cyproheptadine 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | PK/Tox | Related Drugs | 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: 5.16
  • 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 µM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD

Predicted pharmacokinetic/toxicological properties (PK-AZ):

PropertyDescriptionValueUnitConfidenceSimilarity
kinase-safety-class ACVR2A,ACVR2B,AKT2,AKT3,AURKA,AXL,BRAF,BTK,CAMK2B,CAMK2D,CDK4,CDK5,CDK9,CHEK1,DDR1,DYRK1B,EIF2AK3,EPHB4,ERBB2,FLT3,GRK2,GSK3B,ITK,JAK2,JAK3,MAP3K21,MAP3K7,MAPK10,MAPK7,MAPK9,MAPKAPK2,MET,MTOR,NTRK2,PDK4,PDPK1,PIK3CB,PIM2,PRKCD,PRKDC,SIK2,SIK3,STK33,TEK,TGFBR1,TTK 46
kinase-selectivity-class ACVR2B,AXL,BRAF,CAMK2D,MAPK7,SIK2,STK33,TTK 8
pfas-class PFAS structural alert (1 = True, 0 = False) 0

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
Infective pulmonary exacerbation of cystic fibrosis 209.57 19.94 59 5515 10220 90612653
Torus fracture 116.26 19.94 18 5556 151 90622722
Growth retardation 73.95 19.94 18 5556 1765 90621108
Serotonin syndrome 73.34 19.94 39 5535 37848 90585025
Agitation 62.04 19.94 43 5531 67055 90555818
Immobile 51.24 19.94 18 5556 6380 90616493
Irritability 38.08 19.94 25 5549 35637 90587236
Apallic syndrome 37.98 19.94 9 5565 787 90622086
Butterfly rash 37.60 19.94 11 5563 2174 90620699
Oesophageal spasm 36.96 19.94 12 5562 3349 90619524
Juvenile idiopathic arthritis 34.97 19.94 12 5562 3965 90618908
Hospitalisation 34.60 19.94 41 5533 128059 90494814
Bone density decreased 33.96 19.94 18 5556 17327 90605546
Oesophageal pain 33.86 19.94 12 5562 4362 90618511
Mood swings 33.66 19.94 19 5555 20683 90602190
Hallucination 32.15 19.94 29 5545 65930 90556943
Sleep apnoea syndrome 30.87 19.94 21 5553 31726 90591147
Malnutrition 30.08 19.94 17 5557 18541 90604332
Crying 27.43 19.94 18 5556 25627 90597246
Intentional overdose 26.94 19.94 31 5543 93803 90529070
Disturbance in social behaviour 26.86 19.94 10 5564 4178 90618695
Hallucination, tactile 26.41 19.94 6 5568 436 90622437
Dermatitis atopic 26.39 19.94 17 5557 23455 90599418
Mydriasis 25.00 19.94 14 5560 14998 90607875
Regurgitation 24.90 19.94 8 5566 2158 90620715
Mental status changes 24.49 19.94 21 5553 44658 90578215
Central obesity 23.93 19.94 7 5567 1383 90621490
Lymphoedema 23.38 19.94 13 5561 13740 90609133
Aggression 22.10 19.94 16 5558 26652 90596221
Psychomotor hyperactivity 21.48 19.94 12 5562 12801 90610072
Sinus tachycardia 21.15 19.94 16 5558 28497 90594376
Cardiogenic shock 21.01 19.94 15 5559 24453 90598420
Mood altered 20.72 19.94 13 5561 17131 90605742
Cystic fibrosis 20.22 19.94 8 5566 3933 90618940

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
Infective pulmonary exacerbation of cystic fibrosis 169.13 20.67 53 4412 7765 42609105
Serotonin syndrome 164.17 20.67 71 4394 25774 42591096
Nasal polyps 66.43 20.67 22 4443 3829 42613041
Chronic sinusitis 65.07 20.67 21 4444 3371 42613499
Nasal congestion 45.98 20.67 32 4433 29469 42587401
Drug dependence 44.04 20.67 31 4434 29063 42587807
Cystic fibrosis 40.54 20.67 13 4452 2042 42614828
Irritability 40.34 20.67 29 4436 28099 42588771
Withdrawal syndrome 37.99 20.67 22 4443 14753 42602117
Clonus 37.30 20.67 14 4451 3506 42613364
Rhinorrhoea 37.16 20.67 29 4436 31765 42585105
Mood swings 36.40 20.67 18 4447 8808 42608062
Symptom masked 32.32 20.67 9 4456 872 42615998
Cystic fibrosis respiratory infection suppression 31.49 20.67 7 4458 268 42616602
Obsessive-compulsive symptom 27.08 20.67 6 4459 226 42616644
Anti-saccharomyces cerevisiae antibody 26.03 20.67 4 4461 17 42616853
Obsessive-compulsive disorder 25.59 20.67 13 4452 6730 42610140
Viral infection 25.17 20.67 20 4445 22463 42594407
Restlessness 24.47 20.67 22 4443 29227 42587643
Abdominal pain 24.01 20.67 58 4407 190413 42426457
Hospitalisation 23.98 20.67 34 4431 74296 42542574
Decreased appetite 22.42 20.67 57 4408 193080 42423790

