NAV

Dithiazanine

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Generic Name
Dithiazanine
DrugBank Accession Number
DB11516
Background

Dithiazanine is a highly potent anthelmintic, introduced in 1959 for the treatment of strongyloid worms and whipworms. However, its use is severely limited due to its toxicity. Dithiazanine iodide was associated with eight fatal cases of severe acidosis and shock between 1961 and 1964. Dithiazanine iodide has been withdrawn from the market in countries such as France in Italy, but it may remain available in others.11,12

Type
Small Molecule
Groups
Vet approved, Withdrawn
Structure
3D
Similar Structures
Weight
Average: 391.57
Monoisotopic: 391.129717517
Chemical Formula
C23H23N2S2
Synonyms
  • 3,3'-Diethylthiadicarbocyanine
  • Dithiazaninum
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
Not Available
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Dithiazanine iodide8OEC3RA07X514-73-8MNQDKWZEUULFPX-UHFFFAOYSA-M

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as benzothiazoles. These are organic compounds containing a benzene fused to a thiazole ring (a five-membered ring with four carbon atoms, one nitrogen atom and one sulfur atom).
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Benzothiazoles
Sub Class
Not Available
Direct Parent
Benzothiazoles
Alternative Parents
Aryl thioethers / Benzenoids / Thiazoles / Heteroaromatic compounds / Ketene acetals / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds / Hydrocarbon derivatives / Organic cations
Substituents
1,2-benzothiazole / 1,3-benzothiazole / Aromatic heteropolycyclic compound / Aryl thioether / Azacycle / Azole / Benzenoid / Benzo-thiazole / Heteroaromatic compound / Hydrocarbon derivative
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
benzothiazoles, benzothiazolium ion (CHEBI:52787)
Affected organisms
Not Available

Chemical Identifiers

UNII
5L7E7IY5EH
CAS number
7187-55-5
InChI Key
FYXWDSGGZAMYFZ-UHFFFAOYSA-N
InChI
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
IUPAC Name
3-ethyl-2-[5-(3-ethyl-2,3-dihydro-1,3-benzothiazol-2-ylidene)penta-1,3-dien-1-yl]-1,3-benzothiazol-3-ium
SMILES
[H]C(C([H])=C([H])C1=[N+](CC)C2=CC=CC=C2S1)=C([H])C([H])=C1SC2=C(C=CC=C2)N1CC

References

General References
  1. GARAGUSO P: [Dithiazanine and Hymenolepis nana]. Sem Med. 1962 Jan 4;120:53-60. [Article]
  2. VINKE B, van der SAR: Dithiazanine, a new anthelminthic. Trop Geogr Med. 1959 Dec;11:335-8. [Article]
  3. CERF J: [Dithiazanine therapy of strongyloidosis]. Ann Soc Belg Med Trop (1920). 1958 Dec 31;38(6):1027-30. [Article]
  4. GARAGUSO P: [Dithiazanine and Enterobius vermicularis]. Sem Med. 1961 Nov 23;119:1803-14. [Article]
  5. GARAGUSO P: [Dithiazanine and Ancylostoma or Necator]. Sem Med. 1961 Dec 11;119:2016-21. [Article]
  6. MUHLEISEN JP, SWARTZWELDER JC: Therapy of strongyloidiasis with dithiazanine. Am J Gastroenterol. 1959 Sep;32:317-27. [Article]
  7. BASNUEVO JG, KOURI A: [Anthelmintic action of dithiazanine iodide]. Rev Kuba Med Trop Parasitol. 1959 Jul-Dec;15:27-36. [Article]
  8. MILLER JH, ANTHONY SO, SWARTZWELDER JC, FRYE WW, LAMPERT R: Treatment of enterobiasis with dithiazanine. Am J Dig Dis. 1958 Mar;3(3):229-31. [Article]
  9. LIMA JP, PALOMBINI BC, TANNHAUSER SL: [Dithiazanine in treatment of strongyloidiasis]. Rev Bras Med. 1960 Feb;17:123-6. [Article]
  10. RODRIGUEZDECURET H, DELPILARALIAGA M: DITHIAZANINE INTOXICATION, A CASE REPORT. Bol Asoc Med P R. 1963 Nov;55:469-73. [Article]
  11. Garmaise DL, Chambers CH, Komlossy J, McCrae RC: Anthelmintic quaternary salts. Thiacyanines and hemithiacyanines. J Med Chem. 1967 Sep;10(5):897-9. doi: 10.1021/jm00317a031. [Article]
  12. WHO: Consolidated list of products whose consumption and/or sale have been banned, withdrawn, severely restricted or not approved by governments [Link]
ChemSpider
10134
BindingDB
47714
ChEBI
52787
ChEMBL
CHEMBL1185568
ZINC
ZINC000001628132

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00028 mg/mLALOGPS
logP2.42ALOGPS
logP2.52Chemaxon
logS-6.2ALOGPS
pKa (Strongest Basic)-2Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count1Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area7.12 Å2Chemaxon
Rotatable Bond Count5Chemaxon
Refractivity142.44 m3·mol-1Chemaxon
Polarizability45.11 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-221.5738331
predicted
DarkChem Lite v0.1.0
[M-H]-180.88376
predicted
DeepCCS 1.0 (2019)
[M+H]+221.3356331
predicted
DarkChem Lite v0.1.0
[M+H]+183.24178
predicted
DeepCCS 1.0 (2019)
[M+Na]+220.9876331
predicted
DarkChem Lite v0.1.0
[M+Na]+190.44623
predicted
DeepCCS 1.0 (2019)

Drug created at February 26, 2016 17:31 / Updated at November 18, 2022 07:07