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Details

Stereochemistry ACHIRAL
Molecular Formula C21H21N.C5H6O5
Molecular Weight 433.4973
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of GLUTODINE

SMILES

CN1CCC(=C2c3ccccc3C=Cc4ccccc42)CC1.C(CC(=O)O)C(=O)C(=O)O

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)

HIDE SMILES / InChI

Description
Curator's Comment:: 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

Targets

Targets

Primary TargetPharmacologyConditionPotency
2.70000000000000018 nM [Ki]
6.5 nM [Ki]
8.80000000000000071 null [pKi]
19 nM [Ki]
0.537000000000000033 nM [Ki]
1.60000000000000009 nM [Ki]
11 nM [Ki]
Conditions

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

316224000000
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

316224000000
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

316224000000
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

316224000000
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

316224000000
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

316224000000
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

316224000000
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

-259113600000
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

-259113600000
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

-259113600000
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
Recommended
dose: 0.227 mg/kg 3 times / day
route: digestive tract route
experiment_type: multiple
dose_type: Recommended
co-adm with
    data_source:
    https://pubmed.ncbi.nlm.nih.gov/27194450/
    unhealthy, 17.6 month
    population: unhealthy
    age: 17.6 month
    sex: M+F
    food_status:
    n:
    data_source:
    https://pubmed.ncbi.nlm.nih.gov/27194450/
    Other AEs: Sleepiness, Constipation...
    Other AEs:
    Sleepiness (4 patients)
    Constipation (3 patients)
    Abnormal behaviour NOS (2 patients)

    data_source:
    https://pubmed.ncbi.nlm.nih.gov/27194450/
    22.5 mg single, oral
    dose: 22.5 mg
    route: oral
    experiment_type: single
    dose_type:
    co-adm with
      data_source:
      https://pubmed.ncbi.nlm.nih.gov/2699315/
      healthy, 4
      population: healthy
      age: 4
      sex:
      food_status:
      n:
      data_source:
      https://pubmed.ncbi.nlm.nih.gov/2699315/
      Other AEs: Disorientation, Abnormal behaviour...
      Other AEs:
      Disorientation
      Abnormal behaviour

      data_source:
      https://pubmed.ncbi.nlm.nih.gov/2699315/
      6 mg multiple, digestive tract route
      Recommended
      dose: 6 mg
      route: digestive tract route
      experiment_type: multiple
      dose_type: Recommended
      co-adm with
        data_source:
        https://pubmed.ncbi.nlm.nih.gov/23419589/
        unhealthy, 9.8
        population: unhealthy
        age: 9.8
        sex: M+F
        food_status:
        n:
        data_source:
        https://pubmed.ncbi.nlm.nih.gov/23419589/
        Other AEs: Somnolence, Irritability...
        Other AEs:
        Somnolence (16%)
        Irritability (6%)
        Increased appetite (5%)
        Abdominal pain (2.5%)

        data_source:
        https://pubmed.ncbi.nlm.nih.gov/23419589/
        32 mg multiple, oral
        Recommended
        dose: 32 mg
        route: oral
        experiment_type: multiple
        dose_type: Recommended
        co-adm with
          data_source:
          https://pubmed.ncbi.nlm.nih.gov/638709/
          unhealthy, <40
          population: unhealthy
          age: <40
          sex:
          food_status:
          n:
          data_source:
          https://pubmed.ncbi.nlm.nih.gov/638709/
          Other AEs: Weight gain, Drowsiness...
          Other AEs:
          Weight gain (19 patients)
          Drowsiness

