21-Deoxycortisol

21-Deoxycortisol
Names
	IUPAC name (8S,9S,10R,11S,13S,14S,17R)-17-acetyl-11,17-dihydroxy-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one
	Other names 21-Desoxycortisol; 21-Dehydrohydrocortisone; 21-Deoxyhydrocortisone; 11β,17α-Dihydroxyprogesterone; 11β,17α-Dihydroxypregn-4-ene-3,20-dione
Identifiers
CAS Number	641-77-0;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL1527439;
ChemSpider	83796;
KEGG	C05497;
PubChem CID	92827;
CompTox Dashboard (EPA)	DTXSID101044501 ;
	InChI InChI=1S/C21H30O4/c1-12(22)21(25)9-7-16-15-5-4-13-10-14(23)6-8-19(13,2)18(15)17(24)11-20(16,21)3/h10,15-18,24-25H,4-9,11H2,1-3H3/t15-,16-,17-,18+,19-,20-,21-/m0/s1 Key: LCZBQMKVFQNSJR-UJPCIWJBSA-N;
	SMILES CC(=O)[C@]1(CC[C@@H]2[C@@]1(C[C@@H]([C@H]3[C@H]2CCC4=CC(=O)CC[C@]34C)O)C)O;
Properties
Chemical formula	C21H30O4
Molar mass	346.467 g/mol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

21-Deoxycortisol, also known as 11β,17α-dihydroxyprogesterone or as 11β,17α-dihydroxypregn-4-ene-3,20-dione, is a naturally occurring, endogenous steroid related to cortisol (11β,17α,21-trihydroxyprogesterone) which is formed as a metabolite from 17α-hydroxyprogesterone via 11β-hydroxylase.^[1] It is a marker of congenital adrenal hyperplasia due to 21-hydroxylase deficiency.^[1] The corticosteroid activity of 21-deoxycortisol is virtually abolished relative to that of cortisol.^[2]

As 21-Deoxycortisol can be a high levels in congenital adrenal hyperplasia, and it has structural similarity to cortisol it can cross-react in immunoassays^[3]^[4], resulting in a falsely normal or high cortisol result, when the true cortisol is actually low.

References

^ ^a ^b Cristoni S, Cuccato D, Sciannamblo M, Bernardi LR, Biunno I, Gerthoux P, Russo G, Weber G, Mora S (2004). "Analysis of 21-deoxycortisol, a marker of congenital adrenal hyperplasia, in blood by atmospheric pressure chemical ionization and electrospray ionization using multiple reaction monitoring". Rapid Commun. Mass Spectrom. 18 (1): 77–82. doi:10.1002/rcm.1284. PMID 14689562.
^ P. J. Bentley (1980). Endocrine Pharmacology: Physiological Basis and Therapeutic Applications. CUP Archive. pp. 158–. ISBN 978-0-521-22673-8.
^ Winter WE, Bazydlo L, Harris NS (2012). "Cortisol - Clinical Indications and Laboratory Testing". AACC Clinical Laboratory News.
^ Krasowski MD, Drees D, Morris CS, Maakestad J, Blau JL, Ekins S (2014). "Cross-reactivity of steroid hormone immunoassays: clinical significance and two-dimensional molecular similarity prediction". BMC Clinical Pathology. 14 (33). PMID 25071417.

External links

Metabocard for 21-Deoxycortisol (HMDB04030) - Human Metabolome Database

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[pmid14689562-1] Cristoni S, Cuccato D, Sciannamblo M, Bernardi LR, Biunno I, Gerthoux P, Russo G, Weber G, Mora S (2004). "Analysis of 21-deoxycortisol, a marker of congenital adrenal hyperplasia, in blood by atmospheric pressure chemical ionization and electrospray ionization using multiple reaction monitoring". Rapid Commun. Mass Spectrom. 18 (1): 77–82. doi:10.1002/rcm.1284. PMID 14689562.

[Bentley1980-2] P. J. Bentley (1980). Endocrine Pharmacology: Physiological Basis and Therapeutic Applications. CUP Archive. pp. 158–. ISBN 978-0-521-22673-8.

[aacc1-3] Winter WE, Bazydlo L, Harris NS (2012). "Cortisol - Clinical Indications and Laboratory Testing". AACC Clinical Laboratory News.

[pmid25071417-4] Krasowski MD, Drees D, Morris CS, Maakestad J, Blau JL, Ekins S (2014). "Cross-reactivity of steroid hormone immunoassays: clinical significance and two-dimensional molecular similarity prediction". BMC Clinical Pathology. 14 (33). PMID 25071417.

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[2]

[3]

[4]

See also

References

External links