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69-57-8

Basic Information
CAS No.: 69-57-8
Name: 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid, 3,3-dimethyl-7-oxo-6-[(2-phenylacetyl)amino]- (2S,5R,6R)-, sodium salt(1:1)
Molecular Structure:
Molecular Structure of 69-57-8 (4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid, 3,3-dimethyl-7-oxo-6-[(2-phenylacetyl)amino]- (2S,5R,6R)-, sodium salt(1:1))
Formula: C16H17N2NaO4S
Molecular Weight: 356.37 .
Synonyms: 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid, 3,3-dimethyl-7-oxo-6-(2-phenylacetamido)-, monosodium salt (8CI);4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid,3,3-dimethyl-7-oxo-6-[(phenylacetyl)amino]-[2S-(2a,5a,6b)]-, monosodium salt;Americanpenicillin;Benzylpenicillin sodium;Benzylpenicillin sodium salt;Monosodiumbenzylpenicillin;Mycofarm;Nobak;Novocillin;Penicillin G sodium;Penicillin G sodium salt;Penilaryn;Sodiumbenzylpenicillin G;Sodium penicillin;Sodium penicillin II;Veticillin;(2S,5R,6R)-3,3-diméthyl-7-oxo-6-[(phénylacétyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate de sodium;[2S-(2a,5a,6b)]-3,3-Dimethyl-7-oxo-6-[(phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid Monosodium Salt;Penicillin G Sodium;
EINECS: 200-710-2
Density: 1.41
Melting Point: 209-212 °C
Boiling Point: 663.3 °C at 760 mmHg
Flash Point: 355 °C
Solubility: 100 mg/mL in water
Appearance: White powder
Hazard Symbols: HarmfulXn
Risk Codes: 42/43
Safety: 22-36/37-45
Transport Information:
PSA: 114.84000
LogP: -0.14510
Synthetic route
69-57-8

Penicillin G sodium

109-76-2

Trimethylenediamine

C19H28N4O4S

Conditions
ConditionsYield
With sodium carbonate In water at 0 - 20℃; for 3h; pH=4; Inert atmosphere;97%
69-57-8

Penicillin G sodium

74-88-4

methyl iodide

653-89-4

penicillin G methyl ester

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 26℃;92%
In dimethyl sulfoxide for 4h; Ambient temperature;
51164-42-2

N-chloromethyl-N-methylbenzamide

69-57-8

Penicillin G sodium

158877-60-2

(2S,5R,6R)-3,3-Dimethyl-7-oxo-6-phenylacetylamino-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid (benzoyl-methyl-amino)-methyl ester

Conditions
ConditionsYield
In tetrahydrofuran Ambient temperature;89%
1233875-87-0

α-bromo-4,5-dimethoxy-2-nitrophenylacetic acid allyl ester

69-57-8

Penicillin G sodium

1233876-01-1

penicillin G α-allyloxycarbonyl-4,5-dimethoxy-2-nitrobenzyl ester

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 20℃;84%
53413-67-5

6-nitroveratrylbromide

69-57-8

Penicillin G sodium

1415712-97-8

2-nitro-4,5-dimethoxy-benzyl-6-β-(2-phenylacetamido)penicillinate

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 20℃; for 17h;81%
18997-19-8

Chloromethyl pivalate

69-57-8

Penicillin G sodium

25031-07-6

(pivaloyloxy)methyl (2S,5R,6R)-3,3-dimethyl-7-oxo-6-(2-phenylacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

Conditions
ConditionsYield
In N,N-dimethyl-formamide for 24h; Ambient temperature;80%
69-57-8

Penicillin G sodium

2746-25-0

p-Methoxybenzyl bromide

30200-14-7

benzylpenicillin 4-methoxybenzyl ester

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 20℃; for 3h; Inert atmosphere;80%
31282-95-8

1-(chloromethyl)pyrrolidin-2-one

69-57-8

Penicillin G sodium

62351-29-5

(2S,5R,6R)-3,3-Dimethyl-7-oxo-6-phenylacetylamino-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 2-oxo-pyrrolidin-1-ylmethyl ester

Conditions
ConditionsYield
In tetrahydrofuran Ambient temperature;79%
646-19-5

heptane-1,7-diamine

69-57-8

Penicillin G sodium

C23H36N4O4S

Conditions
ConditionsYield
With sodium carbonate In water at 0 - 20℃; for 3h; pH=4; Inert atmosphere;77%
67-56-1

methanol

69-57-8

Penicillin G sodium

silver nitrate

C34H42Ag2N4O10S2

Conditions
ConditionsYield
In water for 0.0833333h;67%
462-94-2

1,5-diaminopentane

69-57-8

Penicillin G sodium

C21H32N4O4S

Conditions
ConditionsYield
With sodium carbonate In water at 0 - 20℃; for 3h; pH=4; Inert atmosphere;61%
4270-65-9

N-methyl-N-chloromethylacetamide

69-57-8

Penicillin G sodium

51164-31-9

(2S,5R,6R)-3,3-Dimethyl-7-oxo-6-phenylacetylamino-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid (acetyl-methyl-amino)-methyl ester

