| 词条 | Chloroethynylnorgestrel |
| 释义 |
| Verifiedfields = | Watchedfields = | verifiedrevid = | IUPAC_name = (1S,2R,10R,11S,14S,15S)-14-(2-chloroethynyl)-15-ethyl-14-hydroxytetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one | image = Chloroethynyl norgestrel.svg | width = | 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 = 2415-28-3 | CAS_supplemental = | ATC_prefix = | ATC_suffix = | PubChem = 22790422 | DrugBank_Ref = | DrugBank = | ChemSpiderID_Ref = | ChemSpiderID = 18503812 | C=21 | H=27 | Cl=1 | O=2 | molecular_weight = 346.89088 g/mol | smiles = CC[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(C#CCl)O)CCC4=CC(=O)CC[C@H]34 | StdInChI_Ref = | StdInChI = 1S/C21H27ClO2/c1-2-20-9-7-17-16-6-4-15(23)13-14(16)3-5-18(17)19(20)8-10-21(20,24)11-12-22/h13,16-19,24H,2-10H2,1H3/t16-,17+,18+,19-,20-,21+/m0/s1 | StdInChIKey_Ref = | StdInChIKey = MISOWVVRHHLGIK-ZUHHCLADSA-N | synonyms = Chloroethynyl norgestrel; WY-4355; 17α-Chloroethynyl-13β-ethylgon-4-en-17β-ol-3-one; 17α-Chloroethynyl-18-methylestr-4-en-17β-ol-3-one; 17α-Chloroethynyl-18-methyl-19-nortestosterone }}Chloroethynylnorgestrel (developmental code name WY-4355) is a steroidal progestin of the 19-nortestosterone group related to norgestrel that was investigated as an oral contraceptive in the 1970s but was never marketed.[1][2][3][4] In combination with mestranol, similarly to ethynerone and anagestone acetate (and certain other progestogens, including progesterone and several other 17α-hydroxyprogesterone derivatives), chloroethynylnorgestrel was found to produce striking mammary tumors in beagle dogs after administration at very high dosages (10- to 25-fold human clinical dosages) for prolonged periods of time.[1][3][4] This resulted in the discontinuation of its development, along with that of ethynerone and anagestone acetate, as well as the removal of several progestins, including chlormadinone acetate, medroxyprogesterone acetate, and megestrol acetate, from various markets as contraceptives (although medroxyprogesterone acetate has since been reintroduced).[1][5] Subsequent research revealed that the risk is species-dependent and unique to canines and that there is no similar risk for humans.[6] {{Clear}}References1. ^1 2 {{cite book |author=C.H. Lingeman |title=Carcinogenic Hormones |url=https://books.google.com/books?id=lOLnCAAAQBAJ&pg=PA149 |date=6 December 2012 |publisher=Springer Science & Business Media |isbn=978-3-642-81267-5 |pages=149–}} {{Progesterone receptor modulators}}{{genito-urinary-drug-stub}}{{steroid-stub}}2. ^{{cite journal |vauthors=Tavassoli FA, Casey HW, Norris HJ |title=The morphologic effects of synthetic reproductive steroids on the mammary gland of rhesus monkeys. Mestranol, ethynerone, mestranol-ethynerone, chloroethynyl norgestrel-mestranol, and anagestone acetate-mestranol combinations |journal=Am. J. Pathol. |volume=131 |issue=2 |pages=213–34 |year=1988 |pmid=3358452 |pmc=1880606 |doi= |url=}} 3. ^1 {{cite journal |last1=Geil |first1=R. G. |last2=Lamar |first2=J. K. |title=FDA studies of estrogen, progestogens, and estrogen/progestogen combinations in the dog and monkey |journal=Journal of Toxicology and Environmental Health |volume=3 |issue=1-2 |year=2009 |pages=179–193 |issn=0098-4108 |doi=10.1080/15287397709529557}} 4. ^1 {{cite journal |last1=Casey |first1=H. W. |last2=Giles |first2=R. C. |last3=Kwapien |first3=R. P. |title=Mammary Neoplasia in Animals: Pathologic Aspects and the Effects of Contraceptive Steroids |year=1979 |pages=129–160 |doi=10.1007/978-3-642-81267-5_4}} 5. ^{{cite book |author1=Christian Streffer |author2=H. Bolt |author3=D. Follesdal |author4=P. Hall |author5=J.G. Hengstler |author6=P. Jacob |author7=D Oughton |author8=K. Prieß |author9=E. Rehbinder |author10=E. Swaton |title=Low Dose Exposures in the Environment: Dose-Effect Relations and Risk Evaluation |url=https://books.google.com/books?id=eiL4CAAAQBAJ&pg=PA135 |date=11 November 2013 |publisher=Springer Science & Business Media |isbn=978-3-662-08422-9 |pages=135–}} 6. ^{{cite book |author1=Benno Clemens Runnebaum |author2=Thomas Rabe |author3=Ludwig Kiesel |title=Female Contraception: Update and Trends |url=https://books.google.com/books?id=LtT6CAAAQBAJ&pg=PA134 |date=6 December 2012 |publisher=Springer Science & Business Media |isbn=978-3-642-73790-9 |pages=134–}} 4 : Abandoned drugs|Estranes|Organochlorides|Progestogens |
| 随便看 |
|
开放百科全书收录14589846条英语、德语、日语等多语种百科知识，基本涵盖了大多数领域的百科知识，是一部内容自由、开放的电子版国际百科全书。