(+)-Norgestrel | CAS#797-64-8 | progestin medication

MedKoo Cat#: 597667 | Name: (+)-Norgestrel

Description:

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

(+)-Norgestrel is a progestin medication which is used in birth control pills and in menopausal hormone therapy.

Chemical Structure

(+)-Norgestrel

CAS#797-64-8 (rotation+)

Theoretical Analysis

MedKoo Cat#: 597667

Name: (+)-Norgestrel

CAS#: 797-64-8 (rotation+)

Chemical Formula: C21H28O2

Exact Mass: 312.2089

Molecular Weight: 312.45

Elemental Analysis: C, 80.73; H, 9.03; O, 10.24

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

Bulk Inquiry

Related CAS #

797-64-8 (rotation+) 6533-00-2

Synonym

(+)-Norgestrel; L-Norgestrel; Dextronorgestrel;

IUPAC/Chemical Name

(8S,9R,10S,13R,14R,17S)-13-ethyl-17-ethynyl-17-hydroxy-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-3H-cyclopenta[a]phenanthren-3-one

InChi Key

WWYNJERNGUHSAO-XHCJJCCMSA-N

InChi Code

InChI=1S/C21H28O2/c1-3-20-11-9-17-16-8-6-15(22)13-14(16)5-7-18(17)19(20)10-12-21(20,23)4-2/h2,13,16-19,23H,3,5-12H2,1H3/t16-,17+,18+,19-,20-,21-/m1/s1

SMILES Code

C#C[C@@]1(O)CC[C@]2([H])[C@@]3([H])CCC4=CC(CC[C@@]4([H])[C@]3([H])CC[C@@]12CC)=O

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

Shelf Life

>3 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

2934.99.03.00

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 312.45 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.

