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1. Norgestrel Oxime Acetate
1. Dexnorgestrel Acetime
2. 35189-28-7
3. Anti-norgestimate
4. Norgestimate, E-
5. Norgestimato
6. Norgestimatum
7. Norgestimatum [inn-latin]
8. Norgestimato [inn-spanish]
9. Orf-10131
10. Nkx8dn6ty9
11. [(3e,8r,9s,10r,13s,14s,17r)-13-ethyl-17-ethynyl-3-hydroxyimino-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-yl] Acetate
12. (+)-13-ethyl-17-hydroxy-18,19-dinor-17alpha-pregn-4-en-20-yn-3-one Oxime Acetate (ester)
13. 20799-27-3
14. Chebi:50815
15. Orf 10131
16. Rwj 10131
17. Ncgc00181353-01
18. (17alpha)-17-(acetyloxy)-13-ethyl-18,19-dinorpregn-4-en-20-yn-3-one 3-oxime
19. Dsstox_cid_26922
20. Dsstox_rid_82018
21. Dsstox_gsid_46922
22. 107382-52-5
23. D-13beta-ethyl-17alpha-ethynyl-17beta-acetoxygon-4-en-3-one Oxime
24. Rwj-10131
25. Cas-35189-28-7
26. Norgestimate (usp/inn)
27. Nsc-759159
28. Unii-nkx8dn6ty9
29. Schembl38317
30. Schembl38318
31. Chembl1200934
32. Dtxsid1046922
33. Norgestimate, >=97% (hplc)
34. Norgestimate For System Suitability
35. Tox21_112811
36. Ac-655
37. (3e)-17alpha-ethynyl-3-(hydroxyimino)-18a-homoestr-4-en-17beta-yl Acetate
38. Akos015917555
39. Tox21_112811_1
40. Db00957
41. Ncgc00344561-01
42. As-12305
43. D05209
44. 351n287
45. A822635
46. J-019983
47. 18,19-dinorpregn-4-en-20-yn-3-one, 17-(acetyloxy)-13-ethyl-, 3-oxime, (3e,17alpha)-
48. (1s,2r,5e,10r,11s,14r,15s)-15-ethyl-14-ethynyl-5-(hydroxyimino)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-14-yl Acetate
49. [(3e,8r,9s,10r,13s,14s,17r)-13-ethyl-17-ethynyl-3-hydroxyimino-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-yl] Acetate;norgestimate
50. 18,19-dinorpregn-4-en-20-yn-3-one, 17-(acetyloxy)-13-ethyl-, 3-oxime, (3e,17.alpha.)-
| Molecular Weight | 369.5 g/mol |
|---|---|
| Molecular Formula | C23H31NO3 |
| XLogP3 | 4.1 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 4 |
| Rotatable Bond Count | 4 |
| Exact Mass | 369.23039385 g/mol |
| Monoisotopic Mass | 369.23039385 g/mol |
| Topological Polar Surface Area | 58.9 Ų |
| Heavy Atom Count | 27 |
| Formal Charge | 0 |
| Complexity | 744 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 6 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 1 |
| Undefined Bond Stereocenter Count | 0 |
| Covalently Bonded Unit Count | 1 |
Contraceptives, Oral, Synthetic; Norgestrel/analogs & derivatives
National Library of Medicine's Medical Subject Headings online file (MeSH, 2009)
Norgestimate/ethinyl estradiol is indicated for the prevention of pregnancy in women who elect to use oral contraceptives as a method of contraception. /Included in US product label/
US Natl Inst Health; DailyMed. Current Medication Information for MONONESSA (norgestimate and ethinyl estradiol) kit (December 2010). Available from, as of March 30, 2011: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=33976
/BOXED WARNING/ WARNINGS: CARDIOVASCULAR RISK ASSOCIATED WITH SMOKING. Cigarette smoking increases the risk of serious cardiovascular events from combination oral contraceptive use. This risk increases with age, particularly in women over 35 years of age, and with the number of cigarettes smoked. For this reason, combination oral contraceptives, including MonoNessa, should not be used by women who are over 35 years of age and smoke.
