methyl ester

6-aminopenicillinate

6-aminopenicillinate

ampicillin
69-53-4

ampicillin

Conditions
ConditionsYield
With wild-type cocaine esterase In aq. phosphate buffer at 20℃; Enzymatic reaction;
ampicillin
69-53-4

ampicillin

C16H19N3O4S*C7H12N2

C16H19N3O4S*C7H12N2

Conditions
ConditionsYield
In dichloromethane at 20℃; for 1.5h;100%
ampicillin
69-53-4

ampicillin

2-oxoimidazolidine-1-carbonyl chloride
13214-53-4

2-oxoimidazolidine-1-carbonyl chloride

azlocillin
37091-66-0

azlocillin

Conditions
ConditionsYield
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
69-53-4

ampicillin

1-chlorocarbonyl-2-oxo-3-methylcarbonyl-imidazolidine
41730-71-6

1-chlorocarbonyl-2-oxo-3-methylcarbonyl-imidazolidine

sodium 2-ethylhexanoic acid

sodium 2-ethylhexanoic acid

penicillin G
61-33-6

penicillin G

Conditions
ConditionsYield
With triethylamine In methanol; aqueous tetrahydrofurane; water; ethyl acetate95%
With triethylamine In methanol; aqueous tetrahydrofurane; water; ethyl acetate95%
With triethylamine In methanol; aqueous tetrahydrofurane; water; ethyl acetate95%
ampicillin
69-53-4

ampicillin

N,N,N',N'-tetramethylguanidine
80-70-6

N,N,N',N'-tetramethylguanidine

C16H19N3O4S*C5H13N3

C16H19N3O4S*C5H13N3

Conditions
ConditionsYield
In dichloromethane at 20℃; for 1.5h;95%
ampicillin
69-53-4

ampicillin

1-ethyl-3-methyl-1H-imidazol-3-ium chloride
65039-09-0

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
1418122-70-9

(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
ConditionsYield
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
69-53-4

ampicillin

4-ethyl-2,3-dioxopiperazine-1-carbonyl chloride
59703-00-3

4-ethyl-2,3-dioxopiperazine-1-carbonyl chloride

Conditions
ConditionsYield
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
ampicillin
69-53-4

ampicillin

1,8-diazabicyclo[5.4.0]undec-7-ene
6674-22-2

1,8-diazabicyclo[5.4.0]undec-7-ene

C16H19N3O4S*C9H16N2

C16H19N3O4S*C9H16N2

Conditions
ConditionsYield
In dichloromethane at 20℃; for 1.5h;91%
ampicillin
69-53-4

ampicillin

3-chlorocarbonyl-1-methanesulfonyl-2-imidazolidinone
41762-76-9

3-chlorocarbonyl-1-methanesulfonyl-2-imidazolidinone

mezlocillin
51481-65-3

mezlocillin

Conditions
ConditionsYield
With sodium hydroxide In water for 3h;90.5%
ampicillin
69-53-4

ampicillin

acetoacetic acid methyl ester
105-45-3

acetoacetic acid methyl ester

potassium 6β-penicillanate

potassium 6β-penicillanate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide a) RT, 2 h, b) 0 deg C, 4 h;90%
ampicillin
69-53-4

ampicillin

4-chlorobenzophenone
134-85-0

4-chlorobenzophenone

C29H26ClN3O4S

C29H26ClN3O4S

Conditions
ConditionsYield
In methanol for 5h; Reflux;87%
ampicillin
69-53-4

ampicillin

3-(2-hydroxyethyl)-1-methyl-1H-imidazol-3-ium chloride

3-(2-hydroxyethyl)-1-methyl-1H-imidazol-3-ium chloride

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
1418122-71-0

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
ConditionsYield
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%
N-propionyl-N-methyl-carbamic acid chloride

N-propionyl-N-methyl-carbamic acid chloride

ampicillin
69-53-4

ampicillin

penicillin G
61-33-6

penicillin G

Conditions
ConditionsYield
With hydrogenchloride; triethylamine In tetrahydrofuran; aqueous tetrahydrofurane85%
indole-2,3-dione
91-56-5

indole-2,3-dione

ampicillin
69-53-4

ampicillin

(6R)-3,3-dimethyl-7-oxo-6-(2-(([E]-2-oxoindolin-3-ylidene)amino)-2-phenylacetamido)-4-thia-1-azabicyclo[3.2.0]hept ane-2-carboxylic acid

(6R)-3,3-dimethyl-7-oxo-6-(2-(([E]-2-oxoindolin-3-ylidene)amino)-2-phenylacetamido)-4-thia-1-azabicyclo[3.2.0]hept ane-2-carboxylic acid

Conditions
ConditionsYield
In methanol Reflux;85%
ampicillin
69-53-4

ampicillin

3-methylbenzene-1,2-diol
488-17-5

3-methylbenzene-1,2-diol

6-[2-(5-methyl-3,4-dioxocyclohexa-1,5-dienylamino)-2-phenylacetylamino]penicillanic acid
1078142-74-1

6-[2-(5-methyl-3,4-dioxocyclohexa-1,5-dienylamino)-2-phenylacetylamino]penicillanic acid

