Bromhexine

Identification

Name

Bromhexine

Accession Number

DB09019

Description

Bromhexine is an expectorant/mucolytic agent. Bromhexine is not available in the United States. It is marketed under the trade name Bisolvon(R) in Germany, England, Belgium, France, Italy, Netherlands, Norway, Sweden, Australia, and South Africa.

Type

Small Molecule

Groups

Approved

Structure

3D

Download

MOLSDF3D-SDFPDBSMILESInChI

Similar Structures

Structure for Bromhexine (DB09019)

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Weight

Average: 376.13
Monoisotopic: 373.999323944

Chemical Formula

C₁₄H₂₀Br₂N₂

Synonyms

• 3,5-dibromo-N(alpha)-cyclohexyl-N(alpha)-methyltoluene-alpha-2-diamine
• Bromexina
• Bromhexina
• Bromhexine
• Bromhexinum
• N-cyclohexyl-N-methyl-(2-amino-3,5-dibrombenzyl)amine

External IDs

• NA 274

Pharmacology

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Indication

Not Available

Associated Conditions

• Bronchiectasis
• Common Cold
• Cough caused by Common Cold
• Coughing
• Nasal Congestion
• Whooping Cough

Associated Therapies

• Airway secretion clearance therapy

Contraindications & Blackbox Warnings

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Pharmacodynamics

Not Available

Mechanism of action

Not Available

Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Not Available

Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects

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Toxicity

Not Available

Affected organisms

Not Available

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

No interactions found.

Products

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Product Ingredients

Ingredient	UNII	CAS	InChI Key
Bromhexine hydrochloride	YC2ZOM3Z8V	611-75-6	UCDKONUHZNTQPY-UHFFFAOYSA-N

International/Other Brands

Amiorel (Boehringer Ingelheim) / Bisolmed (Boehringer Ingelheim) / Bisolvon (Boehringer Ingelheim) / Bisolvon Chesty (Boehringer Ingelheim) / Fluibron

Over the Counter Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
BROMHEXINE ELIXIR	Elixir	4 mg/5ml	Oral	บริษัท พาตาร์แลบ (2517) จำกัด จำกัด	2013-05-08	Not applicable
BROMXINE	Tablet	8 mg	Oral	บริษัท โรงงานเภสัชกรรมแอตแลนติค จำกัด	1987-06-15	Not applicable
คอนเฮกซิน	Syrup	4 mg/5ml	Oral	บริษัท คอนติเนนเติล-ฟาร์ม จำกัด จำกัด	1998-03-18	Not applicable
ดูทรอส	Tablet	8 mg	Oral	บริษัท ไทยนครพัฒนา จำกัด	1996-03-26	Not applicable
ดูทรอส	Syrup	4 mg/5ml	Oral	บริษัท ไทยนครพัฒนา จำกัด	1997-12-10	Not applicable
บรอนมูคอน	Tablet	8 mg	Oral	ห้างหุ้นส่วนจำกัด สุพงษ์เภสัช	1983-06-28	Not applicable
บรอนเคลีย ชนิดเม็ด	Tablet	8 mg	Oral	บริษัท โปลิฟาร์ม จำกัด จำกัด	1985-08-20	Not applicable
บรอนเคส ชนิดน้ำเชื่อม	Syrup	4 mg/5ml	Oral	บริษัท โรงงานผลิตเวชภัณฑ์ชินต้าเทรดดิ้ง (1971) จำกัด จำกัด	2000-06-06	Not applicable
บรอมซิดอน อิลิกซ์เซอร์	Solution		Oral	บริษัท โรงงานเภสัชอุตสาหกรรม เจเอสพี (ประเทศไทย) จำกัด (มหาชน)	2020-03-17	Not applicable
บรอมซิน ไซรัป	Syrup	4 mg/5ml	Oral	บริษัท ยูเมด้า จำกัด	2000-12-18	Not applicable

