| 词条 | Triparanol |
| 释义 |
| Verifiedfields = | Watchedfields = | verifiedrevid = | IUPAC_name = 2-(4-Chlorophenyl)-1-[4-[2-(diethylamino)ethoxy]phenyl]-1-(4-methylphenyl)ethanol | image = Triparanol.svg | width = 250 | tradename = | pregnancy_AU = | pregnancy_US = | pregnancy_category = | legal_AU = | legal_CA = | legal_UK = | legal_US = | legal_status = | routes_of_administration = | bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion = | CAS_number_Ref = | CAS_number = 78-41-1 | CAS_supplemental = | ATCvet = | ATC_prefix = None | ATC_suffix = | ATC_supplemental = | PubChem = 6536 | IUPHAR_ligand = | DrugBank_Ref = | DrugBank = | ChemSpiderID_Ref = | ChemSpiderID = 6288 | UNII = 63S8C3RXGS | KEGG = | ChEBI = 135714 | ChEMBL = | C=27 | H=32 | Cl=1 | N=1 | O=2 | molecular_weight = 438.00148 g/mol | smiles = CCN(CC)CCOC1=CC=C(C=C1)C(CC2=CC=C(C=C2)Cl)(C3=CC=C(C=C3)C)O | StdInChI_Ref = | StdInChI = 1S/C27H32ClNO2/c1-4-29(5-2)18-19-31-26-16-12-24(13-17-26)27(30,23-10-6-21(3)7-11-23)20-22-8-14-25(28)15-9-22/h6-17,30H,4-5,18-20H2,1-3H3 | StdInChIKey_Ref = | StdInChIKey = SYHDSBBKRLVLFF-UHFFFAOYSA-N | synonyms = Metasqualene }}Triparanol (INN, BAN) (brand and developmental code names MER/29, as well as many other brand names), patented in 1959 and introduced in the United States in 1960,[1][1] was the first synthetic cholesterol-lowering drug.[2][3] It was withdrawn in 1962 due to severe adverse effects such as nausea and vomiting, vision loss due to irreversible cataracts, alopecia, skin disorders (e.g., dryness, itching, peeling, and "fish-scale" texture), and accelerated atherosclerosis and is now considered to be obsolete.[1][3] The drug acts by inhibiting 24-dehydrocholesterol reductase, which catalyzes the final step of cholesterol biosynthesis, the conversion of desmosterol into cholesterol.[4] This results in tissue accumulation of desmosterol, which in turn is responsible for the side effects of triparanol.[3] Unlike statins, triparanol does not inhibit HMG-CoA reductase, the rate-limiting enzyme in cholesterol biosynthesis,[3] and in contrast to triparanol, statins can significantly lower cholesterol levels without resulting in accumulation of intermediates like desmosterol.[3] The developmental code name of triparanol, MER/29, became so well known that it became the registered trade name of the drug.[5] Estrogen is known to lower cholesterol levels, but produces side effects like gynecomastia and decreased libido in men.[6] It was hoped that a drug could be developed that lacked overt estrogenic effects but still lowered cholesterol levels.[6] Triparanol is a triphenylethanol and was derived from chlorotrianisene (TACE), a nonsteroidal triphenylethylene estrogen,[6][7] and the nonsteroidal triphenylethanol antiestrogen ethamoxytriphetol (MER-25) is a derivative of triparanol.[8] The selective estrogen receptor modulator clomifene is also structurally related to triparanol.[7][9] The developers of triparanol jokingly referred to it as a "non-estrogenic estrogen".[6]See also
References1. ^{{cite book|author1=Dennis E. Vance|author2=Jean E. Vance|title=Biochemistry of Lipids, Lipoproteins, and Membranes|url=https://books.google.com/books?id=MQp2AB9QnoMC&pg=PA172|year=2002|publisher=Elsevier|isbn=978-0-444-51138-6|pages=172–174}} {{Lipid modifying agents}}{{cardiovascular-drug-stub}}2. ^{{cite book|author=J. Elks|title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA1252|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=1252–}} 3. ^1 2 3 4 {{cite book|author=Enrique Ravina|title=The Evolution of Drug Discovery: From Traditional Medicines to Modern Drugs|url=https://books.google.com/books?id=iDNy0XxGqT8C&pg=PA178|date=11 January 2011|publisher=John Wiley & Sons|isbn=978-3-527-32669-3|pages=178–}} 4. ^{{cite book|author1=Carl A. Burtis|author2=Edward R. Ashwood|author3=David E. Bruns|title=Tietz Textbook of Clinical Chemistry and Molecular Diagnostics|url=https://books.google.com/books?id=BBLRUI4aHhkC&pg=PA733|date=14 October 2012|publisher=Elsevier Health Sciences|isbn=1-4557-5942-2|pages=733–}} 5. ^{{cite journal|last1=Miller|first1=Lloyd C.|title=Doctors, Drugs, and Names|journal=JAMA|volume=177|issue=1|year=1961|pages=27|issn=0098-7484|doi=10.1001/jama.1961.73040270014004b|quote=Recently, another laboratory code number, MER29, became so well known that it was adopted as the registered trademark for the anticholesterolemic drug concerned (triparanol).}} 6. ^1 2 3 4 5 {{cite book|author=Jie Jack Li|title=Triumph of the Heart: The Story of Statins|url=https://books.google.com/books?id=-GPl1PA5EgMC&pg=PA33|date=3 April 2009|publisher=Oxford University Press, USA|isbn=978-0-19-532357-3|pages=33–}} 7. ^1 {{cite book|author1=W. Morton Grant|author2=Joel S. Schuman|title=TOXICOLOGY OF THE EYE: Effects on the Eyes and Visual System from Chemicals, Drugs, Metals and Minerals, Plants, Toxins and Venoms; also Systemic Side Effects from Eye Medications (4th Ed.)|url=https://books.google.com/books?id=mDLYCQAAQBAJ&pg=PA384|date=1 January 1993|publisher=Charles C Thomas Publisher|isbn=978-0-398-08215-4|pages=384–}} 8. ^{{cite book|author=Andrea Manni|title=Endocrinology of Breast Cancer|url=https://books.google.com/books?id=7DSYBwAAQBAJ&pg=PA286|date=15 January 1999|publisher=Springer Science & Business Media|isbn=978-1-59259-699-7|pages=286–}} 9. ^{{cite book|first=Jeffrey K. |last=Aronson |authorlink=Jeffrey Aronson |title=Meyler's Side Effects of Endocrine and Metabolic Drugs|url=https://books.google.com/books?id=BWMeSwVwfTkC&pg=PA163|date=21 February 2009|publisher=Elsevier|isbn=978-0-08-093292-7|pages=163–}} 7 : 24-Dehydrocholesterol reductase inhibitors|Alcohols|Amines|Hypolipidemic agents|Organochlorides|Phenol ethers|Withdrawn drugs |
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