Details of the Drug

General Information of Drug (ID: DMZM84R)

Drug Name

Ethynodiol diacetate

Synonyms

Cervicundin; Continuin; Femulen; Luteonorm; Metrodiol; Ethinodiol diacetate; Ethyndiol Diacetate; Ethynodiol diacetate [Progestins]; Ethynodiol diacetate [USAN]; Etynodiol Acetate; Metrodiol diacetate; Ovulen 50; SC 11800; Etynodiol di(acetate); Luto-metrodiol; SC-11800; Ethynodiol diacetate (JAN/USP);[(3S,8R,9S,10R,13S,14S,17R)-17-acetyloxy-17-ethynyl-13-methyl-2,3,6,7,8,9,10,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate; (3 beta, 17 alpha)-19-Norpregn-4-en-20-yne-3,17 diolDiacetate; (3-beta,17-alpha)-19-Norpregn-4-en-20-yne-3,17-diol diacetate; (3beta,17beta)-17-ethynylestr-4-ene-3,17-diyl diacetate; 17-alpha-Ethynyl-19-norandrost-4-ene-3-beta,17-beta-diol diacetate; 17-alpha-Ethynyl-3,17-dihydroxy-4-estrene diacetate; 17-alpha-Ethynyl-4-estrene-3-beta,17-beta-diol diacetate; 17-alpha-Ethynylestr-4-ene-3-beta,17-beta-diol acetate; 17alpha-Ethynyl-19-norandrost-4-ene-3beta,17-beta-diol diacetate; 17alpha-Ethynyl-3,17-dihydroxy-4-estrene diacetate; 17alpha-Ethynyl-4-estrene-3beta,17beta-diol diacetate; 17alpha-Ethynylestr-4-ene-3beta,17beta-diol acetate; 17alpha-ethynylestr-4-ene-3beta,17beta-diyl diacetate; 19-Nor-17-alpha-pregn-4-en-20-yne-3-beta,17-diol diacetate; 19-Nor-17-alpha-pregn-4-en-20-yne-3-beta,17-diol, diacetate; 19-Nor-17alpha-pregn-4-en-20-yne-3beta,17-diol diacetate; 3-beta, 17-beta-Diacetoxy-17-alpha-ethynyl-4-oestrene; 3-beta,17-beta-Diacetoxy-19-nor-17-alpha-pregn-4-en-20-yne; 3beta, 17beta-Diacetoxy-17alpha-ethynyl-4-oestrene; 3beta,17beta-Diacetoxy-17alpha-ethynyl-4-estrene; 3beta,17beta-Diacetoxy-19-nor-17alpha-pregn-4-en-20-yne

Indication

Disease Entry	ICD 11	Status	REF
Contraception	QA21	Approved	[1], [2]

Therapeutic Class

Contraceptive Agents

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

384.5

Topological Polar Surface Area (xlogp)

3.9

Rotatable Bond Count (rotbonds)

5

Hydrogen Bond Donor Count (hbonddonor)

0

Hydrogen Bond Acceptor Count (hbondacc)

4

Chemical Identifiers

Formula: C24H32O4
IUPAC Name: [(3S,8R,9S,10R,13S,14S,17R)-17-acetyloxy-17-ethynyl-13-methyl-2,3,6,7,8,9,10,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
Canonical SMILES: CC(=O)O[C@H]1CC[C@@H]2[C@H]3CC[C@]4([C@H]([C@@H]3CCC2=C1)CC[C@]4(C#C)OC(=O)C)C
InChI: InChI=1S/C24H32O4/c1-5-24(28-16(3)26)13-11-22-21-8-6-17-14-18(27-15(2)25)7-9-19(17)20(21)10-12-23(22,24)4/h1,14,18-22H,6-13H2,2-4H3/t18-,19-,20+,21+,22-,23-,24-/m0/s1
InChIKey: ONKUMRGIYFNPJW-KIEAKMPYSA-N

Cross-matching ID

PubChem CID: 9270
ChEBI ID: CHEBI:31580
CAS Number: 297-76-7
DrugBank ID: DB00823
TTD ID: D0R2KY
INTEDE ID: DR0663

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Progesterone receptor (PGR)	TTUV8G9	PRGR_HUMAN	Binder	[3], [4]

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Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Cytochrome P450 3A4 (CYP3A4)_{Main DME}	DE4LYSA	CP3A4_HUMAN	Substrate	[5]

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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

Contraception

ICD Disease Classification

QA21

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

Molecular Expression Atlas (MEA)

MEA Detail

Jump to Detail Molecular Expression Atlas of This Drug

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: 7072).
2	FDA Approved Drug Products from FDA Official Website. 2009. Application Number: (NDA) 018168.
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21	Dienogest is a selective progesterone receptor agonist in transactivation analysis with potent oral endometrial activity due to its efficient pharm... Steroids. 2008 Feb;73(2):222-31.