Conditions
ConditionsYield
In tetrahydrofuran Ambient temperature;56%
69-57-8

Penicillin G sodium

653-89-4

penicillin G methyl ester

Conditions
ConditionsYield
With perchloric acid In diethyl ether50%
69-57-8

Penicillin G sodium

144175-29-1

4-Chloro-N-chloromethyl-N-methyl-benzamide

158877-61-3

(2S,5R,6R)-3,3-Dimethyl-7-oxo-6-phenylacetylamino-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid [(4-chloro-benzoyl)-methyl-amino]-methyl ester

Conditions
ConditionsYield
In tetrahydrofuran Ambient temperature;50%
69-57-8

Penicillin G sodium

2450-71-7

Propargylamine

(2S,5R,6R)-3,3-dimethyl-7-oxo-6-(2-phenylacetamido)-N-(prop-2-yn-1-yl)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxamide

Conditions
ConditionsYield
Stage #1: Penicillin G sodium With hydrogenchloride In water
Stage #2: With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane for 0.0333333h;
Stage #3: Propargylamine Further stages;
38%
1600-27-7

mercury(II) diacetate

69-57-8

Penicillin G sodium

64-19-7

acetic acid

39650-23-2

(2S,3S)-1-(2-methylprop-1-en-1-yl)-4-oxo-3-(2-phenylacetamido)azetidin-2-yl acetate

Conditions
ConditionsYield
at 70℃;23%
69-57-8

Penicillin G sodium

17947-12-5

N-benzylidene-O-[6β-(2-phenyl-acetylamino)-penicillanoyl]-hydroxylamine

Conditions
ConditionsYield
(i) ClCO2Et, Py, acetone, (ii) /BRN= 1209596/; Multistep reaction;
717813-39-3

4-amino-3,5-diiodo-benzoic acid 2-diethylamino-ethyl ester

69-57-8

Penicillin G sodium

6β-(2-phenyl-acetylamino)-penicillanic acid; 4-amino-3,5-diiodo-benzoic acid 2-diethylamino-ethyl ester salt (1:1)

Conditions
ConditionsYield
In water
70204-58-9

4-benzoylamino-benzoic acid 2-diethylamino-ethyl ester

69-57-8

Penicillin G sodium

6β-(2-phenyl-acetylamino)-penicillanic acid; 4-benzoylamino-benzoic acid 2-diethylamino-ethyl ester salt

Conditions
ConditionsYield
In water
129083-47-2

4-amino-3,5-dibromo-benzoic acid 2-diethylamino-ethyl ester

69-57-8

Penicillin G sodium

6β-(2-phenyl-acetylamino)-penicillanic acid; 4-amino-3,5-dibromo-benzoic acid 2-diethylamino-ethyl ester salt (1:1)

Conditions
ConditionsYield
In water
861531-56-8

4-(4-nitro-benzoylamino)-benzoic acid 2-diethylamino-ethyl ester

69-57-8

Penicillin G sodium

6β-(2-phenyl-acetylamino)-penicillanic acid; 4-(4-nitro-benzoylamino)-benzoic acid 2-diethylamino-ethyl ester salt

Conditions
ConditionsYield
In water
69-57-8

Penicillin G sodium

N-p-tosyl-procaine

6β-(2-phenyl-acetylamino)-penicillanic acid; 4-(toluene-4-sulfonylamino)-benzoic acid 2-diethylamino-ethyl ester salt

Conditions
ConditionsYield
In water
69-57-8

Penicillin G sodium

34104-15-9

penicillin G 1-oxide

Conditions
ConditionsYield
With sodium periodate In water
69-57-8

Penicillin G sodium

75-64-9

tert-butylamine

34104-21-7

6β-(2-phenyl-acetylamino)-penicillanic acid tert-butylamide

Conditions
ConditionsYield
(i) Et3N, ClCO2Et, CHCl3, (ii) /BRN= 605267/; Multistep reaction;
69-57-8

Penicillin G sodium

620-03-1

furan-2-carbaldehyde oxime

17947-15-8

N-furfurylidene-O-[6β-(2-phenyl-acetylamino)-penicillanoyl]-hydroxylamine

Conditions
ConditionsYield
(i) ClCO2Et, Py, acetone, (ii) /BRN= 80664/; Multistep reaction;
107-10-8

propylamine

69-57-8

Penicillin G sodium

B

27826-46-6, 47550-94-7

(2R,4S)-5,5-Dimethyl-2-(phenylacetylamino-propylcarbamoyl-methyl)-thiazolidine-4-carboxylic acid

Conditions
ConditionsYield
In water at 30℃; Mechanism; Rate constant; ionic strength: 0.25 M (KCl), k1, k22, k3;
151-18-8

2-cyanoethylamine

69-57-8

Penicillin G sodium

B

(2R,4S)-2-[(2-Cyano-ethylcarbamoyl)-phenylacetylamino-methyl]-5,5-dimethyl-thiazolidine-4-carboxylic acid

