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=CC=CC=C3C=CC4=CC=CC=C24

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

Description

Glutodine (Cyproheptadine), sold under the brand name Periactin or Peritol, is a first-generation antihistamine with additional antiserotonergic, anticholinergic and local anesthetic properties. Glutodine is a white to slightly yellowish crystalline solid, which is soluble in water, freely soluble in methanol, sparingly soluble in ethanol, soluble in chloroform, and practically insoluble in ether. Cyproheptadine is used to treat allergic reactions (specifically hay fever), Vasomotor rhinitis, Allergic conjunctivitis due to inhalant allergens and foods, uncomplicated allergic skin manifestations of urticaria and angioedema amelioration of allergic reactions to blood or plasma, Cold urticaria, and Dermatographism. Cyproheptadine is used off-label to treat Spasticity Associated With Spinal Cord, Migraine Headache Prophylaxis, Decreased Appetite Secondary to Chronic Disease, Drug-Induced Sexual Dysfunction, Serotonin Syndrome.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Histamine H1 receptor 316	Antagonist 2,849	2.7 nM [Ki]
Serotonin 2 (5-HT2) receptor 90	Antagonist 2,849	6.5 nM [Ki]
Serotonin 2a (5-HT2a) receptor 237	Antagonist 2,849	8.8 null [pKi]
Muscarinic acetylcholine receptor 162	Antagonist 2,849	19.0 nM [Ki]
Histamine H1 receptor 316	Antagonist 2,849	0.537 nM [Ki]
Serotonin 2a (5-HT2a) receptor 237	Antagonist 2,849	1.6 nM [Ki]
Serotonin 2c (5-HT2c) receptor 131	Antagonist 2,849	11.0 nM [Ki]

Conditions

Condition	Modality	Highest Phase	Product
Vasomotor rhinitis 21	Primary	Approved 8,583	CYPROHEPTADINE HYDROCHLORIDE
Perennial allergic rhinitis 47	Primary	Approved 8,583	CYPROHEPTADINE HYDROCHLORIDE
Seasonal allergic rhinitis 64	Primary	Approved 8,583	CYPROHEPTADINE HYDROCHLORIDE
Allergic conjunctivitis 101	Primary	Approved 8,583	CYPROHEPTADINE HYDROCHLORIDE
Urticaria 39	Primary	Approved 8,583	CYPROHEPTADINE HYDROCHLORIDE
Angioedema 20	Primary	Approved 8,583	CYPROHEPTADINE HYDROCHLORIDE
Anaphylaxis 47	Primary	Approved 8,583	CYPROHEPTADINE HYDROCHLORIDE
Cold urticaria 10	Primary	Approved 8,583	PERIACTIN
Vasomotor rhinitis 21	Primary	Approved 8,583	PERIACTIN
Uncomplicated allergic skin manifestations of angioedema 10	Primary	Approved 8,583	PERIACTIN

C_max

Value	Dose	Co-administered	Analyte	Population
30 μg/L	8 mg single, oral		GLUTODINE plasma	Homo sapiens
4 μg/L	8 mg single, sublingual		GLUTODINE plasma	Homo sapiens
1.25 ng/mL	4 mg single, oral	COBAMAMIDE	GLUTODINE plasma	Homo sapiens
1.25 ng/mL	4 mg single, oral	COBAMAMIDE	CYPROHEPTADINE plasma	Homo sapiens

AUC

Value	Dose	Co-administered	Analyte	Population
209 μg × h/L	8 mg single, oral		GLUTODINE plasma	Homo sapiens
25 μg × h/L	8 mg single, sublingual		GLUTODINE plasma	Homo sapiens
40.82 ng × h/mL	4 mg single, oral	COBAMAMIDE	GLUTODINE plasma	Homo sapiens
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	GLUTODINE plasma	Homo sapiens
38.21 h	4 mg single, oral	COBAMAMIDE	CYPROHEPTADINE plasma	Homo sapiens

Doses

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

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AEs

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

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG
			inhibitor 2,217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OCT1 620 K+ channels 73 L-type Ca2+ channels 28	UGT1A3 470 UGT1A4 399 CYP1A2 1,197

Drug as perpetrator

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Target	Modality	Activity
K+ channels 73	inhibitor 4,027	yes
L-type Ca2+ channels 30	inhibitor 4,027	yes
OCT1 656	inhibitor 4,027	yes

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Drug as victim

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Target	Modality	Activity
CYP1A2 1,197	substrate 4,014	likely
UGT1A3 470	substrate 4,014	yes
UGT1A4 399	substrate 4,014	yes

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Tox targets

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Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2,263	inhibitor 2,237

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Sourcing

Sourcing

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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
Aaron Chemicals	AR005T5T	http://www.aaronchem.com/969-33-5
abcr GmbH	AB497226	http://www.abcr.de/shop/en/AB497226
Achemtek	0104-016666	http://www.achemtek.com/41354-29-4

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PubMed

Title	Date	PubMed
No data available in table

Patents

Sample Use Guides

In Vivo Use Guide

The total daily dose for adults should not exceed 0.5 mg/kg/day. The therapeutic range is 4 to 20 mg a day, with the majority of patients requiring 12 to 16 mg a day. An occasional patient may require as much as 32 mg a day for adequate relief. It is suggested that dosage be initiated with 4 mg (1 tablet) three times a day and adjusted according to the size and response of the patient.

Route of Administration: Oral

In Vitro Use Guide

The IC50 of cyproheptadine, determined as the concentration of the drug that inhibited cell growth by 50% after 24 h of treatment, was found to be 44.4, 44.7, and 118.1 uM in HepG2 cells, Huh-7 cells, and normal human hepatocytes, respectively.

Show entries

Name

Type

Language

CIPROVIT

Preferred Name

English

CYPROHEPTADINE

Official Name

English

CYPROHEPTADINE [MI]

Common Name

English

CYPROHEPTADINE [VANDF]

Common Name

English

CYPROHEPTADINE [HSDB]

Common Name

English

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Classification Tree

Code System

Code

Other antihistamines for systemic use

WHO-ATC

R06AX02

Allergy symptoms

LIVERTOX

NBK548422

Immunotherapeutic Agent

NCI_THESAURUS

C29578

Other antihistamines for systemic use

WHO-VATC

QR06AX02

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Code System

Code

Type

Description

RXCUI

3013

PRIMARY

RxNorm

SMS_ID

100000083988

PRIMARY

FDA UNII

2YHB6175DO

PRIMARY

CHEBI

4046

PRIMARY

DRUG CENTRAL

765

PRIMARY

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ACTIVE MOIETY


					2YHB6175DO

CYPROHEPTADINE

METABOLITE (PARENT)


					6DR55R4RJP

NORCYPROHEPTADINE

METABOLITE (PARENT)


					AW3G2X5UQD

CYPROHEPTADINE-10,11-EPOXIDE

METABOLITE (PARENT)


					V7JNC2PZ2C

DESMETHYLCYPROHEPTADINE 10,11-EPOXIDE

SMILES

InChI

CNS Activity

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Doses

AEs

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Tox targets

Sourcing

PubMed

Patents

Sample Use Guides

C_max

T_1/2

Drug as perpetrator