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Cyproheptadine Hydrochloride

HCID 13770
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
41354-29-4
Standard SMILES
CN1CCC(=C2c3ccccc3C=Cc3ccccc32)CC1.Cl
InChIKey
ZPMVNZLARAEGHB-UHFFFAOYSA-N
Molecular formula
C21H22ClN
Average molar mass
323.9 g/mol
Monoisotopic mass
323.1440774

Overview

Cyproheptadine hydrochloride (anhydrous) is the hydrochloride salt of cyproheptadine. Note that the drug named cyproheptadine hydrochloride generally refers to cyproheptadine hydrochloride sesquihydrate. It contains a cyproheptadine.

Names & identifiers

Preferred name
Cyproheptadine Hydrochloride
IUPAC
1-methyl-4-(2-tricyclo[9.4.0.03,8]pentadeca-1(15),3,5,7,9,11,13-heptaenylidene)piperidine;hydrochloride
English name
Cyproheptadine hydrochloride sesquihydrate
Molecular formula
C21H24ClNO
Molecular weight
341.88

Names & synonyms

cyproheptadine hydrochloride969-33-5Cyproheptadine HclPeritolCyproheptadine hydrochloride anhydrousPeriactineNSC-169911Cyproheptadine Hydrochloride (anhydrous)0S9323MCT0NSC-759282DTXSID5042586CHEBI:59695
Show more names
CYPROHEPTADINE HYDROCHLORIDE HYDRATECYPROHEPTADINE HCI4-(5H-Dibenzo[a,d][7]annulen-5-ylidene)-1-methylpiperidine Hydrochloride SesquihydrateORIDE SESQUIHYDRATECYPROHEPTADINE HYDROCHLCyproheptadineHclUspGradeCyproptadine HydrochlorideCyproheptadine HCl hydrateHydrochloride sesquihydrate
Cyproheptadine hydroclorideNSC169911CHEBI:650917RefChem:57574DTXCID3022586213-535-1NJ82J0F8QCPeriactin hydrochloride

Database identifiers

CAS
41354-29-4、969-33-5

Properties

Computed structural properties

Topological polar surface area
3.2 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
1
Rotatable bonds
0
Heavy atoms
23
Formal charge
0
Complexity
423

Experimental & physicochemical properties

Human Drugs · 2 items

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Collision Cross Section171.7 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Physicochemical properties

Melting point
165 °C · 165 °C (dec.)(lit.)
storage temp.
Inert atmosphere,Room Temperature
solubility
ethanol: soluble
form
solid
color
white to slightly yellow
λmax
285 nm · 285nm(0.05mol/L H2SO4)(lit.)
Merck
14 · 14,2773
InChI
InChI=1S/C21H21N.ClH.H2O/c1-22-14-12-18(13-15-22)21-19-8-4-2-6-16(19)10-11-17-7-3-5-9-20(17)21;;/h2-11H,12-15H2,1H3;1H;1H2
InChIKey
PFQPCBUPUOPHGM-UHFFFAOYSA-N
SMILES
CN1CCC(=C2C3C=CC=CC=3C=CC3=CC=CC=C23)CC1.Cl.O

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 5 items

This chemical does not meet GHS hazard criteria for 1% (1 of 100) of reports.

Danger

H301 (46%): Toxic if swallowed [Danger Acute toxicity, oral]

P203, P261, P264, P264+P265, P270, P271, P280, P301+P316, P301+P317, P302+P352, P304+P340, P305+P351+P338, P318, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 100 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Other Safety InformationIMAP assessments - Piperidine, 4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-methyl-, hydrochloride: Environment tier I assessment
Hazard Classes and CategoriesAcute Tox. 3 (46%)

Toxicology

Treatment · 1 item

If vomiting has not occurred spontaneously the patient should be induced to vomit with syrup of ipecac. If the patient is unable to vomit, perform gastric lavage followed by activated charcoal. Isotonic or 1/2 isotonic saline is the lavage of choice. Precautions against aspiration must be taken especially in infants and children. When life threatening CNS signs and symptoms are present, intravenous physostigmine salicylate may be considered. Dosage and frequency of administration are dependent on age, clinical response, and recurrence after response. (See package circulars for physostigmine products.) Saline cathartics, as milk of magnesia, by osmosis draw water into the bowel and, therefore, are valuable for their action in rapid dilution of bowel content. Stimulants should not be used. Vasopressors may be used to treat hypotension. (L1712)

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 1 item

Hepatic (cytochrome P-450 system) and some renal. Route of Elimination: After a single 4 mg oral dose of14C-labelled cyproheptadine HCl in normal subjects, given as tablets 2% to 20% of the radioactivity was excreted in the stools. At least 40% of the administered radioactivity was excreted in the urine.

MeSH Pharmacological Classification · 5 items

Agents, usually topical, that relieve itching (pruritus).

Drugs used for their effects on the gastrointestinal system, as to control gastric acidity, regulate gastrointestinal motility and water flow, and improve digestion.

