Synonym
Norgestimate, Norgestrel oxime acetate, Dexnorgestrel acetime, ORF-10131, D 138, AC-655, RWJ-10131
IUPAC/Chemical Name
[(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
InChi Key
KIQQMECNKUGGKA-NMYWJIRASA-N
InChi Code
InChI=1S/C23H31NO3/c1-4-22-12-10-19-18-9-7-17(24-26)14-16(18)6-8-20(19)21(22)11-13-23(22,5-2)27-15(3)25/h2,14,18-21,26H,4,6-13H2,1,3H3/b24-17+/t18-,19+,20+,21-,22-,23-/m0/s1
SMILES Code
CC(O[C@@]1(C#C)CC[C@@]2([H])[C@]3([H])CCC4=C/C(CC[C@]4([H])[C@@]3([H])CC[C@]12CC)=N/O)=O
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
Biological target:
Norgestimate is an orally active progestin with highly selective progestational activity and minimal androgenicity.
In vitro activity:
This study shows that norgestimate, an acetylated progestin, effectively inhibits biofilm formation by staphylococcal strains, including methicillin-resistant S. aureus, without inhibiting their growth, decreasing the selective pressure for emergence of resistance. Norgestimate inhibits staphylococcal biofilm formation by inhibiting production of polysaccharide intercellular adhesin and proteins in the extracellular matrix.
Reference: NPJ Biofilms Microbiomes. 2017 Jul 21;3:18. https://pubmed.ncbi.nlm.nih.gov/28758016/
In vivo activity:
In in vivo studies, norgestimate stimulated the endometrium in immature rabbits when applied directly to the uterus, again suggesting that bio-transformation to an active metabolite is not required for expression of norgestimate's pharmacological activity.
Reference: Contraception. 1985 Sep;32(3):311-9. https://pubmed.ncbi.nlm.nih.gov/3936677/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMF |
16.0 |
43.30 |
| DMF:PBS (pH 7.2) (1:2) |
0.3 |
0.81 |
| DMSO |
14.0 |
37.89 |
| Ethanol |
3.0 |
8.12 |
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
369.50
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 |
Formulation protocol:
1. Yoshii Y, Okuda KI, Yamada S, Nagakura M, Sugimoto S, Nagano T, Okabe T, Kojima H, Iwamoto T, Kuwano K, Mizunoe Y. Norgestimate inhibits staphylococcal biofilm formation and resensitizes methicillin-resistant Staphylococcus aureus to β-lactam antibiotics. NPJ Biofilms Microbiomes. 2017 Jul 21;3:18. doi: 10.1038/s41522-017-0026-1. Erratum in: NPJ Biofilms Microbiomes. 2017 Nov 8;3:30. PMID: 28758016; PMCID: PMC5522392.
2. Paris F, Rabeolina F, Balaguer P, Bacquet A, Sultan C. Antiandrogenic activity of norgestimate in a human androgen-dependent stable-transfected cell line. Gynecol Endocrinol. 2007 Apr;23(4):193-7. doi: 10.1080/09513590701214414. PMID: 17505938.
3. Killinger J, Hahn DW, Phillips A, Hetyei NS, McGuire JL. The affinity of norgestimate for uterine progestogen receptors and its direct action on the uterus. Contraception. 1985 Sep;32(3):311-9. doi: 10.1016/0010-7824(85)90054-x. PMID: 3936677.
In vitro protocol:
1. Yoshii Y, Okuda KI, Yamada S, Nagakura M, Sugimoto S, Nagano T, Okabe T, Kojima H, Iwamoto T, Kuwano K, Mizunoe Y. Norgestimate inhibits staphylococcal biofilm formation and resensitizes methicillin-resistant Staphylococcus aureus to β-lactam antibiotics. NPJ Biofilms Microbiomes. 2017 Jul 21;3:18. doi: 10.1038/s41522-017-0026-1. Erratum in: NPJ Biofilms Microbiomes. 2017 Nov 8;3:30. PMID: 28758016; PMCID: PMC5522392.
