WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H462802
CAS#: 516-15-4
Description: 11-Ketoprogesterone is a pregnane steroid related to cortisone that was formerly used in veterinary medicine in the treatment of bovine ketosis. The steroid has profound effects on carbohydrate metabolism and possesses activities associated with adrenal cortex hormones like cortisone. However, it is non-toxic even in high dosages, suggesting that it lacks conventional glucocorticoid activity, and it does not possess mineralocorticoid activity, unlike other adrenocortical hormones. 11-Ketoprogesterone may act through membrane glucocorticoid receptors.
Hodoodo Cat#: H462802
Name: 11-Ketoprogesterone
CAS#: 516-15-4
Chemical Formula: C21H28O3
Exact Mass: 328.20
Molecular Weight: 328.452
Elemental Analysis: C, 76.79; H, 8.59; O, 14.61
This product is not in stock, which may be available by custom synthesis.
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Synonym: Ketogestin; Ketoprogesterone;
IUPAC/Chemical Name: (8S,9S,10R,13S,14S,17S)-17-acetyl-10,13-dimethyl-1,6,7,8,9,10,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthrene-3,11(2H)-dione
InChi Key: WKAVAGKRWFGIEA-DADBAOPHSA-N
InChi Code: InChI=1S/C21H28O3/c1-12(22)16-6-7-17-15-5-4-13-10-14(23)8-9-20(13,2)19(15)18(24)11-21(16,17)3/h10,15-17,19H,4-9,11H2,1-3H3/t15-,16+,17-,19+,20-,21+/m0/s1
SMILES Code: CC([C@H]1CC[C@H]2[C@@H]3CCC4=CC(CC[C@@]4([C@H]3C(C[C@]12C)=O)C)=O)=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
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: 2934.99.9001
More Info:
| Biological target: | |
| In vitro activity: | |
| In vivo activity: |
The following data is based on the product molecular weight 328.45 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 |
| Formulation protocol: | |
| In vitro protocol: | |
| In vivo protocol: |
1: van Rooyen D, Gent R, Barnard L, Swart AC. The in vitro metabolism of 11β-hydroxyprogesterone and 11-ketoprogesterone to 11-ketodihydrotestosterone in the backdoor pathway. J Steroid Biochem Mol Biol. 2018 Apr;178:203-212. doi: 10.1016/j.jsbmb.2017.12.014. Epub 2017 Dec 23. PMID: 29277707.
2: du Toit T, Finken MJJ, Hamer HM, Heijboer AC, Swart AC. C11-oxy C19 and C11-oxy C21 steroids in neonates: UPC2-MS/MS quantification of plasma 11β-hydroxyandrostenedione, 11-ketotestosterone and 11-ketoprogesterone. Steroids. 2018 Oct;138:1-5. doi: 10.1016/j.steroids.2018.06.003. Epub 2018 Jun 6. PMID: 29883615.
3: Gent R, du Toit T, Bloem LM, Swart AC. The 11β-hydroxysteroid dehydrogenase isoforms: pivotal catalytic activities yield potent C11-oxy C19 steroids with 11βHSD2 favouring 11-ketotestosterone, 11-ketoandrostenedione and 11-ketoprogesterone biosynthesis. J Steroid Biochem Mol Biol. 2019 May;189:116-126. doi: 10.1016/j.jsbmb.2019.02.013. Epub 2019 Feb 27. PMID: 30825506.
4: Galigniana MD, Vicent GP, Burton G, Lantos CP. Features of the shuttle pair 11 beta-hydroxyprogesterone-11-ketoprogesterone. Steroids. 1997 Apr;62(4):358-64. doi: 10.1016/s0039-128x(96)00244-9. PMID: 9090796.
5: OERTEL GW, EIK-NES KB. Isolation and identification of 11-ketoprogesterone, 11-hydroxyprogesterone and 11-hydroxyandrostenedione in canine adrenal vein blood. Endocrinology. 1962 Jan;70:39-42. doi: 10.1210/endo-70-1-39. PMID: 14481175.
6: Das S, Dutta TK, Samanta TB. Influence of substituents at C11 on hydroxylation of progesterone analogs by Bacillus sp. J Steroid Biochem Mol Biol. 2002 Oct;82(2-3):257-61. doi: 10.1016/s0960-0760(02)00156-5. PMID: 12477493.
7: INGLE DJ, BEARY DF, PURMALIS A. Comparison of the effect of 11-ketoprogesterone, 11alpha-hydroxyprogesterone and 11 beta-hydroxyprogesterone upon the glycosuria of the partially depancreatized rat. Endocrinology. 1953 Aug;53(2):221-5. doi: 10.1210/endo-53-2-221. PMID: 13068348.
