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

Details

Stereochemistry ACHIRAL
Molecular Formula 2C21H21N.2ClH.3H2O
Molecular Weight 701.764
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CYPROHEPTADINE HYDROCHLORIDE

SMILES

O.O.O.Cl.Cl.CN1CCC(CC1)=C2C3=C(C=CC=C3)C=CC4=C2C=CC=C4.CN5CCC(CC5)=C6C7=C(C=CC=C7)C=CC8=C6C=CC=C8

InChI

InChIKey=ZEAUHIZSRUAMQG-UHFFFAOYSA-N
InChI=1S/2C21H21N.2ClH.3H2O/c2*1-22-14-12-18(13-15-22)21-19-8-4-2-6-16(19)10-11-17-7-3-5-9-20(17)21;;;;;/h2*2-11H,12-15H2,1H3;2*1H;3*1H2

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
Cyproheptadine: A Potentially Effective Treatment for Functional Gastrointestinal Disorders in Children.
2017 Mar 1
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
A short history of the 5-HT(2C) receptor: from the choroid plexus to depression, obesity and addiction treatment.
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 HYDROCHLORIDE
EP   MART.   ORANGE BOOK   USP   USP-RS   VANDF  
Common Name English
CYPROHEPTADINE HYDROCHLORIDE [VANDF]
Common Name English
CYPROHEPTADINE HYDROCHLORIDE [USP-RS]
Common Name English
CYPROHEPTADINE HYDROCHLORIDE [MART.]
Common Name English
CYPROHEPTADINE HYDROCHLORIDE SESQUIHYDRATE [MI]
Common Name English
PIPERIDINE, 4-(5H-DIBENZO(A,D)CYCLOHEPTEN-5-YLIDENE)-1-METHYL-, HYDROCHLORIDE, SESQUIHYDRATE
Common Name English
CYPROHEPTADINE HYDROCHLORIDE SESQUIHYDRATE
MI  
Common Name English
CYPROHEPTADINE HYDROCHLORIDE HYDRATE [JAN]
Common Name English
PERIACTINE
Brand Name English
CYPROHEPTADINE HYDROCHLORIDE HYDRATE
Common Name English
CYPROHEPTADINE HCL
Common Name English
CYPROHEPTADINE HYDROCHLORIDE [ORANGE BOOK]
Common Name English
PERITOL
Brand Name English
PERIACTIN
Brand Name English
NSC-759282
Code English
CYPROHEPTADINE HYDROCHLORIDE [USP MONOGRAPH]
Common Name English
4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-methylpiperidine hydrochloride sesquihydrate
Common Name English
PIPERIDINE, 4-(5H-DIBENZO(A,D)CYCLOHEPTEN-5-YLIDENE)-1-METHYL-, HYDROCHLORIDE, HYDRATE (2:2:3)
Common Name English
CYPROHEPTADINE HYDROCHLORIDE [EP IMPURITY]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29578
Created by admin on Fri Dec 15 15:14:18 GMT 2023 , Edited by admin on Fri Dec 15 15:14:18 GMT 2023
Code System Code Type Description
DAILYMED
NJ82J0F8QC
Created by admin on Fri Dec 15 15:14:18 GMT 2023 , Edited by admin on Fri Dec 15 15:14:18 GMT 2023
PRIMARY
CHEBI
59695
Created by admin on Fri Dec 15 15:14:18 GMT 2023 , Edited by admin on Fri Dec 15 15:14:18 GMT 2023
PRIMARY
MERCK INDEX
m4040
Created by admin on Fri Dec 15 15:14:18 GMT 2023 , Edited by admin on Fri Dec 15 15:14:18 GMT 2023
PRIMARY Merck Index
ChEMBL
CHEMBL516
Created by admin on Fri Dec 15 15:14:18 GMT 2023 , Edited by admin on Fri Dec 15 15:14:18 GMT 2023
PRIMARY
EVMPD
SUB01537MIG
Created by admin on Fri Dec 15 15:14:18 GMT 2023 , Edited by admin on Fri Dec 15 15:14:18 GMT 2023
PRIMARY
CHEBI
650917
Created by admin on Fri Dec 15 15:14:18 GMT 2023 , Edited by admin on Fri Dec 15 15:14:18 GMT 2023
PRIMARY
PUBCHEM
11954233
Created by admin on Fri Dec 15 15:14:18 GMT 2023 , Edited by admin on Fri Dec 15 15:14:18 GMT 2023
PRIMARY
SMS_ID
100000084677
Created by admin on Fri Dec 15 15:14:18 GMT 2023 , Edited by admin on Fri Dec 15 15:14:18 GMT 2023
PRIMARY
DRUG BANK
DBSALT000625
Created by admin on Fri Dec 15 15:14:18 GMT 2023 , Edited by admin on Fri Dec 15 15:14:18 GMT 2023
PRIMARY
FDA UNII
NJ82J0F8QC
Created by admin on Fri Dec 15 15:14:18 GMT 2023 , Edited by admin on Fri Dec 15 15:14:18 GMT 2023
PRIMARY
RXCUI
104592
Created by admin on Fri Dec 15 15:14:18 GMT 2023 , Edited by admin on Fri Dec 15 15:14:18 GMT 2023
PRIMARY RxNorm
NSC
759282
Created by admin on Fri Dec 15 15:14:18 GMT 2023 , Edited by admin on Fri Dec 15 15:14:18 GMT 2023
PRIMARY
CAS
41354-29-4
Created by admin on Fri Dec 15 15:14:18 GMT 2023 , Edited by admin on Fri Dec 15 15:14:18 GMT 2023
PRIMARY
NCI_THESAURUS
C28949
Created by admin on Fri Dec 15 15:14:18 GMT 2023 , Edited by admin on Fri Dec 15 15:14:18 GMT 2023
PRIMARY
RS_ITEM_NUM
1161000
Created by admin on Fri Dec 15 15:14:18 GMT 2023 , Edited by admin on Fri Dec 15 15:14:18 GMT 2023
PRIMARY
EPA CompTox
DTXSID70274175
Created by admin on Fri Dec 15 15:14:18 GMT 2023 , Edited by admin on Fri Dec 15 15:14:18 GMT 2023
PRIMARY