BENZATHINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C16H20N2
Molecular Weight	240.3434
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C(CNCC1=CC=CC=C1)NCC2=CC=CC=C2

InChI

InChIKey=JUHORIMYRDESRB-UHFFFAOYSA-N

InChI=1S/C16H20N2/c1-3-7-15(8-4-1)13-17-11-12-18-14-16-9-5-2-6-10-16/h1-10,17-18H,11-14H2

HIDE SMILES / InChI

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24177358
Curator's Comment: description was created based on several sources, including https://www.drugs.com/dosage/penicillin-g-benzathine.html | https://www.google.com/patents/WO2013184202A1

Benzathine is a diamine used as a component in some medications including benzathine phenoxymethylpenicillin and benzathine benzylpenicillin. Benzathine stabilises penicillin and prolongs its sojourn when injected into tissues. Benzathine have some hepatitis C virus inhibitorion activity in in vitro assay

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
F-box only protein 3 3 Target ID: Q9UK99 Gene ID: 26273.0 Gene Symbol: FBXO3 Target Organism: Homo sapiens (Human) Sources: https://www.google.com/patents/WO2013184202A1	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Hepatitis C 42 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24177358	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
[Plaques opalines: a rare form of secondary syphilis of the oral mucous membrane].	2006-06	15995867
Azithromycin versus penicillin for early syphilis.	2006-01-12	16411293
Azithromycin versus penicillin for early syphilis.	2006-01-12	16411292
Case records of the Massachusetts General Hospital. Case 39-2005. A 63-year-old woman with a positive serologic test for syphilis and persistent eosinophilia.	2005-12-22	16371636
Colchicine and benzathine penicillin in the treatment of Behçet disease: a case comparative study.	2005-12-01	16409899
Assessment of a register-based rheumatic heart disease secondary prevention program in an Australian Aboriginal community.	2005-12	16366062
Ocular manifestations and treatment of syphilis.	2005-11-12	16282150
[Disseminated maculopapular rash in a patient with AIDS].	2005-11	16324571
A case of primary syphilis in the rectum.	2005-10	16224168
Successful treatment of refractory thrombocytopenia with mycophenolate mofetil in a patient with systemic lupus erythematosus.	2005-10	16224167
Azithromycin versus penicillin G benzathine for early syphilis.	2005-09-22	16177256
Single-dose azithromycin versus penicillin G benzathine for the treatment of early syphilis.	2005-09-22	16177249
Antenatal syphilis screening in sub-Saharan Africa: lessons learned from Tanzania.	2005-09	16135202
Is it possible to prevent rheumatic fever.	2005-07-15	16013365
Acute severe mitral regurgitation during first attacks of rheumatic fever: clinical spectrum, mechanisms and prognostic factors.	2005-07	16116868
Infection with Leishmania infantum Inhibits actinomycin D-induced apoptosis of human monocytic cell line U-937.	2005-06-02	15926996
The effectiveness of long-acting penicillin (penidur) in preventing recurrences of dermatolymphangioadenitis(DLA) and controlling skin, deep tissues, and lymph bacterial flora in patients with "filarial" lymphedema.	2005-06	16184816
FDA strengthens labeling for long-acting penicillins.	2005-06	16034731
Extensive annular verrucous late secondary syphilis.	2005-06	15949006
Treatment for syphilis in antenatal care: compliance with the three dose standard treatment regimen.	2005-06	15923289
With this eruption, there is not a second to lues.	2005-05-14	15891256
[The unusual wandering of lues. Did the patient infect himself by tongue kissing?].	2005-05-05	15934581
Synthesis and antimycobacterial activity of ferrocenyl ethambutol analogues and ferrocenyl diamines.	2005-05-02	15837313
Efficacy of intramuscular penicillin in the eradication of group B streptococcal colonization at delivery.	2005-05	16147846
Long-term use of penicillin for the treatment of chronic plaque psoriasis.	2005-04-20	16172045
Effect of testosterone replacement or duration of castration on baroreflex bradycardia in conscious rats.	2005-03-30	15799780
[Hoigne's syndrome].	2005-03-22	15777526
Inadvertent use of Bicillin C-R to treat syphilis infection--Los Angeles, California, 1999-2004.	2005-03-11	15758893
Misclassification of the stages of syphilis: implications for surveillance.	2005-03	15729150
[A painful swelling of the tongue].	2005-02	15748001
Scleredema adultorum associated with hyperkeratosis.	2005-01-22	15660895
Ionic liquids as advantageous solvents for headspace gas chromatography of compounds with low vapor pressure.	2005-01-15	15649075
Evaluation of syphilis in patients with HIV infection in Nigeria.	2005-01	15655014
Effectiveness of syphilis treatment using azithromycin and/or benzathine penicillin in Rakai, Uganda.	2005-01	15614114
Pustulocrustaceous secondary syphilis.	2005	16191874
Syphilis and HIV: a review for clinicians as this centuries-old disease makes a comeback.	2005	16124106
Syphilis surveillance in France, 2000-2003.	2004-12	15677855
[Sydenham's chorea. A clinical analysis of 55 patients with a prolonged follow-up].	2004-11-16	15543494
Treatment of maternal syphilis in rural South Africa: effect of multiple doses of benzathine penicillin on pregnancy loss.	2004-11	15548319
[Current syphilis therapies and serological control. Commentary on the article by M. Hartmann in Hautarzt, Volume 2 (2004)].	2004-11	15448930
[Syphilis with HIV coinfection].	2004-10	16281586
Syphilis in the HIV-infected patient: an update on epidemiology, diagnosis, and management.	2004-09	16091235
Investigation of DNA damage in lymphocytes exposed to benzathine penicillin G.	2004-08	15310305
Macrolide resistance in Treponema pallidum in the United States and Ireland.	2004-07-08	15247355
Syphilis control--a continuing challenge.	2004-07-08	15247352
Maternal syphilis: pathophysiology and treatment.	2004-06	15356936
Benzathine penicillin formulations.	2004-06	15194852
[Medicine hypersensitivity--case report].	2004-04	15517938
Western blotting as the confirmatory test for syphilis in a patient with systemic lupus erythematosus.	2004-04	15096386
Relapse of secondary syphilis after benzathine penicillin G: molecular analysis.	2004-03	15076935

