Identification
- Summary
Terpin hydrate is an expectorant used to treat bronchitis, pneumonia, bronchiectasis, COPD, and infectious or inflammatory diseases of the upper respiratory tract.
- Generic Name
- Terpin hydrate
- DrugBank Accession Number
- DB13163
- Background
Terpin hydrate is an expectorant, commonly used to loosen mucus and ease congestion in patients presenting with acute or chronic bronchitis, and related pulmonary conditions. It is derived from sources such as turpentine, oregano, thyme and eucalyptus. It was popular in the United States since the late nineteenth century, but was removed from marketed medications in the 1990s after FDA stated that "based on evidence currently available, there are inadequate data to establish general recognition of the safety and effectiveness of these ingredients". Elixirs of terpin hydrate are still available to patients as prescription medications to be prepared by specialty compounding pharmacies.
- Type
- Small Molecule
- Groups
- Approved, Experimental
- Structure
Structure for Terpin hydrate (DB13163)
- Weight
- Average: 190.283
Monoisotopic: 190.156894568 - Chemical Formula
- C10H22O3
- Synonyms
- cis-p-methane-1,8-diol monohydrate
- cis-terpin hydrate
- Terpin cis-form hydrate
- Terpin hydrate
- Terpin monohydrate
- Terpinene hydrate
- Terpinol hydrate
- External IDs
- AI3-01762
Pharmacology
- Indication
Terpin hydrate is used in the treatment of acute and chronic bronchitis, pneumonia, bronchiectasis, chronic obstructive pulmonary disease, infectious and inflammatory diseases of the upper respiratory tract.
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Used in combination to treat Cough caused by common cold Combination Product in combination with: Chlorpheniramine (DB01114) •••••••••••• •••••• Used in combination to treat Cough caused by common cold Combination Product in combination with: Dextromethorphan (DB00514), Guaifenesin (DB00874), Brompheniramine (DB00835) •••••••••••• •••••• Used in combination to treat Coughing caused by bronchitis Combination Product in combination with: Dextromethorphan (DB00514), Brompheniramine (DB00835), Guaifenesin (DB00874) •••••••••••• •••••• Used in combination to treat Rhinorrhoea Combination Product in combination with: Chlorpheniramine (DB01114) •••••••••••• •••••• - Associated Therapies
- Contraindications & Blackbox Warnings
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It acts to facilitate the removal of mucus from the respiratory tract. It prevents the exacerbation of excessive mucus production and secretion due to airway bacterial or viral infections, asthma or chronic bronchitis. Expectorants like terpin hydrate change mucus consistency and make coughing more productive.
- Mechanism of action
Terpin hydrate improves mucociliary function by working directly on the bronchial secretory cells in the lower respiratory tract to liquify and facilitate the elimination of bronchial secretionsas well as exerting a weak antiseptic effect on the pulmonary parenchyma. It is thought to increase the amount of fluid in the respiratory tract, which increases the flow and clearance of local irritants and as well as reducing the viscosity of mucus 2.
- 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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Overdose can cause nausea, vomiting and abdominal pain.
- 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
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Pastilles Valda Terpin hydrate (.016 mg) + Eucalyptol (.451 mg) + Guaiacol (.016 mg) + Levomenthol (3.28 mg) + Thymol (.016 mg) Lozenge Oral Labs Valda 1981-12-31 1997-08-01 Canada 
Terpin Hydrate Codeine Elx CF Terpin hydrate (1.83 %) + Codeine (.23 %) Elixir Oral Stanley Pharmaceuticals, A Division Of Vita Health Products Inc. 1965-12-31 1997-08-08 Canada UDECOF TABLET Terpin hydrate (85 mg) + Dextromethorphan hydrobromide (20 mg) + Guaifenesin (50 mg) Tablet, coated Oral บริษัท สหการโอสถ (1996) จำกัด จำกัด 2009-04-09 Not applicable Thailand 
Valda Pastilles Terpin hydrate (.016 mg / loz) + Eucalyptol (.451 mg / loz) + Guaiacol (.016 mg / loz) + Levomenthol (3.28 mg / loz) + Thymol (.016 mg / loz) Lozenge Oral Bayer Inc Consumer Care 1995-12-31 2007-08-02 Canada Valda Pastilles Lemon Flavoured Terpin hydrate (.016 mg / loz) + Eucalyptol (.451 mg / loz) + Guaiacol (.016 mg / loz) + Levomenthol (3.28 mg / loz) + Thymol (.016 mg / loz) Lozenge Oral Labs Valda 1992-12-31 1996-09-10 Canada
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes.
- Kingdom
- Organic compounds
- Super Class
- Lipids and lipid-like molecules
- Class
- Prenol lipids
- Sub Class
- Monoterpenoids
- Direct Parent
- Menthane monoterpenoids
- Alternative Parents
- Monocyclic monoterpenoids / Cyclohexanols / Tertiary alcohols / Cyclic alcohols and derivatives / Organic oxides / Hydrocarbon derivatives
- Substituents
- Alcohol / Aliphatic homomonocyclic compound / Cyclic alcohol / Cyclohexanol / Hydrocarbon derivative / Monocyclic monoterpenoid / Organic oxide / Organic oxygen compound / Organooxygen compound / P-menthane monoterpenoid
- Molecular Framework
- Aliphatic homomonocyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- S3V868548T
- CAS number
- 2451-01-6
- InChI Key
- JGKJMBOJWVAMIJ-OFAZAQPOSA-N
- InChI
- InChI=1S/C10H20O2.H2O/c1-9(2,11)8-4-6-10(3,12)7-5-8;/h8,11-12H,4-7H2,1-3H3;1H2/t8-,10+;
- IUPAC Name
- (1s,4s)-4-(2-hydroxypropan-2-yl)-1-methylcyclohexan-1-ol hydrate
- SMILES
- O.CC(C)(O)[C@H]1CC[C@@](C)(O)CC1
References
- General References
- Seagrave J, Albrecht HH, Hill DB, Rogers DF, Solomon G: Effects of guaifenesin, N-acetylcysteine, and ambroxol on MUC5AC and mucociliary transport in primary differentiated human tracheal-bronchial cells. Respir Res. 2012 Oct 31;13:98. doi: 10.1186/1465-9921-13-98. [Article]
- 12. (2011). In Applied Pharmacology (pp. 129). Elsevier Health Sciences. [ISBN:978-1-4377-0310-8]
- External Links
- MSDS
- Download (79.1 KB)
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Tablet Oral Lozenge Oral Elixir Oral Tablet, coated Oral Tablet Tablet, sugar coated Oral Capsule - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 116 MSDS water solubility Partially soluble in cold water MSDS logP 2.320 ChemIDplus - Predicted Properties
Property Value Source Water Solubility 8.31 mg/mL ALOGPS logP 1.85 ALOGPS logP 1.19 Chemaxon logS -1.3 ALOGPS pKa (Strongest Acidic) 18.93 Chemaxon pKa (Strongest Basic) -0.69 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 40.46 Å2 Chemaxon Rotatable Bond Count 1 Chemaxon Refractivity 49.37 m3·mol-1 Chemaxon Polarizability 20.11 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 144.99861 predictedDeepCCS 1.0 (2019) [M+H]+ 147.39418 predictedDeepCCS 1.0 (2019) [M+Na]+ 153.3067 predictedDeepCCS 1.0 (2019)
Drug created at January 07, 2017 03:12 / Updated at May 27, 2021 02:58