This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.
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Identification
- Generic Name
- Cinnamaldehyde
- DrugBank Accession Number
- DB14184
- Background
Cinnamaldehyde is a naturally occurring flavonoid that gives the spice cinnamon its flavour and odour. It occurs naturally in the bark of cinnamon trees and other species of the genus Cinnamomum such as camphor and cassia.
Sensitivity to cinnamaldehyde may be identified with a clinical patch test.
- Type
- Small Molecule
- Groups
- Approved, Experimental
- Structure
Structure for Cinnamaldehyde (DB14184)
- Weight
- Average: 132.1592
Monoisotopic: 132.057514878 - Chemical Formula
- C9H8O
- Synonyms
- (3E)-3-phenylprop-2-enal
- (E)-3-Phenyl-2-propenal
- (E)-3-Phenyl-propenal
- (E)-3-Phenylpropenal
- 3-phenylacrylaldehyde
- Cinnamal
- Cinnamaldehyde
- trans-Cinnamaldehyde
- trans-Cinnamic aldehyde
- Zimtaldehyde
Pharmacology
- Indication
Cinnamaldehyde is approved by the FDA for use within allergenic epicutaneous patch tests which are indicated for use as an aid in the diagnosis of allergic contact dermatitis (ACD) in persons 6 years of age and older.
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Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism ATransient receptor potential cation channel subfamily V member 3 activatorHumans ATransient receptor potential cation channel subfamily A member 1 activatorHumans - Absorption
Cinnamaldehyde is 52% absorbed through the skin and shown to be rapidly absorbed from the gut 1.
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Cinnamaldehyde is metabolized and excreted primarily in the urine and, to a minor extent, in the feces 1. After oral or intraperitoneal administration to rats and mice, 69–98% of the dose of cinnamaldehyde was recovered in the urine and feces within 24 h 1.
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
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.
Drug Interaction Integrate drug-drug
interactions in your softwareAmbroxol The risk or severity of methemoglobinemia can be increased when Cinnamaldehyde is combined with Ambroxol. Articaine The risk or severity of methemoglobinemia can be increased when Cinnamaldehyde is combined with Articaine. Benzocaine The risk or severity of methemoglobinemia can be increased when Cinnamaldehyde is combined with Benzocaine. Benzyl alcohol The risk or severity of methemoglobinemia can be increased when Cinnamaldehyde is combined with Benzyl alcohol. Bupivacaine The risk or severity of methemoglobinemia can be increased when Cinnamaldehyde is combined with Bupivacaine. - Food Interactions
- Not Available
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 Dso Dressing Cinnamaldehyde (5 mL / 100 mL) + Chlorobutanol (38.3 g / 100 mL) + Cinnamon oil (5 mL / 100 mL) + Clove oil (63.4 mL / 100 mL) + Methyl salicylate (2.5 mL / 100 mL) Liquid Dental Germiphene Corporation 1963-12-31 2014-07-24 Canada 
T.R.U.E. Test Thin-Layer Rapid Use Patch Test Cinnamaldehyde (41 ug/48h) + 2,2'-Dibenzothiazyl disulfide (20 ug/48h) + 2-mercaptobenzothiazole (61 ug/48h) + 4-(Isopropylamino)diphenylamine (10 ug/48h) + Bacitracin (486 ug/48h) + Balsam of Peru (648 ug/48h) + Benzocaine (378 ug/48h) + Benzylparaben (162 ug/48h) + Bisphenol A diglycidyl ether (32 ug/48h) + Bromothalonil (4 ug/48h) + Bronopol (203 ug/48h) + Budesonide (0.8 ug/48h) + Butylparaben (162 ug/48h) + Chlorquinaldol (77 ug/48h) + Cinchocaine hydrochloride (66 ug/48h) + Cinnamyl alcohol (63 ug/48h) + Clioquinol (77 ug/48h) + Cobalt chloride hexahydrate (4 ug/48h) + Diazolidinylurea (446 ug/48h) + Potassium dichromate (15.7 ug/48h) + Dipentamethylenethiuram disulfide (5.5 ug/48h) + Diphenylguanidine (68 ug/48h) + Disperse Blue 106 (41 ug/48h) + Disulfiram (5.5 ug/48h) + Ditiocarb zinc (68 ug/48h) + Ethyl hydroxybenzoate (162 ug/48h) + Ethylenediamine (18 ug/48h) + Eugenol (41 ug/48h) + Evernia prunastri (81 ug/48h) + Formaldehyde (146 ug/48h) + Geraniol (81 ug/48h) + Hydrocortisone butyrate (16 ug/48h) + Hydroxycitronellal (63 ug/48h) + Imidurea (486 