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End	Region	Image
ROBITUSSIN ME	Bromhexine (4 MG/5ML) + Guaifenesin (100 MG/5ML)	Syrup	Oral	บริษัท แกล็กโซสมิทไคล์น คอนซูมเมอร์ เฮลธ์แคร์ (ประเทศไทย) จำกัด	2020-06-10	Not applicable
คูป้า	Bromhexine hydrochloride (4 mg) + Guaifenesin (100 mg)	Tablet		บริษัท เอ็ม แอนด์ เอ็ช แมนูแฟคเจอริ่ง จำกัด	1988-03-22	Not applicable
ดูทรอส เอ็กซ์	Bromhexine hydrochloride (4 mg/5mL) + Potassium guaiacolsulfonate (200 mg/5mL)	Syrup		บริษัท ไทยนครพัฒนา จำกัด	2013-02-06	Not applicable
ทอไกลโคโล่	Bromhexine hydrochloride (2 mg/5mL) + Potassium guaiacolsulfonate (200 mg/5mL)	Syrup		บริษัท สยามเภสัช จำกัด	1985-09-17	Not applicable
ทอไกลโคโล่ ชนิดเม็ด	Bromhexine hydrochloride (4 mg) + Guaifenesin (100 mg)	Tablet		บริษัท สยามเภสัช จำกัด	1987-04-21	Not applicable
เอ็กซ์โทแรนท์	Bromhexine hydrochloride (4 mg) + Guaifenesin (100 mg)	Tablet		บริษัท เคนยากุ (ประเทศไทย) จำกัด	1985-06-15	Not applicable
ไบโซลวอน เอ็กซ์	Bromhexine (4 MG/5ML) + Guaifenesin (100 MG/5ML)	Syrup	Oral	บริษัท ซาโนฟี่-อเวนตีส (ประเทศไทย) จำกัด	2017-03-18	Not applicable

Categories

ATC Codes

R05CB02 — Bromhexine

• R05CB — Mucolytics
• R05C — EXPECTORANTS, EXCL. COMBINATIONS WITH COUGH SUPPRESSANTS
• R05 — COUGH AND COLD PREPARATIONS
• R — RESPIRATORY SYSTEM

Drug Categories

• Amines
• Aniline Compounds
• Cough and Cold Preparations
• Cyclohexanes
• Cyclohexylamines
• Cycloparaffins
• Expectorants
• Respiratory System Agents

Chemical TaxonomyProvided by Classyfire

Description

This compound belongs to the class of organic compounds known as phenylmethylamines. These 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

Benzylamines / 2-bromoanilines / Cyclohexylamines / Bromobenzenes / Aralkylamines / Aryl bromides / Trialkylamines / Primary amines / Organopnictogen compounds / Organobromides / Hydrocarbon derivatives

show 1 more

Substituents

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

show 11 more

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

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

Chemical Identifiers

UNII

Q1J152VB1P

CAS number

3572-43-8

InChI Key

OJGDCBLYJGHCIH-UHFFFAOYSA-N

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

IUPAC Name

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

SMILES

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

References

Synthesis Reference

U.S. Patent 3,336,308.

General References

1. NPRA Product Information: Salmodil (salbutamol sulfate/bromhexine hydrochloride) oral syrup [Link]
2. NPRA Product Information: Rexom Unizet (diphenhydramine hydrochloride/bromhexine hydrochloride/ammonium chloride) oral syrup [Link]

