17-alpha-Hydroxyprogesterone
From DrugPedia: A Wikipedia for Drug discovery
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| 17-alpha-Hydroxyprogesterone
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| 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 | |
| ATC code | ? |
| PubChem | |
| Chemical data | |
| Formula | C21H30O3 |
| Mol. mass | 330.46 |
| SMILES | & |
| 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
- [1]Pubchem
- [2]]KEGG Compound
- [3]Human Metabolome DataBase
- Chemical database at ualberta.ca
