PENICILLIN V BENZATHINE TETRAHYDRATE

First approved in 1955

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C16H20N2.2C16H18N2O5S.4H2O
Molecular Weight	1013.184
Optical Activity	UNSPECIFIED
Defined Stereocenters	6 / 6
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of PENICILLIN V BENZATHINE TETRAHYDRATE

Structure Search

SMILES

O.O.O.O.C(CNCC1=CC=CC=C1)NCC2=CC=CC=C2.[H][C@]34SC(C)(C)[C@@H](N3C(=O)[C@H]4NC(=O)COC5=CC=CC=C5)C(O)=O.[H][C@]67SC(C)(C)[C@@H](N6C(=O)[C@H]7NC(=O)COC8=CC=CC=C8)C(O)=O

InChI

InChIKey=WGLORUYLLMHSJU-CJHXQPGBSA-N

InChI=1S/2C16H18N2O5S.C16H20N2.4H2O/c2*1-16(2)12(15(21)22)18-13(20)11(14(18)24-16)17-10(19)8-23-9-6-4-3-5-7-9;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;4*1H2/t2*11-,12+,14-;;;;;/m11...../s1

HIDE SMILES / InChI

Molecular Formula	H2O
Molecular Weight	18.0153
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C16H20N2
Molecular Weight	240.3434
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C16H18N2O5S
Molecular Weight	350.39
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	3 / 3
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://www.drugbank.ca/drugs/DB00417
Curator's Comment: Description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/label/2012/064071s006lbl.pdf

Penicillin V is a penicillin beta-lactam antibiotic used in the treatment of bacterial infections caused by susceptible, usually gram-positive, organisms. The name "penicillin" can either refer to several variants of penicillin available, or to the group of antibiotics derived from the penicillins. Penicillin V has in vitro activity against gram-positive and gram-negative aerobic and anaerobic bacteria. The bactericidal activity of Penicillin V results from the inhibition of cell wall synthesis and is mediated through Penicillin V binding to penicillin binding proteins (PBPs). Penicillin V is stable against hydrolysis by a variety of beta-lactamases, including penicillinases, and cephalosporinases and extended spectrum beta-lactamases. By binding to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, Penicillin V inhibits the third and last stage of bacterial cell wall synthesis. Cell lysis is then mediated by bacterial cell wall autolytic enzymes such as autolysins; it is possible that Penicillin V interferes with an autolysin inhibitor. Used for the treatment of mild to moderately severe infections (e.g. dental infection, infections in the heart, middle ear infections, rheumatic fever, scarlet fever, skin infections, upper and lower respiratory tract infections) due to microorganisms.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Staphylococcus aureus 67 Target ID: CHEMBL352 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16495241	Inhibitor 8297
Penicillin-binding protein 1A 45 Target ID: Q8XJ01 Gene ID: 990276.0 Gene Symbol: pbpA Target Organism: Clostridium perfringens (strain 13 / Type A) Sources: http://www.drugbank.ca/drugs/DB00417	Inhibitor 8297
Penicillin-binding protein 2a 17 Target ID: CHEMBL3512 Sources: http://www.drugbank.ca/drugs/DB00417	Inhibitor 8297
Streptococcus pneumoniae 25 Target ID: CHEMBL347 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3172134	Inhibitor 8297
Bacterial penicillin-binding protein 233 Target ID: CHEMBL2354204 Sources: http://www.genome.jp/dbget-bin/www_bget?D05411+D00497+D08360	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Pneumococcal infections 9 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2012/064071s006lbl.pdf	Curative	Approved 8429	Penicillin V Approved Use Penicillin V potassium tablets and Penicillin V potassium for oral solution are indicated in the treatment of mild to moderately severe infections due to penicillin G-sensitive microorganisms. Therapy should be guided by bacteriological studies (including sensitivity tests) and by clinical response. The following infections will usually respond to adequate dosage of Penicillin V. Streptococcal infections (without bacteremia). Mild-to-moderate infections of the upper respiratory tract, scarlet fever, and mild erysipelas. Pneumococcal infections. Mild to moderately severe infections of the respiratory tract. Staphylococcal infections—penicillin G-sensitive. Mild infections of the skin and soft tissues. Fusospirochetosis (Vincent's gingivitis and pharyngitis)—Mild to moderately severe infections of the oropharynx usually respond to therapy with oral penicillin. Launch Date 1990
Streptococcal infections 11 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2012/064071s006lbl.pdf	Curative	Approved 8429	Penicillin V Approved Use Penicillin V potassium tablets and Penicillin V potassium for oral solution are indicated in the treatment of mild to moderately severe infections due to penicillin G-sensitive microorganisms. Therapy should be guided by bacteriological studies (including sensitivity tests) and by clinical response. The following infections will usually respond to adequate dosage of Penicillin V. Streptococcal infections (without bacteremia). Mild-to-moderate infections of the upper respiratory tract, scarlet fever, and mild erysipelas. Pneumococcal infections. Mild to moderately severe infections of the respiratory tract. Staphylococcal infections—penicillin G-sensitive. Mild infections of the skin and soft tissues. Fusospirochetosis (Vincent's gingivitis and pharyngitis)—Mild to moderately severe infections of the oropharynx usually respond to therapy with oral penicillin. Launch Date 1990
Staphylococcal infections 24 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2012/064071s006lbl.pdf	Curative	Approved 8429	Penicillin V Approved Use Penicillin V potassium tablets and Penicillin V potassium for oral solution are indicated in the treatment of mild to moderately severe infections due to penicillin G-sensitive microorganisms. Therapy should be guided by bacteriological studies (including sensitivity tests) and by clinical response. The following infections will usually respond to adequate dosage of Penicillin V. Streptococcal infections (without bacteremia). Mild-to-moderate infections of the upper respiratory tract, scarlet fever, and mild erysipelas. Pneumococcal infections. Mild to moderately severe infections of the respiratory tract. Staphylococcal infections—penicillin G-sensitive. Mild infections of the skin and soft tissues. Fusospirochetosis (Vincent's gingivitis and pharyngitis)—Mild to moderately severe infections of the oropharynx usually respond to therapy with oral penicillin. Launch Date 1990

