Details of the Drug

General Information of Drug (ID: DMBGWPH)

Drug Name
Medroxyprogesterone
Synonyms
Asconale; Colirest; Hematrol; Hydroxymethylprogesterone; Lunelle; Medrossiprogesterone; Medroxiprogesterona; Medroxiprogesteronum; Medroxyprogesteron; Medroxyprogesteronum; Methylhydroxyprogesterone; Adgyn Medro; Farlutal inyectable; Medroprogesterone Acetate; Medrossiprogesterone [DCIT]; Medroxyprogesteron acetate; Medroxyprogesterone Strakan Brand; Sodelut G; Strakan Brand of Medroxyprogesterone; MPA Gyn 5; U 8840; CBP-1011; Farlutal inyectable (TN); G-Farlutal; Medroxiprogesterona [INN-Spanish]; Medroxyprogesterone (INN); Medroxyprogesterone [INN:BAN]; Medroxyprogesteronum [INN-Latin]; Novo-Medrone; Pregn-4-ene-3,20-dione, 17-hydroxy-6-methyl-, (6alpha)-(9CI); Pregn-4-ene-3,20-dione, 17-hydroxy-6-methyl-, (6-alpha)-(9CI); (6S,8R,9S,10R,13S,14S,17R)-17-acetyl-17-hydroxy-6,10,13-trimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one; (6alpha)-17-hydroxy-6-methylpregn-4-ene-3,20-dione; 17 alpha Hydroxy 6 alpha Methylprogesterone; 17 alpha-Hydroxy-6 alpha-Methylprogesterone; 17-Hydroxy-6.alpha.-methylprogesterone; 17-Hydroxy-6alpha-methyl-pregn-4-ene-3,20-dione; 17-Hydroxy-6alpha-methylprogesterone; 17.alpha.-Hydroxy-6.alpha.-methylprogesterone; 17alpha-Hydroxy-6alpha-methyl-4-pregnene-3,20-dione; 17alpha-Hydroxy-6alpha-methylprogesterone; 6-Dihydromegestrol; 6-alpha-Methyl-17-alpha-hydroxyprogesterone; 6.alpha.-Methyl-17.alpha.-hydroxyprogesterone; 6alpha-Methyl-17alpha-hydroxyprogesterone; 6alpha-Methyl-4-pregnen-17alpha-ol-3,20-dione; 6alpha-Methyl-5-pregnen-17alpha-ol-3,20-dione
Indication
Disease Entry ICD 11 Status REF
Solid tumour/cancer 2A00-2F9Z Approved [1]
Therapeutic Class
Contraceptive Agents
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 344.5
Logarithm of the Partition Coefficient (xlogp) 3.5
Rotatable Bond Count (rotbonds) 1
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 3
ADMET Property
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 4: low solubility and low permeability [2]
Elimination
44% of drug is excreted from urine in the unchanged form [2]
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 0.061 micromolar/kg/day [3]
Water Solubility
The ability of drug to dissolve in water is measured as 0.022 mg/mL [2]
Adverse Drug Reaction (ADR)
ADR Term Variation Related DOT DOT ID REF
Breast cancer Not Available mpra OTEUBPKL [4]
Breast cancer Not Available ESR1 OTKLU61J [4]
Chemical Identifiers
Formula
C22H32O3
IUPAC Name
(6S,8R,9S,10R,13S,14S,17R)-17-acetyl-17-hydroxy-6,10,13-trimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one
Canonical SMILES
C[C@H]1C[C@@H]2[C@H](CC[C@]3([C@H]2CC[C@@]3(C(=O)C)O)C)[C@@]4(C1=CC(=O)CC4)C
InChI
InChI=1S/C22H32O3/c1-13-11-16-17(20(3)8-5-15(24)12-19(13)20)6-9-21(4)18(16)7-10-22(21,25)14(2)23/h12-13,16-18,25H,5-11H2,1-4H3/t13-,16+,17-,18-,20+,21-,22-/m0/s1
InChIKey
FRQMUZJSZHZSGN-HBNHAYAOSA-N
Cross-matching ID
PubChem CID
10631
ChEBI ID
CHEBI:6715
CAS Number
520-85-4
TTD ID
D0I2SD
INTEDE ID
DR1012
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Progesterone receptor (PGR) TTUV8G9 PRGR_HUMAN Agonist [5]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4)
Main DME 		DE4LYSA CP3A4_HUMAN Substrate [6]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Cytochrome P450 2C8 (CYP2C8) OTHCWT42 CP2C8_HUMAN Gene/Protein Processing [7]
Estrogen receptor (ESR1) OTKLU61J ESR1_HUMAN Drug Response [4]
Membrane progestin receptor alpha (mpra) OTEUBPKL MPRA_CYNNE Drug Response [4]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Solid tumour/cancer
ICD Disease Classification 2A00-2F9Z
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) Jump to Detail Molecular Expression Atlas of This Drug

References

1 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
2 BDDCS applied to over 900 drugs
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 ADReCS-Target: target profiles for aiding drug safety research and application. Nucleic Acids Res. 2018 Jan 4;46(D1):D911-D917. doi: 10.1093/nar/gkx899.
5 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.
6 Metabolic profiling and cytochrome P450 reaction phenotyping of medroxyprogesterone acetate. Drug Metab Dispos. 2008 Nov;36(11):2292-8.
7 Examination of 209 drugs for inhibition of cytochrome P450 2C8. J Clin Pharmacol. 2005 Jan;45(1):68-78.