Cyproheptadine

Identification

Summary

Cyproheptadine is a combined serotonin and histamine antagonist used in the treatment of allergic symptoms, for appetite stimulation, and off-label in the treatment of serotonin syndrome.

Generic Name
Cyproheptadine
DrugBank Accession Number
DB00434
Background

Cyproheptadine is a potent competitive antagonist of both serotonin and histamine receptors.8 It is used primarily to treat allergic symptoms, though it is perhaps more notable for its use in appetite stimulation11 and its off-label use in the treatment of serotonin syndrome.2

Type
Small Molecule
Groups
Approved
Structure
Thumb
Weight
Average: 287.3981
Monoisotopic: 287.167399677
Chemical Formula
C21H21N
Synonyms
  • 1-methyl-4-(5-dibenzo(a,e)cycloheptatrienylidene)piperidine
  • 1-Methyl-4-(5H-dibenzo(a,d)cycloheptenylidene)piperidine
  • 4-(5-dibenzo(a,d)cyclohepten-5-ylidine)-1-methylpiperidine
  • 4-(5H-dibenzo(a,d)cyclohepten-5-ylidene)-1-methylpiperidine
  • 4-Dibenzo[a,d]cyclohepten-5-ylidene-1-methyl-piperidine
  • 5-(1-methylpiperidylidene-4)-5H-dibenzo(a,d)cyclopheptene
  • Ciproheptadina
  • Cyproheptadin
  • Cyproheptadine
  • Cyproheptadinum
External IDs
  • Fl 5967
  • HSp 1229

Pharmacology

Indication

In the US, prescription cyproheptadine is indicated for the treatment of various allergic symptomatologies - including dermatographia, rhinitis, conjunctivitis, and urticaria - as well as adjunctive therapy in the management of anaphylaxis following treatment with epinephrine.8 In Canada, cyproheptadine is available over-the-counter and is indicated for the treatment of pruritus and for appetite stimulation.11 In Australia, cyproheptadine is additionally indicated for the treatment vascular headaches.9

Cyproheptadine is also used off-label for the treatment of serotonin syndrome.2

Pharmacology
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Associated Conditions
Associated Therapies
Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Cyproheptadine has been observed to antagonize several pharmacodynamic effects of serotonin in laboratory animals, including bronchoconstriction and vasodepression, and has demonstrated similar efficacy in antagonizing histamine-mediated effects.9 The reason for its efficacy in preventing anaphylactic shock has not been elucidated, but appears to be related to its anti-serotonergic effects.9

Mechanism of action

Cyproheptadine appears to exert its antihistamine and antiserotonin effects by competing with free histamine and serotonin for binding at their respective receptors.9 Antagonism of serotonin on the appetite center of the hypothalamus may account for cyproheptadine's ability to stimulate the appetite.

TargetActionsOrganism
AHistamine H1 receptor
antagonist
Humans
UHistamine H2 receptor
antagonist
Humans
A5-hydroxytryptamine receptor 2A
antagonist
Humans
U5-hydroxytryptamine receptor 2B
antagonist
Humans
A5-hydroxytryptamine receptor 2C
antagonist
Humans
UMuscarinic acetylcholine receptor M1
antagonist
Humans
UMuscarinic acetylcholine receptor M2
antagonist
Humans
UMuscarinic acetylcholine receptor M3
antagonist
Humans
U5-hydroxytryptamine receptor 7
antagonist
Humans
Absorption

A single study examining the difference in absorption of orally administered versus sublingually administered cyproheptadine in five healthy males demonstrated a mean Cmax of 30.0 mcg/L and 4.0 mcg/L, respectively, and a mean AUC of 209 mcg.h/L and 25 mcg.h/L, respectively.7 The Tmax of orally and sublingually administered cyproheptadine was 4 hours and 9.6 hours, respectively.7

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

The principal metabolite found in human urine has been identified as a quaternary ammonium glucuronide conjugate of cyproheptadine.8