C_max

Value	Dose	Analyte	Population
15 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6811219	1 g single, oral dose: 1 g route of administration: Oral experiment type: SINGLE co-administered:	PENICILLIN V POTASSIUM serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
26.3 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6811219	2 g single, oral dose: 2 g route of administration: Oral experiment type: SINGLE co-administered:	PENICILLIN V POTASSIUM serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
35.5 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6811219	3 g single, oral dose: 3 g route of administration: Oral experiment type: SINGLE co-administered:	PENICILLIN V POTASSIUM serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
6.1 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6811219	0.4 g single, oral dose: 0.4 g route of administration: Oral experiment type: SINGLE co-administered:	PENICILLIN V POTASSIUM serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

AUC

Value	Dose	Analyte	Population
19.01 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6811219	1 g single, oral dose: 1 g route of administration: Oral experiment type: SINGLE co-administered:	PENICILLIN V POTASSIUM serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
33.36 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6811219	2 g single, oral dose: 2 g route of administration: Oral experiment type: SINGLE co-administered:	PENICILLIN V POTASSIUM serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
43.94 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6811219	3 g single, oral dose: 3 g route of administration: Oral experiment type: SINGLE co-administered:	PENICILLIN V POTASSIUM serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
6.89 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6811219	0.4 g single, oral dose: 0.4 g route of administration: Oral experiment type: SINGLE co-administered:	PENICILLIN V POTASSIUM serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

