NP-MRD: Showing NP-Card for bromhexine (NP0281619)

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Record Information

Version

2.0

Created at

2022-09-09 08:04:49 UTC

Updated at

2022-09-09 08:04:50 UTC

NP-MRD ID

NP0281619

Secondary Accession Numbers

None

Natural Product Identification

Common Name

bromhexine

Description

Bromhexine, also known as fluibron, belongs to the class of organic compounds known as phenylmethylamines. Phenylmethylamines are compounds containing a phenylmethtylamine moiety, which consists of a phenyl group substituted by an methanamine. Bromhexine is a very strong basic compound (based on its pKa). It is marketed under the trade name Bisolvon(R) in Germany, England, Belgium, France, Italy, Netherlands, Norway, Sweden, Australia, and South Africa. Bromhexine is not available in the United States. bromhexine is found in Justicia adhatoda. bromhexine was first documented in 1981 (PMID: 7027431). Bromhexine is an expectorant/mucolytic agent (PMID: 20031363) (PMID: 22027391) (PMID: 23781460) (PMID: 4065592).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 38 39  0  0  0  0  0  0  0  0999 V2000
    0.0581   -0.9752   -1.6177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0810   -0.4946   -0.2728 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8632    0.5019    0.0985 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2492    0.0770    0.1292 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7279   -1.1895   -0.1119 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0886   -1.5114   -0.0389 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6499   -3.3068   -0.3964 Br  0  0  0  0  0  0  0  0  0  0  0  0
    5.0048   -0.5434    0.2845 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5501    0.7333    0.5307 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8085    2.1233    0.9886 Br  0  0  0  0  0  0  0  0  0  0  0  0
    3.2181    1.0322    0.4556 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7853    2.3566    0.7162 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4130   -0.1869    0.1432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9544    0.9526   -0.6746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3257    1.3014   -0.0774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2250    0.1563   -0.5074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7656   -1.0830    0.1830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3191   -1.3971    0.0875 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0784   -2.0854   -1.5908 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0378   -0.6398   -2.0101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7363   -0.6243   -2.3156 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5833    0.8161    1.1540 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7078    1.3918   -0.5529 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0632   -1.9947   -0.3592 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0556   -0.7359    0.3539 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8228    2.8215    1.6411 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4039    2.8848   -0.0972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3732    0.1276    1.2058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3285    1.8369   -0.5539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1470    0.6461   -1.7046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3036    1.2892    1.0270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6606    2.2685   -0.4666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2313    0.0748   -1.6145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2489    0.3938   -0.1184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1152   -1.0221    1.2556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3472   -1.9420   -0.2495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0446   -2.0469    0.9481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1366   -2.0065   -0.8268 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
  2 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 11  4  1  0
 18 13  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  3 23  1  0
  5 24  1  0
  8 25  1  0
 12 26  1  0
 12 27  1  0
 13 28  1  0
 14 29  1  0
 14 30  1  0
 15 31  1  0
 15 32  1  0
 16 33  1  0
 16 34  1  0
 17 35  1  0
 17 36  1  0
 18 37  1  0
 18 38  1  0
M  END


  Mrv0541 06241409252D          

 18 19  0  0  0  0            999 V2000
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7144   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7144   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7144    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7144   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7144   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7144    1.2375    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
 10  7  2  0  0  0  0
 10  9  1  0  0  0  0
 11  7  1  0  0  0  0
 11  8  2  0  0  0  0
 12  5  1  0  0  0  0
 12  6  1  0  0  0  0
 13  8  1  0  0  0  0
 14 10  1  0  0  0  0
 14 13  2  0  0  0  0
 15 11  1  0  0  0  0
 16 13  1  0  0  0  0
 17 14  1  0  0  0  0
 18  1  1  0  0  0  0
 18  9  1  0  0  0  0
 18 12  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0281619

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN(CC1=CC(Br)=CC(Br)=C1N)C1CCCCC1

> <INCHI_IDENTIFIER>
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

> <FORMULA>
C14H20Br2N2

> <MOLECULAR_WEIGHT>
376.13

> <EXACT_MASS>
373.999323944

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
32.9797676588482

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,4-dibromo-6-{[cyclohexyl(methyl)amino]methyl}aniline