Hover over products below to view reaction partners

Route of elimination

Approximately 2-20% of the radioactivity from an orally administered radio-labeled dose of cyproheptadine is excreted in the feces, of which approximately 34% is unchanged parent drug (less than 5.7% of the total dose).9 At least 40% of radioactivity is recovered in the urine.9

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Overdosage with cyproheptadine is likely to result in significant sedation - although paradoxical stimulation has been noted in pediatric patients - and anticholinergic adverse effects such as dry mouth and flushing.8 Most patients appear to recover without incident, as a review of cyproheptadine overdose cases in Hong Kong found the majority of patients had no or mild symptoms following intentional overdose.6

In the event of overdosage with cyproheptadine, prescribing information recommends the induction of vomiting (if it has not occurred spontaneously) using syrup of ipecac.8 Gastric lavage and activated charcoal may also be considered. Vasopressors may be used to treat hypotension and intravenous physostigmine salicylate may be considered for the treatment of significant CNS symptoms depending on the clinical picture.8

Pathways
PathwayCategory
Cyproheptadine H1-Antihistamine ActionDrug action
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.
DrugInteraction
1,2-Benzodiazepine1,2-Benzodiazepine may increase the central nervous system depressant (CNS depressant) activities of Cyproheptadine.
AcenocoumarolThe risk or severity of adverse effects can be increased when Cyproheptadine is combined with Acenocoumarol.
AcetazolamideAcetazolamide may increase the central nervous system depressant (CNS depressant) activities of Cyproheptadine.
AcetophenazineAcetophenazine may increase the central nervous system depressant (CNS depressant) activities of Cyproheptadine.
AclidiniumThe risk or severity of adverse effects can be increased when Cyproheptadine is combined with Aclidinium.
AcrivastineThe risk or severity of QTc prolongation can be increased when Cyproheptadine is combined with Acrivastine.
AdenosineThe risk or severity of QTc prolongation can be increased when Cyproheptadine is combined with Adenosine.
AgomelatineThe risk or severity of adverse effects can be increased when Cyproheptadine is combined with Agomelatine.
AjmalineThe risk or severity of QTc prolongation can be increased when Cyproheptadine is combined with Ajmaline.
AlfentanilThe risk or severity of adverse effects can be increased when Alfentanil is combined with Cyproheptadine.
Interactions
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Food Interactions
  • Avoid alcohol. Co-administration with alcohol may potentiate the sedative effects of cyproheptadine.

