CAS No.69-53-4,Ampicillin Suppliers

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Basic Information

Molecular Structure:
CAS No.:	69-53-4
Name:	Ampicillin
Article Data:	34

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

Synthetic route

: 551-16-6
6-Aminopenicillanic Acid

: 69-53-4
ampicillin

Conditions

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

: 551-16-6
6-Aminopenicillanic Acid

: 700-63-0, 6485-52-5, 6485-67-2, 58429-87-1
(R)-phenylglycine amide

A: 875-74-1
(R)-phenylglycine

B: 69-53-4
ampicillin

Conditions

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%

...Expand

: 551-16-6
6-Aminopenicillanic Acid

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

: 69-53-4
ampicillin

Conditions

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;

: 551-16-6
6-Aminopenicillanic Acid

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

: 69-53-4
ampicillin

Conditions

Conditions	Yield
(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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With potassium phosphate; Pseudomonas melanogenum KY 8541 at 30℃; pH=6.5;

: 33817-20-8
pivampicillin

: 69-53-4
ampicillin

Conditions

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 phenoxymethyl ester

: 69-53-4
ampicillin

Conditions

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

: 69-53-4
ampicillin

Conditions

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

Raw Materials

700-63-0

Downstream Products

611-73-4

875-74-1

61-33-6

51481-65-3

37091-66-0

551-16-6

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Chemistry

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

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..

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.

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.

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) .

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 NO_x and SO_x.
Hazard Codes: Harmful 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.

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 .