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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
Structure for Cyproheptadine (DB00434)
- 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
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Symptomatic treatment of Allergic reactions caused by transfusions •••••••••••• Used as adjunct in combination to treat Anaphylaxis Regimen in combination with: Epinephrine (DB00668) •••••••••••• Symptomatic treatment of Angioedema and urticaria •••••••••••• Treatment of Cold urticaria •••••••••••• Treatment of Conjunctivitis allergic caused by food allergy •••••••••••• - Associated Therapies
- Contraindications & Blackbox Warnings
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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.
Target Actions Organism AHistamine H1 receptor antagonistHumans A5-hydroxytryptamine receptor 2A antagonistHumans A5-hydroxytryptamine receptor 2C antagonistHumans UHistamine H2 receptor antagonistHumans U5-hydroxytryptamine receptor 2B antagonistHumans UMuscarinic acetylcholine receptor M1 antagonistHumans UMuscarinic acetylcholine receptor M2 antagonistHumans UMuscarinic acetylcholine receptor M3 antagonistHumans U5-hydroxytryptamine receptor 7 antagonistHumans - 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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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
Pathway Category Cyproheptadine H1-Antihistamine Action Drug 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.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of CNS depression can be increased when Cyproheptadine is combined with 1,2-Benzodiazepine. Acenocoumarol The risk or severity of adverse effects can be increased when Cyproheptadine is combined with Acenocoumarol. Acetazolamide The risk or severity of CNS depression can be increased when Cyproheptadine is combined with Acetazolamide. Acetophenazine The risk or severity of CNS depression can be increased when Cyproheptadine is combined with Acetophenazine. Aclidinium The risk or severity of adverse effects can be increased when Cyproheptadine is combined with Aclidinium. - Food Interactions
- Avoid alcohol. Co-administration with alcohol may potentiate the sedative effects of cyproheptadine.
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.- Product Ingredients
Ingredient UNII CAS InChI Key Cyproheptadine hydrochloride 0S9323MCT0 969-33-5 ZPMVNZLARAEGHB-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
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Cyproheptadine Hydrochloride Tablet 4 mg/1 Oral Boscogen, Inc. 2010-06-15 Not applicable US 
- Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Cyproheptadine Syrup 2 mg/5mL Oral Solubiomix 2018-05-03 2018-06-27 US Cyproheptadine Syrup 2 mg/5mL Oral Pharmaceutical Associates, Inc. 2013-07-29 Not applicable US Cyproheptadine Syrup 2 mg/5mL Oral Chartwell Rx, Llc 2017-07-13 Not applicable US Cyproheptadine Syrup 2 mg/5mL Oral Pharmaceutical Associates, Inc. 2013-07-29 Not applicable US Cyproheptadine Hydrochloride Tablet 4 mg/1 Oral PD-Rx Pharmaceuticals, Inc. 2020-03-01 Not applicable US - Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Euro-cyproheptadine 2mg/5ml Syrup 2 mg / 5 mL Oral Euro Pharm International Canada Inc 2023-11-03 Not applicable Canada 
Euro-cyproheptadine 4 Mg/tablet Tablet 4 mg Oral Euro Pharm International Canada Inc Not applicable Not applicable Canada Jamp Cyproheptadine Syrup Syrup 0.4 mg / mL Oral Jamp Pharma Corporation Not applicable Not applicable Canada Jamp-cyproheptadine Tablet 4 mg Oral Jamp Pharma Corporation 2010-05-03 Not applicable Canada Mar-cyproheptadine Tablet 4 mg Oral Marcan Pharmaceuticals Inc 2023-05-26 Not applicable Canada - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image เคนตามอล Cyproheptadine (1 mg/5mL) + Acetaminophen (120 mg/5mL) + Ammonium chloride (50 mg/5mL) + Sodium citrate (20 mg/5mL) Syrup บริษัท ชาญกิจเทรดดิ้ง จำกัด จำกัด 1987-12-22 Not applicable Thailand 
Categories
- ATC Codes
- R06AX02 — Cyproheptadine
- Drug Categories
- Agents producing tachycardia
- Agents that reduce seizure threshold
- Anti-Allergic Agents
- Anticholinergic Agents
- Antidepressive Agents
- Antihistamines for Systemic Use
- Antipruritics
- Benzocycloheptenes
- Central Nervous System Depressants
- Dermatologicals
- Dibenzocycloheptenes
- Drugs causing inadvertant photosensitivity
- Gastrointestinal Agents
- Histamine Agents
- Histamine Antagonists