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

1: Bifano M, Sevinsky H, Hwang C, Kandoussi H, Jiang H, Grasela D, Bertz R. Effect of the coadministration of daclatasvir on the pharmacokinetics of a combined oral contraceptive containing ethinyl estradiol and norgestimate. Antivir Ther. 2014;19(5):511-9. doi: 10.3851/IMP2718. Epub 2013 Dec 17. PubMed PMID: 24343001. 2: Kaunitz AM, Archer DF, Mishell DR Jr, Foegh M. Safety and tolerability of a new low-dose contraceptive patch in obese and nonobese women. Am J Obstet Gynecol. 2015 Mar;212(3):318.e1-8. doi: 10.1016/j.ajog.2014.09.014. Epub 2014 Sep 16. PubMed PMID: 25220709. 3: Song IH, Borland J, Chen S, Wajima T, Peppercorn AF, Piscitelli SC. Dolutegravir Has No Effect on the Pharmacokinetics of Oral Contraceptives With Norgestimate and Ethinyl Estradiol. Ann Pharmacother. 2015 Jul;49(7):784-9. doi: 10.1177/1060028015580637. Epub 2015 Apr 10. PubMed PMID: 25862012; PubMed Central PMCID: PMC4472613. 4: Nelson AL. Transdermal contraception methods: today's patches and new options on the horizon. Expert Opin Pharmacother. 2015 Apr;16(6):863-73. doi: 10.1517/14656566.2015.1022531. Review. PubMed PMID: 25800084. 5: Hagag P, Steinschneider M, Weiss M. Role of the combination spironolactone-norgestimate-estrogen in Hirsute women with polycystic ovary syndrome. J Reprod Med. 2014 Sep-Oct;59(9-10):455-63. PubMed PMID: 25330687. 6: Darwish M, Bond M, Ricciotti N, Hsieh J, Fiedler-Kelly J, Grasela T. A comparison of the pharmacokinetic profile of an ascending-dose, extended-regimen combined oral contraceptive to those of other extended regimens. Reprod Sci. 2014 Nov;21(11):1401-10. doi: 10.1177/1933719114526472. Epub 2014 Mar 19. PubMed PMID: 24647707. 7: Brenner PF, Mishell DR Jr, Stanczyk FZ, Goebelsmann U. Serum levels of d-norgestrel, luteinizing hormone, follicle-stimulating hormone, estradiol, and progesterone in women during and following ingestion of combination oral contraceptives containing dl-norgestrel. Am J Obstet Gynecol. 1977 Sep 15;129(2):133-40. PubMed PMID: 900174. 8: Fåhraeus L, Larsson-Cohn U, Wallentin L. L-norgestrel and progesterone have different influences on plasma lipoproteins. Eur J Clin Invest. 1983 Dec;13(6):447-53. PubMed PMID: 6416861. 9: Lamparczyk H, Zarzycki PK, Nowakowska J. Effect of temperature on separation of norgestrel enantiomers by high-performance liquid chromatography. J Chromatogr A. 1994 May 13;668(2):413-7. PubMed PMID: 8032490. 10: Bateson D, McNamee K, Briggs P. Newer non-oral hormonal contraception. BMJ. 2013 Feb 14;346:f341. doi: 10.1136/bmj.f341. PubMed PMID: 23412438. 11: Hordge LN, McDaniel KL, Jones DD Jr, Fakayode SO. Simultaneous determination of estrogens (ethinylestradiol and norgestimate) concentrations in human and bovine serum albumin by use of fluorescence spectroscopy and multivariate regression analysis. Talanta. 2016 May 15;152:401-9. doi: 10.1016/j.talanta.2016.02.034. Epub 2016 Feb 17. PubMed PMID: 26992536. 12: Jensen JT, Parke S, Mellinger U, Serrani M, Mabey RG Jr. Hormone withdrawal-associated symptoms: comparison of oestradiol valerate/dienogest versus ethinylestradiol/norgestimate. Eur J Contracept Reprod Health Care. 2013 Aug;18(4):274-83. doi: 10.3109/13625187.2013.785516. Epub 2013 May 2. PubMed PMID: 23638631. 13: Lidegaard O, Nielsen LH, Skovlund CW, Løkkegaard E. Venous thrombosis in users of non-oral hormonal contraception: follow-up study, Denmark 2001-10. BMJ. 2012 May 10;344:e2990. doi: 10.1136/bmj.e2990. PubMed PMID: 22577198; PubMed Central PMCID: PMC3349780. 14: Sisenwine SF, Liu AL, Kimmel HB, Ruelius HW. The conversion of d-norgestrel-3-oxime-17-acetate to d-norgestrel in female rhesus monkeys. Contraception. 1977 Jan;15(1):25-37. PubMed PMID: 407050. 15: Larrañaga A, Sartoretto JN, Winterhalter M, Navas Filho F. Clinical evaluation of two biphasic and one triphasic norgestrel/ethinyl estradiol regimens. Int J Fertil. 1978;23(3):193-9. PubMed PMID: 40893. 16: Nyberg S. Mood and physical symptoms improve in women with severe cyclical changes by taking an oral contraceptive containing 250-mcg norgestimate and 35-mcg ethinyl estradiol. Contraception. 2013 Jun;87(6):773-81. doi: 10.1016/j.contraception.2012.09.024. Epub 2012 Oct 31. PubMed PMID: 23121822. 17: Yuzpe AA, Smith RP, Rademaker AW. A multicenter clinical investigation employing ethinyl estradiol combined with dl-norgestrel as postcoital contraceptive agent. Fertil Steril. 1982 Apr;37(4):508-13. PubMed PMID: 7040117. 18: Yuzpe AA, Lancee WJ. Ethinylestradiol and dl-norgestrel as a postcoital contraceptive. Fertil Steril. 1977 Sep;28(9):932-6. PubMed PMID: 892044. 19: Nilsson CG, Johansson ED, Luukkainen T. A D-norgestrel-releasing IUD. Contraception. 1976 Apr;13(4):503-14. PubMed PMID: 1253602. 20: Bukvic N, Susca F, Bukvic D, Fanelli M, Guanti G. 17-alpha-ethinylestradiol and norgestrel in combination induce micronucleus increases and aneuploidy in human lymphocyte and fibroblast cultures. Teratog Carcinog Mutagen. 2000;20(3):147-59. PubMed PMID: 10820425.