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Tox21_202389
Also known as: Triiodomethane, 75-47-8, Methane, triiodo-, Carbon triiodide, Jodoform, Chi3
Molecular Formula
CHI3
Molecular Weight
393.732  g/mol
InChI Key
OKJPEAGHQZHRQV-UHFFFAOYSA-N
FDA UNII
KXI2J76489

iodoform is a natural product found in Asparagopsis taxiformis with data available.
1 2D Structure

Tox21_202389

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
iodoform
2.1.2 InChI
InChI=1S/CHI3/c2-1(3)4/h1H
2.1.3 InChI Key
OKJPEAGHQZHRQV-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C(I)(I)I
2.2 Other Identifiers
2.2.1 UNII
KXI2J76489
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Tri-iodomethane

2.3.2 Depositor-Supplied Synonyms

1. Triiodomethane

2. 75-47-8

3. Methane, Triiodo-

4. Carbon Triiodide

5. Jodoform

6. Chi3

7. Trijodmethane

8. Nci-c04568

9. Iodoformum

10. Nsc-26251

11. Chebi:37758

12. Kxi2j76489

13. Ncgc00091389-01

14. Dsstox_cid_743

15. Dezinfekt V

16. Dsstox_rid_75765

17. Jodoform [czech]

18. Dsstox_gsid_20743

19. Iodoform [jan]

20. Trijodmethane [czech]

21. Cas-75-47-8

22. Ccris 346

23. Hsdb 4099

24. Iodoform [usp:jan]

25. Einecs 200-874-5

26. Nsc 26251

27. Unii-kxi2j76489

28. Methyl Triiodide

29. Ai3-52396

30. Iodoform (tn)

31. Tris(iodanyl)methane

32. Mfcd00001069

33. Iodoform, 99%

34. Iodoform [hsdb]

35. Iodoform [inci]

36. Iodoform [mi]

37. Wln: Iyii

38. Iodoformum [hpus]

39. Iodoform (jp17/usp)

40. Iodoform [mart.]

41. Iodoform [who-dd]

42. Iodoform, Saj First Grade

43. Chembl1451116

44. Dtxsid4020743

45. Iodoform [usp Monograph]

46. Nsc26251

47. Zinc6827595

48. Tox21_111124

49. Tox21_202389

50. Tox21_302774

51. Akos009031506

52. Iodoform, Purum, >=99.0% (at)

53. Db13813

54. Iodoform, Puriss., 99.0-100.5%

55. S12111

56. Ncgc00091389-02

57. Ncgc00091389-03

58. Ncgc00256394-01

59. Ncgc00259938-01

60. As-14199

61. Ft-0627266

62. D01910

63. A838427

64. Q412393

65. J-650249

2.4 Create Date
2005-03-26
3 Chemical and Physical Properties
Molecular Weight 393.732 g/mol
Molecular Formula CHI3
XLogP32.7
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count0
Rotatable Bond Count0
Exact Mass393.7212 g/mol
Monoisotopic Mass393.7212 g/mol
Topological Polar Surface Area0 Ų
Heavy Atom Count4
Formal Charge0
Complexity8
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Therapeutic Uses

Iodoform /was used/ as an antiseptic wound powder for a long time: today its use is limited.

Kirk-Othmer Encyclopedia of Chemical Technology. 3rd ed., Volumes 1-26. New York, NY: John Wiley and Sons, 1978-1984., p. 7(79) 803


FORMERLY WAS EMPLOYED AS A TOPICAL AND INTRAVITREAL ANTISEPTIC.

Grant, W.M. Toxicology of the Eye. 3rd ed. Springfield, IL: Charles C. Thomas Publisher, 1986., p. 524


ANTI-INFECTIVE (TOPICAL)

Budavari, S. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 1996., p. 863


MEDICATION (VET): ANTISEPTIC, DISINFECTANT FOR SUPERFICIAL LESIONS & IN THE FEMALE REPRODUCTIVE TRACT

Budavari, S. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 1996., p. 863


THERAP CAT: Anti-infective (topical)

Budavari, S. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 1996., p. 863


4.2 Drug Indication

No approved therapeutic indications.


5 Pharmacology and Biochemistry
5.1 Pharmacology

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. 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. 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.


5.2 ATC Code

D - Dermatologicals

D09 - Medicated dressings

D09A - Medicated dressings

D09AA - Medicated dressings with antiinfectives

D09AA13 - Iodoform


5.3 Absorption, Distribution and Excretion

Absorption

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


Route of Elimination

No pharmacokinetic data available.


Volume of Distribution

No pharmacokinetic data available.


Clearance

No pharmacokinetic data available.


5.4 Metabolism/Metabolites

It is expected to be oxidized to iodine.


HALOFORMS ARE METABOLIZED TO CARBON MONOXIDE BY HEPATIC MICROSOMAL MIXED FUNCTION OXIDASES & THIS REACTION IS MARKEDLY STIMULATED BY SULFHYDRYL COMPOUNDS. /HALOFORMS/

PMID:526325 STEVENS JL, ANDERS MW; BIOCHEM PHARM 28: 3189-94 (1979)


TRIHALOMETHANES (HALOFORMS) WERE METABOLIZED TO CARBON MONOXIDE BY A RAT LIVER MICROSOMAL FRACTION REQUIRING BOTH NADPH AND MOLECULAR OXYGEN FOR MAXIMAL ACTIVITY. THE METABOLISM OF HALOFORMS TO CARBON MONOXIDE FOLLOWED THE HALIDE ORDER; IODOFORM YIELDED THE GREATEST AMOUNT OF CARBON MONOXIDE, WHEREAS CHLOROFORM YIELDED THE SMALLEST AMOUNT.

PMID:15814 AHMED AE ET AL; DRUG METAB DISPOS 5 (2): 198-204 (1977)


ADMINISTRATION OF HALOFORMS (TRIHALOMETHANES) TO RATS LED TO SUBSTANTIAL ELEVATIONS IN BLOOD CARBON MONOXIDE LEVELS. /TRIHALOMETHANES/

PMID:30605 ANDERS MW ET AL; DRUG METAB DISPOS 6 (5): 556-60 (1978)


5.5 Biological Half-Life

No pharmacokinetic data available.


5.6 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. 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. 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 TNF. P. gingivalis is an anaerobic bacteria present in anaerobic oral niches including periapical sites and periodontal pockets.


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