Norgestimate | CAS#35189-28-7

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

MedKoo CAT#: 318380

CAS#: 35189-28-7

Description: Norgestimate is an acetylated progestinused in combination with ethinyl estradiol as an oral contraceptive. It acts as a prodrug to norelgestromin (17-deacetylnorgestimate or levonorgestrel 3-oxime), the primary active metabolite, and levonorgestrel (deacetylation of norgestimate occurs in the intestines and the liver). Unlike levonorgestrel, norgestimate shows high selectivity for the progesterone receptor and low androgenic action due to a large drug-induced elevation in the level of sex hormone-binding globulin (SHBG) (which preferentially binds androgens and thus inhibits their action). In accordance, clinical trials have observed minimal androgenic side effects. Norgestimate and its metabolites themselves, unlike many other progestins, do not bind to SHBG.

Chemical Structure

Norgestimate

CAS# 35189-28-7

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 318380
Name: Norgestimate
CAS#: 35189-28-7
Chemical Formula: C23H31NO3
Exact Mass: 369.23
Molecular Weight: 369.497
Elemental Analysis: C, 74.76; H, 8.46; N, 3.79; O, 12.99

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 220
10mg	USD 350
25mg	USD 670
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

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

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:	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/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. 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

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.

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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.

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