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

Similar Structures

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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Associated Conditions

Associated Therapies

Appetite stimulation

Contraindications & Blackbox Warnings

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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.

Target	Actions	Organism
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 C_max 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 T_max 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

Cyproheptadine
- Cyproheptadine N-glucuronide

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

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
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1,2-Benzodiazepine	1,2-Benzodiazepine may increase the central nervous system depressant (CNS depressant) activities of Cyproheptadine.
Acenocoumarol	The risk or severity of adverse effects can be increased when Cyproheptadine is combined with Acenocoumarol.
Acetazolamide	Acetazolamide may increase the central nervous system depressant (CNS depressant) activities of Cyproheptadine.
Acetophenazine	Acetophenazine may increase the central nervous system depressant (CNS depressant) activities of Cyproheptadine.
Aclidinium	The risk or severity of adverse effects can be increased when Cyproheptadine is combined with Aclidinium.
Acrivastine	The risk or severity of QTc prolongation can be increased when Cyproheptadine is combined with Acrivastine.
Adenosine	The risk or severity of QTc prolongation can be increased when Cyproheptadine is combined with Adenosine.
Agomelatine	Agomelatine may increase the central nervous system depressant (CNS depressant) activities of Cyproheptadine.
Ajmaline	The risk or severity of QTc prolongation can be increased when Cyproheptadine is combined with Ajmaline.
Alfentanil	The risk or severity of adverse effects can be increased when Cyproheptadine is combined with Alfentanil.

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Food Interactions

Avoid alcohol. Co-administration with alcohol may potentiate the sedative effects of cyproheptadine.

Products

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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

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Cyproheptadine	Syrup	2 mg/5mL	Oral	Pharmaceutical Associates, Inc.	2013-07-29	Not applicable
Cyproheptadine	Syrup	2 mg/5mL	Oral	Pharmaceutical Associates, Inc.	2013-07-29	Not applicable
Cyproheptadine	Syrup	2 mg/5mL	Oral	Solubiomix	2018-05-03	2018-06-27
Cyproheptadine Hydrochloride	Tablet	4 mg/1	Oral	AvPAK	2021-03-22	Not applicable
Cyproheptadine Hydrochloride	Tablet	4 mg/1	Oral	Ingenus Pharmaceuticals Nj, Llc	2015-09-23	2017-12-14
Cyproheptadine Hydrochloride	Tablet	4 mg/1	Oral	State of Florida DOH Central Pharmacy	2009-07-01	Not applicable
Cyproheptadine Hydrochloride	Tablet	4 mg/1	Oral	Cadila Healthcare Limited	2017-07-20	Not applicable
Cyproheptadine Hydrochloride	Tablet	4 mg/1	Oral	bryant ranch prepack	2017-07-20	Not applicable
Cyproheptadine Hydrochloride	Tablet	4 mg/1	Oral	Golden State Medical Supply	2016-12-29	Not applicable
Cyproheptadine Hydrochloride	Tablet	4 mg/1	Oral	Alexso, Inc	2015-09-23	Not applicable

Over the Counter Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Euro-cyproheptadine 2mg/5ml	Syrup	2 mg / 5 mL	Oral	Euro Pharm International Canada Inc	Not applicable	Not applicable
Euro-cyproheptadine 4 Mg/tablet	Tablet	4 mg	Oral	Euro Pharm International Canada Inc	Not applicable	Not applicable
Jamp Cyproheptadine Syrup	Syrup	0.4 mg / mL	Oral	Jamp Pharma Corporation	Not applicable	Not applicable
Jamp-cyproheptadine	Tablet	4 mg	Oral	Jamp Pharma Corporation	2010-05-03	Not applicable
Periactin Syr 2mg/5ml	Syrup	2 mg / 5 mL	Oral	Merck Frosst Canada & Cie, Merck Frosst Canada & Co.	1961-12-31	2002-07-29
Periactin Tab 4mg	Tablet	4 mg	Oral	Merck Frosst Canada & Cie, Merck Frosst Canada & Co.	1961-12-31	2002-07-29
PILIAN TABLET 4 mg	Tablet	4 mg	Oral	YUNG SHIN PHARMACEUTICAL (SINGAPORE) PTE LTD	1991-10-22	Not applicable
PMS-cyproheptadine HCl Tab 4mg	Tablet	4 mg	Oral	Pharmascience Inc	1996-10-16	Not applicable
Sandoz Cyproheptadine	Syrup	2 mg / 5 mL	Oral	Sandoz Canada Incorporated	2003-05-27	2021-02-22
Sandoz Cyproheptadine Tablet	Tablet	4 mg	Oral	Sandoz Canada Incorporated	2006-06-05	2019-11-25

