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C6022

Sigma-Aldrich

Cyproheptadine hydrochloride sesquihydrate

≥98% (TLC), solid

Synonym(s):

Piperidine, 4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-methyl-, hydrochloride, hydrate (2:3)

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About This Item

Empirical Formula (Hill Notation):
C21H21N·HCl·1.5H2O
CAS Number:
41354-29-4
Molecular Weight:
350.88
EC Number:
213-535-1
UNSPSC Code:
12352200
PubChem Substance ID:
24278082
NACRES:
NA.77

assay

≥98% (TLC)

form

solid

color

white to slightly yellow

solubility

ethanol: soluble
methanol: soluble

originator

Merck & Co., Inc., Kenilworth, NJ, U.S.

SMILES string

Cl.CN1CCC(\CC1)=C2/c3ccccc3C=Cc4ccccc24

InChI

1S/2C21H21N.2ClH.3H2O/c2*1-22-14-12-18(13-15-22)21-19-8-4-2-6-16(19)10-11-17-7-3-5-9-20(17)21;;;;;/h2*2-11H,12-15H2,1H3;2*1H;3*1H2

InChI key

ZEAUHIZSRUAMQG-UHFFFAOYSA-N

Gene Information

human ... HRH1(3269) , HTR2A(3356) , HTR2B(3357) , HTR2C(3358)

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Application

Cyproheptadine hydrochloride sesquihydrate has been used in:
  • testing anti-inflammatory activity in serotonin receptor (5-HT) induced inflammation
  • the inhibition of 5-HT in in vivo and in vitro bioassays in crabs
  • the inhibition of 5-HT in embryo physiological experiments

inhibition of calcitonin gene related peptide (CGRP)

Biochem/physiol Actions

Cyproheptadine hydrochloride sesquihydrate is a serotonin receptor (5-HT2/5-HT1C) antagonist, H1 histamine receptor antagonist and an antipruritic. The inhibition of 5-HT by cyproheptadine improves cognitive function in schizophrenia disorder. Cyproheptadine is effective for treating functional gastrointestinal disorders (FGIDs). Food and Drug Administration (FDA) approved cyproheptadine, has antidepressant and antiplatelet functionality. It may be effective in treating thromboembolic disorders. Cyproheptadine inhibits lysine methyltransferase 7/9 (Set7/9) leading to a decrease in estrogen receptor (ERα) expression and growth arrest in breast cancer cells.

Features and Benefits

This compound was developed by Merck & Co., Inc., Kenilworth, NJ, U.S.. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

pictograms

Skull and crossbones
GHS06

signalword

Danger

Hazard Classifications

Acute Tox. 3 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Anti-inflammatory activity of bartogenic acid containing fraction of fruits of Barringtonia racemosa Roxb. in acute and chronic animal models of inflammation
Patil KR and Patil CR
Journal of traditional and complementary medicine, 7(1), 86-93 (2017)
Identification of cyproheptadine as an inhibitor of SET domain containing lysine methyltransferase 7/9 (Set7/9) that regulates estrogen-dependent transcription
Takemoto Y, et al.
Journal of Medicinal Chemistry, 59(8), 3650-3660 (2016)
E O Okoro
The Journal of pharmacy and pharmacology, 51(8), 953-957 (1999-09-30)
We have previously shown that elimination of buffer Ca2+ markedly reduced maximum 5-HT-induced contractions. We have now investigated the effect of L-type Ca2+-channel blockers and 5-HT2 receptor antagonists on 5-HT- and K+-induced contractions in rat aorta to explore the possibility
Effects of the 5HT antagonist cyproheptadine on neuropsychological function in chronic schizophrenia
Chaudhry IB, et al.
Schizophrenia Research, 53(1-2), 17-24 (2002)
Cyproheptadine: a potentially effective treatment for functional gastrointestinal disorders in children
Krasaelap A and Madani S
Pediatric Annals, 46(3), e120-e125 (2017)
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