U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of CYPROHEPTADINE

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

Description
Curator's Comment: description was created based on several sources, including: https://www.drugs.com/monograph/cyproheptadine-hydrochloride.html | http://www.mentalmeds.org/prescription_meds/Periactin.pdf

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.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
CYPROHEPTADINE HYDROCHLORIDE

Approved Use

Cyproheptadine hydrochloride is indicated 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; Amelioration of allergic reactions to blood or plasma; Cold urticaria; Dermatographism; As therapy for anaphylactic reactions adjunctive to epinephrine and other standard measures after the acute manifestations have been controlled.

Launch Date

1980
Primary
CYPROHEPTADINE HYDROCHLORIDE

Approved Use

Cyproheptadine hydrochloride is indicated 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; Amelioration of allergic reactions to blood or plasma; Cold urticaria; Dermatographism; As therapy for anaphylactic reactions adjunctive to epinephrine and other standard measures after the acute manifestations have been controlled.

Launch Date

1980
Primary
CYPROHEPTADINE HYDROCHLORIDE

Approved Use

Cyproheptadine hydrochloride is indicated 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; Amelioration of allergic reactions to blood or plasma; Cold urticaria; Dermatographism; As therapy for anaphylactic reactions adjunctive to epinephrine and other standard measures after the acute manifestations have been controlled.

Launch Date

1980
Primary
CYPROHEPTADINE HYDROCHLORIDE

Approved Use

Cyproheptadine hydrochloride is indicated 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; Amelioration of allergic reactions to blood or plasma; Cold urticaria; Dermatographism; As therapy for anaphylactic reactions adjunctive to epinephrine and other standard measures after the acute manifestations have been controlled.

Launch Date

1980
Primary
CYPROHEPTADINE HYDROCHLORIDE

Approved Use

Cyproheptadine hydrochloride is indicated 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; Amelioration of allergic reactions to blood or plasma; Cold urticaria; Dermatographism; As therapy for anaphylactic reactions adjunctive to epinephrine and other standard measures after the acute manifestations have been controlled.

Launch Date

1980
Primary
CYPROHEPTADINE HYDROCHLORIDE

Approved Use

Cyproheptadine hydrochloride is indicated 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; Amelioration of allergic reactions to blood or plasma; Cold urticaria; Dermatographism; As therapy for anaphylactic reactions adjunctive to epinephrine and other standard measures after the acute manifestations have been controlled.

Launch Date

1980
Primary
CYPROHEPTADINE HYDROCHLORIDE

Approved Use

Cyproheptadine hydrochloride is indicated 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; Amelioration of allergic reactions to blood or plasma; Cold urticaria; Dermatographism; As therapy for anaphylactic reactions adjunctive to epinephrine and other standard measures after the acute manifestations have been controlled.

Launch Date

1980
Primary
PERIACTIN

Approved Use

Indications and Usage. Perennial and seasonal allergic rhinitis, Vasomotor rhinitis, Allergic conjunctivitis due to inhalant allergens and foods. Mild, uncomplicated allergic skin manifestations of urticaria and angioedema. Amelioration of allergic reactions to blood or plasma, Cold urticaria, Dermatographism. As therapy for anaphylactic reactions adjunctive to epinephrine and other standard measures after the acute manifestations have been controlled.

Launch Date

1961
Primary
PERIACTIN

Approved Use

Indications and Usage. Perennial and seasonal allergic rhinitis, Vasomotor rhinitis, Allergic conjunctivitis due to inhalant allergens and foods. Mild, uncomplicated allergic skin manifestations of urticaria and angioedema. Amelioration of allergic reactions to blood or plasma, Cold urticaria, Dermatographism. As therapy for anaphylactic reactions adjunctive to epinephrine and other standard measures after the acute manifestations have been controlled.

Launch Date

1961
Primary
PERIACTIN

Approved Use

Indications and Usage. Perennial and seasonal allergic rhinitis, Vasomotor rhinitis, Allergic conjunctivitis due to inhalant allergens and foods. Mild, uncomplicated allergic skin manifestations of urticaria and angioedema. Amelioration of allergic reactions to blood or plasma, Cold urticaria, Dermatographism. As therapy for anaphylactic reactions adjunctive to epinephrine and other standard measures after the acute manifestations have been controlled.