> <ALOGPS_LOGP>
4.08

> <JCHEM_LOGP>
4.422492411333334

> <ALOGPS_LOGS>
-5.02

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.88721557186338

> <JCHEM_PKA_STRONGEST_BASIC>
9.319157775443692

> <JCHEM_POLAR_SURFACE_AREA>
29.259999999999998

> <JCHEM_REFRACTIVITY>
85.56090000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.62e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
bromhexine

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 24-JUN-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-14         0                                  
HETATM    1  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   15 Br   UNK     0      -1.334   2.310   0.000  0.00  0.00          Br+0
HETATM   16 Br   UNK     0       4.001   2.310   0.000  0.00  0.00          Br+0
HETATM   17  N   UNK     0       4.001  -0.770   0.000  0.00  0.00           N+0
HETATM   18  N   UNK     0       2.667  -3.080   0.000  0.00  0.00           N+0
CONECT    1   18                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3   12                                                       
CONECT    6    4   12                                                       
CONECT    7   10   11                                                       
CONECT    8   11   13                                                       
CONECT    9   10   18                                                       
CONECT   10    7    9   14                                                  
CONECT   11    7    8   15                                                  
CONECT   12    5    6   18                                                  
CONECT   13    8   14   16                                                  
CONECT   14   10   13   17                                                  
CONECT   15   11                                                            
CONECT   16   13                                                            
CONECT   17   14                                                            
CONECT   18    1    9   12                                                  
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

View in JSmol

Synonyms

Value	Source
3,5-Dibromo-N(alpha)-cyclohexyl-N(alpha)-methyltoluene-alpha-2-diamine	ChEBI
Bromhexina	ChEBI
Bromhexinum	ChEBI
Fluibron	ChEBI
N-Cyclohexyl-N-methyl-(2-amino-3,5-dibrombenzyl)amine	ChEBI
3,5-Dibromo-N(a)-cyclohexyl-N(a)-methyltoluene-a-2-diamine	Generator
3,5-Dibromo-N(α)-cyclohexyl-N(α)-methyltoluene-α-2-diamine	Generator
Berlin-chemie brand OF bromhexine hydrochloride	MeSH
Boehrvet brand OF bromhexine hydrochloride	MeSH
Bromhexin berlin-chemie	MeSH
Bromhexin-ratiopharm	MeSH
Bromhexine, famel	MeSH
Flubron	MeSH
Hoechst brand OF bromhexine hydrochloride	MeSH
Krewel brand OF bromhexine hydrochloride	MeSH
Merckle brand OF bromhexine hydrochloride	MeSH
Monohydrochloride, bromhexine	MeSH
Mucohexine	MeSH
Novartis brand OF bromhexine hydrochloride	MeSH
SB CH Brand OF bromhexine hydrochloride	MeSH
SB-CH Brand OF bromhexine hydrochloride	MeSH
Bromhexin von CT	MeSH
CT Arzneimittel brand OF bromhexine hydrochloride	MeSH
Aparsonin	MeSH
BC, Bromhexin	MeSH
Bisolvon	MeSH
Bromhexin BC	MeSH
DurElix	MeSH
Hustentabs ratiopharm	MeSH
Hustentabs-ratiopharm	MeSH
Hustentabsratiopharm	MeSH
Quentan	MeSH
CT, Bromhexin von	MeSH
CT-Arzneimittel brand OF bromhexine hydrochloride	MeSH
Von CT, bromhexin	MeSH
Apex brand OF bromhexine hydrochloride	MeSH
Berlin chemie brand OF bromhexine hydrochloride	MeSH
Boots brand OF bromhexine hydrochloride	MeSH
Bromhexin berlin chemie	MeSH
Bromhexin ratiopharm	MeSH
Bromhexine monohydrochloride	MeSH
Dur-elix	MeSH
Fher brand OF bromhexine hydrochloride	MeSH
Hydrochloride, bromhexine	MeSH
Omniapharm brand OF bromhexine hydrochloride	MeSH
Tesacof	MeSH
3m Brand OF bromhexine hydrochloride	MeSH
Boehringer ingelheim brand OF bromhexine hydrochloride	MeSH
Bromhexin	MeSH
Bromhexin berlinchemie	MeSH
Bromhexine hydrochloride	MeSH
Bromhexinratiopharm	MeSH
Brotussol	MeSH
Darolan	MeSH
Dur elix	MeSH
Famel bromhexine	MeSH
Flegamin	MeSH
promeco Brand OF bromhexine hydrochloride	MeSH
Ratiopharm brand OF bromhexine hydrochloride	MeSH

