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

Übersicht

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.

Zusammensetzung

Element Symbol Atome Atommasse
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

Elementare Zusammensetzung

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%

Verwendung

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

Wissenswertes

  • ✦ 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

Sicherheit

  • ⚠ 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

Eigenschaften

Typ
organic
Zustand
solid
Molmasse
334,39 g/mol
Dichte
1,4100 g/cm³
Schmelzpunkt
214,0 °C
Löslichkeit
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

Auch bekannt als

Benzylpenicillin Penicillin

Verwandte Verbindungen

Caffeine

C₈H₁₀N₄O₂

Coumarin

C₉H₆O₂

Acetone

(CH₃)₂CO

Acrylic Acid

C₃H₄O₂

Cysteine

C₃H₇NO₂S

DDT

C₁₄H₉Cl₅

Alanine

C₃H₇NO₂

Diazepam

C₁₆H₁₃ClN₂O

Dichloromethane

CH₂Cl₂

Butane

C₄H₁₀

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).