Conditions
ConditionsYield
With oxygen at 20℃; for 1.5h; pH=5.6; aq. acetate buffer; Enzymatic reaction;83%
sebacoyl chloride
111-19-3

sebacoyl chloride

ampicillin
69-53-4

ampicillin

C42H52N6O10S2
111466-73-0

C42H52N6O10S2

Conditions
ConditionsYield
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%
ampicillin
69-53-4

ampicillin

acetylacetone
123-54-6

acetylacetone

C21H25N3O5S

C21H25N3O5S

Conditions
ConditionsYield
In methanol Reflux;82%
trihexyl(tetradecyl)phosphonium chloride
258864-54-9

trihexyl(tetradecyl)phosphonium chloride

ampicillin
69-53-4

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
1418122-67-4

(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
ConditionsYield
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
69-53-4

ampicillin

p-nitrophenyl N-(prop-2-ynyl)carbamate

p-nitrophenyl N-(prop-2-ynyl)carbamate

(2S,5R,6R)-3,3-dimethyl-7-oxo-6-[[(2R)-2-phenyl-2-(prop-2-ynylcarbamoylamino)acetyl]amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

(2S,5R,6R)-3,3-dimethyl-7-oxo-6-[[(2R)-2-phenyl-2-(prop-2-ynylcarbamoylamino)acetyl]amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

Conditions
ConditionsYield
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
59577-32-1

2-(4-methoxybenzyloxycarbonyloxyimino)-2-phenylacetonitrile

ampicillin
69-53-4

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
460052-60-2

(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
ConditionsYield
With sodium hydrogencarbonate In 1,4-dioxane for 6h; pH=7.8;76.5%
cetylpyridinium chloride
123-03-5

cetylpyridinium chloride

ampicillin
69-53-4

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 cetylpyridinium

(2S,5R,6R)-6-(R-2-amino-2-phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylate cetylpyridinium

Conditions
ConditionsYield
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
71-91-0

tetraethylammonium bromide

ampicillin
69-53-4

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
1418122-66-3

(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
ConditionsYield
Stage #1: tetraethylammonium bromide With Amberlite IRA-400-OH In methanol
Stage #2: ampicillin With ammonium In methanol at 20℃; for 1h;
76%
ampicillin
69-53-4

ampicillin

phenyl isocyanate
103-71-9

phenyl isocyanate

6-β-(α-(Phenylureido)-D-phenylacetamido)-penicillansaeure

6-β-(α-(Phenylureido)-D-phenylacetamido)-penicillansaeure

Conditions
ConditionsYield
With TEA In tetrahydrofuran; water for 2h; Ambient temperature;75%
C20H15N5O6

C20H15N5O6

ampicillin
69-53-4

ampicillin

C32H29N7O7S

C32H29N7O7S

Conditions
ConditionsYield
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
69-53-4

ampicillin

1-benzyl N-carbobenzoxy-L-glutamate
65706-99-2

1-benzyl N-carbobenzoxy-L-glutamate

N-benzyloxycarbonyl-D-glutamyl α-benzyl ester γ-D-phenylglycyl-6-aminopenicillanic acid

N-benzyloxycarbonyl-D-glutamyl α-benzyl ester γ-D-phenylglycyl-6-aminopenicillanic acid

Conditions
ConditionsYield
With chloroformic acid ethyl ester; triethylamine In dichloromethane 1.) -10 deg C, 0.5 h, 2.) room temperature, 1 h;71%
choline chloride
67-48-1

choline chloride

ampicillin
69-53-4

ampicillin

(2-hydroxyethyl)trimethylammonium 6-(2-amino-2-phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
1418122-69-6

(2-hydroxyethyl)trimethylammonium 6-(2-amino-2-phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

Conditions
ConditionsYield
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
69-53-4

ampicillin

N6-[N2',N6'-bis(2,3-diacetoxybenzoyl)-L-lysyl]-N2-(2,3-diacetoxybenzoyl)-L-lysine

N6-[N2',N6'-bis(2,3-diacetoxybenzoyl)-L-lysyl]-N2-(2,3-diacetoxybenzoyl)-L-lysine

N-{N6'-[N2",N6"-bis(2,3-diacetoxybenzoyl)-L-lysyl]-N2'-(2,3-diacetoxybenzoyl)-L-lysyl}-ampicillin sodium salt

N-{N6'-[N2",N6"-bis(2,3-diacetoxybenzoyl)-L-lysyl]-N2'-(2,3-diacetoxybenzoyl)-L-lysyl}-ampicillin sodium salt

Conditions
ConditionsYield
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
69-53-4

ampicillin

N2-[N2',N6'-bis(2,3-diacetoxybenzoyl)-L-lysyl]-N6-(2,3-diacetoxybenzoyl)-L-lysine
439152-20-2

N2-[N2',N6'-bis(2,3-diacetoxybenzoyl)-L-lysyl]-N6-(2,3-diacetoxybenzoyl)-L-lysine

N-{N2'-[N2",N6"-bis(2,3-diacetoxybenzoyl)-L-lysyl]-N6-(2,3-diacetoxybenzoyl)-L-lysyl}-ampicillin sodium salt

N-{N2'-[N2",N6"-bis(2,3-diacetoxybenzoyl)-L-lysyl]-N6-(2,3-diacetoxybenzoyl)-L-lysyl}-ampicillin sodium salt

Conditions
ConditionsYield
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%

Ampicillin Chemical Properties

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 Uses

 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..

Ampicillin Production

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.

Ampicillin Toxicity Data With Reference

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.

Ampicillin Consensus Reports

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) .

Ampicillin Safety Profile

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: HarmfulXn
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 Specification

 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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