Chemical Formula

C₁₄H₂₀Br₂N₂

Average Mass

376.1300 Da

Monoisotopic Mass

373.99932 Da

IUPAC Name

2,4-dibromo-6-{[cyclohexyl(methyl)amino]methyl}aniline

Traditional Name

bromhexine

CAS Registry Number

Not Available

SMILES

CN(CC1=CC(Br)=CC(Br)=C1N)C1CCCCC1

InChI Identifier

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

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Adhatoda vasica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylmethylamines. Phenylmethylamines are compounds containing a phenylmethtylamine moiety, which consists of a phenyl group substituted by an methanamine.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenylmethylamines

Direct Parent

Phenylmethylamines

Alternative Parents

Substituents

Benzylamine
Phenylmethylamine
2-bromoaniline
Aniline or substituted anilines
Bromobenzene
Cyclohexylamine
Halobenzene
Aralkylamine
Aryl bromide
Aryl halide
Tertiary amine
Tertiary aliphatic amine
Primary amine
Organopnictogen compound
Organonitrogen compound
Organobromide
Organohalogen compound
Amine
Organic nitrogen compound
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

organobromine compound (CHEBI:77032 )
tertiary amino compound (CHEBI:77032 )
substituted aniline (CHEBI:77032 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	4.08	ALOGPS
logP	4.42	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	19.89	ChemAxon
pKa (Strongest Basic)	9.32	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	29.26 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	85.56 m³·mol⁻¹	ChemAxon
Polarizability	32.98 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

DB09019

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Bromhexine

METLIN ID

Not Available

PubChem Compound

2442

PDB ID

Not Available

ChEBI ID

77032

Good Scents ID

Not Available

References

General References

Liu J, Chen X, Hu Y, Cheng G, Zhong D: Quantification of the major metabolites of bromhexine in human plasma using RRLC-MS/MS and its application to pharmacokinetics. J Pharm Biomed Anal. 2010 Apr 6;51(5):1134-41. doi: 10.1016/j.jpba.2009.11.024. Epub 2009 Dec 1. [PubMed:20031363 ]
Stojanov M, Nielsen HM, Larsen KL: Cyclodextrins: Efficient biocompatible solubilizing excipients for bromhexine liquid and semi-solid drug delivery systems. Int J Pharm. 2012 Jan 17;422(1-2):349-55. doi: 10.1016/j.ijpharm.2011.10.023. Epub 2011 Oct 17. [PubMed:22027391 ]
Kumar A, Nanda S: A validated high performance liquid chromatographic method for estimation of bromhexine and terbutaline in bulk and tablet dosage forms. Pharm Methods. 2011 Oct;2(4):218-22. doi: 10.4103/2229-4708.93389. [PubMed:23781460 ]
Prause JU, Jensen OA, Manthorpe R: Effect of bromhexine, ambroxol, and placebo on clinical and histopathological changes in "Sjogren" mice. Graefes Arch Clin Exp Ophthalmol. 1985;223(5):259-64. doi: 10.1007/BF02153656. [PubMed:4065592 ]
Manthorpe R, Frost-Larsen K, Hoj L, Isager H, Prause JU: Bromhexine treatment of Sjogren's syndrome: effect on lacrimal and salivary secretion, and on proteins in tear fluid and saliva. Scand J Rheumatol. 1981;10(3):177-80. doi: 10.3109/03009748109095294. [PubMed:7027431 ]
LOTUS database [Link]

Showing NP-Card for bromhexine (NP0281619)

MOL for NP0281619 (bromhexine)

3D MOL for NP0281619 (bromhexine)

3D SDF for NP0281619 (bromhexine)

3D-SDF for NP0281619 (bromhexine)

PDB for NP0281619 (bromhexine)

3D PDB for NP0281619 (bromhexine)

SMILES for NP0281619 (bromhexine)

INCHI for NP0281619 (bromhexine)

Structure for NP0281619 (bromhexine)

3D Structure for NP0281619 (bromhexine)