Norelgestromin, or norelgestromine, sold under the brand names Evra and Ortho Evra among others, is a
progestin medication which is used as a method of
birth control for women.[5][6][7] The medication is available in combination with an
estrogen and is not available alone.[5] It is used as a
patch that is applied to the skin.[6][7]
Norelgestromin was introduced for medical use in 2002.[10] It is sometimes referred to as a "third-generation" progestin.[11][12] Norelgestromin is marketed widely throughout the world.[5] It is available as a
generic medication.[13]
Norelgestromin is available only as a transdermal contraceptive patch in combination with ethinyl estradiol.[6] The Ortho Evra patch is a 20 cm2, once-weekly adhesive that contains 6.0 mg norelgestromin and 0.6 mg ethinyl estradiol and delivers 200 μg/day norelgestromin and 35 μg/day ethinyl estradiol.[4][14]
Norelgestromin is a
progestogen.[3][4] It is one of the
active metabolites of
norgestimate.[8][9] Unlike many related progestins, norelgestromin reportedly has negligible
androgenic activity.[9] However, it produces
levonorgestrel as an active metabolite to some extent, which does have some androgenic activity.[4][3] Nonetheless, transdermally-administered norelgestromin does not counteract the increase in
sex hormone-binding globulin levels produced by ethinyl estradiol.[4]
Relative affinities (%) of norelgestromin and metabolites
Notes: Values are percentages (%). Reference
ligands (100%) were
prome- gestone for the
PRTooltip progesterone receptor,
metribolone for the
ARTooltip androgen receptor,
E2 for the
ERTooltip estrogen receptor,
DEXATooltip dexamethasone for the
GRTooltip glucocorticoid receptor,
aldosterone for the
MRTooltip mineralocorticoid receptor,
DHTTooltip dihydrotestosterone for
SHBGTooltip sex hormone-binding globulin, and
cortisol for
CBGTooltip Corticosteroid-binding globulin. Sources:[15][3][16]
Pharmacokinetics
Upon application of a transdermal patch containing norelgestromin and ethinyl estradiol,
plateau levels of both are reached by approximately 48 hours, and
steady-state levels are reached within 2 weeks of application.[4] Absorption following application to the buttock, upper outer arm, abdomen, and upper torso was assessed and, while absorption from the abdomen was slightly lower, it was considered to be therapeutically equivalent for the various areas.[4] Mean levels of norelgestromin at steady-state ranged from 0.305 ng/mL to 1.53 ng/mL, with an average of about 0.725 ng/mL.[4] The
plasma protein binding of norelgestromin is 99%, and it is bound to
albumin but not to
sex hormone-binding globulin.[1][2][3]
Norelgestromin was introduced for medical use in 2002.[10]
Society and culture
Generic names
Norelgestromin is the
generic name of the drug and its
INNTooltip International Nonproprietary Name,
USANTooltip United States Adopted Name, and
BANTooltip British Approved Name.[5] The combined ethinyl estradiol and norelgestromin contraceptive patch is also known by its developmental code name RWJ-10553.[22]
Brand names
Norelgestromin is marketed under the brand names Evra, Ortho Evra, Xulane, and others, all in combination with
ethinylestradiol.[5][13]
A
transdermalgel formulation of norgelstromin and
ethinyl estradiol was under development by Antares Pharma for use as a method of birth control with the code name AP-1081 but development was discontinued.[23]
^Philibert D, Bouchoux F, Degryse M, Lecaque D, Petit F, Gaillard M (October 1999). "The pharmacological profile of a novel norpregnance progestin (trimegestone)". Gynecological Endocrinology. 13 (5): 316–326.
doi:
10.3109/09513599909167574.
PMID10599548.
^US 7345183, Tombari DG, Vecchioli A, "Process for obtaining norelgestromin in different relations of isomers E and Z", issued 18 March 2008, assigned to Gador SA.
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PMID11991433.
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PMID12953327.
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doi:
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PMID15323313.
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PMID17044218.
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PMID17472863.
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