Products

Products
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Product Ingredients
IngredientUNIICASInChI Key
Cyproheptadine hydrochloride0S9323MCT0969-33-5ZPMVNZLARAEGHB-UHFFFAOYSA-N
Product Images
International/Other Brands
Apeplus (Radicura) / Apitup (Universal) / Biohept (Biofarm) / Ciplactin (Cipla) / Cipractine (Teriak) / Ciproheptadina (Arena) / Ciprovit / Ciptadine (IBN) / Cyheptine (Greater Pharma) / Cyllermin (CCPC) / Periactin (Merck) / Periactine (Teofarma) / Periatin (Apex) / Reactin (Orion)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Cyproheptadine HydrochlorideTablet4 mg/1OralBoscogen, Inc.2010-06-15Not applicableUS flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
CyproheptadineSyrup2 mg/5mLOralSolubiomix2018-05-032018-06-27US flag
CyproheptadineSyrup2 mg/5mLOralPharmaceutical Associates, Inc.2013-07-29Not applicableUS flag
CyproheptadineSyrup2 mg/5mLOralPharmaceutical Associates, Inc.2013-07-29Not applicableUS flag
Cyproheptadine HydrochlorideSyrup2 mg/5mLOralPhysicians Total Care, Inc.2009-07-31Not applicableUS flag
Cyproheptadine HydrochlorideTablet4 mg/1Oralbryant ranch prepack2017-07-20Not applicableUS flag
Cyproheptadine HydrochlorideTablet4 mg/1Oralbryant ranch prepack2018-04-11Not applicableUS flag
Cyproheptadine HydrochlorideTablet4 mg/1OralMarlex Pharmaceuticals Inc2018-01-01Not applicableUS flag
Cyproheptadine HydrochlorideTablet4 mg/1OralREMEDYREPACK INC.2016-08-162017-11-28US flag
Cyproheptadine HydrochlorideTablet4 mg/1OralCorePharma, LLC2015-07-292020-02-01US flag
Cyproheptadine HydrochlorideTablet4 mg/1OralAppco Pharma Llc2016-12-142017-01-16US flag
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Euro-cyproheptadine 2mg/5mlSyrup2 mg / 5 mLOralEuro Pharm International Canada IncNot applicableNot applicableCanada flag
Euro-cyproheptadine 4 Mg/tabletTablet4 mgOralEuro Pharm International Canada IncNot applicableNot applicableCanada flag
Jamp Cyproheptadine SyrupSyrup0.4 mg / mLOralJamp Pharma CorporationNot applicableNot applicableCanada flag
Jamp-cyproheptadineTablet4 mgOralJamp Pharma Corporation2010-05-03Not applicableCanada flag
Periactin Syr 2mg/5mlSyrup2 mg / 5 mLOralMerck Frosst Canada & Cie, Merck Frosst Canada & Co.1961-12-312002-07-29Canada flag
Periactin Tab 4mgTablet4 mgOralMerck Frosst Canada & Cie, Merck Frosst Canada & Co.1961-12-312002-07-29Canada flag
PMS-cyproheptadine HCl Tab 4mgTablet4 mgOralPharmascience Inc1996-10-16Not applicableCanada flag
Sandoz CyproheptadineSyrup2 mg / 5 mLOralSandoz Canada Incorporated2003-05-272021-02-22Canada flag
Sandoz Cyproheptadine TabletTablet4 mgOralSandoz Canada Incorporated2006-06-052019-11-25Canada flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
เคนตามอลCyproheptadine (1 mg/5mL) + Acetaminophen (120 mg/5mL) + Ammonium chloride (50 mg/5mL) + Sodium citrate (20 mg/5mL)Syrupบริษัท ชาญกิจเทรดดิ้ง จำกัด จำกัด1987-12-22Not applicableThailand flag

Categories

ATC Codes
R06AX02 — Cyproheptadine
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as dibenzocycloheptenes. These are compounds containing a dibenzocycloheptene moiety, which consists of two benzene rings connected by a cycloheptene ring.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Dibenzocycloheptenes
Sub Class
Not Available
Direct Parent
Dibenzocycloheptenes
Alternative Parents
Piperidines / Trialkylamines / Azacyclic compounds / Organopnictogen compounds / Hydrocarbon derivatives
Substituents
Amine / Aromatic heteropolycyclic compound / Azacycle / Dibenzocycloheptene / Hydrocarbon derivative / Organic nitrogen compound / Organoheterocyclic compound / Organonitrogen compound / Organopnictogen compound / Piperidine
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
piperidines, tertiary amine (CHEBI:4046)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
2YHB6175DO
CAS number
129-03-3
InChI Key
JJCFRYNCJDLXIK-UHFFFAOYSA-N
InChI
InChI=1S/C21H21N/c1-22-14-12-18(13-15-22)21-19-8-4-2-6-16(19)10-11-17-7-3-5-9-20(17)21/h2-11H,12-15H2,1H3
IUPAC Name
1-methyl-4-{tricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,9,11,13-heptaen-2-ylidene}piperidine
SMILES
CN1CCC(CC1)=C1C2=CC=CC=C2C=CC2=CC=CC=C12

References

Synthesis Reference

Engelhardt, E.L.; U S . Patent 3,014,911; December 26, 1961; assigned to Merck & Co., Inc.