Conditions
ConditionsYield
In water at 30℃; Mechanism; Rate constant; ionic strength: 0.25 M (KCl), k1, k22, k3;
753-90-2

trifluoroethylamine

69-57-8

Penicillin G sodium

B

(2R,4S)-5,5-Dimethyl-2-[phenylacetylamino-(2,2,2-trifluoro-ethylcarbamoyl)-methyl]-thiazolidine-4-carboxylic acid

Conditions
ConditionsYield
In water at 30℃; Mechanism; Rate constant; ionic strength: 0.25 M (KCl), k1, k22, k3;
69-57-8

Penicillin G sodium

B

(2R,4S)-5,5-Dimethyl-2-[phenylacetylamino-(2-sulfo-ethylcarbamoyl)-methyl]-thiazolidine-4-carboxylic acid

Conditions
ConditionsYield
In water at 30℃; Mechanism; Rate constant; ionic strength: 0.25 M (KCl), k1, k22, k3;
69-57-8

Penicillin G sodium

26265-69-0

2-ammonioethylamine

B

(2R,4S)-2-[(2-Amino-ethylcarbamoyl)-phenylacetylamino-methyl]-5,5-dimethyl-thiazolidine-4-carboxylic acid

Conditions
ConditionsYield
In water at 30℃; Mechanism; Rate constant; ionic strength: 0.25 M (KCl), k1, k22, k3;
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643-43-6
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Specification

The Penicillin G Sodium, with the CAS registry number 69-57-8 and EINECS registry number 200-710-2, has the systematic name of sodium (2S,5R,6R)-3,3-dimethyl-7-oxo-6-[(phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate. And the molecular formula of this chemical is C16H17N2NaO4S. It is a kind of white powder, and has a good  solubility in water. What's more, it should be stored at 2-8°C.

The physical properties of Penicillin G Sodium are as following: (1)ACD/LogP: 1.67; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -1.31; (4)ACD/LogD (pH 7.4): -2.06; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 6; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 4; (12)Polar Surface Area: 103.22 Å2; (13)Flash Point: 355 °C; (14)Enthalpy of Vaporization: 102.51 kJ/mol; (15)Boiling Point: 663.3 °C at 760 mmHg; (16)Vapour Pressure: 1.69E-18 mmHg at 25°C.

Preparation and uses of Penicillin G Sodium: It can be obtained by fermentation of seperated penicilumchryso-genum. It is used in the treatment of a variety of infections. And it is effective against most gram-positive bacteria and against gram-negative cocci. What's more, it also has also been used as an experimental convulsant because of its actions on gamma-aminobutyric acid mediated synaptic transmission.

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; 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)Cc1ccccc1)[C@H]3SC2(C)C
(2)InChI: InChI=1/C16H18N2O4S.Na/c1-16(2)12(15(21)22)18-13(20)11(14(18)23-16)17-10(19)8-9-6-4-3-5-7-9;/h3-7,11-12,14H,8H2,1-2H3,(H,17,19)(H,21,22);/q;+1/p-1/t11-,12+,14-;/m1./s1
(3)InChIKey: FCPVYOBCFFNJFS-WAGRTCGHBK

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LDLo intramuscular 60mg/kg (60mg/kg)   Laboratory Animal Science. Vol. 30, Pg. 524, 1980.
guinea pig LDLo intravenous 150mg/kg (150mg/kg) GASTROINTESTINAL: OTHER CHANGES Arzneimittel-Forschung. Drug Research. Vol. 9, Pg. 31, 1959.
mouse LD50 intracrebral 3800ug/kg (3.8mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 55, Pg. 23, 1959.
mouse LD50 intramuscular 2800mg/kg (2800mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 9, Pg. 31, 1959.
mouse LD50 intraperitoneal 3314mg/kg (3314mg/kg)   Antibiotics Annual. Vol. 3, Pg. 540, 1955/1956.
mouse LD50 intravenous 1500mg/kg (1500mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Arzneimittel-Forschung. Drug Research. Vol. 9, Pg. 31, 1959.
mouse LD50 oral > 4gm/kg (4000mg/kg)   Antibiotics Annual. Vol. 3, Pg. 540, 1955/1956.
mouse LD50 subcutaneous 4750mg/kg (4750mg/kg)   Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 55, Pg. 23, 1959.
rat LD50 intravenous 3020mg/kg (3020mg/kg) CARDIAC: OTHER CHANGES

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Arzneimittel-Forschung. Drug Research. Vol. 9, Pg. 31, 1959.
rat LD50 oral 6916mg/kg (6916mg/kg) BEHAVIORAL: TREMOR

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

GASTROINTESTINAL: OTHER CHANGES
Archives des Maladies Professionnelles de Medecine du Travail et de Securite Sociale. Vol. 39, Pg. 259, 1978.
rat LD50 parenteral 2900ug/kg (2.9mg/kg)   Antimicrobial Agents and Chemotherapy Vol. -, Pg. 863, 1965.