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4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid, 6-[[(2R)-2-amino-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-, sodium salt(1:1), (2S,5R,6R)-(CAS No. 69-52-3)

4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid, 6-[[(2R)-2-amino-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-, sodium salt(1:1), (2S,5R,6R)- C16H18N3NaO4S (cas 69-52-3) Molecular Structure

69-52-3 Structure

Identification and Related Records

【Name】
4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid, 6-[[(2R)-2-amino-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-, sodium salt(1:1), (2S,5R,6R)-
【CAS Registry number】
69-52-3
【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(EC#)】
200-708-1
【Molecular Formula】
C16H18N3NaO4S (Products with the same molecular formula)
【Molecular Weight】
371.38
【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
【Canonical SMILES】
CC1(C(N2C(S1)C(C2=O)NC(=O)C(C3=CC=CC=C3)N)C(=O)O)C
【Isomers 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
【MOL File】
69-52-3.mol

Chemical and Physical Properties

【Appearance】
white to off-white solid
【Melting Point】
215℃ (dec.)
【Boiling Point】
683.9 °C at 760 mmHg
【Flash Point】
683.9 °C at 760 mmHg
【Water】
H2O: 50 mg/mL, clear, very faintly yellow
【Solubilities】
H2O: 50 mg/mL, clear, very faintly yellow
【Color/Form】
white with slight yellow cast
【Stability】
Stable under normal temperatures and pressures.
【HS Code】
29419000
【Storage temp】
2-8°C
【Spectral properties】
Optical rotation = +287.9 deg at 20 deg C (C=1 in H2O)
【Computed Properties】
Molecular Weight:349.40476 [g/mol]
Molecular Formula:C16H19N3O4S
XLogP3:-1.1
H-Bond Donor:3
H-Bond Acceptor:6
Rotatable Bond Count:4
Tautomer Count:4
Exact Mass:349.109627
MonoIsotopic Mass:349.109627
Topological Polar Surface Area:138
Heavy Atom Count:24
Formal Charge:0
Complexity:562
Isotope Atom Count:0
Defined Atom Stereocenter Count:4
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:4
Feature 3D Donor Count:2
Feature 3D Anion Count:1
Feature 3D Cation Count:1
Feature 3D Hydrophobe Count:1
Feature 3D Ring Count:2
Effective Rotor Count:5.8
Conformer Sampling RMSD:0.8
CID Conformer Count:30

Safety and Handling

【Hazard Codes】
Xi:Irritant
【Risk Statements】
R42/43
【Safety Statements 】
S22;S36/37;S45
【Safety】
Hazard Codes:Xi
Risk Statements:42/43-36/37/38-22
42/43:May cause sensitization by inhalation and skin contact
36/37/38:Irritating to eyes, respiratory system and skin
22:Harmful if swallowed
Safety Statements:22-36/37-45-36-26
22:Do not breathe dust
36/37:Wear suitable protective clothing and gloves
45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)
36:Wear suitable protective clothing
26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
WGK Germany:2
HS Code:29419000
【Formulations/Preparations】
USP anhydrous ampicillin contains 900-1050 ug/mg ampicillin (calculated as the anhydrous base). Ampicillin is available in 125-, 200-, 250-, and 500-mg tablets that contain 90-120% labelled active ingredient, in 125-, 250-, and 500-mg capsules containing 90-120% labelled active ingredient, and as oral suspensions of 100, 125, and 250 mg/5 ml containing 90-120% of the labelled active ingredient and probenecid.
【Exposure Standards and Regulations】
Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392).
【Specification】

White powder
Safety Statements:22-36/37-45-36-26
22:Do not breathe dust
36/37:Wear suitable protective clothing and gloves
45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)
36:Wear suitable protective clothing
26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
【Disposal Methods】
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

ACYLATION OF 6-AMINOPENICILLANIC ACID WITH D-(-)-GLYCINE
DOYLE ET AL, US PATENT 2,985,648 (1961); EIDEM, BRITISH PATENT 902,703 (1962 TO BEECHAM); DOYLE ET AL, J CHEM SOC 1962, 1440; KAUFMANN, BAUER, US PATENT 3,079,307 (1963 TO BAYER); JOHNSON, WOLFE, & JOHNSON, HARDCASTLE, US PATENTS 3,140,282 & 3,157,640 (BOTH 1964 TO BRISTOL-MYERS)...
...GRANT, ALBURN, US PATENT 3,144,445 (1964 TO AM HOME PRODUCTS); DANE, DOCKNER, BER 98, 789 (1965). ... DL-FORM.../OF SODIUM SALT/ BRITISH PATENT 958,824 (1964 TO PFIZER).
Ampicillin is produced by the acylation of 6-aminopenicillanic acid with D-(-)-alpha-phenylglycine by either microbiological or chemical synthesis.
U.S. Exports

