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C6022

Sigma-Aldrich

Cyproheptadine hydrochloride sesquihydrate

≥98% (TLC), solid

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Synonym(s):
Piperidine, 4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-methyl-, hydrochloride, hydrate (2:3)
Empirical Formula (Hill Notation):
C21H21N·HCl·1.5H2O
CAS Number:
41354-29-4
Molecular Weight:
350.88
EC Number:
213-535-1
PubChem Substance ID:
24278082

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

Signal Word

Danger

Hazard Statements

H301 - H315 - H319 - H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

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

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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The analgesic agent tapentadol inhibits calcitonin gene-related peptide release from isolated rat brainstem via a serotonergic mechanism
Greco MC, et al.
Life Sciences, 145, 161-165 (2016)
Observations on the use of cyproheptadine hydrochloride as an antipruritic agent in allergic cats.
Scott DW, et al.
The Canadian Veterinary Journal. La Revue Veterinaire Canadienne, 39(10), 634-634 (1998)
S Kimura et al.
Immunological investigations, 27(6), 379-393 (1998-12-09)
For the immunopharmacological characterization of murine passive anaphylactic shock, the effects of antihistaminics and/or anti-platelet-activating factor (anti-PAF) agents were studied on the shock mediated by allogeneic monoclonal IgE and IgG1 antibodies and hyperimmune serum. IgE antibody-mediated shock was strongly suppressed
The antidepressant 5-HT2A receptor antagonists pizotifen and cyproheptadine inhibit serotonin-enhanced platelet function
Lin OA, et al.
PLoS ONE, 9(1), e87026-e87026 (2014)
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
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