ug/48h) + Isoeugenol (17 ug/48h) + Lanolin alcohols (810 ug/48h) + Methylchloroisothiazolinone (3 ug/48h) + Methylparaben (162 ug/48h) + Morpholinylmercaptobenzothiazole (20 ug/48h) + N,N'-diphenyl-1,4-phenylenediamine (25 ug/48h) + N-Cyclohexyl-N'-phenyl-1,4-phenylenediamine (25 ug/48h) + Neomycin sulfate (486 ug/48h) + Nickel sulfate hexahydrate (36 ug/48h) + Parthenolide (2 ug/48h) + Propylparaben (162 ug/48h) + Quaternium-15 (81 ug/48h) + Rosin (972 ug/48h) + Sodium aurotiosulfate (23 ug/48h) + Tetracaine hydrochloride (66 ug/48h) + Tetramethylthiuram monosulfide (5.5 ug/48h) + Thimerosal (6 ug/48h) + Thiohexam (20 ug/48h) + Thiram (5.5 ug/48h) + Tixocortol pivalate (2 ug/48h) + Zinc dibutyldithiocarbamate (68 ug/48h) + alpha-Amyl cinnamaldehyde (17 ug/48h) + p-Phenylenediamine (65 ug/48h) + p-tert-Butylphenol-formaldehyde resin (low molecular weight) (36 ug/48h) Kit Cutaneous SmartPractice Denmark ApS 2012-03-01 Not applicable US 
Categories
- Drug Categories
- Aldehydes
- Antimutagenic Agents
- Antineoplastic Agents
- Antineoplastic Agents, Phytogenic
- Cell-mediated Immunity
- Compounds used in a research, industrial, or household setting
- Diet, Food, and Nutrition
- Drugs that are Mainly Renally Excreted
- Flavoring Agents
- Food
- Food Additives
- Food Ingredients
- Increased Histamine Release
- Pharmaceutic Aids
- Pharmaceutical Preparations
- Physiological Phenomena
- Protective Agents
- Standardized Chemical Allergen
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as cinnamaldehydes. These are organic aromatic compounds containing a cinnamlaldehyde moiety, consisting of a benzene and an aldehyde group to form 3-phenylprop-2-enal.
- Kingdom
- Organic compounds
- Super Class
- Phenylpropanoids and polyketides
- Class
- Cinnamaldehydes
- Sub Class
- Not Available
- Direct Parent
- Cinnamaldehydes
- Alternative Parents
- Styrenes / Enals / Organic oxides / Hydrocarbon derivatives / Aldehydes
- Substituents
- Aldehyde / Alpha,beta-unsaturated aldehyde / Aromatic homomonocyclic compound / Benzenoid / Carbonyl group / Cinnamaldehyde / Enal / Hydrocarbon derivative / Monocyclic benzene moiety / Organic oxide
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- cinnamaldehydes (CHEBI:16731) / Monolignols (C00903)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- SR60A3XG0F
- CAS number
- 14371-10-9
- InChI Key
- KJPRLNWUNMBNBZ-QPJJXVBHSA-N
- InChI
- InChI=1S/C9H8O/c10-8-4-7-9-5-2-1-3-6-9/h1-8H/b7-4+
- IUPAC Name
- (2E)-3-phenylprop-2-enal
- SMILES
- O=C\C=C\C1=CC=CC=C1
References
- General References
- Belsito D, Bickers D, Bruze M, Calow P, Greim H, Hanifin JM, Rogers AE, Saurat JH, Sipes IG, Tagami H: A toxicologic and dermatologic assessment of related esters and alcohols of cinnamic acid and cinnamyl alcohol when used as fragrance ingredients. Food Chem Toxicol. 2007;45 Suppl 1:S1-23. doi: 10.1016/j.fct.2007.09.087. Epub 2007 Sep 18. [Article]
- External Links
- Human Metabolome Database
- HMDB0003441
- KEGG Compound
- C00903
- ChemSpider
- 553117
- BindingDB
- 50203065
- 1368153
- ChEBI
- 16731
- ChEMBL
- CHEMBL293492
- ZINC
- ZINC000001532777
- PDBe Ligand
- 9Y6
- Wikipedia
- Cinnamaldehyde
- PDB Entries
- 6agn / 7p76
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample dataNot Available Unknown Status Basic Science Dermatology/Skin - Other / Neuropathic Pain / Pain / Pruritus 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Liquid Dental Kit Cutaneous - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Not Available