- Histamine H1 Antagonists
- Miscellaneous Derivatives
- Muscarinic Antagonists
- Neurotransmitter Agents
- OCT1 inhibitors
- Photosensitizing Agents
- Piperidines
- Potential QTc-Prolonging Agents
- QTc Prolonging Agents
- Serotonin 5-HT2 Receptor Antagonists
- Serotonin 5-HT2A Receptor Antagonists
- Serotonin 5-HT2C Receptor Antagonists
- Serotonin Agents
- Serotonin Receptor Antagonists
- UGT1A3 substrates
- UGT1A4 substrates
- 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[9.4.0.0^{3,8}]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
- 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]
- Simon LV, Keenaghan M: Serotonin Syndrome . [Article]
- 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]
- 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]
- 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]
- 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]
- 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]
- FDA Approved Drug Products: Cyproheptadine hydrochloride tablets for oral use [Link]
- TGA Approved Medications: Periactin (cyproheptadine hydrochloride) tablets for oral use [Link]
- Cayman Chemical: Cyproheptadine MSDS [Link]
- Health Canada Labelling Standard: Cyproheptadine [Link]
- External Links
- Human Metabolome Database
- HMDB0014578
- KEGG Compound
- C06935
- PubChem Compound
- 2913
- PubChem Substance
- 46508613
- ChemSpider
- 2810
- BindingDB
- 50017721
- 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
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 Recruiting Treatment Functional Gastrointestinal Disorders (FGID) 1 somestatus stop reason just information to hide 4 Completed Treatment Attention Deficit and Disruptive Behavior Disorders / Attention Deficit Hyperactivity Disorder (ADHD) / Mental Disorders Diagnosed in Childhood 1 somestatus stop reason just information to hide 4 Completed Treatment Coronavirus Disease 2019 (COVID‑19) / Treatment Efficacy 1 somestatus stop reason just information to hide 4 Terminated Treatment Feeding Behaviors 1 somestatus stop reason just information to hide 4 Unknown Status Treatment Failure to Thrive 1 somestatus stop reason just information to hide
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
Form Route Strength Tablet, sugar coated Oral Syrup Oral 0.04 g Syrup Oral 2 mg/5mL Powder Not applicable 1 g/1g Solution Oral 2 mg/5mL Tablet Oral 4 mg/1 Solution Oral Syrup Oral 0.4 mg / mL Syrup Oral Syrup Oral 40 mg Syrup Oral 2 mg / 5 mL Tablet Oral Tablet, film coated Oral Syrup Oral 240 ml Powder, for solution Oral 0.035 g Elixir Oral Syrup Tablet, sugar coated Oral 2 mg Tablet Oral 2 mg Capsule 4 mg Tablet, sugar coated Oral 4 mg Tablet, coated Oral 2 mg Tablet, film coated Oral 4 mg Tablet Oral 4 mg - Prices
Unit description Cost Unit Cyproheptadine hcl powder 7.34USD g Cyproheptadine HCl 4 mg tablet 0.47USD tablet Cyproheptadine 4 mg tablet 0.43USD tablet Cyproheptadine HCl 2 mg/5ml Syrup 0.16USD ml DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 112.3-113.3 Engelhardt, E.L.; U S . Patent 3,014,911; December 26, 1961; assigned to Merck & Co., Inc. logP 4.69 SANGSTER (1993) - Predicted Properties
Property Value Source Water Solubility 0.0136 mg/mL ALOGPS logP 5.02 ALOGPS logP 4.38 Chemaxon logS -4.3 ALOGPS pKa (Strongest Basic) 8.05 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 0 Chemaxon Refractivity 105.17 m3·mol-1 Chemaxon Polarizability 34.17 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 1.0 Blood Brain Barrier + 0.986 Caco-2 permeable + 0.8038 P-glycoprotein substrate Substrate 0.8598 P-glycoprotein inhibitor I Inhibitor 0.8563 P-glycoprotein inhibitor II Non-inhibitor 0.5315 Renal organic cation transporter Inhibitor 0.8303 CYP450 2C9 substrate Non-substrate 0.8127 CYP450 2D6 substrate Non-substrate 0.6719 CYP450 3A4 substrate Substrate 0.6092 CYP450 1A2 substrate Non-inhibitor 0.9046 CYP450 2C9 inhibitor Non-inhibitor 0.9082 CYP450 2D6 inhibitor Inhibitor 0.8932 CYP450 2C19 inhibitor Non-inhibitor 0.9025 CYP450 3A4 inhibitor Non-inhibitor 0.902 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.5433 Ames test Non AMES toxic 0.9132 Carcinogenicity Non-carcinogens 0.9511 Biodegradation Not ready biodegradable 0.8349 Rat acute toxicity 2.9576 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.5429 hERG inhibition (predictor II) Inhibitor 0.7423
Spectra
- Mass Spec (NIST)
- Download (10 KB)
