Details of the Drug

General Information of Drug (ID: DMJ6H1Z)

Drug Name

Quinestrol

Synonyms

EECPE; Eston; Estrovis; Estrovister; Plestrovis; Quilea; Quinestrolo; Quinestrolum; Quinestrolo [DCIT]; Estrovis 4000; W 3566; Estrovis (TN); Ethinyl Estradiol 3-Cyclopentyl Ether; Qui-Lea; Quinestrolum [INN-Latin]; W-3566; Quinestrol (USAN/INN); Quinestrol [USAN:INN:BAN]; Estradiol-17-beta 3-cyclopentyl ether; (8R,9S,13S,14S,17R)-3-cyclopentyloxy-17-ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-ol; 17-alpha-Ethinylestradiol 3-cyclopentyl ether; 17ALPHA-ETHYLNYL-1,3,5[10]ESTRATRIENE-3,17BETA-DIOL 3-CYCLOPENTYL ETHER; 17alpha-Ethynyl-1,3,5(10)-estratriene-3,17beta-diol 3-cyclopentyl ether; 17alpha-Ethynylestradiol 3-cyclopentyl ether; 3-(Cyclopentyloxy)-19-nor-17-alpha-pregna-1,3,5(10)-trien-20-yn-17-ol; 3-(Cyclopentyloxy)-19-nor-17alpha-pregna-1,3,5(10)-trien-20-yn-17-ol; 3-(cyclopentyloxy)-17beta-ethynylestra-1,3,5(10)-trien-17-ol; 3-Cyclopentyloxy-17alpha-ethynylestra-1,3,5(10)-trien-17beta-ol

Indication

Disease Entry	ICD 11	Status	REF
Breast cancer	2C60-2C65	Approved	[1]
Hot flushes	GA30	Approved	[2]
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Therapeutic Class

Anticancer Agents

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 1

Molecular Weight (mw)

364.5

Logarithm of the Partition Coefficient (xlogp)

5.3

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

Absorption: The drug is absorbed after oral administration []
Metabolism: The drug is metabolized via the liver []

Chemical Identifiers

Formula: C25H32O2
IUPAC Name: (8R,9S,13S,14S,17R)-3-cyclopentyloxy-17-ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-ol
Canonical SMILES: C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(C#C)O)CCC4=C3C=CC(=C4)OC5CCCC5
InChI: InChI=1S/C25H32O2/c1-3-25(26)15-13-23-22-10-8-17-16-19(27-18-6-4-5-7-18)9-11-20(17)21(22)12-14-24(23,25)2/h1,9,11,16,18,21-23,26H,4-8,10,12-15H2,2H3/t21-,22-,23+,24+,25+/m1/s1
InChIKey: PWZUUYSISTUNDW-VAFBSOEGSA-N

Cross-matching ID

PubChem CID: 9046
ChEBI ID: CHEBI:8716
CAS Number: 152-43-2
DrugBank ID: DB04575
TTD ID: D04UZT

Repurposed Drugs (RPD)

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Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Estrogen receptor (ESR)	TTZAYWL	ESR1_HUMAN	Modulator	[3]

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Molecular Interaction Atlas (MIA)

