17-alpha-Hydroxyprogesterone

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[http://172.141.127.22/raghava/hmrbase/test_extract.php?db=arun&table=nphormonet&id=1004&show=SHOW-3D Show 3-D Structure]
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{{Drugbox
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| IUPAC_name        = (8R,9S,10R,13S,14S,17R)-17-acetyl-17-hydroxy-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one
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| CAS_number        = 68-96-2
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| CAS_supplemental  =
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| ATC_suffix = BA03
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| ATC_supplemental  =
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| PubChem          = 6238
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| ChemSpiderID      =
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| chemical_formula  =C<sub>2</sub><sub>1</sub>H<sub>3</sub><sub>0</sub>O<sub>3</sub>
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| molecular_weight  = 330.46
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| smiles            = CC(=O)C1(CCC2C1(CCC3C2CCC4=CC(=O)CCC34C)C)O
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| synonyms          =
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| density          =
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| melting_point    = 222-223
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| boiling_point    =
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| solubility        = 6.48(EXP) at 27C
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| specific_rotation =
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| sec_combustion    =
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| bioavailability  =
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| protein_bound    =
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| metabolism        = Liver
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| elimination_half-life =
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| excretion        =
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| pregnancy_category=
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| dependency_liability =
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| routes_of_administration = Intramuscular
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}}
==Description==
==Description==
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A metabolite of PROGESTERONE with a hydroxyl group at the 17-alpha  position. It serves as an intermediate in the biosynthesis of   HYDROCORTISONE and GONADAL STEROID HORMONES.
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'''17-Hydroxyprogesterone''' ('''17-OH progesterone''' or '''17OHP''') is a C-21 [[steroid hormone]] produced during the synthesis of [[glucocorticoid]]s and [[sex steroid]]s.
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As a hormone, 17OHP also interacts with the [[progesterone receptor]].  
==General Properties==
==General Properties==
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6.48(EXP) at 27C
6.48(EXP) at 27C
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==Production==
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It is derived from [[progesterone]] via [[17-hydroxylase]], a [[Cytochrome P450 oxidase|P450c17 enzyme]], or from [[17-hydroxypregnenolone]] via 3β-hydroxysteroid dehydrogenase/<sup>5-4</sup> isomerase.
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17-Hydroxyprogesterone is a natural progestin, and in pregnancy increases in the third trimester primarily due to fetal adrenal production.
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This hormone is primarily produced in the [[adrenal gland]]s and to some degree in the [[gonad]]s, specifically the [[corpus luteum]] of the [[ovary]]. Normal levels are 3-90 ng/dl in children, and in women, 15-70 ng/dl prior to [[ovulation]], and 35-290 ng/dl during the [[luteal phase]].
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==17-hydroxyprogesterone caproate==
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17-Hydroxyprogesterone is not the same compound as 17-hydroxyprogesterone [[caproate]]. 17-Hydroxyprogesterone caproate is a synthetic (artificial) hormone that is similar in structure to [[medroxyprogesterone acetate]] and [[megestrol acetate]].
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The terminology is confusing because 17P is used to refer to both the natural hormone and the artificial/synthetic hormone. It is preferable to refer to the synthetic hormone as 17-OHPC.
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The use of 17-hydroxyprogesterone caproate in pregnancy to prevent preterm birth is not recommended without further study according to two authorities. A 2006 Cochrane Review concluded "...important maternal and infant outcomes have been poorly reported to date... information regarding the potential harms of progesterone therapy to prevent preterm birth is limited".<ref> Dodd JM, Flenady V, Cincotta R, Crowther CA; The Cochrane Database of Systematic Reviews 2006 Issue 1</ref> There was a similar conclusion from a review by Marc Keirse.<ref>Keirse MJNC. Progesterone and Preterm: Seventy Years of "Deja vu" or "Still To Be Seen"?. Birth, 2004 September; 31:3.</ref> Three clinical studies of 250 mg/week of i.m. 17-hydroxyprogesterone caproate have all shown a trend for an increase in pregnancy loss due to miscarriage compared to placebo.<ref>Johnson JWC, Austin KL, Jones GS, Davis GH, King TM. Efficacy of 17 alpha-hydroxyprogesterone caproate in the prevention of premature labor. NEJM 1975 October. 293(14):675.</ref><ref>Yemini M, Borenstein R, Dreazen, et al. Prevention of premature labor by 17 alpha-hydroxyprogesterone caproate. Am J Obstet Gynecol. 1985;151(5):574-7. </ref><ref>Meis PJ et al. Prevention of Recurrent Preterm Delivery by 17 Alpha-hydroxyprogesterone Caproate. NEJM, 2003: vol 348, no 24, pg 2379-2385.</ref><ref>Keirse MJNC, Progestogen administration in pregnancy may prevent preterm delivery. Br J Obstet Gynecol 1990 February; 97:149.</ref> There has also been a study in rhesus monkeys in which all rhesus fetuses exposed to 1 and 10 times the human dose equivalent of 17-hydroxyprogesterone caproate died in utero.<ref>Hendrix AG, et al. Embriotoxicity of sex steroidal hormones in nonhuman primates: II. Hydroxyprogesterone caproate, estradiol valerate. Teratology 1987 February. 35 (1): 129.</ref> Currently, 17-hydroxyprogesterone caproate is a category D progestin according to the FDA (evidence of fetal harm). There is speculation that the castor oil in the 17-hydroxyprogesterone caproate formulation may not be beneficial for pregnancy.<ref>Duke University Medical Center, New England Journal of Medicine, correspondence, vol 349.</ref><ref>Hauth JC, Gilstrap LC, Brekken AL, Hauth JM. The effect of 17 alpha-hydroxyprogesterone caproate on pregnancy outcome in an active-duty military population. Am J Obstet Gynecol. 1983 May; 146(2): 187.</ref>
==External Links==
==External Links==
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*[http://www.genome.jp/dbget-bin/www_bget?compound+C01176]]KEGG Compound
*[http://www.genome.jp/dbget-bin/www_bget?compound+C01176]]KEGG Compound
*[http://www.hmdb.ca/metabolites/HMDB00374]Human Metabolome DataBase
*[http://www.hmdb.ca/metabolites/HMDB00374]Human Metabolome DataBase
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*[http://redpoll.pharmacy.ualberta.ca/~aguo/www_hmdb_ca/HMDB/scripts/CCMD_HTML.cgi?METABOCARD=HMDB00374 Chemical database at ualberta.ca]
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[[Category:Hormones]]
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[[Categories:Hormones]]
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[[Category:Progestagens]]
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[[Category:Steroids]]

