11beta-Hydroxyprogesterone

Names

[ CAS No. ]:
600-57-7

[ Name ]:
11beta-Hydroxyprogesterone

[Synonym ]:
11BETA-HYDROXYPROGESTERONE
4-PREGNEN-11BETA-OL-3,20-DIONE
21-deoxycorticosterone
11B-HYDROXYPROGESTERONE
HYDROXYPROGESTERONE,11B
11beta-hydroxyprogesterone
4-PREGNEN-11BETA-3,20-DIONE

Biological Activity

[Description]:

11beta-Hydroxyprogesterone is a potent inhibitors of 11β-Hydroxysteroid dehydrogenase; also activates human mineralocorticoid receptor in COS-7 cells with an ED50 of 10 nM.

[Related Catalog]:

Natural Products >> Steroids

Research Areas >> Cardiovascular Disease

[Target]

Human Endogenous Metabolite

[In Vitro]

11OHP displays agonist mineralocorticoid activity. 11β-hydroxyprogesterone activates the transiently expressed hMR in COS-7 cells in a dose-dependent manner with an ED50 of 10 nM and stimulates Ams/sc in mpkCCDcl4 cells. Docking 11β-hydroxyprogesterone within the hMR-ligand-binding domain homology model reveals that the agonist activity of 11OHP is caused by contacts between its 11β-hydroxyl group and Asn770[1].

[In Vivo]

11β-hydroxyprogesterone causes a significant elevation in blood pressure within 3 days, an effect that persisted throughout the 14-day infusion. 11β-hydroxyprogesterone is potently hypertensinogenic in the rat and that this activity depends on an intact adrenal and at least in part on the activation of mineralocorticoid receptors[2].

[Animal admin]

Rats: 11α- and 11β-OHP are dissolved in propylene glycol (100%) and infused at 3 and 10 μg/h, respectively, for 14 days. Control rats received vehicle only. BP is measured the day before pumps were implanted and on days 3, 7, 10, and 14 after implantation. Indirect systolic BPs are measured with a modified tail-cuff method[2].

[References]

[1]. Rafestin-Oblin ME, et al. 11beta-hydroxyprogesterone acts as a mineralocorticoid agonist in stimulating Na+ absorption in mammalian principal cortical collecting duct cells. Mol Pharmacol. 2002 Dec;62(6):1306-13.

[2]. Souness GW, et al. 11 alpha- and 11 beta-hydroxyprogesterone, potent inhibitors of 11 beta-hydroxysteroid dehydrogenase, possess hypertensinogenic activity in the rat. Hypertension. 1996 Mar;27(3 Pt 1):421-5.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.15g/cm3

[ Boiling Point ]:
487.4ºC at 760 mmHg

[ Molecular Formula ]:
C₂₁H₃₀O₃

[ Molecular Weight ]:
330.46100

[ Flash Point ]:
262.7ºC

[ Exact Mass ]:
330.21900

[ PSA ]:
54.37000

[ LogP ]:
3.69430

[ Index of Refraction ]:
1.557

[ Storage condition ]:
-20°C

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: TU5058000

CHEMICAL NAME :: Pregn-4-ene-3,20-dione, 11-beta-hydroxy-

CAS REGISTRY NUMBER :: 600-57-7

LAST UPDATED :: 199709

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C21-H30-O3

MOLECULAR WEIGHT :: 330.51

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Parenteral

DOSE :: 28 mg/kg

SEX/DURATION :: female 28 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Maternal Effects - uterus, cervix, vagina

REFERENCE :: JEMEAV Journal of Experimental Medicine. (Rockefeller Univ. Press, 1230 York Ave., New York, NY 10021) V.1- 1896- Volume(issue)/page/year: 102,347,1955

11beta-Hydroxyprogesterone

Names

Biological Activity

Chemical & Physical Properties

Toxicological Information

CHEMICAL IDENTIFICATION

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Related Compounds