DITHIAZANINE

US Previously Marketed

First approved in 1958

Details

Stereochemistry	ACHIRAL
Molecular Formula	C23H23N2S2
Molecular Weight	391.572
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	3
Charge	1

SHOW SMILES / InChI

Structure Search

SMILES

CCN1\C(SC2=C1C=CC=C2)=C/C=C/C=C/C3=[N+](CC)C4=CC=CC=C4S3

InChI

InChIKey=FYXWDSGGZAMYFZ-UHFFFAOYSA-N

InChI=1S/C23H23N2S2/c1-3-24-18-12-8-10-14-20(18)26-22(24)16-6-5-7-17-23-25(4-2)19-13-9-11-15-21(19)27-23/h5-17H,3-4H2,1-2H3/q+1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/13480859 | https://www.drugs.com/international/dithiazanine-iodide.html | https://www.gpo.gov/fdsys/pkg/CFR-2010-title21-vol6/pdf/CFR-2010-title21-vol6-sec520-763a.pdf

Dithiazanine, 3-ethyl-2-[5-(3-ethyl-2-benzothiazolinylidene)-l, 3- pentadienyl] benzothiazolium iodide, is an old effective broad-spectrum human anthelmintic. In proper dosage, this polyvermicide is therapeutic for trichuriasis, strongyloidiasis, ascariasis, and enterobiasis. The drug also has significant anthelmintic activity against human hookworm, Necator americanus. It fulfills a need for an effective therapeutic for trichuriasis and strongyloidiasis. Dithiazanine is useful for the treatment of patients with either single or multiple intestinal helminth infections. It is effective for mass therapy for trichuriasis. Nowdays Dithiazanine is used only as a veterinary anthelmintic for dogs. It has being proved to be a highly toxic chemical, with a lethal dose for humans of about 4–16 mg/kg by oral ingestion.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Trichuris Trichiura 2 Target ID: Trichuris Trichiura Sources: https://www.ncbi.nlm.nih.gov/pubmed/13480859 \| https://www.ncbi.nlm.nih.gov/pubmed/13873447 \| https://www.ncbi.nlm.nih.gov/pubmed/13593925	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Worm infection 4 Sources: https://www.gpo.gov/fdsys/pkg/CFR-2010-title21-vol6/pdf/CFR-2010-title21-vol6-sec520-763a.pdf https://www.law.cornell.edu/cfr/text/21/520.763a	Curative		Approved 8429	Dithiazanine iodide Approved Use Use for treating dogs for large roundworms, hookworms, whipworms, and strongyloides
Worm infection 4 Sources: https://www.ncbi.nlm.nih.gov/pubmed/13480859 https://www.ncbi.nlm.nih.gov/pubmed/13873447	Curative		Approved 8429	Delvex Approved Use Helminth (worm) infections

Doses

Dose	Population	Adverse events
300 mg 3 times / day multiple, oral Highest studied dose Dose: 300 mg, 3 times / day Route: oral Route: multiple Dose: 300 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/13595202/	unhealthy n = 73 Health Status: unhealthy Condition: Helminthiasis Sex: M+F Population Size: 73 Sources: https://pubmed.ncbi.nlm.nih.gov/13595202/	Disc. AE: Nausea... AEs leading to discontinuation/dose reduction: Nausea (1.37%) Sources: https://pubmed.ncbi.nlm.nih.gov/13595202/
200 mg 3 times / day multiple, oral Studied dose Dose: 200 mg, 3 times / day Route: oral Route: multiple Dose: 200 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/13722979	unhealthy n = 35 Health Status: unhealthy Condition: Helminthiasis Population Size: 35 Sources: https://pubmed.ncbi.nlm.nih.gov/13722979	Disc. AE: Vomiting... AEs leading to discontinuation/dose reduction: Vomiting (severe, 11.43%) Sources: https://pubmed.ncbi.nlm.nih.gov/13722979

AEs

AE	Significance	Dose	Population
Nausea	1.37% Disc. AE	300 mg 3 times / day multiple, oral Highest studied dose Dose: 300 mg, 3 times / day Route: oral Route: multiple Dose: 300 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/13595202/	unhealthy n = 73 Health Status: unhealthy Condition: Helminthiasis Sex: M+F Population Size: 73 Sources: https://pubmed.ncbi.nlm.nih.gov/13595202/
Vomiting	severe, 11.43% Disc. AE	200 mg 3 times / day multiple, oral Studied dose Dose: 200 mg, 3 times / day Route: oral Route: multiple Dose: 200 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/13722979	unhealthy n = 35 Health Status: unhealthy Condition: Helminthiasis Population Size: 35 Sources: https://pubmed.ncbi.nlm.nih.gov/13722979

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:52787	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:52787
ZINC	ZINC000001628132	http://zinc15.docking.org/substances/ZINC000001628132
eMolecules	4422465	https://www.emolecules.com/cgi-bin/more?vid=4422465

PubMed

Title	Date	PubMed
Dithiazanine, an effective broad-spectrum anthelmintic; results of therapy of trichuriasis, strongyloidiasis, enterobiasis, ascariasis, and hookworm infection.	1957 Dec 21	13480859
[In Vitro Activities Of Various Drugs Against Adult Worms Of Clonorchis Sinensis].	1980 Dec	12902729
The effect of non-immune stresses on the development of Strongyloides ratti.	2005 Sep	16178360
Highly penetrative, drug-loaded nanocarriers improve treatment of glioblastoma.	2013 Jul 16	23818631

Patents

Sample Use Guides

In Vivo Use Guide

Trichuriasis in 164 patients was treated with doses of 200 mg. thrice daily; this dosage, continued for five days, cured 97% of the patients. Ascariasis was treated in 42 persons with up to 600 mg. daily in divided doses. There was a 97% reduction in the egg-count of these patients, and 28 of them showed complete elimination of the infection. Strongyloidiasis was eliminated in 16 out of a group of 18 patients treated for 5 to 21 days. Enterobiasis was treated in 35 boys under conditions showing that 100 mg. of dithiazanine thrice daily for five days sufficed for cure in all cases.

Route of Administration: Oral

In Vitro Use Guide

Moderate in vitro activity against adult worms of Clororchis sinensis was observed in the concentrations of 1.0 and 0.1 ug/ml of gentian dithiazanine.

Name

Type

Language

DITHIAZANINE

Common Name

English

Dithiazanine [WHO-DD]

Common Name

English

DITHIAZANINE ION

Common Name

English

3-ETHYL-2-(5-(3-ETHYL-2-BENZOTHIAZOLINYLIDENE)-1,3-PENTADIENYL)BENZOTHIAZOLIUM

Systematic Name

English

DITHIAZANINE CATION

Common Name

English

Classification Tree Code System Code

CFR

21 CFR 520.763B