Details of the Drug

General Information of Drug (ID: DM9R1YU)

Drug Name
Gestodene
Synonyms
Gestinol; Gestoden; Gestodene [USAN:INN:BAN]; Gestodeno; Gestodeno [INN-Spanish]; Gestodenum; Gestodenum [INN-Latin]; SH B 331; GESTODENE; 13-Ethyl-17-hydroxy-18,19-dinor-17alpha-pregna-4,15-dien-20-yn-3-one; 1664P6E6MI; 17-alpha-Ethinyl-13-ethyl-17-beta-hydroxy-4,15-gonadien-3-one; 18,19-Dinorpregna-4,15-dien-20-yn-3-one, 13-ethyl-17-hydroxy-, (17-alpha)-; 60282-87-3; BRN 4237181; CCRIS 9189; DSSTox_CID_26478; DSSTox_GSID_46478; DSSTox_RID_81649; EINECS 262-145-8; HSDB 3594; UNII-1664P6E6MI
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 310.4
Logarithm of the Partition Coefficient (xlogp) 2.9
Rotatable Bond Count (rotbonds) 2
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 2
ADMET Property
Bioavailability
93% of drug becomes completely available to its intended biological destination(s) [1]
Clearance
The drug present in the plasma can be removed from the body at the rate of 0.8 mL/min/kg [2]
Half-life
The concentration or amount of drug in body reduced by one-half in 16 - 18 hours [2]
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 0.0046 micromolar/kg/day [3]
Unbound Fraction
The unbound fraction of drug in plasma is 0.023% [2]
Vd
Fluid volume that would be required to contain the amount of drug present in the body at the same concentration as in the plasma 0.46 L/kg [2]
Chemical Identifiers
Formula
C21H26O2
IUPAC Name
(8R,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-17-hydroxy-1,2,6,7,8,9,10,11,12,14-decahydrocyclopenta[a]phenanthren-3-one
Canonical SMILES
CCC12CCC3C(C1C=CC2(C#C)O)CCC4=CC(=O)CCC34
InChI
SIGSPDASOTUPFS-XUDSTZEESA-N
InChIKey
1S/C21H26O2/c1-3-20-11-9-17-16-8-6-15(22)13-14(16)5-7-18(17)19(20)10-12-21(20,23)4-2/h2,10,12-13,16-19,23H,3,5-9,11H2,1H3/t16-,17+,18+,19-,20-,21-/m0/s1
Cross-matching ID
PubChem CID
3033968
ChEBI ID
CHEBI:135323
CAS Number
60282-87-3
DrugBank ID
DB06730
INTEDE ID
DR0770
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4)
Main DME 		DE4LYSA CP3A4_HUMAN Substrate [4]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Cytochrome P450 3A4 (CYP3A4) OTQGYY83 CP3A4_HUMAN Gene/Protein Processing [5]
Vitamin K-dependent protein C (PROC) OTGVH484 PROC_HUMAN Gene/Protein Processing [6]
Vitamin K-dependent protein S (PROS1) OTXQWNOI PROS_HUMAN Gene/Protein Processing [7]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 Critical Evaluation of Human Oral Bioavailability for Pharmaceutical Drugs by Using Various Cheminformatics Approaches
2 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
3 Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
4 Effect of an oral contraceptive preparation containing ethinylestradiol and gestodene on CYP3A4 activity as measured by midazolam 1'-hydroxylation. Br J Clin Pharmacol. 2000 Oct;50(4):333-7.
5 Catalytic activities of human liver cytochrome P-450 IIIA4 expressed in Saccharomyces cerevisiae. Biochemistry. 1990 Dec 25;29(51):11280-92.
6 Oral contraceptives, thrombosis and haemostasis. Eur J Obstet Gynecol Reprod Biol. 2001 Apr;95(2):193-7. doi: 10.1016/s0301-2115(00)00489-9.
7 Effect of oral and transdermal estrogen replacement therapy on hemostatic variables associated with venous thrombosis: a randomized, placebo-controlled study in postmenopausal women. Arterioscler Thromb Vasc Biol. 2003 Jun 1;23(6):1116-21. doi: 10.1161/01.ATV.0000074146.36646.C8. Epub 2003 May 1.