Details
Stereochemistry | ACHIRAL |
Molecular Formula | C21H21N.C5H6O5 |
Molecular Weight | 433.4963 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(=O)CCC(=O)C(O)=O.CN1CCC(CC1)=C2C3=C(C=CC=C3)C=CC4=C2C=CC=C4
InChI
InChIKey=LFIWQECRMKMNIM-UHFFFAOYSA-N
InChI=1S/C21H21N.C5H6O5/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;6-3(5(9)10)1-2-4(7)8/h2-11H,12-15H2,1H3;1-2H2,(H,7,8)(H,9,10)
DescriptionSources: https://www.drugs.com/dosage/cyproheptadine.htmlhttps://www.accessdata.fda.gov/drugsatfda_docs/label/2009/087056s045lbl.pdfCurator'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
Sources: https://www.drugs.com/dosage/cyproheptadine.htmlhttps://www.accessdata.fda.gov/drugsatfda_docs/label/2009/087056s045lbl.pdf
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.
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 |
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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 |
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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 |
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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 |
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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 |
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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 |
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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 |
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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 |
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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 |
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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 |
---|---|---|---|---|
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 |
---|---|---|---|---|
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://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 (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) Sources: Constipation (3 patients) Abnormal behaviour NOS (2 patients) |
22.5 mg single, oral |
healthy, 4 n = 1 Health Status: healthy Age Group: 4 Population Size: 1 Sources: |
Other AEs: Disorientation, Abnormal behaviour... |
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%) Sources: Irritability (6%) Increased appetite (5%) Abdominal pain (2.5%) |
32 mg multiple, oral Recommended |
unhealthy, <40 n = 20 Health Status: unhealthy Condition: endocrine disorders Age Group: <40 Population Size: 20 Sources: |
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 (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 |
healthy, 4 n = 1 Health Status: healthy Age Group: 4 Population Size: 1 Sources: |
|
Disorientation | 22.5 mg single, oral |
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 |
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 |
unhealthy, <40 n = 20 Health Status: unhealthy Condition: endocrine disorders Age Group: <40 Population Size: 20 Sources: |
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 |
PubMed
Title | Date | PubMed |
---|---|---|
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 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/dosage/cyproheptadine.html
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26454215
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
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Z7L8L2CX3Y
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100000129297
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91617999
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58131-49-0
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ACTIVE MOIETY
SUBSTANCE RECORD