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

Molecular Formula C21H21N
Molecular Weight 287.3981
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/7650688 | http://www.empr.com/cyproheptadine/drug/23/ | http://reference.medscape.com/drug/cyproheptadine-343389

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.

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

3.16224012E11
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

3.16224012E11
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

3.16224012E11
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

3.16224012E11
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

3.16224012E11
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

3.16224012E11
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

3.16224012E11
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

-2.59113599E11
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

-2.59113599E11
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

-2.59113599E11
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
A short history of the 5-HT(2C) receptor: from the choroid plexus to depression, obesity and addiction treatment.
2017 May
Reconsideration of the diagnosis and treatment of childhood migraine: A practical review of clinical experiences.
2017 May
Patents

Sample Use Guides

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
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.
Substance Class Chemical
Created
by admin
on Thu Jul 06 22:14:09 UTC 2023
Edited
by admin
on Thu Jul 06 22:14:09 UTC 2023
Record UNII
2YHB6175DO
Record Status Validated (UNII)
Record Version
  • Download
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 Thu Jul 06 22:14:12 UTC 2023 , Edited by admin on Thu Jul 06 22:14:12 UTC 2023
LIVERTOX NBK548422
Created by admin on Thu Jul 06 22:14:12 UTC 2023 , Edited by admin on Thu Jul 06 22:14:12 UTC 2023
NCI_THESAURUS C29578
Created by admin on Thu Jul 06 22:14:12 UTC 2023 , Edited by admin on Thu Jul 06 22:14:12 UTC 2023
WHO-VATC QR06AX02
Created by admin on Thu Jul 06 22:14:12 UTC 2023 , Edited by admin on Thu Jul 06 22:14:12 UTC 2023
Code System Code Type Description
RXCUI
3013
Created by admin on Thu Jul 06 22:14:12 UTC 2023 , Edited by admin on Thu Jul 06 22:14:12 UTC 2023
PRIMARY RxNorm
SMS_ID
100000083988
Created by admin on Thu Jul 06 22:14:12 UTC 2023 , Edited by admin on Thu Jul 06 22:14:12 UTC 2023
PRIMARY
FDA UNII
2YHB6175DO
Created by admin on Thu Jul 06 22:14:12 UTC 2023 , Edited by admin on Thu Jul 06 22:14:12 UTC 2023
PRIMARY
CHEBI
4046
Created by admin on Thu Jul 06 22:14:12 UTC 2023 , Edited by admin on Thu Jul 06 22:14:12 UTC 2023
PRIMARY
DRUG CENTRAL
765
Created by admin on Thu Jul 06 22:14:12 UTC 2023 , Edited by admin on Thu Jul 06 22:14:12 UTC 2023
PRIMARY
WIKIPEDIA
CYPROHEPTADINE
Created by admin on Thu Jul 06 22:14:12 UTC 2023 , Edited by admin on Thu Jul 06 22:14:12 UTC 2023
PRIMARY
INN
872
Created by admin on Thu Jul 06 22:14:12 UTC 2023 , Edited by admin on Thu Jul 06 22:14:12 UTC 2023
PRIMARY
EVMPD
SUB06875MIG
Created by admin on Thu Jul 06 22:14:12 UTC 2023 , Edited by admin on Thu Jul 06 22:14:12 UTC 2023
PRIMARY
LACTMED
Cyproheptadine
Created by admin on Thu Jul 06 22:14:12 UTC 2023 , Edited by admin on Thu Jul 06 22:14:12 UTC 2023
PRIMARY
CAS
129-03-3
Created by admin on Thu Jul 06 22:14:12 UTC 2023 , Edited by admin on Thu Jul 06 22:14:12 UTC 2023
PRIMARY
DRUG BANK
DB00434
Created by admin on Thu Jul 06 22:14:12 UTC 2023 , Edited by admin on Thu Jul 06 22:14:12 UTC 2023
PRIMARY
IUPHAR
277
Created by admin on Thu Jul 06 22:14:12 UTC 2023 , Edited by admin on Thu Jul 06 22:14:12 UTC 2023
PRIMARY
MERCK INDEX
M4040
Created by admin on Thu Jul 06 22:14:12 UTC 2023 , Edited by admin on Thu Jul 06 22:14:12 UTC 2023
PRIMARY Merck Index
EPA CompTox
DTXSID8022872
Created by admin on Thu Jul 06 22:14:12 UTC 2023 , Edited by admin on Thu Jul 06 22:14:12 UTC 2023
PRIMARY
DAILYMED
2YHB6175DO
Created by admin on Thu Jul 06 22:14:12 UTC 2023 , Edited by admin on Thu Jul 06 22:14:12 UTC 2023
PRIMARY
PUBCHEM
2913
Created by admin on Thu Jul 06 22:14:12 UTC 2023 , Edited by admin on Thu Jul 06 22:14:12 UTC 2023
PRIMARY
ChEMBL
CHEMBL516
Created by admin on Thu Jul 06 22:14:12 UTC 2023 , Edited by admin on Thu Jul 06 22:14:12 UTC 2023
PRIMARY
NCI_THESAURUS
C61695
Created by admin on Thu Jul 06 22:14:12 UTC 2023 , Edited by admin on Thu Jul 06 22:14:12 UTC 2023
PRIMARY
HSDB
3048
Created by admin on Thu Jul 06 22:14:12 UTC 2023 , Edited by admin on Thu Jul 06 22:14:12 UTC 2023
PRIMARY
MESH
D003533
Created by admin on Thu Jul 06 22:14:12 UTC 2023 , Edited by admin on Thu Jul 06 22:14:12 UTC 2023
PRIMARY
ECHA (EC/EINECS)
204-928-9
Created by admin on Thu Jul 06 22:14:12 UTC 2023 , Edited by admin on Thu Jul 06 22:14:12 UTC 2023
PRIMARY
Related Record Type Details
METABOLITE -> PARENT
METABOLITE -> PARENT
METABOLITE -> PARENT
Related Record Type Details
IMPURITY -> PARENT
Related Record Type Details
ACTIVE MOIETY