Compounds > 16-dehydroprogesterone
Page last updated: 2024-12-07

16-dehydroprogesterone

## 16-Dehydroprogesterone: A key player in steroid hormone research

**16-Dehydroprogesterone (16-DHP)** is a naturally occurring steroid hormone with a unique structure. It's a derivative of progesterone, but with a double bond at the C16 position. This seemingly small change has significant implications for its biological activity and its role in research.

**Here's what makes 16-DHP important for research:**

**1. Potential therapeutic applications:**

* **Anti-inflammatory and immunomodulatory effects:** Studies suggest that 16-DHP may have anti-inflammatory properties, potentially useful for treating autoimmune disorders and inflammatory conditions. Its ability to modulate immune responses also makes it an intriguing target for research in areas like transplantation and allergy.
* **Anti-cancer activity:** Preclinical research indicates that 16-DHP might exhibit anti-cancer activity, particularly against certain types of breast cancer and leukemia. Its mechanism of action is still under investigation, but it appears to interfere with cell growth and proliferation.
* **Neuroprotective effects:** 16-DHP has shown promise in protecting neurons from damage, potentially leading to treatments for neurodegenerative diseases like Alzheimer's and Parkinson's.

**2. Understanding steroid hormone metabolism:**

* **Metabolic pathway insights:** 16-DHP is an intermediate in the metabolic pathway of progesterone, making it crucial for studying the synthesis and breakdown of this important hormone. Understanding the conversion of progesterone to 16-DHP can provide valuable information about the regulation of hormone levels and potential therapeutic targets.
* **Exploring structural modifications:** Comparing the effects of 16-DHP with other progesterone derivatives allows researchers to pinpoint the specific functional groups responsible for its unique biological activity. This knowledge can help design novel, more potent and targeted therapeutic agents.

**3. Studying the role of steroid hormones in various biological processes:**

* **Reproductive health:** 16-DHP's influence on the reproductive system, particularly the menstrual cycle, is being actively investigated. Its role in fertility and other reproductive functions is a key area of research.
* **Hormonal regulation:** 16-DHP interacts with various steroid hormone receptors, influencing their activation and downstream signaling pathways. This makes it essential for understanding how steroid hormones regulate a wide range of bodily functions.

**Ongoing research:**

* **Developing novel drug candidates:** The potential therapeutic benefits of 16-DHP are driving research into its pharmacokinetic properties, identifying optimal dosage forms, and developing safe and effective drugs based on this molecule.
* **Exploring its mechanism of action:** Researchers are actively investigating the molecular targets and signaling pathways involved in the biological effects of 16-DHP. This information is crucial for understanding its therapeutic potential and developing targeted treatments.
* **Clinical trials:** Some early clinical trials are underway to assess the safety and efficacy of 16-DHP in treating specific diseases, such as certain cancers and inflammatory conditions.

**Overall, 16-dehydroprogesterone remains a fascinating area of study with significant implications for understanding steroid hormone metabolism, developing new therapeutic strategies, and improving human health.**

Cross-References

ID SourceID
PubMed CID101964
CHEBI ID18204
SCHEMBL ID4661581
MeSH IDM0090778

Synonyms (41)

Synonym
pregna-4,16-diene-3,20-dione
delta(4,16)-pregnadiene-3,20-dione
CHEBI:18204
3,20-dioxopregna-4,16-diene
pregna-4,20-dione
nsc-9785
nsc-11037
nsc9785
nsc11037
.delta.16-progesterone
3,16-diene
nsc 11037
.delta.4,20-dione
1096-38-4
C03207
16-dehydroprogesterone
16,17-didehydroprogesterone
16-dehydroprogesterone, 97%
LMST02030163
(8r,9s,10r,13s,14s)-17-acetyl-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15-decahydrocyclopenta[a]phenanthren-3-one
delta4,16-pregnadiene-3,20-dione
ju0yq9dz2o ,
einecs 214-142-8
nsc 9785
unii-ju0yq9dz2o
S6140
4,16-pregnadiene-3,20-dione
AKOS022172049
SCHEMBL4661581
.delta.4,16-pregnadiene-3,20-dione
delta.16-progesterone
d4,16-pregnadiene-3,20-dione
d16-progesterone
DS-6807
DTXSID10862535
Q27102899
CS-0099261
HY-128378
16-?dehydroprogesterone
16-ehydroprogesterone
PD124055
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (3)

ClassDescription
20-oxo steroidAn oxo steroid carrying an oxo group at position 20.
3-oxo-Delta(4) steroidA 3-oxo steroid conjugated to a C=C double bond at the alpha,beta position.
enoneAn alpha,beta-unsaturated ketone of general formula R(1)R(2)C=CR(3)-C(=O)R(4) (R(4) =/= H) in which the C=O function is conjugated to a C=C double bond at the alpha,beta position.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Research

Studies (8)

TimeframeStudies, This Drug (%)All Drugs %
pre-19904 (50.00)18.7374
1990's2 (25.00)18.2507
2000's1 (12.50)29.6817
2010's1 (12.50)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.13

