Progesterone (abbreviatit as P4), an aa kent as pregn-4-ene-3,20-dione,[13][14] is an endogenous steroid an progestogen sex hormone involved in the menstrual cycle, pregnancy, an embryogenesis o humans an ither species.[15]

Progesterone
The chemical structur o progesterone.
A baw-an-stick model o progesterone.
Names
IUPAC name
(8S,9S,10R,13S,14S,17S)-17-acetyl-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
Ither names
P4;[1] Pregn-4-ene-3,20-dione[2][3]
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.000.318
KEGG
UNII
Properties
C21H30O2
Molar mass 314.469 g/mol
Meltin pynt 126
log P 4.04[4]
Pharmacology
G03DA04 (WHO)
Bi mooth, topical/transdermal, vaginal, intramuscular injection, subcutaneous injection, subcutaneous implant
Pharmacokinetics:
OMP: <10%[5][6]
Albumin: 80%
CBG: 18%
SHBG: <1%
• Free: 1–2%[7][8]
Hepatic (CYP2C19, CYP3A4, CYP2C9, 5α-reductase, 3α-HSD, 17α-hydroxylase, 21-hydroxylase, 20α-HSD)[9][10]
OMP: 16–18 oors[5][6][11]
IM: 22–26 oors[6][12]
SC: 13–18 oors[12]
Renal
Except whaur itherwise notit, data are gien for materials in thair staundart state (at 25 °C [77 °F], 100 kPa).
YesY verify (whit is YesYN ?)
Infobox references

ReferencesEedit

  1. Jameson JL, De Groot LJ (25 February 2015). Endocrinology: Adult and Pediatric E-Book. Elsevier Health Sciences. p. 2179. ISBN 978-0-323-32195-2.
  2. Adler N, Pfaff D, Goy RW (6 Dec 2012). Handbook of Behavioral Neurobiology Volume 7 Reproduction (1st ed.). New York: Plenum Press. p. 189. ISBN 978-1-4684-4834-4. Retrieved 4 July 2015.
  3. "progesterone (CHEBI:17026)". ChEBI. European Molecular Biology Laboratory-EBI. Retrieved 4 July 2015.
  4. "Progesterone_msds".
  5. 5.0 5.1 Stanczyk FZ (September 2002). "Pharmacokinetics and potency of progestins used for hormone replacement therapy and contraception". Reviews in Endocrine & Metabolic Disorders. 3 (3): 211–24. doi:10.1023/A:1020072325818. PMID 12215716.
  6. 6.0 6.1 6.2 Simon JA, Robinson DE, Andrews MC, Hildebrand JR, Rocci ML, Blake RE, Hodgen GD (July 1993). "The absorption of oral micronized progesterone: the effect of food, dose proportionality, and comparison with intramuscular progesterone". Fertility and Sterility. 60 (1): 26–33. doi:10.1016/S0015-0282(16)56031-2. PMID 8513955.
  7. Fritz MA, Speroff L (28 March 2012). Clinical Gynecologic Endocrinology and Infertility. Lippincott Williams & Wilkins. pp. 44–. ISBN 978-1-4511-4847-3.
  8. Marshall WJ, Marshall WJ, Bangert SK (2008). Clinical Chemistry. Elsevier Health Sciences. pp. 192–. ISBN 978-0-7234-3455-9.
  9. Yamazaki H, Shimada T (October 1997). "Progesterone and testosterone hydroxylation by cytochromes P450 2C19, 2C9, and 3A4 in human liver microsomes". Archives of Biochemistry and Biophysics. 346 (1): 161–9. doi:10.1006/abbi.1997.0302. PMID 9328296.
  10. McKay GA, Walters MR (6 February 2013). Lecture Notes: Clinical Pharmacology and Therapeutics. John Wiley & Sons. p. 33. ISBN 978-1-118-34489-7.
  11. Zutshi (1 January 2005). Hormones in Obstetrics and Gynaecology. Jaypee Brothers Publishers. p. 74. ISBN 978-81-8061-427-9.
  12. 12.0 12.1 Cometti B (November 2015). "Pharmaceutical and clinical development of a novel progesterone formulation". Acta Obstetricia et Gynecologica Scandinavica. 94 (Suppl 161): 28–37. doi:10.1111/aogs.12765. PMID 26342177.
  13. Norman Adler; Donald Pfaff; Robert W. Goy (6 Dec 2012). Handbook of Behavioral Neurobiology Volume 7 Reproduction (1st ed.). New York: Plenum Press. p. 189. ISBN 978-1-4684-4834-4. Retrieved 4 July 2015.
  14. "progesterone (CHEBI:17026)". ChEBI. European Molecular Biology Laboratory-EBI. Retrieved 4 July 2015.
  15. Tekoa L. King; Mary C. Brucker (25 October 2010). Pharmacology for Women's Health. Jones & Bartlett Publishers. pp. 372–373. ISBN 978-1-4496-5800-7.