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C3200000

Cyclobenzaprine hydrochloride

European Pharmacopoeia (EP) Reference Standard

Synonym(s):

5-(3-Dimethylaminopropylidene)dibenzo[a,e]cycloheptatriene hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C20H21N · HCl
CAS Number:
6202-23-9
Molecular Weight:
311.85
MDL number:
MFCD00079039
UNSPSC Code:
41116107
PubChem Substance ID:
329775025
NACRES:
NA.24

grade

pharmaceutical primary standard

API family

cyclobenzaprine

manufacturer/tradename

EDQM

application(s)

pharmaceutical (small molecule)

format

neat

SMILES string

Cl.CN(C)CC\C=C1\c2ccccc2C=Cc3ccccc13

InChI

1S/C20H21N.ClH/c1-21(2)15-7-12-20-18-10-5-3-8-16(18)13-14-17-9-4-6-11-19(17)20;/h3-6,8-14H,7,15H2,1-2H3;1H

InChI key

VXEAYBOGHINOKW-UHFFFAOYSA-N

Gene Information

human ... HTR2A(3356) , HTR2C(3358)

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General description

This product is provided as delivered and specified by the issuing Pharmacopoeia. All information provided in support of this product, including SDS and any product information leaflets have been developed and issued under the Authority of the Issuing Pharmacopoeia. For further information and support please go to the website of the issuing Pharmacopoeia.

Application

Cyclobenzaprine hydrochloride EP Reference standard, intended for use in laboratory tests only as specifically prescribed in the European Pharmacopoeia.

Biochem/physiol Actions

Skeletal muscle relaxant; reduces muscle spasm by depression of brainstem neurons; 5-HT2 serotonin receptor antagonist.

Packaging

The product is delivered as supplied by the issuing Pharmacopoeia. For the current unit quantity, please visit the EDQM reference substance catalogue.

Other Notes

Sales restrictions may apply.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301,H312 + H332

Hazard Classifications

Acute Tox. 3 Oral - Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation

Storage Class Code

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

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number

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Reinhard Reuss et al.
Pharmacology, 84(2), 91-92 (2009-07-11)
The muscle-relaxing 5-HT(2) receptor antagonist cyclobenzaprine is structurally closely related to amitriptyline. It is widely used to treat patients presenting with back pain and fibromyalgia. Very rarely cyclobenzaprine toxicity can result in extrapyramidal symptoms, but occurrence of torticollis has not
J Mestres et al.
Clinical pharmacology and therapeutics, 90(5), 662-665 (2011-10-07)
The link between cyclobenzaprine (Flexeril) administration and serotonin syndrome (SS) is subject to debate. Establishing such a connection is difficult because of the limited number of case reports available and the almost complete ignorance of its preclinical pharmacology. In this
S Mustafah Khwaja et al.
CJEM, 12(1), 39-44 (2010-01-19)
We compared pain severity and time to resumption of activities in patients with cervical strains treated with a nonsteroidal anti-inflammatory drug (NSAID), a centrally acting muscle relaxant or both. We performed a double-blinded, randomized controlled trial of adults with cervical
Stephen Landy et al.
Advances in therapy, 28(4), 295-303 (2011-03-23)
This post-hoc analysis examined time to recovery in patients with acute, painful musculoskeletal conditions following cyclobenzaprine extended release (CER; AMRIX(®), Cephalon, Inc., Frazer, PA, USA), cyclobenzaprine immediate release (CIR; Flexeril(®), Pliva, Pomona, NY, USA), or placebo administration. Data were pooled
Mona Darwish et al.
Expert opinion on drug metabolism & toxicology, 6(11), 1425-1436 (2010-10-05)
Cyclobenzaprine immediate-release (CIR) is a widely prescribed skeletal muscle relaxant with an established efficacy and safety profile in patients with muscle spasm associated with acute, painful conditions, although it is commonly associated with sedation. CIR is typically prescribed at a
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