Explore a selection of our essential drug information below, or:
Identification
- Generic Name
- Captodiame
- DrugBank Accession Number
- DB09014
- Background
Captodiame, also known as captodiamine, is an antihistamine which is used as a sedative and anxiolytic. It is a derivative of diphenhydramine. Captodiame has been suggested for use in preventing benzodiazepine withdrawal syndrome.
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for Captodiame (DB09014)
- Weight
- Average: 359.592
Monoisotopic: 359.174141313 - Chemical Formula
- C21H29NS2
- Synonyms
- 2-[(4-butylsulfanylphenyl)-phenyl-methyl]sulfanyl-N,N-dimethylethanamine
- Captodiame
- External IDs
- AY 55074
- N 68
Pharmacology
- Indication
Captodiame is indicated for the treatment of anxiety.
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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 A5-hydroxytryptamine receptor 2C antagonistHumans ASigma non-opioid intracellular receptor 1 agonistHumans AD(3) dopamine receptor agonistHumans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Renal.
- 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
-TDLo oral 17mg/kg (human) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX). PMID: 13535337. -LD50 intraperitoneal 116mg/kg (mouse) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD. PMID: 13062090. -LD50 intravenous 72mg/kg (mouse) BEHAVIORAL: ATAXIA. PMID: 14109651.
- 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 software1,2-Benzodiazepine The risk or severity of CNS depression can be increased when Captodiame is combined with 1,2-Benzodiazepine. Acenocoumarol The risk or severity of adverse effects can be increased when Captodiame is combined with Acenocoumarol. Acetazolamide The risk or severity of CNS depression can be increased when Acetazolamide is combined with Captodiame. Acetophenazine The risk or severity of CNS depression can be increased when Acetophenazine is combined with Captodiame. Agomelatine The risk or severity of CNS depression can be increased when Agomelatine is combined with Captodiame. - Food Interactions
- Not Available
Products
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Ingredient UNII CAS InChI Key Captodiamine hydrochloride 9I7N9PR9J2 904-04-1 IQCZDPRPOLRNQX-UHFFFAOYSA-N - International/Other Brands
- Covatine (Bailly-Creat) / Covatix (Lundbeck) / Suvren (Ayerst)
Categories
- ATC Codes
- N05BB02 — Captodiame
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as diphenylmethanes. These are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Diphenylmethanes
- Direct Parent
- Diphenylmethanes
- Alternative Parents
- Thiophenol ethers / Alkylarylthioethers / Trialkylamines / Sulfenyl compounds / Dialkylthioethers / Organopnictogen compounds / Hydrocarbon derivatives
- Substituents
- Alkylarylthioether / Amine / Aromatic homomonocyclic compound / Aryl thioether / Dialkylthioether / Diphenylmethane / Hydrocarbon derivative / Organic nitrogen compound / Organonitrogen compound / Organopnictogen compound
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- H93K9455DD
- CAS number
- 486-17-9
- InChI Key
- IZLPZXSZLLELBJ-UHFFFAOYSA-N
- InChI
- InChI=1S/C21H29NS2/c1-4-5-16-23-20-13-11-19(12-14-20)21(24-17-15-22(2)3)18-9-7-6-8-10-18/h6-14,21H,4-5,15-17H2,1-3H3
- IUPAC Name
- [2-({[4-(butylsulfanyl)phenyl](phenyl)methyl}sulfanyl)ethyl]dimethylamine
- SMILES
- CCCCSC1=CC=C(C=C1)C(SCCN(C)C)C1=CC=CC=C1
References
- Synthesis Reference
Captodiamine synthesis: Hubner Oluf Herman, Petersen Povl Viggo. U.S. Patent 2,830,088 (1958).