US Natl Inst Health; DailyMed. Current Medication Information for MONONESSA (norgestimate and ethinyl estradiol) kit (Updated: February 2015). Available from, as of April 23, 2015: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=704ba4ae-edd0-4298-a399-03a49f8411c7
Oral contraceptives should not be used in women who currently have the following conditions: thrombophlebitis or thromboembolic disorders; a past history of deep vein thrombophlebitis or thromboembolic disorders; cerebral vascular or coronary artery disease (current or past history); valvular heart disease with complications; severe hypertension; diabetes with vascular involvement; headaches with focal neurological symptoms; major surgery with prolonged immobilization; known or suspected carcinoma of the breast or personal history of breast cancer; carcinoma of the endometrium or other known or suspected estrogen-dependent neoplasia; undiagnosed abnormal genital bleeding; cholestatic jaundice of pregnancy or jaundice with prior pill use; acute or chronic hepatocellular disease with abnormal liver function; hepatic adenomas or carcinomas; known or suspected pregnancy; hypersensitivity to any component of this product.
US Natl Inst Health; DailyMed. Current Medication Information for MONONESSA (norgestimate and ethinyl estradiol) kit (December 2010). Available from, as of March 30, 2011: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=33976
The use of oral contraceptives is associated with increased risks of several serious conditions including myocardial infarction, thromboembolism, stroke, hepatic neoplasia, and gallbladder disease, although the risk of serious morbidity or mortality is very small in healthy women without underlying risk factors. The risk of morbidity and mortality increases significantly in the presence of other underlying risk factors such as hypertension, hyperlipidemias, obesity and diabetes.
US Natl Inst Health; DailyMed. Current Medication Information for MONONESSA (norgestimate and ethinyl estradiol) kit (December 2010). Available from, as of March 30, 2011: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=33976
Oral contraceptives have been shown to increase both the relative and attributable risks of cerebrovascular events (thrombotic and hemorrhagic strokes), although, in general, the risk is greatest among older (>35 years), hypertensive women who also smoke. Hypertension was found to be a risk factor for both users and nonusers, for both types of strokes, and smoking interacted to increase the risk of stroke. In a large study, the relative risk of thrombotic strokes has been shown to range from 3 for normotensive users to 14 for users with severe hypertension. The relative risk of hemorrhagic stroke is reported to be 1.2 for non-smokers who used oral contraceptives, 2.6 for smokers who did not use oral contraceptives, 7.6 for smokers who used oral contraceptives, 1.8 for normotensive users and 25.7 for users with severe hypertension. The attributable risk is also greater in older women.
US Natl Inst Health; DailyMed. Current Medication Information for MONONESSA (norgestimate and ethinyl estradiol) kit (December 2010). Available from, as of March 30, 2011: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=33976
For more Drug Warnings (Complete) data for Norgestimate (44 total), please visit the HSDB record page.
Norgestimate is formulated with [ethinylestradiol] as a combined oral contraceptive. It can also be given with low dose ethinylestradiol for contraception as well as the treatment of moderate acne vulgaris in women 15 years old.
Norgestimate is a progestin that suppresses ovulation for contraception and reduces free testosterone to treat moderate acne vulgaris. The therapeutic index is wide as overdoses are rare. Patients should be counselled regarding the risk of vascular problems, liver disease, hypertension, metabolic effects, headaches, and bleeding irregularities.
Contraceptives, Oral, Synthetic
Oral contraceptives which owe their effectiveness to synthetic preparations. (See all compounds classified as Contraceptives, Oral, Synthetic.)
Contraceptive Agents, Hormonal
Contraceptive agents that act on the ENDOCRINE SYSTEM. (See all compounds classified as Contraceptive Agents, Hormonal.)
Absorption
Oral norgestimate has a Tmax of 0.5-2h. On day 21 of cycle 3, 17-desacetylnorgestimate reaches a Cmax of 1.82ng/mL, with a Tmax of 1.5h, and an AUC of 16.1h\*ng/mL. At the same time, norgestrel reaches a Cmax of 2.79ng/mL, with a Tmax of 1.7h, and an AUC of 49.9h\*ng/mL.
Route of Elimination
Norgestimate is 45-49% eliminated in urine and 16-49% eliminated in feces. Unchanged norgestimate is not detected in urine.
Volume of Distribution
Data regarding the volume of distribution of norgestimate are not readily available.
Clearance
Data regarding the clearance of norgestimate is not readily available.
Norgestimate (NGM) and ethinyl estradiol (EE) are rapidly absorbed following oral administration.