General References
  1. Tokunaga S, Takeda Y, Shinomiya K, Hirase M, Kamei C: Effects of some H1-antagonists on the sleep-wake cycle in sleep-disturbed rats. J Pharmacol Sci. 2007 Feb;103(2):201-6. Epub 2007 Feb 8. [Article]
  2. Simon LV, Keenaghan M: Serotonin Syndrome . [Article]
  3. Milani N, Qiu N, Molitor B, Badee J, Cruciani G, Fowler S: Use of Phenotypically Poor Metabolizer Individual Donor Human Liver Microsomes To Identify Selective Substrates of UGT2B10. Drug Metab Dispos. 2020 Mar;48(3):176-186. doi: 10.1124/dmd.119.089482. Epub 2019 Dec 15. [Article]
  4. Kato S, Shah A, Plesescu M, Miyata Y, Bolleddula J, Chowdhury S, Zhu X: Prediction of Human Disproportionate and Biliary Excreted Metabolites Using Chimeric Mice with Humanized Liver. Drug Metab Dispos. 2020 Oct;48(10):934-943. doi: 10.1124/dmd.120.000128. Epub 2020 Jul 14. [Article]
  5. Porter CC, Arison BH, Gruber VF, Titus DC, Vandenheuvel WJ: Human metabolism of cyproheptadine. Drug Metab Dispos. 1975 May-Jun;3(3):189-97. [Article]
  6. Chu FK: Review of the epidemiology and characteristics of intentional cyproheptadine overdose in Hong Kong. Clin Toxicol (Phila). 2011 Aug;49(7):681-3. doi: 10.3109/15563650.2011.602085. Epub 2011 Aug 8. [Article]
  7. Gunja N, Collins M, Graudins A: A comparison of the pharmacokinetics of oral and sublingual cyproheptadine. J Toxicol Clin Toxicol. 2004;42(1):79-83. doi: 10.1081/clt-120028749. [Article]
  8. FDA Approved Drug Products: Cyproheptadine hydrochloride tablets for oral use [Link]
  9. TGA Approved Medications: Periactin (cyproheptadine hydrochloride) tablets for oral use [Link]
  10. Cayman Chemical: Cyproheptadine MSDS [Link]
  11. Health Canada Labelling Standard: Cyproheptadine [Link]
Human Metabolome Database
HMDB0014578
KEGG Compound
C06935
PubChem Compound
2913
PubChem Substance
46508613
ChemSpider
2810
BindingDB
50017721
RxNav
3013
ChEBI
4046
ChEMBL
CHEMBL516
ZINC
ZINC000000968264
Therapeutic Targets Database
DAP000103
PharmGKB
PA164749366
Guide to Pharmacology
GtP Drug Page
PDBe Ligand
C7H
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Cyproheptadine
PDB Entries
5ayf
MSDS
Download (74.3 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedTreatmentAttention Deficit and Disruptive Behavior Disorders / Attention Deficit Hyperactivity Disorder (ADHD) / Mental Disorders Diagnosed in Childhood1
4TerminatedTreatmentFeeding Behaviors1
4Unknown StatusTreatmentFailure to Thrive1
3Not Yet RecruitingTreatmentCoronavirus Disease 2019 (COVID‑19) / Platelets Dysfunction / Serotonin Syndrome / Viral Pneumonia1
3TerminatedSupportive CareMalignancies1
2CompletedSupportive CareCachexia / Leukemias / Malignant Lymphomas / Myelodysplastic Syndromes (MDS) / Myelodysplastic/Myeloproliferative Diseases / Neoplasms, Brain / Tumors of the Central Nervous System / Unspecified Childhood Solid Tumor, Protocol Specific1
2CompletedTreatmentAlcohol Dependency1
2Not Yet RecruitingTreatmentCoronavirus Disease 2019 (COVID‑19) / COVID-19 Pneumonia / Platelets Dysfunction / Serotonin Syndrome / Viral Pneumonia1
2RecruitingTreatmentAlcohol Use Disorders (AUD)1
2TerminatedSupportive CareLeukemias / Malignant Lymphomas / Malnutrition / Myelodysplastic Syndromes (MDS) / Unspecified Childhood Solid Tumor, Protocol Specific / Weight Changes1

