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Basic Information
CAS No.: 69-52-3
Name: Ampicillin sodium
Molecular Structure:
Molecular Structure of 69-52-3 (Ampicillin sodium)
Formula: C16H18N3NaO4S
Molecular Weight: 371.392
Synonyms: Alpen-N;Amcill-S;Ampicillin natrium;Ampicillin sodium;Ampicillin sodium salt;Binotal sodium;Citteral;D(-)-alpha-Aminobenzylpenicillin sodium salt;Domicillin;Monosodium (2S,5R,6R)-6-((R)-2-Amino-2-phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylate;
EINECS: 200-708-1
Melting Point: 215 °C (dec.)(lit.)
Boiling Point: 683.9 °C at 760 mmHg
Flash Point: 367.4 °C
Solubility: water: 50 mg/mL, clear, very faintly yellow
Appearance: White powder
Hazard Symbols: IrritantXi
Risk Codes: 42/43
Safety: 22-36/37-45
PSA: 140.86000
LogP: 0.01250
Synthetic route
71780-15-9

N-(1-methyl-2-ethoxycarbonylvinyl)ampicillin sodium

69-52-3

ampicillin sodium

Conditions
ConditionsYield
With water at 25℃; Rate constant; hydrolysis at pH 7.4;
69-52-3

ampicillin sodium

141-97-9

ethyl acetoacetate

71780-15-9

N-(1-methyl-2-ethoxycarbonylvinyl)ampicillin sodium

Conditions
ConditionsYield
In isopropyl alcohol at 25℃; for 3h;75%
Downstream Products
76497-13-7
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Consensus Reports

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) .

Specification

The Ampicillin sodium, with the CAS registry number 69-52-3 and EINECS registry number 200-708-1, has the systematic name of sodium (2S,5R,6R)-6-{[(2R)-2-amino-2-phenylacetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate. It is a kind of white powder, and the molecular formula of this chemical is C16H18N3NaO4S. As a semi-synthetic derivative of penicillin, it functions as an orally active broad-spectrum antibiotic. And it should be stored at 2-8°C.

The physical properties of Ampicillin sodium are as following: (1)ACD/LogP: 1.35; (2)# of Rule of 5 Violations: 0; (3)#H bond acceptors: 7; (4)#H bond donors: 4; (5)#Freely Rotating Bonds: 5; (6)Polar Surface Area: 106.46 Å2; (7)Flash Point: 367.4 °C; (8)Enthalpy of Vaporization: 105.36 kJ/mol; (9)Boiling Point: 683.9 °C at 760 mmHg; (10)Vapour Pressure: 1.21E-19 mmHg at 25°C.

Synthetic method and uses of Ampicillin sodium: It can be obtained by the salifing of penbritin: Add penbritin to the water, and adjust the pH to 9 by adding sodium hydroxide solution. Then you can get the product after a series of decoloration, filtration and drying. And because of its tericidal action, it is often used in the molecular biology and also used for tissue culture(to prevent microbial contamination).

You should be cautious while dealing with this chemical. It may cause sensitization by inhalation and skin contact. Therefore, you had better take the following instructions: Wear suitable protective clothing and gloves, and in case of accident or if you feel unwell, seek medical advice immediately (show label where possible); Do not breathe dust.

You can still convert the following datas into molecular structure:
(1)SMILES: [Na+].O=C([O-])[C@@H]2N3C(=O)[C@@H](NC(=O)[C@@H](c1ccccc1)N)[C@H]3SC2(C)C
(2)InChI: InChI=1/C16H19N3O4S.Na/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);/q;+1/p-1/t9-,10-,11+,14-;/m1./s1
(3)InChIKey: KLOHDWPABZXLGI-IANBRGBNBB

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 5700mg/kg (5700mg/kg)   Toxicology and Applied Pharmacology. Vol. 18, Pg. 185, 1971.
mouse LD50 oral > 5314mg/kg (5314mg/kg)   British Journal of Pharmacology and Chemotherapy. Vol. 18, Pg. 356, 1962.
mouse LD50 subcutaneous > 5314mg/kg (5314mg/kg)   British Journal of Pharmacology and Chemotherapy. Vol. 18, Pg. 356, 1962.
mouse LDLo intravenous 2657mg/kg (2657mg/kg) BEHAVIORAL: TREMOR

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
British Journal of Pharmacology and Chemotherapy. Vol. 18, Pg. 356, 1962.
rat LD50 intraperitoneal 7400mg/kg (7400mg/kg)   Toxicology and Applied Pharmacology. Vol. 18, Pg. 185, 1971.
rat LD50 oral > 5314mg/kg (5314mg/kg)   British Journal of Pharmacology and Chemotherapy. Vol. 18, Pg. 356, 1962.
rat LD50 subcutaneous > 5314mg/kg (5314mg/kg)   British Journal of Pharmacology and Chemotherapy. Vol. 18, Pg. 356, 1962.
women TDLo oral 100mg/kg/5D (100mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

GASTROINTESTINAL: OTHER CHANGES
Lancet. Vol. 2, Pg. 707, 1978.