NAV

Luprostiol

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

Identification

Generic Name
Luprostiol
DrugBank Accession Number
DB11425
Background

Not Available

Type
Small Molecule
Groups
Experimental, Vet approved
Structure
3D
Similar Structures
Weight
Average: 444.97
Monoisotopic: 444.1373375
Chemical Formula
C21H29ClO6S
Synonyms
  • Luprostiol
  • Luprostiolum
External IDs
  • EMD 34946
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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
TargetActionsOrganism
AAndrogen receptor
inhibitor
Humans
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
Not Available

Interactions

Drug Interactions
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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AceclofenacThe therapeutic efficacy of Luprostiol can be decreased when used in combination with Aceclofenac.
AcemetacinThe therapeutic efficacy of Luprostiol can be decreased when used in combination with Acemetacin.
Acetylsalicylic acidThe therapeutic efficacy of Luprostiol can be decreased when used in combination with Acetylsalicylic acid.
AlclofenacThe therapeutic efficacy of Luprostiol can be decreased when used in combination with Alclofenac.
AminophenazoneThe therapeutic efficacy of Luprostiol can be decreased when used in combination with Aminophenazone.
Food Interactions
Not Available

Products

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International/Other Brands
Equestrolin / Prosolvin / Reprodin

Categories

Drug Categories
Classification
Not classified
Affected organisms
Not Available

Chemical Identifiers

UNII
HWR60H5GZB
CAS number
67110-79-6
InChI Key
KFUDFIMHDRJVLV-OZCLATTGSA-N
InChI
InChI=1S/C21H29ClO6S/c22-14-6-5-7-16(10-14)28-12-15(23)13-29-21-17(18(24)11-19(21)25)8-3-1-2-4-9-20(26)27/h1,3,5-7,10,15,17-19,21,23-25H,2,4,8-9,11-13H2,(H,26,27)/b3-1-/t15-,17-,18-,19+,21+/m1/s1
IUPAC Name
(5Z)-7-[(1R,2S,3S,5R)-2-{[(2R)-3-(3-chlorophenoxy)-2-hydroxypropyl]sulfanyl}-3,5-dihydroxycyclopentyl]hept-5-enoic acid
SMILES
O[C@H](COC1=CC(Cl)=CC=C1)CS[C@@H]1[C@@H](O)C[C@@H](O)[C@H]1C\C=C/CCCC(O)=O

References

General References
  1. Diehl JR, Newby TJ: Dosage response evaluation of luprostiol administered to pregnant sows. Theriogenology. 1989 Jul;32(1):11-7. [Article]
  2. Kiracofe GH, Wright JM, Newby TJ: Reproductive characteristics of cyclic beef heifers treated with the prostaglandin analog luprostiol. Theriogenology. 1988;30(5):931-6. [Article]
  3. Batista M, Nino T, Alamo D, Gonzalez F, Santana M, Rodriguez N, Cabrera F, Gracia A: Use of Luprostiol and Cloprostenol for induction of parturition in pregnant goats. Reprod Domest Anim. 2009 Feb;44(1):83-7. doi: 10.1111/j.1439-0531.2007.01001.x. Epub 2008 Jun 19. [Article]
  4. Plata NI, Spitzer JC, Thompson CE, Henricks DM, Reid MP, Newby TJ: Synchronization of estrus after treatment with Luprostiol in beef cows and in beef and dairy heifers. Theriogenology. 1990 May;33(5):943-52. [Article]
  5. Plata NI, Spitzer JC, Henricks DM, Thompson CE, Plyler BB, Newby TJ: Endocrine, estrous and pregnancy response to varying dosages of Luprostiol in beef cows. Theriogenology. 1989 Apr;31(4):801-12. [Article]
  6. Godfrey RW, Guthrie MJ, Neuendorff DA, Randel RD: Evaluation of luteolysis and estrous synchronization by a prostaglandin analog (Luprostiol) in Brahman cows and heifers. J Anim Sci. 1989 Aug;67(8):2067-74. [Article]
  7. Jochle W, Irvine CH, Alexander SL, Newby TJ: Release of LH, FSH and GnRH into pituitary venous blood in mares treated with a PGF analogue, luprostiol, during the transition period. J Reprod Fertil Suppl. 1987;35:261-7. [Article]
  8. Kerr DR, McGowan MR, Carroll CL, Baldock FC: Evaluation of three estrus synchronization regimens for use in extensively managed Bos indicus and Bos indicus/taurus heifers in Northern Australia. Theriogenology. 1991 Jul;36(1):129-41. [Article]
  9. Stolla R, Schmid G: [Effects of natural and synthetic PGF2 alpha preparations on the uterine contractility of cattle]. Berl Munch Tierarztl Wochenschr. 1990 Jun 1;103(6):198-202. [Article]
  10. Kumar H, Mogha IV, Yadav MC: Effect of treatment with buffalo follicular fluid on ovarian function in goats. Vet Rec. 1998 Aug 29;143(9):252-4. [Article]
KEGG Drug
D08151
ChemSpider
4945847
RxNav
2583725
ZINC
ZINC000033955191

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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 Solubility0.0229 mg/mLALOGPS
logP3.15ALOGPS
logP2.51Chemaxon
logS-4.3ALOGPS
pKa (Strongest Acidic)4.31Chemaxon
pKa (Strongest Basic)-2.9Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count6Chemaxon
Hydrogen Donor Count4Chemaxon
Polar Surface Area107.22 Å2Chemaxon
Rotatable Bond Count12Chemaxon
Refractivity114.75 m3·mol-1Chemaxon
Polarizability47.63 Å3Chemaxon
Number of Rings2Chemaxon
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
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-1020900000-b83672a9d1bb737a1e79
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-002g-1262900000-307774394bfa5f6e3c33
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a59-4293400000-bdc35d902fd587ff6c82
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-004l-6984700000-961c0eaf94a6ee101746
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-003i-6950000000-d7271116f914f0015df2
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-8954100000-69b7ac2c9200b36c1fe3
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
Not Available

Targets

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Details1. Androgen receptor
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Zinc ion binding
Specific Function
Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Transcription ...
Gene Name
AR
Uniprot ID
P10275
Uniprot Name
Androgen receptor
Molecular Weight
98987.9 Da
References
  1. Siddique HR, Mishra SK, Karnes RJ, Saleem M: Lupeol, a novel androgen receptor inhibitor: implications in prostate cancer therapy. Clin Cancer Res. 2011 Aug 15;17(16):5379-91. doi: 10.1158/1078-0432.CCR-11-0916. Epub 2011 Jun 28. [Article]

Drug created at February 25, 2016 18:40 / Updated at June 24, 2022 22:46