(1978) 7.51X10+7 GRAMS (INCL SALTS)
(1979) 1.89X10+7 GRAMS (INCL SALTS)
U.S. Imports

(1977) 3.83X10+7 GRAMS (PRINCPL CUSTMS DISTS)
(1979) 2.25X10+7 GRAMS (PRINCPL CUSTMS DISTS)
U.S. Production

(1977) 5.30X10+8 GRAMS
(1979) 4.53X10+8 GRAMS
【Usage】
Antibiotic.

Biomedical Effects and Toxicity

【Pharmacological Action】
- Substances that reduce the growth or reproduction of BACTERIA.
【Therapeutic Uses】
Penicillins
FOR MILD TO MODERATELY SEVERE DISEASE, ORAL...ADULTS...1-4 G/DAY, DIVIDED INTO EQUAL PORTIONS...EVERY 6 HR. FOR SEVERE INFECTIONS...BEST TO ADMIN... PARENTERALLY...6-12 G/DAY. ...MENINGITIS REQUIRES...300-400 MG/KG/DAY PARENTERALLY (IN EQUALLY DIVIDED PORTIONS...EVERY 4 HR) FOR CHILDREN, & 12 G OR MORE/DAY FOR ADULTS.
DOSE VARIES WITH TYPE & SEVERITY OF INFECTION...RENAL FUNCTION &...AGE. FOR CHILDREN.../NOT/ ON BASIS OF BODY WT OR SURFACE AREA; BECAUSE DRUG...EXCRETED MAINLY BY KIDNEY ...RENAL FUNCTION TO GREAT EXTENT DETERMINES DOSE. VERY YOUNG BABIES...REQUIRE SMALL DOSES ...CHILDREN 3-4 YR.../DOSE/ ALMOST AS LARGE AS...ADULTS.
Ampicillin /is/ indicated in the treatment of acute otitis media caused by susceptible organisms. /Included in US product labeling/
Ampicillin /is/ indicated in the treatment of bacterial pharyngitis cuased by susceptible organisms. /Included in US product labeling/
Ampicillin /is/ indicated in the treatment of bacterial pneumonia caused by susceptible organisms. /Included in US product labeling/
Ampicillin /is/ indicated in the treatment of sinusitis caused by susceptible organisms. /Included in US product labeling/
Ampicillin /is/ indicated in the treatment of bacterial urinary tract infections caused by susceptible organisms. /Included in US product labeling/
Ampicillin /is/ indicated in the treatment of chlamydia infections in pregnant women who cannot tolerate erythromycin. /Included in US product labeling/
Ampicillin /is/ used in the treatment of typhoid fever caused by Salmonella typhi. /NOT included in US product labeling; Not included in Canadian product labeling/
Ampicillin /is/ indicated in the prophylaxis of bacterial endocarditis caused by susceptible organisms. /Included in US product labeling; Not included in Canadian product labeling/
Ampicillin /is/ indicated in the treatment of bacterial endocarditis caused by susceptible organisms. /Included in US product labeling/
Ampicillin (parenteral) /is/ indicated in the treatment of listeriosis caused by Listeria monocytogenes. /Included in US product labeling; Not included in Canadian product labeling/
Ampicillin (parenteral) /is/ indicated in the treatment of bacterial meningitis caused by susceptible organisms. /Included in US product labeling/
Ampicillin (parenteral) /is/ indicated in the treatment of infections caused by Pasteurella multocida. /Included in US product labeling; Not included in Canadian product labeling/
Ampicillin ... /is/ indicated in the treatment of bronchitis caused by susceptible organisms. /Included in US product labeling/
Ampicillin (parenteral) /is/ indicated in the treatment of bacterial septicemia caused by susceptible organisms. /Included in US product labeling/
Ampicillin (parenteral) /is/ used in the treatment of leptospirosis caused by Leptospira sp. /NOT included in US product labeling; Not included in Canadian product labeling/
【Biomedical Effects and Toxicity】
INTAKE OF FOOD PRIOR TO INGESTION OF AMPICILLIN RESULTS IN LESS COMPLETE ABSORPTION. ... /IT/ APPEARS IN BILE, UNDERGOES ENTEROHEPATIC CIRCULATION & IS EXCRETED IN...FECES. BILIARY CONCN...DEPENDENT ON INTEGRITY OF GALLBLADDER & ITS DUCTS.
Ampicillin is distributed to liver, bile, muscle, kidney, crop, and fat following absorption from the GI or injection site. Ampicillin has been used therapeutically and prophylactically for avian salmonellosis with promising results. ... Ampicillin is excreted in bile.
Anhydrous ampicillin and ampicillin trihydrate are generally stable in the presence of acidic gastric secretions, and 30-55% of an oral dose of the drugs is absorbed from the GI tract in fasting adults. Although peak serum concn may occur as soon as 1 hr after administration, the maximum serum concn is usually attained in approx 2 hr.