MIA Detail

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Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Quinestrol (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Ivosidenib	DM8S6T7	Moderate	Increased metabolism of Quinestrol caused by Ivosidenib mediated induction of CYP450 enzyme.	Acute myeloid leukaemia [2A60]	[4]
Arn-509	DMT81LZ	Moderate	Increased metabolism of Quinestrol caused by Arn-509 mediated induction of CYP450 enzyme.	Acute myeloid leukaemia [2A60]	[4]
Pexidartinib	DMS2J0Z	Moderate	Increased metabolism of Quinestrol caused by Pexidartinib mediated induction of CYP450 enzyme.	Bone/articular cartilage neoplasm [2F7B]	[5]
Lumacaftor	DMCLWDJ	Moderate	Increased metabolism of Quinestrol caused by Lumacaftor mediated induction of CYP450 enzyme.	Cystic fibrosis [CA25]	[5]
MK-8228	DMOB58Q	Moderate	Decreased metabolism of Quinestrol caused by MK-8228 mediated inhibition of CYP450 enzyme.	Cytomegaloviral disease [1D82]	[6]
Cenobamate	DM8KLU9	Moderate	Increased metabolism of Quinestrol caused by Cenobamate mediated induction of CYP450 enzyme.	Epilepsy/seizure [8A61-8A6Z]	[4]
Eslicarbazepine	DMZREFQ	Moderate	Increased metabolism of Quinestrol caused by Eslicarbazepine mediated induction of CYP450 enzyme.	Epilepsy/seizure [8A61-8A6Z]	[4]
ABT-450	DMFW860	Major	Decreased metabolism of Quinestrol caused by ABT-450 mediated inhibition of UGT.	Hepatitis virus infection [1E50-1E51]	[7]
Brigatinib	DM7W94S	Moderate	Increased metabolism of Quinestrol caused by Brigatinib mediated induction of CYP450 enzyme.	Lung cancer [2C25]	[8]
PF-06463922	DMKM7EW	Moderate	Increased metabolism of Quinestrol caused by PF-06463922 mediated induction of CYP450 enzyme.	Lung cancer [2C25]	[4]
Selpercatinib	DMZR15V	Moderate	Decreased metabolism of Quinestrol caused by Selpercatinib mediated inhibition of CYP450 enzyme.	Lung cancer [2C25]	[9]
IPI-145	DMWA24P	Moderate	Decreased metabolism of Quinestrol caused by IPI-145 mediated inhibition of CYP450 enzyme.	Mature B-cell leukaemia [2A82]	[10]
Vemurafenib	DM62UG5	Moderate	Increased metabolism of Quinestrol caused by Vemurafenib mediated induction of CYP450 enzyme.	Melanoma [2C30]	[4]
Dabrafenib	DMX6OE3	Moderate	Increased metabolism of Quinestrol caused by Dabrafenib mediated induction of CYP450 enzyme.	Melanoma [2C30]	[4]
Carfilzomib	DM48K0X	Major	Additive thrombogenic effects by the combination of Quinestrol and Carfilzomib.	Multiple myeloma [2A83]	[6]
Nilotinib	DM7HXWT	Moderate	Decreased metabolism of Quinestrol caused by Nilotinib mediated inhibition of CYP450 enzyme.	Myeloproliferative neoplasm [2A20]	[11]
Abametapir	DM2RX0I	Moderate	Decreased metabolism of Quinestrol caused by Abametapir mediated inhibition of CYP450 enzyme.	Pediculosis [1G00]	[12]
Lefamulin	DME6G97	Moderate	Decreased metabolism of Quinestrol caused by Lefamulin mediated inhibition of CYP450 enzyme.	Pneumonia [CA40]	[13]
Lonafarnib	DMGM2Z6	Moderate	Decreased metabolism of Quinestrol caused by Lonafarnib mediated inhibition of CYP450 enzyme.	Premature ageing appearance [LD2B]	[14]
Enzalutamide	DMGL19D	Moderate	Increased metabolism of Quinestrol caused by Enzalutamide mediated induction of CYP450 enzyme.	Prostate cancer [2C82]	[4]
Temsirolimus	DMS104F	Moderate	Increased plasma concentrations of Quinestrol and Temsirolimus due to competitive inhibition of the same metabolic pathway.	Renal cell carcinoma [2C90]	[15]
Telotristat ethyl	DMDIYFZ	Moderate	Increased metabolism of Quinestrol caused by Telotristat ethyl mediated induction of CYP450 enzyme.	Small intestine developmental anomaly [DA90]	[16]
Larotrectinib	DM26CQR	Moderate	Decreased metabolism of Quinestrol caused by Larotrectinib mediated inhibition of CYP450 enzyme.	Solid tumour/cancer [2A00-2F9Z]	[6]
Armodafinil	DMGB035	Minor	Increased metabolism of Quinestrol caused by Armodafinil mediated induction of CYP450 enzyme.	Solid tumour/cancer [2A00-2F9Z]	[17]
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References

1	URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 7097).
2	Quinestrol FDA Label
3	The antioxidant effect of estrogen and Selective Estrogen Receptor Modulators in the inhibition of osteocyte apoptosis in vitro. Bone. 2007 Mar;40(3):674-84.
4	Baciewicz AM "Oral contraceptive drug interactions." Ther Drug Monit 7 (1985): 26-35. [PMID: 2859674]
5	Back DJ, Breckenridge AM, Crawford FE, MacIver M, Orne ML, Rowe PH "Interindividual variation and drug interactions with hormonal steroid contraceptives." Drugs 21 (1981): 46-61. [PMID: 7009137]
6	Cerner Multum, Inc. "Australian Product Information.".
7	Product Information. Norvir (ritonavir). Abbott Pharmaceutical, Abbott Park, IL.
8	Product Information. Alunbrig (brigatinib). Ariad Pharmaceuticals Inc, Cambridge, MA.
9	Product Information. Retevmo (selpercatinib). Lilly, Eli and Company, Indianapolis, IN.
10	Product Information. Copiktra (duvelisib). Verastem, Inc., Needham, MA.
11	Product Information. Tasigna (nilotinib). Novartis Pharmaceuticals, East Hanover, NJ.
12	Product Information. Xeglyze (abametapir topical). Dr. Reddy's Laboratories Inc, Upper Saddle River, NJ.
13	Product Information. Xenleta (lefamulin). Nabriva Therapeutics US, Inc., King of Prussia, PA.
14	Product Information. Zokinvy (lonafarnib). Eiger BioPharmaceuticals, Palo Alto, CA.
15	Product Information. Prograf (tacrolimus). Fujisawa, Deerfield, IL.
16	Cerner Multum, Inc. "UK Summary of Product Characteristics.".
17	Doherty MM, Charman WN "The mucosa of the small intestine: how clinically relevant as an organ of drug metabolism?" Clin Pharmacokinet 41 (2002): 235-53. [PMID: 11978143]