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

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

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
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

Phase	Status	Purpose	Conditions	Count
4	Completed	Treatment	Attention Deficit and Disruptive Behavior Disorders / Attention Deficit Hyperactivity Disorder (ADHD) / Mental Disorders Diagnosed in Childhood	1
4	Terminated	Treatment	Feeding Behaviors	1
4	Unknown Status	Treatment	Failure to Thrive	1
3	Not Yet Recruiting	Treatment	Coronavirus Disease 2019 (COVID‑19) / Platelets Dysfunction / Serotonin Syndrome / Viral Pneumonia	1
3	Recruiting	Treatment	Coronavirus Disease 2019 (COVID‑19) / COVID-19 Pneumonia	1
3	Terminated	Supportive Care	Malignancies	1
2	Active Not Recruiting	Treatment	Alcohol Use Disorders (AUD)	1
2	Completed	Supportive Care	Cachexia / Leukemias / Malignant Lymphomas / Myelodysplastic Syndromes (MDS) / Myelodysplastic/Myeloproliferative Diseases / Neoplasms, Brain / Tumors of the Central Nervous System / Unspecified Childhood Solid Tumor, Protocol Specific	1
2	Completed	Treatment	Alcohol Dependency	1
2	Not Yet Recruiting	Treatment	Coronavirus Disease 2019 (COVID‑19) / COVID-19 Pneumonia / Platelets Dysfunction / Serotonin Syndrome / Viral Pneumonia	1

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
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
Tablet, sugar coated	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
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

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Download (10 KB)

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	Not Available
Mass Spectrum (Electron Ionization)	MS	splash10-00kr-2290000000-a17c27a9f171b058f2c3
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
LC-MS/MS Spectrum - LC-ESI-qTof , Positive	LC-MS/MS	Not Available
MS/MS Spectrum - , positive	LC-MS/MS	splash10-000i-0290000000-964629904e89d79568d8

Targets

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Property	Measurement	pH	Temperature (°C)	References
Kd (nM)	5400	N/A	N/A	A27481
Ki (nM)	0.06	N/A	N/A	A28219

Details1. 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

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]

Details2. Histamine H2 receptor

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

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]

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	0.46	N/A	N/A	A18191 / A28059
Ki (nM)	1.6	N/A	N/A	A28220
Ki (nM)	2.88	N/A	N/A	A27484
Ki (nM)	3	N/A	N/A	A18179

Details3. 5-hydroxytryptamine receptor 2A

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

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]

Details4. 5-hydroxytryptamine receptor 2B

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

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]

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	11	N/A	N/A	A18179
Ki (nM)	2.23	N/A	N/A	A18191

Details5. 5-hydroxytryptamine receptor 2C

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

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]

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	12	N/A	N/A	A27755

Details6. Muscarinic acetylcholine receptor M1

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

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]

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	7	N/A	N/A	A27755

Details7. Muscarinic acetylcholine receptor M2

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

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]

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	12	N/A	N/A	A27755

Details8. Muscarinic acetylcholine receptor M3

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

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]

Details9. 5-hydroxytryptamine receptor 7

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

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

Details1. UDP-glucuronosyltransferase 1-3

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

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]

Details2. UDP-glucuronosyltransferase 1-4

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

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]

Details3. UDP-glucuronosyltransferase 2B10

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

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

Details1. Serum albumin

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

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

Details1. Solute carrier family 22 member 1

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

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 October 18, 2021 04:55

Cyproheptadine

Identification

Structure for Cyproheptadine (DB00434)

Pharmacology

Interactions

Products

Categories

Chemical Identifiers

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra

Targets

References

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References

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References

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Enzymes

References

References

References

Carriers

References

Transporters

References