8: van Rooyen D, Yadav R, Scott EE, Swart AC. CYP17A1 exhibits 17αhydroxylase/17,20-lyase activity towards 11β-hydroxyprogesterone and 11-ketoprogesterone metabolites in the C11-oxy backdoor pathway. J Steroid Biochem Mol Biol. 2020 May;199:105614. doi: 10.1016/j.jsbmb.2020.105614. Epub 2020 Jan 30. PMID: 32007561.
9: JONSSON U, COLSKY J, LESSNER HE, ROATH OS, ALPER RG, JONES R Jr. Clinical and pharmacological observations of the effects of 9-alpha-bromo-11-beta- ketoprogesterone in patients with carcinoma of the breast. Cancer. 1959 May- Jun;12(3):509-20. doi: 10.1002/1097-0142(195905/06)12:3<509::aid- cncr2820120310>3.0.co;2-t. PMID: 13652098.
10: Torday JS, Post M, Smith BT. Compartmentalization of 11-oxidoreductase within fetal lung alveolus. Am J Physiol. 1985 Jul;249(1 Pt 1):C173-6. doi: 10.1152/ajpcell.1985.249.1.C173. PMID: 3860015.
11: INGLE DJ, BEARY DF, PURMALIS A. Comparison of effect of progesterone and 11-ketoprogesterone upon glycosuria of partially depancreatized rat. Proc Soc Exp Biol Med. 1953 Mar;82(3):416-9. doi: 10.3181/00379727-82-20133. PMID: 13047418.
12: SPEICHER JA, SHAW JC, CHUNG AC, GESSERT RA. Studies on ketosis in dairy cattle. XVIII. The value of 11-ketoprogesterone as a therapeutic agent. J Am Vet Med Assoc. 1955 Sep;127(942):218-9. PMID: 13251945.
13: WIED GL, DAVIS ME. 9 alpha-Bromo-11-ketoprogesterone; another new orally effective substance with progestational activity. Obstet Gynecol. 1957 Oct;10(4):411-7. PMID: 13477602.
14: DUFF IF, ROBINSON WD, WOLFSON WQ. Clinical trial of 11-ketoprogesterone in rheumatoid arthritis. J Mich State Med Soc. 1952 Sep;51(9):1176-82. PMID: 13000340.
15: GOLDENBERG IS, HAYES MA. Hormonal therapy of metastatic female breast carcinoma. I. 9 alpha-Bromo-11-ketoprogesterone. Cancer. 1959 Jul- Aug;12(4):738-40. doi: 10.1002/1097-0142(195907/08)12:4<738::aid- cncr2820120418>3.0.co;2-m. PMID: 13663018.
16: Smith BT. The role of pulmonary corticosteroid 11-reductase activity in lung maturation in the fetal rat. Pediatr Res. 1978 Jan;12(1):12-4. doi: 10.1203/00006450-197801000-00004. PMID: 643369.
17: Zhong Y, Simmonds MA. Pharmacological characterisation of multiple components in the enhancement by pregnanolone and propofol of [3H]flunitrazepam binding to GABAA receptors. Neuropharmacology. 1996;35(9-10):1193-8. doi: 10.1016/s0028-3908(96)00056-1. PMID: 9014134.
18: Gent R, du Toit T, Swart AC. 11α-Hydroxyprogesterone, a potent 11β-hydroxysteroid dehydrogenase inhibitor, is metabolised by steroid-5α-reductase and cytochrome P450 17α-hydroxylase/17,20-lyase to produce C11α-derivatives of 21-deoxycortisol and 11-hydroxyandrostenedione in vitro. J Steroid Biochem Mol Biol. 2019 Jul;191:105369. doi: 10.1016/j.jsbmb.2019.04.018. Epub 2019 Apr 27. PMID: 31039398.
19: Dangi B, Kim KH, Kang SH, Oh TJ. Tracking Down a New Steroid-Hydroxylating Promiscuous Cytochrome P450: CYP154C8 from Streptomyces sp. W2233-SM. Chembiochem. 2018 May 18;19(10):1066-1077. doi: 10.1002/cbic.201800018. Epub 2018 Apr 25. PMID: 29512903.
20: Burton G, Galigniana M, De Lavallaz S, Brachet-Cota AL, Sproviero EM, Ghini AA, Lantos CP, Damasco MC. Sodium-retaining activity of some natural and synthetic 21-deoxysteroids. Mol Pharmacol. 1995 Mar;47(3):535-43. PMID: 7700251.
