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Trade names | Ortho Tri-Cyclen, others |
Other names | NGM; ORF-10131; Levonorgestrel acetate oxime; Levonorgestrel 17β-acetate 3-oxime; 17α-Ethynyl-18-methyl-19-nortestosterone 3-oxime 17β-acetate; 17α-Ethynyl-18-methylestr-4-en-17β-ol-3-one 3-oxime 17β-acetate |
AHFS/Drugs.com | Professional Drug Facts Professional Drug Facts |
MedlinePlus | a601050 |
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Routes of administration | By mouth |
Drug class | Progestogen; Progestin; Progestogen ester[1] |
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Pharmacokinetic data | |
Bioavailability | Unknown[2] |
Protein binding | • Norelgestromin: 99% (to albumin)[1] • Levonorgestrel: 98% (to albumin and SHBG )[1] • Levonorgestrel acetate: ? (to albumin)[1] |
Metabolism | Liver, intestines (deacetylation, reduction, hydroxylation, conjugation)[1][3][4] |
Metabolites | • Norelgestromin[1] • Levonorgestrel[1] • Levonorgestrel acetate[1] |
Elimination half-life | • Norgestimate: very short[1] • Norelgestromin: 17–37 hours[3][1] • Levonorgestrel: 24–32 hours[1] |
Excretion | Urine: 47%[4] Feces: 37%[4] |
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ECHA InfoCard | 100.167.085 |
Chemical and physical data | |
Formula | C23H31NO3 |
Molar mass | 369.505 g·mol−1 |
3D model (JSmol) | |
Melting point | 214 to 218 °C (417 to 424 °F) |
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Norgestimate, sold under the brand name Ortho Tri-Cyclen among others, is a progestin medication which is used in birth control pills for women and in menopausal hormone therapy.[1][3][4][5] The medication is available in combination with an estrogen and is not available alone.[6] It is taken by mouth.[1]
Side effects of the combination of an estrogen and norgestimate include menstrual irregularities, headaches, nausea, abdominal pain, breast tenderness, mood changes, and others.[3][4] Norgestimate is a progestin, or a synthetic progestogen, and hence is an agonist of the progesterone receptor, the biological target of progestogens like progesterone.[1] It has very weak androgenic activity and no other important hormonal activity.[1] The medication is a prodrug of norelgestromin and to a lesser extent of levonorgestrel in the body.[1]
Norgestimate was patented in 1965 and introduced for medical use, specifically in birth control pills, in 1986.[7][8] It was introduced for use in menopausal hormone therapy in the United States in 1999.[9] Norgestimate is sometimes referred to as a "third-generation" progestin.[10] It is marketed in birth control pills widely throughout the world, whereas it is available for use in menopausal hormone therapy only in the United States and Brazil.[6] Norgestimate is available as a generic medication.[11] In 2022, the combination with ethinylestradiol was the 99th most commonly prescribed medication in the United States, with more than 6 million prescriptions.[12][13]
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