Levonorgestrel is a hormonal medication which is used in a number of birth control methods. It is combined with an estrogen to make combination birth control pills. As an emergency birth control, sold under the brand names Plan B One-Step and Julie, among others, it is useful within 72 hours of unprotected sex. The more time that has passed since sex, the less effective the medication becomes, and it does not work after pregnancy (implantation) has occurred. Levonorgestrel works by preventing ovulation or fertilization from occurring. It decreases the chances of pregnancy by 57–93%. In an intrauterine device (IUD), such as Mirena among others, it is effective for the long-term prevention of pregnancy. A levonorgestrel-releasing implant is also available in some countries.
Common side effects include nausea, breast tenderness, headaches, and increased, decreased, or irregular menstrual bleeding. When used as an emergency contraceptive, if pregnancy occurs, there is no evidence that its use harms the fetus. It is safe to use during breastfeeding. Birth control that contains levonorgestrel will not change the risk of sexually transmitted infections. It is a progestin and has effects similar to those of the hormone progesterone. It works primarily by preventing ovulation and closing off the cervix to prevent the passage of sperm.
Levonorgestrel was patented in 1960 and introduced for medical use together with ethinylestradiol in 1970. It is on the World Health Organization's List of Essential Medicines. It is available as a generic medication. In the United States, levonorgestrel-containing emergency contraceptives are available over the counter (OTC) for all ages. In 2020, it was the 323rd most commonly prescribed medication in the United States, with more than 800 thousand prescriptions. |
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InChI=1S/C43H53NO14/c1- 22- 26(55- 37(51) 32(48) 30(24- 15- 11- 9- 12- 16- 24) 44- 38(52) 58- 39(3,4) 5) 20- 43(53) 35(56- 36(50) 25- 17- 13- 10- 14- 18- 25) 33- 41(8,34(49) 31(47) 29(22) 40(43,6) 7) 27(46) 19- 28- 42(33,21- 54- 28) 57- 23(2) 45/h9- 18,26- 28,30- 33,35,46- 48,53H,19- 21H2,1- 8H3,(H,44,52) /t26- ,27- ,28+,30- ,31+,32+,33- ,35- ,41+,42- ,43+/m0/s1 |
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antimalarial
A drug used in the treatment of malaria. Antimalarials are usually classified on the basis of their action against Plasmodia at different stages in their life cycle in the human.
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antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
photosensitizing agent
A chemical compound that can be excited by light of a specific wavelength and subsequently transfer energy to a chosen reactant. This is commonly molecular oxygen within a cancer tissue, which is converted to (highly rective) singlet state oxygen. This rapidly reacts with any nearby biomolecules, ultimately killing the cancer cells.
antimalarial
A drug used in the treatment of malaria. Antimalarials are usually classified on the basis of their action against Plasmodia at different stages in their life cycle in the human.
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View more via ChEBI Ontology
4- (acetyloxy)- 13α- ({(2R,3S)- 3- [(tert- butoxycarbonyl)amino]- 2- hydroxy- 3- phenylpropanoyl}oxy)- 1,7β,10β- trihydroxy- 9- oxo- 5β,20- epoxytax- 11- en- 2α- yl benzoate
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Docetaxel
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KEGG COMPOUND
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Docetaxel anhydrous
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KEGG COMPOUND
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N-debenzoyl-N-(tert-butoxycarbonyl)-10-deacetylpaclitaxel
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ChEBI
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N-debenzoyl-N-(tert-butoxycarbonyl)-10-deacetyltaxol
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ChEBI
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TXL
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DrugBank
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C11231
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KEGG COMPOUND
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D07866
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KEGG DRUG
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DB01248
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DrugBank
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Docetaxel
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Wikipedia
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EP253738
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Patent
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TXL
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PDBeChem
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US4814470
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Patent
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View more database links |
114977-28-5
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CAS Registry Number
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KEGG COMPOUND
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114977-28-5
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CAS Registry Number
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ChemIDplus
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4290183
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Beilstein Registry Number
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Beilstein
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2011-03-18
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Docetaxel is prepared from a natural precursor, 10-deacetylbaccatin III, extracted fron the needles of the European yew tree, Taxus baccata. It is used (often as the trihydrate) for the treatment of breast, ovarian, and non-small cell lung cancer, and with prednisone or prednisolone in hormone-refractory metastatic prostate cancer.
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