Details of the Drug

General Information of Drug (ID: DME7VZD)

Drug Name

Vilaprisan

Synonyms

Vilaprisan; UNII-IN59K53GI9; BAY1002670; IN59K53GI9; 1262108-14-4; Vilaprisan [INN]; BAY 1002670; Vilaprisan [USAN:INN]; Vilaprisan (USAN/INN); SCHEMBL2121854; CHEMBL3989936; BCP24069; DB11971; 20,20,21,21,21-Pentafluoro-17-hydroxy-11beta-(4-(methanesulfonyl)phenyl)-19-nor-17alpha-pregna-4,9-dien-3-one; 19-Norpregna-4,9-dien-3-one, 20,20,21,21,21-pentafluoro-17-hydroxy-11-(4-(methylsulfonyl)phenyl)-, (11beta,17alpha)-

Indication

Disease Entry	ICD 11	Status	REF
Endometriosis	GA10	Phase 2	[1]
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Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 1

Molecular Weight (mw)

544.6

Logarithm of the Partition Coefficient (xlogp)

4.1

Rotatable Bond Count (rotbonds)

3

Hydrogen Bond Donor Count (hbonddonor)

1

Hydrogen Bond Acceptor Count (hbondacc)

9

Chemical Identifiers

Formula: C27H29F5O4S
IUPAC Name: (8S,11R,13S,14S,17S)-17-hydroxy-13-methyl-11-(4-methylsulfonylphenyl)-17-(1,1,2,2,2-pentafluoroethyl)-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-3-one
Canonical SMILES: C[C@]12C[C@@H](C3=C4CCC(=O)C=C4CC[C@H]3[C@@H]1CC[C@]2(C(C(F)(F)F)(F)F)O)C5=CC=C(C=C5)S(=O)(=O)C
InChI: InChI=1S/C27H29F5O4S/c1-24-14-21(15-3-7-18(8-4-15)37(2,35)36)23-19-10-6-17(33)13-16(19)5-9-20(23)22(24)11-12-25(24,34)26(28,29)27(30,31)32/h3-4,7-8,13,20-22,34H,5-6,9-12,14H2,1-2H3/t20-,21+,22-,24-,25-/m0/s1
InChIKey: JUFWQQVHQFDUOD-ANRPBIDPSA-N

Cross-matching ID

PubChem CID: 50915138
CAS Number: 1262108-14-4
DrugBank ID: DB11971
TTD ID: D07YGK
INTEDE ID: DR1831

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Progesterone receptor (PGR)	TTUV8G9	PRGR_HUMAN	Antagonist	[2]

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Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Cytochrome P450 3A4 (CYP3A4)	DE4LYSA	CP3A4_HUMAN	Substrate	[3]
Succinic semialdehyde reductase (AKR7A2)	DE4G629	ARK72_HUMAN	Substrate	[3]

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Molecular Interaction Atlas (MIA)

MIA Detail

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Molecular Expression Atlas of This Drug

The Studied Disease

Endometriosis

ICD Disease Classification

GA10

Molecule Name	Molecule Type	Gene Name	p-value	Fold-Change	Z-score
Progesterone receptor (PGR)	DTT	PGR	3.26E-38	-3.79	-2.5
Cytochrome P450 3A4 (CYP3A4)	DME	CYP3A4	2.20E-02	-1.08E-01	-2.31E-01
Succinic semialdehyde reductase (AKR7A2)	DME	AKR7A2	2.53E-22	-6.86E-01	-9.08E-01

Molecular Expression Atlas (MEA)

MEA Detail

Jump to Detail Molecular Expression Atlas of This Drug

References

1	ClinicalTrials.gov (NCT02465814) Assess Safety and Efficacy of Vilaprisan in Patients With Uterine Fibroids.
2	Trusted, scientifically sound profiles of drug programs, clinical trials, safety reports, and company deals, written by scientists. Springer. 2015. Adis Insight (drug id 800033939)
3	Characterization of the pharmacokinetics of vilaprisan: bioavailability, excretion, biotransformation, and drug-drug interaction potential. Clin Pharmacokinet. 2018 Aug;57(8):1001-1015.