Pharmacoeconomics

Manufacturers
  • Merck and co inc
Packagers
  • Actavis Group
  • Amerisource Health Services Corp.
  • Apotheca Inc.
  • Atlantic Biologicals Corporation
  • Bryant Ranch Prepack
  • Cardinal Health
  • Chestertown Home Medical Supplies
  • Corepharma LLC
  • Cypress Pharmaceutical Inc.
  • Dept Health Central Pharmacy
  • Direct Dispensing Inc.
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • Emcure Pharmaceuticals Ltd.
  • Heartland Repack Services LLC
  • Ivax Pharmaceuticals
  • Lake Erie Medical and Surgical Supply
  • Lyne Laboratories Inc.
  • Major Pharmaceuticals
  • Medisca Inc.
  • Murfreesboro Pharmaceutical Nursing Supply
  • Palmetto Pharmaceuticals Inc.
  • Par Pharmaceuticals
  • PCA LLC
  • PD-Rx Pharmaceuticals Inc.
  • Physicians Total Care Inc.
  • Pliva Inc.
  • Prepak Systems Inc.
  • Qualitest
  • Remedy Repack
  • Resource Optimization and Innovation LLC
  • Rising Pharmaceuticals
  • Southwood Pharmaceuticals
  • Stason Pharmaceuticals Inc.
  • Teva Pharmaceutical Industries Ltd.
  • Tya Pharmaceuticals
  • Vangard Labs Inc.
Dosage Forms
FormRouteStrength
SyrupOral0.04 g
SyrupOral2 mg/5mL
PowderNot applicable1 g/1g
SolutionOral2 mg/5mL
TabletOral4 mg/1
Tablet, sugar coatedOral
SyrupOral0.4 mg / mL
SyrupOral
SyrupOral40 mg
SyrupOral2 mg / 5 mL
TabletOral
Tablet, film coatedOral
Powder, for solutionOral0.035 g
ElixirOral
Syrup
Tablet, sugar coatedOral2 mg
TabletOral2 mg
Capsule4 mg
Tablet, sugar coatedOral4 mg
Tablet, coatedOral2 mg
Tablet, film coatedOral4 mg
TabletOral4 mg
Prices
Unit descriptionCostUnit
Cyproheptadine hcl powder7.34USD g
Cyproheptadine HCl 4 mg tablet0.47USD tablet
Cyproheptadine 4 mg tablet0.43USD tablet
Cyproheptadine HCl 2 mg/5ml Syrup0.16USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)112.3-113.3Engelhardt, E.L.; U S . Patent 3,014,911; December 26, 1961; assigned to Merck & Co., Inc.
logP4.69SANGSTER (1993)
Predicted Properties
PropertyValueSource
Water Solubility0.0136 mg/mLALOGPS
logP5.02ALOGPS
logP4.38ChemAxon
logS-4.3ALOGPS
pKa (Strongest Basic)8.05ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area3.24 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity105.17 m3·mol-1ChemAxon
Polarizability34.17 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.986
Caco-2 permeable+0.8038
P-glycoprotein substrateSubstrate0.8598
P-glycoprotein inhibitor IInhibitor0.8563
P-glycoprotein inhibitor IINon-inhibitor0.5315
Renal organic cation transporterInhibitor0.8303
CYP450 2C9 substrateNon-substrate0.8127
CYP450 2D6 substrateNon-substrate0.6719
CYP450 3A4 substrateSubstrate0.6092
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 inhibitorNon-inhibitor0.9082
CYP450 2D6 inhibitorInhibitor0.8932
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.902
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.5433
Ames testNon AMES toxic0.9132
CarcinogenicityNon-carcinogens0.9511
BiodegradationNot ready biodegradable0.8349
Rat acute toxicity2.9576 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.5429
hERG inhibition (predictor II)Inhibitor0.7423
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (10 KB)
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Mass Spectrum (Electron Ionization)MSsplash10-00kr-2290000000-a17c27a9f171b058f2c3
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
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-000i-0290000000-964629904e89d79568d8

