NAV

Hydroxyprogesterone

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Generic Name
Hydroxyprogesterone
DrugBank Accession Number
DB14570
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 330.4611
Monoisotopic: 330.219494826
Chemical Formula
C21H30O3
Synonyms
  • 17-Hydroxypregn-4-en-3,20-dione
  • 17-hydroxyprogesterone
  • 17alpha-hydroxyprogesterone
  • 17α-hydroxyprogesterone
  • delta(4)-Pregnene-17alpha-ol-3,20-dione
  • Hidroxiprogesterona
  • Hydroxyprogesterone
  • Hydroxyprogesteronum
  • Pregn-4-ene-3,20-dione-17-ol
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
Not Available
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
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interactions in your software
AbametapirThe serum concentration of Hydroxyprogesterone can be increased when it is combined with Abametapir.
AbciximabHydroxyprogesterone may decrease the anticoagulant activities of Abciximab.
AcenocoumarolHydroxyprogesterone may decrease the anticoagulant activities of Acenocoumarol.
AlteplaseHydroxyprogesterone may decrease the anticoagulant activities of Alteplase.
AmiodaroneThe metabolism of Hydroxyprogesterone can be decreased when combined with Amiodarone.
Food Interactions
Not Available

Categories

ATC Codes
G03FA02 — Hydroxyprogesterone and estrogenG03DA03 — Hydroxyprogesterone
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound 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
20-oxosteroids / 3-oxo delta-4-steroids / 17-hydroxysteroids / Delta-4-steroids / Cyclohexenones / Tertiary alcohols / Alpha-hydroxy ketones / Cyclic alcohols and derivatives / Organic oxides / Hydrocarbon derivatives
Substituents
17-hydroxysteroid / 20-oxosteroid / 3-oxo-delta-4-steroid / 3-oxosteroid / Alcohol / Aliphatic homopolycyclic compound / Alpha-hydroxy ketone / Carbonyl group / Cyclic alcohol / Cyclic ketone
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
17alpha-hydroxy steroid (CHEBI:17252) / Progestagens (C01176) / C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030161)
Affected organisms
Not Available

Chemical Identifiers

UNII
21807M87J2
CAS number
68-96-2
InChI Key
DBPWSSGDRRHUNT-CEGNMAFCSA-N
InChI
InChI=1S/C21H30O3/c1-13(22)21(24)11-8-18-16-5-4-14-12-15(23)6-9-19(14,2)17(16)7-10-20(18,21)3/h12,16-18,24H,4-11H2,1-3H3/t16-,17+,18+,19+,20+,21+/m1/s1
IUPAC Name
(1R,3aS,3bR,9aR,9bS,11aS)-1-acetyl-1-hydroxy-9a,11a-dimethyl-1H,2H,3H,3aH,3bH,4H,5H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-one
SMILES
[H][C@@]12CC[C@](O)(C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C

References

General References
Not Available
Human Metabolome Database
HMDB0000374
KEGG Compound
C01176
ChemSpider
6002
BindingDB
50423511
RxNav
5542
ChEBI
17252
ChEMBL
CHEMBL1062
ZINC
ZINC000005434436
PDBe Ligand
3QZ
Wikipedia
17%CE%B1-Hydroxyprogesterone
PDB Entries
3qz1 / 4nky / 5ier / 5if6 / 5vbu

