Identification
- Generic Name
- Iodoform
- DrugBank Accession Number
- DB13813
- Background
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.
- Type
- Small Molecule
- Groups
- Approved, Experimental, Vet approved
- Structure
Structure for Iodoform (DB13813)
- Weight
- Average: 393.732
Monoisotopic: 393.72124 - Chemical Formula
- CHI3
- Synonyms
- carbon triiodide
- Iodoform
- Jodoform
- methyl triiodide
- triiodomethane
Pharmacology
- Indication
No approved therapeutic indications.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- 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 [L2646].
- Volume of distribution
No pharmacokinetic data available.
- Protein binding
No pharmacokinetic data available.
- Metabolism
It is expected to be oxidized to iodine [L2646].
Hover over products below to view reaction partners
- Route of elimination
No pharmacokinetic data available.
- Half-life
No pharmacokinetic data available.
- Clearance
No pharmacokinetic data available.
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
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 [L2646]. While there is no known antidote for iodoform overdose, supportive and symptomatic treatment is highly recommended [L2646].
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 [L2646]. 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.
- 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
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Curity 3% Iodoform Packing Strip Dressing 3 % Topical Tyco Healthcare 1996-12-31 2010-08-05 Canada 
Iodoform Nugauze Packing Strip 5% Dressing 5 % Topical Johnson & Johnson Medical Products 1992-12-31 2003-08-13 Canada Iodoform Packing Strip Strip 5 % Topical Derma Sciences Inc 2005-03-03 2019-02-08 Canada Iodoform Packing Strip 5% W/w Strip 5 % Topical Dumex Medical Canada Inc. 2002-03-11 2005-08-09 Canada
Categories
- ATC Codes
- D09AA13 — Iodoform
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- 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
- Aliphatic acyclic compound / Alkyl iodide / Hydrocarbon derivative / Organoiodide / Trihalomethane
- Molecular Framework
- Aliphatic acyclic compounds
- External Descriptors
- one-carbon compound, iodomethanes (CHEBI:37758)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- KXI2J76489
- CAS number
- 75-47-8
- InChI Key
- OKJPEAGHQZHRQV-UHFFFAOYSA-N
- InChI
- InChI=1S/CHI3/c2-1(3)4/h1H
- IUPAC Name
- triiodomethane
- SMILES
- [H]C(I)(I)I
References
- General References
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- Iodoform MSDS Thermofisher [Link]
- External Links
- Human Metabolome Database
- HMDB0253528
- KEGG Drug
- D01910
- KEGG Compound
- C13383
- PubChem Compound
- 6374
- PubChem Substance
- 347829319
- ChemSpider
- 6134
- 27748
- ChEBI
- 37758
- ChEMBL
- CHEMBL1451116
- ZINC
- ZINC000006827595
- Wikipedia
- Iodoform
- MSDS
- Download (46.8 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Treatment Necrotic Pulp / Postoperative pain 1 4 Unknown Status Prevention Alveoli, Teeth; Inflammation / Alveolitis of Jaw / Dry socket syndrome / Impacted Third Molar Tooth 1 3 Completed Treatment Dental Pulp Cavity 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Dressing Topical 3 % Dressing Topical 5 % Strip Topical 5 % - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 119-122 MSDS boiling point (°C) 218 MSDS water solubility Slightly soluble MSDS - Predicted Properties
Property Value Source Water Solubility 0.143 mg/mL ALOGPS logP 2.82 ALOGPS logP 4.65 Chemaxon logS -3.4 ALOGPS Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 0 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 0 Å2 Chemaxon Rotatable Bond Count 0 Chemaxon Refractivity 45.24 m3·mol-1 Chemaxon Polarizability 17.59 Å3 Chemaxon Number of Rings 0 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0006-0009000000-a5df96beb25d12f7be6a Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0006-0009000000-19ab66d24bb02d3f5bfb Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0006-0009000000-19ab66d24bb02d3f5bfb Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0006-0029000000-0c6b744089106099df84 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0006-0009000000-19ab66d24bb02d3f5bfb Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-014i-0090000000-5479a3233295b1756fa6 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 141.15608 predictedDeepCCS 1.0 (2019) [M+H]+ 143.75652 predictedDeepCCS 1.0 (2019) [M+Na]+ 152.63766 predictedDeepCCS 1.0 (2019)
Drug created at June 23, 2017 20:49 / Updated at April 18, 2024 09:15