CAS 53016-31-2|15-ethyl-14-ethynyl-5-(hydroxyimino)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-14-ol|Orthra Evra|15-ethyl-14-ethynyl-5-(hydroxyimino)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-...

General Information

Structure

Molecular Formula

C₂₁H₂₉NO₂

Molecular Mass

327.46046

Exact Mass

327.21982917

Charge

InChI

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

InChIKey

ISHXLNHNDMZNMC-UHFFFAOYSA-N

Canonic Smiles

O/N=C\1/CCC2C(=C1)CCC1C2CCC2(C1CCC2(O)C#C)CC

Isomeric Smiles

CCC12CCC3C(C1CCC2(C#C)O)CCC1=C/C(=N\O)/CCC31

Calculated Properties

JChem

Acid pKa

11.466128

H Acceptors

H Donor

LogD (pH = 5.5)

3.6694894

LogD (pH = 7.4)

3.6712167

Log P

3.6712763

Molar Refractivity

95.8472

Polarizability

37.191574

Polar Surface Area

52.82

Rotatable Bonds

Lipinski's Rule of Five

true

ALOGPS 2.1

Log P

3.18

LOG S

-4.73

Solubility (Water)

6.05e-03 g/l

Data Source

Academic Data

Data Source

Names and Identifiers

IUPAC name

15-ethyl-14-ethynyl-5-(hydroxyimino)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-14-ol

Brand Name

Orthra Evra

IUPAC Traditional name

15-ethyl-14-ethynyl-5-(hydroxyimino)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-14-ol

Synonyms

Norelgestromin

Names and Identifiers

Registration numbers

PubChem CID

13752005

PubChem SID

16096788299443265

CAS Number

53016-31-2

Registration numbers

Properties

No Data Available

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Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

DrugBank

DB06713

Drug Groups

approved

Description

Norelgestromin is a drug used in contraception. Norelgestromin is the active progestin responsible for the progestational activity that occurs in women after application of ORTHO EVRA patch.

Indication

Norelgestromin is used for contraception and menopausal hormonal therapy. Norelgestromin may potentially be used in breast cancer treatment due to its inhibitory effect on estrone sulfatase . They convert sulfated steroid precursors to estrogen during pregnancy.

Pharmacology

Norelgestromin is used for contraception and menopausal hormonal therapy transdermally or in combination with ethinyl estradiol as a vaginal ring. Norelgestromin, in combination with ethinyl estradiol inhibits ovulation by suppressing gonadotropins.

References

• Goa KL, Warner GT, Easthope SE: Transdermal ethinylestradiol/norelgestromin: a review of its use in hormonal contraception. Treat Endocrinol. 2003;2(3):191-206. [Pubmed]

• Henzl MR: Norgestimate. From the laboratory to three clinical indications. J Reprod Med. 2001 Jul;46(7):647-61. [Pubmed]

• 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]

External Links

• [Wikipedia]

Molecule Details

References

PubChem Literature

From Data Sources

• Henzl MR: Norgestimate. From the laboratory to three clinical indications. J Reprod Med. 2001 Jul;46(7):647-61. Pubmed

• Goa KL, Warner GT, Easthope SE: Transdermal ethinylestradiol/norelgestromin: a review of its use in hormonal contraception. Treat Endocrinol. 2003;2(3):191-206. Pubmed

References

Bioactivity

PubChem BioAssay

Bioactivity

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General Information

Calculated Properties

• RDKit

• JChem

• ALOGPS 2.1

Data Source

• Academic Data