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
DescriptionSources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/087056s045lbl.pdfhttps://www.drugs.com/dosage/cyproheptadine.htmlCurator'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
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/087056s045lbl.pdfhttps://www.drugs.com/dosage/cyproheptadine.html
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.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL3943 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6261070 |
2.7 nM [Ki] | ||
Target ID: CHEMBL2093870 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6261070 |
6.5 nM [Ki] | ||
Target ID: CHEMBL322 |
8.8 null [pKi] | ||
Target ID: CHEMBL1907609 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6261070 |
19.0 nM [Ki] | ||
Target ID: CHEMBL3943 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7650688 |
0.537 nM [Ki] | ||
Target ID: CHEMBL322 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11229772 |
1.6 nM [Ki] | ||
Target ID: CHEMBL3006 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11266163 |
11.0 nM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | CYPROHEPTADINE HYDROCHLORIDE Approved UseCyproheptadine 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 Date1980 |
|||
Primary | CYPROHEPTADINE HYDROCHLORIDE Approved UseCyproheptadine 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 Date1980 |
|||
Primary | CYPROHEPTADINE HYDROCHLORIDE Approved UseCyproheptadine 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 Date1980 |
|||
Primary | CYPROHEPTADINE HYDROCHLORIDE Approved UseCyproheptadine 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 Date1980 |
|||
Primary | CYPROHEPTADINE HYDROCHLORIDE Approved UseCyproheptadine 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 Date1980 |
|||
Primary | CYPROHEPTADINE HYDROCHLORIDE Approved UseCyproheptadine 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 Date1980 |
|||
Primary | CYPROHEPTADINE HYDROCHLORIDE Approved UseCyproheptadine 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 Date1980 |
|||
Primary | PERIACTIN Approved UseIndications 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 Date1961 |
|||
Primary | PERIACTIN Approved UseIndications 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 Date1961 |
|||
Primary | PERIACTIN Approved UseIndications 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 Date1961 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
30 μg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15083941/ |
8 mg single, oral dose: 8 mg route of administration: Oral experiment type: SINGLE co-administered: |
GLUTODINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
4 μg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15083941/ |
8 mg single, sublingual dose: 8 mg route of administration: Sublingual experiment type: SINGLE co-administered: |
GLUTODINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
1.25 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/21432861/ |
4 mg single, oral dose: 4 mg route of administration: Oral experiment type: SINGLE co-administered: COBAMAMIDE |
GLUTODINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
1.25 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/21432861 |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
209 μg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15083941/ |
8 mg single, oral dose: 8 mg route of administration: Oral experiment type: SINGLE co-administered: |
GLUTODINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
25 μg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15083941/ |
8 mg single, sublingual dose: 8 mg route of administration: Sublingual experiment type: SINGLE co-administered: |
GLUTODINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
40.82 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/21432861/ |
4 mg single, oral dose: 4 mg route of administration: Oral experiment type: SINGLE co-administered: COBAMAMIDE |
GLUTODINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
40.82 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/21432861 |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
38.21 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/21432861/ |
4 mg single, oral dose: 4 mg route of administration: Oral experiment type: SINGLE co-administered: COBAMAMIDE |
GLUTODINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
38.21 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/21432861 |
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
Dose | Population | Adverse events |
---|---|---|
0.227 mg/kg 3 times / day multiple, digestive tract route 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 Health Status: unhealthy Age Group: 17.6 month Sex: M+F Sources: |
Other AEs: Sleepiness, Constipation... Other AEs: Sleepiness (4 patients) Sources: Constipation (3 patients) Abnormal behaviour NOS (2 patients) |
22.5 mg single, oral |
healthy, 4 |
Other AEs: Disorientation, Abnormal behaviour... |
6 mg multiple, digestive tract route Recommended Dose: 6 mg Route: digestive tract route Route: multiple Dose: 6 mg Sources: |
unhealthy, 9.8 |
Other AEs: Somnolence, Irritability... Other AEs: Somnolence (16%) Sources: Irritability (6%) Increased appetite (5%) Abdominal pain (2.5%) |
32 mg multiple, oral Recommended |
unhealthy, <40 |
Other AEs: Weight gain, Drowsiness... |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Abnormal behaviour NOS | 2 patients | 0.227 mg/kg 3 times / day multiple, digestive tract route 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 Health Status: unhealthy Age Group: 17.6 month Sex: M+F Sources: |
Constipation | 3 patients | 0.227 mg/kg 3 times / day multiple, digestive tract route 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 Health Status: unhealthy Age Group: 17.6 month Sex: M+F Sources: |
Sleepiness | 4 patients | 0.227 mg/kg 3 times / day multiple, digestive tract route 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 Health Status: unhealthy Age Group: 17.6 month Sex: M+F Sources: |
Abnormal behaviour | 22.5 mg single, oral |
healthy, 4 |
|
Disorientation | 22.5 mg single, oral |
healthy, 4 |
|
Somnolence | 16% | 6 mg multiple, digestive tract route Recommended Dose: 6 mg Route: digestive tract route Route: multiple Dose: 6 mg Sources: |
unhealthy, 9.8 |
Abdominal pain | 2.5% | 6 mg multiple, digestive tract route Recommended Dose: 6 mg Route: digestive tract route Route: multiple Dose: 6 mg Sources: |
unhealthy, 9.8 |
Increased appetite | 5% | 6 mg multiple, digestive tract route Recommended Dose: 6 mg Route: digestive tract route Route: multiple Dose: 6 mg Sources: |
unhealthy, 9.8 |
Irritability | 6% | 6 mg multiple, digestive tract route Recommended Dose: 6 mg Route: digestive tract route Route: multiple Dose: 6 mg Sources: |
unhealthy, 9.8 |
Drowsiness | 32 mg multiple, oral Recommended |
unhealthy, <40 |
|
Weight gain | 19 patients | 32 mg multiple, oral Recommended |
unhealthy, <40 |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 1.0 |
yes | |||
Page: 1.0 |
yes | |||
Page: 5.0 |
yes |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 543.0 |
likely | |||
Page: 543.0 |
yes | |||
Page: 543.0 |
yes |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 6.0 |
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25886177
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.