          data_source:
          https://pubmed.ncbi.nlm.nih.gov/638709/
          AEs

          AEs

          AESignificanceDosePopulation
          Abnormal behaviour
          22.5 mg single, oral
          dose: 22.5 mg
          route: oral
          experiment_type: single
          dose_type:
          co-adm with
            data_source:
            https://pubmed.ncbi.nlm.nih.gov/2699315/
            healthy, 4
            population:
            age:
            sex:
            food_status:
            n:
            data_source:
            https://pubmed.ncbi.nlm.nih.gov/2699315/
            Disorientation
            22.5 mg single, oral
            dose: 22.5 mg
            route: oral
            experiment_type: single
            dose_type:
            co-adm with
              data_source:
              https://pubmed.ncbi.nlm.nih.gov/2699315/
              healthy, 4
              population:
              age:
              sex:
              food_status:
              n:
              data_source:
              https://pubmed.ncbi.nlm.nih.gov/2699315/
              Drowsiness
              32 mg multiple, oral
              Recommended
              dose: 32 mg
              route: oral
              experiment_type: multiple
              dose_type: Recommended
              co-adm with
                data_source:
                https://pubmed.ncbi.nlm.nih.gov/638709/
                unhealthy, <40
                population:
                age:
                sex:
                food_status:
                n:
                data_source:
                https://pubmed.ncbi.nlm.nih.gov/638709/
                Weight gain 19 pts%
                32 mg multiple, oral
                Recommended
                dose: 32 mg
                route: oral
                experiment_type: multiple
                dose_type: Recommended
                co-adm with
                  data_source:
                  https://pubmed.ncbi.nlm.nih.gov/638709/
                  unhealthy, <40
                  population:
                  age:
                  sex:
                  food_status:
                  n:
                  data_source:
                  https://pubmed.ncbi.nlm.nih.gov/638709/
                  Somnolence 16%
                  6 mg multiple, digestive tract route
                  Recommended
                  dose: 6 mg
                  route: digestive tract route
                  experiment_type: multiple
                  dose_type: Recommended
                  co-adm with
                    data_source:
                    https://pubmed.ncbi.nlm.nih.gov/23419589/
                    unhealthy, 9.8
                    population:
                    age:
                    sex:
                    food_status:
                    n:
                    data_source:
                    https://pubmed.ncbi.nlm.nih.gov/23419589/
                    Abdominal pain 2.5%
                    6 mg multiple, digestive tract route
                    Recommended
                    dose: 6 mg
                    route: digestive tract route
                    experiment_type: multiple
                    dose_type: Recommended
                    co-adm with
                      data_source:
                      https://pubmed.ncbi.nlm.nih.gov/23419589/
                      unhealthy, 9.8
                      population:
                      age:
                      sex:
                      food_status:
                      n:
                      data_source:
                      https://pubmed.ncbi.nlm.nih.gov/23419589/
                      Increased appetite 5%
                      6 mg multiple, digestive tract route
                      Recommended
                      dose: 6 mg
                      route: digestive tract route
                      experiment_type: multiple
                      dose_type: Recommended
                      co-adm with
                        data_source:
                        https://pubmed.ncbi.nlm.nih.gov/23419589/
                        unhealthy, 9.8
                        population:
                        age:
                        sex:
                        food_status:
                        n:
                        data_source:
                        https://pubmed.ncbi.nlm.nih.gov/23419589/
                        Irritability 6%
                        6 mg multiple, digestive tract route
                        Recommended
                        dose: 6 mg
                        route: digestive tract route
                        experiment_type: multiple
                        dose_type: Recommended
                        co-adm with
                          data_source:
                          https://pubmed.ncbi.nlm.nih.gov/23419589/
                          unhealthy, 9.8
                          population:
                          age:
                          sex:
                          food_status:
                          n:
                          data_source:
                          https://pubmed.ncbi.nlm.nih.gov/23419589/
                          Abnormal behaviour NOS 2 pts%
                          0.227 mg/kg 3 times / day multiple, digestive tract route
                          Recommended
                          dose: 0.227 mg/kg 3 times / day
                          route: digestive tract route
                          experiment_type: multiple
                          dose_type: Recommended
                          co-adm with
                            data_source:
                            https://pubmed.ncbi.nlm.nih.gov/27194450/
                            unhealthy, 17.6 month
                            population:
                            age:
                            sex:
                            food_status:
                            n:
                            data_source:
                            https://pubmed.ncbi.nlm.nih.gov/27194450/
                            Constipation 3 pts%
                            0.227 mg/kg 3 times / day multiple, digestive tract route
                            Recommended
                            dose: 0.227 mg/kg 3 times / day
                            route: digestive tract route
                            experiment_type: multiple
                            dose_type: Recommended
                            co-adm with
                              data_source:
                              https://pubmed.ncbi.nlm.nih.gov/27194450/
                              unhealthy, 17.6 month
                              population:
                              age:
                              sex:
                              food_status:
                              n:
                              data_source:
                              https://pubmed.ncbi.nlm.nih.gov/27194450/
                              Sleepiness 4 pts%
                              0.227 mg/kg 3 times / day multiple, digestive tract route
                              Recommended
                              dose: 0.227 mg/kg 3 times / day
                              route: digestive tract route
                              experiment_type: multiple
                              dose_type: Recommended
                              co-adm with
                                data_source:
                                https://pubmed.ncbi.nlm.nih.gov/27194450/
                                unhealthy, 17.6 month
                                population:
                                age:
                                sex:
                                food_status:
                                n:
                                data_source:
                                https://pubmed.ncbi.nlm.nih.gov/27194450/
                                Overview

                                Overview

                                CYP3A4CYP2C9CYP2D6hERG

                                OverviewOther

                                Other InhibitorOther SubstrateOther Inducer






                                Drug as perpetrator​Drug as victimTox targets

                                Tox targets

                                TargetModalityActivityMetaboliteClinical evidence
                                Sourcing
                                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-HT2C receptor: from the choroid plexus to depression, obesity and addiction treatment.
                                2017 May
                                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
                                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.
                                Name Type Language
                                GLUTODINE
                                Common Name English
                                CYPROHEPTADINE ALPHAKETOGLUTARATE [WHO-DD]
                                Common Name English
                                ALPHA-KETOGLUTARATE CYPROHEPTADINE
                                Common Name English
                                .ALPHA.-KETOGLUTARATE CYPROHEPTADINE
                                Common Name English
                                CYPROHEPTADINE ALPHAKETOGLUTARATE
                                WHO-DD  
                                Common Name English
                                PENTANEDIOIC ACID, 2-OXO-, COMPD. WITH 4-(5H-DIBENZO(A,D)CYCLOHEPTEN-5-YLIDENE)-1-METHYLPIPERIDINE (1:1)
                                Systematic Name English
                                DYNAMOGEN
                                Brand Name English
                                PIPERIDINE, 4-(5H-DIBENZO(A,D)CYCLOHEPTEN-5-YLIDENE)-1-METHYL-, 2-OXOPENTANEDIOATE (1:1)
                                Systematic Name English
                                Code System Code Type Description
                                FDA UNII
                                Z7L8L2CX3Y
                                Created by admin on Sat Jun 26 09:02:59 UTC 2021 , Edited by admin on Sat Jun 26 09:02:59 UTC 2021
                                PRIMARY
                                PUBCHEM
                                91617999
                                Created by admin on Sat Jun 26 09:02:59 UTC 2021 , Edited by admin on Sat Jun 26 09:02:59 UTC 2021
                                PRIMARY
                                CAS
                                58131-49-0
                                Created by admin on Sat Jun 26 09:02:59 UTC 2021 , Edited by admin on Sat Jun 26 09:02:59 UTC 2021
                                PRIMARY