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MedKoo Cat#: 318376 | Name: Norelgestromin
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Norelgestromin is a steroidal progestin used in contraceptive patches, where it is combined with the estrogen ethinyl estradiol. It is one of the active metabolites of norgestimate.

Chemical Structure

Norelgestromin
Norelgestromin
CAS#53016-31-2

Theoretical Analysis

MedKoo Cat#: 318376

Name: Norelgestromin

CAS#: 53016-31-2

Chemical Formula: C21H29NO2

Exact Mass: 327.2198

Molecular Weight: 327.46

Elemental Analysis: C, 77.02; H, 8.93; N, 4.28; O, 9.77

Price and Availability

Size Price Availability Quantity
10mg USD 290.00 2 Weeks
25mg USD 580.00 2 Weeks
50mg USD 950.00 2 Weeks
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Related CAS #
51-98-9 (acetate) 53016-31-2
Synonym
Norelgestromin, Norelgestromine, Levonorgestrel oxime, Norplant 3-oxime, D-Norgestrel 3-oxime
IUPAC/Chemical Name
(8R,9S,10R,13S,14S,17R,E)-13-ethyl-17-ethynyl-17-hydroxy-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3(2H)-one oxime
InChi Key
ISHXLNHNDMZNMC-VTKCIJPMSA-N
InChi Code
InChI=1S/C21H29NO2/c1-3-20-11-9-17-16-8-6-15(22-24)13-14(16)5-7-18(17)19(20)10-12-21(20,23)4-2/h2,13,16-19,23-24H,3,5-12H2,1H3/b22-15+/t16-,17+,18+,19-,20-,21-/m0/s1
SMILES Code
CC[C@]12CC[C@H]3[C@@H](CCC4=C/C(CC[C@H]34)=N/O)[C@@H]1CC[C@@]2(O)C#C
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Norelgestromin is a metabolite of Norgestimate, which is a progestin or synthetic progestogen.
In vitro activity:
TBD
In vivo activity:
TBD
Solvent mg/mL mM
Solubility
DMF 11.0 33.59
DMSO 15.0 45.81
Ethanol 12.0 36.65
PBS (pH 7.2) 0.3 0.76
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 327.46 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
TBD
In vitro protocol:
TBD
In vivo protocol:
TBD
1: Abdallah IA, Hammell DC, Hassan HE, Stinchcomb AL. Norelgestromin/ethinyl estradiol intravenous infusion formulation optimization, stability and compatibility testing: A case study to overcome polysorbate 80 interference in chromatographic analysis. J Pharm Biomed Anal. 2016 Jun 5;125:145-53. doi: 10.1016/j.jpba.2016.03.024. Epub 2016 Mar 19. PubMed PMID: 27018506. 2: Alfaya T, Mur Gimeno P, Iglesias AM, Ventura P. Allergic contact dermatitis caused by an ethinylestradiol-norelgestromin transdermal therapeutic system. Contact Dermatitis. 2011 Apr;64(4):242-4. doi: 10.1111/j.1600-0536.2011.01880.x. PubMed PMID: 21392036. 3: Withdrawn: Norelgestromin/ethinyl estradiol transdermal system. J Med Assoc Thai. 2010 Jul;93(7):873. PubMed PMID: 20695125. 4: Liu X, Ding C, Ge Q, Zhi X, Zhou Z. Determination of norelgestromin in rabbit plasma by LC-MS/MS and its application to the pharmacokinetic study of ORTHO EVRA. J Chromatogr B Analyt Technol Biomed Life Sci. 2009 Jan 15;877(3):311-5. doi: 10.1016/j.jchromb.2008.11.034. Epub 2008 Nov 30. PubMed PMID: 19097950. 5: Piccoli A, Crosignani P, Nappi C, Ronsini S, Bruni V, Marelli S; Italian EVRA Contrast Study Group. Effect of the ethinylestradiol/norelgestromin contraceptive patch on body composition. Results of bioelectrical impedance analysis in a population of Italian women. Nutr J. 2008 Aug 26;7:21. doi: 10.1186/1475-2891-7-21. PubMed PMID: 18727825; PubMed Central PMCID: PMC2557005. 6: Goa KL, Warner GT, Easthope SE. Transdermal ethinylestradiol/norelgestromin: a review of its use in hormonal contraception. Treat Endocrinol. 2003;2(3):191-206. Review. PubMed PMID: 15966567. 7: Stewart FH, Kaunitz AM, Laguardia KD, Karvois DL, Fisher AC, Friedman AJ. Extended use of transdermal norelgestromin/ethinyl estradiol: a randomized trial. Obstet Gynecol. 