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Details

Stereochemistry ACHIRAL
Molecular Formula C21H21N.C6H13NO3S
Molecular Weight 466.635
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CYPROHEPTADINE CYCLAMATE

SMILES

OS(=O)(=O)NC1CCCCC1.CN2CCC(CC2)=C3C4=C(C=CC=C4)C=CC5=C3C=CC=C5

InChI

InChIKey=HJISOJBHWJLIJB-UHFFFAOYSA-N
InChI=1S/C21H21N.C6H13NO3S/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;8-11(9,10)7-6-4-2-1-3-5-6/h2-11H,12-15H2,1H3;6-7H,1-5H2,(H,8,9,10)

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

Molecular Formula C6H13NO3S
Molecular Weight 179.237
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
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 13:35:10 UTC 2023
Edited
by admin
on Thu Jul 06 13:35:10 UTC 2023
Record UNII
XK14HG3ANJ
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CYPROHEPTADINE CYCLAMATE
WHO-DD  
Common Name English
Cyproheptadine cyclamate [WHO-DD]
Common Name English
PIPERIDINE, 4-(5H-DIBENZO(A,D)CYCLOHEPTEN-5-YLIDENE)-1-METHYL-, CYCLOHEXANESULFAMATE
Systematic Name English
SULFAMIC ACID, N-CYCLOHEXYL-, COMPD. WITH 4-(5H-DIBENZO(A,D)CYCLOHEPTEN-5-YLIDENE)-1-METHYLPIPERIDINE (1:1)
Systematic Name English
Code System Code Type Description
FDA UNII
XK14HG3ANJ
Created by admin on Thu Jul 06 13:35:10 UTC 2023 , Edited by admin on Thu Jul 06 13:35:10 UTC 2023
PRIMARY
CAS
24440-32-2
Created by admin on Thu Jul 06 13:35:10 UTC 2023 , Edited by admin on Thu Jul 06 13:35:10 UTC 2023
PRIMARY
PUBCHEM
71587063
Created by admin on Thu Jul 06 13:35:10 UTC 2023 , Edited by admin on Thu Jul 06 13:35:10 UTC 2023
PRIMARY
EVMPD
SUB01536MIG
Created by admin on Thu Jul 06 13:35:10 UTC 2023 , Edited by admin on Thu Jul 06 13:35:10 UTC 2023
PRIMARY
SMS_ID
100000084676
Created by admin on Thu Jul 06 13:35:10 UTC 2023 , Edited by admin on Thu Jul 06 13:35:10 UTC 2023
PRIMARY
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