T_1/2

Value	Dose	Analyte	Population
0.78 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6811219	1 g single, oral dose: 1 g route of administration: Oral experiment type: SINGLE co-administered:	PENICILLIN V POTASSIUM serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
0.91 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6811219	2 g single, oral dose: 2 g route of administration: Oral experiment type: SINGLE co-administered:	PENICILLIN V POTASSIUM serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
1.05 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6811219	3 g single, oral dose: 3 g route of administration: Oral experiment type: SINGLE co-administered:	PENICILLIN V POTASSIUM serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
0.52 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6811219	0.4 g single, oral dose: 0.4 g route of administration: Oral experiment type: SINGLE co-administered:	PENICILLIN V POTASSIUM serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

F_unbound

Value	Dose	Co-administered	Analyte	Population
20% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/064071s006lbl.pdf	unknown, oral		PENICILLIN V POTASSIUM serum	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
10 mg/kg 4 times / day multiple, oral Recommended Dose: 10 mg/kg, 4 times / day Route: oral Route: multiple Dose: 10 mg/kg, 4 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/9006528 Page: p.48	unhealthy, 1-12 n = 216 Health Status: unhealthy Condition: Streptococcal Pharyngitis Age Group: 1-12 Sex: M+F Population Size: 216 Sources: https://pubmed.ncbi.nlm.nih.gov/9006528 Page: p.48	Disc. AE: Stomach cramps, Nausea... Other AEs: Diarrhea, Rash... AEs leading to discontinuation/dose reduction: Stomach cramps (0.46%) Nausea (0.46%) Other AEs: Diarrhea (0.8%) Rash (1.2%) Abdominal pain (0.8%) Infection (1.7%) Headache (1.2%) Vomiting (2.5%) Rhinitis (1.2%) Gastroenteritis (0.4%) Epistaxis (0.4%) Ear pain (2.1%) Cough increased (1.2%) Nausea (0.8%) Sources: https://pubmed.ncbi.nlm.nih.gov/9006528 Page: p.48
250 mg 4 times / day multiple, oral Recommended Dose: 250 mg, 4 times / day Route: oral Route: multiple Dose: 250 mg, 4 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/1656738 Page: p.3A-25S	unhealthy, 16+ n = 117 Health Status: unhealthy Condition: Streptococcal Pharyngitis Age Group: 16+ Sex: M+F Population Size: 117 Sources: https://pubmed.ncbi.nlm.nih.gov/1656738 Page: p.3A-25S	Disc. AE: Abdominal pain... AEs leading to discontinuation/dose reduction: Abdominal pain (1.7%) Sources: https://pubmed.ncbi.nlm.nih.gov/1656738 Page: p.3A-25S
590 mg 3 times / day multiple, oral Recommended Dose: 590 mg, 3 times / day Route: oral Route: multiple Dose: 590 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/11815577 Page: p.341	unhealthy, 28+/-7.9 n = 113 Health Status: unhealthy Condition: Streptococcal Pharyngitis Age Group: 28+/-7.9 Sex: M+F Population Size: 113 Sources: https://pubmed.ncbi.nlm.nih.gov/11815577 Page: p.341	Disc. AE: Nausea, Taste alteration... AEs leading to discontinuation/dose reduction: Nausea (grade 3, 0.88%) Taste alteration (grade 3, 0.88%) Sources: https://pubmed.ncbi.nlm.nih.gov/11815577 Page: p.341
800 mg 4 times / day multiple, oral Highest studied dose Dose: 800 mg, 4 times / day Route: oral Route: multiple Dose: 800 mg, 4 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/31585944	unhealthy, 30.0 (6–73) n = 212 Health Status: unhealthy Condition: Pharyngotonsillitis caused by group A streptococci Age Group: 30.0 (6–73) Sex: M+F Population Size: 212 Sources: https://pubmed.ncbi.nlm.nih.gov/31585944	Sources: https://pubmed.ncbi.nlm.nih.gov/31585944
1 g 3 times / day multiple, oral Recommended Dose: 1 g, 3 times / day Route: oral Route: multiple Dose: 1 g, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/31585944	unhealthy, 31.0 (3–67) n = 210 Health Status: unhealthy Condition: Pharyngotonsillitis caused by group A streptococci Age Group: 31.0 (3–67) Sex: M+F Population Size: 210 Sources: https://pubmed.ncbi.nlm.nih.gov/31585944	Sources: https://pubmed.ncbi.nlm.nih.gov/31585944
3 g multiple, oral Recommended Dose: 3 g Route: oral Route: multiple Dose: 3 g Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/064071s006lbl.pdf Page: p.2	unhealthy Health Status: unhealthy Condition: Prophylaxis against bacterial endocarditis Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/064071s006lbl.pdf Page: p.2	Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/064071s006lbl.pdf Page: p.2
250 mg 4 times / day multiple, oral Recommended Dose: 250 mg, 4 times / day Route: oral Route: multiple Dose: 250 mg, 4 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/1428189 Page: p.70/306	unhealthy n = 175 Health Status: unhealthy Condition: Streptococcal pharyngitis\|Streptococcal tonsillitis Sex: M+F Population Size: 175 Sources: https://pubmed.ncbi.nlm.nih.gov/1428189 Page: p.70/306	Disc. AE: Rash, Vomiting... AEs leading to discontinuation/dose reduction: Rash (0.57%) Vomiting (0.57%) Sources: https://pubmed.ncbi.nlm.nih.gov/1428189 Page: p.70/306
500 mg 4 times / day multiple, oral (max) Recommended Dose: 500 mg, 4 times / day Route: oral Route: multiple Dose: 500 mg, 4 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/064071s006lbl.pdf Page: p.2	unhealthy Health Status: unhealthy Condition: Infections due to penicillin G sensitive microorganisms Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/064071s006lbl.pdf Page: p.2	Disc. AE: Hypersensitivity reaction, Diarrhea, Clostridium difficile... AEs leading to discontinuation/dose reduction: Hypersensitivity reaction (serious\|grade 5) Diarrhea, Clostridium difficile (mild\|grade 5) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/064071s006lbl.pdf Page: p.2

