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Basic Information

Molecular Structure:
CAS No.:	69-57-8
Name:	Penicillin G sodium salt

Formula:	C₁₆H₁₇N₂NaO₄S
Molecular Weight:	356.378
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:	Xn
Risk Codes:	42/43
Safety:	22-36/37-45
PSA:	114.84000
LogP:	-0.14510

Synthetic route

: 69-57-8
Penicillin G sodium

: 109-76-2
Trimethylenediamine

: C19H28N4O4S

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
In tetrahydrofuran Ambient temperature;	79%

: 646-19-5
heptane-1,7-diamine

: 69-57-8
Penicillin G sodium

: C23H36N4O4S

Conditions

Conditions	Yield
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

Conditions	Yield
In water for 0.0833333h;	67%

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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.