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 180.3058404 predictedDarkChem Lite v0.1.0 [M-H]- 164.87904 predictedDeepCCS 1.0 (2019) [M+H]+ 180.8230404 predictedDarkChem Lite v0.1.0 [M+H]+ 167.23705 predictedDeepCCS 1.0 (2019) [M+Na]+ 180.4794404 predictedDarkChem Lite v0.1.0 [M+Na]+ 173.33018 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General 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 catecholamine release from adrenal medulla, as well as mediating neurotransmission in the central nervous system
- Specific Function
- G protein-coupled serotonin receptor activity
- Gene Name
- HRH1
- Uniprot ID
- P35367
- Uniprot Name
- Histamine H1 receptor
- Molecular Weight
- 55783.61 Da
References
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
- Paton DM, Webster DR: Clinical pharmacokinetics of H1-receptor antagonists (the antihistamines). Clin Pharmacokinet. 1985 Nov-Dec;10(6):477-97. [Article]
- 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
- Antagonist
- General Function
- G-protein coupled receptor for 5-hydroxytryptamine (serotonin) (PubMed:1330647, PubMed:18703043, PubMed:19057895). Also functions as a receptor for various drugs and psychoactive substances, including mescaline, psilocybin, 1-(2,5-dimethoxy-4-iodophenyl)-2-aminopropane (DOI) and lysergic acid diethylamide (LSD) (PubMed:28129538). Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors (PubMed:28129538). Beta-arrestin family members inhibit signaling via G proteins and mediate activation of alternative signaling pathways (PubMed:28129538). Signaling activates phospholipase C and a phosphatidylinositol-calcium second messenger system that modulates the activity of phosphatidylinositol 3-kinase and promotes the release of Ca(2+) ions from intracellular stores (PubMed:18703043, PubMed:28129538). Affects neural activity, perception, cognition and mood (PubMed:18297054). Plays a role in the regulation of behavior, including responses to anxiogenic situations and psychoactive substances. Plays a role in intestinal smooth muscle contraction, and may play a role in arterial vasoconstriction
- Specific Function
- 1-(4-iodo-2,5-dimethoxyphenyl)propan-2-amine binding
- Gene Name
- HTR2A
- Uniprot ID
- P28223
- Uniprot Name
- 5-hydroxytryptamine receptor 2A
- Molecular Weight
- 52602.58 Da
References
- 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]
- 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]
- 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
- 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
- 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
- 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 differentiation. The activity of this receptor is mediated by G proteins which activate adenylyl cyclase and, through a separate G protein-dependent mechanism, the phosphoinositide/protein kinase (PKC) signaling pathway (By similarity)
- Specific Function
- G protein-coupled serotonin receptor activity
- Gene Name
- HRH2
- Uniprot ID
- P25021
- Uniprot Name
- Histamine H2 receptor
- Molecular Weight
- 40097.65 Da
References
- 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
- Unknown
- Actions
- Antagonist
- General Function
- G-protein coupled receptor for 5-hydroxytryptamine (serotonin) (PubMed:18703043, PubMed:23519210, PubMed:7926008, PubMed:8078486, PubMed:8143856, PubMed:8882600). Also functions as a receptor for various ergot alkaloid derivatives and psychoactive substances (PubMed:12970106, PubMed:18703043, PubMed:23519210, PubMed:23519215, PubMed:24357322, PubMed:28129538, PubMed:7926008, PubMed:8078486, PubMed:8143856). Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors (PubMed:23519215, PubMed:28129538, PubMed:8078486, PubMed:8143856, PubMed:8882600). Beta-arrestin family members inhibit signaling via G proteins and mediate activation of alternative signaling pathways (PubMed:23519215, PubMed:28129538). 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 (PubMed:18703043, PubMed:23519215, PubMed:28129538, PubMed:8078486, PubMed:8143856, PubMed:8882600). Plays a role in the regulation of dopamine and 5-hydroxytryptamine release, 5-hydroxytryptamine uptake and in the regulation of extracellular dopamine and 5-hydroxytryptamine levels, and thereby affects neural activity. May play a role in the perception of pain (By similarity). Plays a role in the regulation of behavior, including impulsive behavior (PubMed:21179162). Required for normal proliferation of embryonic cardiac myocytes and normal heart development. Protects cardiomyocytes against apoptosis. Plays a role in the adaptation of pulmonary arteries to chronic hypoxia. Plays a role in vasoconstriction. Required for normal osteoblast function and proliferation, and for maintaining normal bone density. Required for normal proliferation of the interstitial cells of Cajal in the intestine (By similarity)