FDA Adverse Event Reporting System (Geriatric)

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
Infective pulmonary exacerbation of cystic fibrosis 305.96 16.93 91 8754 14680 110565774
Serotonin syndrome 235.16 16.93 108 8737 59045 110521409
Irritability 74.85 16.93 47 8798 47762 110532692
Torus fracture 64.35 16.93 11 8834 135 110580319
Mood swings 61.54 16.93 32 8813 22780 110557674
Drug dependence 58.49 16.93 41 8804 49979 110530475
Nasal polyps 52.06 16.93 24 8821 13176 110567278
Withdrawal syndrome 52.02 16.93 32 8813 31348 110549106
Agitation 51.66 16.93 54 8791 112997 110467457
Cystic fibrosis 48.08 16.93 17 8828 4714 110575740
Intentional overdose 43.01 16.93 53 8792 132448 110448006
Growth retardation 41.07 16.93 13 8832 2569 110577885
Obsessive-compulsive disorder 41.05 16.93 17 8828 7224 110573230
Mental status changes 39.58 16.93 39 8806 76083 110504371
Clonus 38.01 16.93 17 8828 8699 110571755
Restlessness 37.30 16.93 33 8812 56226 110524228
Hospitalisation 36.91 16.93 51 8794 142442 110438012
Symptom masked 36.29 16.93 11 8834 1884 110578570
Chronic sinusitis 35.13 16.93 23 8822 25061 110555393
Butterfly rash 35.02 16.93 11 8834 2120 110578334
Oesophageal spasm 32.84 16.93 12 8833 3654 110576800
Apallic syndrome 32.70 16.93 9 8836 1097 110579357
Pulmonary function test decreased 31.77 16.93 15 8830 8685 110571769
Malnutrition 31.04 16.93 22 8823 27257 110553197
Dermatitis atopic 30.00 16.93 21 8824 25520 110554934
Oesophageal pain 28.94 16.93 12 8833 5113 110575341
Nasal congestion 28.22 16.93 37 8808 98245 110482209
Anti-saccharomyces cerevisiae antibody 27.11 16.93 4 8841 17 110580437
Juvenile idiopathic arthritis 27.10 16.93 12 8833 5995 110574459
Obsessive-compulsive symptom 26.61 16.93 6 8839 323 110580131
Aggression 26.53 16.93 28 8817 59182 110521272
Regurgitation 26.09 16.93 10 8835 3475 110576979
Crying 25.37 16.93 19 8826 25609 110554845
Sleep apnoea syndrome 25.37 16.93 23 8822 40424 110540030
Suicide attempt 25.27 16.93 36 8809 103358 110477096
Hyperreflexia 24.70 16.93 13 8832 9472 110570982
Cystic fibrosis respiratory infection suppression 24.24 16.93 6 8839 483 110579971
Hyperthermia 23.85 16.93 17 8828 21255 110559199
Electrocardiogram QT prolonged 23.82 16.93 36 8809 108924 110471530
Pneumonia aspiration 22.42 16.93 30 8815 81203 110499251
Tachycardia 22.06 16.93 53 8792 226592 110353862
Muscle rigidity 21.99 16.93 17 8828 24014 110556440
Gastric hypomotility 21.64 16.93 5 8840 300 110580154
Decreased appetite 21.48 16.93 85 8760 475761 110104693
Immobile 21.33 16.93 11 8834 7691 110572763
Rhinorrhoea 21.15 16.93 33 8812 102633 110477821
Drug interaction 19.95 16.93 86 8759 500097 110080357
Hallucination, tactile 19.90 16.93 6 8839 1009 110579445
Medulloblastoma 19.73 16.93 4 8841 129 110580325
Sedation 19.64 16.93 26 8819 69657 110510797
Respiratory failure 19.52 16.93 49 8796 215283 110365171
Central obesity 19.49 16.93 7 8838 2029 110578425
Disturbance in social behaviour 19.33 16.93 9 8836 5049 110575405
Lymphoedema 19.24 16.93 13 8832 14916 110565538
Mydriasis 18.82 16.93 15 8830 22142 110558312
Abdominal pain 18.79 16.93 86 8759 512903 110067551
Product dose omission issue 18.32 16.93 62 8783 321720 110258734
Limb asymmetry 17.82 16.93 5 8840 653 110579801
Psychomotor hyperactivity 17.81 16.93 14 8831 20263 110560191
Palpitations 17.43 16.93 39 8806 159173 110421281
Intentional product misuse 17.37 16.93 35 8810 132869 110447585
Mood altered 17.16 16.93 14 8831 21361 110559093