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount
4CompletedTreatmentPre-Eclampsia1
3CompletedPreventionAbsorption; Chemicals / Premature Births1
2CompletedSupportive CarePreterm Premature Rupture of Membranes (PPROM)1
1, 2CompletedTreatmentPregnancy, Complications1
1, 2TerminatedBasic SciencePremature Births1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0293 mg/mLALOGPS
logP2.99ALOGPS
logP3.4Chemaxon
logS-4ALOGPS
pKa (Strongest Acidic)12.7Chemaxon
pKa (Strongest Basic)-3.8Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area54.37 Å2Chemaxon
Rotatable Bond Count1Chemaxon
Refractivity94.11 m3·mol-1Chemaxon
Polarizability37.9 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-MS (2 MEOX; 1 TMS)GC-MSsplash10-004l-4911000000-d40ba45835d1ee1b6c41
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0k9f-4595000000-89ccbf45dbf9f474bd2f
GC-MS Spectrum - EI-BGC-MSsplash10-002o-9651000000-b44110f9abcffa42ce35
GC-MS Spectrum - GC-MSGC-MSsplash10-004l-4911000000-d40ba45835d1ee1b6c41
Mass Spectrum (Electron Ionization)MSsplash10-002f-9731000000-48d2266d41955ffa9ce4
MS/MS Spectrum - Quattro_QQQ 10V, PositiveLC-MS/MSsplash10-001i-0009000000-a157e4b4aa18bdbc2531
MS/MS Spectrum - Quattro_QQQ 25V, PositiveLC-MS/MSsplash10-052b-5900000000-42494c0ef4b45cfa5cf4
MS/MS Spectrum - Quattro_QQQ 40V, PositiveLC-MS/MSsplash10-052b-9700000000-d8a942a3dfdb061bd5c3
MS/MS Spectrum - EI-B (HITACHI M-80) , PositiveLC-MS/MSsplash10-002o-9651000000-b0c55e50343bf8ab3077
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0a4j-4930000000-c5056c0aac78a148ea92
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-0039000000-6851bce432b6a7861290
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-01wg-0964000000-368e044e482883335aba
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-0029000000-5e251cfa5f5762a32ac8
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-004r-2089000000-815c1eaad6303500ca25
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0avi-0910000000-4861b6b9b352a03c1f9a
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-0091000000-bfc24b418bc5afb78959
1H NMR Spectrum1D NMRNot Applicable
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-189.7328588
predicted
DarkChem Lite v0.1.0
[M-H]-175.7653444
predicted
DarkChem Standard v0.1.0
[M-H]-190.1189588
predicted
DarkChem Lite v0.1.0
[M-H]-189.4910588
predicted
DarkChem Lite v0.1.0
[M-H]-190.2469588
predicted
DarkChem Lite v0.1.0
[M-H]-180.10722
predicted
DeepCCS 1.0 (2019)
[M+H]+189.4665588
predicted
DarkChem Lite v0.1.0
[M+H]+177.9122717
predicted
DarkChem Standard v0.1.0
[M+H]+189.9219588
predicted
DarkChem Lite v0.1.0
[M+H]+189.6950588
predicted
DarkChem Lite v0.1.0
[M+H]+189.8526588
predicted
DarkChem Lite v0.1.0
[M+H]+182.09666
predicted
DeepCCS 1.0 (2019)
[M+Na]+189.8187588
predicted
DarkChem Lite v0.1.0
[M+Na]+190.0353588
predicted
DarkChem Lite v0.1.0
[M+Na]+190.0262588
predicted
DarkChem Lite v0.1.0
[M+Na]+189.1840588
predicted
DarkChem Lite v0.1.0
[M+Na]+190.3143588
predicted
DarkChem Lite v0.1.0
[M+Na]+188.78221
predicted
DeepCCS 1.0 (2019)

Enzymes

Details1. Cytochrome P450 3A4
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Bustos ML, Caritis SN, Jablonski KA, Reddy UM, Sorokin Y, Manuck T, Varner MW, Wapner RJ, Iams JD, Carpenter MW, Peaceman AM, Mercer BM, Sciscione A, Rouse DJ, Ramin SM: The association among cytochrome P450 3A, progesterone receptor polymorphisms, plasma 17-alpha hydroxyprogesterone caproate concentrations, and spontaneous preterm birth. Am J Obstet Gynecol. 2017 Sep;217(3):369.e1-369.e9. doi: 10.1016/j.ajog.2017.05.019. Epub 2017 May 15. [Article]

Drug created at July 20, 2018 21:05 / Updated at February 21, 2021 18:54