Launch Date

1961
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
1.25 ng/mL
4 mg single, oral
dose: 4 mg
route of administration: Oral
experiment type: SINGLE
co-administered: COBAMAMIDE
CYPROHEPTADINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
40.82 ng × h/mL
4 mg single, oral
dose: 4 mg
route of administration: Oral
experiment type: SINGLE
co-administered: COBAMAMIDE
CYPROHEPTADINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
38.21 h
4 mg single, oral
dose: 4 mg
route of administration: Oral
experiment type: SINGLE
co-administered: COBAMAMIDE
CYPROHEPTADINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
0.227 mg/kg 3 times / day multiple, digestive tract route (median)
Recommended
Dose: 0.227 mg/kg, 3 times / day
Route: digestive tract route
Route: multiple
Dose: 0.227 mg/kg, 3 times / day
Sources:
unhealthy, 17.6 month
n = 39
Health Status: unhealthy
Condition: feeding intolerance or vomiting
Age Group: 17.6 month
Sex: M+F
Population Size: 39
Sources:
Other AEs: Sleepiness, Constipation...
Other AEs:
Sleepiness (4 patients)
Constipation (3 patients)
Abnormal behaviour NOS (2 patients)
Sources:
22.5 mg single, oral
Dose: 22.5 mg
Route: oral
Route: single
Dose: 22.5 mg
Sources:
healthy, 4
n = 1
Health Status: healthy
Age Group: 4
Population Size: 1
Sources:
Other AEs: Disorientation, Abnormal behaviour...
Other AEs:
Disorientation
Abnormal behaviour
Sources:
6 mg multiple, digestive tract route (median)
Recommended
Dose: 6 mg
Route: digestive tract route
Route: multiple
Dose: 6 mg
Sources:
unhealthy, 9.8
n = 80
Health Status: unhealthy
Condition: refractory upper gastrointestinal symptoms
Age Group: 9.8
Sex: M+F
Population Size: 80
Sources:
Other AEs: Somnolence, Irritability...
Other AEs:
Somnolence (16%)
Irritability (6%)
Increased appetite (5%)
Abdominal pain (2.5%)
Sources:
32 mg multiple, oral
Recommended
Dose: 32 mg
Route: oral
Route: multiple
Dose: 32 mg
Sources:
unhealthy, <40
n = 20
Health Status: unhealthy
Condition: endocrine disorders
Age Group: <40
Population Size: 20
Sources:
Other AEs: Weight gain, Drowsiness...
Other AEs:
Weight gain (19 patients)
Drowsiness
Sources:
AEs

AEs

AESignificanceDosePopulation
Abnormal behaviour NOS 2 patients
0.227 mg/kg 3 times / day multiple, digestive tract route (median)
Recommended
Dose: 0.227 mg/kg, 3 times / day
Route: digestive tract route
Route: multiple
Dose: 0.227 mg/kg, 3 times / day
Sources:
unhealthy, 17.6 month
n = 39
Health Status: unhealthy
Condition: feeding intolerance or vomiting
Age Group: 17.6 month
Sex: M+F
Population Size: 39
Sources:
Constipation 3 patients
0.227 mg/kg 3 times / day multiple, digestive tract route (median)
Recommended
Dose: 0.227 mg/kg, 3 times / day
Route: digestive tract route
Route: multiple
Dose: 0.227 mg/kg, 3 times / day
Sources:
unhealthy, 17.6 month
n = 39
Health Status: unhealthy
Condition: feeding intolerance or vomiting
Age Group: 17.6 month
Sex: M+F
Population Size: 39
Sources:
Sleepiness 4 patients
0.227 mg/kg 3 times / day multiple, digestive tract route (median)
Recommended
Dose: 0.227 mg/kg, 3 times / day
Route: digestive tract route
Route: multiple
Dose: 0.227 mg/kg, 3 times / day
Sources:
unhealthy, 17.6 month
n = 39
Health Status: unhealthy
Condition: feeding intolerance or vomiting
Age Group: 17.6 month
Sex: M+F
Population Size: 39
Sources:
Abnormal behaviour
22.5 mg single, oral
Dose: 22.5 mg
Route: oral
Route: single
Dose: 22.5 mg
Sources:
healthy, 4
n = 1
Health Status: healthy
Age Group: 4
Population Size: 1
Sources:
Disorientation
22.5 mg single, oral
Dose: 22.5 mg
Route: oral
Route: single
Dose: 22.5 mg
Sources:
healthy, 4
n = 1
Health Status: healthy
Age Group: 4
Population Size: 1
Sources:
Somnolence 16%
6 mg multiple, digestive tract route (median)
Recommended
Dose: 6 mg
Route: digestive tract route
Route: multiple
Dose: 6 mg
Sources:
unhealthy, 9.8
n = 80
Health Status: unhealthy
Condition: refractory upper gastrointestinal symptoms
Age Group: 9.8
Sex: M+F
Population Size: 80
Sources:
Abdominal pain 2.5%
6 mg multiple, digestive tract route (median)
Recommended
Dose: 6 mg
Route: digestive tract route
Route: multiple
Dose: 6 mg
Sources:
unhealthy, 9.8
n = 80
Health Status: unhealthy
Condition: refractory upper gastrointestinal symptoms
Age Group: 9.8
Sex: M+F
Population Size: 80
Sources:
Increased appetite 5%
6 mg multiple, digestive tract route (median)
Recommended
Dose: 6 mg
Route: digestive tract route
Route: multiple
Dose: 6 mg
Sources:
unhealthy, 9.8
n = 80
Health Status: unhealthy
Condition: refractory upper gastrointestinal symptoms
Age Group: 9.8
Sex: M+F
Population Size: 80
Sources:
Irritability 6%
6 mg multiple, digestive tract route (median)
Recommended
Dose: 6 mg
Route: digestive tract route
Route: multiple
Dose: 6 mg
Sources:
unhealthy, 9.8
n = 80
Health Status: unhealthy
Condition: refractory upper gastrointestinal symptoms
Age Group: 9.8
Sex: M+F
Population Size: 80
Sources:
Drowsiness
32 mg multiple, oral
Recommended
Dose: 32 mg
Route: oral
Route: multiple
Dose: 32 mg
Sources:
unhealthy, <40
n = 20
Health Status: unhealthy
Condition: endocrine disorders
Age Group: <40
Population Size: 20
Sources:
Weight gain 19 patients
32 mg multiple, oral
Recommended
Dose: 32 mg
Route: oral
Route: multiple
Dose: 32 mg
Sources:
unhealthy, <40
n = 20
Health Status: unhealthy
Condition: endocrine disorders
Age Group: <40
Population Size: 20
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer






