ContaminantDB: Progesterone

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (29)XML

Record Information

Version

1.0

Creation Date

2014-08-29 06:01:46 UTC

Update Date

2026-04-17 17:48:11 UTC

Accession Number

CHEM003204

Identification

Common Name

Progesterone

Class

Small Molecule

Description

The major progestational steroid that is secreted primarily by the corpus luteum and the placenta. Progesterone acts on the uterus, the mammary glands and the brain. It is required in embryo implantation, pregnancy maintenance, and the development of mammary tissue for milk production. Progesterone, converted from pregnenolone, also serves as an intermediate in the biosynthesis of gonadal steroid hormones and adrenal corticosteroids. Progesterone is a C-21 steroid hormone involved in the female menstrual cycle, pregnancy (supports gestation) and embryogenesis of humans and other species. Progesterone belongs to a class of hormones called progestagens, and is the major naturally occurring human progestagen. During implantation and gestation, progesterone appears to decrease the maternal immune response to allow for the acceptance of the pregnancy. Progesterone decreases contractility of the uterine smooth muscle. The fetus metabolizes placental progesterone in the production of adrenal mineralo- and glucosteroids. A drop in progesterone levels is possibly one step that facilitates the onset of labor. In addition progesterone inhibits lactation during pregnancy. The fall in progesterone levels following delivery is one of the triggers for milk production.

Contaminant Sources

Cosmetic Chemicals
FooDB Chemicals
IARC Carcinogens Group 2B
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Animal Toxin
Contraceptive Agent
Drug
Ester
Food Toxin
Metabolite
Natural Compound
Organic Compound
Progestin

Chemical Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
(S)-4-Pregnene-3,20-dione	ChEBI
(S)-Pregn-4-en-3,20-dione	ChEBI
(S)-Progesterone	ChEBI
17alpha-Progesterone	ChEBI
4-Pregnene-3,20-dione	ChEBI
Agolutin	ChEBI
Akrolutin	ChEBI
Corpus luteum hormone	ChEBI
Crinone	ChEBI
Delta(4)-Pregnene-3,20-dione	ChEBI
Gelbkoerperhormon	ChEBI
Luteohormone	ChEBI
Progesteron	ChEBI
Prometrium	Kegg
17a-Progesterone	Generator
17Α-progesterone	Generator
Δ(4)-pregnene-3,20-dione	Generator
3,20-Pregnene-4	HMDB
4-Pregnen-3,20-dione	HMDB
beta-Progesterone	HMDB
Bio-luton	HMDB
CIDR	HMDB
Colprosterone	HMDB
Corlutin	HMDB
Corlutina	HMDB
Corluvite	HMDB
Corporin	HMDB
Crinone progesterone gel	HMDB
Curretab	HMDB
Cyclogest	HMDB
Cyclogesterin	HMDB
D4-Pregnene-3,20-dione	HMDB
Delalutin	HMDB
Duraprogen	HMDB
Estima	HMDB
Flavolutan	HMDB
Fologenon	HMDB
Gesterol	HMDB
Gesterol 100	HMDB
Gesterol 50	HMDB
Gestiron	HMDB
Gestone	HMDB
Gestormone	HMDB
Gestron	HMDB
Glanducorpin	HMDB
Gynlutin	HMDB
Gynoluton	HMDB
Gynolutone	HMDB
Hormoflaveine	HMDB
Hormoluton	HMDB
Hydroxyprogesterone caproate	HMDB
Hydroxyprogesterone caproic acid	HMDB
Lingusorbs	HMDB
Lipo-lutin	HMDB
Lucorteum	HMDB
Lucorteum sol	HMDB
Lugesteron	HMDB
Luteal hormone	HMDB
Luteocrin normale	HMDB
Luteodyn	HMDB
Luteogan	HMDB
Luteol	HMDB
Luteopur	HMDB
Luteosan	HMDB
Luteostab	HMDB
Luteovis	HMDB
Luteum	HMDB
Lutex	HMDB
Lutidon	HMDB
Lutociclina	HMDB
Lutocuclin m	HMDB
Lutocyclin	HMDB
Lutocyclin m	HMDB
Lutocylin	HMDB
Lutocylol	HMDB
Lutoform	HMDB
Lutogyl	HMDB
Lutren	HMDB
Lutromone	HMDB
Membrettes	HMDB
Methylpregnone	HMDB
MPA	HMDB
Nalutron	HMDB
Percutacrine	HMDB
Percutacrine luteinique	HMDB
Piaponon	HMDB
Pranone	HMDB
Pregn-4-en-3,20-dione	HMDB
Pregn-4-ene-3,20-dione	HMDB
Pregnene-3,20-dione	HMDB
Pregnenedione	HMDB
Primolut	HMDB
Prochieve	HMDB
Progeffik	HMDB
Progekan	HMDB
Progestan	HMDB
Progestasert	HMDB
Progesterol	HMDB
Progesteronum	HMDB
Progestin	HMDB
Progestogel	HMDB
Progestol	HMDB
Progeston	HMDB
Progestone	HMDB
Progestosol	HMDB
Progestron	HMDB
Progestronol	HMDB
Projestaject	HMDB
Prolets	HMDB
Prolidon	HMDB
Prolutin	HMDB
Proluton	HMDB
Prolutone	HMDB
Prontogest	HMDB
Protormone	HMDB
Syngesterone	HMDB
Syngestrets	HMDB
Synovex S	HMDB
Syntolutan	HMDB
Utrogest	HMDB
Utrogestan	HMDB
Vitarrine	HMDB
Progesterone, (13 alpha,17 alpha)-(+-)-isomer	HMDB
Progesterone, (17 alpha)-isomer	HMDB
Progesterone, (9 beta,10 alpha)-isomer	HMDB

