Bromhexine

Details

• Internal ID: a8418db9-c38c-43bb-938f-21da80a7b940
• Taxonomy: Benzenoids > Benzene and substituted derivatives > Phenylmethylamines
• IUPAC Name: 2,4-dibromo-6-[[cyclohexyl(methyl)amino]methyl]aniline
• SMILES (Canonical): CN(CC1=C(C(=CC(=C1)Br)Br)N)C2CCCCC2
• SMILES (Isomeric): CN(CC1=C(C(=CC(=C1)Br)Br)N)C2CCCCC2
• InChI: InChI=1S/C14H20Br2N2/c1-18(12-5-3-2-4-6-12)9-10-7-11(15)8-13(16)14(10)17/h7-8,12H,2-6,9,17H2,1H3
• InChI Key: OJGDCBLYJGHCIH-UHFFFAOYSA-N
• Popularity: 1,419 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₂₀Br₂N₂
• Molecular Weight: 376.13 g/mol
• Exact Mass: 375.99727 g/mol
• Topological Polar Surface Area (TPSA): 29.30 Ų
• XlogP: 4.30
• Atomic LogP (AlogP): 4.56
• H-Bond Acceptor: 2
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

• 3572-43-8
• Benzenemethanamine, 2-amino-3,5-dibromo-N-cyclohexyl-N-methyl-
• Bromhexina
• Bromhexinum
• Fluibron
• Bromhexine [INN:BAN]
• 2,4-Dibromo-6-((cyclohexyl(methyl)amino)methyl)aniline
• 2,4-dibromo-6-[[cyclohexyl(methyl)amino]methyl]aniline
• CHEBI:77032
• Bromhexinum [INN-Latin]
• Bromhexina [INN-Spanish]
• EINECS 222-684-1
• UNII-Q1J152VB1P
• Q1J152VB1P
• N-Cyclohexyl-N-methyl-(2-amino-3,5-dibrombenzyl)amin
• 2,4-dibromo-6-{[cyclohexyl(methyl)amino]methyl}aniline
• DTXSID6022686
• 3,5-Dibromo-Nalpha-cyclohexyl-Nalpha-methyltoluene-alpha-2-diamine
• Bromhexine (INN)
• N-cyclohexyl-N-methyl-(2-amino-3,5-dibrombenzyl)amine
• BROMHEXINE [INN]
• Bromhexinum (INN-Latin)
• 3,5-dibromo-N(alpha)-cyclohexyl-N(alpha)-methyltoluene-alpha-2-diamine
• Bromhexina (INN-Spanish)
• Toluene-.alpha.,2-diamine, 3,5-dibromo-N.alpha.-cyclohexyl-N.alpha.-methyl-
• BROMHEXINE (MART.)
• BROMHEXINE [MART.]
• N-2-AMINO-3,5-DIBROMOBENZYL-N-CYCLOHEXYLMETHYLAMINE
• Bromexine
• SMR001826324
• Bromexina
• Fluibron (TN)
• Spectrum_001392
• BROMHEXINE [MI]
• Spectrum2_001526
• Spectrum3_001152
• Spectrum4_000758
• Spectrum5_001054
• BROMHEXINE [WHO-DD]
• Oprea1_147116
• SCHEMBL19059
• BSPBio_002703
• KBioGR_001116
• KBioSS_001872
• MLS004774079
• MLS006011815
• DivK1c_000455
• SPBio_001312
• CHEMBL253376
• DTXCID202686
• [(2-amino-3,5-dibromophenyl)methyl]cyclohexylmethylamine
• GTPL11218
• KBio1_000455
• KBio2_001872
• KBio2_004440
• KBio2_007008
• KBio3_002203
• OJGDCBLYJGHCIH-UHFFFAOYSA-
• R05CB02
• NINDS_000455
• HMS2090K17
• NA274
• N-(2-AMINO-3,5-DIBROMOBENZYL)-N-CYCLOHEXYL-N-METHYLAMINE
• BDBM50239965
• s5943
• AKOS000305902
• DB09019
• IDI1_000455
• NCGC00178520-01
• NCGC00178520-02
• NCGC00178520-05
• SBI-0051773.P002
• D07542
• EN300-228940
• AB00053644-02
• AB00053644_03
• AB00053644_04
• A924042
• Q239778
• BRD-K47631482-003-02-1
• BRD-K47631482-003-03-9
• F2173-0412
• 2,4-Dibromo-6-([cyclohexyl(methyl)amino]methyl)aniline #
• 2-Amino-3,5-dibromo-N-cyclohexyl-N-methylbenzenemathanamine
• 2-Amino-3,5-dibromo-N-cyclohexyl-N-methyl benzenemethanamine
• InChI=1/C14H20Br2N2/c1-18(12-5-3-2-4-6-12)9-10-7-11(15)8-13(16)14(10)17/h7-8,12H,2-6,9,17H2,1H3