- General References
- Mercier-Guyon C, Chabannes JP, Saviuc P: The role of captodiamine in the withdrawal from long-term benzodiazepine treatment. Curr Med Res Opin. 2004 Sep;20(9):1347-55. [Article]
- PENTNEY BH, BROTHERWOOD RW: Captodiame in anxiety states in general practice. Practitioner. 1960 Aug;185:218-21. [Article]
- Link [Link]
- External Links
- KEGG Drug
- D07316
- PubChem Compound
- 10240
- PubChem Substance
- 310264972
- ChemSpider
- 9823
- 89812
- ChEBI
- 135521
- ChEMBL
- CHEMBL2110809
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Captodiame
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
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Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US2830088 No 1958-04-08 1978-04-08 US 
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 124 Hubner, O.F. and Petersen, P.V.; U.S. Patent 2,830,088; April 8,1958. - Predicted Properties
Property Value Source Water Solubility 5.96e-05 mg/mL ALOGPS logP 5.66 ALOGPS logP 6.13 Chemaxon logS -6.8 ALOGPS pKa (Strongest Basic) 8.94 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 1 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 3.24 Å2 Chemaxon Rotatable Bond Count 10 Chemaxon Refractivity 112.79 m3·mol-1 Chemaxon Polarizability 44.41 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five No 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]- 188.58151 predictedDeepCCS 1.0 (2019) [M+H]+ 190.93951 predictedDeepCCS 1.0 (2019) [M+Na]+ 197.28206 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances, including ergot alkaloid derivatives, 1-2,5,-dimethoxy-4-iodophenyl-2-aminopropane (DOI) and lysergic acid diethylamide (LSD). Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors. Beta-arrestin family members inhibit signaling via G proteins and mediate activation of alternative signaling pathways. Signaling activates a phosphatidylinositol-calcium second messenger system that modulates the activity of phosphatidylinositol 3-kinase and down-stream signaling cascades and promotes the release of Ca(2+) ions from intracellular stores. Regulates neuronal activity via the activation of short transient receptor potential calcium channels in the brain, and thereby modulates the activation of pro-opiomelacortin neurons and the release of CRH that then regulates the release of corticosterone. Plays a role in the regulation of appetite and eating behavior, responses to anxiogenic stimuli and stress. Plays a role in insulin sensitivity and glucose homeostasis
- Specific Function
- 1-(4-iodo-2,5-dimethoxyphenyl)propan-2-amine binding
- Gene Name
- HTR2C
- Uniprot ID
- P28335
- Uniprot Name
- 5-hydroxytryptamine receptor 2C
- Molecular Weight
- 51804.645 Da
References
- Ring RM, Regan CM: Captodiamine, a putative antidepressant, enhances hypothalamic BDNF expression in vivo by synergistic 5-HT2c receptor antagonism and sigma-1 receptor agonism. J Psychopharmacol. 2013 Oct;27(10):930-9. doi: 10.1177/0269881113497614. Epub 2013 Jul 17. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- Functions in lipid transport from the endoplasmic reticulum and is involved in a wide array of cellular functions probably through regulation of the biogenesis of lipid microdomains at the plasma membrane. Involved in the regulation of different receptors it plays a role in BDNF signaling and EGF signaling. Also regulates ion channels like the potassium channel and could modulate neurotransmitter release. Plays a role in calcium signaling through modulation together with ANK2 of the ITP3R-dependent calcium efflux at the endoplasmic reticulum. Plays a role in several other cell functions including proliferation, survival and death. Originally identified for its ability to bind various psychoactive drugs it is involved in learning processes, memory and mood alteration (PubMed:16472803, PubMed:9341151). Necessary for proper mitochondrial axonal transport in motor neurons, in particular the retrograde movement of mitochondria. Plays a role in protecting cells against oxidative stress-induced cell death via its interaction with RNF112 (By similarity)
- Specific Function
- G protein-coupled opioid receptor activity
- Gene Name
- SIGMAR1
- Uniprot ID
- Q99720
- Uniprot Name
- Sigma non-opioid intracellular receptor 1
- Molecular Weight
- 25127.52 Da
References
- Ring RM, Regan CM: Captodiamine, a putative antidepressant, enhances hypothalamic BDNF expression in vivo by synergistic 5-HT2c receptor antagonism and sigma-1 receptor agonism. J Psychopharmacol. 2013 Oct;27(10):930-9. doi: 10.1177/0269881113497614. Epub 2013 Jul 17. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- Dopamine receptor whose activity is mediated by G proteins which inhibit adenylyl cyclase. Promotes cell proliferation
- Specific Function
- dopamine neurotransmitter receptor activity, coupled via Gi/Go
- Gene Name
- DRD3
- Uniprot ID
- P35462
- Uniprot Name
- D(3) dopamine receptor
- Molecular Weight
- 44194.315 Da
References
- Ring RM, Regan CM: Captodiamine, a putative antidepressant, enhances hypothalamic BDNF expression in vivo by synergistic 5-HT2c receptor antagonism and sigma-1 receptor agonism. J Psychopharmacol. 2013 Oct;27(10):930-9. doi: 10.1177/0269881113497614. Epub 2013 Jul 17. [Article]
Drug created at June 23, 2014 17:17 / Updated at October 07, 2024 17:57