Chemical Formula

C₂₁H₃₀O₂

Average Molecular Mass

314.462 g/mol

Monoisotopic Mass

314.225 g/mol

CAS Registry Number

57-83-0

IUPAC Name

(1S,2R,10S,11S,14S,15S)-14-acetyl-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one

Traditional Name

(1S,2R,10S,11S,14S,15S)-14-acetyl-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one

SMILES

[H][C@@]12CC[C@H](C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C

InChI Identifier

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

InChI Key

RJKFOVLPORLFTN-LEKSSAKUSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Pregnane steroids

Direct Parent

Gluco/mineralocorticoids, progestogins and derivatives

Alternative Parents

Substituents

Progestogin-skeleton
20-oxosteroid
Oxosteroid
3-oxosteroid
3-oxo-delta-4-steroid
Delta-4-steroid
Cyclohexenone
Cyclic ketone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

3-oxo Delta(4)-steroid (CHEBI:17026 )
20-oxo steroid (CHEBI:17026 )
C21-steroid hormone (CHEBI:17026 )
Pregnane and derivatives [Fig] (C00410 )
Progestagens (C00410 )
C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030159 )

Biological Properties

Status

Detected and Not Quantified

Origin

Endogenous

Cellular Locations

Cytoplasm
Endoplasmic reticulum
Extracellular
Membrane

Biofluid Locations

Not Available

Tissue Locations

Adipose Tissue
Fibroblasts
Gonads
Neuron
Placenta
Platelet
Prostate
Testes

Pathways

Name	SMPDB Link	KEGG Link
Steroidogenesis	SMP00130	map00140
17-alpha-hydroxylase deficiency (CYP17)	SMP00566	Not Available
Adrenal Hyperplasia Type 3 or Congenital Adrenal Hyperplasia due to 21-hydroxylase Deficiency	SMP00373	Not Available
Adrenal Hyperplasia Type 5 or Congenital Adrenal Hyperplasia due to 17 Alpha-hydroxylase Deficiency	SMP00372	Not Available

Applications

Biological Roles

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	121°C
Boiling Point	Not Available
Solubility	8.81 mg/L (at 25°C)

Predicted Properties

Property	Value	Source
Water Solubility	0.0055 g/L	ALOGPS
logP	3.58	ALOGPS
logP	4.15	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	18.92	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	34.14 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	92.71 m³·mol⁻¹	ChemAxon
Polarizability	37.26 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0fbc-5910000000-422e38df6de7e8b0a4b7	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0fbc-5910000000-385f45345742235da8e0	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-024l-6923000000-639c7405f69825de7f90	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0229-2941000000-1e075d8489b79cf4e34a	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0229-3963000000-f35e3d9faf6b2ee87465	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0fbc-5910000000-422e38df6de7e8b0a4b7	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0fbc-5910000000-385f45345742235da8e0	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0f6x-2910000000-1baafb91a3e0b988caa7	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-000g-1590000000-3ebb52b90c541e38c0b4	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-014i-1009000000-0f8b7c3e6c2265c3889f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-052b-8900000000-0b0167121b798e7e7534	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-052b-9400000000-881510cbcecd9cb61f4f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (JEOL JMS-01-SG-2) , Positive	splash10-024l-6923000000-639c7405f69825de7f90	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-52) , Positive	splash10-0229-2941000000-1e075d8489b79cf4e34a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-004i-0950000000-ca28d8dfdf780c201716	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-000i-1900000000-857f6720dd17fb2547d1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-004i-3930000000-fda87095285a83b85ad5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-00kb-7955000000-a22f06eac940cd4f753d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-014i-0139000000-6b47f75a44df3e20fa3b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0aba-0950000000-b26d04d179294aa67cc7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0aba-0920000000-d0a3365efe1f8a589564	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-05aj-0910000000-61d7a07e6be85600e1f1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-014i-0009000000-67c6f0147801f0ece957	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-05mk-8956000000-aa5fe992c41261b62fbf	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-052b-6910000000-5e26497eb2d0150a30ac	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0a4j-8900000000-7ca6fd15f0ccc18bfa31	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-052b-9700000000-523fe1ad11bfcbb46f85	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-054k-9400000000-e3d581bd8685e1d3f35d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0269000000-9aa25f8d44bc44ee4d4c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-06dj-0491000000-c312ac322a549be24fac	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0pbc-2290000000-859101eb546be9ddc938	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0019000000-e021f799bd2d232a0592	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0049000000-55066424591bf87a4a49	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0002-1090000000-e9387b8ab692f5ef9083	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-006x-7931000000-f6ad83adccd7e016fa29	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Progesterone absorption is prolonged with an absorption half-life of approximately 25-50 hours.

