Iodoform

Identification

Name
Iodoform
Accession Number
DB13813
Type
Small Molecule
Groups
Approved, Experimental, Vet approved
Description

Iodoform is an organoiodine compound with the formula CHI3 and a tetrahedral molecular geometry. It is a relatively water-insoluble yellow solid that is chemically reactive in free-radical reactions [1]. Due to its antimicrobial properties following topical administration, minimal levels of iodoform may be found in disinfectants and it is more primarily used for veterinary purposes. Iodoform has also been found in dental paste and root canal filling materials in combination with other intracanal medications due to its radiopacity [2]. Since the beginning of the 20th century, iodoform has been commonly used as a healing and antiseptic dressing or powder for wounds and sores, however such clinical use to this date is limited. Iodoform is soluble in fatty acids and decomposes releasing iodine in nascent state (96,7% of iodine) when in contact with secretions or endodontic infections [2].

Structure
Thumb
Synonyms
  • carbon triiodide
  • Jodoform
  • methyl triiodide
  • triiodomethane
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Curity 3% Iodoform Packing StripDressing3 %TopicalTyco Healthcare1996-12-312010-08-05Canada
Iodoform Nugauze Packing Strip 5%Dressing5 %TopicalJohnson & Johnson Medical Products1992-12-312003-08-13Canada
Iodoform Packing StripStrip5 %TopicalDerma Sciences Inc2005-03-03Not applicableCanada
Iodoform Packing Strip 5% W/wStrip5 %TopicalDumex Medical Canada Inc.2002-03-112005-08-09Canada
Categories
UNII
KXI2J76489
CAS number
75-47-8
Weight
Average: 393.732
Monoisotopic: 393.72124
Chemical Formula
CHI3
InChI Key
OKJPEAGHQZHRQV-UHFFFAOYSA-N
InChI
InChI=1S/CHI3/c2-1(3)4/h1H
IUPAC Name
triiodomethane
SMILES
[H]C(I)(I)I

Pharmacology

Indication

No approved therapeutic indications.

Pharmacodynamics

Iodoform exhibits antibacterial activities after topical application. In a comparative study of wound dressing agents, iodoform gauze exerted an antibacterial effect 3 hours after the start of bacterial growth of E. coli and subsequently maintained the strong antibacterial effectiveness [5]. A study demonstrated that direct and indirect exposure to high concentrations of iodoform induces a cytotoxic effect on cultures of macrophages and epithelial cells in vitro, while cell proliferation was enhanced at low concentrations of iodoform [4]. This cytotoxic effect of iodoform in root canals may further lead to long-term local irritation to follicles of permanent successors and formation of cyst-like radiolucent defects [4].

Mechanism of action

While the mechanism of action of iodoform remains unclear, it is proposed that iodoform releases iodine, which denatures bacterial proteins by oxidation of the free iodine [5]. Iodoform may also play a role in chemical debridement for effective necrotic wound healing and tissue damage repair via collagen fibrinolysis; upon treatment in necrotic tissue, iodoform reduced the size of the macromolecules containing collagen I in wound surface proteins [3]. In human gingival fibroblasts in vitro, high concentrations of iodoform was shown to decrease the viability of macrophages and epithelial cells and reduced the secretion of P. gingivalis-induced TNFα [4]. P. gingivalis is an anaerobic bacteria present in anaerobic oral niches including periapical sites and periodontal pockets [4].

Absorption

Iodoform is reported to be absorbed through denuded skin, wounds or mucous membranes [6].

Volume of distribution

No pharmacokinetic data available.

Protein binding

No pharmacokinetic data available.

Metabolism

It is expected to be oxidized to iodine [6].

Route of elimination

No pharmacokinetic data available.

Half life

No pharmacokinetic data available.

Clearance

No pharmacokinetic data available.