2. Paris F, Rabeolina F, Balaguer P, Bacquet A, Sultan C. Antiandrogenic activity of norgestimate in a human androgen-dependent stable-transfected cell line. Gynecol Endocrinol. 2007 Apr;23(4):193-7. doi: 10.1080/09513590701214414. PMID: 17505938.
In vivo protocol:
1. Killinger J, Hahn DW, Phillips A, Hetyei NS, McGuire JL. The affinity of norgestimate for uterine progestogen receptors and its direct action on the uterus. Contraception. 1985 Sep;32(3):311-9. doi: 10.1016/0010-7824(85)90054-x. PMID: 3936677.
1: Curran MP, Wagstaff AJ. Spotlight on estradiol and norgestimate as hormone replacement therapy in postmenopausal women. Treat Endocrinol. 2002;1(2):127-9. Review. PubMed PMID: 15765628.
2: Curran MP, Wagstaff AJ. Estradiol and norgestimate: a review of their combined use as hormone replacement therapy in postmenopausal women. Drugs Aging. 2001;18(11):863-85. Review. PubMed PMID: 11772126.
3: Henzl MR. Norgestimate. From the laboratory to three clinical indications. J Reprod Med. 2001 Jul;46(7):647-61. Review. PubMed PMID: 11499185.
4: Sobel NB. Progestins in preventive hormone therapy. Including pharmacology of the new progestins, desogestrel, norgestimate, and gestodene: are there advantages? Obstet Gynecol Clin North Am. 1994 Jun;21(2):299-319. Review. PubMed PMID: 7936546.
5: Anderson FD, Gillmer MD. Norgestimate: overview of a monophasic formulation. Int J Fertil Menopausal Stud. 1993;38 Suppl 3:126-32. Review. PubMed PMID: 8260971.
6: Phillips A, Hahn DW, McGuire JL. Preclinical evaluation of norgestimate, a progestin with minimal androgenic activity. Am J Obstet Gynecol. 1992 Oct;167(4 Pt 2):1191-6. Review. PubMed PMID: 1415445.
7: McGuire JL, Phillips A, Hahn DW, Tolman EL, Flor S, Kafrissen ME. Pharmacologic and pharmacokinetic characteristics of norgestimate and its metabolites. Am J Obstet Gynecol. 1990 Dec;163(6 Pt 2):2127-31. Review. PubMed PMID: 2124088.
8: Lippman JS, Shangold GA. A review of post-marketing safety and surveillance data for oral contraceptives containing norgestimate and ethinyl estradiol. Int J Fertil Womens Med. 1997 Jul-Aug;42(4):230-9. Review. PubMed PMID: 9309456.
9: Corson SL. Norgestimate. Clin Obstet Gynecol. 1995 Dec;38(4):841-8. Review. PubMed PMID: 8616980.
10: Kaplan B. Desogestrel, norgestimate, and gestodene: the newer progestins. Ann Pharmacother. 1995 Jul-Aug;29(7-8):736-42. Review. PubMed PMID: 8520092.
11: Corson SL. Efficacy and safety of a monophasic and a triphasic oral contraceptive containing norgestimate. Am J Obstet Gynecol. 1994 May;170(5 Pt 2):1556-61. Review. PubMed PMID: 8178906.
12: London RS. The new era in oral contraception: pills containing gestodene, norgestimate, and desogestrel. Obstet Gynecol Surv. 1992 Nov;47(11):777-82. Review. PubMed PMID: 1436906.
13: Bringer J. Norgestimate: a clinical overview of a new progestin. Am J Obstet Gynecol. 1992 Jun;166(6 Pt 2):1969-77. Review. PubMed PMID: 1605287.
14: Anderson FD. Norgestimate: a preclinical profile. Int J Fertil. 1992;37 Suppl 1:27-35. Review. PubMed PMID: 1347518.
15: Chez RA. Clinical aspects of three new progestogens: desogestrel, gestodene, and norgestimate. Am J Obstet Gynecol. 1989 May;160(5 Pt 2):1296-300. Review. PubMed PMID: 2524163.
