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;
ChEBI	CHEBI:28697;
ChEMBL	ChEMBL1527439;
ChemSpider	83796;
KEGG	C05497;
PubChem CID	92827;
UNII	XZ1JYU14MZ ;
	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

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. Bibcode:2004RCMS...18...77C. 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). doi:10.1186/1472-6890-14-33. PMC 4112981. 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. Bibcode:2004RCMS...18...77C. 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). doi:10.1186/1472-6890-14-33. PMC 4112981. PMID 25071417.

21-Deoxycortisol

See also

References

External links