Toxicity

Oral LD50, dermal LD50, and inhalation LC50 in rat are 355 mg/kg, 1184 mg/kg, and 165 ppm/7h, respectively [MSDS]. Fatal dose of iodoform in humans is estimated to be 2 g [6]. Systemic intoxication and severe poisoning, mostly characterized by dermatitis, headache, somnolence, delirium, hallucinations, consciousness disturbances, coma, vomiting, CNS depression, tachycardia, and rapid feeble pulse, may result from excess absorption through wounds and abscesses, or ingestion of large quantities [6]. While there is no known antidote for iodoform overdose, supportive and symptomatic treatment is highly recommended [6].

Hepatocellular damage has been observed with iodoform toxicity, where production of both fatty liver and necrosis was seen, as well as lesions of liver membranous cellular components [6]. Iodoform induces hepatocellular injury and hepatic lesions in a similar manner to carbon tetrachloride, where cellular membranes may possibly be primary sites of action [1].

Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
  1. Sell DA, Reynolds ES: Liver parenchymal cell injury. 8. Lesions of membranous cellular components following iodoform. J Cell Biol. 1969 Jun;41(3):736-52. [PubMed:5768872]
  2. Estrela C, Estrela CR, Hollanda AC, Decurcio Dde A, Pecora JD: Influence of iodoform on antimicrobial potential of calcium hydroxide. J Appl Oral Sci. 2006 Jan;14(1):33-7. [PubMed:19089027]
  3. Mizokami F, Murasawa Y, Furuta K, Isogai Z: Iodoform gauze removes necrotic tissue from pressure ulcer wounds by fibrinolytic activity. Biol Pharm Bull. 2012;35(7):1048-53. [PubMed:22791151]
  4. Petel R, Moskovitz M, Tickotsky N, Halabi A, Goldstein J, Houri-Haddad Y: Cytotoxicity and proliferative effects of Iodoform-containing root canal-filling material on RAW 264.7 macrophage and RKO epithelial cell lines. Arch Oral Biol. 2013 Jan;58(1):75-81. doi: 10.1016/j.archoralbio.2012.06.014. Epub 2012 Nov 1. [PubMed:23123069]
  5. Fujiwara T, Hosokawa K, Kubo T: Comparative study of antibacterial effects and bacterial retentivity of wound dressings. Eplasty. 2013;13:e5. Epub 2013 Jan 24. [PubMed:23372860]
  6. IODOFORM - National Library of Medicine HSDB Database - Toxnet - NIH [Link]
External Links
KEGG Drug
D01910
KEGG Compound
C13383
PubChem Compound
6374
PubChem Substance
347829319
ChemSpider
6134
ChEBI
37758
ChEMBL
CHEMBL1451116
Wikipedia
Iodoform
ATC Codes
D09AA13 — Iodoform
AHFS Codes
  • 84:04.92 — Miscellaneous Local Anti-infectives
MSDS
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Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4RecruitingPreventionAlveoli, Teeth; Inflammation / Alveolitis of Jaw / Dry socket syndrome / Impacted Third Molar Tooth1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
DressingTopical3 %
DressingTopical5 %
StripTopical5 %
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)119-122MSDS
boiling point (°C)218MSDS
water solubilitySlightly solubleMSDS
Predicted Properties
PropertyValueSource
Water Solubility0.143 mg/mLALOGPS
logP2.82ALOGPS
logP4.65ChemAxon
logS-3.4ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity45.24 m3·mol-1ChemAxon
Polarizability17.59 Å3ChemAxon
Number of Rings0ChemAxon
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 MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as trihalomethanes. These are organic compounds in which exactly three of the four hydrogen atoms of methane (CH4) are replaced by halogen atoms.
Kingdom
Organic compounds
Super Class
Organohalogen compounds
Class
Alkyl halides
Sub Class
Halomethanes
Direct Parent
Trihalomethanes
Alternative Parents
Organoiodides / Hydrocarbon derivatives / Alkyl iodides
Substituents
Trihalomethane / Hydrocarbon derivative / Organoiodide / Alkyl iodide / Aliphatic acyclic compound
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
one-carbon compound, iodomethanes (CHEBI:37758)

Drug created on June 23, 2017 14:49 / Updated on November 20, 2018 01:01