Penicillin G

C₁₆H₁₈N₂O₄S

IUPAC: (2S,5R,6R)-3,3-Dimethyl-7-oxo-6-(2-phenylacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

CAS: 61-33-6

Overview

Penicillin G was the first antibiotic discovered, by Alexander Fleming in 1928 from the mold Penicillium notatum. It works by inhibiting bacterial cell wall synthesis. Its discovery revolutionized medicine and has saved an estimated 200 million lives.

Composition

Element Symbol Atoms Atomic Mass
Hydrogen H 18 1.0080
Carbon C 16 12.0110
Nitrogen N 2 14.0070
Oxygen O 4 15.9990
Sulfur S 1 32.0600

Elemental Composition

H
Hydrogen ×18
5.4%
C
Carbon ×16
57.5%
N
Nitrogen ×2
8.4%
O
Oxygen ×4
19.1%
S
Sulfur ×1
9.6%

Uses

  • • Antibiotic for bacterial infections
  • • Syphilis treatment
  • • Streptococcal infection treatment
  • • Starting material for semi-synthetic penicillins

Fun Facts

  • ✦ Fleming noticed mold contamination on a Petri dish had killed surrounding bacteria, leading to penicillin's discovery
  • ✦ Mass production of penicillin saved countless lives during World War II

Safety

  • ⚠ Allergic reactions (up to 10% of population)
  • ⚠ Anaphylaxis in severe cases
  • ⚠ Antibiotic resistance

Structure

SMILES

CC1(C(N2C(S1)C(C2=O)NC(=O)CC3=CC=CC=C3)C(=O)O)C

Properties

Type
organic
State
solid
Molar Mass
334.39 g/mol
Density
1.4100 g/cm³
Melting Point
214.0 °C
Solubility
soluble

Molecular Descriptors

Exact Mass
334.0987
XLogP
1.8
TPSA
112.0 Ų
H-Bond Donors
2
H-Bond Acceptors
5
Rotatable Bonds
4
Heavy Atoms
23
Complexity
530.0

Also Known As

Benzylpenicillin Penicillin

Related Compounds

1,2-Dichloroethane

C₂H₄Cl₂

1,3-Butadiene

C₄H₆

1,4-Dioxane

C₄H₈O₂

1-Butanol

C₄H₁₀O

2-Propanol

C₃H₈O

Acetaldehyde

CH₃CHO

Acetamide

C₂H₅NO

Acetic Anhydride

C₄H₆O₃

Acetone

(CH₃)₂CO

Acetonitrile

C₂H₃N

Frequently Asked Questions

What is Penicillin G?
Penicillin G (C₁₆H₁₈N₂O₄S) is a organic compound with the IUPAC name (2S,5R,6R)-3,3-Dimethyl-7-oxo-6-(2-phenylacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid.
What is the molecular weight of Penicillin G?
Penicillin G has a molar mass of 334.39 g/mol.
What state is Penicillin G at room temperature?
Penicillin G is a solid at room temperature.
Is Penicillin G organic or inorganic?
Penicillin G is classified as an organic compound.
What elements make up Penicillin G?
Penicillin G (C₁₆H₁₈N₂O₄S) is composed of Hydrogen (H), Carbon (C), Nitrogen (N), Oxygen (O), Sulfur (S).