External Links

KEGG Drug

D07542

PubChem Compound

2442

PubChem Substance

310264976

ChemSpider

2348

BindingDB

50239965

RxNav

1753

ChEBI

77032

ChEMBL

CHEMBL253376

ZINC

ZINC000000608220

Drugs.com

Drugs.com Drug Page

Wikipedia

Bromhexine

Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count
4	Completed	Prevention	Coronavirus Disease 2019 (COVID‑19) / Increased Risk of SARS-CoV-2 Infection	1
4	Recruiting	Treatment	Coronavirus Disease 2019 (COVID‑19)	1
3	Recruiting	Treatment	Abnormal Mucus Secretions / Respiratory Tract Diseases	1
3	Recruiting	Treatment	Coronavirus Disease 2019 (COVID‑19) / COVID 19	1
1	Not Yet Recruiting	Treatment	Pharmacokinetics	1
0	Enrolling by Invitation	Prevention	Antimalarials / Antirheumatic Agents / Coronavirus Disease 2019 (COVID‑19) / Enzyme Inhibitors / Hydroxychloroquine	1
Not Available	Active Not Recruiting	Treatment	Coronavirus Disease 2019 (COVID‑19) / Novel Coronavirus Pneumonia	1

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage Forms

Form	Route	Strength
Granule		8 MG
Injection	Intramuscular; Intravenous	2 MG/ML
Injection, solution		4 MG/2ML
Suppository	Rectal	16 MG
Suppository	Rectal	8 MG
Solution	Oral	2 mg/ml
Solution	Oral	4 mg/5ml
Solution	Oral	8 MG/5ML
Tablet	Oral	8 mg/1
Solution	Respiratory (inhalation)	0.2 g
Tablet, soluble	Oral	8 mg
Syrup	Oral	150 mg/5mL
Tablet		150 mg
Syrup	Oral	7.5 mg
Solution	Oral	80 mg
Syrup	Oral	4 mg/5ml
Tablet	Oral	8 mg
Syrup	Oral	200 ml
Tablet, sugar coated	Oral	8 mg/1
Solution	Oral
Tablet	Oral	12 MG
Solution	Oral	12 MG/ML
Solution	Oral	8 MG/ML
Syrup	Oral	0.16 g
Syrup	Oral	0.08 g
Powder	Not applicable	1000 g/1000g
Syrup	Oral	0.04 g
Tablet	Oral	4 MG
Cream	Oral; Vaginal	80 mg
Syrup	Oral	100 ml
Syrup	Oral	8 MG/5ML
Syrup	Oral	50 mg
Elixir	Oral	8 MG/5ML
Solution	Oral	0.8 mg/ml
Tablet		8 mg
Elixir	Oral	4 mg/5ml
Capsule, liquid filled	Oral	8 mg
Solution	Oral	160 mg
Syrup	Oral
Injection	Intramuscular; Intravenous	4 mg/2ml
Syrup	Oral	80 mg
Syrup	Oral	40 mg
Solution	Oral	0.16 g
Syrup	Oral	160 mg
Solution	Oral	0.08 g
Syrup	Oral	150 mg
Syrup	Oral	2 mg/5ml
Tablet, film coated	Oral	8 MG
Solution	Oral	0.04 g
Tablet, sugar coated	Oral
Capsule
Capsule
Solution
Syrup
Tablet
Tablet, film coated
Syrup	Oral

Prices

Not Available

Patents

Not Available

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	232-235	U.S. Patent 3,336,308.

Predicted Properties

Property	Value	Source
Water Solubility	0.00362 mg/mL	ALOGPS
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	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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	Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
LC-MS/MS Spectrum - LC-ESI-QTOF , positive	LC-MS/MS	splash10-03di-0095000000-2c4f15e31beb22fd1178
LC-MS/MS Spectrum - LC-ESI-QTOF , positive	LC-MS/MS	splash10-03di-0090000000-4d3be1605bfa79609959
LC-MS/MS Spectrum - LC-ESI-QTOF , positive	LC-MS/MS	splash10-03di-0090000000-428c05c13a2a9e326945
LC-MS/MS Spectrum - LC-ESI-QTOF , positive	LC-MS/MS	splash10-03di-0390000000-b0ece5d5d6f8b78af198

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Drug created on June 24, 2014 16:22 / Updated on February 21, 2021 18:52