Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-06 15:16:49 UTC |
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Update Date | 2022-03-07 02:51:40 UTC |
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HMDB ID | HMDB0014578 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Cyproheptadine |
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Description | Cyproheptadine, also known as ciprovit or antergan, belongs to the class of organic compounds known as dibenzocycloheptenes. Dibenzocycloheptenes are compounds containing a dibenzocycloheptene moiety, which consists of two benzene rings connected by a cycloheptene ring. Cyproheptadine is a drug which is used 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. Cyproheptadine is a very strong basic compound (based on its pKa). In humans, cyproheptadine is involved in cyproheptadine h1-antihistamine action. It is a sedating antihistamine with antimuscarinic and calcium-channel blocking actions. Unlike other antihistamines, it is also a seratonin receptor antagonist, making it useful in conditions such as vascular headache and anorexia. The product resulting from the formal oxidative coupling of position 5 of 5H-dibenzocycloheptene with position 4 of 1-methylpiperidine resulting in the formation of a double bond between the two fragments. Cyproheptadine is a potentially toxic compound. It is used (particularly as the hydrochloride sesquihydrate) for the relief of allergic conditions including rhinitis, conjunctivitis due to inhalant allergens and foods, urticaria and angioedema, and in pruritic skin disorders. |
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Structure | CN1CCC(CC1)=C1C2=CC=CC=C2C=CC2=CC=CC=C12 InChI=1S/C21H21N/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 |
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Synonyms | Value | Source |
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1-Methyl-4-(5-dibenzo(a,e)cycloheptatrienylidene)piperidine | ChEBI | 1-Methyl-4-(5H-dibenzo(a,D)cycloheptenylidene)piperidine | ChEBI | 4-(5-Dibenzo(a,D)cyclohepten-5-ylidine)-1-methylpiperidine | ChEBI | 4-(5H-Dibenzo(a,D)cyclohepten-5-ylidene)-1-methylpiperidine | ChEBI | 4-Dibenzo[a,D]cyclohepten-5-ylidene-1-methyl-piperidine | ChEBI | 5-(1-Methylpiperidylidene-4)-5H-dibenzo(a,D)cyclopheptene | ChEBI | Ciproheptadina | ChEBI | Cyproheptadinum | ChEBI | Ciprovit | Kegg | Antergan | HMDB | Periactin | HMDB | Peritol | HMDB | Viternum | HMDB | Dihexazin | HMDB |
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Chemical Formula | C21H21N |
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Average Molecular Weight | 287.3981 |
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Monoisotopic Molecular Weight | 287.167399677 |
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IUPAC Name | 1-methyl-4-{tricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,9,11,13-heptaen-2-ylidene}piperidine |
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Traditional Name | periactin |
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CAS Registry Number | 129-03-3 |
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SMILES | CN1CCC(CC1)=C1C2=CC=CC=C2C=CC2=CC=CC=C12 |
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InChI Identifier | InChI=1S/C21H21N/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 |
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InChI Key | JJCFRYNCJDLXIK-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as dibenzocycloheptenes. Dibenzocycloheptenes are compounds containing a dibenzocycloheptene moiety, which consists of two benzene rings connected by a cycloheptene ring. |
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Kingdom | Organic compounds |
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Super Class | Benzenoids |
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Class | Dibenzocycloheptenes |
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Sub Class | Not Available |
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Direct Parent | Dibenzocycloheptenes |
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Alternative Parents | |
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Substituents | - Dibenzocycloheptene
- Piperidine
- Tertiary aliphatic amine
- Tertiary amine
- Azacycle
- Organoheterocyclic compound
- Organic nitrogen compound
- Organopnictogen compound
- Hydrocarbon derivative
- Organonitrogen compound
- Amine
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | |
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Role | |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | 215 - 217 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 0.014 g/L | Not Available | LogP | 4.7 | Not Available |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | | Show more...
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatized | Show more...
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Spectra |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - Cyproheptadine GC-MS (Non-derivatized) - 70eV, Positive | splash10-05g0-1090000000-7d19fca2a65a93c449d6 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Cyproheptadine GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | MS | Mass Spectrum (Electron Ionization) | splash10-00kr-2290000000-a17c27a9f171b058f2c3 | 2014-09-20 | Not Available | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental LC-MS/MS | LC-MS/MS Spectrum - Cyproheptadine LC-ESI-qTof , Positive-QTOF | splash10-000i-0290000000-964629904e89d79568d8 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Cyproheptadine , positive-QTOF | splash10-000i-0290000000-964629904e89d79568d8 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Cyproheptadine 35V, Positive-QTOF | splash10-000m-6790000000-4e9938638118593eb406 | 2021-09-20 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cyproheptadine 10V, Positive-QTOF | splash10-000i-1090000000-3117ec5d9639f751f7b7 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cyproheptadine 20V, Positive-QTOF | splash10-000i-3290000000-2935111fa6fa07111de6 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cyproheptadine 40V, Positive-QTOF | splash10-00r6-9370000000-df84a6a14decead8dedf | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cyproheptadine 10V, Negative-QTOF | splash10-000i-0090000000-78685e74ff4bff75d39b | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cyproheptadine 20V, Negative-QTOF | splash10-000i-0090000000-cb222eada7f0bf316df6 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cyproheptadine 40V, Negative-QTOF | splash10-022i-5190000000-4e162fb598e8db9d6e77 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cyproheptadine 10V, Positive-QTOF | splash10-000i-0090000000-107477c8d28ce3506c90 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cyproheptadine 20V, Positive-QTOF | splash10-000i-0090000000-c2a155a089dd265a5433 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cyproheptadine 40V, Positive-QTOF | splash10-05mo-4190000000-eaa52ca5faae687ab50f | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cyproheptadine 10V, Negative-QTOF | splash10-000i-0090000000-26c7f893d45bf33544e2 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cyproheptadine 20V, Negative-QTOF | splash10-000i-0090000000-2c051f1f630ec47ecb1c | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cyproheptadine 40V, Negative-QTOF | splash10-00lr-0090000000-012e0121acf874e7bd11 | 2021-09-24 | Wishart Lab | View Spectrum |
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Biological Properties |
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Cellular Locations | |
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Biospecimen Locations | |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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Blood | Expected but not Quantified | Not Quantified | Not Available | Not Available | Taking drug identified by DrugBank entry DB00434 | | details | Urine | Expected but not Quantified | Not Quantified | Not Available | Not Available | Taking drug identified by DrugBank entry DB00434 | | details |
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Abnormal Concentrations |
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| Not Available |
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Predicted Concentrations |
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Blood | 0.000 uM | Adult (>18 years old) | Both | Normal | Predicted based on drug qualities | Blood | 0.000 umol/mmol creatinine | Adult (>18 years old) | Both | Normal | Predicted based on drug qualities |
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Associated Disorders and Diseases |
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Disease References | None |
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | DB00434 |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | Not Available |
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KNApSAcK ID | Not Available |
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Chemspider ID | 2810 |
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KEGG Compound ID | C06935 |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Cyproheptadine |
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METLIN ID | Not Available |
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PubChem Compound | 2913 |
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PDB ID | Not Available |
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ChEBI ID | 4046 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | Not Available |
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Good Scents ID | Not Available |
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References |
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Synthesis Reference | Not Available |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - Tokunaga S, Takeda Y, Shinomiya K, Hirase M, Kamei C: Effects of some H1-antagonists on the sleep-wake cycle in sleep-disturbed rats. J Pharmacol Sci. 2007 Feb;103(2):201-6. Epub 2007 Feb 8. [PubMed:17287588 ]
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