AEs

Sourcing

Vendor/Aggregator	ID	URL
3B Scientific (Wuhan) Corp	3B3-053377	http://www.3bsc.com/index/pro_info.php?id=91842
AHH Chemical co.,ltd	MT-57705	http://www.ahhchemical.com/product/MT-57705.html
Alfa Chemistry	AP87081	https://reagents.alfa-chemistry.com/product/penicillin-v-cas-87-08-1-17587.html
Aurora Fine Chemicals LLC	A17.930.778	http://online.aurorafinechemicals.com/info?ID=A17.930.778
Aurora Fine Chemicals LLC	K14.717.682	http://online.aurorafinechemicals.com/info?ID=K14.717.682
Avantor Inc	101095-750	https://us.vwr.com/store/catalog/product.jsp?catalog_number=101095-750
BLD Pharm	BD290184	http://www.bldpharm.com/products/87-08-1.html
BioSynth	W-109316	https://www.biosynth.com/en/products/life-science/culture-media-additives/products/W-109316.html
Glentham Life Sciences	GA2160	http://www.glentham.com/products/product/GA2160/
Hairui	HR140122	http://www.hairuichem.com/en/product/87-08-1.html
LGC Standards	DRE-A16045500AL-100	https://www.lgcstandards.com/US/en/p/DRE-A16045500AL-100
LGC Standards	DRE-C16045500	https://www.lgcstandards.com/US/en/p/DRE-C16045500
Lab Network	LN01343665	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01343665
MuseChem	R062176	https://www.musechem.com/product/R062176.html
Sigma-Aldrich	P1000000_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/p1000000?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	1504489_USP	https://www.sigmaaldrich.com/catalog/product/usp/1504489?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Smolecule	S571986	https://www.smolecule.com/products/s571986
THE BioTek	bt-311879	https://www.thebiotek.com/product/others/bt-311879

