Terpin hydrate

Identification

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Name
Terpin hydrate
Accession Number
DB13163
Type
Small Molecule
Groups
Approved, Experimental
Description

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.

Structure
Thumb
Synonyms
  • cis-p-methane-1,8-diol monohydrate
  • cis-terpin hydrate
  • Terpin cis-form hydrate
  • Terpin monohydrate
  • Terpinene hydrate
  • Terpinol hydrate
External IDs
AI3-01762
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Pastilles ValdaTerpin hydrate (.016 mg) + Eucalyptol (.451 mg) + Guaiacol (.016 mg) + Levomenthol (3.28 mg) + Thymol (.016 mg)LozengeOralLabs Valda1981-12-311997-08-01Canada
Terpin Hydrate Codeine Elx CFTerpin hydrate (1.83 %) + Codeine (.23 %)ElixirOralStanley Pharmaceuticals, A Division Of Vita Health Products Inc.1965-12-311997-08-08Canada
Valda PastillesTerpin hydrate (.016 mg) + Eucalyptol (.451 mg) + Guaiacol (.016 mg) + Levomenthol (3.28 mg) + Thymol (.016 mg)LozengeOralBayer Inc Consumer Care1995-12-312007-08-02Canada
Valda Pastilles Lemon FlavouredTerpin hydrate (.016 mg) + Eucalyptol (.451 mg) + Guaiacol (.016 mg) + Levomenthol (3.28 mg) + Thymol (.016 mg)LozengeOralLabs Valda1992-12-311996-09-10Canada
Categories
UNII
S3V868548T
CAS number
2451-01-6
Weight
Average: 190.283
Monoisotopic: 190.156894568
Chemical Formula
C10H22O3
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

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.

Pharmacodynamics

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
Toxicity

Overdose can cause nausea, vomiting and abdominal pain.

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
Not Available

References

General References
  1. 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. [PubMed:23113953]
  2. 12. (2011). In Applied Pharmacology (pp. 129). Elsevier Health Sciences. [ISBN:978-1-4377-0310-8]
External Links
PubChem Compound
17141
PubChem Substance
347829270
ChemSpider
16736914
Wikipedia
Terpin_hydrate
MSDS
Download (79.1 KB)

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
LozengeOral
ElixirOral
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)116MSDS
water solubilityPartially soluble in cold waterMSDS
logP2.320ChemIDplus
Predicted Properties
PropertyValueSource
Water Solubility8.31 mg/mLALOGPS
logP1.85ALOGPS
logP1.19ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)18.93ChemAxon
pKa (Strongest Basic)-0.69ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity49.37 m3·mol-1ChemAxon
Polarizability20.11 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

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
P-menthane monoterpenoid / Monocyclic monoterpenoid / Cyclohexanol / Tertiary alcohol / Cyclic alcohol / Organic oxygen compound / Organic oxide / Hydrocarbon derivative / Organooxygen compound / Alcohol
Molecular Framework
Aliphatic homomonocyclic compounds
External Descriptors
Not Available

Drug created on January 06, 2017 20:12 / Updated on September 02, 2019 19:53