(1S,2R,5S,10R,11S,14R,15S)-5-(acetyloxy)-14-ethynyl-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-14-yl acetate

• ChemBase ID: 702
• Molecular Formular: C24H32O4
• Molecular Mass: 384.50848
• Monoisotopic Mass: 384.2300595
• SMILES: O([C@@]1([C@@]2([C@H]([C@H]3[C@H](CC2)[C@@H]2C(=C[C@@H](OC(=O)C)CC2)CC3)CC1)C)C#C)C(=O)C
• Canonical SMILES: C#C[C@@]1(CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CCC2=C[C@H](CC[C@H]12)OC(=O)C)OC(=O)C
• InChI: InChI=1S/C24H32O4/c1-5-24(28-16(3)26)13-11-22-21-8-6-17-14-18(27-15(2)25)7-9-19(17)20(21)10-12-23(22,24)4/h1,14,18-22H,6-13H2,2-4H3/t18-,19-,20+,21+,22-,23-,24-/m0/s1
• InChIKey: ONKUMRGIYFNPJW-KIEAKMPYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,5S,10R,11S,14R,15S)-5-(acetyloxy)-14-ethynyl-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-14-yl acetate; (1S,2R,5S,10R,11S,14R,15S)-5-(acetyloxy)-14-ethynyl-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-14-yl acetate
• IUPAC Traditional name: ethynodiol diacetate
• Brand Name: Cervicundin; Continuin; Femulen; Luteonorm; Luto-Metrodiol; Metrodiol; Metrodiol Diacetate; Metrulen; Ovulen; Ovulen 50
• Synonyms: 3β,17β-Diacetoxy-17α-ethynyl-4-estrene; Ethynodiol diacetate; Ethinodiol Diacetate; Ethynodiol; Etynodiol; Ethynodiol Diacetate; Etynodiol diacetate

Database IDs

• CAS Number: 297-76-7
• EC Number: 206-044-9
• MDL Number: MFCD00083326
• PubChem SID: 46506993; 24894643; 160964165
• PubChem CID: 92709270; 9270
• ATC CODE: G03FA06; G03DC06; G03AA01
• Chemspider ID: 8913
• DrugBank ID: DB00823
• Wikipedia Title: Etynodiol_diacetate

CALCULATED PROPERTIES

JChem

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 3.6881402
• LogD (pH = 7.4): 3.6881402
• Log P: 3.6881402
• Molar Refractivity: 106.6249 cm^3
• Polarizability: 42.21005 Å^3
• Polar Surface Area: 52.6 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.99
• LOG S: -4.99
• Solubility (Water): 3.97e-03 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): 5

Safety Information

• RTECS: RC8963000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 20/21/22-40
• Safety Statements: 22-36
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H312-H332-H351
• GHS Precautionary statements: P280
• Personal Protective Equipment: Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges

Pharmacology Properties

• Admin Routes: Oral
• Legal Status: Rx-only

DETAILS

DrugBank - DB00823

• Drug Groups: approved
• Description: A synthetic progestational hormone used alone or in combination with estrogens as an oral contraceptive. [PubChem]
• Indication: For the prevention of pregnancy in women who elect to use this product as a method of contraception.
• Pharmacology: Ethynodiol Diacetate is used as a female contraceptive. Ethynodiol Diacetate is a progestin or a synthetic form of the naturally occurring female sex hormone, progesterone. In a woman's normal menstrual cycle, an egg matures and is released from the ovaries (ovulation). The ovary then produces progesterone, preventing the release of further eggs and priming the lining of the womb for a possible pregnancy. If pregnancy occurs, progesterone levels in the body remain high, maintaining the womb lining. If pregnancy does not occur, progesterone levels in the body fall, resulting in a menstrual period. Ethynodiol Diacetate tricks the body processes into thinking that ovulation has already occurred, by maintaining high levels of the synthetic progesterone. This prevents the release of eggs from the ovaries.
• Affected Organisms: Humans and other mammals
• Protein Binding: 50-85%
• External Links: Wikipedia; RxList