Ethynodiol Diacetate
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Hodoodo CAT#: H317853

CAS#: 297-76-7 (diacetate)

Description: Etynodiol diacetate is a steroidal progestin which is used as a hormonal contraceptive. Relative to other 19-nortestosterone derivatives, it has relatively little or no potency as an androgen, and, unlike most progestins but similarly to noretynodrel, also has some estrogenic effects.

Chemical Structure

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Ethynodiol Diacetate
CAS# 297-76-7 (diacetate)
Instruction

Theoretical Analysis

Hodoodo Cat#: H317853
Name: Ethynodiol Diacetate
CAS#: 297-76-7 (diacetate)
Chemical Formula: C24H32O4
Exact Mass: 384.23
Molecular Weight: 384.509
Elemental Analysis: C, 74.97; H, 8.39; O, 16.64

Price and Availability

Size Price Availability Quantity
1g USD 320 2 weeks
2g USD 550 2 weeks
5g USD 1050 2 weeks
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Related CAS #: 1231-93-2 (free base)   297-76-7 (diacetate)  

Synonym: Ethynodiol Diacetate, Continuin, Femulen, Luteonorm, Luto-Metrodiol, Metrodiol, norethindrol diacetate, ethynodiol diacetate

IUPAC/Chemical Name: (3S,8R,9S,10R,13S,14S,17R)-17-ethynyl-13-methyl-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,17-diyl diacetate

InChi Key: ONKUMRGIYFNPJW-KIEAKMPYSA-N

InChi Code: 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

SMILES Code: CC(O[C@H]1CC[C@@H]2[C@H]3CC[C@@]4(C)[C@@H](CC[C@@]4(OC(C)=O)C#C)[C@@H]3CCC2=C1)=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:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 384.51 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.

Recalculate based on batch purity %
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:
In vitro protocol:
In vivo protocol:

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1: Zafar S, Yousuf S, Kayani HA, Saifullah, Khan S, Al-Majid AM, Choudhary MI. Biotransformation of oral contraceptive ethynodiol diacetate with microbial and plant cell cultures. Chem Cent J. 2012 Sep 29;6(1):109. doi: 10.1186/1752-153X-6-109. PubMed PMID: 23021311; PubMed Central PMCID: PMC3496622.

2: Siddique YH, Ara G, Beg T, Afzal M. Protective role of nordihydroguaiaretic acid (NDGA) against the genotoxic damage induced by ethynodiol diacetate in human lymphocytes in vitro. J Environ Biol. 2007 Apr;28(2):279-82. PubMed PMID: 17915765.

3: Babják M, Balogh G, Gazdag M, Görög S. Estimation of impurity profiles of drugs and related materials: part XXI. HPLC/UV/MS study of the impurity profile of ethynodiol diacetate. J Pharm Biomed Anal. 2002 Aug 1;29(6):1153-7. PubMed PMID: 12110402.

4: Simic B, Kniewald J, Kniewald Z. Influence of Ethynodiol Diacetate on the Formation of A-Homo-3Oxa-5?-Pregnane-4,20-Dione in Female Rats. Endocr Regul. 1998 Sep;32(3):125-131. PubMed PMID: 10196509.

5: Friedman AJ, Wheeler JM. Incidence of ovarian cyst formation in women taking ethynodiol diacetate, 1 mg, with ethinyl estradiol, 35 micrograms. J Reprod Med. 1991 Apr;36(4 Suppl):345-9. PubMed PMID: 2046084.

6: Wheeler JM, Malinak LR. Complexion changes in oral contraceptive users. Results from a phase IV multicenter trial evaluating the safety and efficacy of ethynodiol diacetate, 1 mg, with ethinyl estradiol, 35 micrograms. J Reprod Med. 1991 Apr;36(4 Suppl):340-4. PubMed PMID: 2046083.

7: Friedman AJ, Wheeler J. Efficacy and safety of ethynodiol diacetate, 1 mg, with ethinyl estradiol, 35 micrograms, with an emphasis on contraceptive efficacy. A phase IV trial. J Reprod Med. 1991 Apr;36(4 Suppl):328-33. PubMed PMID: 2046081.

8: Friedman AJ. Safety and efficacy of ethynodiol diacetate, 1 mg, plus ethinyl estradiol, 35 micrograms. A phase IV trial. Introduction. J Reprod Med. 1991 Apr;36(4 Suppl):323-4. PubMed PMID: 2046079.

9: Görög S, Halmos Z, Herényi B, Georgakis A, Balogh G, Csizér E, Tuba Z. [Analysis of steroids. Part 40. Isolation and identification of unusual impurities in ethynodiol diacetate]. Acta Pharm Hung. 1991 Mar;61(2):77-81. Hungarian. PubMed PMID: 1887802.

10: Shroff NE, Pearce MY, Stratford ME, Wilkinson PD. Clinical experience with ethynodiol diacetate 0.5 mg daily as an oral contraceptive. Contraception. 1987 Feb;35(2):121-34. PubMed PMID: 3297483.

11: Cooke ID, Back DJ, Shroff NE. Norethisterone concentration in breast milk and infant and maternal plasma during ethynodiol diacetate administration. Contraception. 1985 Jun;31(6):611-21. PubMed PMID: 4042659.

12: Morvay J, Altorjay I, Sas M. Saliva level of ethynylestradiol in presence of ethynodiol diacetate after oral administration. Horm Res. 1983;17(4):181-4. PubMed PMID: 6884982.

13: Morvay J, Altorjay I, Sas M. Serum and placenta levels of ethynylestradiol in presence of ethynodiol diacetate after oral administration. Horm Res. 1982 Jul-Aug;16(4):237-43. PubMed PMID: 6890038.

14: Carignan G, Lodge BA, Skakum W. Quantitative analysis of ethynodiol diacetate and ethinyl estradiol/mestranol in oral contraceptive tablets by high-performance liquid chromatography. J Pharm Sci. 1982 Feb;71(2):264-6. PubMed PMID: 7062257.

15: Lewis CJ, Vose CW, Spalton PN, Ford GC, Haskins NJ, Palmer RF. Metabolism of ethynodiol diacetate in the rhesus monkey before and after administration of rifampicin. Xenobiotica. 1980 Sep;10(9):705-13. PubMed PMID: 7445531.

16: Ethynodiol diacetate. IARC Monogr Eval Carcinog Risk Chem Hum. 1979 Dec;21:387-98. PubMed PMID: 120836.

17: Vose CW, Butler JK, Williams BM, Stafford JE, Shelton JR, Rose DA, Palmer RF, Breckenridge AM, Orme ML, Serlin MJ. Bioavailability and pharmacokinetics of norethisterone in women after oral doses of ethynodiol diacetate. Contraception. 1979 Feb;19(2):119-27. PubMed PMID: 428229.

18: Higashiyama S. [Biological activities of 3 different types of ethynodiol diacetate-ethynyl estradiol combinations (author's transl)]. Nihon Funin Gakkai Zasshi. 1978 Oct;23(4):414-20. Japanese. PubMed PMID: 710724.

19: Drill VA, Golway PL. Effect of ethynodiol diacetate with ethinyl estradiol on the mammary glands of rhesus monkeys: a preliminary report. J Natl Cancer Inst. 1978 May;60(5):1169-70. PubMed PMID: 417188.

20: Goldman JA. Effect of ethynodiol diacetate and a combination-type oral contraceptive compound on carbohydrate metabolism. II. One year intravenous glucose tolerance study. Diabetologia. 1977 Apr;13(2):89-91. PubMed PMID: 856654.