US Natl Inst Health; DailyMed. Current Medication Information for MONONESSA (norgestimate and ethinyl estradiol) kit (December 2010). Available from, as of March 30, 2011: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=33976
Peak serum concentrations of norelgestromin (NGMN) and ethinyl estradiol (EE) are generally reached by 2 hours after administration of MonoNessa. Accumulation following multiple dosing of the 250 ug Norgestimate (NGM)/ 35 ug dose is approximately 2-fold for NGMN and EE compared with single dose administration. The pharmacokinetics of NGMN is dose proportional following NGM doses of 180 ug to 250 ug. ... Steady-state concentrations of NGMN and NG are achieved by Day 21. Non-linear accumulation (approximately 8 fold) of norgestrel is observed as a result of high affinity binding to SHBG (sex hormone-binding globulin), which limits its biological activity.
US Natl Inst Health; DailyMed. Current Medication Information for MONONESSA (norgestimate and ethinyl estradiol) kit (December 2010). Available from, as of March 30, 2011: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=33976
Norelgestromin and norgestrel are highly bound (>97%) to serum proteins. Norelgestromin is bound to albumin and not to SHBG, while norgestrel is bound primarily to SHBG.
US Natl Inst Health; DailyMed. Current Medication Information for MONONESSA (norgestimate and ethinyl estradiol) kit (December 2010). Available from, as of March 30, 2011: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=33976
The metabolites of norelgestromin and ethinyl estradiol are eliminated by renal and fecal pathways. Following administration of 14C-norgestimate, 47% (45-49%) and 37% (16-49%) of the administered radioactivity was eliminated in the urine and feces, respectively. Unchanged norgestimate was not detected in the urine.
US Natl Inst Health; DailyMed. Current Medication Information for MONONESSA (norgestimate and ethinyl estradiol) kit (December 2010). Available from, as of March 30, 2011: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=33976
Norgestimate is rapidly deacetylated to the active 17-desacetylnorgestimate, which is deoximated to the active norgestrel. 17-desacetylnorgestimate is metabolized to a number of undefined hydroxylated metabolites, mainly by CYP3A4 and to a lesser extend by CYP2B6 and CYP2C9. Norgestrel is O-glucuronidated by UGT1A1 or oxidized to a number of undefined hydroxylated metabolites by CYP3A4.
Norgestimate is rapidly and completely metabolized by first pass (intestinal and/or hepatic) mechanisms to norelgestromin (NGMN) and norgestrel (NG), which are the major active metabolites of norgestimate.
US Natl Inst Health; DailyMed. Current Medication Information for MONONESSA (norgestimate and ethinyl estradiol) kit (December 2010). Available from, as of March 30, 2011: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=33976
Norgestimate is extensively metabolized by first-pass mechanisms in the gastrointestinal tract and/or liver. Norgestimate's primary active metabolite is norelgestromin. Subsequent hepatic metabolism of norelgestromin occurs and metabolites include norgestrel, which is also active, and various hydroxylated and conjugated metabolites.
US Natl Inst Health; DailyMed. Current Medication Information for MONONESSA (norgestimate and ethinyl estradiol) kit (December 2010). Available from, as of March 30, 2011: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=33976
In addition to 17-deacetyl norgestimate, a number of metabolites of norgestimate have been identified in human urine following administration of radiolabeled norgestimate. These include 18,19-Dinor-17-pregn-4-en-20-yn-3-one,17-hydroxy-13-ethyl,(17alpha)-(-); 18,19-Dinor-5beta-17-pregnan-20-yn,3alpha,17beta-dihydroxy-13-ethyl,(17alpha), various hydroxylated metabolites and conjugates of these metabolites.
US Natl Inst Health; DailyMed. Current Medication Information for MONONESSA (norgestimate and ethinyl estradiol) kit (December 2010). Available from, as of March 30, 2011: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=33976
There is limited information on the metabolism of levonorgestrel, norethindrone and structurally related contraceptive steroids. Both levonorgestrel and norethindrone undergo extensive reduction of the alpha, beta-unsaturated ketone in ring A. Levonorgestrel also undergoes hydroxylation at carbons 2 and 16. The metabolites of both compounds circulate predominantly as sulfates. In urine, levonorgestrel metabolites are found primarily in the glucuronide form, whereas norethindrone metabolites are present in approximately equal amounts as sulfates and glucuronides. Of the progestogens structurally related to norethindrone, norethindrone acetate, ethynodiol diacetate, norethindrone enanthate, and perhaps lynestrenol, undergo rapid hydrolysis and are converted to the parent compound and its metabolites. There is no convincing evidence that norethynodrel is converted to norethindrone. Of the progestogens structurally related to levonorgestrel, it appears that neither desogestrel nor gestodene are transformed to the parent compound. However, there is evidence that norgestimate can be, at least partly, converted to levonorgestrel. ...
