Penicillin-G

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Names

[ CAS No. ]:
61-33-6

[ Name ]:
Penicillin-G

[Synonym ]:
penicillin, benzyl-
cilloral
MFCD00036193
benzyl penicillin
4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6-[(2-phenylacetyl)amino]-, (2S,5R,6R)-
cosmopen
dropcillin
cilopen
abbocillin
[2S-(2a,5a,6b)]-3,3-Dimethyl-7-oxo-6-[(phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid
(2S,5R,6R)-6-[(E)-(1-Hydroxy-2-phenylethylidene)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Penicillinic acid, benzyl-
galofak
Penicillin II
Pencillin G
pradupen
Ursopen
penicillin G
UNII-Q42T66VG0C
gelacillin
4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6-[(phenylacetyl)amino]-, (2S,5R,6R)-
(2S,5R,6R)-3,3-Dimethyl-7-oxo-6-[(phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[[(1E)-1-hydroxy-2-phenylethylidene]amino]-3,3-dimethyl-7-oxo-, (2S,5R,6R)-
EINECS 204-038-0
pencilling

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Boiling Point ]:
663.3±55.0 °C at 760 mmHg

[ Molecular Formula ]:
C₁₆H₁₈N₂O₄S

[ Molecular Weight ]:
334.390

[ Flash Point ]:
355.0±31.5 °C

[ Exact Mass ]:
334.098724

[ PSA ]:
112.01000

[ LogP ]:
1.67

[ Appearance of Characters ]:
powder

[ Vapour Pressure ]:
0.0±2.1 mmHg at 25°C

[ Index of Refraction ]:
1.655

[ Water Solubility ]:
H2O: 100 mg/mL

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: XH9400000

CHEMICAL NAME :: 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6- (2-phenylacetamido)-

CAS REGISTRY NUMBER :: 61-33-6

BEILSTEIN REFERENCE NO. :: 0044740

LAST UPDATED :: 199612

DATA ITEMS CITED :: 24

MOLECULAR FORMULA :: C16-H18-N2-O4-S

MOLECULAR WEIGHT :: 334.42

WISWESSER LINE NOTATION :: T45 ANV ESTJ CMV1R& F F GVQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Parenteral

SPECIES OBSERVED :: Human - child

DOSE/DURATION :: 15000 units/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Ear) - changes in cochlear structure or function Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - dyspnea

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 8 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Unreported

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 9 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >5 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 3500 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 329 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intracerebral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 5700 ug/kg

TOXIC EFFECTS :: Brain and Coverings - other degenerative changes

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Unreported

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 7800 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intracerebral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 1118 ug/kg

TOXIC EFFECTS :: Brain and Coverings - other degenerative changes

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Unreported

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 4940 ug/kg

TOXIC EFFECTS :: Brain and Coverings - other degenerative changes

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intracerebral

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 653 ug/kg

TOXIC EFFECTS :: Brain and Coverings - other degenerative changes

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Unreported

SPECIES OBSERVED :: Rodent - guinea pig

DOSE/DURATION :: 38 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - hamster

DOSE/DURATION :: 24 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Behavioral - food intake (animal) Gastrointestinal - hypermotility, diarrhea

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - hamster

DOSE/DURATION :: 96 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Behavioral - food intake (animal) Gastrointestinal - hypermotility, diarrhea

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 104 ku/kg/4D-I

TOXIC EFFECTS :: Blood - changes in other cell count (unspecified) Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - dehydrogenases

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intramuscular

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 750 units/kg/5D-I

TOXIC EFFECTS :: Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol) Immunological Including Allergic - decrease in humoral immune response Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - phosphatases

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 2600 mg/kg/65W-I

TOXIC EFFECTS :: Tumorigenic - equivocal tumorigenic agent by RTECS criteria Tumorigenic - tumors at site of application

MUTATION DATA

TYPE OF TEST :: Mutation test systems - not otherwise specified

TEST SYSTEM :: Microorganism - not otherwise specified

DOSE/DURATION :: 20 ug/L

REFERENCE :: AMACCQ Antimicrobial Agents and Chemotherapy. (American Soc. for Microbiology, 1913 I St., NW, Washington, DC 20006) V.1- 1972- Volume(issue)/page/year: 17,572,1980 *** OCCUPATIONAL EXPOSURE LIMITS *** OEL-RUSSIA:STEL 0.1 mg/m3 JAN 1993 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X3134 No. of Facilities: 151 (estimated) No. of Industries: 1 No. of Occupations: 5 No. of Employees: 2695 (estimated) No. of Female Employees: 1750 (estimated)

Safety Information

[ Hazard Codes ]:
Xn

[ Risk Phrases ]:
R42/43

[ Safety Phrases ]:
S36/37

[ WGK Germany ]:
2

[ RTECS ]:
XH9700000

[ HS Code ]:
32041900

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

6-Aminopenicillanic acid
ampicillin Trihydrate
Phenylacetyl chloride
benzyl 6β-phenylacetamidopenicillanate
benzyl (2S,5R,6R)-6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
6β-(4-nitro-benzylideneamino)-penicillanic acid benzyl ester
3-cyclohexyloxy-carbonyl-imidazolidin-2-on-1-carbonyl chloride
Ampicillin
Sodium 2-(2-aminothiazol-4-yl)-(Z)-2-(4-methylenecyclohexyloxyimino)acetate

DownStream

6-Aminopenicillanic acid
Phenylacetic acid
D-penicillamine
2-Thiazolidineaceticacid, 4-carboxy-5,5-dimethyl-a-[(2-phenylacetyl)amino]-
benzylpenicillenic acid
5-benzyl-2,2-dimethyl-2,3,7,7a-tetrahydroimidazo[5,1-b][1,3]thiazole-3,7-dicarboxylic acid
Penicillin G potassium
2-Phenylacetamide

Customs

[ HS Code ]: 32041900

Related Compounds

penicillin-G
PENICILLIN-G PROCAIN SALT
Penicillin-G-phenylester.
Penicillin-G, monosodium salt
penicillin-G,triethylamine salt
Penicillin-G 4-methoxybenzyl ester sulfoxide
4-((Cyclohexylamino)methyl)benzoic acid hydrochloride
(1-{6,6-Dimethylbicyclo[3.1.1]hept-2-en-2-yl}-2,2-dimethylcyclopropyl)methanamine
[1-(2-cyclopropylethyl)-5-methyl-1H-1,2,3-triazol-4-yl]methanamine
2-[2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)acetamido]pentanoic acid
1-[(2,4-Dichlorophenyl)methyl]-N-(1,1-dimethylethyl)-2-methyl-1H-indole-3-methanamine
2-Methoxy-6-(pyrazol-1-yl)-benzonitrile
1H-3-Benzazepin-7-ol, 8-chloro-2,3,4,5-tetrahydro-5-(3-iodophenyl)-3-methyl-, (S)-
(4-Methyl-tetrahydro-furan-2-yl)-methanol
N-(1-cyanocyclopentyl)-2-[4-(4-fluorobenzenesulfonyl)-1,4-diazepan-1-yl]acetamide
4,5,6,7-Tetrahydrobenzo[d]isoxazole-3-carbaldehyde