cyproheptadine Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
histamine-H1 receptor antagonists, tricyclic compounds 765 129-03-3

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • periactin
  • cyproheptadine
  • cyproheptadine hydrochloride
  • cycloheptadine
  • periactinol
  • cyproheptadine HCl
A serotonin antagonist and a histamine H1 blocker used as antipruritic, appetite stimulant, antiallergic, and for the post-gastrectomy dumping syndrome, etc.
  • Molecular weight: 287.41
  • Formula: C21H21N
  • CLOGP: 5.30
  • LIPINSKI: 1
  • HAC: 1
  • HDO: 0
  • TPSA: 3.24
  • ALOGS: -4.33
  • ROTB: 0

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
12 mg O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 3.64 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 0.50 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 1.74 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD

Approvals:

DateAgencyCompanyOrphan
Oct. 17, 1961 FDA

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Cardiac arrest 87.13 66.47 21 130 14909 2343025
Cardiogenic shock 70.56 66.47 13 138 2478 2355456

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Serotonin syndrome 169.88 74.39 28 75 2760 1743918
Intentional overdose 111.12 74.39 23 80 7647 1739031

Pharmacologic Action:

SourceCodeDescription
ATC R06AX02 RESPIRATORY SYSTEM
ANTIHISTAMINES FOR SYSTEMIC USE
ANTIHISTAMINES FOR SYSTEMIC USE
Other antihistamines for systemic use
CHEBI has role CHEBI:37955 H1-receptor antagonist
CHEBI has role CHEBI:48279 serotonergic antagonist
CHEBI has role CHEBI:59683 antipruritic drug
CHEBI has role CHEBI:50857 anti-allergic agent
CHEBI has role CHEBI:55324 gastrointestinal drug
MeSH PA D018926 Anti-Allergic Agents
MeSH PA D000982 Antipruritics
MeSH PA D003879 Dermatologic Agents
MeSH PA D005765 Gastrointestinal Agents
MeSH PA D018494 Histamine Agents
MeSH PA D006633 Histamine Antagonists
MeSH PA D006634 Histamine H1 Antagonists
MeSH PA D018377 Neurotransmitter Agents
MeSH PA D018490 Serotonin Agents
MeSH PA D012702 Serotonin Antagonists

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Dermatographic urticaria indication 7632005 DOID:743
Allergic rhinitis indication 61582004
Nasal discharge indication 64531003
Nasal congestion indication 68235000
Sneezing indication 76067001
Urticaria indication 126485001
Itching of skin indication 418363000
Allergic conjunctivitis indication 473460002 DOID:11204
Serotonin syndrome off-label use 371089000
Muscle spasticity of spinal origin off-label use 416830008
Ocular hypertension contraindication 4210003 DOID:9282
Peptic ulcer contraindication 13200003 DOID:750
Hyperthyroidism contraindication 34486009 DOID:7998
Hypertensive disorder contraindication 38341003 DOID:10763
Chronic idiopathic constipation contraindication 82934008
Bladder outflow obstruction contraindication 236645006
Benign prostatic hyperplasia contraindication 266569009
Retention of urine contraindication 267064002
Angle-closure glaucoma contraindication 392291006 DOID:13550

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 8.8 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Histamine H1 receptor GPCR ANTAGONIST Ki 10.22 WOMBAT-PK CHEMBL
5-hydroxytryptamine receptor 1D GPCR Ki 5.89 PDSP
Alpha-2A adrenergic receptor GPCR Ki 6.97 DRUG MATRIX
Potassium voltage-gated channel subfamily H member 2 Ion channel Ki 4.85 DRUG MATRIX
Alpha-2B adrenergic receptor GPCR Ki 7.77 DRUG MATRIX
Histamine H2 receptor GPCR Ki 6.71 DRUG MATRIX
Muscarinic acetylcholine receptor M4 GPCR Ki 8.66 DRUG MATRIX
Muscarinic acetylcholine receptor M5 GPCR Ki 8.56 DRUG MATRIX
Alpha-2C adrenergic receptor GPCR Ki 6.73 DRUG MATRIX
Sodium-dependent noradrenaline transporter Transporter Ki 6.54 CHEMBL
Sodium channel alpha subunits; brain (Types I, II, III) Ion channel IC50 6 CHEMBL
Sodium-dependent serotonin transporter Transporter Ki 5.39 CHEMBL
5-hydroxytryptamine receptor 2C GPCR Ki 8.65 WOMBAT-PK
5-hydroxytryptamine receptor 2B GPCR Ki 8.81 WOMBAT-PK
5-hydroxytryptamine receptor 2A GPCR Ki 8.42 WOMBAT-PK
Calmodulin Cytosolic other WOMBAT-PK
Alpha-1B adrenergic receptor GPCR Ki 7.60 WOMBAT-PK
Muscarinic acetylcholine receptor M3 GPCR Ki 8 WOMBAT-PK
Muscarinic acetylcholine receptor M2 GPCR Ki 8 WOMBAT-PK
Muscarinic acetylcholine receptor M1 GPCR Ki 8 WOMBAT-PK
Histamine H4 receptor GPCR Ki 8.19 WOMBAT-PK
D(3) dopamine receptor GPCR Ki 8.10 WOMBAT-PK
Alpha-1A adrenergic receptor GPCR Ki 7.40 WOMBAT-PK
5-hydroxytryptamine receptor 1A GPCR Ki 7.23 WOMBAT-PK
Multidrug resistance protein 1 Transporter WOMBAT-PK
Alpha-1D adrenergic receptor GPCR Ki 6.90 WOMBAT-PK
5-hydroxytryptamine receptor 7 GPCR Ki 6.90 WOMBAT-PK
5-hydroxytryptamine receptor 6 GPCR Ki 6.80 WOMBAT-PK
D(2) dopamine receptor GPCR Ki 6.95 WOMBAT-PK
D(1A) dopamine receptor GPCR Ki 6.93 WOMBAT-PK
Histone-lysine N-methyltransferase SETD7 Unclassified IC50 4.70 CHEMBL
Alpha-1B adrenergic receptor GPCR Ki 7.36 DRUG MATRIX
5-hydroxytryptamine receptor 1B GPCR Ki 5.90 DRUG MATRIX
Serotonin 2 (5-HT2) receptor GPCR IC50 8.51 CHEMBL
Dopamine receptor GPCR Ki 7.20 CHEMBL
Sodium-dependent noradrenaline transporter Transporter Ki 6.54 CHEMBL
D(2) dopamine receptor GPCR IC50 6.85 CHEMBL
Histamine H1 receptor GPCR Kd 9 CHEMBL
5-hydroxytryptamine receptor 2C GPCR Ki 7.96 CHEMBL
5-hydroxytryptamine receptor 7 GPCR Ki 7.30 CHEMBL
Muscarinic acetylcholine receptor GPCR Ki 8.40 CHEMBL
D(2) dopamine receptor GPCR Ki 6.95 CHEMBL
Sodium-dependent serotonin transporter Transporter Ki 5.39 CHEMBL
5-hydroxytryptamine receptor 2A GPCR Ki 8.80 CHEMBL
5-hydroxytryptamine receptor 1A GPCR IC50 6.91 CHEMBL
Alpha-1A adrenergic receptor GPCR IC50 6.62 CHEMBL
5-hydroxytryptamine receptor 6 GPCR ANTAGONIST Ki 6.90 IUPHAR