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC R06AX02 RESPIRATORY SYSTEM
ANTIHISTAMINES FOR SYSTEMIC USE
ANTIHISTAMINES FOR SYSTEMIC USE
Other antihistamines for systemic use
MeSH PA D000982 Antipruritics
MeSH PA D003879 Dermatologic Agents
MeSH PA D005765 Gastrointestinal Agents
MeSH PA D006633 Histamine Antagonists
MeSH PA D006634 Histamine H1 Antagonists
MeSH PA D012702 Serotonin Antagonists
MeSH PA D018377 Neurotransmitter Agents
MeSH PA D018490 Serotonin Agents
MeSH PA D018926 Anti-Allergic Agents
CHEBI has role CHEBI:22587 antiviral agent
CHEBI has role CHEBI:35480 analgesic
CHEBI has role CHEBI:37955 H<small><sub>1</sub></small>-receptor antagonist
CHEBI has role CHEBI:48279 serotonergic antagonist
CHEBI has role CHEBI:50857 anti-allergic agent
CHEBI has role CHEBI:55324 gastrointestinal drug
CHEBI has role CHEBI:59683 antipruritic drug

Related Drugs by ATC class:

R06AX Other antihistamines for systemic use 26 drugs
acrivastineantazolineastemizoleazatadineazelastinebamipinebilastinedeptropinedesloratadineebastineepinastinefexofenadine show all 26 →

Drug Use | Suggest Off label Use Form| |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
SSRI induced sexual dysfunction off-label use 425528008
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




🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

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 6 GPCR Ki 6.80 WOMBAT-PK
5-hydroxytryptamine receptor 7 GPCR Ki 6.90 WOMBAT-PK
Alpha-1A adrenergic receptor GPCR Ki 7.40 WOMBAT-PK
5-hydroxytryptamine receptor 2B GPCR Ki 8.81 WOMBAT-PK
D(1A) dopamine receptor GPCR Ki 6.93 WOMBAT-PK
D(2) dopamine receptor GPCR Ki 6.95 WOMBAT-PK
Alpha-2A adrenergic receptor GPCR Ki 6.98 DRUG MATRIX
Potassium voltage-gated channel subfamily H member 2 Ion channel Ki 4.86 DRUG MATRIX
Multidrug resistance protein 1 Transporter WOMBAT-PK
Sodium-dependent serotonin transporter Transporter Ki 5.39 CHEMBL
Sodium-dependent noradrenaline transporter Transporter Ki 6.54 CHEMBL
5-hydroxytryptamine receptor 1A GPCR Ki 7.23 WOMBAT-PK
5-hydroxytryptamine receptor 2A GPCR Ki 8.42 WOMBAT-PK
Alpha-2B adrenergic receptor GPCR Ki 7.77 DRUG MATRIX
D(3) dopamine receptor GPCR Ki 8.10 WOMBAT-PK
Histamine H2 receptor GPCR Ki 6.71 DRUG MATRIX
Histamine H4 receptor GPCR Ki 8.19 WOMBAT-PK
Muscarinic acetylcholine receptor M1 GPCR Ki 8 WOMBAT-PK
Muscarinic acetylcholine receptor M2 GPCR Ki 8 WOMBAT-PK
Muscarinic acetylcholine receptor M3 GPCR Ki 8 WOMBAT-PK
Muscarinic acetylcholine receptor M4 GPCR Ki 8.66 DRUG MATRIX
Muscarinic acetylcholine receptor M5 GPCR Ki 8.56 DRUG MATRIX
5-hydroxytryptamine receptor 1D GPCR Ki 5.89 PDSP
Alpha-2C adrenergic receptor GPCR Ki 6.73 DRUG MATRIX
Alpha-1D adrenergic receptor GPCR Ki 6.90 WOMBAT-PK
Alpha-1B adrenergic receptor GPCR Ki 7.60 WOMBAT-PK
Calmodulin Cytosolic other WOMBAT-PK
Sodium channel alpha subunits; brain (Types I, II, III) Ion channel IC50 6 CHEMBL
5-hydroxytryptamine receptor 2C GPCR Ki 8.65 WOMBAT-PK
Histone-lysine N-methyltransferase SETD7 Enzyme IC50 4.70 CHEMBL
Alpha-1B adrenergic receptor GPCR Ki 7.36 DRUG MATRIX
5-hydroxytryptamine receptor 1B GPCR Ki 5.90 DRUG MATRIX
Alpha-1A adrenergic receptor GPCR IC50 6.62 CHEMBL
Histamine H1 receptor GPCR Kd 9 CHEMBL
D(2) dopamine receptor GPCR IC50 6.85 CHEMBL
5-hydroxytryptamine receptor 1A GPCR IC50 6.91 CHEMBL
5-hydroxytryptamine receptor 2A GPCR Ki 8.80 CHEMBL
5-hydroxytryptamine receptor 7 GPCR Ki 7.30 CHEMBL
Sodium-dependent noradrenaline transporter Transporter Ki 6.54 CHEMBL
5-hydroxytryptamine receptor 2C GPCR Ki 7.96 CHEMBL
D(2) dopamine receptor GPCR Ki 6.95 CHEMBL
Sodium-dependent serotonin transporter Transporter Ki 5.39 CHEMBL
5-hydroxytryptamine receptor 6 GPCR ANTAGONIST Ki 6.90 IUPHAR
Muscarinic acetylcholine receptor GPCR Ki 8.40 CHEMBL
Dopamine receptor GPCR Ki 7.20 CHEMBL
Serotonin 2 (5-HT2) receptor GPCR IC50 8.51 CHEMBL

