Benzathine penicillin G (CHEM019623)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 06:20:45 UTC
Update Date2016-11-09 01:16:02 UTC
Accession NumberCHEM019623
Identification
Common NameBenzathine penicillin G
ClassSmall Molecule
DescriptionA 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 TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
BeacillinChEBI
Benzathine benzylpenicillinChEBI
Benzathine benzylpenicillineChEBI
Benzathini benzylpenicillinumChEBI
Benzatina bencilpenicilinaChEBI
Benzylpenicillin dibenzylethylenediamine saltChEBI
BicillinChEBI
Bicillin L-aChEBI
CepacilinaChEBI
ExtencillineChEBI
LentopenilChEBI
N,N'-dibenzylethylenediamine bis(benzyl penicillin)ChEBI
Penicillin g benzathineChEBI
Penicillin g benzathine anhydrousChEBI
Penicillin g salt OF N,n'-dibenzylethylenediamineChEBI
PeniduralChEBI
PermapenChEBI
TardocillinChEBI
Benzathine benzylpénicilline panpharmaMeSH
BenzetacilMeSH
PenduranMeSH
Bicillin forteMeSH
Benzathine benzylpenicillin, procaine benzylpenicillin, benzylpenicillin sodium drug combinationMeSH
Benzathine benzylpenicillin, procaine benzylpenicillin drug combinationMeSH
Bicillin-3MeSH
Benzathine benzylpenicillin, procaine benzylpenicillin, drug combinationMeSH
BencelinMeSH
Bicillin laMeSH
Benzathine benzylpenicillin - procaine benzylpenicillinMeSH
Bicillin IIIMeSH
Benzathine benzylpenicillin, procaine benzylpenicillin, benzylpenicillin potassium drug combinationMeSH
Bicillin C-RMeSH
DebecillinMeSH
Peniroger retardMeSH
BrevicilinaMeSH
Bicillin 1MeSH
Benzathine, penicillin gMeSH
Provipen benzatinaMeSH
Benzylpenicillin, benzathineMeSH
RetacillinMeSH
Bicillin L aMeSH
PendysinMeSH
Benzathine penicillinMeSH
PendeponMeSH
RetazillinMeSH
Penicillin, benzathineMeSH
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-carboxylateGenerator
Antibioticos brand OF benzathine benzylpenicillinMeSH
CSL Brand OF benzathine benzylpenicillinMeSH
g Benzathine, penicillinMeSH
I farmacologia brand OF benzathine benzylpenicillinMeSH
Roger brand OF benzathine benzylpenicillinMeSH
Sandoz brand OF penicillin g benzathineMeSH
Antibioticos farma brand OF penicillin g benzathineMeSH
King pharmaceuticals brand OF penicillin g benzathineMeSH
LPGMeSH
Roerig brand OF benzathine benzylpenicillinMeSH
Jenapharm brand OF benzathine benzylpenicillinMeSH
Wyeth brand OF penicillin g benzathineMeSH
Bayer brand OF benzathine benzylpenicillinMeSH
Panpharma brand OF benzathine benzylpenicillinMeSH
Sabater brand OF benzathine benzylpenicillinMeSH
Specia brand OF benzathine benzylpenicillinMeSH
Wassermann brand OF benzathine benzylpenicillinMeSH
Yamanouchi brand OF benzathine benzylpenicillinMeSH
Chemical FormulaC48H56N6O8S2
Average Molecular Mass909.130 g/mol
Monoisotopic Mass908.360 g/mol
CAS Registry Number1538-09-6
IUPAC Namebenzyl[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 Namebenzathine(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 IdentifierInChI=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 KeyBVGLIYRKPOITBQ-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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassQuinolines and derivatives
Sub ClassAminoquinolines and derivatives
Direct Parent4-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 FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00016 g/LALOGPS
logP3.86ALOGPS
logP1.08ChemAxon
logS-6.8ALOGPS
pKa (Strongest Acidic)3.53ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area89.54 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity95.36 m³·mol⁻¹ChemAxon
Polarizability33.44 ųChemAxon
Number of Rings8ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000000009-d9e6081c3e23c83a3d9bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0000000009-d9e6081c3e23c83a3d9bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0000000009-d9e6081c3e23c83a3d9bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000000009-473ba73c7846e1685b75Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0000000009-473ba73c7846e1685b75Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-0000000009-473ba73c7846e1685b75Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB09323
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkBenzathine_benzylpenicillin
Chemspider IDNot Available
ChEBI ID51352
PubChem Compound ID15232
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot 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