Identification

Name
Captodiame
Accession Number
DB09014
Type
Small Molecule
Groups
Approved, Investigational
Description

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.

Structure
Thumb
Synonyms
  • 2-[(4-butylsulfanylphenyl)-phenyl-methyl]sulfanyl-N,N-dimethylethanamine
  • Captodiame
External IDs
AY 55074 / N 68
Product Ingredients
IngredientUNIICASInChI Key
Captodiamine hydrochloride9I7N9PR9J2904-04-1IQCZDPRPOLRNQX-UHFFFAOYSA-N
International/Other Brands
Covatine (Bailly-Creat) / Covatix (Lundbeck) / Suvren (Ayerst)
Categories
UNII
H93K9455DD
CAS number
486-17-9
Weight
Average: 359.592
Monoisotopic: 359.174141313
Chemical Formula
C21H29NS2
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

Pharmacology

Indication

Captodiame is indicated for the treatment of anxiety.

Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
A5-hydroxytryptamine receptor 2C
antagonist
Human
ASigma non-opioid intracellular receptor 1
agonist
Human
AD(3) dopamine receptor
agonist
Human
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
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.

Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
AlimemazineThe risk or severity of adverse effects can be increased when Captodiame is combined with Alimemazine.
AlprazolamThe risk or severity of adverse effects can be increased when Alprazolam is combined with Captodiame.
AmikacinThe risk or severity of adverse effects can be increased when Captodiame is combined with Amikacin.
AmitriptylineThe risk or severity of adverse effects can be increased when Amitriptyline is combined with Captodiame.
AmphetamineThe risk or severity of adverse effects can be increased when Amphetamine is combined with Captodiame.
AtomoxetineThe risk or severity of adverse effects can be increased when Atomoxetine is combined with Captodiame.
BaclofenThe risk or severity of adverse effects can be increased when Baclofen is combined with Captodiame.
BenzphetamineThe risk or severity of adverse effects can be increased when Benzphetamine is combined with Captodiame.
Benzyl alcoholThe risk or severity of adverse effects can be increased when Benzyl alcohol is combined with Captodiame.
Botulinum Toxin Type AThe risk or severity of adverse effects can be increased when Captodiame is combined with Botulinum Toxin Type A.
Food Interactions
Not Available

References

Synthesis Reference

Captodiamine synthesis: Hubner Oluf Herman, Petersen Povl Viggo. U.S. Patent 2,830,088 (1958).

General References
  1. 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. [PubMed:15383182]
  2. PENTNEY BH, BROTHERWOOD RW: Captodiame in anxiety states in general practice. Practitioner. 1960 Aug;185:218-21. [PubMed:14431646]
  3. Link [Link]
External Links
KEGG Drug
D07316
PubChem Compound
10240
PubChem Substance
310264972
ChemSpider
9823
ChEBI
135521
ChEMBL
CHEMBL2110809
Drugs.com
Drugs.com Drug Page
Wikipedia
Captodiame
ATC Codes
N05BB02 — Captodiame

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US2830088No1958-04-081978-04-08Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)124Hubner, O.F. and Petersen, P.V.; U.S. Patent 2,830,088; April 8,1958.
Predicted Properties
PropertyValueSource
Water Solubility5.96e-05 mg/mLALOGPS
logP5.66ALOGPS
logP6.13ChemAxon
logS-6.8ALOGPS
pKa (Strongest Basic)8.94ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area3.24 Å2ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity112.79 m3·mol-1ChemAxon
Polarizability44.41 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - EI-BGC-MSsplash10-0a4i-9110000000-8df1b919e0909028a2fc
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 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
Diphenylmethane / Aryl thioether / Thiophenol ether / Alkylarylthioether / Tertiary amine / Tertiary aliphatic amine / Thioether / Dialkylthioether / Sulfenyl compound / Amine
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Antagonist
General Function
Serotonin receptor activity
Specific 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-...
Gene Name
HTR2C
Uniprot ID
P28335
Uniprot Name
5-hydroxytryptamine receptor 2C
Molecular Weight
51820.705 Da
References
  1. 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. [PubMed:23863923]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Agonist
General Function
Opioid receptor activity
Specific 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 m...
Gene Name
SIGMAR1
Uniprot ID
Q99720
Uniprot Name
Sigma non-opioid intracellular receptor 1
Molecular Weight
25127.52 Da
References
  1. 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. [PubMed:23863923]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Agonist
General Function
G-protein coupled amine receptor activity
Specific Function
Dopamine receptor whose activity is mediated by G proteins which inhibit adenylyl cyclase. Promotes cell proliferation.
Gene Name
DRD3
Uniprot ID
P35462
Uniprot Name
D(3) dopamine receptor
Molecular Weight
44224.335 Da
References
  1. 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. [PubMed:23863923]

Drug created on June 23, 2014 11:17 / Updated on August 02, 2018 07:48