1,3-dibromo-5,5-dimethylhydantoin

General Information

Mainterm	1,3-dibromo-5,5-dimethylhydantoin
CAS Reg.No.(or other ID)	77-48-5
Regnum

From www.fda.gov

Computed Descriptors

Download SDF

2D Structure
CID	6479
IUPAC Name	1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione
InChI	InChI=1S/C5H6Br2N2O2/c1-5(2)3(10)8(6)4(11)9(5)7/h1-2H3
InChI Key	VRLDVERQJMEPIF-UHFFFAOYSA-N
Canonical SMILES	CC1(C(=O)N(C(=O)N1Br)Br)C
Molecular Formula	C5H6Br2N2O2
Wikipedia	1,3-dibromo-5,5-dimethylhydantoin

From Pubchem

Computed Properties

Property Name	Property Value
Molecular Weight	285.923
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	0
Complexity	229.0
CACTVS Substructure Key Fingerprint	A A A D c Y B j M A A A G A A A A A A A A A A A A A A A A W A A A A A A A A A A A A A A A A A A A A A A H g A A E A A A D I i B g A A D A A I A A A A I A A E Q E A A A A A A A A A A A A A G A A A C A Q A A A A C A U A A A I B S I A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A = =
Topological Polar Surface Area	40.6
Monoisotopic Mass	283.88
Exact Mass	285.878
XLogP3	None
XLogP3-AA	1.5
Compound Is Canonicalized	True
Formal Charge	0
Heavy Atom Count	11
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Isotope Atom Count	0
Covalently-Bonded Unit Count	1

From Pubchem

ADMET Predicted Profile --- Classification

Model	Result	Probability
Absorption
Blood-Brain Barrier	BBB+	0.9815
Human Intestinal Absorption	HIA+	0.9931
Caco-2 Permeability	Caco2+	0.5000
P-glycoprotein Substrate	Non-substrate	0.7487
P-glycoprotein Inhibitor	Non-inhibitor	0.7145
P-glycoprotein Inhibitor	Non-inhibitor	0.9875
Renal Organic Cation Transporter	Non-inhibitor	0.9325
Distribution
Subcellular localization	Mitochondria	0.7877
Metabolism
CYP450 2C9 Substrate	Non-substrate	0.7661
CYP450 2D6 Substrate	Non-substrate	0.8314
CYP450 3A4 Substrate	Non-substrate	0.5744
CYP450 1A2 Inhibitor	Non-inhibitor	0.8111
CYP450 2C9 Inhibitor	Non-inhibitor	0.7615
CYP450 2D6 Inhibitor	Non-inhibitor	0.9153
CYP450 2C19 Inhibitor	Non-inhibitor	0.5807
CYP450 3A4 Inhibitor	Non-inhibitor	0.8576
CYP Inhibitory Promiscuity	Low CYP Inhibitory Promiscuity	0.9303
Excretion
Toxicity
Human Ether-a-go-go-Related Gene Inhibition	Weak inhibitor	0.9594
Human Ether-a-go-go-Related Gene Inhibition	Non-inhibitor	0.9215
AMES Toxicity	Non AMES toxic	0.8665
Carcinogens	Non-carcinogens	0.7860
Fish Toxicity	High FHMT	0.5927
Tetrahymena Pyriformis Toxicity	High TPT	0.9660
Honey Bee Toxicity	Low HBT	0.7733
Biodegradation	Not ready biodegradable	0.9489
Acute Oral Toxicity	II	0.7370
Carcinogenicity (Three-class)	Non-required	0.4904

From admetSAR

ADMET Predicted Profile --- Regression

Model	Value	Unit
Absorption
Aqueous solubility	-2.5962	LogS
Caco-2 Permeability	1.3715	LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity	3.0265	LD50, mol/kg
Fish Toxicity	2.2623	pLC50, mg/L
Tetrahymena Pyriformis Toxicity	0.6365	pIGC50, ug/L