Drugs that selectively bind to but do not activate histamine H1 receptors, thereby blocking the actions of endogenous histamine. Included here are the classical antihistaminics that antagonize or prevent the action of histamine mainly in immediate hypersensitivity. They act in the bronchi, capillaries, and some other smooth muscles, and are used to prevent or allay motion sickness, seasonal rhinitis, and allergic dermatitis and to induce somnolence. The effects of blocking central nervous system H1 receptors are not as well understood.

Drugs that bind to but do not activate serotonin receptors, thereby blocking the actions of serotonin or SEROTONIN RECEPTOR AGONISTS.

Agents that are used to treat allergic reactions. Most of these drugs act by preventing the release of inflammatory mediators or inhibiting the actions of released mediators on their target cells. (From AMA Drug Evaluations Annual, 1994, p475)

Uses & manufacturing

Uses · 1 item

Used as an antihistaminic/anticholinergic and antiserotonergic agent. For treatment of perennial and seasonal allergic rhinitis, vasomotor rhinitis, allergic conjunctivitis due to inhalant allergens and foods, mild uncomplicated allergic skin manifestations of urticaria and angioedema, amelioration of allergic reactions to blood or plasma, cold urticaria, dermatographism, and as therapy for anaphylactic reactions adjunctive to epinephrine.

Applications · 6 items

Related reactions

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
PubChem CID
13770
DTXSID
DTXSID5042586
ChEMBL
CHEMBL1716
ChEBI
CHEBI:59695
UNII
0S9323MCT0
EC Number
213-535-1
CAS DataBase Reference
41354 · 41354-29-4(CAS DataBase Reference)
FDA UNII
82 J0F8QC · NJ82J0F8QC
NCI Drug Dictionary
cyproheptadine hydrochloride
UNSPSC Code
41116107 · 41116107
NACRES
77 · NA.77
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
302 · H302-H315-H319-H335
Precautionary statements
261 · P261-P264-P270-P301+P312-P302+P352-P305+P351+P338
target organs
Respiratory system
PPE
95 · dust mask type N95 (US), Eyeshields, Faceshields, Gloves
Hazard Codes
Xn
Risk Statements
22 · 22-36/37/38
Safety Statements
26 · 26-36
RIDADR
2811 · UN 2811 6.1/PG 3
WGK Germany
3 · 3
RTECS
7050000 · TM7050000
HazardClass
6.1 · 6.1
PackingGroup
III
HS Code
29333990 · 29333990
Storage Class
6.1 C · 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
Hazard Classifications
3 OralEye · Acute Tox. 3 OralEye Irrit. 2Skin Irrit. 2STOT SE 3
Toxicity
50 orally · LD50 orally in mice: 74.2 mg/kg (Loux)
Exposure RoutesWell absorbed after oral administration.
Toxicity Summary · 1 item

Cyproheptadine competes with free histamine for binding at HA-receptor sites. This antagonizes the effects of histamine on HA-receptors, leading to a reduction of the negative symptoms brought on by histamine HA-receptor binding. Cyproheptadine also competes with serotonin at receptor sites in smooth muscle in the intestines and other locations. Antagonism of serotonin on the appetite center of the hypothalamus may account for Cyproheptadine's ability to stimulate appetite.

Signs and SymptomsDrowsiness, epigastric distress (dysphagia), nausea, vomiting, (it is noted that these side effects are much more common in people with neuromuscular disorders). [Wikipedia]
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Drug Induced Liver Injury · 6 items

Drug Induced Liver Injury Rank (DILIrank 2.0)

Cyproheptadine hydrochloride

vLess-DILI-concern

7

Adverse reactions

DOI:10.1016/j.drudis.2016.02.015

Safety data

PPE
dust mask type N95 (US), Eyeshields, Faceshields, Gloves
wgk
3
rtecs
TM7050000
ridadr
UN 2811 6.1/PG 3
hs_code
29333990
Toxicity
LD50 orally in mice: 74.2 mg/kg (Loux)
risk_code
22-36/37/38
Signal word
Warning
Symbol(GHS)
GHS07
hazard_code
Xn
safety_code
26-36
hazard_class
6.1
Storage Class
6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
packing_group
III
target organs
Respiratory system
Hazard statements
H302-H315-H319-H335
Hazard Classifications
Acute Tox. 3 OralEye Irrit. 2Skin Irrit. 2STOT SE 3
Precautionary statements
P261-P264-P270-P301+P312-P302+P352-P305+P351+P338

UsesAnticoagulant, anti-allergic drugs. It can be used for urticaria, eczema, and allergic contact dermatitis, skin itching and other allergic reactions. It can also be used for Cushing's diseases and acromegaly.