External reference:

IDSource
4019701 VUID
N0000147793 NUI
D02234 KEGG_DRUG
41354-29-4 SECONDARY_CAS_RN
104592 RXNORM
C0010620 UMLSCUI
CHEBI:4046 CHEBI
C7H PDB_CHEM_ID
CHEMBL516 ChEMBL_ID
CHEMBL1716 ChEMBL_ID
DB00434 DRUGBANK_ID
D003533 MESH_DESCRIPTOR_UI
2913 PUBCHEM_CID
277 IUPHAR_LIGAND_ID
872 INN_ID
2YHB6175DO UNII
2249 MMSL
331 MMSL
4522 MMSL
d00790 MMSL
001537 NDDF
004617 NDDF
15352003 SNOMEDCT_US
26462003 SNOMEDCT_US
372683000 SNOMEDCT_US
4017931 VANDF
4019701 VANDF

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Cyproheptadine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0115-1757 TABLET 4 mg ORAL ANDA 21 sections
CYPROHEPTADINE HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 0463-6080 TABLET 4 mg ORAL ANDA 11 sections
Cyproheptadine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 10135-638 TABLET 4 mg ORAL ANDA 21 sections
Cyproheptadine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 16571-805 TABLET 4 mg ORAL ANDA 13 sections
Cyproheptadine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 17856-0504 SYRUP 2 mg ORAL ANDA 17 sections
Cyproheptadine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 27808-099 SYRUP 2 mg ORAL ANDA 19 sections
Cyproheptadine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 39328-544 SOLUTION 2 mg ORAL ANDA 21 sections
Cyproheptadine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 42708-177 TABLET 4 mg ORAL ANDA 20 sections
CYPROHEPTADINE HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 42708-187 TABLET 4 mg ORAL ANDA 18 sections
Cyproheptadine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 50090-4724 TABLET 4 mg ORAL ANDA 21 sections
Cyproheptadine Hydrochloride Human Prescription Drug Label 1 50090-5491 TABLET 4 mg ORAL ANDA 20 sections
CYPROHEPTADINE HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 50090-6129 TABLET 4 mg ORAL ANDA 18 sections
Cyproheptadine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 50268-201 TABLET 4 mg ORAL ANDA 21 sections
CYPROHEPTADINE HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 50742-190 TABLET 4 mg ORAL ANDA 21 sections
CYPROHEPTADINE HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 51407-272 TABLET 4 mg ORAL ANDA 21 sections
Cyproheptadine Hydrochloride Human Prescription Drug Label 1 52817-210 TABLET 4 mg ORAL ANDA 20 sections
Cyproheptadine Hydrochloride Human Prescription Drug Label 1 52817-415 TABLET 4 mg ORAL ANDA 20 sections
Cyproheptadine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 53808-0829 TABLET 4 mg ORAL ANDA 21 sections
CYPROHEPTADINE HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 53808-0950 TABLET 4 mg ORAL ANDA 19 sections
Cyproheptadine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 53808-1030 TABLET 4 mg ORAL ANDA 21 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 18 sections
cyproheptadine hydrochloride solution HUMAN PRESCRIPTION DRUG LABEL 1 58657-697 SOLUTION 2 mg ORAL ANDA 11 sections
cyproheptadine hydrochloride solution HUMAN PRESCRIPTION DRUG LABEL 1 58657-697 SOLUTION 2 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 62135-236 TABLET 4 mg ORAL ANDA 12 sections
CYPROHEPTADINE HUMAN PRESCRIPTION DRUG LABEL 1 62135-949 SYRUP 2 mg ORAL ANDA 11 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 17 sections
Cyproheptadine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 68151-1728 SYRUP 2 mg ORAL ANDA 17 sections