Drug as perpetrator​Drug as victimTox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Cyproheptadine use in hepatocellular carcinoma.
2017
Polypharmacological in Silico Bioactivity Profiling and Experimental Validation Uncovers Sedative-Hypnotic Effects of Approved and Experimental Drugs in Rat.
2017 Jun 16
Survey on treatments for primary headaches in 13 specialized juvenile Headache Centers: The first multicenter Italian study.
2017 May
Reconsideration of the diagnosis and treatment of childhood migraine: A practical review of clinical experiences.
2017 May
Patents

Sample Use Guides

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
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
Name Type Language
CYPROHEPTADINE
HSDB   INN   MI   VANDF   WHO-DD  
INN  
Official Name English
CYPROHEPTADINE [MI]
Common Name English
CIPROVIT
Brand Name English
CYPROHEPTADINE [VANDF]
Common Name English
CYPROHEPTADINE [HSDB]
Common Name English
Cyproheptadine [WHO-DD]
Common Name English
PIPERIDINE, 4-(5H-DIBENZO(A,D)CYCLOHEPTEN-5-YLIDENE)-1-METHYL-
Systematic Name English
cyproheptadine [INN]
Common Name English
4-(5H-DIBENZO(A,D)CYCLOHEPTEN-5-YLIDENE)-1-METHYLPIPERIDINE
Systematic Name English
Classification Tree Code System Code
WHO-ATC R06AX02
Created by admin on Sat Dec 16 16:47:07 GMT 2023 , Edited by admin on Sat Dec 16 16:47:07 GMT 2023
LIVERTOX NBK548422
Created by admin on Sat Dec 16 16:47:07 GMT 2023 , Edited by admin on Sat Dec 16 16:47:07 GMT 2023
NCI_THESAURUS C29578
Created by admin on Sat Dec 16 16:47:07 GMT 2023 , Edited by admin on Sat Dec 16 16:47:07 GMT 2023
WHO-VATC QR06AX02
Created by admin on Sat Dec 16 16:47:07 GMT 2023 , Edited by admin on Sat Dec 16 16:47:07 GMT 2023
Code System Code Type Description
RXCUI
3013
Created by admin on Sat Dec 16 16:47:07 GMT 2023 , Edited by admin on Sat Dec 16 16:47:07 GMT 2023
PRIMARY RxNorm
SMS_ID
100000083988
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PRIMARY
FDA UNII
2YHB6175DO
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PRIMARY
CHEBI
4046
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PRIMARY
DRUG CENTRAL
765
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PRIMARY
WIKIPEDIA
CYPROHEPTADINE
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PRIMARY
INN
872
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PRIMARY
EVMPD
SUB06875MIG
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PRIMARY
LACTMED
Cyproheptadine
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PRIMARY
CAS
129-03-3
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PRIMARY
DRUG BANK
DB00434
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PRIMARY
IUPHAR
277
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PRIMARY
MERCK INDEX
m4040
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PRIMARY Merck Index
EPA CompTox
DTXSID8022872
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PRIMARY
DAILYMED
2YHB6175DO
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PRIMARY
PUBCHEM
2913
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PRIMARY
ChEMBL
CHEMBL516
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PRIMARY
NCI_THESAURUS
C61695
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PRIMARY
HSDB
3048
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PRIMARY
MESH
D003533
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PRIMARY
ECHA (EC/EINECS)
204-928-9
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PRIMARY