Targets

Drugtargets
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Details
1. Histamine H1 receptor
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
General Function
Histamine receptor activity
Specific Function
In peripheral tissues, the H1 subclass of histamine receptors mediates the contraction of smooth muscles, increase in capillary permeability due to contraction of terminal venules, and catecholamin...
Gene Name
HRH1
Uniprot ID
P35367
Uniprot Name
Histamine H1 receptor
Molecular Weight
55783.61 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
  2. Paton DM, Webster DR: Clinical pharmacokinetics of H1-receptor antagonists (the antihistamines). Clin Pharmacokinet. 1985 Nov-Dec;10(6):477-97. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
Histamine receptor activity
Specific Function
The H2 subclass of histamine receptors mediates gastric acid secretion. Also appears to regulate gastrointestinal motility and intestinal secretion. Possible role in regulating cell growth and diff...
Gene Name
HRH2
Uniprot ID
P25021
Uniprot Name
Histamine H2 receptor
Molecular Weight
40097.65 Da
References
  1. Green JP, Weinstein H, Maayani S: Defining the histamine H2-receptor in brain: the interaction with LSD. NIDA Res Monogr. 1978;(22):38-59. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
General Function
Virus receptor activity
Specific Function
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances, including mescaline, psilocybin, 1-(2,5-dimethoxy-4-iodop...
Gene Name
HTR2A
Uniprot ID
P28223
Uniprot Name
5-hydroxytryptamine receptor 2A
Molecular Weight
52602.58 Da
References
  1. Honda M, Nishida T, Ono H: Tricyclic analogs cyclobenzaprine, amitriptyline and cyproheptadine inhibit the spinal reflex transmission through 5-HT(2) receptors. Eur J Pharmacol. 2003 Jan 1;458(1-2):91-9. [Article]
  2. Callaway CW, Rempel N, Peng RY, Geyer MA: Serotonin 5-HT1-like receptors mediate hyperactivity in rats induced by 3,4-methylenedioxymethamphetamine. Neuropsychopharmacology. 1992 Sep;7(2):113-27. [Article]
  3. Calka O, Metin A, Dulger H, Erkoc R: Effect of cyproheptadine on serum leptin levels. Adv Ther. 2005 Sep-Oct;22(5):424-8. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
Serotonin receptor activity
Specific Function
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various ergot alkaloid derivatives and psychoactive substances. Ligand binding causes a conformation...
Gene Name
HTR2B
Uniprot ID
P41595
Uniprot Name
5-hydroxytryptamine receptor 2B
Molecular Weight
54297.41 Da
References
  1. Honda M, Nishida T, Ono H: Tricyclic analogs cyclobenzaprine, amitriptyline and cyproheptadine inhibit the spinal reflex transmission through 5-HT(2) receptors. Eur J Pharmacol. 2003 Jan 1;458(1-2):91-9. [Article]
Kind
Protein
Organism
Humans
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. Honda M, Nishida T, Ono H: Tricyclic analogs cyclobenzaprine, amitriptyline and cyproheptadine inhibit the spinal reflex transmission through 5-HT(2) receptors. Eur J Pharmacol. 2003 Jan 1;458(1-2):91-9. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
Phosphatidylinositol phospholipase c activity
Specific Function
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the...
Gene Name
CHRM1
Uniprot ID
P11229
Uniprot Name
Muscarinic acetylcholine receptor M1
Molecular Weight
51420.375 Da
References
  1. Eltze M, Lambrecht G, Mutschler E: Cyproheptadine displays high affinity for muscarinic receptors but does not discriminate between receptor subtypes. Eur J Pharmacol. 1989 Dec 7;173(2-3):219-22. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
G-protein coupled acetylcholine receptor activity
Specific Function
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the...
Gene Name
CHRM2
Uniprot ID
P08172
Uniprot Name
Muscarinic acetylcholine receptor M2
Molecular Weight
51714.605 Da
References
