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SML0359

Sigma-Aldrich

Norgestimate

≥97% (HPLC)

Synonym(s):

(17α)-17-(Acetyloxy)-13-ethyl-18,19-dinorpregn-4-en-20-yn-3-one 3-oxime, Dexnorgestrel acetime

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About This Item

Empirical Formula (Hill Notation):
C23H31NO3
CAS Number:
35189-28-7
Molecular Weight:
369.50
MDL number:
MFCD00867874
UNSPSC Code:
51111800
PubChem Substance ID:
329825361
NACRES:
NA.77

Assay

≥97% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 5 mg/mL (clear solution)

storage temp.

−20°C

SMILES string

CC[C@]12CC[C@H]3[C@@H](CCC4=C\C(CC[C@H]34)=N\O)[C@@H]1CC[C@@]2(OC(C)=O)C#C

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

InChI key

KIQQMECNKUGGKA-NMYWJIRASA-N

Gene Information

human ... PGR(5241)

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Biochem/physiol Actions

Norgestimate is a synthetic progestin used in combination with estrogens as a contraceptive.

Features and Benefits

This compound is featured on the Nuclear Receptors (Steroids) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Pictograms

Health hazardExclamation mark
GHS08,GHS07

Signal Word

Warning

Hazard Statements

H302,H315,H319,H361fd

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Repr. 2 - Skin Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Jason D Vescovi et al.
Contraception, 77(2), 97-104 (2008-01-30)
We examined the response of bone turnover markers and indices of energy status after 2 weeks of oral contraceptive (OC) therapy in premenopausal women with exercise-associated menstrual disturbances (EAMD). Six women with EAMD received one 28-day cycle of a triphasic
Susan Jick et al.
Contraception, 76(1), 4-7 (2007-06-26)
In 2006, we published a study that indicated that the new transdermal contraceptive patch containing ethinyl estradiol (EE) and the progestin norelgestromin did not increase the risk for venous thromboembolism (VTE) compared to oral contraceptive containing norgestimate and 35 microg
Matt S Anderson et al.
British journal of clinical pharmacology, 71(4), 616-620 (2011-03-15)
Oral contraceptives such as norgestimate-ethinyl estradiol (Ortho Tri-Cyclen®) are commonly prescribed in the HIV-infected patient population. A placebo-controlled, randomized, two-period crossover study in healthy HIV-seronegative subjects was conducted to assess the effect of raltegravir on the pharmacokinetics of the estrogen
Teri Greco et al.
Contraception, 76(1), 8-17 (2007-06-26)
This study compared two oral contraceptives (OCs) with the same triphasic regimen of progestin (norgestimate 0.18, 0.215 and 0.25 mg) but differing doses of ethinyl estradiol (EE) - 25 and 35 microg EE - in their effects on androgens, mood
Ronald T Burkman et al.
Contraception, 79(6), 424-427 (2009-05-16)
This analysis investigated the association of oral contraceptive efficacy with body weight and body mass index (BMI) for hypothesis-generating purposes. Data were from a randomized, parallel-group trial of 180/215/250 mcg of norgestimate (NGM)/25 mcg of ethinyl estradiol (EE) (given to
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