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.409 mg/mL ALOGPS logP 2 ALOGPS logP 1.98 Chemaxon logS -2.5 ALOGPS pKa (Strongest Basic) -4.4 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 1 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 17.07 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 42.13 m3·mol-1 Chemaxon Polarizability 14.48 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 131.5251459 predictedDarkChem Lite v0.1.0 [M-H]- 131.8264459 predictedDarkChem Lite v0.1.0 [M-H]- 131.5650459 predictedDarkChem Lite v0.1.0 [M-H]- 131.4986459 predictedDarkChem Lite v0.1.0 [M-H]- 127.371864 predictedDeepCCS 1.0 (2019) [M-H]- 131.5251459 predictedDarkChem Lite v0.1.0 [M-H]- 131.8264459 predictedDarkChem Lite v0.1.0 [M-H]- 131.5650459 predictedDarkChem Lite v0.1.0 [M-H]- 131.4986459 predictedDarkChem Lite v0.1.0 [M-H]- 127.371864 predictedDeepCCS 1.0 (2019) [M+H]+ 132.5884459 predictedDarkChem Lite v0.1.0 [M+H]+ 131.9621776 predictedDarkChem Standard v0.1.0 [M+H]+ 132.5451459 predictedDarkChem Lite v0.1.0 [M+H]+ 132.7160459 predictedDarkChem Lite v0.1.0 [M+H]+ 130.63344 predictedDeepCCS 1.0 (2019) [M+H]+ 132.5884459 predictedDarkChem Lite v0.1.0 [M+H]+ 131.9621776 predictedDarkChem Standard v0.1.0 [M+H]+ 132.5451459 predictedDarkChem Lite v0.1.0 [M+H]+ 132.7160459 predictedDarkChem Lite v0.1.0 [M+H]+ 130.63344 predictedDeepCCS 1.0 (2019) [M+Na]+ 132.0049459 predictedDarkChem Lite v0.1.0 [M+Na]+ 131.9556459 predictedDarkChem Lite v0.1.0 [M+Na]+ 132.0995459 predictedDarkChem Lite v0.1.0 [M+Na]+ 132.0060459 predictedDarkChem Lite v0.1.0 [M+Na]+ 139.91643 predictedDeepCCS 1.0 (2019) [M+Na]+ 132.0049459 predictedDarkChem Lite v0.1.0 [M+Na]+ 131.9556459 predictedDarkChem Lite v0.1.0 [M+Na]+ 132.0995459 predictedDarkChem Lite v0.1.0 [M+Na]+ 132.0060459 predictedDarkChem Lite v0.1.0 [M+Na]+ 139.91643 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Activator
- General Function
- Receptor-activated non-selective calcium permeant cation channel. It is activated by innocuous (warm) temperatures and shows an increased response at noxious temperatures greater than 39 degrees Celsius. Activation exhibits an outward rectification. May associate with TRPV1 and may modulate its activity. Is a negative regulator of hair growth and cycling: TRPV3-coupled signaling suppresses keratinocyte proliferation in hair follicles and induces apoptosis and premature hair follicle regression (catagen)
- Specific Function
- calcium channel activity
- Gene Name
- TRPV3
- Uniprot ID
- Q8NET8
- Uniprot Name
- Transient receptor potential cation channel subfamily V member 3
- Molecular Weight
- 90635.115 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Activator
- General Function
- Ligand-activated Ca(2+)-permeable, nonselective cation channel involved in pain detection and possibly also in cold perception, oxygen concentration perception, cough, itch, and inner ear function (PubMed:17259981, PubMed:21195050, PubMed:21873995, PubMed:23199233, PubMed:25389312, PubMed:33152265). Has a relatively high Ca(2+) selectivity, with a preference for divalent over monovalent cations (Ca(2+) > Ba(2+) > Mg(2+) > NH4(+) > Li(+) > K(+)), the influx of cation into the cytoplasm leads to membrane depolarization (PubMed:19202543, PubMed:21195050). Has a central role in the pain response to endogenous inflammatory mediators, such as bradykinin and to a diverse array of irritants. Activated by a large variety of structurally unrelated electrophilic and non-electrophilic chemical compounds, such as allylthiocyanate (AITC) from mustard oil or wasabi, cinnamaldehyde, diallyl disulfide (DADS) from garlic, and acrolein, an environmental irritant (PubMed:20547126, PubMed:25389312, PubMed:27241698, PubMed:30878828). Electrophilic ligands activate TRPA1 by interacting with critical N-terminal Cys residues in a covalent manner (PubMed:17164327, PubMed:27241698, PubMed:31866091, PubMed:32641835). Non-electrophile agonists bind at distinct sites in the transmembrane domain to promote channel activation (PubMed:33152265). Acts also as an ionotropic cannabinoid receptor by being activated by delta(9)-tetrahydrocannabinol (THC), the psychoactive component of marijuana (PubMed:25389312). May be a component for the mechanosensitive transduction channel of hair cells in inner ear, thereby participating in the perception of sounds (By similarity)
- Specific Function
- calcium channel activity
- Gene Name
- TRPA1
- Uniprot ID
- O75762
- Uniprot Name
- Transient receptor potential cation channel subfamily A member 1
- Molecular Weight
- 127499.88 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
Drug created at July 03, 2018 17:24 / Updated at August 26, 2024 19:21