  1. Eltze M, Lambrecht G, Mutschler E: Cyproheptadine displays high affinity for muscarinic receptors but does not discriminate between receptor subtypes. Eur J Pharmacol. 1989 Dec 7;173(2-3):219-22. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
Receptor activity
Specific Function
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the...
Gene Name
CHRM3
Uniprot ID
P20309
Uniprot Name
Muscarinic acetylcholine receptor M3
Molecular Weight
66127.445 Da
References
  1. Eltze M, Lambrecht G, Mutschler E: Cyproheptadine displays high affinity for muscarinic receptors but does not discriminate between receptor subtypes. Eur J Pharmacol. 1989 Dec 7;173(2-3):219-22. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
Serotonin receptor activity
Specific Function
This is one of the several different receptors for 5-hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor ...
Gene Name
HTR7
Uniprot ID
P34969
Uniprot Name
5-hydroxytryptamine receptor 7
Molecular Weight
53554.43 Da
References
  1. Teitler M, Toohey N, Knight JA, Klein MT, Smith C: Clozapine and other competitive antagonists reactivate risperidone-inactivated h5-HT7 receptors: radioligand binding and functional evidence for GPCR homodimer protomer interactions. Psychopharmacology (Berl). 2010 Dec;212(4):687-97. doi: 10.1007/s00213-010-2001-x. Epub 2010 Sep 9. [Article]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Retinoic acid binding
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Isoform 2 lacks transferase activity but acts as a negative reg...
Gene Name
UGT1A3
Uniprot ID
P35503
Uniprot Name
UDP-glucuronosyltransferase 1-3
Molecular Weight
60337.835 Da
References
  1. Green MD, King CD, Mojarrabi B, Mackenzie PI, Tephly TR: Glucuronidation of amines and other xenobiotics catalyzed by expressed human UDP-glucuronosyltransferase 1A3. Drug Metab Dispos. 1998 Jun;26(6):507-12. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Protein homodimerization activity
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the...
Gene Name
UGT1A4
Uniprot ID
P22310
Uniprot Name
UDP-glucuronosyltransferase 1-4
Molecular Weight
60024.535 Da
References
  1. Green MD, Bishop WP, Tephly TR: Expressed human UGT1.4 protein catalyzes the formation of quaternary ammonium-linked glucuronides. Drug Metab Dispos. 1995 Mar;23(3):299-302. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.
Specific Function
Glucuronosyltransferase activity
Gene Name
UGT2B10
Uniprot ID
P36537
Uniprot Name
UDP-glucuronosyltransferase 2B10
Molecular Weight
60773.485 Da
References
  1. Milani N, Qiu N, Molitor B, Badee J, Cruciani G, Fowler S: Use of Phenotypically Poor Metabolizer Individual Donor Human Liver Microsomes To Identify Selective Substrates of UGT2B10. Drug Metab Dispos. 2020 Mar;48(3):176-186. doi: 10.1124/dmd.119.089482. Epub 2019 Dec 15. [Article]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. Jiang H, Chen R, Wang H, Pu H: Interaction of cyproheptadine hydrochloride with human serum albumin using spectroscopy and molecular modeling methods. Luminescence. 2013 Mar-Apr;28(2):244-52. doi: 10.1002/bio.2374. Epub 2012 May 18. [Article]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Secondary active organic cation transmembrane transporter activity
Specific Function
Translocates a broad array of organic cations with various structures and molecular weights including the model compounds 1-methyl-4-phenylpyridinium (MPP), tetraethylammonium (TEA), N-1-methylnico...
Gene Name
SLC22A1
Uniprot ID
O15245
Uniprot Name
Solute carrier family 22 member 1
Molecular Weight
61153.345 Da
References
  1. Badolo L, Rasmussen LM, Hansen HR, Sveigaard C: Screening of OATP1B1/3 and OCT1 inhibitors in cryopreserved hepatocytes in suspension. Eur J Pharm Sci. 2010 Jul 11;40(4):282-8. doi: 10.1016/j.ejps.2010.03.023. Epub 2010 Apr 8. [Article]

Drug created on June 13, 2005 13:24 / Updated on July 29, 2021 06:27