Synonym
Retroprogesterone;
IUPAC/Chemical Name
(8S,9R,10S,13S,14S,17S)-17-acetyl-10,13-dimethyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-3H-cyclopenta[a]phenanthren-3-one
InChi Key
RJKFOVLPORLFTN-HQZYFCCVSA-N
InChi Code
InChI=1S/C21H30O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h12,16-19H,4-11H2,1-3H3/t16-,17+,18-,19+,20+,21+/m0/s1
SMILES Code
CC([C@H]1CC[C@@]2([H])[C@]3([H])CCC4=CC(CC[C@@]4(C)[C@]3([H])CC[C@]12C)=O)=O
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
Shelf Life
>3 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
2934.99.03.00
Preparing Stock Solutions
The following data is based on the
product
molecular weight
314.46
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 |
1: AYDAR CK, GREENBLATT RB. 6-DEHYDRO-RETROPROGESTERONE (DUPHASTON) AN INTERESTING PROGESTERONE-LIKE COMPOUND. Int J Fertil. 1964 Oct-Dec;9:585-95. PubMed PMID: 14215356.
2: Rižner TL, Brožič P, Doucette C, Turek-Etienne T, Müller-Vieira U, Sonneveld E, van der Burg B, Böcker C, Husen B. Selectivity and potency of the retroprogesterone dydrogesterone in vitro. Steroids. 2011 May;76(6):607-15. doi: 10.1016/j.steroids.2011.02.043. Epub 2011 Mar 3. PubMed PMID: 21376746.
3: Strecker JR. [Treatment of the premenstrual syndrome with a retroprogesterone (Duphaston)]. Fortschr Med. 1980 Jan 31;98(4):(145-7). German. PubMed PMID: 7189174.
4: Schindler AE, Campagnoli C, Druckmann R, Huber J, Pasqualini JR, Schweppe KW, Thijssen JH. Classification and pharmacology of progestins. Maturitas. 2003 Dec 10;46 Suppl 1:S7-S16. Review. PubMed PMID: 14670641.
5: Presl J. [Retroprogesterone and its derivatives--further possibilities for stimulation of ovulation in the woman]. Cesk Gynekol. 1972 Sep;37(7):539-41. Czech. PubMed PMID: 5077990.
6: Stamm O, Gerhard I, Zarro D. [Treatment of endocrine sterility with retroprogesterone Ro 4-8347]. Bull Schweiz Akad Med Wiss. 1970 Oct;25(4-6):472-80. German. PubMed PMID: 5279914.
7: Weber HP, Galantay E. The molecular and crystal structure of psi-retroprogesterone. Helv Chim Acta. 1974;57(1):187-92. PubMed PMID: 4465336.
8: Yaoi Y, Bettendorf G. [Influence of retroprogesterone, clomid, and sexovid on the gonadotropin releasing factor activity in the hypothalamus of rats]. Acta Endocrinol Suppl (Copenh). 1971;152:1. German. PubMed PMID: 4927548.
9: Mistò A. [Experiences with 6-dehydro-retroprogesterone int the treatment of placental insufficiency]. Ann Ostet Ginecol Med Perinat. 1967 Feb;89(2):102-12. Italian. PubMed PMID: 5601176.
10: Sugawa H, Moriyama I, Kakita M. [Action of delta-6-retroprogesterone (Duphaston) on DNA synthesis of the uterine endometrium]. Horumon To Rinsho. 1969 Oct;17(10):876-7. Japanese. PubMed PMID: 5390549.
11: Okada H, Hayashi H, Yamamoto H, Sumi M, Ichihara M. [Metabolism of 6-dehydro-retroprogesterone in rabbits]. Nihon Naibunpi Gakkai Zasshi. 1968 Apr 20;44(1):15-8. Japanese. PubMed PMID: 5692638.
12: Jamain M, Grenet C. [Utilization of 6-dehydro-retroprogesterone in obstetrics: indications; results]. Bull Fed Soc Gynecol Obstet Lang Fr. 1969 Jan-Mar;21(1):26-31. French. PubMed PMID: 5383875.
13: Taubert HD, Jürgensen O. The treatment of monophasic cycles with the retroprogesterone Ro 4-8347. Bull Schweiz Akad Med Wiss. 1970 Oct;25(4-6):503-11. PubMed PMID: 4251825.
14: Polishuk WZ, Laufer A, Schechter A. Cytological and endometrial effects of retroprogesterone Ro 4-8347. Bull Schweiz Akad Med Wiss. 1970 Oct;25(4-6):466-71. PubMed PMID: 5510173.
15: Stamm O, Zarro D, Gerhard I. [Stimulation of the LH excretion by retroprogesterone Ro 4-8347]. Bull Schweiz Akad Med Wiss. 1970 Oct;25(4-6):391-407. German. PubMed PMID: 5534328.
16: SUREAU C, COMBOURIEU P. [CLINICAL STUDY OF 6-DEHYDRO-RETROPROGESTERONE (DYDROGESTERONE)]. Bull Fed Soc Gynecol Obstet Lang Fr. 1964 Jun-Aug;16:263-9. French. PubMed PMID: 14204366.
17: Hauser GA. [Use of retroprogesterone]. Ther Umsch. 1970 Oct;27(10):709-10. German. PubMed PMID: 5512729.
18: Scommegna A, Rao R, Dmowski WP. Clinical trials with IUDs releasing retroprogesterone. Contracept Deliv Syst. 1980 Jan;1(1):21-6. PubMed PMID: 12261714.
19: Yaoi Y, Kuwabara S, Bettendorf G. [FSH and LH releasing activity of retroprogesterone, sexovide, clomide and catecholamines in castrated estrogen-progesterone-blocked rats]. Arch Gynakol. 1971 Jun 4;211(1):210-1. German. PubMed PMID: 5108849.
20: Kalra PS, Martini L. The facilitatory' effect on ovulation of the retrosteroid 1,6-dehydro-6-chloro-retroprogesterone (Ro 4-8347). J Endocrinol. 1971 Dec;51(4):675-83. PubMed PMID: 4109612.
