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Ampicillin

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Name

Ampicillin

EINECS 200-709-7
CAS No. 69-53-4 Density 1.45 g/cm3
PSA 138.03000 LogP 1.34720
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 N/A 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;

Article Data 34

Ampicillin Synthetic route

551-16-6

6-Aminopenicillanic Acid

69-53-4

ampicillin

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

6-Aminopenicillanic Acid

A

875-74-1

(R)-phenylglycine

B

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%
551-16-6

6-Aminopenicillanic Acid

24461-61-8

(R)-Phenylglycine methyl ester

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;
551-16-6

6-Aminopenicillanic Acid

60686-78-4

(+)-(S)-α-bromophenylacetic acid

69-53-4

ampicillin

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

6-Aminopenicillanic Acid

3412-49-5

N-carboxy-(R)-phenylglycine anhydride

69-53-4

ampicillin

Conditions
ConditionsYield
With sodium hydroxide
53129-37-6

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

69-53-4

ampicillin

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

6-Aminopenicillanic Acid

19883-41-1

D-phenylglycine methyl ester hydrochloride

69-53-4

ampicillin

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

pivampicillin

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

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

69-53-4

ampicillin

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

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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