Details of the Drug

General Information of Drug (ID: DMTPQ84)

Drug Name
(11-BETA)-11,21-DIHYDROXY-PREGN-4-ENE-3,20-DIONE
Synonyms
Corticosterone; CORTICOSTERONE; 50-22-6; 17-Deoxycortisol; Reichstein's substance H; Kendall's compound B; Corticosteron; 11beta,21-Dihydroxyprogesterone; Compound B; Reichstein's B; 11-Hydroxycorticoaldosterone; (11beta)-11,21-Dihydroxypregn-4-ene-3,20-dione; 11beta,21-Dihydroxy-4-pregnene-3,20-dione; 4-Pregnene-11beta,21-diol-3,20-dione; 11,21-Dihydroxyprogesterone; 11Beta,21-dihydroxypregn-4-ene-3,20-dione; 11,12-Dihydroxyprogesterone; UNII-W980KJ009P; CCRIS 6753; 11-beta,21-Dihydroxypregn-3,20-dione; CHEBI:16827; NSC9705; corticosterone
Indication
Disease Entry ICD 11 Status REF
Discovery agent N.A. Investigative [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 346.5
Logarithm of the Partition Coefficient (xlogp) 1.9
Rotatable Bond Count (rotbonds) 2
Hydrogen Bond Donor Count (hbonddonor) 2
Hydrogen Bond Acceptor Count (hbondacc) 4
Chemical Identifiers
Formula
C21H30O4
IUPAC Name
(8S,9S,10R,11S,13S,14S,17S)-11-hydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
Canonical SMILES
C[C@]12CCC(=O)C=C1CC[C@@H]3[C@@H]2[C@H](C[C@]4([C@H]3CC[C@@H]4C(=O)CO)C)O
InChI
InChI=1S/C21H30O4/c1-20-8-7-13(23)9-12(20)3-4-14-15-5-6-16(18(25)11-22)21(15,2)10-17(24)19(14)20/h9,14-17,19,22,24H,3-8,10-11H2,1-2H3/t14-,15-,16+,17-,19+,20-,21-/m0/s1
InChIKey
OMFXVFTZEKFJBZ-HJTSIMOOSA-N
Cross-matching ID
PubChem CID
5753
ChEBI ID
CHEBI:16827
CAS Number
50-22-6
DrugBank ID
DB04652
TTD ID
D03TNT
VARIDT ID
DR00499
INTEDE ID
DR0382
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
Corticosteroid 11-beta-dehydrogenase 1 (HSD11B1) TTN7BL9 DHI1_HUMAN Inhibitor [2]
Glucocorticoid receptor messenger RNA (GCR mRNA) TTOZRK6 GCR_HUMAN Agonist [3]
Mineralocorticoid receptor (MR) TT26PHO MCR_HUMAN Inhibitor [2]

Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
P-glycoprotein 1 (ABCB1) DTUGYRD MDR1_HUMAN Substrate [4]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4)
Main DME 		DE4LYSA CP3A4_HUMAN Substrate [5]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Androgen receptor (AR) OTUBKAZZ ANDR_HUMAN Gene/Protein Processing [6]
Angiotensinogen (AGT) OTBZLYR3 ANGT_HUMAN Regulation of Drug Effects [7]
Broad substrate specificity ATP-binding cassette transporter ABCG2 (ABCG2) OTW8V2V1 ABCG2_HUMAN Gene/Protein Processing [8]
Cytochrome P450 11B1, mitochondrial (CYP11B1) OTKKL894 C11B1_HUMAN Biotransformations [9]
Cytochrome P450 11B2, mitochondrial (CYP11B2) OTIOLWYN C11B2_HUMAN Biotransformations [10]
Cytochrome P450 1A2 (CYP1A2) OTLLBX48 CP1A2_HUMAN Gene/Protein Processing [11]
Cytochrome P450 2A6 (CYP2A6) OT52TWG3 CP2A6_HUMAN Gene/Protein Processing [11]
Cytochrome P450 2B6 (CYP2B6) OTOYO4S7 CP2B6_HUMAN Gene/Protein Processing [11]
Cytochrome P450 2C9 (CYP2C9) OTGLBN29 CP2C9_HUMAN Gene/Protein Processing [11]
Cytochrome P450 2D6 (CYP2D6) OTZJC802 CP2D6_HUMAN Gene/Protein Processing [11]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Discovery agent
ICD Disease Classification N.A.
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Glucocorticoid receptor messenger RNA (GCR mRNA) DTT NR3C1 3.19E-02 0.54 1.67
Corticosteroid 11-beta-dehydrogenase 1 (HSD11B1) DTT HSD11B1 2.03E-01 -0.01 -0.08
Mineralocorticoid receptor (MR) DTT NR3C2 7.31E-01 -5.31E-04 -1.53E-03
P-glycoprotein 1 (ABCB1) DTP P-GP 2.30E-01 3.06E-01 7.43E-01
Cytochrome P450 3A4 (CYP3A4) DME CYP3A4 2.76E-01 -4.64E-01 -9.16E-01
Molecular Expression Atlas (MEA) 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: 2869).
2 The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42.
3 Functional probing of the human glucocorticoid receptor steroid-interacting surface by site-directed mutagenesis. Gln-642 plays an important role in steroid recognition and binding. J Biol Chem. 2000Jun 23;275(25):19041-9.
4 Antiestrogens and steroid hormones: substrates of the human P-glycoprotein. Biochem Pharmacol. 1994 Jul 19;48(2):287-92.
5 Studies on pharmacokinetic drug interaction potential of vinpocetine. Medicines (Basel). 2015 Jun 5;2(2):93-105.
6 Chemical genomics profiling of environmental chemical modulation of human nuclear receptors. Environ Health Perspect. 2011 Aug;119(8):1142-8. doi: 10.1289/ehp.1002952. Epub 2011 May 4.
7 Steroid profiling in H295R cells to identify chemicals potentially disrupting the production of adrenal steroids. Toxicology. 2017 Apr 15;381:51-63.
8 Human breast cancer resistance protein: interactions with steroid drugs, hormones, the dietary carcinogen 2-amino-1-methyl-6-phenylimidazo(4,5-b)pyridine, and transport of cimetidine. J Pharmacol Exp Ther. 2005 Jan;312(1):144-52. doi: 10.1124/jpet.104.073916. Epub 2004 Sep 13.
9 Steroid signalling in the ovarian surface epithelium. Trends Endocrinol Metab. 2005 Sep;16(7):327-33.
10 Fine-tuning the selectivity of aldosterone synthase inhibitors: structure-activity and structure-selectivity insights from studies of heteroaryl substituted 1,2,5,6-tetrahydropyrrolo[3,2,1-ij]quinolin-4-one derivatives. J Med Chem. 2011 Apr 14;54(7):2307-19.
11 Prenatal ethanol exposure induces dynamic changes of expression and activity of hepatic cytochrome P450 isoforms in male rat offspring. Reprod Toxicol. 2022 Apr;109:101-108. doi: 10.1016/j.reprotox.2022.03.002. Epub 2022 Mar 14.