- Specific Function
- G protein-coupled serotonin receptor activity
- Gene Name
- HTR2B
- Uniprot ID
- P41595
- Uniprot Name
- 5-hydroxytryptamine receptor 2B
- Molecular Weight
- 54297.41 Da
References
- 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
- The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover
- Specific Function
- G protein-coupled acetylcholine receptor activity
- Gene Name
- CHRM1
- Uniprot ID
- P11229
- Uniprot Name
- Muscarinic acetylcholine receptor M1
- Molecular Weight
- 51420.375 Da
References
- 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
- The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is adenylate cyclase inhibition. Signaling promotes phospholipase C activity, leading to the release of inositol trisphosphate (IP3); this then triggers calcium ion release into the cytosol
- Specific Function
- Arrestin family protein binding
- Gene Name
- CHRM2
- Uniprot ID
- P08172
- Uniprot Name
- Muscarinic acetylcholine receptor M2
- Molecular Weight
- 51714.605 Da
References
- 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
- The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover
- Specific Function
- Acetylcholine binding
- Gene Name
- CHRM3
- Uniprot ID
- P20309
- Uniprot Name
- Muscarinic acetylcholine receptor M3
- Molecular Weight
- 66127.445 Da
References
- 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
- 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 is mediated by G proteins that stimulate adenylate cyclase
- Specific Function
- G protein-coupled serotonin receptor activity
- Gene Name
- HTR7
- Uniprot ID
- P34969
- Uniprot Name
- 5-hydroxytryptamine receptor 7
- Molecular Weight
- 53554.43 Da
References
- 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
- UDP-glucuronosyltransferase (UGT) that catalyzes phase II biotransformation reactions in which lipophilic substrates are conjugated with glucuronic acid to increase the metabolite's water solubility, thereby facilitating excretion into either the urine or bile (PubMed:15472229, PubMed:18674515, PubMed:18719240, PubMed:23288867, PubMed:23756265, PubMed:24641623). Essential for the elimination and detoxification of drugs, xenobiotics and endogenous compounds (PubMed:23756265). Catalyzes the glucuronidation of endogenous estrogen hormones such as estradiol and estrone (PubMed:15472229, PubMed:18719240, PubMed:23288867). Contributes to bile acid (BA) detoxification by catalyzing the glucuronidation of BA substrates, which are natural detergents for dietary lipids absorption (PubMed:23756265). Involved in the glucuronidation of calcidiol, which is the major circulating form of vitamin D3, essential for the regulation of calcium and phosphate homeostasis (PubMed:24641623). Involved in the glucuronidation of the AGTR1 angiotensin receptor antagonists losartan, candesartan and zolarsartan, which can inhibit the effect of angiotensin II (PubMed:18674515)
- Specific Function
- Enzyme binding
- Gene Name
- UGT1A3
- Uniprot ID
- P35503
- Uniprot Name
- UDP-glucuronosyltransferase 1A3
- Molecular Weight
- 60337.835 Da
References
- 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
- UDP-glucuronosyltransferase (UGT) that catalyzes phase II biotransformation reactions in which lipophilic substrates are conjugated with glucuronic acid to increase the metabolite's water solubility, thereby facilitating excretion into either the urine or bile (PubMed:18177842, PubMed:24641623). Essential for the elimination and detoxification of drugs, xenobiotics and endogenous compounds (PubMed:18177842). Involved in the glucuronidation of calcidiol, which is the major circulating form of vitamin D3 essential for the regulation of calcium and phosphate homeostasis (PubMed:24641623). Also glucuronidates the biologically active form of vitamin D3, calcitriol, probably leading to its biliary transport and intestinal reabsorption (PubMed:18177842)
- Specific Function
- Enzyme binding
- Gene Name
- UGT1A4
- Uniprot ID
- P22310
- Uniprot Name
- UDP-glucuronosyltransferase 1A4
- Molecular Weight
- 60024.535 Da
References
- 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
- Udp-glycosyltransferase activity
