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CAS No.: | 69-53-4 |
---|---|
Name: | Ampicillin |
Article Data: | 34 |
Molecular Structure: | |
Formula: | C16H19N3O4S |
Molecular Weight: | 363.437 |
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; |
EINECS: | 200-709-7 |
Density: | 1.45 g/cm3 |
Melting Point: | 198-200 °C (dec.)(lit.) |
Boiling Point: | 683.9 °C at 760 mmHg |
Flash Point: | 367.4 °C |
Solubility: | NH4OH 1 M: 50 mg/mL, clear, colorless |
Appearance: | Crystalline solid |
Hazard Symbols: | Xn |
Risk Codes: | 36/37/38-42/43 |
Safety: | 22-26-36/37 |
PSA: | 138.03000 |
LogP: | 1.34720 |
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; |
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; |
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 .