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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


USDMF

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01

Bristol Europe Spa

United Kingdom

USDMF

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26th North American ISSX
Not Confirmed

01

Bristol Europe Spa

United Kingdom
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26th North American ISSX
Not Confirmed

GDUFA

DMF Review : N/A

Rev. Date :

Pay. Date :

DMF Number : 13655

Submission : 1998-09-01

Status : Inactive

Type : II

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02

Pfizer Inc

U.S.A

USDMF

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26th North American ISSX
Not Confirmed

02

Pfizer Inc

U.S.A
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26th North American ISSX
Not Confirmed

GDUFA

DMF Review : N/A

Rev. Date :

Pay. Date :

DMF Number : 13318

Submission : 1998-09-01

Status : Inactive

Type : II

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03

Sandoz Gmbh

Switzerland

USDMF

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26th North American ISSX
Not Confirmed

03

Sandoz Gmbh

Switzerland
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26th North American ISSX
Not Confirmed

GDUFA

DMF Review : Complete

Rev. Date : 2018-04-19

Pay. Date : 2018-03-23

DMF Number : 13294

Submission : 1998-09-01

Status : Active

Type : II

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04

26th North American ISSX
Not Confirmed

04

26th North American ISSX
Not Confirmed

GDUFA

DMF Review : N/A

Rev. Date :

Pay. Date :

DMF Number : 13328

Submission : 1998-09-01

Status : Inactive

Type : II

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CEP/COS

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01

SANDOZ GMBH Kundl AT

Switzerland
26th North American ISSX
Not Confirmed
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SANDOZ INDUSTRIAL PRODUCTS GMBH Fra...

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Digital Content Digital Content
R1-CEP 2002-111 - Rev 01
Withdrawn by Holder
Chemical
2009-10-22
2018-01-19
373
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SANDOZ INDUSTRIAL PRODUCTS GMBH Fra...

Gabon
26th North American ISSX
Not Confirmed
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SANDOZ INDUSTRIAL PRODUCTS GMBH Fra...

Gabon
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26th North American ISSX
Not Confirmed

Certificate Number : R1-CEP 2002-111 - Rev 01

Status : Withdrawn by Holder

Issue Date : 2009-10-22

Type : Chemical

Substance Number : 373

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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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