Details of the Drug

General Information of Drug (ID: DMFXUT8)

Drug Name

Oxymetholone

Synonyms

oxymetholone; Anasterone; 434-07-1; HMS3393H15

Indication

Disease Entry	ICD 11	Status	REF
Aplastic anemia	3A70	Approved	[1]
Aregenerative anemia	N.A.	Approved	[2]
Diamond-Blackfan anemia	N.A.	Approved	[2]
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Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

332.5

Logarithm of the Partition Coefficient (xlogp)

4.4

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

BDDCS Class: Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 1: high solubility and high permeability [3]
MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 15.038 micromolar/kg/day [4]

Chemical Identifiers

Formula: C21H32O3
IUPAC Name: (2Z,5S,8R,9S,10S,13S,14S,17S)-17-hydroxy-2-(hydroxymethylidene)-10,13,17-trimethyl-1,4,5,6,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one
Canonical SMILES: C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(C)O)CC[C@@H]4[C@@]3(C/C(=C/O)/C(=O)C4)C
InChI: InChI=1S/C21H32O3/c1-19-11-13(12-22)18(23)10-14(19)4-5-15-16(19)6-8-20(2)17(15)7-9-21(20,3)24/h12,14-17,22,24H,4-11H2,1-3H3/b13-12-/t14-,15+,16-,17-,19-,20-,21-/m0/s1
InChIKey: ICMWWNHDUZJFDW-DHODBPELSA-N

Cross-matching ID

PubChem CID: 5281034
ChEBI ID: CHEBI:7864
CAS Number: 434-07-1
DrugBank ID: DB06412
TTD ID: D0Q6NZ
INTEDE ID: DR1225

Repurposed Drugs (RPD)

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Molecular Interaction Atlas of This Drug

Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Steroid 5-alpha-reductase 1 (SRD5A1)_{Main DME}	DEOG15F	S5A1_HUMAN	Substrate	[5]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
11-beta-hydroxysteroid dehydrogenase type 2 (HSD11B2)	OTHF4H9U	DHI2_HUMAN	Gene/Protein Processing	[6]
Interleukin-6 (IL6)	OTUOSCCU	IL6_HUMAN	Gene/Protein Processing	[7]
Interleukin-7 (IL7)	OTT6YSKM	IL7_HUMAN	Gene/Protein Processing	[7]
Kit ligand (KITLG)	OTB9AVQ4	SCF_HUMAN	Gene/Protein Processing	[7]
Thyroid peroxidase (TPO)	OTJJLL20	PERT_HUMAN	Gene/Protein Processing	[7]

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Molecular Interaction Atlas (MIA)

MIA Detail

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Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Oxymetholone (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Remdesivir	DMBFZ6L	Moderate	Increased risk of hepatotoxicity by the combination of Oxymetholone and Remdesivir.	1D6YCoronavirus Disease 2019 [1D6YCoronavirus Disease 2019]	[8]
Bedaquiline	DM3906J	Moderate	Increased risk of hepatotoxicity by the combination of Oxymetholone and Bedaquiline.	Antimicrobial drug resistance [MG50-MG52]	[9]
Pexidartinib	DMS2J0Z	Major	Increased risk of hepatotoxicity by the combination of Oxymetholone and Pexidartinib.	Bone/articular cartilage neoplasm [2F7B]	[10]
Cannabidiol	DM0659E	Moderate	Increased risk of hepatotoxicity by the combination of Oxymetholone and Cannabidiol.	Epileptic encephalopathy [8A62]	[11]
Brentuximab vedotin	DMWLC57	Moderate	Increased risk of hepatotoxicity by the combination of Oxymetholone and Brentuximab vedotin.	Hodgkin lymphoma [2B30]	[12]
Teriflunomide	DMQ2FKJ	Major	Increased risk of hepatotoxicity by the combination of Oxymetholone and Teriflunomide.	Hyper-lipoproteinaemia [5C80]	[13]
BMS-201038	DMQTAGO	Major	Increased risk of hepatotoxicity by the combination of Oxymetholone and BMS-201038.	Hyper-lipoproteinaemia [5C80]	[14]
Calaspargase pegol	DMQZBXI	Moderate	Increased risk of hepatotoxicity by the combination of Oxymetholone and Calaspargase pegol.	Malignant haematopoietic neoplasm [2B33]	[15]
Idelalisib	DM602WT	Moderate	Increased risk of hepatotoxicity by the combination of Oxymetholone and Idelalisib.	Mature B-cell leukaemia [2A82]	[16]
Carfilzomib	DM48K0X	Major	Additive thrombogenic effects by the combination of Oxymetholone and Carfilzomib.	Multiple myeloma [2A83]	[8]
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References

1	Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
2	Oxymetholone FDA Label
3	BDDCS predictions, self-correcting aspects of BDDCS assignments, BDDCS assignment corrections, and classification for more than 175 additional drugs
4	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
5	Androgen physiology. Semin Reprod Med. 2006 Apr;24(2):71-7.
6	The anabolic androgenic steroid fluoxymesterone inhibits 11beta-hydroxysteroid dehydrogenase 2-dependent glucocorticoid inactivation. Toxicol Sci. 2012 Apr;126(2):353-61.
7	Direct and indirect effects of androgens on survival of hematopoietic progenitor cells in vitro. J Korean Med Sci. 2005 Jun;20(3):409-16. doi: 10.3346/jkms.2005.20.3.409.
8	Cerner Multum, Inc. "Australian Product Information.".
9	Product Information. Sirturo (bedaquiline). Janssen Pharmaceuticals, Titusville, NJ.
10	Product Information. Turalio (pexidartinib). Daiichi Sankyo, Inc., Parsippany, NJ.
11	Cerner Multum, Inc. "UK Summary of Product Characteristics.".
12	Product Information. Adcetris (brentuximab vedotin). Seattle Genetics Inc, Bothell, WA.
13	Canadian Pharmacists Association.
14	Product Information. Juxtapid (lomitapide). Aegerion Pharmaceuticals Inc, Cambridge, MA.
15	Al-Nawakil C, Willems L, Mauprivez C, et.al "Successful treatment of l-asparaginase-induced severe acute hepatotoxicity using mitochondrial cofactors." Leuk Lymphoma 55 (2014): 1670-4. [PMID: 24090500]
16	Product Information. Zydelig (idelalisib). Gilead Sciences, Foster City, CA.