ContaminantDB: Benzathine penicillin G

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-22 06:20:45 UTC

Update Date

2026-04-05 17:23:16 UTC

Accession Number

CHEM019623

Identification

Common Name

Benzathine penicillin G

Class

Small Molecule

Description

A benzathine(2+) salt in which the counter anions are benzylpenicillin(1-). Drug-of-choice when prolonged low concentrations of benzylpenicillin are required and appropriate.

Contaminant Sources

ToxCast & Tox21 Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Beacillin	ChEBI
Benzathine benzylpenicillin	ChEBI
Benzathine benzylpenicilline	ChEBI
Benzathini benzylpenicillinum	ChEBI
Benzatina bencilpenicilina	ChEBI
Benzylpenicillin dibenzylethylenediamine salt	ChEBI
Bicillin	ChEBI
Bicillin L-a	ChEBI
Cepacilina	ChEBI
Extencilline	ChEBI
Lentopenil	ChEBI
N,N'-dibenzylethylenediamine bis(benzyl penicillin)	ChEBI
Penicillin g benzathine	ChEBI
Penicillin g benzathine anhydrous	ChEBI
Penicillin g salt OF N,n'-dibenzylethylenediamine	ChEBI
Penidural	ChEBI
Permapen	ChEBI
Tardocillin	ChEBI
Benzathine benzylpénicilline panpharma	MeSH
Benzetacil	MeSH
Penduran	MeSH
Bicillin forte	MeSH
Benzathine benzylpenicillin, procaine benzylpenicillin, benzylpenicillin sodium drug combination	MeSH
Benzathine benzylpenicillin, procaine benzylpenicillin drug combination	MeSH
Bicillin-3	MeSH
Benzathine benzylpenicillin, procaine benzylpenicillin, drug combination	MeSH
Bencelin	MeSH
Bicillin la	MeSH
Benzathine benzylpenicillin - procaine benzylpenicillin	MeSH
Bicillin III	MeSH
Benzathine benzylpenicillin, procaine benzylpenicillin, benzylpenicillin potassium drug combination	MeSH
Bicillin C-R	MeSH
Debecillin	MeSH
Peniroger retard	MeSH
Brevicilina	MeSH
Bicillin 1	MeSH
Benzathine, penicillin g	MeSH
Provipen benzatina	MeSH
Benzylpenicillin, benzathine	MeSH
Retacillin	MeSH
Bicillin L a	MeSH
Pendysin	MeSH
Benzathine penicillin	MeSH
Pendepon	MeSH
Retazillin	MeSH
Penicillin, benzathine	MeSH
N,N'-dibenzylethane-1,2-diamine;(2S,5R,6R)-3,3-dimethyl-7-oxo-6-[(2-phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate	Generator
Antibioticos brand OF benzathine benzylpenicillin	MeSH
CSL Brand OF benzathine benzylpenicillin	MeSH
g Benzathine, penicillin	MeSH
I farmacologia brand OF benzathine benzylpenicillin	MeSH
Roger brand OF benzathine benzylpenicillin	MeSH
Sandoz brand OF penicillin g benzathine	MeSH
Antibioticos farma brand OF penicillin g benzathine	MeSH
King pharmaceuticals brand OF penicillin g benzathine	MeSH
LPG	MeSH
Roerig brand OF benzathine benzylpenicillin	MeSH
Jenapharm brand OF benzathine benzylpenicillin	MeSH
Wyeth brand OF penicillin g benzathine	MeSH
Bayer brand OF benzathine benzylpenicillin	MeSH
Panpharma brand OF benzathine benzylpenicillin	MeSH
Sabater brand OF benzathine benzylpenicillin	MeSH
Specia brand OF benzathine benzylpenicillin	MeSH
Wassermann brand OF benzathine benzylpenicillin	MeSH
Yamanouchi brand OF benzathine benzylpenicillin	MeSH

Chemical Formula

C₄₈H₅₆N₆O₈S₂

Average Molecular Mass

909.130 g/mol

Monoisotopic Mass

908.360 g/mol

CAS Registry Number

1538-09-6

IUPAC Name

benzyl[2-(benzylazaniumyl)ethyl]azanium bis((2S,5R,6R)-3,3-dimethyl-7-oxo-6-(2-phenylacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate)

Traditional Name

benzathine(2+); bis(benzylpenicillin(1-))

SMILES

[H][N+]([H])(CC[N+]([H])([H])CC1=CC=CC=C1)CC1=CC=CC=C1.[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)CC1=CC=CC=C1)C([O-])=O.[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)CC1=CC=CC=C1)C([O-])=O

InChI Identifier

InChI=1S/2C16H18N2O4S.C16H20N2/c2*1-16(2)12(15(21)22)18-13(20)11(14(18)23-16)17-10(19)8-9-6-4-3-5-7-9;1-3-7-15(8-4-1)13-17-11-12-18-14-16-9-5-2-6-10-16/h2*3-7,11-12,14H,8H2,1-2H3,(H,17,19)(H,21,22);1-10,17-18H,11-14H2/t2*11-,12+,14-;/m11./s1

InChI Key

BVGLIYRKPOITBQ-ANPZCEIESA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as 4-aminoquinolines. These are organic compounds containing an amino group attached to the 4-position of a quinoline ring system.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Aminoquinolines and derivatives

Direct Parent

4-aminoquinolines

Alternative Parents

Substituents

4-aminoquinoline
Haloquinoline
Chloroquinoline
Aminopyridine
Sulfuric acid
Secondary aliphatic/aromatic amine
Aryl chloride
Aryl halide
Pyridine
Benzenoid
Heteroaromatic compound
Organic sulfuric acid or derivatives
Tertiary aliphatic amine
Tertiary amine
1,2-aminoalcohol
Azacycle
Secondary amine
Alkanolamine
Organonitrogen compound
Organochloride
Organopnictogen compound
Organic oxygen compound
Organohalogen compound
Alcohol
Amine
Organic nitrogen compound
Organic oxide
Organooxygen compound
Primary alcohol
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.00016 g/L	ALOGPS
logP	3.86	ALOGPS
logP	1.08	ChemAxon
logS	-6.8	ALOGPS
pKa (Strongest Acidic)	3.53	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	89.54 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	95.36 m³·mol⁻¹	ChemAxon
Polarizability	33.44 Å³	ChemAxon
Number of Rings	8	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0000000009-d9e6081c3e23c83a3d9b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0000000009-d9e6081c3e23c83a3d9b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-0000000009-d9e6081c3e23c83a3d9b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0000000009-473ba73c7846e1685b75	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0000000009-473ba73c7846e1685b75	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-0000000009-473ba73c7846e1685b75	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB09323

HMDB ID

Not Available

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Benzathine_benzylpenicillin

Chemspider ID

Not Available

ChEBI ID

51352

PubChem Compound ID

15232

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

1. https://www.ncbi.nlm.nih.gov/pubmed/?term=23060081

2. https://www.ncbi.nlm.nih.gov/pubmed/?term=24468375

3. https://www.ncbi.nlm.nih.gov/pubmed/?term=7396623

4. https://www.ncbi.nlm.nih.gov/pubmed/?term=765515

5. https://www.ncbi.nlm.nih.gov/pubmed/?term=9241301

Benzathine penicillin G (CHEM019623)

Structure for CHEM019623: Benzathine penicillin G