External reference:

IDSource
D003533 MESH_DESCRIPTOR_UI
4019701 VUID
N0000147793 NUI
C0010620 UMLSCUI
D02234 KEGG_DRUG
2YHB6175DO UNII
872 INN_ID
26462003 SNOMEDCT_US
4019701 VANDF
004617 NDDF
3013 RXNORM
372683000 SNOMEDCT_US
d00790 MMSL
CHEBI:4046 CHEBI
CHEMBL516 ChEMBL_ID
DB00434 DRUGBANK_ID
CHEMBL1716 ChEMBL_ID
41354-29-4 SECONDARY_CAS_RN
C7H PDB_CHEM_ID
277 IUPHAR_LIGAND_ID
2913 PUBCHEM_CID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Cyproheptadine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0115-1757 TABLET 4 mg ORAL ANDA 11 sections
CYPROHEPTADINE HUMAN PRESCRIPTION DRUG LABEL 1 0121-0788 SYRUP 2 mg ORAL ANDA 12 sections
CYPROHEPTADINE HUMAN PRESCRIPTION DRUG LABEL 1 0121-4788 SYRUP 2 mg ORAL ANDA 12 sections
CYPROHEPTADINE HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 0463-6080 TABLET 4 mg ORAL ANDA 10 sections
Cyproheptadine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0527-1949 SOLUTION 2 mg ORAL ANDA 11 sections
Cyproheptadine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0615-1536 TABLET 4 mg ORAL ANDA 11 sections
Cyproheptadine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 10135-638 TABLET 4 mg ORAL ANDA 12 sections
cyproheptadine hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 23155-703 TABLET 4 mg ORAL ANDA 11 sections
Cyproheptadine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 24689-816 TABLET 4 mg ORAL ANDA 2 sections
Cyproheptadine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 39328-044 SOLUTION 2 mg ORAL ANDA 11 sections
CYPROHEPTADINE HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 42291-225 TABLET 4 mg ORAL ANDA 11 sections
Cyproheptadine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 50090-4724 TABLET 4 mg ORAL ANDA 12 sections
CYPROHEPTADINE HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 50488-5002 TABLET 4 mg ORAL ANDA 12 sections
CYPROHEPTADINE HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 50742-190 TABLET 4 mg ORAL ANDA 11 sections
CYPROHEPTADINE HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 51407-272 TABLET 4 mg ORAL ANDA 11 sections
CYPROHEPTADINE HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 51991-838 TABLET 4 mg ORAL ANDA 12 sections
Cyproheptadine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 52817-210 TABLET 4 mg ORAL ANDA 11 sections
Cyproheptadine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 53808-0829 TABLET 4 mg ORAL ANDA 11 sections
Cyproheptadine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 53808-1030 TABLET 4 mg ORAL ANDA 11 sections
Cyproheptadine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 54868-1332 TABLET 4 mg ORAL ANDA 11 sections
Cyproheptadine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 54868-4338 SYRUP 2 mg ORAL ANDA 19 sections
CYPROHEPTADINE HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 55700-700 TABLET 4 mg ORAL ANDA 11 sections
Cyproheptadine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 60429-849 TABLET 4 mg ORAL ANDA 11 sections
Cyproheptadine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 62033-0346 TABLET 4 mg ORAL Export only 10 sections
CYPROHEPTADINE HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 64380-795 TABLET 4 mg ORAL ANDA 11 sections
Cyproheptadine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 64980-504 SYRUP 2 mg ORAL ANDA 12 sections
Cyproheptadine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 66689-333 SOLUTION 2 mg ORAL ANDA 11 sections
Cyproheptadine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 68151-1728 SYRUP 2 mg ORAL ANDA 18 sections
CYPROHEPTADINE HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 68151-2506 TABLET 4 mg ORAL ANDA 11 sections
Cyproheptadine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 69339-135 TABLET 4 mg ORAL ANDA 11 sections