Name | Type | Language | ||
---|---|---|---|---|
|
Preferred Name | English | ||
|
Official Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English |
Classification Tree | Code System | Code | ||
---|---|---|---|---|
|
WHO-ATC |
R06AX02
Created by
admin on Wed Apr 02 08:24:07 GMT 2025 , Edited by admin on Wed Apr 02 08:24:07 GMT 2025
|
||
|
LIVERTOX |
NBK548422
Created by
admin on Wed Apr 02 08:24:07 GMT 2025 , Edited by admin on Wed Apr 02 08:24:07 GMT 2025
|
||
|
NCI_THESAURUS |
C29578
Created by
admin on Wed Apr 02 08:24:07 GMT 2025 , Edited by admin on Wed Apr 02 08:24:07 GMT 2025
|
||
|
WHO-VATC |
QR06AX02
Created by
admin on Wed Apr 02 08:24:07 GMT 2025 , Edited by admin on Wed Apr 02 08:24:07 GMT 2025
|
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
3013
Created by
admin on Wed Apr 02 08:24:07 GMT 2025 , Edited by admin on Wed Apr 02 08:24:07 GMT 2025
|
PRIMARY | RxNorm | ||
|
100000083988
Created by
admin on Wed Apr 02 08:24:07 GMT 2025 , Edited by admin on Wed Apr 02 08:24:07 GMT 2025
|
PRIMARY | |||
|
2YHB6175DO
Created by
admin on Wed Apr 02 08:24:07 GMT 2025 , Edited by admin on Wed Apr 02 08:24:07 GMT 2025
|
PRIMARY | |||
|
4046
Created by
admin on Wed Apr 02 08:24:07 GMT 2025 , Edited by admin on Wed Apr 02 08:24:07 GMT 2025
|
PRIMARY | |||
|
765
Created by
admin on Wed Apr 02 08:24:07 GMT 2025 , Edited by admin on Wed Apr 02 08:24:07 GMT 2025
|
PRIMARY | |||
|
CYPROHEPTADINE
Created by
admin on Wed Apr 02 08:24:07 GMT 2025 , Edited by admin on Wed Apr 02 08:24:07 GMT 2025
|
PRIMARY | |||
|
872
Created by
admin on Wed Apr 02 08:24:07 GMT 2025 , Edited by admin on Wed Apr 02 08:24:07 GMT 2025
|
PRIMARY | |||
|
SUB06875MIG
Created by
admin on Wed Apr 02 08:24:07 GMT 2025 , Edited by admin on Wed Apr 02 08:24:07 GMT 2025
|
PRIMARY | |||
|
Cyproheptadine
Created by
admin on Wed Apr 02 08:24:07 GMT 2025 , Edited by admin on Wed Apr 02 08:24:07 GMT 2025
|
PRIMARY | |||
|
129-03-3
Created by
admin on Wed Apr 02 08:24:07 GMT 2025 , Edited by admin on Wed Apr 02 08:24:07 GMT 2025
|
PRIMARY | |||
|
DB00434
Created by
admin on Wed Apr 02 08:24:07 GMT 2025 , Edited by admin on Wed Apr 02 08:24:07 GMT 2025
|
PRIMARY | |||
|
277
Created by
admin on Wed Apr 02 08:24:07 GMT 2025 , Edited by admin on Wed Apr 02 08:24:07 GMT 2025
|
PRIMARY | |||
|
m4040
Created by
admin on Wed Apr 02 08:24:07 GMT 2025 , Edited by admin on Wed Apr 02 08:24:07 GMT 2025
|
PRIMARY | Merck Index | ||
|
DTXSID8022872
Created by
admin on Wed Apr 02 08:24:07 GMT 2025 , Edited by admin on Wed Apr 02 08:24:07 GMT 2025
|
PRIMARY | |||
|
2YHB6175DO
Created by
admin on Wed Apr 02 08:24:07 GMT 2025 , Edited by admin on Wed Apr 02 08:24:07 GMT 2025
|
PRIMARY | |||
|
2913
Created by
admin on Wed Apr 02 08:24:07 GMT 2025 , Edited by admin on Wed Apr 02 08:24:07 GMT 2025
|
PRIMARY | |||
|
CHEMBL516
Created by
admin on Wed Apr 02 08:24:07 GMT 2025 , Edited by admin on Wed Apr 02 08:24:07 GMT 2025
|
PRIMARY | |||
|
C61695
Created by
admin on Wed Apr 02 08:24:07 GMT 2025 , Edited by admin on Wed Apr 02 08:24:07 GMT 2025
|
PRIMARY | |||
|
3048
Created by
admin on Wed Apr 02 08:24:07 GMT 2025 , Edited by admin on Wed Apr 02 08:24:07 GMT 2025
|
PRIMARY | |||
|
D003533
Created by
admin on Wed Apr 02 08:24:07 GMT 2025 , Edited by admin on Wed Apr 02 08:24:07 GMT 2025
|
PRIMARY | |||
|
204-928-9
Created by
admin on Wed Apr 02 08:24:07 GMT 2025 , Edited by admin on Wed Apr 02 08:24:07 GMT 2025
|
PRIMARY |
ACTIVE MOIETY
METABOLITE (PARENT)
METABOLITE (PARENT)
METABOLITE (PARENT)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)