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Identification
NameCaptodiame
Accession NumberDB09014
TypeSmall Molecule
GroupsApproved, Investigational
DescriptionCaptodiame, 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 Identifiers
  • AY 55074
  • N 68
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
CovatineBailly-Creat
CovatixLundbeck
SuvrenAyerst
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Captodiamine hydrochloride
ThumbNot applicableDBSALT001090
Categories
UNIIH93K9455DD
CAS number486-17-9
WeightAverage: 359.592
Monoisotopic: 359.174141313
Chemical FormulaC21H29NS2
InChI KeyInChIKey=IZLPZXSZLLELBJ-UHFFFAOYNA-N
InChI
InChI=1/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
Taxonomy
ClassificationNot classified
Pharmacology
IndicationCaptodiame is indicated for the treatment of anxiety.
PharmacodynamicsNot Available
Mechanism of actionNot Available
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationRenal.
Half lifeNot Available
ClearanceNot 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 organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal AbsorptionNot AvailableNot Available
Blood Brain BarrierNot AvailableNot Available
Caco-2 permeableNot AvailableNot Available
P-glycoprotein substrateNot AvailableNot Available
P-glycoprotein inhibitor INot AvailableNot Available
P-glycoprotein inhibitor IINot AvailableNot Available
Renal organic cation transporterNot AvailableNot Available
CYP450 2C9 substrateNot AvailableNot Available
CYP450 2D6 substrateNot AvailableNot Available
CYP450 3A4 substrateNot AvailableNot Available
CYP450 1A2 substrateNot AvailableNot Available
CYP450 2C9 inhibitorNot AvailableNot Available
CYP450 2D6 inhibitorNot AvailableNot Available
CYP450 2C19 inhibitorNot AvailableNot Available
CYP450 3A4 inhibitorNot AvailableNot Available
CYP450 inhibitory promiscuityNot AvailableNot Available
Ames testNot AvailableNot Available
CarcinogenicityNot AvailableNot Available
BiodegradationNot AvailableNot Available
Rat acute toxicityNot AvailableNot applicable
hERG inhibition (predictor I)Not AvailableNot Available
hERG inhibition (predictor II)Not AvailableNot Available
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US2830088 No1958-04-081978-04-08Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point124Hubner, 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 FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot 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
ATC CodesN05BB02
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
YohimbineThe therapeutic efficacy of Captodiame can be decreased when used in combination with Yohimbine.
Food InteractionsNot 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-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 modul...
Gene Name:
HTR2C
Uniprot ID:
P28335
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 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 neurotransmitt...
Gene Name:
SIGMAR1
Uniprot ID:
Q99720
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
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 ]
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Drug created on June 23, 2014 11:17 / Updated on August 17, 2016 12:24