Bithionol: Difference between revisions

Jump to navigation Jump to search
VisualWikitext
No edit summary
No edit summary
Line 1: Line 1:
__NOTOC__
{{Drugbox
{{CMG}}
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 459980346
| IUPAC_name = 2,2'-sulfanediylbis(4,6-dichlorophenol)
| image = Bithionol.png
| image2 = Bithionol molecule ball.png
| alt2 = Ball-and-stick model of the bithionol molecule
| width2 = 240


==Overview==
<!--Clinical data-->
| tradename =
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_US = <!-- A / B            / C / D / X -->
| pregnancy_category = 
| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled-->
| legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C -->
| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
| legal_status = 
| routes_of_administration =


Bithionol is an [[anthelmintic]] used to treat  "[[Anoplocephala perfoliata]]" (tapeworms) in horses<ref>[http://www.ncbi.nlm.nih.gov/pubmed/19498288], Sanada Y, Senba H, Mochizuki R, et al. Evaluation of marked rise in fecal egg output after bithionol administration to horse and its application as a diagnostic marker for equine Anoplocephala perfoliata infection. J. Vet. Med. Sci. May 2009;71(5):617-620.</ref> and ''[[Fasciola hepatica]]'' (liver flukes).
<!--Pharmacokinetic data-->
| bioavailability = 
| protein_bound = 
| metabolism = 
| elimination_half-life = 
| excretion =


==Category==
<!--Identifiers-->
| CAS_number_Ref = {{cascite|changed|??}}
| CAS_number = 97-18-7
| ATC_prefix = D10
| ATC_suffix = AB01
| ATC_supplemental =  {{ATC|P02|BX01}} {{ATCvet|P52|AG07}}
| PubChem = 2406
| IUPHAR_ligand = 2338
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB04813
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = AMT77LS62O
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 290106
|  ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 2313
|  ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 3131
| smiles = Clc2cc(Cl)cc(Sc1cc(Cl)cc(Cl)c1O)c2O
|  InChI = 1/C12H6Cl4O2S/c13-5-1-7(15)11(17)9(3-5)19-10-4-6(14)2-8(16)12(10)18/h1-4,17-18H
|  InChIKey = JFIOVJDNOJYLKP-UHFFFAOYAO
|  StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C12H6Cl4O2S/c13-5-1-7(15)11(17)9(3-5)19-10-4-6(14)2-8(16)12(10)18/h1-4,17-18H
|  StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = JFIOVJDNOJYLKP-UHFFFAOYSA-N


Antiparasite
<!--Chemical data-->
| C=12 | H=6 | Cl=4 | O=2 | S=1
| molecular_weight = 356.05 g/mol
| synonyms = 2,4-dichloro- 6-(3,5-dichloro- 2-hydroxyphenyl)sulfanylphenol
}}


==Brand Names==
'''Bithionol''' is an [[anthelmintic]] used to treat ''[[Anoplocephala perfoliata]]'' (tapeworms) in horses<ref>{{ cite journal | author = Sanada Y, Senba H, Mochizuki R, Arakaki H, Gotoh T, Fukumoto S, Nagahata H | title = Evaluation of Marked Rise in Fecal Egg Output after Bithionol Administration to Horse and its Application as a Diagnostic Marker for Equine ''Anoplocephala perfoliata'' Infection | journal = Journal of Veterinary Medical Science | year = 2009 | volume = 71 | issue = 5 | pages = 617–620 | pmid = 19498288 | doi = 10.1292/jvms.71.617 | url = https://www.jstage.jst.go.jp/article/jvms/71/5/71_5_617/_pdf | format = pdf }}</ref> and ''[[Fasciola hepatica]]'' (liver flukes).


Bithionol is investigational in the U.S. The drug can be obtained from the Centers for Disease Control (CDC) Drug Service, CDC, Atlanta, Georgia 30333 (404-639-3670; evenings, weekends, or holidays: 404-639-2888).
==References==
 
{{reflist}}
==Prescribing Information==
 
====Dosage====
 
======Adult Normal Dosage======
 
'''Oral route'''
 
1) The recommended oral dose of bithionol for the treatment of Fascioliasis, and as alternative therapy in Paragonimiasis, is 30 to 50 milligrams/kilogram on alternate days for 10 to 15 doses.
 
2) Bithionol is usually given in 2 or 3 divided doses, and after meals to minimize gastrointestinal symptoms.
 