From admetSAR

Toxicity Profile

Route of Exposure	Oral ; inhalation ; dermal
Mechanism of Toxicity	Bromine is a powerful oxidizing agent and is able to release oxygen free radicals from the water in mucous membranes. These free radicals are also potent oxidizers and produce tissue damage. In additon, the formation of hydrobromic and bromic acids will result in secondary irritation. The bromide ion is also known to affect the central nervous system, causing bromism. This is believed to be a result of bromide ions substituting for chloride ions in the in actions of neurotransmitters and transport systems, thus affecting numerous synaptic processes.
Metabolism	Bromine is mainly absorbed via inhalation, but may also enter the body through dermal contact. Bromine salts can be ingested. Due to its reactivity, bromine quickly forms bromide and may be deposited in the tissues, displacing other halogens.
Toxicity Values	None
Lethal Dose	None
Carcinogenicity (IARC Classification)	No indication of carcinogenicity to humans (not listed by IARC).
Minimum Risk Level	None
Health Effects	Bromine vapour causes irritation and direct damage to the mucous membranes. Elemental bromine also burns the skin. The bromide ion is a central nervous system depressant and chronic exposure produces neuronal effects. This is called bromism and can result in central reactions reaching from somnolence to coma, cachexia, exicosis, loss of reflexes or pathologic reflexes, clonic seizures, tremor, ataxia, loss of neural sensitivity, paresis, papillar edema of the eyes, abnormal speech, cerebral edema, delirium, aggressiveness, and psychoses. (L625, L626, L627)
Treatment	EYES: irrigate opened eyes for several minutes under running water. INGESTION: do not induce vomiting. Rinse mouth with water (never give anything by mouth to an unconscious person). Seek immediate medical advice. SKIN: should be treated immediately by rinsing the affected parts in cold running water for at least 15 minutes, followed by thorough washing with soap and water. If necessary, the person should shower and change contaminated clothing and shoes, and then must seek medical attention. INHALATION: supply fresh air. If required provide artificial respiration.
Reference	Ziouzenkova O, Orasanu G, Sharlach M, Akiyama TE, Berger JP, Viereck J, Hamilton JA, Tang G, Dolnikowski GG, Vogel S, Duester G, Plutzky J: Retinaldehyde represses adipogenesis and diet-induced obesity. Nat Med. 2007 Jun;13(6):695-702. Epub 2007 May 27.[17529981 ]

From T3DB

Taxonomic Classification

Kingdom	Organic compounds
Superclass	Organoheterocyclic compounds
Class	Azolidines
Subclass	Imidazolidines
Intermediate Tree Nodes	Imidazolidinones - Imidazolidinediones
Direct Parent	Hydantoins
Alternative Parents	Organopnictogen compounds Alpha amino acids and derivatives Organic oxides Dicarboximides Hydrocarbon derivatives Organic carbonic acids and derivatives Organonitrogen compounds Carbonyl compounds Azacyclic compounds
Molecular Framework	Aliphatic heteromonocyclic compounds
Substituents	Hydantoin - Alpha-amino acid or derivatives - Dicarboximide - Carbonic acid derivative - Azacycle - Carboxylic acid derivative - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Organonitrogen compound - Carbonyl group - Aliphatic heteromonocyclic compound
Description	This compound belongs to the class of organic compounds known as hydantoins. These are heterocyclic compounds containing an imidazolidine substituted by ketone group at positions 2 and 4.

From ClassyFire

Targets

Target Details

Cytochrome P450 4F12

General Function:: Leukotriene-b4 20-monooxygenase activity
Specific Function:: Catalyzes leukotriene B4 omega-hydroxylation and arachidonic acid omega-hydroxylation but with an activity much lower than that of CYP4F2. Catalyzes the hydroxylation of the antihistamine ebastine.
Gene Name:: CYP4F12
Uniprot ID:: Q9HCS2
Molecular Weight:: 60269.165 Da

References

Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]

From T3DB