UsesH1-antihistamine, antipruritic

UsesStructural studies of an antihistimine

UsesCyproheptadine hydrochloride sesquihydrate has been used in:testing anti-inflammatory activity in serotonin receptor (5-HT) induced inflammationthe inhibition of 5-HT in in vivo and in vitro bioassays in crabsthe inhibition of 5-HT in embryo physiological experimentsinhibition of calcitonin gene related peptide (CGRP)

UsesCyproheptadine is a first-generation antihistamine with additional anticholinergic, antiserotonergic, and local anesthetic properties. Cyproheptadine is a 5-HT2/5-HT1C serotonin receptor antagonist; H 1 histamine receptor antagonist; antipruritic.

General DescriptionCyproheptadine hydrochloride sesquihydrate is an antihistamine and is an antagonist of serotonin and histamine. It induced preventive effect against the development of pergolide-induced valvulopathy in a rat model.

Upstream & downstream products

Upstream raw materials

Phenylacetic acid

Suppliers100 total

北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
合肥翰刚医药科技有限公司+8618062405514 · [email protected]
Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]
Hebei Yanxi Chemical Co., Ltd.+86-17531190177 · [email protected]
Jai Radhe Sales+(91)-(79)-26431096/65255722 · [email protected]
LGM Pharma1-(800)-881-8210 · [email protected]
武汉易泰科技有限公司上海分公司18930552037 · [email protected]
大连美仑生物技术有限公司0411-62910999 13889544652 · [email protected]
广州市亿邦医药科技有限公司+86 (20) 28996708,29078958,28139708,29076128,28133708,28139728,28139738,28133718,021-31663278,021-31663578,021-60538387
上海瀚鸿科技股份有限公司021-54306202 13764082696 · [email protected]
广州济成进出口贸易有限公司13682223272 · [email protected]
MedChemexpress LLC021-58955995 · [email protected]
上海瀚香生物科技有限公司177-54423994 17754423994 · [email protected]
斯百全化学(上海)有限公司021-021-021-67601398-809-809-809 15221380277 · [email protected]
上海源叶生物科技有限公司18916372613 · [email protected]
TCI AMERICA800-4238616 · [email protected]
TOKYO CHEMICAL INDUSTRY CO., LTD.03-36680489 · [email protected]
TCI Europe320-37350700 · [email protected]
广州爱纯医药科技有限公司020-39119399 18927568969 · [email protected]
深圳市石金谷科技有限公司(0086)755-61930359 (0086)18038192047 · [email protected]
上海将来实业股份有限公司021-61552785 · [email protected]
安徽科迪达化工有限公司0554-2106669 · [email protected]
成都零六生物科技有限公司400-1166-196 13458535857 · [email protected]
上海创赛科技有限公司400-6087598 15021221957 · [email protected]
上海御略医药科技有限公司021-60345187 13671753212 · [email protected]
杭州杰恒化工有限公司0571-87396432 · [email protected]
上海永叶生物科技有限公司86-021-61559134 15921386130 · [email protected]
上海孚一生物科技有限公司+86 (21) 61124340
凯试(上海)科技有限公司021-50135380 · [email protected]
湖北巨胜科技有限公司027-59599241 18871490274 · [email protected]
池州凯隆进出口贸易有限公司[email protected]
Sigma-Aldrich西格玛奥德里奇(上海)贸易有限公司021-61415566 800-8193336 · [email protected]
TargetMol中国(陶术生物)021-021-33632979 15002134094 · [email protected]
Alfa Chemistry1-516-6625404 · [email protected]
上海昕凯医药科技有限公司21-619849051-1 18521059765 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354; +1-00000000000 · [email protected]
九鼎化学(上海)科技有限公司4009209199 · [email protected]
Henan Alfa Chemical Co., Ltd+8618339805032 · [email protected]
西安美川生物科技有限公司029-89275612 +8618991951683 · [email protected]
Qiuxian Baitai New Material Co., LTD+86-19932103556 · [email protected]
康幸生物科技(上海)有限公司021-61556450 15800904410
上海思言生物科技有限公司021-50908862,442785678,326799392 18721037013 · [email protected]
上海西陇生化科技有限公司021-52907766-8042
上海前衍生物科技有限公司02781293128 · [email protected]
南京博米尔生物科技有限公司025-83453382-8005 · [email protected]
南京罗迈美生物科技有限公司[email protected]
上海澄绍生物科技有限公司021-61847300 13341622919 · [email protected]
上海新平精细化学品有限公司18221735425 · [email protected]
Additional notes · 1 item

DefinitionChEBI: The sesquihydrate of cyproheptadine hydrochloride. Note that the drug named cyproheptadine hydrochloride generally refers to cyproheptadine hydrochloride sesquihydrate. A sedating antihistamine with antimuscarinic and calcium-channel blocking actions, it i used for the relief of allergic conditions including rhinitis, conjunctivitis due to inhalant allergens and foods, urticaria and angioedema, and in pruritic skin disorders. Unlike other antihistamines, it is also a seratonin receptor antagonist, making it useful in conditions such as vascular headache and anorexia.