Patents

Sample Use Guides

In Vivo Use Guide

0.72g (1.2 million units) IM as a single dose as Benzathine benzylpenicillin. 0.72g Benzathine benzylpenicillin contains 0.19g of Benzathine and 0.53g of benzylpenicillin

Route of Administration: Intramuscular

In Vitro Use Guide

Huh-7 replicon cells were plated at 2000 cells/well in 40 mkL of culture media in 384-well plates. After overnight incubation, serially diluted BENZATHINE in 20 mkL of cell culture media were added. At 72 h post BENZATHINE treatment, plates with GFP expressing replicon cell lines were fixed with 2% paraformaldehyde (PFA) and applied for nuclei staining with 10 mkg/mL of Hoechst 33342 (Sigma Aldrich). Cells were visualized by fully automated confocal microscopy (Opera, PerkinElmer) and analyzed by in-house software. HCV RNA replication was measured by GFP expression and cytotoxicity was measured by nucleus counting.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 21:09:31 GMT 2025` Edited by `admin` on `Mon Mar 31 21:09:31 GMT 2025`
Record UNII	C659VZ7P7T
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NSC-5632

Preferred Name

English

BENZATHINE

Common Name

English

1,2-BIS(BENZYLAMINO)ETHANE

Systematic Name

English

N,N'-DIBENZYLETHYLENEDIAMINE

Systematic Name

English

N,N'-DIBENZYL-1,2-ETHYLENEDIAMINE

Systematic Name

English

BENZATHINE [MI]

Common Name

English

N,N'-DIBENZYL-1,2-DIAMINOETHANE

Systematic Name

English

N1,N2-BIS(PHENYLMETHYL)-1,2-ETHANEDIAMINE

Systematic Name

English

NSC-62936

Code

English

BENZATIN

Common Name

English

DBED

Common Name

English

Code System Code Type Description

FDA UNII

C659VZ7P7T