======Pediatric Normal Dosage======
 
'''Oral route'''
 
1) The recommended pediatric oral dose of bithionol for the treatment of Fascioliasis, and as alternative therapy in Paragonimiasis, is 30 to 50 milligrams/kilogram on alternate days for 10 to 15 doses.
 
2) Bithionol is usually given in 2 or 3 divided doses, and after meals to minimize gastrointestinal symptoms.
 
====Pharmacokinetics====
 
'''Onset'''
 
a) Fascioliasis, 2 to 9 days.
 
b) Resolution of fever has been reported 2 days after initiation of BITHIONOL therapy in fascioliasis, with eradication of ova in stools after 9 days.
 
c) Paragonimiasis, 3 to 5 days. (Significant improvement of hemoptysis in paragonimiasis has been reported after the third dose of oral BITHIONOL. Eradication of Paragonimus westermani ova has occurred after the fifth dose.)


'''Metabolism'''
{{Anthelmintics}}


* Metabolism Sites and Kinetics: Not extensively studied in humans. Animal studies suggest that BITHIONOL is metabolized in the liver, with metabolites being excreted in bile and urine.
[[Category:Antiparasitic agents]]
[[Category:Organochlorides]]
[[Category:Phenols]]
[[Category:Thioethers]]


====Contraindications====
* Previous [[hypersensitivity]] to BITHIONOL
====Precautions====
* Renal insufficiency (potential accumulation)
* Cardiovascular disease
* Peptic ulcer disease
* Asthma or other allergic-type disorders
====Adverse Reactions====
======Cardiovascular Effects======
* Extrasystoles, first-degree heart block, and hypertension have been reported rarely after bithionol administration.
* Blood pressure irregularities, and errors in cardiac conduction are reported in association with the therapeutic use of bithionol.
* [[Hypotension]]
======Dermatologic Effects======
* [[Photosensitivity]]
* [[Rash]]
* [[Urticaria]]
======Endocrine/Metabolic Effects======
* [[Hypoalbuminemia]]
* Increased body temperature
======Gastrointestinal Effects======
* [[Abdominal pain]]
* [[Diarrhea]]
* Loss of appetite
* [[Nausea]]
* [[Vomiting]]
======Hematologic Effects======
* [[Leukopenia]]
======Hepatic Effects======
* [[Hepatitis]]
* Increased liver enzymes
======Immunologic Effects======
* [[Anaphylaxis]]
* [[Jarisch-Herxheimer reaction]]
======Neurologic Effects======
* [[Dizziness]]
* [[Headache]]
======Respiratory Effects======
* [[Cough]]
* [[Respiratory distress]]
* [[Tachypnea]]
* [[Wheezing]]
======Other======
* [[Angioedema]]
====Therapeutic Uses====
* Infection by Fasciola (non-FDA approval)
* Infection by Paragonimus (non-FDA approval)
==Mechanism of Action==
Bithionol is a chlorinated phenol derivative which has antimicrobial and anthelmintic activity by uncoupling oxidative phosphorylation in the parasite, leading to blockade of adenosine triphosphate synthesis and energy production.
==References==
{{Reflist|2}}


[[Category:Antibiotics]]
{{antiinfective-drug-stub}}
[[Category:Drug]]
{{dermatologic-drug-stub}}

Revision as of 18:13, 13 April 2015

Bithionol
Ball-and-stick model of the bithionol molecule
Clinical data
Synonyms2,4-dichloro- 6-(3,5-dichloro- 2-hydroxyphenyl)sulfanylphenol
ATC code
Identifiers
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
ChEBI
ChEMBL
E number{{#property:P628}}
ECHA InfoCard{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
FormulaC12H6Cl4O2S
Molar mass356.05 g/mol
3D model (JSmol)
 ☒N☑Y (what is this?)  (verify)

Bithionol is an anthelmintic used to treat Anoplocephala perfoliata (tapeworms) in horses[1] and Fasciola hepatica (liver flukes).

References

  1. ↑ Sanada Y, Senba H, Mochizuki R, Arakaki H, Gotoh T, Fukumoto S, Nagahata H (2009). "Evaluation of Marked Rise in Fecal Egg Output after Bithionol Administration to Horse and its Application as a Diagnostic Marker for Equine Anoplocephala perfoliata Infection" (pdf). Journal of Veterinary Medical Science. 71 (5): 617–620. doi:10.1292/jvms.71.617. PMID 19498288.

Template:Anthelmintics


Template:Antiinfective-drug-stub Template:Dermatologic-drug-stub

Retrieved from "https://www.wikidoc.org/index.php?title=Bithionol&oldid=1086942"