PubMed

Title	Date	PubMed
Telithromycin.	2001	11398913
Toxic epidermal necrolysis in a patient with severe aplastic anemia treated with cyclosporin A and G-CSF.	2001	11321886
A systematic review of antistreptococcal interventions for guttate and chronic plaque psoriasis.	2001 Dec	11899140
Antioxidant vitamins improves hemoglobin level in children with group a beta hemolytic streptococcal infection.	2003 Jul	12894046
Recurrent pneumococcal meningitis in a splenectomised HIV-infected patient.	2003 Nov 7	14613586
Antibiotics for acute group A streptococcal pharyngitis.	2004 Dec	15612147
[Bite wound infections].	2004 Dec 16	15608763
Application of ion-exchange cartridge clean-up in food analysis. VI. Determination of six penicillins in bovine tissues by liquid chromatography-electrospray ionization tandem mass spectrometry.	2004 Jul 9	15296394
Community prescribing and resistant Streptococcus pneumoniae.	2005 Jun	15963276
HLA-DRB genotype and specific IgE responses in patients with allergies to penicillins.	2006 Mar 20	16584643
Comparative bioavailability study of two phenoxymethylpenicillin potassium tablet formulations in healthy volunteers.	2007 Dec	18184536
Aminopenicillin-induced exanthema allows treatment with certain cephalosporins or phenoxymethyl penicillin.	2007 Jul	17510067
Incidence of antibiotic prescribing in dental practice in Norway and its contribution to national consumption.	2007 Jun	17446241
Treatment of Lyme borreliosis.	2009	20067594
Treatment and prevention of Lyme disease.	2009	19367098
Specific IgG antibodies in sera in patients with penicillin allergy.	2009 Jun	19067119
[An exceptional component C3 deficiency revealed by serum protein electrophoresis].	2009 Nov-Dec	19939777
A prospective multi-center trial of Escherichia coli extract for the prophylactic treatment of patients with chronically recurrent cystitis.	2010 Mar	20191044
Decreased Streptococcus pneumoniae susceptibility to oral antibiotics among children in rural Vietnam: a community study.	2010 Mar 31	20356399

Patents

Sample Use Guides

In Vivo Use Guide

Usual Adult Dose for Bacterial Infection Mild to moderate infections: 125 to 500 mg orally every 6 to 8 hours

Route of Administration: Oral

In Vitro Use Guide

Penicillin V inhibited Staphylococcus aureus in human THP-1 macrophages (intracellular) with MIC90 of 0.015 mg/L

Substance Class	Chemical Created by `admin` on `Sat Dec 16 08:32:00 GMT 2023` Edited by `admin` on `Sat Dec 16 08:32:00 GMT 2023`
Record UNII	44MHH77OIC
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PENICILLIN V BENZATHINE TETRAHYDRATE

Common Name

English

BENZATHINE PHENOXYMETHYLPENICILLIN TETRAHYDRATE

Common Name

English

PHENOXYMETHYLPENICILLINE BENZATHINE TETRAHYDRATE

Common Name

English

HYDROUS PHENOXYMETHYLPENICILLIN BENZATHINE

Common Name

English

N<sup>1</sup>,N<sup>2</sup>-Dibenzylethane-1,2-diamine bis[(2S,5R,6R)-3,3-dimethyl-7-oxo-6-(2-phenoxyacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate] tetrahydrate

Common Name

English

PHENOXYMETHYLPENICILLIN (BENZATHINE) TETRAHYDRATE [EP MONOGRAPH]

Common Name

English

4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6-[(2-phenoxyacetyl)amino]-, (2S,5R,6R)-, compd. with N1,N2-bis(phenylmethyl)-1,2-ethanediamine, hydrate (2:1:4)

Systematic Name

English

PHENOXYMETHYLPENICILLIN BENZATHINE [JAN]

Common Name

English

PHENOXYMETHYLPENICILLIN (BENZATHINE) TETRAHYDRATE

Common Name

English

Code System Code Type Description

FDA UNII

44MHH77OIC