PMID:2143719 Stanczyk FZ, Roy S; Contraception 42 (1): 67-96 (1990)
Norgestimate is rapidly deacetylated. The active metabolites of norgestimate, 17-desacetyl norgestimate, has a half life of 12-30h, while norgestrel has a half life of 36.410.2h.
Progesterone analogs like norgestimate decrease the frequency of gonadotropin releasing hormone pulses from the hypothalamus, decreasing follicle stimulating hormone and luteinizing hormone. These actions prevent ovulation. Norgestimate suppresses the hypothalamo-pituitary-axis, reducing androgen synthesis. It also induces production of sex hormone binding globulin, which decreases free testosterone. These actions together result in less testosterone being available to stimulate sebaceous glands, resulting in effective treatment of some forms of acne.
Combination oral contraceptives act by suppression of gonadotropins. Although the primary mechanism of this action is inhibition of ovulation, other alterations include changes in the cervical mucus (which increase the difficulty of sperm entry into the uterus) and the endometrium (which reduce the likelihood of implantation).
US Natl Inst Health; DailyMed. Current Medication Information for MONONESSA (norgestimate and ethinyl estradiol) kit (December 2010). Available from, as of March 30, 2011: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=33976
Receptor binding studies, as well as studies in animals and humans, have shown that norgestimate and 17-deacetyl norgestimate, the major serum metabolite, combine high progestational activity with minimal intrinsic androgenicity. Norgestimate, in combination with ethinyl estradiol, does not counteract the estrogen-induced increases in sex hormone binding globulin (SHBG), resulting in lower serum testosterone.
US Natl Inst Health; DailyMed. Current Medication Information for MONONESSA (norgestimate and ethinyl estradiol) kit (December 2010). Available from, as of March 30, 2011: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=33976
Progestins enter target cells by passive diffusion and bind to cytosolic (soluble) receptors that are loosely bound in the nucleus. The steroid receptor complex initiates transcription, resulting in an increase in protein synthesis. /Progestins/
USP. Convention. USPDI - Drug Information for the Health Care Professional. 20th ed. Volume I. Micromedex, Inc. Englewood, CO., 2000. Content Reviewed and Approved by the U.S. Pharmacopeial Convention, Inc., p. 2568
Progestins are capable of affecting serum concentrations of other hormones, particularly estrogen. Estrogenic effects are modified by the progestins, either by reducing the availability or stability of the hormone receptor complex or by turning off specific hormone-responsive genes by direct interaction with the progestin receptor in the nucleus. In addition, estrogen priming is necessary to increase progestin effects by upregulating the number of progestin receptors and/or increasing progesterone production, causing a negative feedback mechanism that inhibits estrogen receptors. /Progestins/
USP. Convention. USPDI - Drug Information for the Health Care Professional. 20th ed. Volume I. Micromedex, Inc. Englewood, CO., 2000. Content Reviewed and Approved by the U.S. Pharmacopeial Convention, Inc., p. 2568
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DOSAGE - TABLET;ORAL-28 - 0.035MG;0.25MG **Fe...DOSAGE - TABLET;ORAL-28 - 0.035MG;0.25MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**
USFDA APPLICATION NUMBER - 19653
DOSAGE - TABLET;ORAL-28 - 0.035MG,0.035MG,0.0...DOSAGE - TABLET;ORAL-28 - 0.035MG,0.035MG,0.035MG;0.18MG,0.215MG,0.25MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**
USFDA APPLICATION NUMBER - 19697
DOSAGE - TABLET;ORAL-28 - 0.025MG,0.025MG,0.0...DOSAGE - TABLET;ORAL-28 - 0.025MG,0.025MG,0.025MG;0.18MG,0.215MG,0.25MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**
USFDA APPLICATION NUMBER - 21241
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