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    Chemistry

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    Also known as: Benzathine benzylpenicillin, Cepacilina, Lentopenil, Tardocillin, Beacillin, Penidural
    Molecular Formula
    C48H56N6O8S2
    Molecular Weight
    909.1  g/mol
    InChI Key
    BVGLIYRKPOITBQ-ANPZCEIESA-N
    Penicillin G Benzathine
    Semisynthetic antibiotic prepared by combining the sodium salt of penicillin G with N,N'-dibenzylethylenediamine.
    1 2D Structure

    Penicillin G Benzathine

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    benzyl-[2-(benzylazaniumyl)ethyl]azanium;(2S,5R,6R)-3,3-dimethyl-7-oxo-6-[(2-phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
    2.1.2 InChI
    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
    2.1.3 InChI Key
    BVGLIYRKPOITBQ-ANPZCEIESA-N
    2.1.4 Canonical SMILES
    CC1(C(N2C(S1)C(C2=O)NC(=O)CC3=CC=CC=C3)C(=O)[O-])C.CC1(C(N2C(S1)C(C2=O)NC(=O)CC3=CC=CC=C3)C(=O)[O-])C.C1=CC=C(C=C1)C[NH2+]CC[NH2+]CC2=CC=CC=C2
    2.1.5 Isomeric SMILES
    CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)CC3=CC=CC=C3)C(=O)[O-])C.CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)CC3=CC=CC=C3)C(=O)[O-])C.C1=CC=C(C=C1)C[NH2+]CC[NH2+]CC2=CC=CC=C2
    2.2 Synonyms
    2.2.1 MeSH Synonyms

    1. Bencelin

    2. Benzathine Benzylpnicilline Panpharma

    3. Benzathine Benzylpenicillin

    4. Benzathine Penicillin

    5. Benzathine, Penicillin G

    6. Benzetacil

    7. Benzylpenicillin, Benzathine

    8. Bicillin

    9. Bicillin L A

    10. Bicillin La

    11. Brevicilina

    12. Cepacilina

    13. Debecillin

    14. Extencilline

    15. Pendepon

    16. Penduran

    17. Pendysin

    18. Penicillin G Benzathine

    19. Penicillin G Benzathine Anhydrous

    20. Penicillin, Benzathine

    21. Penidural

    22. Peniroger Retard

    23. Permapen

    24. Provipen Benzatina

    25. Tardocillin

    2.2.2 Depositor-Supplied Synonyms

    1. Benzathine Benzylpenicillin

    2. Cepacilina

    3. Lentopenil

    4. Tardocillin

    5. Beacillin

    6. Penidural

    7. Chebi:51352

    8. Benzylpenicillin Dibenzylethylenediamine Salt

    9. Penicillin G Salt Of N,n'-dibenzylethylenediamine

    10. N,n'-dibenzylethylenediamine Bis(benzyl Penicillin)

    11. Epitope Id:224559

    12. Db09323

    13. N,n'-dibenzylethane-1,2-diaminium Bis{2,2-dimethyl-6beta-(phenylacetamido)penam-3alpha-carboxylate}

    2.3 Create Date
    2009-01-30
    3 Chemical and Physical Properties
    Molecular Weight 909.1 g/mol
    Molecular Formula C48H56N6O8S2
    Hydrogen Bond Donor Count4
    Hydrogen Bond Acceptor Count10
    Rotatable Bond Count13
    Exact Mass908.36010511 g/mol
    Monoisotopic Mass908.36010511 g/mol
    Topological Polar Surface Area263 Ų
    Heavy Atom Count64
    Formal Charge0
    Complexity696
    Isotope Atom Count0
    Defined Atom Stereocenter Count6
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count3
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 2  
    Drug NameBicillin l-a
    PubMed HealthPenicillin G Benzathine (Injection)
    Drug ClassesAntibiotic
    Drug LabelBicillin L-A (penicillin G benzathine injectable suspension) is available for deep intramuscular injection. Penicillin G benzathine is prepared by the reaction of dibenzylethylene diamine with two molecules of penicillin G. It is chemically designate...
    Active IngredientPenicillin g benzathine
    Dosage FormInjectable
    RouteInjection
    Strength300,000 units/ml; 600,000 units/ml
    Market StatusPrescription
    CompanyKing Pharms

    2 of 2  
    Drug NameBicillin l-a
    PubMed HealthPenicillin G Benzathine (Injection)
    Drug ClassesAntibiotic
    Drug LabelBicillin L-A (penicillin G benzathine injectable suspension) is available for deep intramuscular injection. Penicillin G benzathine is prepared by the reaction of dibenzylethylene diamine with two molecules of penicillin G. It is chemically designate...
    Active IngredientPenicillin g benzathine
    Dosage FormInjectable
    RouteInjection
    Strength300,000 units/ml; 600,000 units/ml
    Market StatusPrescription
    CompanyKing Pharms

    5 Pharmacology and Biochemistry
    5.1 MeSH Pharmacological Classification

    Anti-Bacterial Agents

    Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)

    5.2 ATC Code

    J - Antiinfectives for systemic use

    J01 - Antibacterials for systemic use

    J01C - Beta-lactam antibacterials, penicillins

    J01CE - Beta-lactamase sensitive penicillins

    J01CE08 - Benzathine benzylpenicillin

    DRUG PRODUCT COMPOSITIONS

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    DOSAGE - INJECTABLE;INJECTION - 150,000 UNITS...DOSAGE - INJECTABLE;INJECTION - 150,000 UNITS/ML;150,000 UNITS/ML

    USFDA APPLICATION NUMBER - 50138

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    DOSAGE - INJECTABLE;INJECTION - 300,000 UNITS...DOSAGE - INJECTABLE;INJECTION - 300,000 UNITS/ML;300,000 UNITS/ML

    USFDA APPLICATION NUMBER - 50138

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    DOSAGE - INJECTABLE;INJECTION - 900,000 UNITS...DOSAGE - INJECTABLE;INJECTION - 900,000 UNITS/2ML;300,000 UNITS/2ML

    USFDA APPLICATION NUMBER - 50138

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    DOSAGE - INJECTABLE;INJECTION - 300,000 UNITS...DOSAGE - INJECTABLE;INJECTION - 300,000 UNITS/ML

    USFDA APPLICATION NUMBER - 50141

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    DOSAGE - INJECTABLE;INJECTION - 600,000 UNITS...DOSAGE - INJECTABLE;INJECTION - 600,000 UNITS/ML

    USFDA APPLICATION NUMBER - 50141

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