CYPROHEPTADINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C21H21N
Molecular Weight	287.3981
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

CN1CCC(CC1)=C2C3=C(C=CC=C3)C=CC4=C2C=CC=C4

InChI

InChIKey=JJCFRYNCJDLXIK-UHFFFAOYSA-N

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

HIDE SMILES / InChI

Molecular Formula	C21H21N
Molecular Weight	287.3981
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description

Cyproheptadine hydrochloride anhydrous is a first-generation antihistamine with additional anticholinergic, antiserotonergic, and local anesthetic properties. It is indicted for the treatment of perennial and seasonal allergic rhinitis; vasomotor rhinitis; allergic conjunctivitis due to inhalant allergens and foods; mild, uncomplicated allergic skin manifestations of urticaria and angioedema. As therapy for anaphylactic reactions adjunctive to epinephrine and other standard measures after the acute manifestations have been controlled. MAO inhibitors prolong and intensify the anticholinergic effects of antihistamines. Antihistamines may have additive effects with alcohol and other CNS depressants, e.g., hypnotics, sedatives, tranquilizers, antianxiety agents. Common adverse effects are: sedation, sleepiness (often transient), dizziness, disturbed coordination, restlessness, excitation.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Histamine H1 receptor 315	Antagonist 2,778	2.7 nM [Ki]
Serotonin 2 (5-HT2) receptor 87	Antagonist 2,778	6.5 nM [Ki]
Serotonin 2a (5-HT2a) receptor 231	Antagonist 2,778	8.8 null [pKi]
Muscarinic acetylcholine receptor 160	Antagonist 2,778	19.0 nM [Ki]
Histamine H1 receptor 315	Antagonist 2,778	0.537 nM [Ki]
Serotonin 2a (5-HT2a) receptor 231	Antagonist 2,778	1.6 nM [Ki]
Serotonin 2c (5-HT2c) receptor 124	Antagonist 2,778	11.0 nM [Ki]

Conditions

Condition	Modality	Highest Phase	Product
Vasomotor rhinitis 21	Primary	Approved 8,429	CYPROHEPTADINE HYDROCHLORIDE
Perennial allergic rhinitis 47	Primary	Approved 8,429	CYPROHEPTADINE HYDROCHLORIDE
Seasonal allergic rhinitis 64	Primary	Approved 8,429	CYPROHEPTADINE HYDROCHLORIDE
Allergic conjunctivitis 100	Primary	Approved 8,429	CYPROHEPTADINE HYDROCHLORIDE
Urticaria 39	Primary	Approved 8,429	CYPROHEPTADINE HYDROCHLORIDE
Angioedema 20	Primary	Approved 8,429	CYPROHEPTADINE HYDROCHLORIDE
Anaphylaxis 46	Primary	Approved 8,429	CYPROHEPTADINE HYDROCHLORIDE
Cold urticaria 10	Primary	Approved 8,429	PERIACTIN
Vasomotor rhinitis 21	Primary	Approved 8,429	PERIACTIN
Uncomplicated allergic skin manifestations of angioedema 10	Primary	Approved 8,429	PERIACTIN

C_max

Value	Dose	Co-administered	Analyte	Population
1.25 ng/mL	4 mg single, oral	COBAMAMIDE	CYPROHEPTADINE plasma	Homo sapiens

AUC

Value	Dose	Co-administered	Analyte	Population
40.82 ng × h/mL	4 mg single, oral	COBAMAMIDE	CYPROHEPTADINE plasma	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
38.21 h	4 mg single, oral	COBAMAMIDE	CYPROHEPTADINE plasma	Homo sapiens

Doses

Show entries

Dose	Population	Adverse events
0.227 mg/kg 3 times / day multiple, digestive tract route (median) Recommended	unhealthy, 17.6 month n = 39	Other AEs: Sleepiness, Constipation...
22.5 mg single, oral	healthy, 4 n = 1	Other AEs: Disorientation, Abnormal behaviour...
6 mg multiple, digestive tract route (median) Recommended	unhealthy, 9.8 n = 80	Other AEs: Somnolence, Irritability...
32 mg multiple, oral Recommended	unhealthy, <40 n = 20	Other AEs: Weight gain, Drowsiness...