Current revision

Show 3-D Structure

17-alpha-Hydroxyprogesterone
Systematic (IUPAC) name
(8R,9S,10R,13S,14S,17R)-17-acetyl-17-hydroxy-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one
Identifiers
CAS number 68-96-2
ATC code  ?
PubChem 6238
Chemical data
Formula C21H30O3
Mol. mass 330.46
SMILES eMolecules & PubChem
Physical data
Melt. point 222-223 °C
Solubility in water 6.48(EXP) at 27C mg/mL
Pharmacokinetic data
Bioavailability  ?
Metabolism Liver
Half life  ?
Excretion  ?
Therapeutic considerations
Pregnancy cat.

?

Legal status
Routes Intramuscular

Contents

[edit] Description

17-Hydroxyprogesterone (17-OH progesterone or 17OHP) is a C-21 steroid hormone produced during the synthesis of glucocorticoids and sex steroids.

As a hormone, 17OHP also interacts with the progesterone receptor.

[edit] General Properties

*Molecular Weight

330.46

*Molecular Formula

C21H30O3

*IUPAC NAME

(8R,9S,10R,13S,14S,17R)-17-acetyl-17-hydroxy-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one

*Canonical Smiles

CC(=O)C1(CCC2C1(CCC3C2CCC4=CC(=O)CCC34C)C)O

*Isomeric Smiles

CC(=O)[C@]1(CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=CC(=O)CC[C@]34C)C)O


[edit] PhysioChemical Properties

*Melting Point

222-223(EXP)

*LogP

3.17(EXP)

*Water Solubility

6.48(EXP) at 27C

[edit] Production

It is derived from progesterone via 17-hydroxylase, a P450c17 enzyme, or from 17-hydroxypregnenolone via 3β-hydroxysteroid dehydrogenase/5-4 isomerase.

