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

Stem definition	Drug id	CAS RN
histamine-H1 receptor antagonists, tricyclic compounds	765	129-03-3

Description:

Molecule	Description
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:

Dose	Unit	Route
12	mg	O

ADMET properties:

Property	Value	Reference
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

Approvals:

Date	Agency	Company	Orphan
Oct. 17, 1961	FDA

FDA Adverse Event Reporting System (Female)

MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients 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 term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients 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:

Source	Code	Description
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)

Disease	Relation	SNOMED_ID	DOID
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 level	Dissociation constant	Type (acidic/basic)
pKa1	8.8	Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Mechanism action	Bioact source	MoA source
Histamine H1 receptor	GPCR	P35367	HRH1_HUMAN	ANTAGONIST	Ki	10.22		WOMBAT-PK	CHEMBL
5-hydroxytryptamine receptor 1D	GPCR	P28221	5HT1D_HUMAN		Ki	5.89		PDSP
Alpha-2A adrenergic receptor	GPCR	P08913	ADA2A_HUMAN		Ki	6.97		DRUG MATRIX
Potassium voltage-gated channel subfamily H member 2	Ion channel	Q12809	KCNH2_HUMAN		Ki	4.85		DRUG MATRIX
Alpha-2B adrenergic receptor	GPCR	P18089	ADA2B_HUMAN		Ki	7.77		DRUG MATRIX
Histamine H2 receptor	GPCR	P25021	HRH2_HUMAN		Ki	6.71		DRUG MATRIX
Muscarinic acetylcholine receptor M4	GPCR	P08173	ACM4_HUMAN		Ki	8.66		DRUG MATRIX
Muscarinic acetylcholine receptor M5	GPCR	P08912	ACM5_HUMAN		Ki	8.56		DRUG MATRIX
Alpha-2C adrenergic receptor	GPCR	P18825	ADA2C_HUMAN		Ki	6.73		DRUG MATRIX
Sodium-dependent noradrenaline transporter	Transporter	P23975	SC6A2_HUMAN		Ki	6.54		CHEMBL
Sodium channel alpha subunits; brain (Types I, II, III)	Ion channel	P35498 Q99250 Q9NY46	SCN1A_HUMAN SCN2A_HUMAN SCN3A_HUMAN		IC50	6		CHEMBL
Sodium-dependent serotonin transporter	Transporter	P31645	SC6A4_HUMAN		Ki	5.39		CHEMBL
5-hydroxytryptamine receptor 2C	GPCR	P28335	5HT2C_HUMAN		Ki	8.65		WOMBAT-PK
5-hydroxytryptamine receptor 2B	GPCR	P41595	5HT2B_HUMAN		Ki	8.81		WOMBAT-PK
5-hydroxytryptamine receptor 2A	GPCR	P28223	5HT2A_HUMAN		Ki	8.42		WOMBAT-PK
Calmodulin	Cytosolic other	P0DP23 P0DP24 P0DP25	CALM1_HUMAN CALM2_HUMAN CALM3_HUMAN					WOMBAT-PK
Alpha-1B adrenergic receptor	GPCR	P35368	ADA1B_HUMAN		Ki	7.60		WOMBAT-PK
Muscarinic acetylcholine receptor M3	GPCR	P20309	ACM3_HUMAN		Ki	8		WOMBAT-PK
Muscarinic acetylcholine receptor M2	GPCR	P08172	ACM2_HUMAN		Ki	8		WOMBAT-PK
Muscarinic acetylcholine receptor M1	GPCR	P11229	ACM1_HUMAN		Ki	8		WOMBAT-PK
Histamine H4 receptor	GPCR	Q9H3N8	HRH4_HUMAN		Ki	8.19		WOMBAT-PK
D(3) dopamine receptor	GPCR	P35462	DRD3_HUMAN		Ki	8.10		WOMBAT-PK
Alpha-1A adrenergic receptor	GPCR	P35348	ADA1A_HUMAN		Ki	7.40		WOMBAT-PK
5-hydroxytryptamine receptor 1A	GPCR	P08908	5HT1A_HUMAN		Ki	7.23		WOMBAT-PK
Multidrug resistance protein 1	Transporter	P08183	MDR1_HUMAN					WOMBAT-PK
Alpha-1D adrenergic receptor	GPCR	P25100	ADA1D_HUMAN		Ki	6.90		WOMBAT-PK
5-hydroxytryptamine receptor 7	GPCR	P34969	5HT7R_HUMAN		Ki	6.90		WOMBAT-PK
5-hydroxytryptamine receptor 6	GPCR	P50406	5HT6R_HUMAN		Ki	6.80		WOMBAT-PK
D(2) dopamine receptor	GPCR	P14416	DRD2_HUMAN		Ki	6.95		WOMBAT-PK
D(1A) dopamine receptor	GPCR	P21728	DRD1_HUMAN		Ki	6.93		WOMBAT-PK
Histone-lysine N-methyltransferase SETD7	Unclassified	Q8WTS6	SETD7_HUMAN		IC50	4.70		CHEMBL
Alpha-1B adrenergic receptor	GPCR		ADA1B_RAT		Ki	7.36		DRUG MATRIX
5-hydroxytryptamine receptor 1B	GPCR		5HT1B_RAT		Ki	5.90		DRUG MATRIX
Serotonin 2 (5-HT2) receptor	GPCR		5HT2A_RAT 5HT2B_RAT 5HT2C_RAT		IC50	8.51		CHEMBL
Dopamine receptor	GPCR		DRD1_RAT DRD2_RAT DRD3_RAT DRD4_RAT DRD5_RAT		Ki	7.20		CHEMBL
Sodium-dependent noradrenaline transporter	Transporter		SC6A2_MOUSE		Ki	6.54		CHEMBL
D(2) dopamine receptor	GPCR		DRD2_RAT		IC50	6.85		CHEMBL
Histamine H1 receptor	GPCR		HRH1_CAVPO		Kd	9		CHEMBL
5-hydroxytryptamine receptor 2C	GPCR		5HT2C_MOUSE		Ki	7.96		CHEMBL
5-hydroxytryptamine receptor 7	GPCR		5HT7R_RAT		Ki	7.30		CHEMBL
Muscarinic acetylcholine receptor	GPCR		ACM1_RAT ACM2_RAT ACM3_RAT ACM4_RAT ACM5_RAT		Ki	8.40		CHEMBL
D(2) dopamine receptor	GPCR		DRD2_MOUSE		Ki	6.95		CHEMBL
Sodium-dependent serotonin transporter	Transporter		SC6A4_MOUSE		Ki	5.39		CHEMBL
5-hydroxytryptamine receptor 2A	GPCR		5HT2A_RAT		Ki	8.80		CHEMBL
5-hydroxytryptamine receptor 1A	GPCR		5HT1A_RAT		IC50	6.91		CHEMBL
Alpha-1A adrenergic receptor	GPCR		ADA1A_RAT		IC50	6.62		CHEMBL
5-hydroxytryptamine receptor 6	GPCR		5HT6R_RAT	ANTAGONIST	Ki	6.90		IUPHAR

External reference:

ID	Source
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:

Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
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