Showing 1 to 4 of 4 entries

Previous1Next

AEs

Show entries

AE	Significance	Dose	Population
Abnormal behaviour NOS	2 patients	0.227 mg/kg 3 times / day multiple, digestive tract route (median) Recommended	unhealthy, 17.6 month n = 39
Constipation	3 patients	0.227 mg/kg 3 times / day multiple, digestive tract route (median) Recommended	unhealthy, 17.6 month n = 39
Sleepiness	4 patients	0.227 mg/kg 3 times / day multiple, digestive tract route (median) Recommended	unhealthy, 17.6 month n = 39
Abnormal behaviour		22.5 mg single, oral	healthy, 4 n = 1
Disorientation		22.5 mg single, oral	healthy, 4 n = 1

Showing 1 to 5 of 11 entries

Previous1 2 3Next

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
			inhibitor 1,612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OCT1 512 K+ channels 70 L-type Ca2+ channels 28	UGT1A3 422 UGT1A4 347 CYP1A2 1,054

Drug as perpetrator

Show entries

Target	Modality	Activity
K+ channels 70	inhibitor 3,277	yes
L-type Ca2+ channels 30	inhibitor 3,277	yes
OCT1 543	inhibitor 3,277	yes

Showing 1 to 3 of 3 entries

Previous1Next

Drug as victim

Show entries

Target	Modality	Activity
CYP1A2 1,054	substrate 3,367	likely
UGT1A3 422	substrate 3,367	yes
UGT1A4 347	substrate 3,367	yes

Showing 1 to 3 of 3 entries

Previous1Next

Tox targets

Show entries

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1,647	inhibitor 1,626

Showing 1 to 1 of 1 entries

Previous1Next

Sourcing

Sourcing

Show entries

Vendor/Aggregator	ID	URL
3B Scientific (Wuhan) Corp	3B1-00277	http://www.3bsc.com/index/pro_info.php?id=20489
AA Blocks	AA005SE1	https://www.aablocks.com/goods/Goods/detail?id=AA005SE1
AHH Chemical co.,ltd	API-1807	http://www.ahhchemical.com/product/API-1807.html
AK Scientific, Inc. (AKSCI)	J10393	http://www.aksci.com/item_detail.php?cat=J10393
AK Scientific, Inc. (AKSCI)	M230	http://www.aksci.com/item_detail.php?cat=M230

Showing 1 to 5 of 45 entries

Previous1 2 3 4 5…9Next

PubMed

Show entries

Title	Date	PubMed
Cyproheptadine: A Potentially Effective Treatment for Functional Gastrointestinal Disorders in Children.	2017 Mar 1	28287686
Survey on treatments for primary headaches in 13 specialized juvenile Headache Centers: The first multicenter Italian study.	2017 May	28082014

Showing 1 to 2 of 2 entries

Previous1Next

Patents

Sample Use Guides

In Vivo Use Guide

4 mg PO q8hr initially; maintenance: 4-20 mg/day, up to 32 mg/day divided q8hr in some patients; not to exceed 0.5 mg/kg/day

Route of Administration: Oral

In Vitro Use Guide

Cytotoxic effect of Cyproheptadine (Glutodine) on urothelial cancer cells was determined in SV-HUC1, TSGH 8301, BFTC 905, BFTC 909, J82, 5637 cell lined. Cells were treated with 25-- 150 mkM of Cyproheptadine for 24 h. Apoptosis analysis was performed using the Annexin V-FITC Apoptosis Detection Kit. Treatment with high dose Cyproheptadine (≥100 mkM) for 24 h induced significant cytotoxicity toward all bladder cancer cells, 50 mkM of Cyproheptadine only induced cytotoxicity in cancer cell lines but not in the immortalized normal urothelial SV-HUC1 cells