2005 Jun;105(6):1389-96. PubMed PMID: 15932834. 8: Abrams LS, Skee DM, Natarajan J, Wong FA, Anderson GD. Pharmacokinetics of a contraceptive patch (Evra/Ortho Evra) containing norelgestromin and ethinyloestradiol at four application sites. Br J Clin Pharmacol. 2002 Feb;53(2):141-6. PubMed PMID: 11851637; PubMed Central PMCID: PMC1874289. 9: Abrams LS, Skee DM, Wong FA, Anderson NJ, Leese PT. Pharmacokinetics of norelgestromin and ethinyl estradiol from two consecutive contraceptive patches. J Clin Pharmacol. 2001 Nov;41(11):1232-7. PubMed PMID: 11697756. 10: Crosignani PG, Nappi C, Ronsini S, Bruni V, Marelli S, Sonnino D; Italian EVRA Contrast Study Group. Satisfaction and compliance in hormonal contraception: the result of a multicentre clinical study on women's experience with the ethinylestradiol/norelgestromin contraceptive patch in Italy. BMC Womens Health. 2009 Jun 30;9:18. doi: 10.1186/1472-6874-9-18. PubMed PMID: 19566925; PubMed Central PMCID: PMC2714834. 11: Schwartz JI, Dunbar S, Yuan J, Li S, Miller DL, Rosko K, Johnson-Levonas AO, Lasseter KC, Wagner JA. Influence of taranabant, an orally active, highly selective, potent cannabinoid-1 receptor (CB1R) inverse agonist, on ethinyl estradiol and norelgestromin plasma pharmacokinetics. J Clin Pharmacol. 2009 Jan;49(1):72-9. doi: 10.1177/0091270008325930. Epub 2008 Oct 20. PubMed PMID: 18936284. 12: Taneepanichskul S. Norelgestromin/ethinyl estradiol transdermal system. J Med Assoc Thai. 2005 Oct;88 Suppl 2:S82-4. Review. Retraction in: J Med Assoc Thai. 2010 Jul;93(7):873. PubMed PMID: 17722322. 13: Graziottin A. A review of transdermal hormonal contraception : focus on the ethinylestradiol/norelgestromin contraceptive patch. Treat Endocrinol. 2006;5(6):359-65. Review. PubMed PMID: 17107221. 14: Wooltorton E. The Evra (ethinyl estradiol/norelgestromin) contraceptive patch: estrogen exposure concerns. CMAJ. 2006 Jan 17;174(2):164-5. Epub 2005 Dec 20. Erratum in: CMAJ. 2008 Jun 17;178(13):1688. Dosage error in article text. PubMed PMID: 16368722; PubMed Central PMCID: PMC1329453. 15: Prifti S, Lelle I, Strowitzki T, Rabe T. Induction of androgen receptor activity by norgestimate and norelgestromin in MDA-MB 231 breast cancer cells. Gynecol Endocrinol. 2004 Jul;19(1):18-21. PubMed PMID: 15625768. 16: Ethinylestradiol + norelgestromin: new preparation. Transdermal contraception: no tangible progress. Prescrire Int. 2004 Aug;13(72):123-6. PubMed PMID: 15532134. 17: Prifti S, Lelle I, Zhong G, Strowitzki T, Rabe T. Matrix metalloproteinase 2 and tissue inhibitor of metalloproteinase 2 expression is not regulated by norgestimate or norelgestromin. Gynecol Endocrinol. 2004 Jan;18(1):23-7. PubMed PMID: 15106361. 18: Faculty of Family Planning and Reproductive Health Care Clinical Effectiveness Unit. New Product Review (September 2003). Norelgestromin/ethinyl oestradiol transdermal contraceptive system (Evra). J Fam Plann Reprod Health Care. 2004 Jan;30(1):43-5. PubMed PMID: 15006313. 19: Pasqualini JR, Caubel P, Friedman AJ, Philippe JC, Chetrite GS. Norelgestromin as selective estrogen enzyme modulator in human breast cancer cell lines. Effect on sulfatase activity in comparison to medroxyprogesterone acetate. J Steroid Biochem Mol Biol. 2003 Feb;84(2-3):193-8. PubMed PMID: 12711003. 20: Creasy GW, Fisher AC, Hall N, Shangold GA. Transdermal contraceptive patch delivering norelgestromin and ethinyl estradiol. Effects on the lipid profile. J Reprod Med. 2003 Mar;48(3):179-86. PubMed PMID: 12698776.