Two hr after oral administration of 250 mg of ampicillin in fasting individuals, average peak serum concn of 1.8-2.9 ug/ml are attained. A 500-mg oral dose results in average peak serum concn of 3-6 ug/ml. Concn of the antibiotic in serum are less than 1 ug/ml 6 hr after a 500-mg oral dose.
Although higher peak serum ampicillin concn and larger areas under the serum concn-time curves (AUCs) have been reported following oral administration of anhydrous ampicillin than following the trihydrate, the differences are generally not considered clinically important. As oral dosage of ampicillin is increased from 500 mg to 2 g, the fraction of the dose absorbed from the GI tract decreased and there is a nonlinear relationship between dosage and peak serum concn or AUCs of ampicillin.
Presence of food in the GI tract generally decreases the rate and extent of absorption of ampicillin.
Following IM administration of ampicillin sodium, peak serum concn are generally attained more quickly and are higher than those resulting from equivalent doses of ampicillin given orally. In premature neonates younger than 7 days of age, IM administration of a single ampicillin dose of 50 m/kg has been reported to produce mean serum concn of 104, 87, 60, and 31 ug/ml at 1, 4, 8, and 12 hr, respectively, after the dose. The same dose in full-term neonates younger than 7 days of age produced mean serum concn of 75, 64, 34, and 20 ug/ml at the same time intervals.
Following IV administration over 20 minutes of a single 2-g dose of ampicillin in healthy adults, serum concn of ampicillin averaged 47.6, 23.3, 10.8, and 3.7 ug/ml at 30 min, 1 hr, 2 hr, and 4 hr, respectively, after the infusion.
Serum ampicillin concn are higher and the serum half-life is prolonged in patients with impaired renal function. Serum concn of the drug are also higher and more prolonged in premature or full-term neonates younger than 6 days of age than in full-term neonates 6 days of age or older.
In one study in neonates with meningitis, average ampicillin concn in CSF ranged from 1-28 ug/ml (11-65% of simultaneous serum concn) during the 7-hr period following IV administration of 40-70 mg/kg. Highest CSF concn occurred @ 3-7 hr.
Ampicillin is distributed into bile. Biliary concn of ampicillin in patients with normal biliary function may be 1-30 times greater than simultaneous serum concn following a single oral dose of ampicillin.
Assay of serum collected after a single sc dose of sodium ampicillin @ 10 mg/kg bw to guinea-pigs yielded ampicillin levels of approx 10 ug/ml @ 5 min, which fell rapidly to less than 0.2 ug/ml @ 60 min ... .
Ampicillin is relatively stable in the acid contents of the stomach; anhydrous or trihydrated ampicillin is absorbed incompletely from the gut after oral admin. Peak concn in plasma (2-6 mg/l after an oral dose of 500 mg) occur within 1-2 hr. Ester prodrugs ... and the condensation prodrug ... of ampicillin are absorbed more readily than ampicillin ... Ampicillin @ 500 mg given by im injection as the sodium salt produced plasma peaks of 7-14 mg/l within about 1 hr ... .
Ampicillin is distributed widely, and therapeutic concn can be achieved in soft tissues, including ascitic, pleural and joint fluids ... Only 20% of ampicillin is bound to plasma proteins ... It crosses the placenta ... and detectable concn of ampicillin occur in the milk of nursing mothers ... .
Ampicillin is excreted via renal glomerular and tubular routes in the urine ...
There is a number of studies to suggest that the pharmacokinetics of beta-lactam antibiotics are altered during pregnancy, indicating faster elimination of these antibiotics and lowered plasma concentrations. These changes are largely related to the physiological changes taking place in the maternal body. [Heikkila A, Erkkola R; Clin Pharmacokinet 27 (1): 49-62 (1994)] PubMed Abstract

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