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9761	97.61%
Caco-2	+	0.9007	90.07%
Blood Brain Barrier	+	0.9500	95.00%
Human oral bioavailability	+	0.8714	87.14%
Subcellular localzation	Lysosomes	0.6554	65.54%
OATP2B1 inhibitior	-	0.8516	85.16%
OATP1B1 inhibitior	+	0.9390	93.90%
OATP1B3 inhibitior	+	0.9459	94.59%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	+	0.5250	52.50%
BSEP inhibitior	+	0.7153	71.53%
P-glycoprotein inhibitior	-	0.9538	95.38%
P-glycoprotein substrate	-	0.7520	75.20%
CYP3A4 substrate	-	0.5149	51.49%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.6486	64.86%
CYP3A4 inhibition	+	0.7991	79.91%
CYP2C9 inhibition	-	0.8088	80.88%
CYP2C19 inhibition	-	0.5759	57.59%
CYP2D6 inhibition	+	0.6923	69.23%
CYP1A2 inhibition	+	0.7963	79.63%
CYP2C8 inhibition	-	0.8413	84.13%
CYP inhibitory promiscuity	+	0.6468	64.68%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.7718	77.18%
Carcinogenicity (trinary)	Non-required	0.6167	61.67%
Eye corrosion	-	0.9886	98.86%
Eye irritation	-	0.9541	95.41%
Skin irritation	-	0.6854	68.54%
Skin corrosion	-	0.7939	79.39%
Ames mutagenesis	-	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8133	81.33%
Micronuclear	+	0.5700	57.00%
Hepatotoxicity	+	0.7500	75.00%
skin sensitisation	-	0.7379	73.79%
Respiratory toxicity	+	0.9444	94.44%
Reproductive toxicity	-	0.6026	60.26%
Mitochondrial toxicity	+	0.9875	98.75%
Nephrotoxicity	-	0.7485	74.85%
Acute Oral Toxicity (c)	III	0.5258	52.58%
Estrogen receptor binding	+	0.8906	89.06%
Androgen receptor binding	+	0.6045	60.45%
Thyroid receptor binding	-	0.5254	52.54%
Glucocorticoid receptor binding	+	0.6888	68.88%
Aromatase binding	-	0.5488	54.88%
PPAR gamma	+	0.7494	74.94%
Honey bee toxicity	-	0.9482	94.82%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.7100	71.00%
Fish aquatic toxicity	+	0.9968	99.68%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.10%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.04%	97.09%
CHEMBL2581	P07339	Cathepsin D	93.39%	98.95%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	93.00%	86.00%
CHEMBL1907594	P30926	Neuronal acetylcholine receptor; alpha3/beta4	89.96%	97.23%
CHEMBL3155	P34969	Serotonin 7 (5-HT7) receptor	87.79%	90.71%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.61%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.09%	95.56%
CHEMBL226	P30542	Adenosine A1 receptor	86.54%	95.93%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	86.16%	89.62%
CHEMBL241	Q14432	Phosphodiesterase 3A	85.21%	92.94%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	84.82%	91.11%
CHEMBL5203	P33316	dUTP pyrophosphatase	84.01%	99.18%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	83.85%	95.50%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.14%	92.62%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	82.53%	83.57%
CHEMBL249	P25103	Neurokinin 1 receptor	82.33%	99.17%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	80.90%	90.24%
CHEMBL1871	P10275	Androgen Receptor	80.79%	96.43%
CHEMBL228	P31645	Serotonin transporter	80.54%	95.51%
CHEMBL3012	Q13946	Phosphodiesterase 7A	80.18%	99.29%
CHEMBL253	P34972	Cannabinoid CB2 receptor	80.15%	97.25%

Plants that contains it

• Justicia adhatoda

Cross-Links

• PubChem: 2442
• LOTUS: LTS0204364
• wikiData: Q239778