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index12.13 (24.57)
Research Supply Index2.20 (2.92)
Research Growth Index4.32 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.13)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies1 (12.50%)4.05%
Observational0 (0.00%)0.25%
Other7 (87.50%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
hydrogen
Hydrogen: The first chemical element in the periodic table with atomic symbol H, and atomic number 1. Protium (atomic weight 1) is by far the most common hydrogen isotope. Hydrogen also exists as the stable isotope DEUTERIUM (atomic weight 2) and the radioactive isotope TRITIUM (atomic weight 3). Hydrogen forms into a diatomic molecule at room temperature and appears as a highly flammable colorless and odorless gas.. dihydrogen : An elemental molecule consisting of two hydrogens joined by a single bond.		6.9610elemental hydrogen;
elemental molecule;
gas molecular entity		antioxidant;
electron donor;
food packaging gas;
fuel;
human metabolite
pyruvic acid
Pyruvic Acid: An intermediate compound in the metabolism of carbohydrates, proteins, and fats. In thiamine deficiency, its oxidation is retarded and it accumulates in the tissues, especially in nervous structures. (From Stedman, 26th ed). pyruvic acid : A 2-oxo monocarboxylic acid that is the 2-keto derivative of propionic acid. It is a metabolite obtained during glycolysis.		1.96102-oxo monocarboxylic acidcofactor;
fundamental metabolite
dihydrotestosterone
Dihydrotestosterone: A potent androgenic metabolite of TESTOSTERONE. It is produced by the action of the enzyme 3-OXO-5-ALPHA-STEROID 4-DEHYDROGENASE.. 17beta-hydroxyandrostan-3-one : A 17beta-hydroxy steroid that is testosterone in which the 4-5 double bond has been reduced to a single bond with unspecified configuration at position 5.. 17beta-hydroxy-5alpha-androstan-3-one : A 17beta-hydroxy steroid that is testosterone in which the 4,5 double bond has been reduced to a single bond with alpha-configuration at position 5.		1.971017beta-hydroxy steroid;
17beta-hydroxyandrostan-3-one;
3-oxo-5alpha-steroid		androgen;
Daphnia magna metabolite;
human metabolite;
mouse metabolite
pregnanolone
Pregnanolone: A pregnane found in the urine of pregnant women and sows. It has anesthetic, hypnotic, and sedative properties.. 3alpha-hydroxy-5beta-pregnan-20-one : The 3alpha-stereoisomer of 3-hydroxy-5beta-pregnan-20-one.		1.95103-hydroxy-5beta-pregnan-20-one;
3alpha-hydroxy steroid		human metabolite;
intravenous anaesthetic;
sedative
androstan-3-one
[no description available]		6.9710
16-hydroxyprogesterone
16-hydroxyprogesterone: RN given refers to unlabeled cpd without isomeric designation		1.9610corticosteroid hormone
ouabain
Ouabain: A cardioactive glycoside consisting of rhamnose and ouabagenin, obtained from the seeds of Strophanthus gratus and other plants of the Apocynaceae; used like DIGITALIS. It is commonly used in cell biological studies as an inhibitor of the NA(+)-K(+)-EXCHANGING ATPASE.. cardiac glycoside : Steroid lactones containing sugar residues that act on the contractile force of the cardiac muscles.. ouabain : A steroid hormone that is a multi-hydroxylated alpha-L-rhamnosyl cardenoloide. It binds to and inhibits the plasma membrane Na(+)/K(+)-ATPase (sodium pump). It has been isolated naturally from Strophanthus gratus.		6.971011alpha-hydroxy steroid;
14beta-hydroxy steroid;
5beta-hydroxy steroid;
alpha-L-rhamnoside;
cardenolide glycoside;
steroid hormone		anti-arrhythmia drug;
cardiotonic drug;
EC 2.3.3.1 [citrate (Si)-synthase] inhibitor;
EC 3.1.3.41 (4-nitrophenylphosphatase) inhibitor;
EC 3.6.3.10 (H(+)/K(+)-exchanging ATPase) inhibitor;
EC 3.6.3.9 (Na(+)/K(+)-transporting ATPase) inhibitor;
ion transport inhibitor;
plant metabolite
cysteine
Cysteine: A thiol-containing non-essential amino acid that is oxidized to form CYSTINE.. L-cysteinium : The L-enantiomer of cysteinium.. cysteine : A sulfur-containing amino acid that is propanoic acid with an amino group at position 2 and a sulfanyl group at position 3.		1.9610cysteiniumfundamental metabolite
pregna-4,17-diene-3,16-dione
pregna-4,17-diene-3,16-dione: steroid from guggulu extract; RN & N1 from C1 Form index; RN given refers to cpd without isomeric designation; structure in first source; antagonist of farnesoid X receptor		2.02103-hydroxy steroidandrogen
heme
Heme: The color-furnishing portion of hemoglobin. It is found free in tissues and as the prosthetic group in many hemeproteins.. ferroheme : Any iron(II)--porphyrin coordination complex.. ferroheme b : Heme b in which the iron has oxidation state +2.. heme : A heme is any tetrapyrrolic chelate of iron.		1.9610
ConditionIndicatedRelationship StrengthStudiesTrials
Breast Cancer
[description not available]		02.1710
Breast Neoplasms
Tumors or cancer of the human BREAST.		02.1710
Granulocytic Leukemia
[description not available]		02.0210
Acute Disease
Disease having a short and relatively severe course.		02.0210
Leukemia, Myeloid
Form of leukemia characterized by an uncontrolled proliferation of the myeloid lineage and their precursors (MYELOID PROGENITOR CELLS) in the bone marrow and other sites.		02.0210
Clerambault Syndrome
[description not available]		01.9810
Premenstrual Tension
A term used to describe the psychological aspects of PREMENSTRUAL SYNDROME, such as the indescribable tension, depression, hostility, and increased seizure activity in women with seizure disorder.		01.9810
Premenstrual Syndrome
A combination of distressing physical, psychologic, or behavioral changes that occur during the luteal phase of the menstrual cycle. Symptoms of PMS are diverse (such as pain, water-retention, anxiety, cravings, and depression) and they diminish markedly 2 or 3 days after the initiation of menses.		01.9810
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