17-Hydroxyprogesterone is a natural progestin, and in pregnancy increases in the third trimester primarily due to fetal adrenal production.

This hormone is primarily produced in the adrenal glands and to some degree in the gonads, specifically the corpus luteum of the ovary. Normal levels are 3-90 ng/dl in children, and in women, 15-70 ng/dl prior to ovulation, and 35-290 ng/dl during the luteal phase.

[edit] 17-hydroxyprogesterone caproate

17-Hydroxyprogesterone is not the same compound as 17-hydroxyprogesterone caproate. 17-Hydroxyprogesterone caproate is a synthetic (artificial) hormone that is similar in structure to medroxyprogesterone acetate and megestrol acetate.

The terminology is confusing because 17P is used to refer to both the natural hormone and the artificial/synthetic hormone. It is preferable to refer to the synthetic hormone as 17-OHPC.


The use of 17-hydroxyprogesterone caproate in pregnancy to prevent preterm birth is not recommended without further study according to two authorities. A 2006 Cochrane Review concluded "...important maternal and infant outcomes have been poorly reported to date... information regarding the potential harms of progesterone therapy to prevent preterm birth is limited".<ref> Dodd JM, Flenady V, Cincotta R, Crowther CA; The Cochrane Database of Systematic Reviews 2006 Issue 1</ref> There was a similar conclusion from a review by Marc Keirse.<ref>Keirse MJNC. Progesterone and Preterm: Seventy Years of "Deja vu" or "Still To Be Seen"?. Birth, 2004 September; 31:3.</ref> Three clinical studies of 250 mg/week of i.m. 17-hydroxyprogesterone caproate have all shown a trend for an increase in pregnancy loss due to miscarriage compared to placebo.<ref>Johnson JWC, Austin KL, Jones GS, Davis GH, King TM. Efficacy of 17 alpha-hydroxyprogesterone caproate in the prevention of premature labor. NEJM 1975 October. 293(14):675.</ref><ref>Yemini M, Borenstein R, Dreazen, et al. Prevention of premature labor by 17 alpha-hydroxyprogesterone caproate. Am J Obstet Gynecol. 1985;151(5):574-7. </ref><ref>Meis PJ et al. Prevention of Recurrent Preterm Delivery by 17 Alpha-hydroxyprogesterone Caproate. NEJM, 2003: vol 348, no 24, pg 2379-2385.</ref><ref>Keirse MJNC, Progestogen administration in pregnancy may prevent preterm delivery. Br J Obstet Gynecol 1990 February; 97:149.</ref> There has also been a study in rhesus monkeys in which all rhesus fetuses exposed to 1 and 10 times the human dose equivalent of 17-hydroxyprogesterone caproate died in utero.<ref>Hendrix AG, et al. Embriotoxicity of sex steroidal hormones in nonhuman primates: II. Hydroxyprogesterone caproate, estradiol valerate. Teratology 1987 February. 35 (1): 129.</ref> Currently, 17-hydroxyprogesterone caproate is a category D progestin according to the FDA (evidence of fetal harm). There is speculation that the castor oil in the 17-hydroxyprogesterone caproate formulation may not be beneficial for pregnancy.<ref>Duke University Medical Center, New England Journal of Medicine, correspondence, vol 349.</ref><ref>Hauth JC, Gilstrap LC, Brekken AL, Hauth JM. The effect of 17 alpha-hydroxyprogesterone caproate on pregnancy outcome in an active-duty military population. Am J Obstet Gynecol. 1983 May; 146(2): 187.</ref>

[edit] External Links

Retrieved from "http://277988.efsst.group/drugpedia/index.php/17-alpha-Hydroxyprogesterone"