STR

PROGESTERONE

Created: 1999-07-08
Last modified:  2011-06-04

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Chemical Details

Formal Charge0
Atom Count53
Chiral Atom Count6
Bond Count56
Aromatic Bond Count0
2D diagram of STR
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Chemical Component Summary

NamePROGESTERONE
Systematic Name (OpenEye OEToolkits)(8S,9S,10R,13S,14S,17S)-17-ethanoyl-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
FormulaC21 H30 O2
Molecular Weight314.462
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESACDLabs10.04O=C4C=C2C(C1CCC3(C(C(=O)C)CCC3C1CC2)C)(C)CC4
SMILESCACTVS3.341CC(=O)[CH]1CC[CH]2[CH]3CCC4=CC(=O)CC[C]4(C)[CH]3CC[C]12C
SMILESOpenEye OEToolkits1.5.0CC(=O)C1CCC2C1(CCC3C2CCC4=CC(=O)CCC34C)C
Canonical SMILESCACTVS3.341 CC(=O)[C@H]1CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C
Canonical SMILESOpenEye OEToolkits1.5.0 CC(=O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=CC(=O)CC[C@]34C)C
InChIInChI1.03 InChI=1S/C21H30O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h12,16-19H,4-11H2,1-3H3/t16-,17+,18-,19-,20-,21+/m0/s1
InChIKeyInChI1.03 RJKFOVLPORLFTN-LEKSSAKUSA-N

Drug Info: DrugBank

DrugBank IDDB00396 
NameProgesterone
Groups
  • approved
  • vet_approved
DescriptionProgesterone is a hormone that occurs naturally in females, and is essential for endometrial receptivity, embryo implantation, and the successful establishment of pregnancy. A low progesterone concentration or an insufficient response to progesterone can cause infertility and pregnancy loss [A175609]. Progesterone is used in various contraceptive preparations to prevent ovulation and fertilization [T481], [A175612] as well as in other formulations to promote and support pregnancy. Please see [Medroxyprogesterone acetate], [Megestrol acetate], [Dydrogesterone] and [Hydroxyprogesterone] entries for information on various other forms of progesterone. Pharmaceutical progesterone is made from a plant source as a starting material and is chemically identical to progesterone of human ovarian origin [FDA label]. Progesterone is available in gelatinized capsule form, vaginal gel form, tablet form, vaginal insert form, and injection form, all used for various purposes [Label,F3898,F3904,F3901,F3907].
Synonyms
  • Progesterona
  • Progesteron
  • 17alpha-Progesterone
  • Luteohormone
  • delta(4)-Pregnene-3,20-dione
Brand Names
  • P50 Progesterone Cream
  • P25 Progesterone Cream
  • Progesterone Inj 50mg/ml USP
  • Minoxidil 7% / Progesterone 0.1%
  • Minoxidil 7% / Progesterone 0.1% / Tretinoin 0.025%
Indication**Gelatinized capsules** The gelatinized capsules are indicated for use in the prevention of endometrial hyperplasia in non-hysterectomized postmenopausal women who are receiving conjugated estrogens tablets. They are also indicated for use in secondary amenorrhea [FDA label]. **Vaginal gel** Progesterone gel (8%) is indicated as progesterone supplementation or replacement as part of an Assisted Reproductive Technology (“ART”) treatment for infertile women with progesterone deficiency. The lower concentration progesterone gel (4%) is used in the treatment of secondary amenorrhea, with the use of the 8% concentration if there is no therapeutic response to the 4% gel [F3898]. **Vaginal insert** This form is indicated to support embryo implantation and early pregnancy by supplementation of corpus luteal function as part of an Assisted Reproductive Technology (ART) treatment program for infertile women [F3901]. **Injection (intramuscular)** This drug is indicated in amenorrhea and abnormal uterine bleeding due to hormonal imbalance in the absence of organic pathology, such as submucous fibroids or uterine cancer [F3907]. **Tablets, contraceptive** The tablet form of progesterone in contraceptive formulations is indicated for the prevention of pregnancy [F3904].
Categories
  • Adrenal Cortex Hormones
  • BCRP/ABCG2 Inducers
  • BCRP/ABCG2 Inhibitors
  • BSEP/ABCB11 Inhibitors
  • Corpus Luteum Hormones
ATC-Code
  • G03FA04
  • G03DA04
CAS number57-83-0

Drug Targets

NameTarget SequencePharmacological ActionActions
Progesterone receptorMTELKAKGPRAPHVAGGPPSPEVGSPLLCRPAAGPFPGSQTSDTLPEVSA...unknownagonist
Mineralocorticoid receptorMETKGYHSLPEGLDMERRWGQVSQAVERSSLGPTERTDENNYMEIVNVSC...unknownantagonist,agonist
Estrogen receptor alphaMTMTLHTKASGMALLHQIQGNELEPLNRPQLKIPLERPLGEVYLDSSKPA...unknownagonist,inhibitor,downregulator
Steroid 17-alpha-hydroxylase/17,20 lyaseMWELVALLLLTLAYLFWPKRRCPGAKYPKSLLSLPLVGSLPFLPRHGHMH...unknownsubstrate,inhibitor
Kappa-type opioid receptorMDSPIQIFRGEPGPTCAPSACLPPNSSAWFPGWAEPDSNGSAGSEDAQLE...unknownactivator,potentiator
View More
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
Pharos CHEMBL103
PubChem 5994
ChEMBL CHEMBL103
ChEBI CHEBI:17026
CCDC/CSD PROGST12, XUGWUU, PROGST13, PROGST10, CUSZOG, CUSZIA, YUKQAZ, PROGST14, CUSZIA01, KOSQER, PROGST11, CUSZEW, CUSZUM, CUSZAS, CUSYOF, KEFBEC, CUSYUL, TIPMAH, PRORES, KOSNUE, KESBEQ, XUNCIV
COD 4511761, 7101588