Details of the Drug

General Information of Drug (ID: DMQXLD2)

Drug Name

Cyproterone

Synonyms

Ciproterona; Ciproterone; CyPat; Cyproteron; Cyproteronum; Ciproterona Servycal; Ciproterone [DCIT]; SH 80881; Apo-cyproterone; Ciproterona Servycal (TN); Ciproterona [INN-Spanish]; Cyproterone (INN); Cyproterone [INN:BAN]; Cyproteronum [INN-Latin]; Dianette (TN); Gen-Cyproterone; Novo-cyproterone; Diane-35 (TN); (1R,3aS,3bR,7aR,8aS,8bS,8cS,10aS)-1-acetyl-5-chloro-1-hydroxy-8b,10a-dimethyl-2,3,3a,3b,7a,8,8a,8b,8c,9,10,10a-dodecahydrocyclopenta[a]cyclopropa[g]phenanthren-7(1H)-one; 6-Chlor-delta(6)-1,2-alpha-methylen-17-alpha-hydroxyprogesteron; 6-Chlor-delta(sup 6)-1,2-alpha-methylen-17-alpha-hydroxyprogesteron; 6-Chlor-delta(sup 6)-1,2-alpha-methylen-17-alpha-hydroxyprogesteron [German]; 6-chloro-17-hydroxy-1beta,2beta-dihydro-3'H-cyclopropa[1,2]pregna-4,6-diene-3,20-dione

Indication

Disease Entry	ICD 11	Status	REF
Prostate cancer	2C82.0	Approved	[1]
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Therapeutic Class

Anticancer Agents

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

374.9

Logarithm of the Partition Coefficient (xlogp)

3.1

Rotatable Bond Count (rotbonds)

1

Hydrogen Bond Donor Count (hbonddonor)

1

Hydrogen Bond Acceptor Count (hbondacc)

3

Chemical Identifiers

Formula: C22H27ClO3
IUPAC Name: (1S,2S,3S,5R,11R,12S,15R,16S)-15-acetyl-9-chloro-15-hydroxy-2,16-dimethylpentacyclo[9.7.0.02,8.03,5.012,16]octadeca-7,9-dien-6-one
Canonical SMILES: CC(=O)[C@]1(CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2C=C(C4=CC(=O)[C@@H]5C[C@@H]5[C@]34C)Cl)C)O
InChI: InChI=1S/C22H27ClO3/c1-11(24)22(26)7-5-14-12-9-18(23)17-10-19(25)13-8-16(13)21(17,3)15(12)4-6-20(14,22)2/h9-10,12-16,26H,4-8H2,1-3H3/t12-,13+,14-,15-,16-,20-,21-,22-/m0/s1
InChIKey: DUSHUSLJJMDGTE-ZJPMUUANSA-N

Cross-matching ID

PubChem CID: 5284537
ChEBI ID: CHEBI:50742
CAS Number: 2098-66-0
TTD ID: D06AEO
VARIDT ID: DR00985

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Androgen receptor (AR)	TTS64P2	ANDR_HUMAN	Antagonist	[2]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Myb-related protein A (MYBL1)	OTBJMC2P	MYBA_HUMAN	Gene/Protein Processing	[3]
Protein GREB1 (GREB1)	OTU6ZA26	GREB1_HUMAN	Gene/Protein Processing	[3]
Serine/threonine-protein kinase Sgk1 (SGK1)	OT301T1U	SGK1_HUMAN	Gene/Protein Processing	[3]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease

Prostate cancer

ICD Disease Classification

2C82.0

Molecule Name	Molecule Type	Gene Name	p-value	Fold-Change	Z-score
Androgen receptor (AR)	DTT	AR	2.13E-01	-0.07	-0.11

Molecular Expression Atlas (MEA)

MEA Detail

Jump to Detail Molecular Expression Atlas of This Drug

References

1	Drug information of Cyproterone, 2008. eduDrugs.
2	Coactivator selective regulation of androgen receptor activity. Steroids. 2009 Aug;74(8):669-74.
3	A Gene Expression Biomarker Identifies Chemical Modulators of Estrogen Receptor in an MCF-7 Microarray Compendium. Chem Res Toxicol. 2021 Feb 15;34(2):313-329. doi: 10.1021/acs.chemrestox.0c00243. Epub 2021 Jan 6.