Mechanism of Toxicity

Progesterone shares the pharmacological actions of the progestins. Progesterone binds to the progesterone and estrogen receptors. Target cells include the female reproductive tract, the mammary gland, the hypothalamus, and the pituitary. Once bound to the receptor, progestins like Progesterone will slow the frequency of release of gonadotropin releasing hormone (GnRH) from the hypothalamus and blunt the pre-ovulatory LH (luteinizing hormone) surge. In women who have adequate endogenous estrogen, progesterone transforms a proliferative endometrium into a secretory one. Progesterone is essential for the development of decidual tissue and is necessary to increase endometrial receptivity for implantation of an embryo. Once an embryo has been implanted, progesterone acts to maintain the pregnancy. Progesterone also stimulates the growth of mammary alveolar tissue and relaxes uterine smooth muscle. It has little estrogenic and androgenic activity.

Metabolism

Progesterone is metabolized primarily by the liver largely to pregnanediols and pregnanolones. Route of Elimination: The glucuronide and sulfate conjugates of pregnanediol and pregnanolone are excreted in the urine and bile. Progesterone metabolites which are excreted in the bile may undergo enterohepatic recycling or may be excreted in the feces. Progesterone metabolites are excreted mainly by the kidneys. Half Life: 34.8-55.13 hours

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

2B, possibly carcinogenic to humans. (21)

Uses/Sources

For progesterone supplementation or replacement as part of an Assisted Reproductive Technology (ART) treatment for infertile women with progesterone deficiency and for the treatment of secondary amenorrhea. Also used for the reduction of the incidence of endometrial hyperplasia and the attendant risk of endometrial carcinoma in postmenopausal women receiving estrogen replacement therapy, as well as treatment of abnormal uterine bleeding due to hormonal imbalance in the absence of organic pathology such as fibroids or uterine cancer.

Minimum Risk Level

Not Available

Health Effects

Chronically high levels of progesterone are associated with at least 3 inborn errors of metabolism including: Congenital adrenal hyperplasia, Adrenal Hyperplasia Type 3 and Adrenal hyperplasia type 5.

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB00396

HMDB ID

HMDB0001830

FooDB ID

FDB001871

Phenol Explorer ID

Not Available

KNApSAcK ID

BiGG ID

BioCyc ID

METLIN ID

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

Not Available

ECMDB ID

M2MDB005073

References

Synthesis Reference

Nejib M. Nasraoui, Alain Piasco, “Derivatives of 19-nor progesterone; process for producing them and the pharmaceutical compositions incorporating them.” U.S. Patent US5223492, issued May, 1971.

MSDS

Link

General References

1. Vasquez, L.; Alarcon, J.; Zunza, H.; Becerra, J.; Silva, M. Chemical-microbiological synthesis of progesterone. Boletin de la Sociedad Chilena de Quimica (2001), 46(1), 29-31.

2. Narendran R, Hacker RR, Smith VG, Lun A: Estrogen and progesterone concentrations in bovine milk during the estrous cycle. Theriogenology. 1979 Jul;12(1):19-25.

3. Colazo MG, Ambrose DJ, Kastelic JP, Small JA: Comparison of 2 enzyme immunoassays and a radioimmunoassay for measurement of progesterone concentrations in bovine plasma, skim milk, and whole milk. Can J Vet Res. 2008 Jan;72(1):32-6.

4. Vasquez, L.; Alarcon, J.; Zunza, H.; Becerra, J.; Silva, M. Chemical-microbiological synthesis of progesterone. Boletin de la Sociedad Chilena de Quimica (2001), 46(1), 29-31.

5. Afsar NA, Barakzai Q, Adil SN: Effect of a 'progestin only' contraceptive on platelet aggregation in a Pakistani set of population. J Ayub Med Coll Abbottabad. 2005 Jul-Sep;17(3):21-5.

6. Moguilewsky M, Tournemine C: The antiandrogen anandron potentiates the castrating effect of the LH-RH agonist buserelin in the rat. Am J Clin Oncol. 1988;11 Suppl 2:S148-51.

7. Wang C, Swerdloff RS: Male hormonal contraception. Am J Obstet Gynecol. 2004 Apr;190(4 Suppl):S60-8.

8. Landi N, Manfredini D, Lombardi I, Casarosa E, Bosco M: 17-beta-estradiol and progesterone serum levels in temporomandibular disorder patients. Minerva Stomatol. 2004 Nov-Dec;53(11-12):651-60.

9. Classen-Linke I, Alfer J, Krusche CA, Chwalisz K, Rath W, Beier HM: Progestins, progesterone receptor modulators, and progesterone antagonists change VEGF release of endometrial cells in culture. Steroids. 2000 Oct-Nov;65(10-11):763-71.