- Gene Name
- UGT2B10
- Uniprot ID
- P36537
- Uniprot Name
- UDP-glucuronosyltransferase 2B10
- Molecular Weight
- 60773.485 Da
References
- 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
- Binds water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs (Probable). Its main function is the regulation of the colloidal osmotic pressure of blood (Probable). Major zinc transporter in plasma, typically binds about 80% of all plasma zinc (PubMed:19021548). Major calcium and magnesium transporter in plasma, binds approximately 45% of circulating calcium and magnesium in plasma (By similarity). Potentially has more than two calcium-binding sites and might additionally bind calcium in a non-specific manner (By similarity). The shared binding site between zinc and calcium at residue Asp-273 suggests a crosstalk between zinc and calcium transport in the blood (By similarity). The rank order of affinity is zinc > calcium > magnesium (By similarity). Binds to the bacterial siderophore enterobactin and inhibits enterobactin-mediated iron uptake of E.coli from ferric transferrin, and may thereby limit the utilization of iron and growth of enteric bacteria such as E.coli (PubMed:6234017). Does not prevent iron uptake by the bacterial siderophore aerobactin (PubMed:6234017)
- Specific Function
- Antioxidant activity
- Gene Name
- ALB
- Uniprot ID
- P02768
- Uniprot Name
- Albumin
- Molecular Weight
- 69365.94 Da
References
- 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
- Electrogenic voltage-dependent transporter that mediates the transport of a variety of organic cations such as endogenous bioactive amines, cationic drugs and xenobiotics (PubMed:11388889, PubMed:11408531, PubMed:12439218, PubMed:12719534, PubMed:15389554, PubMed:16263091, PubMed:16272756, PubMed:16581093, PubMed:19536068, PubMed:21128598, PubMed:23680637, PubMed:24961373, PubMed:34040533, PubMed:9187257, PubMed:9260930, PubMed:9655880). Functions as a pH- and Na(+)-independent, bidirectional transporter (By similarity). Cation cellular uptake or release is driven by the electrochemical potential (i.e. membrane potential and concentration gradient) and substrate selectivity (By similarity). Hydrophobicity is a major requirement for recognition in polyvalent substrates and inhibitors (By similarity). Primarily expressed at the basolateral membrane of hepatocytes and proximal tubules and involved in the uptake and disposition of cationic compounds by hepatic and renal clearance from the blood flow (By similarity). Most likely functions as an uptake carrier in enterocytes contributing to the intestinal elimination of organic cations from the systemic circulation (PubMed:16263091). Transports endogenous monoamines such as N-1-methylnicotinamide (NMN), guanidine, histamine, neurotransmitters dopamine, serotonin and adrenaline (PubMed:12439218, PubMed:24961373, PubMed:35469921, PubMed:9260930). Also transports natural polyamines such as spermidine, agmatine and putrescine at low affinity, but relatively high turnover (PubMed:21128598). Involved in the hepatic uptake of vitamin B1/thiamine, hence regulating hepatic lipid and energy metabolism (PubMed:24961373). Mediates the bidirectional transport of acetylcholine (ACh) at the apical membrane of ciliated cell in airway epithelium, thereby playing a role in luminal release of ACh from bronchial epithelium (PubMed:15817714). Transports dopaminergic neuromodulators cyclo(his-pro) and salsolinol with lower efficency (PubMed:17460754). Also capable of transporting non-amine endogenous compounds such as prostaglandin E2 (PGE2) and prostaglandin F2-alpha (PGF2-alpha) (PubMed:11907186). May contribute to the transport of cationic compounds in testes across the blood-testis-barrier (Probable). Also involved in the uptake of xenobiotics tributylmethylammonium (TBuMA), quinidine, N-methyl-quinine (NMQ), N-methyl-quinidine (NMQD) N-(4,4-azo-n-pentyl)-quinuclidine (APQ), azidoprocainamide methoiodide (AMP), N-(4,4-azo-n-pentyl)-21-deoxyajmalinium (APDA) and 4-(4-(dimethylamino)styryl)-N-methylpyridinium (ASP) (PubMed:11408531, PubMed:15389554, PubMed:35469921, PubMed:9260930)
- Specific Function
- (r)-carnitine transmembrane transporter activity
- Gene Name
- SLC22A1
- Uniprot ID
- O15245
- Uniprot Name
- Solute carrier family 22 member 1
- Molecular Weight
- 61153.345 Da
References
- 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 at June 13, 2005 13:24 / Updated at September 07, 2024 17:41